Jun Kwak, co-founder and CTO of Overjoy, joins us to talk about why he believes every B2B SaaS company will have to become a service business, how Overjoy went from selling software to delivering sales outcomes for consumer brands, why tangled data is the strongest moat against the frontier labs, how AI agents could weaken wholesale marketplaces, why brands need websites AI agents can read, why small brands chasing big box stores often abandon their most profitable channel, whether agents will turn premium products into commodities, and what three national debate championships taught him about running a company.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

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Links

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Show Notes

Jun Kwak & Jim O’Shaughnessy

• Jun Kwak: Co-founder and CTO of Overjoy. Connect on LinkedIn

• Overjoy: The AI-powered wholesale growth platform Jun co-founded with Alex Han. Overjoy

• Overjoy on X: Follow Overjoy on X

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned

• Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig: The source of Jim’s story about a friend outraged that his BMW motorcycle was fixed with a scrap of aluminum can. Zen and the Art of Motorcycle Maintenance

• Influence by Robert Cialdini: The classic text on persuasion Jim cites when asking whether AI will master it. Influence

• Sebastian Barry: The Irish novelist whose McNulty book A Temporary Gentleman Jim discussed with his AI agent. Sebastian Barry

• Consumer Reports: Jim’s model for a trusted product-rating source in a world of AI shopping agents. Consumer Reports

• Collapse of Silicon Valley Bank: The 2023 bank run that locked up Overjoy’s seed funding. Collapse of Silicon Valley Bank

• Faire: The wholesale marketplace Jun cites as the market leader. Faire

• Electronic data interchange (EDI): The ordering system big box retailers require, and one reason small brands fear that channel. Electronic data interchange

Highlights

On Agent Marketplaces

Jim O’Shaughnessy
We mentioned Amazon, right? They’ve turned off access to the agents. I think that ultimately is not going to be a winning proposition. And my guess is, and I’d be interested in your point of view, that Amazon itself will have its own group of agents. But I don’t know how much the consumer is going to trust that those agents are going to actually find them either the best product or the best price or whatever. How do you see this whole thing unfolding? This is kind of a broader question than just your specific company […] is there an opportunity for a new marketplace that caters directly to agents, for example?

Jun Kwak
Yeah, that is definitely a possibility. But I think these marketplaces require both sides to be signed on to that platform. The analogy would be: would you want to only crawl through Wikipedia articles or Reddit articles, or would you want to get information from any source on the internet? I think that’s the analogy here, and the reason why even...

Jim O’Shaughnessy
I like that one. That’s really good.

Jun Kwak
Maybe I should be using that more. But yeah, basically, the reason why... I mean, when we first started, we thought, there are these big wholesale marketplaces, and would it make sense for these brands to set up their own wholesale portal? The truth is, there are always buyers that are not on those marketplaces...

Jim O’Shaughnessy
Right.

Jun Kwak
...and you still want to do business with them, and that’s why you always need a direct channel. And agents make it even easier for the buyers to find, keep buying from and build relationships with these small and mid-sized brands on their direct channel as well. So I do believe in that direction, and in a sense this actually disintermediates the marketplaces that were able to build that walled garden because of the limitation of human attention, which is now gone with agents.

Edited Transcript

Jim O’Shaughnessy
Well, hello everyone, it’s Jim O’Shaughnessy with yet another Infinite Loops. Today I have Jun Kwak, the co-founder of Overjoy, one of the first portfolio companies that O’Shaughnessy Ventures... As opposed to our earlier investments, this one was one of the first that O’Shaughnessy Ventures as an entity made. Jun, welcome.

Jun Kwak
Thank you for having me.

Jim O’Shaughnessy
So I thought that what might really be helpful for us and for our listeners and viewers today is for you to give kind of an account of the journey, right? I think a lot of people thinking about founding a company, especially young, might have a lot of questions. And I think that, having seen how you guys have progressed over the last several years, you’ve got a lot of answers. But first off, tell us a bit about the company and why you decided, “You know what? I think rather than trying to get a job at McKinsey or whatever, I think I’d rather start my own company.”

Jun Kwak
So yeah, happy to share a bit about Overjoy first, and how we decided to start Overjoy instead of getting a job elsewhere. At Overjoy, we are basically delivering sales and revenue teams to consumer brands. We actually started as a startup building a software stack for small and mid-sized brands to scale their wholesale channel. When we first interviewed a bunch of brand founders, even though they started their business as a direct-to-consumer model, which is, imagine you shoot Meta ads, Instagram ads, and direct them to your own website, a lot more of these brands were trying to sell to other businesses, like, say, local boutique shops or other local stores. And that’s a pretty expensive channel, because you need to invest in a full sales team and you need a dedicated software stack to run that.

So that’s how we started building tools to help brands scale that channel. And that went pretty well. We scaled and were able to get to a decent revenue milestone, but we still felt like we weren’t really solving the biggest pain point for these brands, which was that they still needed someone to run the software stack. So that’s when we started talking to more folks in this space, and we even saw some of our users taking our software and turning that into a consulting business and selling it at a 20x, 40x price. So that kind of helped us land on more of where we are today. But happy to share more about that in detail.

Jim O’Shaughnessy
So tell me a little bit about the process in determining what made you target this particular market. Was it a big search across all of the available opportunities? Was there just a glaring empty space there? What was it that made you do this, as opposed to any number of other...

Jun Kwak
Yeah. So I think that from very early on, I had a... So I guess I can start from my journey as a 13-, 14-year-old.

Jim O’Shaughnessy
Please.

Jun Kwak
So I grew up in Korea, and at that time somehow I got into debate for the first time in English class. And that was fascinating, because if you’re in Korea, even though it’s a peninsula, it’s basically an island, with North Korea. So basically the only way to learn about how the world works is through news, and debate felt like you can actually talk about those topics with logic. So I was fascinated by that and I started going to debate tournaments, and I ended up winning three national championships in Korea at age 15. And then after that I came to the realisation that you get to talk about all these topics, but nothing gets solved. So that’s when... One of my friends was into game development, so I thought it was cool to build stuff on your computer. So I started self-teaching myself how to code, and built my first game, built my first app. And that was kind of the second half of my high school. I actually quit debate, all the public speaking, mock trial, everything, and I went on learning how to code, and felt like if I get good at this, I can actually go build things to solve problems in the world. And yeah, I ended up going to Yale. I was one of the first 10 Presidential Scholars from Korea, so that helped me move here to the States and start my journey here. And I first felt like I should be a good engineer, so that was all I was focused on throughout Yale.

I ended up working at Google AI, Snapchat, Robinhood. And I think that’s when I started feeling the itch of, “Huh, I feel like I can now build something that people will actually use. What if I actually go try to build my own startup?” So I had a stronger itch to build my own startup, but I did not have a clear picture of what that space would be. And I think in that sense, going through a new grad accelerator programme helped a lot. So I ended up going to the SF Bay Area. We had two big hacker houses, and that’s how I actually met my co-founder, Alex. We went through so many different spaces. It’s embarrassing to talk about right now, because there were so many bad ideas that we explored. Even in terms of different areas, we went from fashion design tools to crypto tools to all these different sorts of spaces. But then I came to realise that you should really like the people that you build for. And after going through different domains, when I was talking to these brand founders, they’re all super passionate about what they built, what they make, and they’re just really cool people to hang out with.

So even though we had a very vague, murky idea of what problem we wanted to solve, it was pretty clear that we wanted to build for the brand founders. I remember talking to one of our first customers, his name is Tyler. He founded a brand called Cinnamon. They want to be the Hershey’s for cinnamon and horchata products. And I still text him, and he’s still very passionate about his brand. And I think from very early on, even though we had very little idea about the space, it was very clear that this is the space that we do want to be in, and the people that we want to be around.

Jim O’Shaughnessy
So, quite the underachiever. By the way, what did your debate experience teach you that you brought over to becoming a founder? Because I found one of the rarest things that I look for in founders are people who don’t want to just yap about things, right? Because debate, I love debate, I think it’s great and I think you can learn a lot of really good skills in it, but you’ve got to want to actually do something about it. But what did all of your debate experience teach you, and what did you bring that sharpened you as a founder?

Jun Kwak
That’s a great question. I just thought of two things. One is, since I’m CTO of our company, I lead the product engineering team, and there’s a lot of overlap between computer science and debate. Code is essentially logic. So when I was making that transition... I actually never thought I would be in a STEM field as a kid. I really didn’t like math, but coding, computer science, it felt like a lot more overlap with debate, in that you need to be logical, you need to understand how machines work. So that helped me through that transition.

Another thing is more about how I work with my co-founder, Alex. So, fun fact: he’s also a debater too. He did debate as a high schooler. And one superpower that we have as a team, I think, is we are not that emotionally attached to the arguments that we have. And this is almost different from ego. It’s more like, how can you handle disagreements? How can you handle these attacks on things that you strongly believe in? And because we both come from a debate background, I think it’s easy for us to detach ourselves from what we are saying, and also from the attacks that the other person is throwing at me. So that oftentimes helps our arguments tremendously, because basically we’ll talk about what to build or how to build a specific search feature, and we both feel fine flipping our stance an hour later because, logically, the other side makes a lot more sense. So I think it helps a lot for us to uncover the truth behind what to build, how to build, how to sell, all these problems that you face as a founder.

Jim O’Shaughnessy
Yeah, I think the ability to pivot, the ability to have an open mind to a variety of paths forward, it increases your cognitive space enormously. And if you have, like, “We’re gonna build X,” right? And then X becomes the only thing, and “Nope, that doesn’t serve X. Nope.” You can miss a tremendous amount. And you actually experienced this, right? Because you started realising there was a whole different segment that you probably should be servicing. Talk a little bit about that, about the services part of the business.

Jun Kwak
Yeah. So basically, more and more we are calling ourselves and branding ourselves as a service company, because what we are realising is small and mid-sized brands lack the resources to spin up a full sales team. And even though you give them the best tools, it’s hard for brands to use those tools, or even orchestrate the agents to get to the most, say, AI-pilled or agent-pilled sales team. So this was a pilot experiment that we actually started running earlier this year. The whole time, we’ve been giving them search tools, email campaign tools and CRM to create a full sales pipeline and turn them into opening orders. “What if we just deliver the outcome?” was the thought that we had. So we had a first set of brands where they still had access to the software, but there’s no need to do that. Just talk to our team and we will run it. Just tell us what you want: what outreach targets you want, what messaging you want us to benchmark. And with that plan that we agreed with the brand, we just went on and launched the entire outreach campaign and outreach sales process. And it turns out the brands were happier that way. Brands got more visibility into how things were going. And it was also not that far from how brands were working with, say, in-house hires or other agencies. But we were able to deliver that in a way more efficient way, but also with better outcomes, because we owned the software stack, we owned the agent stack.

So yeah, now we have three main services. We have an outreach service, where basically we deliver interested buyers to these brands. We have a conversion service, where we own, say, 100, 200 active deals in their pipeline, and we run all the manual work of email follow-ups, sending them sample products, figuring out the pricing and discounts for these wholesale buyers. And the last one is reordering and expansion, where what’s interesting for these physical products, unlike, say, software sales or insurance, is that they’re not on subscription. You need to constantly go through the sales process, even for your existing customers. So every time there’s a new product launch, you need to let them know, get pre-orders and upsell your existing customers on these new products. So we have the third service that’s responsible for that. And with that, we are seeing two-person brands that had never had a sales hire be able to expand their existing accounts through our service.

Jim O’Shaughnessy
So I want to come back to that, because I’m very intrigued by that part of your build-out. But let’s do a case study. Somebody is a small brand, let’s say they’re here and they’ve got a little shop, and they don’t know about you guys yet, but then they meet you and they hire you. What do they look like when they discover you? What kind of operation are they running? What are the kind of sales numbers, et cetera? And then what do they look like after you’ve been fully embedded into their company?

Jun Kwak
Yeah. So the truth is, we work with small brands that are less than 1 million GMV, to 1 to 50, and then 50-plus, and the needs for these are all slightly different. Say it’s a very small brand, say one or two founders just run the brand. Oftentimes they don’t have a working wholesale engine. So they come to us and they want us to build out the entire...

Jim O’Shaughnessy
And let me stop you for a second. Can you give us an example of what they are selling?

Jun Kwak
Oh yeah. So one of our brands, they sell leather goods, say, leather coasters. And they are a two-person brand based in Minnesota, and they have an existing channel, but because they don’t have a sales team, they just have their products on online wholesale marketplaces. The market leader there is Faire, and because of how marketplaces are structured, they tend to pay a very high commission for the sales that they get through those marketplaces. And there’s very little control over how you can increase your sales through those marketplaces, because you don’t have an in-house salesperson. So when they came to us, they basically had 10,000 customers. They only had opening orders, and they never got reorders from those accounts.

And imagine you try to do this as a founder: you would probably dig through all your sales history. The biggest problem actually is it’s really hard to combine your email data and your order data in one place. You might think, “Oh, we can use agents to do that,” but to run that at scale, on 10,000 accounts from five different sources, becomes an actual data problem. So oftentimes it’s really hard to build that source of truth for someone to go in and figure out a very simple question of: which of my accounts should I go out and tell about our new product launches? So when they actually came to us, we took over that customer management side. And every day we have 50 to 100 customer win-back campaigns, where we know exactly what they purchased before and what is the best product that we can recommend for them to purchase next. And with that alone, they were able to go from zero to $15,000 in Overjoy-attributed revenue in the past 30 days. And that number actually keeps going up, because we are building up the account management motion for the wholesale channel.

Jim O’Shaughnessy
And give me an example of what the workflow looks like that determines: okay, so they bought this leather coaster or whatever. How many different products are you researching that are available for this company to offer a returning customer? And then what is the algorithm or the agent that determines, “No, this is the one we pitch them,” and why?

Jun Kwak
Yeah. So basically, when brands onboard to our service, even though they think that they are only getting the sales service, for us to power that, we do onboard them to our entire software platform. So when they come in, we sync with their Shopify, Faire, QuickBooks and all their email communication channels as well. And we build out their system of record, where they can see their whole list of accounts. And with that, what we are able to do is start grouping them, and basically building out their customer profiles for their wholesale channel. So as we group them, we can then see what the top-selling products are for each of these groups.

So say I’m a brand selling protein shakes: I can group my customers based on fitness gyms, yoga studios and grocery stores, and then rank which of my products are the best-selling products per category. And then, on a per-account basis, these agents can go and look up all the products that each account bought and has not bought, and recommend the best sellers.

Jim O’Shaughnessy
Okay, so you look at what they bought from your client, then you look at what they bought elsewhere, and then you find the most adjacent thing that your client is offering, to offer to them. What does the funnel look like, in terms of you... You are now part of this smaller brand thing. How do you do A/B? Take me through. Is there A/B testing, or is it just, “Yeah, no, they’re buying a ton of this, and this we offer”? Do you have to have a price advantage? Do you have to have a quality advantage? Is there a secret sauce?

Jun Kwak
Yeah. So for any sales outreach, there’s target, there’s message, and there are a lot of tactics on what the call to action should be. So those are the three things that we do experiments on, on behalf of these brands. I would say that the experiments actually happen more for new-account campaigns than for customer campaigns. But what that looks like is, the same protein shake brand will come in, and we’ll actually launch three different campaigns for different ICPs. What’s actually interesting is, even though a lot of brand founders think that they would land better in certain accounts, because that’s what they saw in the retail channel and wholesale channel, oftentimes, depending on how they bundle their products and how they price them, what lands for wholesale is completely different from their direct-to-consumer channel. So we do...

Jim O’Shaughnessy
Let me stop you there. And my guess is they’re not aware of that.

Jun Kwak
Yeah, exactly. Which is actually a hard thing for us to convince them of, and that’s why we do run experiments. So when they first onboard, they fill out this outreach form. That’s our seed for their brand brain, or internally we call it the brand wiki. So each brand founder will come in and identify, “Oh, I want to reach out to CrossFit gyms, and I want to reach out to grocery stores, and I might want to try yoga studios, but I’m not sure how it will end.” Then, with that, we have our local business database that maps all the local businesses across the US and Canada, and we are able to find the most similar retailers to the ones that they’ve identified.

And with that, we start having two or three different campaigns with slightly different email copy, and we change the brand voice, we change what the offerings are, because sometimes you want to just go and send sample products, sometimes they want to give them more of a catalogue and let them know more about the brand. So we will run these experiments, be able to return it back to the brand, and double down on the ones that work better.

Jim O’Shaughnessy
So it’s an iterative process. And do you often find that your clients... do they just go along, or do they fight with you, or what’s the normal experience like?

Jun Kwak
Yeah. So I think this is actually the beauty of how we’ve transitioned from more of a software and subscription-based business into services. Because if you go two years back and look at our pricing page, we did the very standard SaaS seat-based pricing. Brands come in, they pay for, say, two seats, five seats, and they pay for credits, which is essentially how many new leads, new potential email contacts, I can go and run outreach to. Now, fast forward to where things are now: it’s more outcome-based pricing.

Brands pay for 20, like 40 interested buyers, and there we actually abstract out the parts of identifying the targets, creating... It doesn’t matter if you do three campaigns or five campaigns, and run it on 500 buyers or 3,000 buyers. Essentially we deliver the outcome, as if this is how you would work with, say, an SDR or a sales agency. It’s more of a sales process that runs on autopilot.

Jim O’Shaughnessy
Who are your competitors?

Jun Kwak
So right now there are more of the newer players. But I think on the sales side, we haven’t lost deals to anyone in our space. I think what we are more excited about is, I think there are a lot of adjacent problems that these brands... In terms of competitors, right now in the pure sales space, we don’t see any dominant players that are competing with us. There are one or two newer players that we are still taking a look at, but we haven’t lost any deals for our current service offering, on the outreach side and the conversion and retention side of our services. What I do believe is a lot of the SaaS companies in CPG will also move towards a service motion.

And even for us, our customers are asking us to expand our offering to inventory management and accounting and other back-office problems that they internally face. So I think it’ll be pretty exciting in the next 6 to 12 months to see how this pans out. And I think there are players that are on you to build accounting software or other types of software stack that brands use that are also trying to expand their service to more of a broader offering.

Jim O’Shaughnessy
So let’s take a moment and envision the person out there who is watching or listening to us, and they’re contemplating founding their own company.

Jun Kwak
Yeah.

Jim O’Shaughnessy
Take me through, like, the six things that happened that were completely not on your radar, and how you dealt with them.

Jun Kwak
Great question. I don’t have six in my mind at first, but I’ll start with things that just pop into my mind.

Jim O’Shaughnessy
Sure.

Jun Kwak
I do remember when SVB went down and basically all our funding was locked up in this account, and I actually remember calling you, Jim. We were like, “We don’t have any cash flow. This is it.” And that was actually right after we closed our seed round, and we were like, “Okay, finally we can relax. We can now not worry about money for a bit and go build cool stuff.” And yep, that happens. And I remember calling you, and fortunately over the weekend everything was sorted out. But yeah, I remember you assuring us that you actually went through multiple bank runs, and how this will be handled, and that was a big relief, because as a first-time founder I did not expect something like that could even happen.

Other things: because we build a software stack, we have a lot of integration partners, and there was a case... I would not mention the exact name of the company, but with one of the integration partners, we have one shared developer account where all the engineers share logins, and no one really checks the inbox. And they were sending us all their updates and how we need to make sure we are compliant with the integration partner’s app settings, and no one was checking it. And one day all of our customers got an email, a very scary email, that, “Oh, the Overjoy app will be removed from this app store.” And we had to reassure our customers that it will not affect the process, and we were able to sort it out. But that was also one of those moments where we did not expect that things like that could happen. So yeah, a lot of this firefighting.

I would say one more story there would be... I do remember very early on, our search... I think this is also when all these language model providers, OpenAI, Anthropic, they do require you to go through a moderation endpoint, so you don’t accidentally try to look up harmful content. But what happened was, one day we got a warning, and then they actually stopped our API access. This was very early on, when it was just me and Alex and our founding engineer at the time, but they basically cut our access to OpenAI, and we were digging through the data, and it just turned out, in our local business search product, there were some people that were looking up adult stores, and there’s no filtering on whether that hits the OpenAI endpoint or not. So we had to make sure that restriction was lifted, which we did through the people we have in our network. But all these things were definitely things that we did not expect, did not sign up for. But it’s just part of being a founder, I guess.

Jim O’Shaughnessy
And I think also, for example, the Silicon Valley Bank, having been through a lot of that, would freak any new founder out, I think. And what about your clients, though? Did they get wind of all of that, and what was their reaction like? Because I also want to hear a bit about, like, are your clients all of a certain type of personality? Obviously they’re not technical, would be my guess. Correct me if I’m wrong. But is there kind of a translation tax that you have to pay to get them to understand, “No, no, wait, you can do this so much better”?

Jun Kwak
Yeah, I have literally three different thoughts that just popped into my head at the same time. So there are definitely... I think these macro changes also do affect our customers too. It could range from... I remember when there were all the changes in tariffs, and all these small and mid-sized brands were affected by that, and they had all these questions. It’s very unpredictable in terms of what the next six months of inventory would look like. And we actually saw those things do affect them more emotionally, even though logically you should keep your outbound engine, you should keep running your sales process. But then most brands, especially as a two-person brand, get scared of all these macro trends, and they would actually pause or change their strategy for how they approach wholesale.

Those are more economic trends. Even on the technical side, a lot of brands struggle when there’s a new launch. Grokbot comes out, Claude’s new update comes out, and they want to use these agents, they want to use these frontier models in their workflows, but they do struggle a lot with how to incorporate that into their products. We even faced that too when we were rolling out our sales agent products earlier this year, and this was before we had the service motion. So we do all these tutorials, we try to teach how these brands can adopt and use these agents to run order processing, run outreach and run customer management. And it was actually pretty difficult to explain the best practices when the best practices change in real time. What we recommended a month ago is no longer the best practice, because with new models we actually do make changes to how things work.

So that’s actually one of those things that contributed, that helped us make that decision to be a lot more service-forward. Because, especially when things are changing so quickly on agents and AI, I think it’s a lot easier for us to deliver the outcome with the best orchestration of software, automation and agents for these brands, than for these brand founders to understand what’s the cost difference between Opus and Fable, and “How should I... What is MCP? How do I connect them to my workflow?” So that actually was our conclusion, and that seemed to land better with our customers lately.

Jim O’Shaughnessy
And are they of a type of personality where they’re just very eager to outsource? And I mean, your services are growing wildly. How do you scale that, though? How is that going to scale? Let’s say you continue with the kind of demand you’ve been seeing recently. Scale it for me.

Jun Kwak
Yeah. So with one of our new services, the full sales service, in the past four weeks we actually had 4x operational efficiency. Now, how we do that is a couple of things. I used to only lead the product and engineering team, but four weeks ago Alex and I made the decision that I should also be leading the account management team, because internal operations is basically product when we are a service company. So now I’m going to talk about what this unlocks, but then also all the new problems I’m faced with. The unlock actually is that now it gives immense clarity to a product person in any company like us. Because now you know what the service you’re trying to sell is, and what the price point is, first, before you go and build all the software and product that leads up to it. In a sense it removes all the guesswork from the product development cycle.

Because most of tech startup 101, how you build a product, is you talk to users, you have these hypotheses on what those problems are, and basically, if you build X, it will solve Y. And then you take it to the design and development phase, where you try to figure out the best mock-up, the best prototype to solve that problem. You implement it, you run QA, and then you bring it back and see if that actually yielded results for your customers. Now, in the service world, you can actually go straight to what these brands want, with an actual sales expert delivering that service. And in-house, you keep labelling: what are the things that are making this person inefficient, what are the things that we can actually automate with our software automations, and what are the things that we can actually improve with agents?

So that’s basically... it flips how we build products. You go from outcome first, even on the internal product building side, and you actually go backwards and keep improving the efficiency of how we deliver the service. So that’s what it unlocks for us. Because before, Alex and I would have all these debates on what will happen if you launch this new ordering product. We don’t know, we don’t know how it will land, we don’t know how people use it, but we’ll just need to test it out. And you spend all this time trying to build that out, and then it may or may not work. It basically removes the guesswork and adds a lot of clarity on what you’re trying to optimise for.

Now, internal operations-wise, it just means that I have a whole new set of problems I need to deal with internally. And what we came to realise is our account managers are essentially the experts. The reason why services work is because what we believe is, for all of these services, whether it’s outreach or sales management, you have, say, 5 to 10% where it requires human judgement. Whether it’s, does this fit with what this brand wants to represent? Does it fit with their strategy for this year? All these strategies that require human judgement and review. And the rest tends to be more amplifying that and actually executing that plan.

So that’s essentially how we’re trying to design our services and how we deliver them, where each account manager owns the strategic part of all these sales processes. And then the actual work that is involved there, making sure all of the leads that we do market research on are qualified based on the criteria that this brand sets, making sure all the samples that get sent out match the budget that we actually set, all that actual work that needs to be done on our platform becomes more and more automated with agents and our software stack.

So basically what we essentially did is we built a product-service loop, where we match each account manager with an engineer in our team, and every day we review all the inefficiencies, all the time sucks of our internal operations. And that feeds into how we improve the agent quality, and adding more things to our product roadmap to improve the workflow. So that actually led us to getting the 4x efficiency improvements on our full sales service offering. And right now I can’t share the exact margins, but basically we are able to offer services at close to software-company margins right now.

Jim O’Shaughnessy
And as I was listening to you: are there any universals? Because you’re obviously dealing with very disparate brands, right? Like leather goods and protein powders, you wouldn’t think, share much in common. But is there a universal? Is there an Ur-pattern, if you will, that underlies marketing anything?

Jun Kwak
That is a great question. And right now, what we’ve done is we have these loops, even among these agents, because essentially we have the full data of what all these brands have tried and what works best. And of course there are differences based on their category or their size, but you get to then see all the trends. There are things that we used to recommend anecdotally. Say, if you attach a large file or image to your cold outreach email, it’s not going to land in the inbox. But then we never knew that for sure. Whereas once we hit a critical mass of outbound emails and we actually ran analytics on the best patterns that we should recommend, that actually turned out to be true. But then there are also some counterintuitive things. It actually turns out emojis on subject lines help, but emojis in the body are bad. So we get to actually learn from what people tried and all the actual outcomes, and we can constantly improve what these agents can do on the outreach side.

And we’ve done this in a pretty semi-automated, somewhat manual way. But soon, what we are headed towards, even within how we use and improve our agents, is for all the agents that run on these brands, they’re going to be able to do... basically, I think the space is now calling them self-improving agents. Now they can actually see the patterns of these agent runs across these brands, identify the patterns that actually yielded better outcomes, and constantly improve. And I think that’s why, whenever we launch new agents or services, we never try to launch a standalone one that doesn’t integrate with our stack, because we want to make sure that data flows in, we can actually see the full outcome and whether that was very good or bad, and that flows in and can improve our software and agents continuously. So that’s how we determine which space, which new service, we’re going to launch. It can actually have a compounded data effect of improving our agent quality with those added data sources on our platform.

Jim O’Shaughnessy
And the brands that are your clients, do they grok all this? Do they really understand what’s going on? Or are they just like, “Yeah, no, you do it, we love the fact that our sales are going way up”? Or do they really understand the process?

Jun Kwak
So I would say yes and no. We do expose our software stack to brands. This is actually the reason why brands prefer to work with us than some third-party agencies, because they tend to be pretty secretive about who they contact, and they have their own walled garden of contacts or buyers that they work with. For us, it’s all about transparency. We market ourselves as basically an embedded sales department for your brand, so you should have control over all the data and all the software stack that we’re building for you. And oftentimes they get surprised looking at the CRM that is well maintained three months later, because they only thought that they were getting inbound leads. So yeah, probably not real time. But then we don’t hide anything. We try to give them full exposure to the underlying things that we use to run it, because essentially we are constantly using our software and agents to run this.

But what you pointed to does relate to an interesting new problem that we are facing, which is that how we interface with brands is changing as we evolve from a software company to a service company. Because what we are realising is a good chunk of our customers are now just talking to us on email. They just tell us what they want, and things get done. Right now our product manager, Ramil, and I are thinking a lot about: what is the new interface that we need to build for our brands? Because it is different. The assumptions are different. We’re not having those customers as software users. They’re more like clients for the service, and what we need to report back or summarise or explain about what’s happening is changing because of this transition.

Jim O’Shaughnessy
Has a client ever come to you with a really good idea that you guys thought, “Wow, why didn’t we think of that?” and then you actually incorporated it in your stack?

Jun Kwak
So actually, having the main sales email end with, “Would you like samples? Can I send this to this address?” is now a pattern that a lot of our brands use. But that was actually from a few people who really had this idea that even the brands that sell products that are really hard to send samples of need to create the smallest, cheapest product and send physical samples for the buyers to engage with and understand their brand. So that was actually from looking at and working with sales managers in these brands that had those hacks. And we were able to have more brands benefit from those sales hacks.

Jim O’Shaughnessy
And go through your customer acquisition funnel. How are you attracting customers? Is it word of mouth from your existing client base? What other ways are you getting new clients?

Jun Kwak
Yeah, I’d say right now we are still primarily outbound, but we’re increasingly having more inbound, as now we have 3,000 customers working with us. And I think now there’s more word of mouth and referrals coming in. But for a long time our primary sales engine was our outbound engine. And so basically what we give to our customers is essentially the same as what we use in-house to reach other brands. And what I often tell our customers is: cold outreach email is all about qualification. If you reach out to a store that is a good, compatible buyer for your brand, then it’s a business opportunity. If it’s not, it becomes a spam email.

So it all comes down to: can you qualify and do very deep market research to find the best retailers that match your brand? So that’s what we’ve really tried to crack the code on in the last couple of years, for our outreach engine but also for our brands’ outreach. And Alex went through four big iterations of making sure we can do that. There are a lot of technical innovations that allow us to do things like this. Because models got cheaper and faster, now we are able to use products like Clay to score all these businesses at scale. But then there was even one more unlock this year with Jeff, which is a System 1 model, where, because it’s built to score things, not write things, it’s way faster and cheaper for qualification of business opportunities. So with that, we actually completely rebuilt how we score these brands on their intent, on whether they are engaging with their wholesale channel. And this week we’re actually building that for our customers, starting with our service customers, because this actually increases the quality of leads that they can reach out to for their outbound sales motion.

Jim O’Shaughnessy
And what is the size of your total addressable market here?

Jun Kwak
So right now there are 3 million e-commerce Shopify businesses that sell physical goods, and only 700,000 of them are engaging in the wholesale channel. And that’s essentially because wholesale is a pretty expensive channel to run. So our first goal is to be able to democratise that sales process and deliver this agent-pilled sales department for these brands. But I think this will be a second Shopify effect, where, if you think about how brands were selling in the pre-Shopify era, you would still have to figure out how to put your products online. You’d have to have developers and designers to set up your own website, and then try to figure out how to get them to pay, all that. Remove the need of having your internal tech department, and just go start selling as a one-person founder. There’s still a big barrier to entry for the wholesale channel. And what we’re essentially doing is allowing even the smallest players to be able to grow their B2B wholesale channel.

Jim O’Shaughnessy
Okay, so let’s say I’ve got, again, a little shop with my wife, and we sell, oh, snow globes, and you’re going to pitch me. And what does that pitch look like? How do you get them excited about, like, “Ooh, wholesale”? “That seems like a big headache to me,” et cetera. How do you get them to become a customer?

Jun Kwak
Yeah. Right now, I mean, our sales team probably has a 10x better pitch than I do. But what I should tell them is: give us a shot, and in 30 days we’ll bring you 20 interested buyers that match your brand, that want to stock your products on their shelves. And it’s not just a one-time thing. We’ll build out an engine where we can constantly get you predictable sales opportunities every month, and you only pay when we hit those targets. And once you do that, you will start having a sales pipeline of 50, 100 and 200 opportunities, and someone will need to manage all the communications with those opportunities.

Now, you can decide to hire someone to run that in-house, or you can try to work with an external agency, or let us run that sales pipeline, and we will handle everything from email replies, giving them quotes, sending sample products, giving them marketing materials to push them down the sales pipeline. And essentially this turns a very tedious wholesale process into almost direct-to-consumer-like simplicity, where you basically just focus on the orders coming in and the opportunities coming in.

Jim O’Shaughnessy
So, Jun, are you at all worried about the frontier labs just essentially cloning what you’re doing and offering it as a skill?

Jun Kwak
So I think that’s the reason why I think all B2B SaaS companies will have to become a service business. Because I think there are only two paths: either you become a service business and try to automate not just the software stack but also how you use that, and build your proprietary data, or you just become a tool that models call, and eventually even that gets replaced. So I think there were a couple of reasons why Alex and I, even earlier this year... I think everyone was pretty shocked by the newer Claude models and how that could impact each vertical. And when we looked at our market, the more data sources you need to deal with... essentially, it’s a data structure and data complexity problem, where if your data is flat, say it’s a single spreadsheet and it explains everything, then it becomes very easy for one agent to just take over and abstract away the software stack.

Jim O’Shaughnessy
Sure.

Jun Kwak
But then, once you have two, three, four, with all these relationships in between... because for us, we have a list of businesses, and then contacts, and then their orders, and then each of these sources have locations, and each of these products have inventory data, and this comes from five different data sources. This becomes hard for someone to build, or for agents to build. And that makes it harder for frontier labs to just... unless they’re actually going into that very specific wholesale market. I think that’s where it becomes harder for model improvements to accidentally kill a space.

But then, not just that. I think on the service side, what we are most bullish on is the amount of data that we are getting just for our space, that is also tied to natural outcome quality data. And we are able to constantly improve our service with that data and improve our agents with that data. So this is how we can keep building our data moats through services. And this is why we’re a lot more excited and bullish than afraid about what the next launches are from the AI labs.

Jim O’Shaughnessy
And I don’t know the answer to this, but I would assume that data set in and of itself is very valuable. Have you agreed with your clients that it doesn’t get resold, so then it simply becomes an advantage for you and your company, as opposed to others joining the field? How much time... You’ve been in the business for several years now. When does that data compound to a point where it’s going to be really hard for a new entrant to reach your level of understanding, because you have all of this data versus them starting a new enterprise today?

Jun Kwak
Yeah, I think for some of the more mature services, like the cold outreach lead generation side of our offering, I think we’ve already reached that point, where we have the best data that fuels that engine, but also the outcomes keep improving. That’s where it becomes really hard. Alex and I talked about how, let’s say we have to start everything from scratch, you would have to go through the exact same path to build out this product, and then build out this current distribution, and then get to a point where it constantly improves the model. We reached that point for our lead generation side. For our full sales service side, I think we’ll reach that point in the next two months, because we’ve passed that pilot phase. We’re trying to build data on these brands that are running the full sales process with us, and we’re now going through the first set of loops to improve those agents with that data. So yeah, I think in the next two months we’ll reach the point where we have that for our entire sales process that we offer for our brands.

Jim O’Shaughnessy
And let’s talk results. What kind of numbers are you seeing, improvement for your clients from prior to when they hired you, obviously, but then with the new service model as well? What kind of lift are you offering?

Jun Kwak
Yeah, so we ran some data analysis, and our service customers have a 3x bigger sales pipeline generated through us than brands that are trying to use our software and run it themselves.

Jim O’Shaughnessy
That’s just, like, extraordinary.

Jun Kwak
Yeah. And that happened when we first launched it, for the first month, and now, six months in, that still holds true. So we were able to scale that level of overall sales efficiency boost as we scaled our entire sales programme.

Jim O’Shaughnessy
But what does that curve look like, right? Does your 3x, which is astounding, does that then just flatten out? Does it continue to improve? What does that look like?

Jun Kwak
So I think that’s hard to say, what the next low-hanging fruit would be or how we will get there. Right now we’re focused more on how we can optimise for... Yeah. So right now, actually, with the 3x boost, we were able to deliver that for six months. So we are trying to copy and paste that performance boost, not on the lead generation side, but on the full sales process side. So that means: can we 3x their conversion rate, bringing more of those opportunities to closed deals? And for those customers, can we have a boost on the reorder rates? So basically, since we proved out that boost on the lead generation side, we’re trying to bring that to the rest of their sales funnel, down the stack to their conversion and retention problems.

Jim O’Shaughnessy
And how sensitive are you to macroeconomic trends, and, like, what happens during the next recession?

Jun Kwak
So I think for us the biggest thing is: can we be the most affordable and also the best-performing way to run your sales department? So I actually think that... we still have some brands where, “Oh, because they’ve worked with a sales agency for a while, I want to keep them for a bit,” even though they are offering at a way higher price and actually performing way less efficiently than us. So I actually think that, say, if there’s more external pressure on these brands to run it in a lot more lean way, I think we would be the best in the market, because we are able to offer the same service or a better service at a fraction of their price.

Jim O’Shaughnessy
And that’s what intrigued me and led us to be one of your first investors, right? The disintermediation. My thesis has always been... I call it the Great Reshuffle, right? And that all of the old playbooks are collapsing, and there’s so much fat, if you will, from what the old players were charging, the results that they were delivering. You seem to be vastly better on both. You’re cheaper and you’re delivering better results, as I understand it. How are they still in business?

Jun Kwak
I think what we realise is that this space does move... No, it’s not the fastest-moving domain. But I think what’s interesting is the whole trend of agent e-commerce. Because I think that, in a sense, as more and more sellers and buyers are used to using agents, it actually does change how things get purchased. One of the biggest conventional wisdoms of how commerce works is that there are always these marketplaces that tax all these sellers, because they are able to get you customers, they give you the best shopping experience. And that’s the same for wholesale too. There are these wholesale marketplaces that charge 20, 25% commissions on top of their wholesale price, which is already a discount of their products. And it’s because it is a way easier shopping experience for their wholesale buyers. And that makes sense. Even as a shopper, it’s a lot easier for me to just order things on Amazon than to crawl through a hundred different brands’ websites and try to track what the lowest price is.

But in the age of agent e-commerce, agents can actually go through and compare prices on 200 different websites. And I think that’s why there is actually a world where more and more brands will want to sell a lot more direct, whether it’s retail customers or wholesale customers. And that’s why we actually launched our storefront products last week, and we are actually offering that for free. These software vendors used to charge hundreds and thousands of dollars just for their wholesale portal, because brands that were able to do wholesale had the budget to purchase expensive software. But what we are seeing is more and more small and mid-sized brands will want to set up their direct wholesale channel. And buyers are also going to be able to buy from lots of separate, scattered direct portals, because agents are able to bundle that for the human buyers.

Jim O’Shaughnessy
And I thought that the age of agentic buying and selling would potentially be very deflationary, because the previous market was very inefficient, and agents don’t get tired, they don’t need a coffee break, et cetera. But what do you think about big brands? We mentioned Amazon, right? They’ve turned off access to the agents. I think that ultimately is not going to be a winning proposition. And my guess is, and I’d be interested in your point of view, that Amazon itself will have its own group of agents. But I don’t know how much the consumer is going to trust that those agents are going to actually find them either the best product or the best price or whatever. How do you see this whole thing unfolding? This is kind of a broader question than just your specific company.

Jun Kwak
Is the question basically how these larger marketplaces would respond to this, and what that...

Jim O’Shaughnessy
But also, is there an opportunity for a new marketplace that caters directly to agents, for example?

Jun Kwak
Yeah, that is definitely a possibility. But I think these marketplaces require both sides to be signed on to that platform. The analogy would be: would you want to only crawl through Wikipedia articles or Reddit articles, or would you want to get information from any source on the internet? I think that’s the analogy here, and the reason why even...

Jim O’Shaughnessy
I like that one. That’s really good.

Jun Kwak
Maybe I should be using that more. But yeah, basically, the reason why... I mean, when we first started, we thought, there are these big wholesale marketplaces, and would it make sense for these brands to set up their own wholesale portal? The truth is, there are always buyers that are not on those marketplaces...

Jim O’Shaughnessy
Right.

Jun Kwak
...and you still want to do business with them, and that’s why you always need a direct channel. And agents make it even easier for the buyers to find, keep buying from and build relationships with these small and mid-sized brands on their direct channel as well. So I do believe in that direction, and in a sense this actually disintermediates the marketplaces that were able to build that walled garden because of the limitation of human attention, which is now gone with agents.

Jim O’Shaughnessy
And I mean, it becomes almost a philosophical question. But it seems to me that your insight is absolutely correct. Who wants to just look for information on Wikipedia? No. But I don’t, I want to be able to look as broadly as possible. But then, if we take this argument and continue advancing it, what’s going to happen to advertising, right? Is it going to become very bespoke, in terms of highly targeted to a specific thing? Is it going to go broad, right? And what happens to physical locations? What do you think? Because I’m not a mall person, but I was talking to a friend and they said, “Hey, I went to a mall the other day and it was, like, this really...” Why? But what they said was, it was a ghost town, there was nobody there. More of that? Less of that? A resurgence of, “No, damn it, I want to go store to store and do it the super inefficient way”?

Jun Kwak
I think, actually, I want to take a step back and label that as more of a sales and marketing problem that all businesses face, because which sales channel, which marketing channel has the best alpha does change over time. In a sense, brands were affected by direct-to-consumer, which was based on social media marketing, being saturated, and that actually forced a lot of these brands to change their business model. I think what’s important for these small and mid-sized brands is to be less dependent on specific channels, and be able to adapt to the different changes in purchase behaviours and sales channels. For example, we keep seeing fluctuating predictions: “Oh, would people buy more from malls and big box stores, or would they go back to local?” If you look at the headlines, it literally changes back and forth every two years.

But I think what’s important is for brands to be... and this is where, if you are running this process in-house, there’s one person who’s managing direct-to-consumer social ads and wholesale email campaigns. What we actually saw was, in November, you would start seeing these brands moving their wholesale managers to become customer support for their Shopify website, because they get a spike in their traffic. So basically, because of a lack of resources, they’re forced to sacrifice and give up certain channels depending on how things go. And I think where we can come in and help is, basically, we build out their whole department that is agnostic to these different channels, for them to be able to experiment more and find the best-matching sales channel or marketing channel.

Jim O’Shaughnessy
Do you think that there’s an opportunity for an aggregator? Like, when I was growing up, there was a magazine called Consumer Reports, right? And what they would do is test all of the washing machines or cars or whatever, and then they would say, “This one is the absolute best. This one is the best value,” right? “So it’s not as good as this top one, but for what you’re paying, this is the one you should do.” Given the way the world is going, right? Here’s a real example. Thinking about getting a ping pong table, because my grandson is very good at it. I used to be very good at it. I’d love to play with him. And so I had one of my agents go and look for ping pong tables. You know how many it came back with?

Jun Kwak
Like, if you didn’t specify...

Jim O’Shaughnessy
But then... So I specifically asked it, “Okay, look at rating systems, look at customer reviews, et cetera.” And it does seem to me that there is no single trusted source, or multiple, if you will. Is that going to be a thing? Because with agents having the ability to find every single ping pong table of this particular size, you’re going to have a sorting mechanism based on price, based on quality, based on a variety of these things.

Jun Kwak
Yeah, I think there’ll definitely be a need for verifying the source of what information is most important for any buyer. But the truth is, a lot of the brands are not even... they’re even set behind on that problem. And what happens is, if you don’t have any product information on your website that is agent-friendly, then what wins is louder blogs or Reddit articles that mention your brand. We even saw how pricing for our platform was completely wrong on Google AI Mode, because we just didn’t clarify that on our website, and there are just blogs that mentioned it, and those tend to win over your actual source of data. So this actually makes it a lot more important for brands to control what they sell and how they sell. In our storefront, there’s a big section on their pricing policies and all the brand information that brands get to directly control. Because in these marketplace entries, there’s a limitation on how much story you can tell, and all the information that you can actually put in for your products, your full catalogue.

Jim O’Shaughnessy
And how many of your brands use dynamic pricing?

Jun Kwak
So that’s actually what makes wholesale interesting. For D2C, not a lot of brands use dynamic pricing. It’s hard to maintain, it’s hard to get right. But for wholesale, the whole industry is basically built on dynamic pricing, depending on the strategic importance of the retailer. Even though it’s a very small store, if it has a very high social media presence, or it has the potential to break into the entire region, they would give a larger wholesale discount to those buyers. Same for net terms. With net terms, essentially, depending on how healthy, how big that business is, they are willing to take on more risk and give them longer net terms. So what we came to realise is that wholesale ordering and pricing needs a lot of business context.

So when we first thought, like two years ago, we thought, “Why would we even build an ordering platform? Isn’t that already solved?” But for wholesale, the pricing was the hard part, and it makes so much sense for that data to be right next to the sales data in their CRM. So that’s how we thought we had a reason to build storefronts. And essentially, how can we... Right now it is still being done in a pretty manual way. We built the software infrastructure that allows brands to specify custom discounts and custom pricing for wholesale buyers. But we’re moving to a world where we will have agents and be able to be a lot more prescriptive about, “Okay, given this retailer’s strategic value or their health, you should be giving XYZ in terms of pricing and discounts and net terms for their wholesale orders.”

Jim O’Shaughnessy
And another thing that I wonder about is, again, agents don’t have any of the problems that humans have. We need to sleep, we need to eat, we get cranky, we have bad moods, we get exuberant, we get overly excited. We do all of these things, and all of these things are basically because of our human OS, which is mostly emotionally driven, and emotions probably drive a lot of purchase decisions as well. But in a world where it’s agents, how many things that currently would be considered a premium product become a commodity?

Jun Kwak
I think that actually it will... I always use the word “amplifier” a lot when explaining agents, and same for coding, same for buying. And I think it does amplify the preferences that people have, and that’s also true for buyers making purchase decisions. So even for wholesale buyers, there are the more data-driven ones that look through the sell-through rates, and they would base their purchase behaviours on that. But there are also buyers for whom it’s more important for products to fit their overall retailer vibe, the types of products that they want, the overall atmosphere of that store. And I think that essentially agents could amplify that behaviour.

So I actually don’t think that premium products will be, like, slashed into more of a commodity. Because if that was true, I think you would live in a world where there would actually be less brands, and we would actually prefer to buy more Amazon Basics, because everything becomes... or Kirby products, because that’s essentially what people want. But I think there are always products that, in the equilibrium state, become a commodity, and there are products that require brands, or people prefer to be more branded. And I think it will just amplify both sides of the buying behaviours.

Jim O’Shaughnessy
And do you think that we will ever get to a point where the agents and the stack that you’ve built literally are able to incorporate human emotional reasons for buying, right? I have long believed that most decisions are made emotionally and then they are papered over with rational reasons for why you did it, right? Like, when I was a kid they had these infomercials on TV at night, and I used to love watching them just because of the psychology of it, more than anything else. And you could see that they were literally selling purely on emotions, right? I think it would be really interesting if the agents could in some way quantify that. Or am I just too much of a quant?

Jun Kwak
So I actually did a double major in computer science and psychology. But it’s still a tough... I don’t know the right answer to this question. But I actually do think... I still think that’s true, because if that was not the case, sales and marketing would not matter at all. And the fact that, depending on how you change your subject line, how you explain your product in our brands’ email campaigns, that actually yields different results. That is proof that, depending on how you explain and how you trigger the different emotional reactions for these buyers, it does make a difference. So I think what we’re helping is trying to make that more of a data-driven way. But essentially, I think that is still going to be true on how buyers respond to these different messages.

Jim O’Shaughnessy
I think that one of the things that I’ve given a lot of thought to is we are highly suggestible creatures, we humans. And I think that, especially the newest frontier models... I’ve been having every model since the beginning, when they called it machine learning as opposed to AI, or what does Trump want to call it? Superintelligence. I don’t think that one’s going to work. But I think that they’re going to get really good at persuasion, right? The classic text on it is Cialdini’s Influence. I don’t know whether you’ve read that or not, but we are in many respects highly suggestible. And I can see a future where you just have the AI A/B test ad infinitum. And yeah, of course some of it’s going to be like, “That was just a fluke, that’s an outlier, it doesn’t actually work.” But they’ll be able to figure that out too. And I can also envision a future where people just get so used to their agents buying necessities or basics or things like that, that it bleeds into what we currently think of as premium-type products or services. Which way do you... I’m relying on your debate.

Jun Kwak
Yeah, I’m not sure if I fully got the question. So what are the two camps here?

Jim O’Shaughnessy
The two camps are... the latest frontier models are demonstrably superior to even those of six months ago.

Jun Kwak
Right, right.

Jim O’Shaughnessy
And one of the things that I always test them on are persuasion techniques. They’re getting really good. And I could envision a future where, let’s say I’m trying to sell some premium protein powder, right? And so I have to do all of the research that says the best, and here’s why we’re the best, these independent labs, blah, blah. But I could also see having the models just A/B test different persuasion techniques till they get to the one where the person’s just smashing the buy button, right? “I need this because it’s going to solve all my problems.” As I mentioned earlier, I think a lot of our choices are emotional, and generally people buy things to solve a pain or to achieve some hoped-for outcome in terms of prestige, or their desirability, or their attractiveness, or whatever.

And so I could see one where the models just continually learn from their interactions with we humans until they get to the point where they’re just getting really good at persuasion. But I can equally see people buying basics that they don’t really care too much about. I guess we used to call these consumer staples, right? And then that bleeding into just, like, everything. “I’ll just let the agent get that for me.” Which of those paths do you think is more likely?

Jun Kwak
I see. Basically, I think there are inherently differentiated goods that require persuasion, and then there are commodities or staples where I think there is a right answer. “What is the cheapest toilet paper?” Then you can get a deterministic answer. Whereas, “What is the best couch for our apartment?” There’s no clear answer to that. In the first type of products, I think there are going to be persuasions involved. On the second side, though, I think those are going to be a lot easier for agents to go straight to the answer, and people are okay with just approving whichever cheapest product they bought for those products.

So basically, my answer is, I think it will depend on the product category. There are always going to be what we’ll call luxury goods or branded goods, where there’s a lot more taste involved. And there, I think, there is still going to be human input that is needed, both for the persuasion techniques and on the other side, for purchase behaviours. But then on the other side, for less differentiated goods, I think it will be more of the latter, where agents can actually be autopiloting and going straight to the best answer.

Jim O’Shaughnessy
And then the obvious question also becomes: how do you hack the agent?

Jun Kwak
Are you talking about the seller side or the buyer side?

Jim O’Shaughnessy
Seller side.

Jun Kwak
Seller side. So yeah, I think most of the brands that we work with... I mean, they’re called a brand for a reason. They have a niche angle, either in terms of their audience or the type of values that they represent. And these are important parts, even when we think about their sales and marketing strategy. So the part about how these agents are doing A/B testing on what’s the best strategy, that’s literally what’s happening under the hood for our lead generation services. Because basically we can keep figuring out... we can increase the temperature, try different tactics and see which one lands better.

Jim O’Shaughnessy
So I’m a huge fan of Bob Pirsig’s book Zen and the Art of Motorcycle Maintenance. And he has a story in there that has stuck with me. He rides motorcycles, obviously, and he’s riding with a friend who is driving a BMW motorcycle. And he’s very proud of the fact that he has a BMW, and something goes wrong with it. And the guy is heartbroken, because there isn’t a BMW authorised service centre for, you know, 500 miles, and what’s he going to do? And Pirsig takes a soda can top, takes the little pull circle out, fashions it and puts it on the guy’s motorcycle, fixing it, right? The guy, though, rather than being thankful, is outraged, and he’s like, “How dare you take a soda top and put it on my pristine BMW?” I wonder...

There’s also a thesis of happiness where they ask the question: what would you do if you woke up tomorrow and you were the last human being on the planet? There hasn’t been any cataclysmic problem. There wasn’t a war or anything. It’s just literally all of the other humans disappeared. Everything is as it was. So what would you do? And when they interview people about this question, in the beginning many say, “Well, you know, I’d go to the Louvre and take the Mona Lisa and put it in the palace, and I would live in the palace, and I would drive the fanciest sports car.” But then, as they continued the questioning, they found that after a while most people started saying, “Well, actually, you know, if I really was the last human, I’d probably live in a place that was very easy for me to maintain. I probably would only wear really comfortable clothes. I really wouldn’t care what I drove.” And basically the result was, many of the things that we buy or desire are to impress other people, right? I mean, it’s the whole story of the luxury goods market. And do you see agents having any effect on that sort of thing? Or am I just being too philosophical?

Jun Kwak
I mean, to be honest, when I was thinking about being the last person there, my mind went straight to... there are some Slack channels in our team where there are just agents and just me, right? Or the group chats on Rockbot where there are four agents and only one person there, and just: how do I talk there? What’s my behaviour there? My mind went straight to that point. So...

Jim O’Shaughnessy
Well, let’s answer that question. That’s a much more interesting question. Are you a different person when you are just interacting with agents?

Jun Kwak
I think that is true. Just being in those group chats where I named all the Rockbots as, you know, designer, engineer, product manager, and just talk... Yeah, definitely, how you talk, because it’s very direct. No, like, you know, words...

Jim O’Shaughnessy
No $5 words to make yourself sound smart.

Jun Kwak
And definitely no... embarrassing, but less gratitude for all the work that we’ve done. So that is true. But then, if I think about it, actually, because I’m still reviewing some of the outputs that agents produce, I am so affected by how the agents phrase the work that they’ve done, which essentially is analogous to, say, branding or persuasion techniques. But I think the biggest change for me is how I respond back. It’s very direct, very straightforward. And yeah, that’s the biggest difference.

Jim O’Shaughnessy
I think that actually could be an entirely different podcast, because, you know, I’m a huge fan of the literary fiction author Sebastian Barry. He’s an Irish guy, and a lot of his books are based on old family stories of his family. And I finished the third book in his McNulty series, called A Temporary Gentleman, and I wanted to talk about it, and all of my friends were either otherwise engaged or not around. And so I’m just like, “You know what? I’m just going to talk to my AI agent about this.” And we have a pretty cutting-edge group of agents. And I actually had, like, an amazing conversation. Because at first I said, “Hey, find the earliest reviews of this book, because I have a question about this and this,” right? And it did a great job of finding the old reviews. I think it was originally published in 2012. But then I said, “Well, what do you think?” And, like, literally, all of the training data... I was talking to a PhD in literary fiction, and I’m like, “Wow, that’s a really good point.”

And so I’m absolutely fascinated by how society in general is going to evolve, and how marketing, how brands, how all of that... I obviously can’t prophesise the future. I have ideas, but it definitely, I think, is going to change the way that people do a lot of things. Do you think that these smaller brands can survive without you guys? Meaning, “Yeah, I want to get in, I want to become a wholesale brand as well, I’m going to this agency or this marketplace.” How do they not just get totally obliterated?

Jun Kwak
Yeah, I mean, I think we got to a point where even I was trying to see if I can launch a brand for fun. And I got my fun side hustle, using Overjoy. I mean, I’m not born to be a salesperson, and I don’t know the whole sales space that well outside of how we... before working on Overjoy. But yeah, we were able to get interested buyers through our platform. I feel like, really, a lot of brand founders, some of them have sales backgrounds, but a lot of them are actually a lot more passionate about their products and getting that right. So the vision that I often have is: can we actually help them be abstracted away from all the less differentiated work on sales and back office, so that they can be a lot more focused on product building, brand building? And I think that’s basically what we are unlocking for these brands. A lot of these brands are able to run their wholesale sales process because of us, and be able to have a direct sales channel because of us. And I think that will be a lot more expensive, a lot harder for them to have us profitable. Like even note experiments to unlock that channel. Because how you start that is so expensive.

Jim O’Shaughnessy
And what do you and Alex hope for? If you could have your dream outcome, what is that?

Jun Kwak
Yeah, I think the biggest thing is: can we actually have some of the smallest brands that we have as our customers be able to scale even further, without having to worry about how... by continuing to remove those bottlenecks as they grow out this channel? So we started from getting their first interested buyers, then we moved on to getting them to the first opening order, and then making them become repeat customers. And now they’re running into new problems: how do I deal with pricing, how do I go into big box stores, all these new problems that actually come along the way. Can we keep removing the bottlenecks, so that they can scale them in a very lean way? That’s basically what we’re trying to achieve.

Jim O’Shaughnessy
And just on big box stores... I am the worst person. I’m not a shopper at all. I don’t go to big box stores. I don’t do any of that. Do they survive?

Jun Kwak
Yeah. I mean, there are some insane problems that we do encounter as we look at brands working with big box stores. I do think that there’s an advantage to coming from outside the domain and applying first principles to all the problems that we face. Because you’re looking at how these brands sell to big box stores: they come in huge quantities, they often have net terms where they don’t immediately get paid. They need to first deal with how to source that way bigger order size for these stores, and if they don’t fulfil it in time, through EDI, they get punished. There’s also a big cost for these brands to set up EDI to be able to talk to the order systems of these big box stores. And a lot of these small founders are scared to even enter that space because of that.

And then what happens is, once you are able to start selling to these big box stores, because they need to focus, they tend to give up the independent channel that they actually spent so much time nurturing and scaling. And only when they become big enough do they start seeing the value of these small retailers across the country, these, like, long-tail independents, and then they try to build the sales process again. That’s been a lot of the stories that we see in our brands. So essentially, what we are doing today is that independent channel. Because we talk to these brand founders, they’re like, “Okay, I’m chasing deals in Starbucks, I’m chasing deals with Target.” And the moment they start that, the whole profitable sales channel for independents, they just give up. And that is absolutely insane. They should not do that. So we’re basically solving that problem for these brands, so they don’t give up that sales channel. And then our goal is to be able to keep making other channels as predictable and easy to maintain as what we’ve already done for their local independents channel.

Jim O’Shaughnessy
All right, Jun. I think that you guys have done a ridiculously brilliant job. I love the way that you were like, “Oh, wait a minute, this whole service thing over here makes a lot more sense.” If you’re familiar with the podcast, you know that the final question I give to you is: I make you emperor of the world. You can’t kill anyone, you can’t put anyone in a re-education camp. But what you can do is, I’m going to hand you a magical microphone, and you could say two things into it that are going to incept the entire population of Earth. They’re going to wake up whenever their next morning is, and the two things that you say, they’re going to think they thought up, or had a dream about, or whatever. And then they’re going to resolve, “You know what? Unlike all the other times, these two ideas are two that I’m really going to work on and try to habituate in myself.” What two things would you be incepting in the world’s population?

Jun Kwak
I think my answer to that would be: one is, be ambitious. And then two, be grateful. That’s how I’ve pictured how I want my life to go. I’m going to spend a good chunk of the first chapter of my life doing the most ambitious things. But eventually I think it’s important to transition into a lot more gratitude mode, and be grateful for everything that happened to you and everything that you were able to achieve. One thing that I really like in our team, even as we are growing really fast, is every Friday we have a Friday happy hour, and we do shout-outs, and we share all the grateful things and throw shout-outs at everyone for 15 minutes. And that is always a highlight of my week. And I think it’s important to balance those two, because it’s easy to over-optimise for one of them. So being ambitious and being grateful, those are going to be my...

Jim O’Shaughnessy
I think both of those are great, especially the gratitude one. I think that people really underestimate how much they can change their own life, but also the lives of others, like your shout-outs at your happy hour. Being grateful just keeps your mind in a whole different place. I am ridiculously grateful for everything in my life, and I’m ridiculously grateful that I know people like you, and can enjoy, invest and watch you grow and do things. But also I’m just incredibly grateful that I’m alive at this juncture in human history, because I think the next 10 years are going to be a bit tumultuous, to say the least. But they’re going to be very interesting because of companies and people like you and Alex. Jun, thank you so much for being on Infinite Loops.

Jun Kwak
Thanks so much.

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Tren Griffin, author of Charlie Munger: The Complete Investor and the 25iq blog, joins us to talk about why writing a book is rarely about money, how AI is reshaping writing and publishing, why every author is really starting a business, how to build a book in public, the Charlie Munger lesson that changed his life during the dot-com boom, whether serious reading is really dying, and how to find a passion worth following.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Subscribe to The OSVerse to receive your FREE copy of The Infinite Loops Canon: 100 Timeless Books (That You Probably Haven’t Read) 👇👇

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Links

Show Notes

Tren Griffin & Jim O’Shaughnessy

• Tren Griffin: Investor, writer, and author of the 25iq blog. Read 25iq

• Charlie Munger: The Complete Investor: Tren’s book on how Munger approached investing and life. Charlie Munger: The Complete Investor

• Tren on X: Follow Tren on X

• Infinite Books: Jim’s publishing company. Infinite Books

• Tren’s earlier conversation: Welcome to the Tren-verse, Ep. 86. Watch

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned

• The Psychology of Money by Morgan Housel: Tren’s example of how stories sell nonfiction. The Psychology of Money

• Runnin’ Down a Dream by Bill Gurley: The book Tren recommends on turning passions into a career. Runnin’ Down a Dream

• Kelly criterion: The bet-sizing formula Tren calls one of the hardest ideas to explain simply. Kelly criterion

• Why Greatness Cannot Be Planned by Kenneth Stanley and Joel Lehman: Jim’s case for taking unexpected opportunities seriously. Kenneth Stanley

• 1,000 True Fans by Kevin Kelly: The essay behind Tren’s advice to build a community of super fans. 1,000 True Fans

• Duncan Watts on social influence: Why bestsellers emerge from people copying what others buy. Duncan J. Watts

• Mimetic desire: René Girard’s idea that we want what others want. Mimetic theory

• Influence by Robert Cialdini: The reciprocity principle behind Jim’s warning about manipulation. Influence

• Reflexivity: George Soros’s idea from The Alchemy of Finance, which shaped Tren’s thinking on feedback loops. Reflexivity

• Benoit Mandelbrot: Whose The (Mis)Behavior of Markets Jim credits with shaping the models he built to pick stocks. Benoit Mandelbrot

• Gödel, Escher, Bach by Douglas Hofstadter: Jim’s example of a hard book that AI could open up to more readers. Gödel, Escher, Bach

• Clarke’s third law: “Sufficiently advanced technology is indistinguishable from magic.” Clarke’s three laws

• Cabo Wabo: Sammy Hagar’s tequila, Tren’s example of a founder bringing a ready-made community to a product. Cabo Wabo

• Menlo Ventures consumer AI survey (2025): About 3% of AI users pay, in line with Tren’s point that most people use AI for free. Read the release

Highlights

If you write for money, you’re a fool.

And looking at things fresh. And then some people... it’s just hard to see sometimes when we’re not being clear. And one of the hardest things about writing is... I always love the line that if you write for money, you’re a fool. If you write to teach and share and tell stories, you’re unlikely to make much money, but you might get rich, like Morgan.

The point is, it’s a very severe power law. 20% of the authors make 97% of the money, and the top people make even more. So it’s unlikely you’re going to achieve that, but you might. But you’ll never do it if you’re in it for the money, because there won’t be any soul in your writing. There won’t be any passion in your writing, and you probably won’t say anything interesting. Some people write really well, but they’re not interesting.

People are interesting and can’t write. Some people can do both. And we are all a mix of those categories. And then as you get older, maybe you’re more interesting in some way, in terms of you can tell more real stories.

But some people tell good stories and some people don’t. Some people tell a joke and you want to sit down and sit there for the afternoon while they tell the joke. Good shaggy dog stories are fabulous. Sometimes it’s not even a very good joke, but the way they tell it is hysterical.

A good book is that way too. Like, “This is great. What’s going on here? I can’t believe this happened.” But it’s real. It’s realistic. And I always love that phrase: sometimes, if this was fiction, you wouldn’t believe it.

Don’t take the turd

I have this saying that I talk to people about, which is: you’re going through your day and some guy comes up to you and says, “Hi, you’ve been really smart. Will you help me with this problem? Here’s this turd. Will you take it?” And the answer, of course, is, “No, I’m not. It’s a very nice turd, but you keep holding that. Here are some things you might want to think about, and here are some resources, and good luck with that.” You should only take on things that you want to take on. You should take on things that make you happy and productive, but realise you’re in control. If you’re unhappy, it’s because you’re letting yourself be unhappy. No, someone else isn’t making you unhappy. You are.

Edited Transcript

Jim O’Shaughnessy
Well, hello, everyone. It’s Jim O’Shaughnessy with yet another Infinite Loops. Today I have back one of my favourite people. Tren Griffin is back. You know him from our earlier conversations. You know him from his brilliant 25iq and his wonderful book on Charlie Munger. Today, as Tren and I were chatting before coming online, we thought it would be fun to talk about all things writing, publishing, what motivates us. Tren, welcome back.

Tren Griffin
Nice to be here. It’s great to have this conversation because you are both a writer and a publisher.

Jim O’Shaughnessy
That’s right. I’m on both sides.

Tren Griffin
Goes a long way, and it helps you get perspective. All jobs are hard, as someone once said. Being a publisher is hard, and being an author is hard.

Jim O’Shaughnessy
Yeah, my kids joked, “Dad, why are you going to open a publishing company? You do realise all of the problems that publishers are facing?” And I said, “Yes, and I see a lot of solutions.” You’re writing your eighth book right now.

Tren Griffin
Yes.

Jim O’Shaughnessy
And I was rereading your 2017 essay on half a dozen lessons on getting a book published. What’s changed from then to now?

Tren Griffin
Well, the publishing industry has changed quite a bit. It’s moving from more a royalty model: you get an advance, maybe you earn it out, usually you don’t, and there was a power law. And the new model they’ve sort of adopted at many firms is, no, we’re going to treat this as a joint venture. You’re going to write this book, and we’re going to do the editing, publishing, we’ll get it out there, and then we’ll split the proceeds. And so the upside is much higher, but there’s not this guarantee. And so it appeals more to people like me who don’t write for money. Lots of books that I’ve written, I’ve just given all the money to charity. But even then, writing a book is not a way to make money.

Writing a book has many other great things. You can write a book because you want to get these ideas down. You can write a book because you want to be a mentor. You write a book because you want to leave something behind. We’ve discussed before the concept of paying it forward. A lot of people helped me. Most people who helped me are dead. And so the best thing I can do is help other people. And so if you can do those things, writing is great. And there was a period, you will recall, when blogs were huge, and now the web is shrinking, and the number of non-fiction books is shrinking. AI is competition now. There’s all of the old back titles. And so it’s harder in many ways to write a non-fiction book. That was a long answer.

Jim O’Shaughnessy
No, but it’s a good answer, because there are so many different reasons people write books. The first couple of books I wrote to help my career. That was my objective: Invest Like the Best and What Works on Wall Street. And I still maintain to this day that What Works on Wall Street in particular put me on the map and made my career possible. I think a lot of people underestimate the power of books. What do you think?

Tren Griffin
I agree with that. And then also, there are some categories, finance might be one of them, but there are some categories within finance where you’re appealing to a very small number of people and you’re educating a very small number of people. But those people are decision-makers. And so that can help you. Somebody’s got a wealth management practice, somebody’s trying to establish a fund, somebody’s trying to raise money from LPs, all those things. And so you don’t have to sell that many if you’re just doing content marketing. But if you want to sell something like The Psychology of Money by Morgan, I think I saw the other day it was 10 million, but it’s probably higher than that now. But there are people like that.

And the good news is there are people like that. The bad news is it’s probably not you, because the guy can just flat out write. And he knows how to tell stories. And people love to read stories. They don’t want to be lectured to. They like to read stories. And then the other thing is all these new formats, BookTok and Reels and all these things, YouTube: they’re short. People’s attention spans are shorter. They have other options. There are a lot of screens they can turn to. I’ve got a laptop here, I’ve got a phone right here, the TV’s over there. There’s a lot of competition, so you’ve got to stand out somehow. And that’s not easy.

Jim O’Shaughnessy
And you’re working with Harriman House, right? That’s more...

Tren Griffin
Yes, that’s part of Macmillan.

Jim O’Shaughnessy
Yeah, they are great guys.

Tren Griffin
They are. And they know business books, and that’s important, because if you’re going to get editing, you want somebody who actually understands the topic. And then distribution, getting Amazon taken care of and stocking books and doing all that, requires some work. And then the trickiest thing of all: book publishing is such a weird industry. The big titles, they don’t have a list of all their customers.

Jim O’Shaughnessy
Right.

Tren Griffin
They have a list of all the bookstores.

Jim O’Shaughnessy
Yep.

Tren Griffin
But they don’t have a list of all the customers. So direct marketing is impossible. So the first question they ask you is, “Well, what’s your book about?” And the second most important question is, “Who’s your community? How are you going to market this book? What’s your marketing plan?” It’s on you. And so the way I look at it is, you’re a publisher, so let’s talk about this for a minute. Every one of your authors is starting a business.

Jim O’Shaughnessy
Yep.

Tren Griffin
Right? He’s starting a little book publishing business, or she is. And they have to understand how to market it, how to make it cost-effective, how to create virality, what formats to use. And so they have a little business, and just that is a lot of work: building that community, keeping the community up, finding the channels to reach people, all those things. And so you’re a publisher, so let’s talk about this. Someone comes to you and says, “Well, I’ve got this idea for a book.” Do you require a proposal? How do you evaluate them? What are your standards?

Jim O’Shaughnessy
So our standards are, we’re looking for books that can, like Morgan’s, withstand the test of time. So we are shying away currently from super-current topics and looking more for books like Morgan’s, as an example. But on the marketing side, what we’re trying to do at Infinite Books is really supercharge the author’s marketing. A lot of the Big Five publishers, you get a two-week window, it gets a lot of push, and then they move on to the next project. We’re trying with continuous marketing to all of those portals that you mentioned: BookTok, Threads, Instagram, all of these social media, Twitter, but consistently. And we’re trying a bunch of different things. Everything we do is sort of AI-first.

And by that I mean we have fact-checkers, for example, that blow my mind. Literally, we have our own stack, our own hardware and software stack. And I’m currently writing a book, a fiction book actually, a first for me, and I was running one of my chapters through our AI fact-checker, and it blew me away. It was like, “Yeah, Jim, no, that tram doesn’t come in on track seven. It comes in on track nine. Here is the schedule in Polish,” because this is a generational thriller and this happens to be happening in Poland. And I’m like, holy shit. And then I looked, I have a library over here, and I just thought, all of my books that I own are filled with errors.

So we try to help the author, not only with marketing, but with everything from fact-checking to introductions to people who might be writing about his or her topic. We found that lead generation is very interesting, but you have to do it just straight up: “Here’s a book we thought you might be interested in.” And that’s it. You don’t ask them for anything. You just send them the book. And we’ve gotten a lot of good coverage that way as well. But it allows us to continually search blogs, other books, podcasts, et cetera, and then say, “Oh, wow, Tren’s book. This guy is writing about something just like Tren published in his book.” Because we have that ability to find those people, that has made a huge difference from the publisher’s end.

Tren Griffin
What’s interesting about you are many things, but one of the things, sometimes when I see your face or you have a post or something, is that I say, “Well, that’s Jim Medici.” He’s taking some of his winnings and he’s creating a Medici style... not patronage, not, right. But you’re trying to generate a lot of other good things with your capital.

Jim O’Shaughnessy
Well, thank you. And yes, I am. We talked about that last time we were together. We both believe that being generous, paying back, is something that is incumbent upon us. I was lucky enough to be born into a prominent, prosperous family. Man, I was born on third base. And then, even crazier, lucky to be born in America, where the right to free speech, the rule of law, all of these things. So I owe a lot, in my estimation, because I wouldn’t have been able to achieve any of this had I not been born in this country, had I not had the opportunities that I had. And I love reading, I love books, non-fiction, fiction, and I passionately believe that they are what allow us to advance as a species.

And so, yeah, in addition to just loving it, we also want to get good at it. So you mentioned the split with the publisher. We actually have one that goes all the way to 70% to the author, and 30% is retained by Infinite Books. Now, we can only do that because of all of the technological workflows that we have built into the process. And it’s just super exciting for me, because not only do I find many authors incredibly fascinating people, it really gives me joy to be able to bring their works and their ideas into the public.

Tren Griffin
So the conversation is lovely with a great editor, and then the conversation with your audience is even lovelier, although sometimes it’s not. And I’ve talked about this before in your post. When you create something, that’s art. A book is a form of art, literature is a form of art, and you put it out in the public, you’re saying, “Here’s my heart. I’ve put my everything into it. Go ahead and attack me.” And there are professionals. A publisher said to me once, there’s a category of people who, when the book comes out, want to be the first one on Amazon, and they’re going to give you a negative review. And that’s their whole purpose in life. And if you did a search for them, you’d find they’re doing it book after book.

Some people just want to be seen, or have attention, or whatever. But if you have a thin ego, writing a book is not a place to go. And I know some authors do not read their reviews at all, because what’s the point? For me, if I don’t like a book, I’m not going to review it. I would never write a negative book review, because these people are my brothers and sisters.

Jim O’Shaughnessy
Yep.

Tren Griffin
And I feel like they’re comrades in arms. I know what they put into it.

Jim O’Shaughnessy
Yep.

Tren Griffin
And they tried. And maybe it’s not popular, but the meaning of writing, the reason you should write, is for yourself. The book I’m writing right now is about a series of topics that I wanted to get better at explaining to other people myself. And Buffett says writing is thinking, and I agree. But also, in order to write for a broad audience, you have to find a way to simplify.

Jim O’Shaughnessy
Yep.

Tren Griffin
And to create narrative and tell stories, not just, “Well, you should do this and this, and here’s the formula for this.” We’re storytelling creatures, way before the written word.

Jim O’Shaughnessy
Oh totally.

Tren Griffin
So we love stories. And so let’s go back to The Psychology of Money. Morgan’s got great stories. The fact that thing was optioned for a movie is unbelievable. But, because it isn’t... It is believable if you know that he’s a good storyteller.

Jim O’Shaughnessy
Yeah. It’s also one of my saddest memories: I tried to hire Morgan before anyone knew who he was. He was a young guy, and I’d been reading the stuff he’d been writing, and I’m like, man, this guy can not only write, but his storytelling ability is incredible. And he was very kind to me. If you know Morgan, he’s always quite polite and kind. And he was like, “Yeah, thanks for the offer, Jim, but I’ve got a really good thing going here and I’m just going to stay the course.”

Tren Griffin
So let’s talk about the economics of publishing. There’s a lot of competition, and you’ve got all the back titles that you’ve got to deal with.

Jim O’Shaughnessy
Yep.

Tren Griffin
You’ve got self-published books, you’ve got more books coming out. You have all the fondleslab-style content. When they’re designing book covers now, they want them to look good on a phone. They have very specific things, because that’s where a lot of people buy books. And so a lot of consolidation has gone on, and it’s sort of like be big and have scale, or be small and be specialised. Is that the way you see it?

Jim O’Shaughnessy
Sort of. For example, you mentioned book covers. One thing that we do with book covers is we have artists who create them, we have AI artists who create them. We have a whole host of cover creators. But then we A/B test them. And one of the things that we found is our own judgement is often not that great, because everyone on the team, and sometimes even the author, will say, “Oh, I love this particular cover,” and then it comes in last place on the A/B testing. And then we have to go back to the author and say, “Look, it’s our job to help get your book into as many hands as possible. This particular cover scored off the charts. This one that we all love really didn’t.”

And the authors, as you mentioned earlier, we’re finding that the authors are more willing to be partners in the marketing, getting the book into hands, et cetera. But I’m an empiricist from way back. It was how I invested. It’s how I do things. And so we had one cover for a book on grief that ended up being a picture of the author and her deceased daughter. And ultimately it wasn’t the first choice, but the feedback that we got, not only from the author but from readers... we would get emails saying, “When I saw that cover, I knew I had to have this book.” Because it gets back to your idea. People want to see people’s stories. They want to hear: how did she get through that grief?

And then when you look at a picture of her and her beautiful daughter, it’s just like, I have to own this book right now. It helps that it’s a great book as well. But we try to cover every aspect on the marketing side in a continuous, ongoing way. Now, as far as economics, your question on economics: we couldn’t offer this 70/30 split if we did not have the technology underlying the book company, Infinite Books. So one of the first questions you asked that I didn’t answer: yeah, if you’re writing a non-fiction book, we’d like to see the proposal. And then what happens to the proposal is it goes through all of our evaluators, some of whom are human, some of whom are AI. We segment it to the audience.

We have pretty deeply segmented-by-audience data sets that are very helpful. And it wouldn’t surprise you, I don’t think, that many of them are based on the Big Five personality profile. Lots of really interesting tidbits as to who’s most likely to read your book that is coming out. We could tell you with a fairly high degree of accuracy what the profile of that reader looks like. So being able to take advantage of all these innovations, A, keeps our structural costs down, but also invites all sorts of marketing opportunities that, even five years ago, you couldn’t do. I mentioned earlier, we are continually scanning for other authors, people doing blogs, people making comments, et cetera.

And if we find one that is really very adjacent to what you’re talking about in your book, if we were publishing it, we’d send them a copy of your book without an ask. That’s very important. It’s just, “We think you might enjoy this. Here is a complimentary copy.” Boom, we’re done. And when you do it that way, it’s amazing how often you not only hear back from that person, but they’re like, “Yeah, I think I’m going to actually write a blog post. And thank you so much for...” In other words, it’s got to be organic. You can’t do it the old way, as far as we’re concerned: “We’d love it if you would give this particular blurb,” blah, blah. People get turned off by that.

Tren Griffin
Yeah. I think that blurbs are less important, I think. And the power of word of mouth is bigger than ever.

Jim O’Shaughnessy
Huge.

Tren Griffin
And then the whole Jeff Bezos quote about shouting doesn’t do much good anymore.

Jim O’Shaughnessy
Nope.

Tren Griffin
But it’s interesting, in that a lot of my career has been about the economics of a business. And one of the key variables is always customer acquisition cost.

Jim O’Shaughnessy
Yep.

Tren Griffin
And one of the reasons why publishers like celebrity books is because they have a cult already. They have a group of people. So when Michael Douglas writes his tell-all book, he’s going to sell a lot, because he’s already got a big fan group. He’s already got a community. He’s going to get a lot of free press. And so it reminds me of... I wrote this blog post on Sammy Hagar and how he made a lot of money on Cabo Wabo. He brought a community to this product, in this case, and that was valuable enough that, I forget who bought it, one of the big houses bought it. But the point here is getting a customer is hard. Whether you’re opening up a shoe repair store in a mall or whether you have a frontier model and you’re trying to get people to pay you. I mean, it’s wild that 97% of people who use AI pay nothing.

Jim O’Shaughnessy
I know. And what they don’t understand, at least many that I’ve spoken with, is the paying nothing gets you the free models, which, as you well know, are not the frontier models. And the difference between the models you pay for, or have in-house where your own engineers have built them to your specifications, it’s literally not even in the same country. I used to say they’re not in the same zip code. They’re not in the same country. I mentioned earlier the fact-checking that we do. That’s a very sophisticated model, which has tons of access to data and literally will pull... again, in my case, I’m writing a generational thriller. It starts in World War II and it ends sometime in the future. And it’s a story about families that are combating one another: the villain’s family and the good guy’s family.

Anyway, the ability to have access to the actual documents. So, for example, there’s another thing that I got wrong when I was writing the book, and it was having to do with a blackout in a particular town. And our fact-checker came back saying, “This works. But you might also be interested to know that the family that electrified that town actually has a house on the hill overlooking it, and they have their own internal generators running their electricity. So when the town goes into blackout, the house will still be lit up.” And so the ability to have this kind of access to not only the fact-check, but also, hey, that’s a good idea. I’m going to have that house light up in that particular chapter.

But I also think, back to basics, in non-fiction, in fiction, you are absolutely right. My friend Rory Sutherland says your average human runs on stories the way cars run on gasoline. Horses don’t run on petrol. And if you’re not getting the story right, it just really doesn’t matter. Unless you’re writing a technical book like, say, What Works on Wall Street, which I intentionally wrote in a very consistent way, so that I would say, “Here’s what we’re going to test. Here are the results. Here are the implications of those results. Moving on.” And when the book first came out, I would give speeches. And in my speeches it was all stories. And a guy came up to me at the end of one of my talks and he goes, “You can’t be the same James P. O’Shaughnessy who wrote What Works on Wall Street, because the book itself is so cut and dried.”

Tren Griffin
So in terms of your production, what’s really big, and I’ve written books for a long time, is people are doing indexes now with AI. They have their own internal tools, usually. In the old days it was like three grand to get some professional firm to create your index. I don’t know what your first book was like, but...

Jim O’Shaughnessy
Oh, yes, I remember that headache. And of course, this is back in the dark ages of the 1990s. Things were obviously, and I’m sure you experienced the same, a lot slower. But then when you got to the index and the bibliography, I remember spending literally days going line by line in both, and then you kind of lose your mind. Have you had the same experience in trying to do the indexing?

Tren Griffin
Yes. And it’s a phenomenon that I find even in writing, which is after you’ve looked at a text long enough and you’ve rewritten it, it’s hard to look at it again.

Jim O’Shaughnessy
That’s right.

Tren Griffin
Because you’ve read it so many times. So you need to go for a swim, or go catch some fish and come back, or something, and clear your mind so you can look at it with a new mind, with a fresh mind.

Jim O’Shaughnessy
And that is one of the huge advantages of having AI do the indexing. It’s not that humans aren’t looking at it. Of course we’re looking at it. But the AI doesn’t get that text blindness that we get. We’re big collectors of photography, as you know, and we would go to Paris Photo, and they have this huge exhibit with literally thousands of photographs. And both my wife and I... she’s a professional street photographer, so her eye is much better than mine. But even she, an hour and a half into us being in that huge exhibit, we look at each other and say, “We’ve got to go walk around. We’ve got to go have a coffee. We’ve got to go do something.” Because literally, you stop seeing. You really stop seeing. And it’s worse with text.

I remember when I was going through the line edits for my book How to Retire Rich, we both just looked at each other and sort of at the same time shuddered and said, “I can’t read this sentence one more time.” With AI, what we find is we have it do the line edits and then present them to the author. And it’s a lot easier if you chunk it, if the author prefers not to have them all at the same time. We’re accommodative. But it’s enormously helpful, because the AI catches things... because of what happens with our brains, we get that prose or text blindness, and it doesn’t suffer from that same problem that we humans do.

Tren Griffin
Well, the phrase I always use is that none of us have perspective on ourselves. And that’s why the importance of a community of friends is so important. So over the years, people like Michael Mauboussin, or others who I’ve interacted with, they have a way of sort of shaking you loose and making you think about things in different ways.

Jim O’Shaughnessy
Yes.

Tren Griffin
And looking at things fresh. And then some people... it’s just hard to see sometimes when we’re not being clear. And one of the hardest things about writing is... I always love the line that if you write for money, you’re a fool. If you write to teach and share and tell stories, you’re unlikely to make much money, but you might get rich, like Morgan.

Jim O’Shaughnessy
Yeah.

Tren Griffin
The point is, it’s a very severe power law. 20% of the authors make 97% of the money, and the top people make even more. So it’s unlikely you’re going to achieve that, but you might. But you’ll never do it if you’re in it for the money, because there won’t be any soul in your writing. There won’t be any passion in your writing, and you probably won’t say anything interesting. Some people write really well, but they’re not interesting.

Jim O’Shaughnessy
Right.

Tren Griffin
People are interesting and can’t write. Some people can do both. And we are all a mix of those categories. And then as you get older, maybe you’re more interesting in some way, in terms of you can tell more real stories.

Jim O’Shaughnessy
Yep.

Tren Griffin
But some people tell good stories and some people don’t. Some people tell a joke and you want to sit down and sit there for the afternoon while they tell the joke. Good shaggy dog stories are fabulous. Sometimes it’s not even a very good joke, but the way they tell it is hysterical.

Jim O’Shaughnessy
Yeah.

Tren Griffin
A good book is that way too. Like, “This is great. What’s going on here? I can’t believe this happened.”

Jim O’Shaughnessy
Yeah, yeah.

Tren Griffin
But it’s real. It’s realistic. And I always love that phrase: sometimes, if this was fiction, you wouldn’t believe it.

Jim O’Shaughnessy
Exactly. Exactly.

Tren Griffin
Right. But good storytellers... And so anyway, I encourage people to write books. I love books. I worry about the future of books. I think your mission is really good with Infinite Books, in that the industry needs help. Authors need help. Most authors are working on some side job and they’re trying to put this thing together. They’re passionate about what they’re doing. So having it more economical, having them channels, teaching them, I think is a mission, and I think it’s fabulous. If books have given enough to you, then you should try and give. I see what you bring back.

The phrase I’ve talked to people about recently is, you and I are probably the same, because when we were born, we had analogue childhoods and we had digital adulthoods. Like, 1971, the chip came out.

Jim O’Shaughnessy
Yep.

Tren Griffin
And because our childhoods were analogue, there were just a lot more books and a lot more paper. And I think books are still very advanced. They’re searchable, they’re portable, they don’t run out of batteries. All these things are great. I love paper books, and I just hope they continue, and I hope that video becomes more book-like. Blogs are a problem, because nobody really reads the web anymore.

Jim O’Shaughnessy
Yeah.

Tren Griffin
But social media is picking up on some. Long form is kind of possible on X now.

Jim O’Shaughnessy
Yep.

Tren Griffin
Anyway, it’s all evolving, but people like you with Infinite Books are trying to put a shoulder and make it a better world.

Jim O’Shaughnessy
Well, thank you. And that is intentional. So my editor-in-chief, Jimmy Soni, is a wonderful author. He’s had great success writing. And our editors, same deal: they’re all published authors. So they know. They have that passion, they have that love, they have everything that you and I love about books in their blood. And also it was very helpful for us when we were thinking about starting Infinite Books. I put the group together and I’m like, “Okay, we’re all authors. What did each of us hate about the publishing process that we went through?” And one of the things that really surprised me was a lot of the stuff that I went through back in the 90s, when I was writing my books, still happens today to these younger people. Not much has changed.

And so we took as one of our North Stars: we are fellow authors. We want our authors to succeed. We want to get that book into as many hands as possible. And so we built a lot of our practices around that. But I also want to come back to something you mentioned earlier about the passion. The same is true in so many different genres or careers. I’m an old asset manager, and I can count on both hands... it used to be one hand, but then one guy screwed it up... I can count on both hands the number of clients, when we serviced high-net-worth individuals as their asset manager, and I’m holding up my hands for our listeners, and I’m holding six, who literally said, “I did what I did because I wanted to get rich.” Everybody else, getting rich was a side event to their passion, what they did, what they loved. So it’s not just people loving to read that in books. I find it everywhere.

Tren Griffin
One of the great books that I recommended to people recently is Bill Gurley’s book about running down a dream. He has this whole formula around: look, if you structure this right, if you follow your passions, if you take these steps, maybe you can have activities that generate money someday, don’t want to call them work, that aren’t work. Like, I never worked a day in my life, because it was fun. I would have done it for nothing. Don’t tell anybody that. And so it’s true.

Jim O’Shaughnessy
It’s absolutely true. I would have done what I did for nothing, just because I wanted it.

Tren Griffin
Some people fell into it accidentally: “I just happened to love this. I followed it, and I got rich.”

Jim O’Shaughnessy
Yeah.

Tren Griffin
Andy Warhol or somebody, whatever it was. But some people are much more purposeful about it. Gurley’s book is about: find the best mentors in the world, physically go where they are, interact with them, learn from them. The Charlie Munger idea that you don’t have to figure out everything by yourself. Learn from the greats. And then find your own passion, all these things. But the important thing is, don’t lead a life that’s completely determined by chance.

Jim O’Shaughnessy
Right.

Tren Griffin
Be active in terms of figuring out: this is the right path, this will help me. I should write a book now. I shouldn’t write a book now. I should focus on this. Some purposefulness, and learning from others, is just so much more efficient.

Jim O’Shaughnessy
Yeah.

Tren Griffin
There’s another Munger quote, which is just like, it’s just so efficient to read the greats, to understand the greats. And then also, I had this analogy, I’ve talked to you about it before, which is: life is like going to a grocery store, Trader Joe’s or Whole Foods or someplace, and you’re walking down the aisles. And when you’re young, you say, “Oh, I want to be this way. And this is the way I want to deal with work, and this is the way I want to deal with romantic partners. This is the way I want to deal with physical exercise. This is the way I want to deal with eating.” And then as life goes on, you’re still walking around these aisles, and you can say, “Well, I’d kind of like to change it for this one, because I’m not as interested in this anymore. Or this is bigger, I can even get a couple more of these.”

And so you’re constantly doing this opportunity cost analysis and saying, “Okay, well, this person’s cool. I love everything they do, except only about four-fifths of it. The other fifth, I don’t want to be that way at all.” They’re an anti-model.

Jim O’Shaughnessy
Right.

Tren Griffin
But you can be whoever you want, and you can always change, if you’re that kind of person. I’ve always wanted to be someone who could change.

Jim O’Shaughnessy
As have I. And the thing that shocked me, especially when I was younger, was the number of people who don’t want to change. There’s no part of me that groks that. Like, you have...

Tren Griffin
Some of that, I think, is inherent. It’s genetic. You come out of the womb. They talk about the little baby in a crib, and you go up to the baby and go... and somebody goes, “Oh, that’s cool. What’s going on?” Some of them go, “Oh God, no.” And some of it is genetic, but some of it is pattern matching, which is if you’re around people like Feynman or somebody like that, who are super interesting and polymaths and interested in multiple disciplines and play the bongos, whatever it is, you say, “Well, that sounds fun. Why wouldn’t I want to be like that? Why would I want to be like a guy sitting on the couch, the Barcalounger, watching the latest NFL highlights?” It’s just not... But again, some of it’s genetic, some of it’s innate.

Jim O’Shaughnessy
Yeah.

Tren Griffin
You can train yourself.

Jim O’Shaughnessy
I agree. You absolutely can train yourself. And I want to ask you about the Munger book, because you started out writing that just for yourself, which I thought was super cool.

Tren Griffin
Yeah. It was also a tribute, in that during the internet boom, things were crazy, and I was worth a lot of money on paper, and I had to make a decision about secondary sales.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And how much of my existing portfolio I was going to keep in Qualcomm and a couple of other names. And I went up to the San Juans in a boat. Had a skipper. My family was downstairs. I was upstairs. I just thought and paced, walking back and forth. Eventually I used his principles, because most of what I read was leading to his ideas. And I realised that you only have to get rich once. This is a key idea.

Jim O’Shaughnessy
Yep.

Tren Griffin
Second of the ideas: you have to survive. You don’t want to get in a situation where you have it all on red. And then you’ve got the whole Kelly optimisation and all of that. And he doesn’t really use Kelly, but he’s talked about that, because it’s kind of what he does. And then talking about how markets can correct 50%: “It’s happened to me three times,” he says in a BBC interview. So anyway, as a result of that, I sold half of my internet and telecom stuff and it went to cash, and I was able to get more out after that. But that changed my life. It just... you relax, your sphincter relaxes, and...

Jim O’Shaughnessy
But what did you have to change when you decided you were going to publish the book for other people to read it?

Tren Griffin
Nothing really, because I wrote the book for me, and as a tribute: this is what you gave to me. Which is another way of thinking, by the way. We don’t agree on everything. People say, “Oh, you wrote this Munger book. You must think he walks on water.” No, I didn’t agree with him on China. There’s a bunch of things I don’t agree with him about.

Jim O’Shaughnessy
Yep.

Tren Griffin
But I like the way the man thinks. And so that, to me, is the important thing. So really, I tried to make it maybe a little simpler. I guess that’s the thing I did do. The hardest thing is to simplify. Let’s see, the Kelly criterion: writing about that simply is not easy.

Jim O’Shaughnessy
No.

Tren Griffin
Right? And the difference between log and geometric wealth, and getting all that, but making it simple and in a story, that’s not an easy thing. But if you can teach it easily, you’ll reach a lot more people and you’ll help them, because they’ll say, “Okay, I kind of get that. I want to learn more.” And then they go dig in someplace else, or whatever. But simplifying complex things is the one thing that I did. But he does that anyway, and he does it in a funny way. And one thing about writing a book is: write about something interesting. I picked a pretty good topic. I knew a lot of people who knew him, who interacted with him. And so if you pick a good topic, you can do a lot better.

If you’re going to pick the nematode worm in Gambia in the 1500s, you’re not going to get quite as many... And then the thing is, comedy is truth. And he’s always funny, because he’d always say things out loud that everybody knew were true, but he’s saying it out loud. “I can’t believe Munger said that at the Daily Journal meeting. That was unbelievable.” But he doesn’t care.

Jim O’Shaughnessy
I always remember Billy Wilder saying, “If you’re going to tell the truth, you better be funny, or they’ll kill you.”

Tren Griffin
Yes, exactly. And be somewhat humble about it, because if you’re arrogant, people think, “Oh, what an asshole.” Whereas... sorry.

Jim O’Shaughnessy
Swearing is allowed on this podcast, remember?

Tren Griffin
You know what I’m saying? You have to be interesting or people will... There’s a lot of competing things for your attention.

Jim O’Shaughnessy
Totally.

Tren Griffin
And you have to be interesting, and it’s got to be understandable. It’s got to be simple. But you should have passion for it, and you should be writing it for you. Because the more you write it for yourself, the more likely it is to be a success, in my view. Because it’ll be true to you. And the reader will pick up and say, “Wow, that’s something this person really believes.” And I don’t care if they agree with me. I want them to think about the issue.

Jim O’Shaughnessy
Exactly. And I want to go a little deeper on the curse of knowledge and simplifying. I suffered with that, trying to make what are very complex topics simple enough that everybody could grasp, okay, this is the way it works. That ain’t easy. It’s really hard. But it also gets back to: writing teaches you whether you know something or not. I’m an inveterate journal keeper, and I’ve been doing it for 45-plus years. And the amount that it has helped me understand... like, when I’m writing about something, then I look up and I realise, oh, I don’t know about this. But then it spurs you on, because, okay, I need to learn better. I need to be able to synthesise, get this easier to understand.

You are really good at that, with the profiles you do at 25iq, et cetera. Tell us your secret. How do others who want to get that good... what could they do to improve their ability to synthesise information?

Tren Griffin
Well, first of all, you have to read everything that the person has said and written, and try and sort of set yourself in their shoes. And then it helps to understand their history. Ken Griffin, for example, had a rough period, and he learned a lot. It was rough by many people’s standards, a period of underperformance. And you sort of learn. And then, to your point, if you can’t write it down, you haven’t thought it through.

Jim O’Shaughnessy
That’s right.

Tren Griffin
Starting to write it down, you sort of say, “Okay, well, I really don’t understand this as well as I could have.” Going back to the Kelly criterion, or explaining something like that. And it’s just trying to be empathetic. And then eventually other people can read this book. Nobody’s going to read it until I send it to the publisher, and I’ll get some feedback, and that’ll be good. And there are people who think about these issues harder than I do. But I have my own style. I’m not going to adopt their style. I sort of want to be interesting and amusing. In the Munger book, I’ve got six jokes. I’ve got four jokes in my current book. And they’ll probably get cut out by the editors, but at least there are some jokes in there.

You sort of have to mix it up, and you don’t want to be boring. Don’t be boring. It’s deadly. And plus, being boring is not fun. It’s much more interesting... And you’re going to take some arrows. There’s going to be incoming. Any artist, someone creates some lovely painting like the one behind you, and someone will say, “Oh, I don’t like that. It’s too much like so-and-so,” or, “Look at this brushwork,” or whatever the hell that is. Yeah, it’s just negative, and you’re going to have that. That’s fine. In some sense, it can be good publicity. But don’t be boring.

Jim O’Shaughnessy
Yeah, I agree. And one of the things that I got very good at... when I read the first review of my first book that was negative, I will admit to you, I was 30-whatever years old, I was crushed. I was literally crushed. And then I read it again, and I read it again, and then I realised he actually doesn’t understand this topic at all, and that’s why maybe I frustrated him, or whatever. And so I became not immune to getting attacked, but my skin thickened up considerably. Now, have you found that there are some very critical reviews that have actually improved the way you think about something, the way you write about it the next time you write about it? Because I have had that experience as well.

Tren Griffin
So what I like is a dialogue. Someone will say, “Well, I read your Munger book and you talked about this. My interpretation is different.” And then we have this conversation, and that dialogue tends to be good. It can be even great, because it forces you to explain things simply. I always had this conversation with this person, and I was trying to explain to them about wealth increasing geometrically as opposed to arithmetically. And it’s not intuitive.

Jim O’Shaughnessy
No.

Tren Griffin
People say, “Well...” And so getting that across simply requires some work. So having the dialogue is best.

And then also the reviews of people who I trust, who read the book before it’s published. I get the most out of that, because in that situation they’re not afraid to say, “Well, this is messed up. You need to fix this, or do this,” or whatever. And sometimes it’s good and sometimes it isn’t. I know some people like Morgan probably don’t need to get a lot of external advice, but I like that phase where I’m getting pushback. But then also, sometimes there’s no great answer. And so you’re doing complex adaptive systems and a whole range of things that mean, well, that might have been a good answer a long time ago, but it isn’t true right now.

And it’s like this whole debate about: is passive share changing active? Everybody has an opinion on that, just like they have a belly button. They’re all different, they’re all slightly different. Some are very different. But the point is, some things are opinions, and you can agree to disagree, because it’s opinion; you can’t prove it. And also it’s early. Some things are non-linear, some things aren’t. Some things come out of nowhere. It’s like they were working on AI, machine learning then, and they created this thing that could make translation better, and they scaled it up and it started to do more than that. It started to be capable of producing things that kind of seemed like it understood reasoning, and it got better. But it came out of nowhere. I mean, this whole AI thing is not long. And so, to me, this feels like when the internet first arrived. It feels like 1993, the commercial internet. Movement before that, but the US said, finally, okay, you can sell things on the internet. That’s when it changed.

Jim O’Shaughnessy
And you and I are entirely simpatico on that. I think that the AI revolution... I’ve been interested in it since it was called machine learning, and I’ve always been fascinated by it. But I agree with you. I think that this is a sea change, not only in society, but in the way businesses are organised, in the way people do publishing, the way people do media, and the way people do investing. My version is: what a time to be alive. I am so lucky that I am around for this innovation, because we are at such early stages of where this might take us. And to me, literally, I get giddy, because the ability to use the leverage that these tools allow is just extraordinary.

If I fell through a time tunnel back to when I got married, 1982, and somebody had an iPhone... first off, I’d be freaked out about the iPhone. But then imagine them running a large language model on it. Can you imagine? It would just seem like... what did Arthur C. Clarke say? “Any sufficiently advanced technology is indistinguishable from magic.” And to me, it’s just intoxicating, all of the new things that we can do and make better with these new tools. Now, I’m not naive. All tech, in my opinion, is dual use. Fire: great example, great tech. First, when we started cooking our food, that helped us develop our executive function, our prefrontal cortex. Very nice for us as humans to have. But fire is also incredibly dangerous.

And so we didn’t ban it. We had fire alarms, fire departments, fire exits, fire extinguishers. And I think that we’re going to have to do the same thing with this new technology. But I definitely think that we are looking at what is going to be just an extraordinary, tumultuous decade or two going forward, because of the innovations and the ability to do things that would have been inconceivable just 10 years ago. To me, it’s just like, okay, we’ve got to rethink all of our business models. We’ve got to rethink our playbooks. I don’t know if you’re a fan of Ken Stanley’s Greatness Can’t Be Planned, but I love that book, because, and you alluded to it earlier, nothing is binary. I either love Charlie Munger or I hate Charlie Munger? That’s bullshit. There’s a lot of things about Charlie Munger. I love the guy. I think he was just such an amazing human being. But, like you, does that mean that I think he was right about China? No, I think he was totally wrong. That doesn’t reduce my admiration for him as a human being. It’s just that, okay, you’re not going to always agree with everything.

But the ability to pivot, back to Ken Stanley: a lot of things come completely unexpectedly. And if you want to increase the surface area of your luck, you better take those things seriously. When you notice, “Oh, look at what I can do with this new fact-checking workflow. Wow, that’s going to be very helpful.” Plagiarism, for example. Let’s hope we never have to face that again, because it’s literally trivial for us to run a manuscript through our AI and contrast and compare it with hundreds of thousands of other ones to see if... Because there’s a thing in backtesting for quants called honest data mining. You’re not intentionally trying to mine the data. But we had the old quote that when you torture the data long enough, it will confess to anything. And so they’re not doing it intentionally to data-mine. The same thing happens a lot in writing. People who are really good writers, guess what? They’re also really big readers, and they might take notes about books that they’ve read. They might just have great memories.

And when they’re writing about a subject, they could completely unconsciously channel something that they read from letters long ago. So with the new tools, when we find that, they’re like, “Oh my God, that isn’t what I meant.” And obviously it gets changed. But there’s just so much that I think this is going to bring to us as a culture that I just find super exciting.

Tren Griffin
One of the things that’s interesting related to that is, if you look at SpaceX, they’re really vertically integrated. They make a lot of things themselves: steel, cast things. I think writing is that way too, in that people that are doing self-publishing, and some people do really well at it, make a living at it, they’re doing the whole stack.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And all these new tools allow them to do the whole stack. And so you get the ability for people to get noticed, maybe with their first book; people to have a niche indie hit; people that make a living doing what they love. It’s not a great living, but it’s a living. The vertical tools enable you to sort of unbundle this whole stack. And if you can’t get to a Big Five publisher, maybe your first book will be self-published, and the next one will be a small press, and then maybe you’ll be a big press, or maybe you’re just happy with a small press. Certainly you want somebody who cares about your book as your publisher.

Jim O’Shaughnessy
Yes.

Tren Griffin
And the bigger your publisher, the more likely it is to be, “Well, we’ve got six celebrity books on for fall 2027, and yours is in the mix.” Whereas it’s nice to be the big dog. I had this success with the Munger book, and to be a big dog, and I’ve sold some books, and success reinforces itself. Unfortunately, there’s a feedback loop, and success breeds more success.

Jim O’Shaughnessy
Yep.

Tren Griffin
And it’s sort of one of the questions: why is there a power law? Why do books have a power law? And Duncan Watts has this great essay, but basically he points out that humans don’t make decisions independently. The books we buy are the books that we see that other people have. “What’s on his bookshelf? Oh, he’s got that book. Oh, she’s reading this. Oh, she’s doing this.” And so you tend to buy that book, and that whole thing cascades until it stops. And it can stop pretty quickly. But the point is, how do you get that started? How do you bootstrap that? It’s tricky, but there are ways to do it, low-cost ways to do it.

Jim O’Shaughnessy
And you’re absolutely right about momentum. I think that the whole Girardian idea of mimetic desire absolutely plays in. And by the way, it’s not just books. It’s everything. It’s art, it’s movies, it’s any form of media. And that’s why that word of mouth is so important. Because, as you have rightly pointed out, attention now is truly the most precious commodity. And people have so many options that they can elect to either ignore, or they can read every particular book, et cetera. So finding those readers is really important. Your publisher urged you and encouraged you to develop the book in public. Tell me exactly what that entails.

Tren Griffin
Well, usually they don’t want you revealing the title or any of the content until about eight months before.

Jim O’Shaughnessy
Right.

Tren Griffin
And the way it works is, in the spring they said, “Let’s go. Give it to us at the end of November, and it’ll be out the following November.” They’re like baseball managers. They’ve got a lineup; you’ve got to get in the lineup. You’re going to be a Christmas book and all that. And so you have to phase it. But building your book in public is super important, because even before you announce the title or whatever, you’re building the community.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And you can do that on social media. You can do that with other kinds of speaking, doing events. But pre-sale is really important, and early word of mouth is really important. And the more they see early sales, the more they’re going to lean into it, and the more distributors are going to want to move it, and things like that. So you really have every incentive to build the community way out, even before you reveal the title and all that. Kevin Kelly’s got this: everybody needs a thousand fans. I don’t think a thousand is enough. But if they were superfans, maybe. I know on your OnlyFans you probably have, what, a couple, 10,000? But they’re very passionate about you, Jim, and you fit their profile. So my hat’s off to you. Although in that last OnlyFans, you weren’t even wearing a hat. Come on.

Jim O’Shaughnessy
Anyway, now I’m going to have to start promoting my OnlyFans channel, which is completely, as you well know, non-existent. But seriously, how would you suggest... let’s say you and I had to put our heads together. We found a really bright young non-fiction author. You and I both agree: “Wow, this is an amazing book.” How would we go about it, other than the obvious? Obviously I’d have him on the podcast, I’d suggest him to other podcasters, I would send his book around to people that I know are interested in that particular topic, all of that. But what advice do you think you and I could craft together to tell this young man or woman, “Here’s what we really think you need to do, because your book is amazing”? Let’s take that as a given. Even amazing books that don’t get marketed right to the public die.

Tren Griffin
So the key thing is, the cost of creating a book is high, but the cost of making it and distributing it and publicising it has never been lower. It’s almost zero.

Jim O’Shaughnessy
Exactly right.

Tren Griffin
And so what the publisher is saying when they tell their authors to do this is, you need to get out in these channels where it’s essentially a freemium model, which we call it in the SaaS business: you’ve got to find channels where you’re giving your stuff away, but you’re not giving it all away. So Substack is actually sort of a great example of that, where so many authors have, I don’t know, nine paragraphs or eight paragraphs, and they’re leading you into a conclusion, and then, “Oh, beyond this point...” But that’s good marketing. And so because it’s zero cost to you... not zero cost, but very low marginal cost.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And so you have to sort of build this passionate group of fans who hopefully are going to say to their friends, “Hey, you should buy this book, too.” One of the funny stories I tell is, I’ll go to someone’s house and I’ll see their bookshelf, and I’ll say, “Wow, cool bookshelf. I’ve always wanted to read that book.” And I’ll pull it out and I’ll open it up, and it’s got that crackling sound of a book that’s never been opened before.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And unfortunately, there’s a modern phenomenon, which is people buy books to make a statement.

Jim O’Shaughnessy
I know.

Tren Griffin
And to some extent, I swear, some of them think that if they bought it, that’s good enough, because I’ve got it on the shelf.

Jim O’Shaughnessy
Do you remember the meme with the little Chinese boy going like this on the book, and then going like this on his face? It doesn’t work that way.

Tren Griffin
No, it doesn’t work that way. But some people think that way, or some people would like to think they read that much. Look, it requires effort and time. You have to set aside time to do it. It’s like writing. I believe that if you’re going to write, really, you should have a period of time where you set aside a couple of hours, completely lock everything out, and you go at it and you think and you go at it. Not, “I’ve got 10 minutes here, I’ll try and do something.” You can do a little research that way.

Jim O’Shaughnessy
Yeah.

Tren Griffin
Like, “Oh, I’m waiting for my pills at the pharmacy,” or whatever the heck it is. “I’ve got a cold and Dr Meck did this. I’ve got 10 minutes. Oh, I always wondered about that.”

Jim O’Shaughnessy
Yeah.

Tren Griffin
There are all these little moments. Like, I always wondered why the mustard packets in Chinese takeout food taste so good versus the jarred mustard. And actually... so, yeah, it’s so fabulous. You go in and it’ll tell you why it is. Well, there’s a reaction, and it won’t last, and you can’t replicate that in a jar. Once it’s aerated, it gets ruined. So you should buy some powder and make your own. So now I make my own. But the point is, if you’ve got 10 minutes, you can go research some point in your book, and then you can go deeper and deeper. And you’ve got five engines you can talk to. Most of the engines now are focused on coding, because that’s what pays.

But for purposes of just, “Who said this, and when?” or, “I remember Michael Mauboussin said this in an essay called this. Find it for me. Give me a link.” I don’t use Google. I don’t use the search engine anymore for that.

Jim O’Shaughnessy
Same with me. Everything I find now is through our AI system, because it finds exactly what I’m looking for. And this is one of the things that I’m now questioning my own statements about. I used to say that I was lucky when I came up, because I have an unusual memory, in that if I read something, I can remember it pretty well. But only if I read it. If I see it in a movie or I hear it, my memory is not that great. But if I do read it... it’s maybe one of the reasons why I read so voraciously. But I started to think that my memory back then was a huge advantage for me, because people didn’t have that similar recall. And then I thought, “Well, you know what? In the age of AI and large language models, my memory advantage is going to plummet, because they’re just going to be able to go to their phone and say, ‘Tell me about,’ fill in the blank, Robespierre, and get a pretty good biography, or their specific question answered.” But then I started thinking about the fact that the memory still gives me access to things that other people have never experienced.

Tren Griffin
Your prompts are better.

Jim O’Shaughnessy
Exactly. Yeah, exactly.

Tren Griffin
You have to know a lot to be good at prompting. And so it’s really leverage.

Jim O’Shaughnessy
Yes.

Tren Griffin
Because if you don’t know what to ask... and you have to find out. Now, it’s not always right. The answer’s got hallucination in it. And so you have to be able to smell something: “I’m going to ask another engine, or I’m going to read source material.” I still have a huge paper library. I have tons of books; I go into them all the time. But you have to be able to tell when it’s wrong, but also to ask. The key thing is you’re a better prompter.

Jim O’Shaughnessy
Yeah. And I think that will continue to persist. And one of my worries is, everyone’s decrying, “Oh, reading is plummeting. No one’s reading long form anymore.” And I wonder if I buy that. And by that I mean, listen, I think that 50 years ago, probably a similar amount, of what I would call very serious book readers. Okay? And I’m being very specific about that, because 50 years ago, most people read the newspaper, most people read magazines, et cetera. But if we focus in on the group of what I would call serious book readers, do you think that has literally changed all that much from then to now?

Tren Griffin
I think something has changed, in that, like, in 1993 I get introduced to Bill Gurley and Michael Mauboussin on the same day, by a guy named Michael Larson, who’s a big fund manager. One of the biggest. And they got me interested in what they were doing down there, and I said, “Oh...” And then I said, “I’ve got to know more,” and I figured out Mandelbrot. And then Michael Larson said, “Well, you should read Alchemy of Finance by Soros,” which is a very hard book to read.

Jim O’Shaughnessy
Oh, no kidding?

Tren Griffin
Yeah. But if you come at it a layer up, it becomes an important book which leads you other places. And so those two books... Mandelbrot has a book that’s particularly good, and Alchemy of Finance, they just lead you to other places. And so I probably had more time to sort of focus on that book when I was reading Alchemy of Finance. I wonder what I’d do reading it today, whether I’d be patient enough to work all the way through it and then think about it hard, because there are so many other competing things.

Jim O’Shaughnessy
Yeah.

Tren Griffin
But it was pretty seminal for me in terms of thinking about feedback loops and increasing returns and Brian Arthur and network effects, and it just sort of leads you on a path. So I probably seldom put as much effort as I did in the 90s and 80s into that one book, really digging into Mandelbrot, really digging into Taleb’s books, or whatever it was, because there are more distractions. But I think I’m reading more, and I think most of it is supplementary. I’m still reading as many books.

Jim O’Shaughnessy
Yep.

Tren Griffin
I’m just also reading more stuff. The how-to stuff is amazing, for fishing: flies to choose, where to fish, what time to fish, all things like that. Now, AI is fabulous on that, and it can be very local. Like, where are the chum salmon going to be hottest in a week in Hood Canal? It’ll tell you. It’s great. So I’m reading more than ever. I’m reading more than ever. But I like thinking. Not everybody likes to think. Some people want to get home and not think: “I don’t want to think anymore. I’ve been thinking all day.” But to me, it’s better than sex. No, it isn’t. But it’s darn good. It’s darn good.

It’s not as good as your OnlyFans, Jim, but...

Jim O’Shaughnessy
Now, you know, as a result of this, people are going to go look for my OnlyFans account, which does not exist.

Tren Griffin
Maybe you’ve got a... what do you call it, doppelganger out there?

Jim O’Shaughnessy
Doppelganger. Yeah.

Tren Griffin
Yes, exactly. Maybe they’ll find something. Maybe they’ll find purpose.

Jim O’Shaughnessy
Yeah. Finally, finally I will find my true purpose in life, and that is an OnlyFans account. I think, though, that you’re exactly right about the idea that a lot of us who were serious readers to begin with are reading a lot more. I am. Now, granted, that’s because I’m a publisher and I want to give the manuscripts that are submitted their proper attention. But my idea is a little different, in that I think that the percentage of people who were what I call very serious readers was very similar back in 1950 as it is today. By this, I mean we’re back to power laws. There is always going to be that group. They’re different people, but they’re still very serious readers. And I think that has not changed.

I think when we look at various marketing surveys, et cetera, the percentage of people who read the most books is a power law. Literally... I don’t have the graph right in front of me, but there’s the big majority that don’t read any books at all. And it’s not a big majority, actually. Let me rephrase that. But then it steps up to the top of that heap, which reads some ridiculous amount of books every year. And I just think what’s happening is the group of people that belongs to that category has just changed. I mean, you and I are still around, but there’s a bunch of young people in that category who weren’t even born when we started our reading adventures. And they have taken to reading in much the same way we did.

Now, did they do it exactly the same? Do they have the same paper book that we had, or the way we took notes? Do they have to go to the library like you and I had to? No, but they’re still reading. And so I’m very optimistic that with a lot of the new innovations, a lot of people who, for whatever reason... you mentioned people don’t like to think. I can’t remember who...

Tren Griffin
Some people. I said some people don’t like to think. They want to get... people watch a game and not think.

Jim O’Shaughnessy
Yeah. There’s that great philosopher who said that people would rather rearrange their prejudices and call it thinking. And I think that there’s some truth to that. But I definitely think... let’s take a crazy book, like Gödel, Escher, Bach. Kind of like Soros’s book. Oh my God. I don’t know if you’ve read it. I’ve read it, but it was unbelievably hard to read that book. And a lot of people avoid that book. Same with Mandelbrot’s (Mis)Behavior of Markets. I thought that was an incredibly brilliant book. It unlocked a lot of insights for me about the way I actually built the models that I built to select securities.

But I think that there is a chance that the technology could actually allow a path into Gödel, Escher, Bach that wasn’t present before. By that, I mean, how cool would it be to have an AI right there as you’re reading Gödel, Escher, Bach that you could immediately ask, “Hey, what’s this three-body problem? Hey, I never heard about Agrippa’s trilemma. Can you explain it to me like I’m five?” And I don’t mean to belittle that; I often use that prompt: “Explain it to me like I’m one of my grandchildren.” I think that could bring in a lot of people who are right on the edge of, “Maybe I should really read that book. I think I could really benefit from it.” What do you think?

Tren Griffin
One thing I like is to say, do a complicated answer. “Okay, I’ve just read that. Thanks. Give it to me as a narrative, as a simple narrative, and include a story if you can.”

Jim O’Shaughnessy
Yep.

Tren Griffin
And so reducing it down to its essential components often helps. But it’s also much more interesting to read about something where you’ve already done something where it’s applicable.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And so you start to invest, and you say, “Wow, Mandelbrot’s ideas are... I read about those, and they’re interesting. I’m going to go deeper into that.” And then that leads you to Taleb, that leads you to Ed Thorp, and then a whole range of things, and it becomes a treasure hunt.

Jim O’Shaughnessy
Yeah.

Tren Griffin
To get to the truth. And then everybody has slightly different views. It’s like Zeckhauser and Taleb don’t agree on these issues, but they agree on these issues. And then you have to form your own opinion. You have to dig into it. What are the various arguments on either side, and is there someplace where they meet in the middle? But the ability to do self-exploration is amazing. When I was in the second grade, I used to ask so many questions of my teachers. They’d say, “Tren, you should go down and help Mrs Salverson in the library, because there are books down there and you can help her put them away and read for a while.” It’s like, “Stop asking me so many questions.”

But some of us, you can’t stop asking questions. Why? You catch a strange fish: “What kind of fish is this? What do they eat? Where do they swim? Does it taste good? Does it have mercury in it? Does it migrate? Is it sustainable?” And some people don’t want to know: “Tren, it’s just a fish.” Well, no, I want to know. I want to know more. I want to know more. There’s no end to it. So much fun.

Jim O’Shaughnessy
It’s Dorothy Parker’s great quip, that “reading is a cure for curiosity. There is no cure for curiosity.” But here’s what I’d like your advice on. How would you inspire somebody to be curious? Because I think, like the fellow you mentioned who just wants to go home and watch the game, for whatever reason... what if you were going to run a course on how to increase your curiosity? What would the syllabus look like?

Tren Griffin
I think the first thing is you sort of have to identify the passion first, because everything flows from that.

Jim O’Shaughnessy
Yeah.

Tren Griffin
The reason why the person is coming home and watching the game is they haven’t discovered that they have a passion for fly fishing, or fixing their car, or reading books, or appreciating art, or appreciating nature, or being a bird watcher, or being a fly fisherman. Whatever it is. You can’t fake passion. So you’ve got to try a bunch of things, and then once you find it, then you have to dig in. And the great thing is, the more you know that you don’t know very much yet.

Jim O’Shaughnessy
Oh, no kidding.

Tren Griffin
And there’s no end to it. And then eventually you get to this question, you go all the way down to what’s written, you get, “Well, why is there something instead of nothing?” And then you get into quantum physics, and then you’re like, “How did I get here?” Well, it’s because you’re following the string. But you’ll follow a string if it’s interesting, if it’s relevant, if you have some passion about it. And some people just haven’t found their passion. And that’s why I like Gurley’s idea of finding your passion early in life.

Jim O’Shaughnessy
Yeah.

Tren Griffin
Because you tell the story about writing your book... I think you were 27 or something for your first book. You have nothing to lose when you have nothing to lose. It’s like a venture capitalist: all you can lose is what you put into it. Well, if you write a book, all you can lose is the energy you put into it and the time you put into it, and you’ve learned during the process. But as you get older, it becomes harder, because your opportunity cost gets harder. And so that’s why I consciously say, “I’m going to do these things that are consulting, because it keeps me around interesting people, and it generates some revenue, and it’s nice. I’ll do these things which are paying it forward.” And I’m going to cordon those off.

And I’ll always give it the time it deserves. And that can happen in a lot of ways, including one-on-one mentoring with people. Just learning about things just to learn about them, that I’ll never be able to use or monetise. I just want to know. I want to learn. I want to know. So anyway, it all starts with passion, is my answer. And then you go from there. You can’t fake passion. But you don’t like sitting on the couch.

Jim O’Shaughnessy
No.

Tren Griffin
You’re going out, trying all kinds of shit. Like, “Oh, you like bird watching? Come with me one time.” You might get hooked. You might not. And then you might say, “Well, I don’t like bird watching, but I sure like looking at sunsets and scenery and all that. Maybe I’ll be a photographer.” At least one thing leads to another. I like to read obituaries. And one of the reasons I like it is because you have these great stories: “While he was at college at MIT, he met this guy, and he was selling rugs, and he moved to Afghanistan, and he sold rugs for a while, and then he shipped them, and then he became a wholesaler. And then he moved to Thailand, and then he did this, and then he bought a bank.” And it’s sort of like, wow, that’s a life. My goal in life is to be able to tell great stories that I’m in, that I’m a character in, because that’s a test. It’s going to be interesting. Shit’s going to go on. It’s crazy. It’s boring to be boring, let’s put it that way. Lighten it up. Light it up. Try something.

Jim O’Shaughnessy
I could not agree more. I had a friend a while back say to me, he looked at me and he goes, “You know, I deeply suspect that everything you’ve done was just for the stories.” I’m like, “Well, what else is there?”

Tren Griffin
But it’s also a great test, which is someone says, “Well, you should come do this,” and you think, “Wow, that’s going to be great. And now I have a great story out of it.” Because if it isn’t material for a great story, it was boring. You didn’t do it interesting. We were out and the weather got bad and the ship was getting tossed, and if not for the courage of the fearless crew, the Minnow would be lost.

Jim O’Shaughnessy
Would be lost.

Tren Griffin
All these things. That’s an adventure. You learned. How did the Professor make a radio out of a coconut? All these things. Maybe I should investigate. No, just kidding on that one. He used to live very close to me, and I asked him that once in the grocery store: “You really couldn’t fix the Minnow, but you’ve made a radio out of a coconut? How did that work?” He didn’t think that was very funny. He’s passed.

Jim O’Shaughnessy
I think it’s hysterical. But both you and I had early experiences. Yours was actually earlier than mine. I was a teenager, and I was listening to my uncles and aunts argue about an investment. And it was one of the first times I got to sit with the adults, when they all had gathered. And so I was trying to be on my best behaviour, and I was listening to my dad and my uncle argue about IBM, I think it was. And I just remember thinking, “I think that’s the worst way to think about a stock.” And I remember your story about when you were six years old on your grandfather’s 45-foot Chris-Craft boat. You were listening to them talking about business and about buying hotels and all of that.

What was something that, when you were six, you were like, “I have no idea what they’re talking about,” but that stayed with you from that experience?

Tren Griffin
So in that era, Seattle had a tolerance policy. And if you were south of Yesler, which is a street that goes east to west, there was gambling and prostitution, and cops were being paid off, and there’s bingo and all kinds of crazy stuff. There’s drugs. Illegal gambling was probably the biggest thing. But anyway, they would talk about that, and who was corrupt, and the governor was corrupt, and this guy was the bagman. And it was a smaller town. And the thing I took away from it was, this is damn interesting. But also that people are human, and things aren’t always what they appear. And so that nice hotel right there is actually a brothel, and all these things.

But it was different in that, when I was six, I was very old, and so I was paying attention. And so we’d go on a trip someplace, Palm Springs or skiing or something, and I’d see Mr So-and-so kissing some 24-year-old, and I’d say, “That’s not his wife.” My dad would say, “Yes, that’s...” But most kids didn’t pay attention to that. But I said, “Okay, I want to know why that happened. Why would he do that?” Because I want to understand the motivation. I was observant to a fault early on. And so listening to those things made me curious about how the world really worked, and then how the world appeared to work.

And once you learn about something, then you want to know a little bit more. Like, “Okay, well, who’s taking the bribes, and how did they get distributed, and why did they choose Yesler, and which of these buildings has a casino in it,” and all these sorts of things. So anyway, I think we were both genetically curious, and probably at an earlier age than most people. But everybody can get curious, because it’s fun. It’s just fun to learn. It’s fun to discover. Like, why does this restaurant packet of mustard taste better than the stuff in the jar? Well, the stuff in the jar has vinegar, and there’s a chemical reaction that happens when you open this thing up. And if you mix your own powder, you can have a chemical reaction and it tastes better. But knowing that is fun. Learning that is fun.

But for some people, it’s not fun. “Why would I want to know that? I just want to focus on my Corvette I’ve got in the garage, and I work on that, and it makes me happy, and that’s all I think about.” I go to bed... it’s not me. But it makes them happy, if it cranks their... Look, if they want to get home and just turn on Jim’s OnlyFans, it’s okay. I’m not judgemental.

Jim O’Shaughnessy
You’re doing such a good job of marketing my non-existent OnlyFans, I might actually have to open one.

Tren Griffin
I think it’s a chance to diversify the imprint brand. A lot of these publishers are talking about being multimodal: video, all that. And you could publicise a lot of things there. You could advertise. You could get... like, Speedo would give you big money for wearing a tight Speedo.

Jim O’Shaughnessy
I admire your optimism, but...

Tren Griffin
Placement. They’ll give you a Speedo.

Jim O’Shaughnessy
But let me correct your assessment. Speedo would probably pay me a huge sum of money not to wear a Speedo and show it. So, whenever I’m talking to you, I glance at the time and the time just disappears, which means a very good thing. What are you doing right now? Are you agreeing with Craig, and what are you doing specifically to do this book in public that you want our listeners and viewers to know about?

Tren Griffin
I’m really not supposed to talk about what’s in it yet, but what I’m trying to do is take some key ideas and illustrate them with stories.

Jim O’Shaughnessy
Okay.

Tren Griffin
And to not make it too complex. But it’s a book about investing. I can say that.

Jim O’Shaughnessy
Okay.

Tren Griffin
It’s a book about investing principles. It’s like my blog. Someone said nicely the other day, or yesterday or something, on Twitter, “I love 25iq because it’s timeless.” There are 300 posts there. There’s over a million words. And I didn’t write it to say, “Well, this is what’s going on today.” I think in one case I went into one business deeply. But I was trying to be timeless, and I’m trying to do the same thing. But the other thing is I’m trying to be happy and enjoy the process of writing the book.

Jim O’Shaughnessy
Yeah.

Tren Griffin
You can’t torture yourself. And being happy is tremendously underrated. So I’m trying to be happy. I’m trying to be focused. I’m trying to be passionate. I’m trying to create something that I feel proud of, that might help people, that is paying it forward.

Jim O’Shaughnessy
I think that’s a wonderful motivating thing when you’re writing your eighth book. I’ve always... and I think you probably agree... I view happiness as a byproduct.

Tren Griffin
Right.

Jim O’Shaughnessy
And by that I mean, there are so many books on how to be happy, how-to books. And I think that if you make it conditional and you say, “When I get X, then I will be happy,” you’re setting yourself up for failure.

Tren Griffin
Absolutely. I know so many rich, unhappy people.

Jim O’Shaughnessy
Oh, no kidding.

Tren Griffin
Right. And I know many people who don’t have anything who are super happy.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And then I know rich people who are super happy. And so you could draw a matrix with the quadrants. But a lot of it is just up to you. No one’s going to make you happy.

Jim O’Shaughnessy
Oh, truer words were never spoken. Yeah, that is absolutely correct.

Tren Griffin
And it’s very hard to make someone else happy, and it’s even harder to make them change in some way.

Jim O’Shaughnessy
Yeah. Right.

Tren Griffin
And so you get to acceptance. But then you get to the fact that, at least with your own behaviour and your own happiness, you’re in control.

Jim O’Shaughnessy
Yes.

Tren Griffin
Right? I have this saying that I talk to people about, which is: you’re going through your day and some guy comes up to you and says, “Hi, you’ve been really smart. Will you help me with this problem? Here’s this turd. Will you take it?” And the answer, of course, is, “No, I’m not. It’s a very nice turd, but you keep holding that. Here are some things you might want to think about, and here are some resources, and good luck with that.” You should only take on things that you want to take on. You should take on things that make you happy and productive, but realise you’re in control. If you’re unhappy, it’s because you’re letting yourself be unhappy. No, someone else isn’t making you unhappy. You are.

Jim O’Shaughnessy
Completely agree. And there are so many simple things that are not easy. Like investing. The way I look at investing is, there are a lot of simple ways you can do very well, but they’re very hard to actually do. And I love the idea about the turd. “No, thank you. You keep that turd.”

Tren Griffin
It’s a very nice turd. Good luck with that turd. But I’m not grabbing it.

Jim O’Shaughnessy
Lovely turd. And I definitely agree that it is ultimately up to you. Because, uniquely... Exactly. Right.

Tren Griffin
You don’t need anybody’s permission.

Jim O’Shaughnessy
Right.

Tren Griffin
You don’t need... It’s frictionless.

Jim O’Shaughnessy
Yeah.

Tren Griffin
As opposed to, “Well, if so-and-so doesn’t like me, I won’t be happy.”

Jim O’Shaughnessy
Right.

Tren Griffin
That’s a setup. That’s handing someone else control over your happiness. It kind of reminds me of the margin clerk, when you’re borrowing on margin: they can sell that stock when it gets low. So you’ve basically said, “Here, you determine my fate.” This is like, “Well, unless you help me, unless you do these things and you say that I’m wonderful, I can’t be happy.” Well, no. You don’t want to do that. Again, you can strive to be... you can strive to have someone like you. You can strive to have them approve, or not think you’re an idiot, or whatever. But you’re in control. And that’s just... this is beautiful.

Jim O’Shaughnessy
I again could not agree with you more. I’m sure you’ve read Cialdini’s Influence.

Tren Griffin
Yes.

Jim O’Shaughnessy
And one of his first principles is reciprocity. And I do think sometimes that, we talked about genetic curiosity, et cetera, I do think that there is, in many people, a strong component to their personality where reciprocity can be a bitch. Because let’s take the guy with the turd. Prior to asking you to take the turd from him, he does something really nice for you.

Tren Griffin
And then you’re supposed to take the turd.

Jim O’Shaughnessy
Yeah.

Tren Griffin
That’s like the woman, the guy, the Buddhist monk or whatever, who gives you the flower in the airport and then asks for the donation.

Jim O’Shaughnessy
And by the way, that was based on that principle. The Hare Krishnas studied that. They actually had a pretty good marketing plan.

Tren Griffin
Yeah.

Jim O’Shaughnessy
Because...

Tren Griffin
And reciprocity is a powerful thing.

Jim O’Shaughnessy
It really is, until it gets ruined. Like the example of the Hare Krishnas with the flowers in the airport: for the first couple of years, that worked really well, until people became inured to it. They don’t take the flower; they won’t take the flower. And then you’ve got to move on. But I think the broader point that is worth people contemplating is, unfortunately, there are other people who are doing their very best to manipulate you as well. And one of the downsides of social media is that a lot of the things are posted there specifically to get you angry, to get you nervous, to get you worried, et cetera. And so I always say to people, get in the habit of saying, “Why am I reading this now? What would happen if I actually believed this? Who wants me to believe this? Is it a guy who wants me to take his turd from him?” And yet those kinds of simple questions elude a lot of people.

Tren Griffin
Yeah. The truth is: be true to yourself, be kind to yourself, and don’t take the turd. Those are the three principles. Then, in my next book: Don’t Take the Turd.

Jim O’Shaughnessy
Don’t Take the Turd.

Tren Griffin
Please.

Jim O’Shaughnessy
If you do nothing else, send Don’t Take the Turd to us.

Tren Griffin
My current book is not... there’s nothing about that. But that’s sort of the life advice thing. The Munger-esque stuff is, there are some things that are really pretty simple, and there are some things that are complex, and there are some things that involve ambiguity and uncertainty, some things that involve what Zeckhauser called ignorance. There’s deep uncertainty. There are black swans there. There are tail events. Life is complex, but if it wasn’t, it’d be damn boring. Nothing like a little stirring things up, a little soup. You don’t want to sit around and not have anything going on. It’s like a lot of people who were really smart had already checked out, and then AI came along and said, “Oh, I’m in again.”

Jim O’Shaughnessy
Yeah.

Tren Griffin
This is fun. This is cool. Quantum. Wow. Let’s go. Let’s go. You don’t want to be bored. You don’t want to have things stay the same, because life is short. Someone said to me the other day, life is like a toilet paper roll: towards the end, it goes really fast.

Jim O’Shaughnessy
And that is very true. And I also could not agree more about, man, if you don’t mix it up, life just gets really boring really fast. And we get one time around on this baby, hopefully.

Tren Griffin
The other point is, you have a career, and you have all these interesting people, and you’re getting challenged, you learn things, and all that. And then just because you decide not to take a W-2 anymore, which I decided when I was 71. I said, “Okay, it’s time not to have a W-2. Time to focus on fishing, time to focus on writing books, time to focus on this consulting work that’s just super interesting.”

Jim O’Shaughnessy
Yeah.

Tren Griffin
And I can order my own life when I want to, and all those sorts of things. But you still need these interesting people. And so you need to find ways: how am I going to be around interesting people? Who’s going to challenge me? And it can be not real people. It can be virtual people, in terms of what I read, what I listen to, what podcasts I listen to. But you don’t want to go into a state where, “Okay, well, I don’t have a W-2 anymore. What am I going to do now?” My mom told me about people she lived with, and the wife had been on her own for 20 or 30 years, and the husband was suddenly retired, and he’d start following her around, and eventually she would turn around and say, “Go find something the hell to do. Get out of here. Go someplace. Get out of here.” Because she’s used to having her own life.

And you don’t want to be in that situation where you don’t know what to do, so you’re just following your wife or husband around. It can be the other way. Some guys are retiring before their wives. But the point here is: seek out what interests you. Seek out your passions. Find new passions, do new things, try new things. Don’t be boring.

Jim O’Shaughnessy
Totally agree. And I took the advice from my grandfather, when I was lucky enough to spend a lot of time with him when I was a kid. He was born in 1885 and died in 1973, at age 88. He had a wonderful life. I remember one of the last things, when I was a teenager and he was getting on, I’m like, “So what do you credit everything to?” And he said, “Never retire, and always find something interesting that you hadn’t done before.” Those are two pieces of advice, and, boy, you seem to live them, Tren.

Tren Griffin
The key thing is, not having a W-2 does not mean you’re retired.

Jim O’Shaughnessy
Of course not.

Tren Griffin
There’s so many things to do.

Jim O’Shaughnessy
Of course not. Absolutely.

Tren Griffin
We’re about to wrap up. I interrupted.

Jim O’Shaughnessy
No, that’s okay. I actually think you’re absolutely right, because a lot of people do equate the two: “Oh, now I don’t have a W-2 anymore, I guess I’m retired.” No, you’re not. You can do a ton of different things, like you’re doing, like a ton of people are doing. And you really want to do that, because life will get boring very quickly if you don’t. I’ve been married nearly 45 years, and I would have been divorced long ago had I hung around the house.

Tren Griffin
Give the person you love some space. Can be excellent advice.

Jim O’Shaughnessy
Yeah, it really is. Well, Tren, as always, I have a wonderful time chatting with you. I think this has been a great conversation. As you recall, you get to... and now you’re on your third time, so you get to really incept people.

Our final thing is: we’re going to make you the emperor of the world. You can’t kill anyone. You can’t incarcerate anyone. But we’re going to hand you a magical microphone, and you can say two things into it. I bet I can guess what one of them is going to be. But you can say two things into it, and you’re going to incept the entire population of the world. Whenever their morning is, they’re going to wake up and they’re going to think, “I just had two of the greatest ideas. And unlike all the other times, I’m going to actually take action against both of these ideas today.” What are you incepting in the world’s population?

Tren Griffin
I think that probably the keyest thing is to find your passion: to find the thing that motivates you, to find the thing that wants you to learn more, do more, help people more. Find that passion. The best way to do that is just with experiments. You just do a lot of things, and you do more of the things that really float your boat, that charge you. And once you find that passion, then all these other great things flow from it.

And then the second thing is: really listen. We’re all good... me particularly. I could do a better job listening. I know I could do better. I should listen more. And you really have to listen, because you can get into your own grooves. One of the things I’m talking about in the book I’m writing is path dependence. You can be like a snowball rolling down the hill, and the bigger you get, you can’t change the motion of this thing that’s going down the hill. But you really have to change, and you really have to adapt. AI right now is really that way, which is, maybe you used to do X and that was your thing, but now you’re expected to do the whole stack yourself. And unless you can change, you’re in trouble.

Jim O’Shaughnessy
Yeah.

Tren Griffin
And so the only thing that doesn’t change is change. It’s always going to be different. So you have to listen. So be passionate and listen. If there are only two things, that’s what I’d say.

Jim O’Shaughnessy
I love both of them. Good old Heraclitus for the win: “The same man cannot step in the same river, because he is no longer the same man, nor is it the same river.” Tren, I always have a wonderful time chatting with you. We will put up all of the places that people can find you when we post the podcast. But thank you so much for giving me so much time.

Tren Griffin
All right. Good luck with the OnlyFans.

Jim O’Shaughnessy
You’re going to carry that bit right to the bitter end, aren’t you? I admire the persistence.

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Spencer Greenberg, mathematician, founder of Clearer Thinking, and co-author of The 12 Levers, joins us to talk about which self-help techniques hold up to evidence, why memory works like autocomplete, how exposure therapy dramatically reduced his lifelong social anxiety, why the law of attraction can backfire, how to design hiring interviews that predict performance, and what his team found replicating new studies from top psychology journals.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Subscribe to The OSVerse to receive your FREE copy of The Infinite Loops Canon: 100 Timeless Books (That You Probably Haven’t Read) 👇👇

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Links

Show Notes

Spencer Greenberg & Jim O’Shaughnessy

• Spencer Greenberg: Mathematician and entrepreneur, founder of ClearerThinking.org and Spark Wave, and host of the Clearer Thinking podcast. Clearer Thinking

• The 12 Levers: Spencer and Jeremy Stevenson’s evidence-based toolkit for improving your life. The 12 Levers

• Clearer Thinking podcast: Spencer’s interview show, where Jim has been a guest. Listen

• Transparent Replications: Spencer’s project that randomly picks and re-runs new studies from top psychology journals. Transparent Replications

• Importance hacking: Spencer’s essay on the problem his replications uncovered. Read the essay

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned

• Reality tunnels: Robert Anton Wilson’s idea that everyone perceives a different version of reality. Reality tunnel

• The Challenger memory study: Research showing how far people’s memories of a major event drift over time. Flashbulb memory

• Spaced repetition: Spencer’s recommended method for remembering what matters. Spaced repetition

• My Dinner with Andre: The film that shaped how Jim designed Infinite Loops. My Dinner with Andre

• Behavioral activation: The evidence-based depression technique Spencer describes. Behavioral activation

• Daniel Kahneman: Whose work for the Israeli military showed which interview methods actually predict performance. Daniel Kahneman

• Pre-mortem: The technique of imagining a plan has failed and working out why. Pre-mortem

• Replication crisis: The finding that many published psychology results don’t hold up when re-run. Replication crisis

• John Sarno: The NYU physician whose work on the mind’s role in chronic pain Jim credits with curing his frozen neck. John E. Sarno

• Molecules of Emotion by Candace Pert: Jim’s reference on how emotions show up physically in the body. Candace Pert

• Mirror box therapy: The phantom limb treatment Spencer uses to show the brain can reinterpret a pain signal. Mirror box

Highlights

Memory as Autocomplete

There’s a wonderful study that illustrates this really well. After the space shuttle Challenger exploded, a teacher took advantage of it to do a psychology experiment where he asked his students to write down: what were you doing when you found out? What was going on for you right at that moment? And then years later, he had those same students write again, the same question: what were you doing when the space shuttle Challenger exploded? And then he had them compare. And it was absolutely shocking how different the two accounts were. And some students were like, “I don’t believe this is what I wrote. I don’t think that was actually me,” because they just couldn’t believe that their memory could be so wrong. It really can be disruptive, this idea that we don’t remember things. It’s so core to our identity, these facts about our history.

But I think that we just have to accept that is just the truth about the way memory works: that not only do we forget most things, but even when we remember things, we can distort them during the memory process. As you recall them, it’s not like pulling a file from a drawer. It’s kind of like generating a file from scanned information. One way to see that is if you try to remember your childhood home. You kind of picture it in your mind, and you’ll probably be able to visualise it to some extent. But then if you ask a really specific question about it (what colour was the doorknob?) you’ll probably have an answer. But most likely it’s just going to be filled in in that moment, right?

It’s generated, or some other little detail may not be in your memory, but your memory is just making a best guess. It’s like autocomplete. Our brains are kind of autocompleting. But then the next time you recall that memory, now the doorknob might be remembered. And so now you’re not autocompleting, you’re remembering your previous autocomplete.

Productive Disagreement

I’ve actually run a number of workshops on productive disagreement, where we bring people together in a room, and we have them fill out a long list of things that they agree to, they disagree to. So, you know, hot-button political topics, things like that. Then we match them with a stranger in the room. We have them overlay their sheets and find something where one of them strongly agrees and one strongly disagrees. And we’re like, “Okay, you’re going to talk about that, but you’re going to do it in a special way. You’re not just going to have a normal conversation.” The first part of the conversation, person A is just going to ask open-ended questions of person B until person A can restate person B’s thesis and ideas and beliefs so well that person B is like, “Yep, you got it. You understand me.” And then they switch roles, and now the other one asks open-ended questions until they fully understand the other person’s point of view. So now, after this first segment, they can both restate the other person’s point of view to the other person’s satisfaction.

And then, in the final phase, they work together as a team, collaboratively, to try to figure out the root of their disagreement. And they win together by figuring out the root, not by proving they’re right or convincing the other person. So I call these productive disagreements. And I find them really fruitful in my own life. But also it’s gone really well running these as workshops, because we’re talking about sometimes really difficult topics, and yet people come away being like, “Oh wait, we actually disagreed less than I thought,” or, “I don’t agree with the other person, but I understand their point of view now.” And so I find that a much more useful way to think about things, rather than a debate.

Edited Transcript

Jim O’Shaughnessy
Well, welcome to Infinite Loops. Spencer, I have been a longtime fan of yours. As you know, I was on your podcast, where we talked about some of my challenges in trying to design a system that would help me make better choices on Wall Street. Your book, 12 Levers, is fabulous. We’re going to talk about that later though, because you are on my buddy Chris Williamson’s Modern Wisdom currently, which I watched and thought was excellent. And we will get into the book, but I want to start in a different place. Close your eyes.

Spencer Greenberg
All right. Well, first of all, thanks so much for having me. But yeah, I’ll close my eyes. I don’t know where this is going.

Jim O’Shaughnessy
Okay. This is something that I read that you advocated, and it’s about perception with your eyes closed. Describe what I’m wearing.

Spencer Greenberg
So I think you’re wearing a kind of grey button-down shirt, right?

Jim O’Shaughnessy
That’s correct. Anything else you can describe?

Spencer Greenberg
Nope, I literally have nothing. I didn’t notice anything else.

Jim O’Shaughnessy
Okay, open them up again. Are you a fan of Robert Anton Wilson?

Spencer Greenberg
No.

Jim O’Shaughnessy
Okay. He has this idea that we all have different perceptual reality tunnels, he calls them. And he once did something similar. By the way, everyone listening and watching, this was Spencer’s essay that I read, and that’s why we did this exercise. But what he did was even more aggressive. He was giving a class, and it’s down a long hall in a college. The first day, all his students came in and he told them, “I’m closing the door. Everyone take out a blank sheet of paper. Draw the hallway.” And what he discovered is every drawing was different. Talk to me a little bit about what motivated you to bring that up, because it fascinates me that we all really do perceive things differently. And talk a little bit about how the exercise we just did can be helpful.

Spencer Greenberg
One thing I think is important to realise is that we’re constantly in a state of forgetting. Almost everything that happens to us is just gone from memory. And what we’re left with are these little samples that we then build stories out of, that are what we tell ourselves about our lives. That can really matter in relationships, and it can really matter in lots of different areas of life where, let’s say, we have an interaction with a person and we leave the interaction feeling angry. But then the constant forgetting means that we actually forget most of what happened there. And now, from those little bits and pieces, we try to retell the story of why we’re angry. And it probably involves the other person doing something wrong and us being right, naturally.

So there’s a technique that I really like that I called the Inner Why technique. It’s very simple, but it asks you to make a little game where you try to notice every time your emotion shifts, especially for the negative, over the next few days. And as soon as it shifts, you just ask, “Why? Why did it shift?” And what’s neat about it is that, because you’re trying to do it the moment your emotion shifts, typically there’s only one thing that happened: one thing that was said, one thought that you had. And it’s typically very easy to pinpoint why am I feeling that negative emotion. And it can increase your awareness, make you better at navigating difficult emotions, help you better understand what your role is in these situations.

But if you wait even just 20 minutes, you might just have the lingering feeling of anger or annoyance and not be able to identify where it came from, because of this constant forgetting.

Jim O’Shaughnessy
And I also read, when I was reading your stuff, we have something like thousands of thoughts a day. And if at the end of the day you ask me, “Hey, Jim, how many thoughts do you have today?” I’d probably say either none or a couple. And that’s that constant forgetting, right?

As a longtime journal keeper (so I’ve kept journals, not diaries, what I’m thinking, et cetera, for 40 years), one of the things that I was really blown away by was being called a liar in my own handwriting. I had a memory. It was about the first Gulf War, and I was at a cocktail party here in Manhattan, and everybody... This was when we did the second Gulf War, right? And everybody that was in the conversation had the same view: “Well, you know, I supported George Sr. going in because, after all, they invaded Kuwait and everything. But I do not support this particular incursion into Iraq.” I said the same thing. I would have sworn in court that was what I believed. And then, I don’t know, a couple days later, I was looking for something in my journals from that period. I found I did not support the first Gulf War. And I was really struck. So I started going back and I started seeing, wow, are we constantly overriding our memories?

Spencer Greenberg
There’s a wonderful study that illustrates this really well. After the space shuttle Challenger exploded, a teacher took advantage of it to do a psychology experiment where he asked his students to write down: what were you doing when you found out? What was going on for you right at that moment? And then years later, he had those same students write again, the same question: what were you doing when the space shuttle Challenger exploded? And then he had them compare. And it was absolutely shocking how different the two accounts were. And some students were like, “I don’t believe this is what I wrote. I don’t think that was actually me,” because they just couldn’t believe that their memory could be so wrong. It really can be disruptive, this idea that we don’t remember things. It’s so core to our identity, these facts about our history.

But I think that we just have to accept that is just the truth about the way memory works: that not only do we forget most things, but even when we remember things, we can distort them during the memory process. As you recall them, it’s not like pulling a file from a drawer. It’s kind of like generating a file from scanned information. One way to see that is if you try to remember your childhood home. You kind of picture it in your mind, and you’ll probably be able to visualise it to some extent. But then if you ask a really specific question about it (what colour was the doorknob?) you’ll probably have an answer. But most likely it’s just going to be filled in in that moment, right?

It’s generated, or some other little detail may not be in your memory, but your memory is just making a best guess. It’s like autocomplete. Our brains are kind of autocompleting. But then the next time you recall that memory, now the doorknob might be remembered. And so now you’re not autocompleting, you’re remembering your previous autocomplete.

Jim O’Shaughnessy
And so we are overriding, right? And do we do that for coherence’s sake? Do we do... What’s your thesis on why that happens? Is it just the way that our brains are structured, or is there something more?

Spencer Greenberg
Well, I think it’s somewhat debated, but my view is this is a clean evolutionary story, where brains are optimised for survival and not really other things, right? They’re really just trying to get our genes to survive to the next generation, propagate. And if you think of it that way, we don’t need to remember all these little details, right? We need to remember the big-picture stuff, the important stuff. And in fact, it might challenge our memory storage if we actually could remember everything. Maybe we run out of space. So the brain tries to be extremely efficient and just remember kind of the important things.

And then this autocomplete idea is really powerful, because it can often guess the right details of things you don’t remember by using other memories, for example. And just, “Oh well, the doorknob probably looked like that, because that’s what doorknobs look like.”

Jim O’Shaughnessy
And the thing that fascinates me is that can cause all sorts of trouble. And is there a technique? My technique tends to be I document, like, almost everything. When you leave, I’m going to do a series of notes in here about our conversation. And I found that’s very, very helpful for me to do. Are there other strategies, or is it even advisable to want to be able to remember more of the actual things that transpired?

Spencer Greenberg
Yeah, I think that it’s important to focus on what you actually want to remember and why, because a lot of these details of our lives, we don’t actually need to remember them well. We need to remember certain important things. For example, when you read a nonfiction book, I think taking a little bit of time to take some notes is really powerful, because it can actually just help you get a lot more out of that book. If you don’t take any notes at any point and never review them, there’s a pretty good chance in three years someone says, “Well, what was that book about?” And you can remember one or two things. And so if it was a really valuable book, I think it is worth taking just a small amount of extra time. It can help consolidate those important memories.

But at the same time, I don’t think we want to get lost and think, “Oh, I need to remember everything,” and try to grip onto everything. It’s just not realistic. So what is really key? What are the things that you really care about knowing? And then you can use simple techniques like make notes, but then review those notes at a certain periodicity. Spaced repetition can be a really powerful technique for this, where if you are trying to remember something, you don’t need to review it every day. In fact, after you’ve learned it, you can review it at longer and longer intervals to keep it in memory. So maybe the first time you review is the next day, then the next week, then three weeks later, and so on. If you get it wrong, then you review it at faster intervals again. But if you get it right, you can keep making the intervals longer and longer.

Jim O’Shaughnessy
Yeah, I also have kind of a weird memory, in that if I read something, my recall of it is pretty high. If I hear something or I see something, or, God forbid, I’m at a party, I don’t remember, like, virtually any of it. Are those types of preferences, if you will, do they lead to different ways of thinking, do you think?

Spencer Greenberg
There’s this fascinating phenomena where many people report having certain types of learning work better for them than other types. But the research on this is actually really kind of surprising, because there’s essentially no good research that demonstrates that giving people different types of learning materials (like, some people are auditory learners, some are visual learners) and making the right learning material for their type actually produces better educational outcomes. So that’s the strange thing: the research is out of sync with what many people just anecdotally experience. And that might be because the concept is fraught, but it also might just be because it’s really hard to design those experiments, because you’d have to actually correctly identify someone’s type. Then you’d have to have a bunch of versions of your educational materials that are well optimised for each type. Maybe that’s just a really high bar. So in practice, there’s actually very little known about how to kind of specialise information for people’s learning type.

Jim O’Shaughnessy
One thing: when I was younger, I was into neuro-linguistic programming, and so auditory, kinaesthetic, visual. And I did find... and of course this is pre me documenting everything. I did find that if I listened closely, I could pretty much grok what style my conversant preferred. And so you don’t say, “Does that ring a bell to you?” to somebody who’s a visual thinker.

Spencer Greenberg
Right.

Jim O’Shaughnessy
You want to say, “Can you see the big picture?” And I did find that by making just small adjustments to the way I was talking to the person, when I switched over to their preferred method, they became more engaged, they relaxed. It was very interesting to me. I wish I would have documented that more.

Spencer Greenberg
Well, that’s a really interesting example of something that we actually talk about in our book, The 12 Levers, around how you can actually transform conversations with people by learning to pay more attention. Very often when people are in conversations, maybe they’re 80% focused on the other person, but they’re a little bit thinking about what they’re going to do tomorrow. They’re a little bit distracted by what’s in the corner of the room, or thinking about, “Oh, I want to talk to that person next.” And it can really, actually be transformational, really trying to give the other person your complete, interested attention and really sort of be fully there with them. And if you hear about people who met, like, Bill Clinton or the Dalai Lama, they’ll often mention things like this. They felt like even this important person was suddenly fully there with them. And it really strikes a chord with people. And I think we can all learn to do that better.

And so I think the example you’re giving is actually a great example of this, of what happens when you learn to pay more attention. You start noticing things you never noticed. I had an instance where I was at a holiday party, and this guy who talks to me at all the holiday parties comes up to me, and I never had a good conversation with him in my life. And I kind of have this internal groan when he comes and talks to me. So he comes back to me and I’m like, “Okay, I’m going to really try to give him my complete, full, interested attention, 100%.” And I did it. And for the first time ever, I had a really good conversation with him. And I was like, “Wow, maybe this is a me problem. Maybe this guy’s fine.” And that really changed my thinking on this.

Jim O’Shaughnessy
And then how did you incorporate that? How did you habituate that? Because, you know, there’s a lot of great advice in your book, but I think you’ve got to habituate the behaviour if it’s going to make any difference.

Spencer Greenberg
Right. Yeah. So one of the really useful ideas is trying to pick a trigger, right? So you have a trigger, and then you’re going to say, “Okay, the next five times I see this trigger, I’m going to make sure to do this thing.” And if you can stick with it five times, that will make the sixth more likely, and the seventh more likely, et cetera. So for me, the trigger is when a one-on-one conversation starts with someone. That’s going to trigger, “Okay, now I’m going to try to really focus on this person, really try to pay attention.” It’s still something I’m working on. I could certainly still improve, but already I feel like it pays gains in my life, even if I don’t do it perfectly.

Jim O’Shaughnessy
Yeah. And your mention of... I had the pleasure of meeting Bill Clinton after he was president, and I was blown away by the attention he paid to me. I felt, literally... It might have been a five-minute conversation, but I felt like he was a million-watt light bulb and all of that energy was just focused on me, given the way he asked questions, et cetera. And again, this is a five-minute conversation.

Spencer Greenberg
That’s exactly what I’m talking about.

Jim O’Shaughnessy
And so he clearly has mastered that. And then you add to it, he’s like, “O’Shaughnessy. Galway, right?”

Spencer Greenberg
Yeah.

Jim O’Shaughnessy
And I just found that really interesting. I think that gives people a tremendous advantage, right? Because I find that a lot of people are really not listening. What they’re doing is thinking about how they’re going to respond. And that’s why you get these people on TV shouting at each other, and, you know, “I did not...” And no real communication has taken place.

Spencer Greenberg
Yeah. It not only causes other people to like us more, but importantly, it often makes conversation more interesting for both people.

Jim O’Shaughnessy
Totally.

Spencer Greenberg
Because by being really focused on what they’re saying, you often notice nuances that you would completely miss. You notice directions you want to take the conversation. And, you know, my own podcast, Clearer Thinking, which you’ve been on... I don’t know if you’ve observed this, but having done hundreds of interviews, I realised that when I was a younger interviewer, I would often miss important conversational branches that, by paying more attention, I actually now start to pick up on more. You just realise, “Oh, wait, there’s a really interesting thread here. And we could have just blown right past it.”

Jim O’Shaughnessy
Yeah. And when I was designing this podcast... I don’t know if you’ve ever seen the movie My Dinner with Andre. It’s a 1980, I think, movie. Anyway, it’s just a conversation, literally. And it’s riveting. It’s literally riveting. And you feel like you’re a fly on the wall in this conversation. But one of the things that happens between the two is they actually listen to each other, and then they disagree, they agree, et cetera. But they also go down tangents, right? It’s like, when I started doing podcasting, I would say, “Yeah, we’ll get to that later.” Big mistake. If you see something, if you see an opening, take it then. And the conversation just becomes more interesting, but also just more authentic, because, you know, why are you going to remember something we covered now, 20 minutes from now? Why don’t we cover it now?

What more can people do? I think that we have a situation where people literally... Maybe it’s because our perception filters, our reality bubbles, tunnels, are different, so different from one another that, you know, same movie... As Scott Adams would say, “Same movie, two different screens,” right? Do you think there are some techniques that people could study and then habituate that would make communication more fruitful?

Spencer Greenberg
I’ve actually run a number of workshops on productive disagreement, where we bring people together in a room, and we have them fill out a long list of things that they agree to, they disagree to. So, you know, hot-button political topics, things like that.

Jim O’Shaughnessy
Sure.

Spencer Greenberg
Then we match them with a stranger in the room. We have them overlay their sheets and find something where one of them strongly agrees and one strongly disagrees. And we’re like, “Okay, you’re going to talk about that, but you’re going to do it in a special way. You’re not just going to have a normal conversation.” The first part of the conversation, person A is just going to ask open-ended questions of person B until person A can restate person B’s thesis and ideas and beliefs so well that person B is like, “Yep, you got it. You understand me.” And then they switch roles, and now the other one asks open-ended questions until they fully understand the other person’s point of view. So now, after this first segment, they can both restate the other person’s point of view to the other person’s satisfaction.

And then, in the final phase, they work together as a team, collaboratively, to try to figure out the root of their disagreement. And they win together by figuring out the root, not by proving they’re right or convincing the other person. So I call these productive disagreements. And I find them really fruitful in my own life. But also it’s gone really well running these as workshops, because we’re talking about sometimes really difficult topics, and yet people come away being like, “Oh wait, we actually disagreed less than I thought,” or, “I don’t agree with the other person, but I understand their point of view now.” And so I find that a much more useful way to think about things, rather than a debate.

Jim O’Shaughnessy
Are you familiar with Nick Gruen’s work? He’s an Australian, and he advocates for the jury system. Because this is the result, right? They didn’t intend it to be the result. But when you’ve got the one holdout, “Guilty as hell,” and the other one, “No, did nothing wrong,” they literally have to solve the problem, right? And so you get a much different outcome when you jury something, as opposed to the standard political stump speech: “This is why you’re gonna love,” fill in the blank, right? Data centres, or what have you. And at least the research of his that I’m familiar with, it seems to lead to much better outcomes.

One of the things that I started doing aggressively when large language models got better was to always steelman points of view that I disagree with. And you’re right. I do them on everything, right? Really hot-button topics. And I don’t think I’ve ever steelmanned an argument that I really vehemently disagree with where I haven’t looked at it and said, “They do have a point.” And so it’s helped me to update my priors.

Spencer Greenberg
Right.

Jim O’Shaughnessy
Because I think that we all have this idea that we’re right, right? And we’re often not even close to right. We’re often very wrong. And so I’ve always been fascinated by mental models, as you know. And one of the things that I wanted to ask was, do you think you would be more effective if you designed a system? On your podcast, we talked about why I became an algorithmic quant investor, right? It was basically to guard against the emotions that all investors face. And I just saw, by reading history: wow, when the emotions take over, watch out. Fear, greed, hope and ignorance are the four horsemen of the investment apocalypse, and only ignorance can be dealt with.

You do something fun with your parties. We’re going to shift over there. I was absolutely fascinated. Just briefly... I’m going to let you describe it, but you have parties here in New York where you can never use the same format twice. I want to get to why that is. But the things you’ve covered, I think, are just so cool. Like, one party was people dealing with shame. Another was radical honesty. Another was kind of a fight club mentality, where you could choose which one you were going to do. First off, what inspired you to have parties like this? And, more importantly, what did you learn from the outcome of these parties?

Spencer Greenberg
Yeah. So I run a group called Ergo, and we’re a social experiments group. We throw social experiments. And as you said, we have a rule: we’re never allowed to repeat the same format twice. The way it came about is, for a long time, it was just a regular kind of intellectual meetup. And we would have people come give talks, we would have group discussions, all the standard things. And honestly, I just started getting bored of it. I was just like, “I’m getting bored by my own events. How do we do better?” And also, in a world where you can go listen to the greatest podcasts or watch lectures on YouTube, it’s like, well, why are you coming to an event just to sit and listen to someone speak in front of the room, right?

It didn’t make that much sense to me as the world changed. So then I was like, “Okay, we want to try new formats.” So I went on this research process, and I tried to figure out every format for bringing people together who don’t know each other. And I made this giant list and analysed: well, what is each one good for? So then we started using some of those little more out-of-the-box formats. And then I was like, “Well, I want even more.” And so finally I was like, “Okay, we’re just going to make a group rule. We can never use the same format twice.” And to be honest, it became a form of creativity for me. You know, some people like working with clay or painting, and for me, creating social experiments is just my creative hobby.

So I really enjoy it. And I think of it as this fascinating thing where you kind of drop a rock into the pond and all these ripples come out, and you don’t know what it’s going to be. So you bring people together and you have some change in social dynamics, and different things happen, and it can be extremely unpredictable. You don’t necessarily know until you run the event what’s going to happen. Sometimes it’s quite shocking.

Jim O’Shaughnessy
And not to give away any confidences or anything that might have happened, but what are a couple of examples where you were going into the party expecting one thing, and coming out of the party thinking, “Whoa”?

Spencer Greenberg
Yeah. So one of the strangest is, we did an event we called sensory deprivation socialising. And so the first half of the event, when people arrived, before they even entered, we blindfolded them. They knew this was going to happen. So, you know, they weren’t in shock. But so they didn’t get to see anyone they were interacting with. And most of the people at my events typically don’t know each other, because it’s a large enough group that most of them have never met. So they’re interacting with people they’ve never met, and they can’t see them. They’re trying to understand, “Okay, what are social norms when you can’t see someone?” And, you know, it was kind of funny, because they would make these social faux pas without realising it. They’d be standing way too close to other people, or way too far away. People would get confused about what conversation they were part of and what others were a part of. Suddenly someone would start talking, and they’re like, “I didn’t know there was a person in this conversation.” So that was kind of funny.

But where it got really strange is the second half, where we had people take the blindfolds off, and they could now see, but they weren’t allowed to make any sounds whatsoever. So do you want to guess what happened? A bunch of strangers, they’re going to be socialising for 45 minutes, but no sound. What do you think would happen?

Jim O’Shaughnessy
I personally would think, depending on the group of strangers that you put together, that there would be maybe a Pareto distribution, with 20% having intense, really cool conversations with somebody that, if they could see them, they probably would not have had that conversation. And 80% awkward.

Spencer Greenberg
Yeah. So, well, in the second half, once we no longer allowed them to make any sound, the really strange thing happens. At first people were like, “Okay, I’m just going to try to communicate.” So they would write things down, or, you know, try to get communication without sound. But that is basically just a bad form of talking. It’s less effective, obviously. If you’re trained in it, that’s one thing, but they’re not. So then the strangest thing started happening. People started dancing with each other, total strangers, even though there’s no music. People started, with consent, exchanging massages. And then someone invented a little improv game, and people started copying it. And so by the end, everyone was playing these improv games and dancing.

And I was like, there is no way this would ever happen at a normal cocktail party, where this just suddenly erupts. Just by removing sound, we completely changed the social dynamic.

Jim O’Shaughnessy
Is that one you wish you could repeat?

Spencer Greenberg
It would be interesting to try that in different formats, and kind of vary it in different ways and see what would happen.

Jim O’Shaughnessy
When I took your Ultimate Personality Test, I got all the same things that I always got. I always score off the charts on extraversion. I’m married to an introvert, and so this has caused all sorts of trouble, because I will literally go up to anyone and talk to them. And we were in Miami, and I saw a guy vaping. This is back when vaping was just starting. But he looked literally like a member of the Hells Angels. He had tats everywhere. He had the chains and everything. He was sitting... It was obviously the bouncer for this club. I saw him, and my wife is, “Don’t you dare.” So I wanted to know why somebody like him was vaping as opposed to smoking. And so I went over and struck up a conversation with him.

Had the best 45-minute conversation in a long time. Turns out, very thoughtful guy, really interesting life. We talked about a lot of different things. But then when we got to the vaping, I said, “So what gives?” And he goes, “My old lady, man.” But I find that if you’re willing to kind of go there, there’s just so many fascinating lives in the world that, if you don’t have that urge, you’re going to miss out on. And I was fascinated by... When I was listening to you with Chris, you were talking about your own sort of social anxiety and how you cured that. How’s that going?

Spencer Greenberg
Yeah, it’s been a lifelong project, but it’s phenomenally better than when I was younger. And for anyone listening who’s interested, we have this personality test called the Ultimate Personality Test. It’s free. It’s on our website, clearerthinking.org, so you can check that out. That’s what Jim was referring to. But yeah. So social anxiety I had since I was a child. It was always a problem for me. And then when I was in my early 20s, I was like, “Okay, I really need to do something about this.” And it would typically get most triggered when I was in a social situation where I had to talk to a stranger, and my heart would suddenly start pounding in my chest, and I would feel like I was gonna die. Even though, of course, it’s completely irrational. I was totally safe.

But on some level, my brain was predicting something really bad was going to happen. And I went to a therapist who was really good, really evidence-based, and he said, “Spencer, I can help you, but you’re not going to like the strategy of how.” And I was like, “Oh, what’s the strategy?” He’s like, “Okay, I’m going to give you homework. Every weekend, you’re going to go to a bar alone, and you’re going to introduce yourself to five strangers.” This was absolutely terrifying to me. As an extrovert, you’re probably like, “Yeah, no big deal, whatever.” But it was truly terrifying to me. And so we started small. We made a fear hierarchy of things that were a little bit frightening, a little more frightening, et cetera. And the first level was just go up to people, ask them what time it was.

And even that would make me really anxious. But I would practise that until it became easy, and then I moved my way up. The next one was go up to people, ask them what drink they’re drinking. And I found that a little more difficult than asking the time, et cetera. And it culminated all the way in the final... The final exam was, I went up to men at bars in Manhattan and said, “Excuse me, would you give me a hug?” And, you know, I was like, “I’m going to die. They’re going to punch me in the face.” But yeah, nobody ever attacked me. At worst, they just said no, or they laughed, and some of them gave me hugs. And it had a dramatic effect on my social anxiety.

I think I’ll always be a little bit socially anxious, but it’s so tremendously reduced that there are times now where I’m like, “I think I’m the least anxious person here in this whole room.” In situations that used to be terrifying, I’m just totally fine.

Jim O’Shaughnessy
And that’s kind of like exposure therapy, right? You just expose them a little bit more and more. Are there other therapies that you came across in writing the book that would be equally as effective?

Spencer Greenberg
Yes. It’s fascinating, because there’s so many self-improvement techniques out there, but most of them have not been studied to a tremendous degree. But exposure therapy is one. There’s a ton of really good research showing that it can dramatically improve people’s anxiety. And there’s some nuances in how to do it exactly. And in the 12 Levers book, we talk about the right way to do it, and kind of traps people fall into. But there are other methods that also have really robust evidence. And one of them is for depression. It’s known as behavioural activation. It turns out that even though depressed people often have a lot of negative thinking (they might feel hopeless about the future, they might hate themselves, things like that), they also started reducing their pleasurable activities.

So they tend to start doing less and less of the things they really enjoy. And partly this is because maybe they just don’t feel like doing it, or they lack motivation, but also partly they often predict that they’re not going to enjoy those things. They say, “Oh yeah, I know I normally like that, but I’m just not in the mood. I’m not going to have fun.” And so there’s a really simple but quite effective technique, which is you get people to run behavioural experiments on themselves. And you say, “Okay, let’s make a list of the things that normally bring you the most joy and meaning in your life when you’re not depressed. Let’s have you predict how you’re going to feel doing them, and then you’re going to actually go do them and compare it to your prediction.”

And very often, depressed people find that they enjoy it more than they thought. They don’t necessarily enjoy it as much as someone who’s not depressed, but they tend to enjoy it more than they thought, and it actually can help break them out of these depression spirals. And there’s been a lot of really good research on this technique, and it actually works quite well.

Jim O’Shaughnessy
And exercise is another one, right? If you’re depressed, exercising, like taking long walks, can also be helpful.

Spencer Greenberg
Yeah, exercise is just one... It’s, you know, the closest we have to, like, the miracle drug, which is just... It helps with so many things, including mental health. Yeah. So that’s always a great place to start. Of course, if people are depressed, they often struggle to do things like exercise. And I think there’s way too much emphasis put on the optimal form of exercise. Yes, if you’re a super athlete and you’re already exercising, you know, five times a week, sure, think about optimising. But for most people, I think you want to go the opposite way. I ask people, what is the type of exercise you most enjoy in the world, you find the most fun, where you actually look forward to it? It doesn’t feel like it takes willpower. If anything, it should be the opposite. It should feel like a good guilty pleasure to go do it. Do that first, right? And so for me, I love mixed martial arts. So, you know, if I’m doing mixed martial arts, I enjoy that. If I have to go run, oh my gosh, that’s going to be a lot harder.

Jim O’Shaughnessy
Yeah. And that seems so in line with common sense, right? And by the way, I’m glad you did it so I didn’t have to. You read 106 books, I think, with many therapies also. And I think the final number that you came out with was 500 various takes on how to improve, et cetera. As you know, I love data. And how many of them just turned out to be without any empirical support at all, that people were actually buying into?

Spencer Greenberg
So I want to distinguish between self-improvement techniques that have never been studied, so we just don’t know, and ones where we have actual evidence that they’re harmful, because those are different things. You could have a technique that actually could be quite good, but it’s never been really empirically tested. So there’s a distinction there. I think that there really are some popular ideas in self-improvement that are pernicious, that they actually make people’s lives worse. And often the way that they operate is that they give an initial boost, so you might think, “Oh, this is really helpful to me,” but they might cause harm in the long term. One of the ones I would point to there is the law of attraction. So, this very popular idea that thoughts become things.

And so the idea is not, if you believe in something enough, then you’ll go take action to cause it to happen. That’s specifically not what they’re claiming. They’re claiming that believing something enough causes it to happen without you having to take any action. So for anyone who believes this, I really want you to, every morning, believe as hard as you can that there’s a bowling ball in your freezer, and just do it every morning until you no longer believe this works. But it’s a really pernicious idea, because it basically tells you, if you believe hard enough, it will happen. You don’t actually have to do anything. Which can be really exciting at first, when you start believing it, and can also get you to think positively at first, because you’re focused on all the things you want, not what you don’t want.

So you get this initial kick. But then the problem is, that’s just not the way the universe works. And if bad things happen to you, it can make you easily blame yourself, because, “Oh wait, you got sexually assaulted. Well, what kind of thoughts were you having?” And, like, oh my God, that’s actually a horrendous philosophy.

Jim O’Shaughnessy
Yeah. And I do think the kernel of truth in the law of attraction is what you covered. You gotta take action.

Spencer Greenberg
Yes.

Jim O’Shaughnessy
I make fun... I have a friend who is always saying, “Well, you can do this, Jim,” blah. And I tell him, “Well, manifest it for me.” And he goes, “No, I’m far too lazy to take any action to do that.” But why, then, does that book... Is it just because, kind of, the something-for-nothing... People want the easy path? I wrote... When threads were still a big thing on Twitter, I got really triggered when I was reading one of these: “These are the 10 rules of success. These entrepreneurs do this.” And I’m immediately like, “Biased sample. Self-selected sample. Everything you’re saying here maybe worked for that one guy or woman, and probably didn’t.”

And maybe they’re not articulating... Anyway, I went on this whole rant about, listen, if you just think you can dream things into existence, or that you’re going to succeed by following this list, I got bad news for you. That’s probably not going to happen. What other techniques... But what drives me crazy, right, is those very techniques are the ones that sell 10 million copies of the book, get a movie made, all of that. Is it just the desire for, “Wow, I don’t have to make an effort, and look, everything’s gonna be mine”?

Spencer Greenberg
There’s this generic self-improvement pitch you hear a lot, which is, “Look, I used to be just like you. The problems you have... But look at me now. I’m so spectacular. And because I was like you, and I overcame it, I can teach you the trick to doing it. And by the way, the trick is easy and simple and fast, and it works for everyone all the time.” And of course, none of that’s really true, right? Even the best techniques in the world often won’t work for everyone, right? Maybe they’ll work for a third of people, the best techniques in the world. And then there’s also shit that doesn’t work for anybody. So, yeah. But that’s a really appealing pitch. And sometimes they use other things to make it sound more exciting, like they’ll shroud it in mystery.

You know, a lot of the law of attraction stuff is like, “Ben Franklin was actually using this, and that’s what made him so successful. We’ll teach you the secret of Ben Franklin,” or whatever it is.

Jim O’Shaughnessy
So isn’t there also some kind of transference? You wrote a piece, or did a podcast on it, I can’t remember which. I saw the transcript, so I don’t know if you wrote it as an essay or not. But where people immediately associate celebrities and/or people well known in their industry, and if they hear them say, “I solved all of my problems by,” you know, fill in the blank, do people attach more importance to that because of who is saying it?

Spencer Greenberg
People often describe irrationality as though it was about the individual, because we have all these cognitive biases in our brains. You know, we tend to jump to conclusions, we tend to ignore certain types of evidence, have confirmation bias, et cetera. And that’s all true. But I think actually a significant part of irrationality is social. We as humans, when we trust someone and they tell us a thing, we assume that it’s true by default. Maybe later we’ll get some evidence that causes us to argue against it. But if they’re a person we trust, that we consider an authority, or someone who’s trying to work in our interest, then we absorb the information. And this can obviously be really useful, depending on who you surround yourself with.

But it also means that people often adopt beliefs without ever thinking about them, merely because they come from their trusted authorities. And I think that this leads, actually, to a tremendous amount of misinformation being spread. And then those people spread it to others, not trying to harm anyone, but just because they believed it themselves. And so it’s so important that you vet your authorities, right? And it’s interesting to think about: well, how do you know who’s a legitimate authority? Who’s a trustworthy authority? And there are kind of certain signs that you can look for. One is, does the person explain why they believe the thing? And if they do, then you can go just check it. You don’t have to do it every time, but check at least a few times. “Oh, they said that they believe it because of XYZ. Let’s go check that. That’s true.”

Have they ever changed their mind about something, right? That’s always a really good sign. Like, “Oh wait, this person said, ‘Oh, I’m sorry, I got that thing wrong. I said this. It’s actually this.’” That should update your view. This is a more credible authority.

Jim O’Shaughnessy
Okay. So one of the things that at OSV I encourage is original mistakes. I sort of think mistakes are portals of discovery, if handled the right way. Obviously I don’t want people making the same mistake, but original, novel mistakes can add a lot if you pursue them in the correct way.

How would you... Let’s say I sent you a brilliant young founder, right? And she really talks the talk. She’s going to talk to you about Bayesian updating, and she’s going to talk to you about base rates, and she’s going to talk to you about all of the well-known biases, how she combats confirmation bias, et cetera. How would you disentangle her wonderful way with words to find out... Because I think there’s a big difference between being very well spoken and knowing a lot, and decision-making under adverse circumstances, right?

And so if this person were going to be working for me, this is the one I’m interested in, right? How would you go about... What kind of questions would you ask her to grok, “Yeah, she read it all and she memorised it all, but I don’t think she’s really putting it to the kind of use that I want her to”?

Spencer Greenberg
That would be quite the pitch. For one thing, I think knowledge of these kinds of biases can be helpful, but it’s very far from actually solving the issue. You can know everything about the sunk cost fallacy and still fall for the sunk cost fallacy. In fact, almost everyone does, even if they know that. Or you can do all the anchoring and still get anchored in a negotiation, because knowledge is not enough. So what else do you need besides knowledge? Well, you need to actually think of the right thing at the right moment, right? So let’s say you’re in a negotiation and they throw out the first price. Just theoretically knowing about anchoring doesn’t help. But if you can think about anchoring right at that moment, you say, “Anchoring. I know it’s an issue.” But even that’s not enough. You need one more thing.

You need to know what to do, right? So even if you think of the bias at the right time, you have to know what to do to correct it. Because if you’re like, “Oh, anchoring. Okay, cool. Now what do I do?” Well, you could be like, “Oh, I can re-anchor. So I’m going to create a new anchor to re-anchor this conversation,” right?

Jim O’Shaughnessy
Yeah.

Spencer Greenberg
So it’s knowing what it is, thinking of it at the right moment, and then knowing what to do about it. So that’s what I would try to evaluate in this hypothetical person. I would try to ask questions to understand situations they’ve been in when theoretical knowledge actually got pulled up into their memory. And then, what did they actually do with that knowledge to get a better outcome?

Jim O’Shaughnessy
And how many people do you think fail at that task? So when I was still at Bear Stearns, they asked me to interview a bunch of intern candidates, and they only asked me to do it once. And you’re going to hear why. I didn’t do any of the “Where do you see yourself in five years?”, any of that. With some, I was a little obnoxious. For example, to a person getting a master’s degree in math, I briefly chatted about why math was important on Wall Street, et cetera. And then I looked at them and I said, “Yeah, by the way, what’s 17 and a half percent of 72?” They fled the interview. And so that was maybe a little unkind of me. But the person I wanted to...

I ended up recommending one candidate, and he was the guy who... When I asked all candidates this, by the way, I would say, “Okay, so the S&P 500 is a capitalisation-weighted index that reinvests dividends. The Dow Jones Industrial Average is a price-weighted index that does not reinvest dividends. Both started in the late 1920s.” Well, it’s actually a proxy for the S&P, but the S&P, 90 or 75. “What do you think the Dow would be at today if it reinvested dividends?” And I didn’t expect anyone to get the right answer, and the candidate I asked didn’t get the right answer. What I wanted to see was how he was going to go about solving this.

And so, literally, his response was, “May I have a calculator? May I have some clean sheets of paper? And can I ask you questions?” And I’m like, “Yes, and yes.” And then, literally, for about 25 minutes he just worked it out. “What was the average dividend yield on the Dow between 1926 and...” I think this was in, you know, 2003. Told him, and he came very close. So can you see interviews going that way, as opposed to the... Because I have a somewhat... And maybe it’s wrong, I haven’t tested it, but I think that traditional interview questions actually subtract value, because you’re literally getting no information.

Spencer Greenberg
Right.

Jim O’Shaughnessy
Like, what kind of answer are you going to give to “Where do you see yourself in five years?” And “What’s your biggest flaw?” “I just care too much,” or, “I just work too hard.” Do you think that there are other interview techniques that get much better results in terms of, yeah, that signal that this person might be someone we might want to consider?

Spencer Greenberg
The great, late Nobel Prize-winning scientist Daniel Kahneman did some really fascinating research on this. He did work for the Israeli military, and they were looking at what actually predicts people being good in the military. And there were a lot of questions they would ask that, when he went and studied it, he found it doesn’t really have much predictive power. What it does do is convince the interviewer that they know who’s a good candidate. So a lot of the questions asked make the interviewer feel confident, but they don’t actually predict the thing that we care about. And what he discovered is that what you really want to do is think about all the traits you care about. You want to design questions that are specifically trying to measure those traits, which it sounds like you were doing implicitly.

You’re trying to... “What am I really trying to tell the person’s good at?” And then you’re designing questions to try to get at those things. You want to standardise them, because what happens is, if you create a lot of var... if different people get different questions, you’re rejecting variance in your interview process.

Jim O’Shaughnessy
Exactly.

Spencer Greenberg
So you want to standardise them, and then you want to evaluate the person on each of those individual questions designed to get at different traits. And if you do, that actually has much more predictive power. So a lot of interviews are actually not very good at predicting who’s going to be good at the job, but they can be made better, and there’s now enough knowledge to say how to design them more effectively.

Jim O’Shaughnessy
And I’m assuming there are a lot of empirical tests that kind of point that way, right?

Spencer Greenberg
Yes, there’s a lot of research on what makes someone good for a job. And it will be dependent on jobs, to some extent. For example, if it’s a salesperson, a trait like extraversion is probably helpful. You know, if it’s a computer programmer, extraversion probably doesn’t help at all. So you do have to think about, well, what are you hiring for?

Jim O’Shaughnessy
Right.

Spencer Greenberg
But across a wide range of different types of jobs, the personality trait of conscientiousness tends to be a good predictor of performance. These structured interviews, like I described, can help predict. One of the best predictors are work sample tests, where you give people real work to do that’s as close as possible to the actual job, have them do it and then grade it. Makes a lot of sense. It’s kind of a dumb idea, in a way: have them do the thing. But it actually is one of the best predictors. And the key there is trying to find a microcosm of the real job, because you obviously can’t embed them in the actual job. But can you pull out a little piece of the job that reflects it, and have them do that as part of the interview process?

Jim O’Shaughnessy
And what role do stereotypes, which we all keep in our minds whether we realise it or not, other priors (“I knew a person just like this, and he turned out to be a real bad egg”)... Is there any way to disambiguate all of the internal biases you as the interviewer might have, and at least be aware or try to counteract them?

Spencer Greenberg
There are some really handy techniques. For example, one that I like to use is you blind yourself to the person’s name when you’re evaluating résumés and things like that. Just take the name off. Why should you see the name? The name is not going to help you figure out who is a better candidate. But the problem with the name is it will give you a picture in your mind of who you’re dealing with. And sometimes you can actually find incredible candidates. If you blind yourself to certain information that is not actually predictive, you can actually find better candidates that others may miss because of their stereotypes and biases, right? So I think that’s one.

I think another is just to understand that, while stereotypes sometimes have some correlation with reality, they tend to be... Well, first of all, they’re unjust, because we’re lumping people in a box. But also, we tend to way overestimate how strong they are. So take an example of men versus women. We did a bunch of research looking at, in the US, what are the biggest personality differences between men and women, and how big are they? And the fascinating thing is, we did find, on average, some differences in self-reported personality between men and women. We also tested people on whether they could predict them. Do they know which ones men are higher on and women are higher on? Yes, they’re pretty accurate. I think about 80% of the time they were able to predict whether men or women were higher, right?

But people thought the effects were so much bigger than they are. The reality is that men and women are these... If you think about it as, like, bell curves, they’re heavily overlapped. Very, very heavily overlapped. But people think that they’re like separated distributions. And that leads to all kinds of weird biases and problems when people are evaluating, let’s say, women candidates for a job that’s not stereotypically done by women, or male candidates for a job that, you know, is not stereotypically done by men.

Jim O’Shaughnessy
And okay, so we know about the problem. What effective ways are there to combat that in an organisation like mine?

Spencer Greenberg
Right.

Jim O’Shaughnessy
Like, I love the blind. I was involved with the Chamber Music Society of Lincoln Center, and for a while they did blind auditions. The musician would play behind the screen. And I thought that the candidates selected ended up being significantly better because of that one intervention. What other types of things would you recommend if we were hiring you as a consultant, right? To get people to run the process in a more advantageous... Because, after all, we’re looking for predictions, right? Is this person going to be good at the job, yes or no? What other types of things would you advocate that we consider?

Spencer Greenberg
Another technique I find useful is grading parts of a person’s application process in the context of other applicants. So, you know, you imagine a spreadsheet where each row is a candidate, and each column is something they did, like something they submitted, or a work trial task, or whatever. You could grade by row. You go across that one person and look at everything they did. And that’s the natural way people want to do it. But actually, it’s often better to grade by column. You say, “Okay, I’m going to compare everyone’s work sample tests side by side and evaluate each of those,” so that instead of focusing on the person who submitted it, you’re focusing on just: well, how well did they do at this particular task, relative to the other candidates?

Jim O’Shaughnessy
That’s a really good idea. Given all the research you’ve done for the book and everything... So we give fellowships at OSV. They’re non-equity. And if you’re a builder, and if you’re a researcher, obviously you get funds to do the research. Is there any particular study that you would like... “Oh, finally it’s going to get funded”? And let’s say it’s for a six-month to 12-month... What kind of study would you design if the funding was appropriate?

Spencer Greenberg
So we run a lot of research studies. Actually, right now we’re running one I’m really excited about on self-improvement, where it’s like a horse race. We’re actually pitting 20 different self-improvement techniques against each other.

Jim O’Shaughnessy
Oh, great.

Spencer Greenberg
And so each participant is going to be randomised to get four of the self-improvement techniques to do for a month, and they’re going to do them. It will just take, like, 12 minutes every morning. And then we’re going to track, and we’re going to see what kind of outcomes on, you know, anxiety, depression, happiness, productivity, all these kinds of things. Because these kinds of studies, where you actually say, “Well, how well do different things work against each other?”, controlled for who the people are, controlled for the amount of time they’re doing, they’re very rarely done, but they’re some of the most pragmatic. They can actually tell us what works in practice. What should you actually advise people to do?

So I’m really excited about that kind of study. And one study in that genre that, as far as I know, has never been done, that I would love to see done, is a study testing different goal-setting approaches. Because setting effective goals and useful goals is really valuable. But I’ve never seen a study that says, “Okay, let’s try different ways of helping people to set goals, and then we’ll track people for three months or six months or whatever, and look at how well did they achieve them, but also how satisfied are they with what they achieved,” and actually see what’s really effective for goal setting.

Jim O’Shaughnessy
It reminds me of what I think is an apocryphal study. They always claim that it was done at Yale or Princeton or Harvard.

Spencer Greenberg
Right.

Jim O’Shaughnessy
It’s always one of the Ivies. And you’ll see them on the listicles on social media. And they say, “We tracked the class of...” and it’s a class from, you know, 40 years ago. And the one I’m most familiar with is, 2% of them were at the top of their profession, happily... I mean, you know, they really laid it on. And what was the only difference between those people and everyone else in the class? They all had written goals. And so I first discovered that, I think, when I was a teenager, and I’m like, “Okay, I’m going to do written goals,” which I did, and it worked out actually pretty well. But that isn’t... You’re the expert. That isn’t a real study, is it?

Spencer Greenberg
I’ve never heard of that study. It sounds too good to be true. You don’t usually see those kinds of effect sizes, where just the 2% who succeeded all did the same thing.

Jim O’Shaughnessy
All of my alarm bells were going off later, when I revisited what I wrote about it when I was younger.

Spencer Greenberg
Yeah, I don’t think that’s true. However, I do think it is really useful, setting goals. And I think a really common mistake people make is that they don’t understand what we call, in our book, their guiding foundations. And if you don’t understand your guiding foundations, it’s hard to set goals that actually get you to where you want to go. So you’ll see a lot of young people set a goal that’s fairly arbitrary, like, “I want to be a lawyer.” Well, why do you want to be a lawyer? “Well, because my parents seem to think it’s a good path for me,” or whatever. They don’t necessarily have a well-articulated view on why this is actually important to them, based on what they fundamentally care about.

And so in The 12 Levers, we spend some of the early time in the book helping people figure out what are the things that are most fundamentally important to them. And then you can build your goals on those guiding foundations, to help make sure they’re moving you towards what you want. It’s really shocking how often someone will spend a decade pursuing a goal, only to get it and be like, “Oh, I’m not actually happy. Why did I do this?” That is a common human experience, and it’s really disturbing.

Jim O’Shaughnessy
I was lucky. My grandfather was a very successful entrepreneur, and I was the youngest grandchild, the martini baby. Thanks, Mom and Dad, for having those martinis. But he was the only grandparent I knew. My others had died before I was born. And so I got to spend a lot of time with him, and he taught me this thing that he called premeditating. And I use it to this very day. I used it when I did the goals, when I was reading that bullshit study. And what he wanted me to do... And I learned it’s incredibly helpful, and I’ll use your “I want to be a lawyer.” What you do is you set, “I want to be a lawyer.”

And then you go down one side of the list, and you say all of the good things that I anticipate will happen if I am a lawyer, if I get to be a lawyer. And then you also have another column of all of the bad things that might happen. And you gotta try to get imaginative. But then he also has you do: you don’t get to be... You end up not graduating law school. What are all the good things that might happen because you didn’t graduate law school, versus all of the... And I found that it unlocks all sorts of things that you don’t even know you’re thinking about. And so it helps to calibrate so much better, because you’re also, you know, learning through via negativa, right?

I have found most of the really beneficial stuff that I surfaced when I do this comes on that side: “I didn’t get to be a lawyer, but...” right? What do you think of that kind of idea?

Spencer Greenberg
Yeah, it sounds like a really useful technique, and it reminds me of the premortem technique, where you basically... You’re about to undertake something, you set a goal, you’re like, “I’m going to go do my PhD,” or whatever it is. And then you think about, “Okay, suppose that this thing fails, or it doesn’t go the way I want and I’m unhappy with the result. Let’s just suppose that’s going to happen. What do I predict the reason will be?” And you kind of write down the different reasons. “Well, maybe it’s because once I get to graduate school, I won’t get along with my advisor.” Or maybe it’s like, “I try to get into PhD programmes and can’t get into them,” or whatever.

You make a list of these kind of predicted ways it’s going to fail, and then you can ask the question, “Okay, what can I do now to help plan in advance to prevent this bad fate?”

Jim O’Shaughnessy
And is part of that because you’re just activating your reticular activating system? And suddenly, you know, it’s like when you buy a new car. Whereas before you’d never seen any Volkswagen Beetles, right after you buy one, all of a sudden all you see are Volkswagens. It has to do, I think, with attention. You could correct me if I’m wrong about that. But the other thing that I wanted your view on is... So in my prior life as an asset manager, we were quantitative, algorithmic factor investors. And one of the things that I continually observed, and tried to guard against as much as I could when I was doing the tests, is what I call honest-minded data mining. In other words, they are not intentionally trying to skew or p-hack, but they end up doing that completely unconsciously.

Are there any methods... I mean, after all, you’ve just put a bunch of systems through the wringer. Are there any ways where you can say, “I think that the research here might need a redo”?

Spencer Greenberg
This ties in a lot to the so-called replication crisis in social science, where, for those who are not familiar, about 20 years ago, many studies were run that, when researchers then tried to redo them (say, “Okay, let me redo the study from scratch”), they didn’t get the same result. And my best estimate is something like 40% of studies from around that time period don’t replicate. So you don’t get the same result if you redo the study. And I think that’s way too much. You know, I think if it was 5%, we’d say, “Okay, yeah, there’s always going to be some of that. That’s expected.” But 40% is a really high rate, and it makes it hard to build on science if 40% of the stuff is junk. How do you build your castle on that kind of foundation? It’s really hard.

Thankfully, there have been a bunch of efforts to try to improve it. I think, actually, we still need a lot more work to make it better. But we do see progress, where p-hacking, where people do these kind of fishy statistical methods to get a result that’s publishable... I think now the norm has shifted, where people view it as more bad, reviewers are more aware of it, people get punished socially more for doing it, and people are doing larger studies to combat it. And so we do see a lot of improvements, where people are really trying to do better research. And I think that there’s progress, but still there’s a lot more room for progress.

We have a project we call Transparent Replications, where, when new papers come out in the very top psychology journals today, we use a random number generator to pick a study from one of those papers, and then we go redo it from scratch. And so, unlike the project that was looking at the old research and saying, “Well, how was it?”, we’re now looking at the research today, the best research coming out of the top journals. And remarkably, what we’re seeing, our initial signal, is that we’re seeing less of that kind of p-hacking that gets a statistically significant result that’s actually a false positive. And we’re seeing more of another issue that is not really on people’s radars. And it didn’t actually have a name. We had to actually coin a name for it. We call it importance hacking. So it’s analogous to p-hacking.

And the way it works is, if you think about, to publish in a top science journal, everyone, what they want to do is come up with something novel or interesting and important. That’s what everyone’s trying to do, but it’s really hard, right? So some people use an easier method. So what are the other methods? Well, one, you could commit fraud, and thankfully few people are willing to do that. Obviously more do it than we would want, but few people are willing to do that. So that’s one thing they could do. Another thing they could do is p-hack, so they get a false positive that looks real. And that’s what a lot of people were doing, unfortunately, knowingly or unknowingly, you know, 20 years ago. But there’s another method to get in a top journal, and that’s importance hacking.

This new idea, which is, they could manipulate the meaning of the result, not necessarily consciously (they might be doing it subconsciously), but basically the reviewers reviewing it think it means one thing, but it actually means another thing. So if you were to redo the paper, you’d get the same result, but it doesn’t mean what you think. And because of that, it’s actually much less interesting, much less important, and would not have been published had they not shifted the meaning of the result. And so we’re actually seeing quite a bit of that meaning shifting.

Jim O’Shaughnessy
That’s fascinating, and I think a really smart measurement to look at. What about the studies, right? So right now, I think large language models have advanced to a stage where they can do a lot of analysis without a lot of hallucination, right? I was reading a thing on my way in today where somebody was saying, “Here’s what it would cost for large language models to review every scientific paper ever published and look for all the things we’ve been discussing.” If a large language model did that with minimum hallucination, obviously guided by a human researcher, what do you think the results would be?

Spencer Greenberg
It’s interesting, because science is really one of the most powerful things humanity has ever invented.

Jim O’Shaughnessy
Totally agree.

Spencer Greenberg
We can discover incredible things. We can make lasers and satellites and computer chips. It’s wild. At the same time, there’s a lot of flaws in science. And so my view is, we shouldn’t pretend that science doesn’t have those flaws. But of course, there’s always a danger of getting the sort of anti-science crowd riled up and being like, “Yeah, science sucks.” It’s like, no, science is incredible.

Jim O’Shaughnessy
Right.

Spencer Greenberg
It’s just that we’re flawed humans trying to do... We’re trying to do this incredible thing, and humans don’t always live up to the incredibleness of what we’re doing, right? We humans have flaws, and we bring them into the work. You know, there’s p-hacking, there’s importance hacking, there’s political bias sometimes in science. So there’s all of these things. So I think if you had a really reliable way of checking every scientific paper, I think you would find an absolutely massive number of errors, and yet still a bunch of areas where science still makes progress. They still are able to build. And it’s sort of like, if there’s too many errors, then maybe that subfield of science won’t be able to prosper.

My personal life’s mission, what I’m trying to do in my life, is try to make psychology a more robust science, to help it be more of a science any way I can, and to then help use that science to improve the world. That’s what I want to do. I think psychology has tremendous potential, and I think it hasn’t really fully lived up to that. There’s some really great work in psychology, but I think there could be way more, with improved methods, better technology, better prioritisation around what topics are studied. So yeah, I’m really stoked about science, even though I see it as very flawed.

Jim O’Shaughnessy
Yeah. And we share that view entirely. I tried to write the book I’m best known for, What Works on Wall Street, following the scientific method. In other words, I disclosed everything I did, because I wanted people to be able to replicate. And a few people did, and it did replicate, most of it. But I’m also somewhat troubled by this kind of bifurcation. We’re talking about the scientific method, right? Which is, you have a hypothesis, you run the tests and then you get your results, right? Feynman was famous for saying, “No matter how beautiful your theory, if the test does not indicate that it’s correct, the test is right, your theory is wrong.” And one of the things that troubles me is you have this kind of break-off branch, which I guess is called scientism, right? “You must believe the science.”

Anyone who tells me the science is settled, immediately I think you don’t really understand the scientific method, because it’s never really settled. Yeah, of course, some of the best laws, you can continue to test, and you’re going to continue to replicate and get the... But what do you think? How does one combat that? Because, as you say, the anti-science crowd is the crowd that terrifies me, right? Because it is responsible for virtually our entire modern life, right? When we discovered the Age of Reason and the Enlightenment, et cetera. How would you go about dissuading someone, maybe just a friend who doesn’t have advanced degrees, et cetera? What would be your pitch to be like, “Yeah, no, no. Science is not always right. In fact, it builds in this method to prove that it’s not always right”? Any other tips for talking to people like that?

Spencer Greenberg
Yeah, I share that frustration, because, yes, on the one hand, the science deniers, they’re causing lots of problems in society by ignoring what’s actually true. But then the scientists, rah-rah science folks, that are like, “No, no, science is right about everything.” Well, first of all, I would just point them to my field, psychology, and be like, “Okay, you do understand that the psychologists themselves are saying that they did decades of work that is not that reliable?”

Jim O’Shaughnessy
Right.

Spencer Greenberg
Listen to them. They’re not full of shit. They’re talking about their own field, and they pay the big price to accept that, right? So yes, we have to admit that science can go off the rails. It’s a human process. It’s fascinating, because there’s certain scientific questions which almost certainly will never be overturned, right? You know, it’s answered to a degree of certainty. It’s very unlikely. However, there can be subtlety around it that could get overturned. Like with quantum mechanics: certain aspects of quantum mechanics, we’ve just proven them. So, not myself, I’m not a physicist, but they’ve been proven with such a level of rigour, you’re like, there’s no way that’s ever going to get overturned. But our interpretation of it could completely change.

Much the same way where, when Newtonian mechanics was the king, people thought, “Oh, we live in a clockwork universe, and there’s determinism.” And then quantum mechanics, which agrees with Newtonian mechanics to a very high degree of accuracy in most situations, is like, “No, no, you’ve been completely misunderstanding everything.” So certainly that could happen. We can’t rule that out. Maybe a new theory of physics comes along and says, “We’re looking at quantum theory the wrong way. Yeah, it’s really accurate, but it’s only an approximation of an even deeper theory.” And the even deeper theory could have a different philosophy of what’s real. So I think that we need to remember that could always get overturned.

But there’s certain experiments that, yeah, they’ve been done so many times, with so many people and so many different varieties, there’s no way they’re going to get overturned at this point.

Jim O’Shaughnessy
And do you distinguish between the hard sciences of quantum mechanics, physics, mathematics, et cetera, where you can at least sort of think, “Yeah, that research result is very well proven”? It reminds me of the old joke about the two bankers talking to one another, and the one says to the other, “Well, we know it works in practice. The problem is, will it work in theory?” But, like psychology... I love, by the way, that your work... because you are trying to bring rigour and empirical results and everything to it. But is there some sort of trait... I mean, what about things where the result of the experiment is always going to be indeterminate, right? How do you deal with that when you’re doing psychological... Like that one person who just was in the study, but, like, a complete outlier. Do you normalise? Do you Winsorise? What do you do?

Spencer Greenberg
So in some ways, studying physics is harder than studying humans, right? You might need to build incredibly precise machines that measure things at, you know, a millionth of an inch precision or whatever, or giant particle colliders. But in other ways, studying physics is easier than studying humans. Every human on Earth who has ever lived has been different from every other human.

Jim O’Shaughnessy
That’s right.

Spencer Greenberg
There is no... You know, every particle is the same of humanity, right? Culture changes, and things that we think are fundamental to humans, it’s like, “Oh, whoops, that was actually just culture,” and you could actually have a totally different culture. And separating out the factors... I don’t know if you’ve heard of the phrase “the crud factor” in psychology. We ran a little analysis where we took thousands of different things that have been measured about humans, and we said, “Just pick two of them at random. What’s the correlation?” And on average, the magnitude of correlation is about 0.1. So, in other words, almost any two random things you pick, they have some correlation, typically. Sure, it’s not zero.

And that means that there’s this incredible morass of everything is related to everything. And trying to pull apart that giant web and figure out what’s really causing what, that’s incredibly hard in this kind of messy world we live in. You know, take an example of childhood poverty, right? Well, childhood poverty could increase anxiety, because maybe people go through really stressful life events due to poverty. It could increase depression, because maybe people don’t feel like their future has hope. Also future income, because starting in poverty makes it more difficult. So you start to see how everything kind of becomes connected to everything else, right? You take one variable, and it’s like, oh, it’s connected in this web. So it’s really hard.

That being said, I’m optimistic. I think with better technology, better methodology and better prioritisation, I really think that we can make more progress in psychology. I don’t think we’re limited just by the difficulty of the field. I think there’s much more we can do to do better.

Jim O’Shaughnessy
And back to the book. If you were going to just say, “Hey, well, you’re gonna...” Because I’m gonna ask you to do it. “Read my book because...” Yeah, give me your pitch.

Spencer Greenberg
Totally. Well, first of all, I just want to give a shout-out to my co-author, Jeremy Stevenson. He’s a psychologist. He treats patients. He also has a PhD in psychology. So, giant shout-out to him. So I’ll tell you why we set out to write this book, because I think it serves as a pitch for the book, which is, both Jeremy and I had tremendously positive experiences with self-improvement, where it really was life-changing. And also, we found it incredibly frustrating, because we read just on our own so many books, and many of them we’d be like, “Was that really worth reading?” Or, “Oh man, I waded through all the stories, and the only thing I got was these, like, two ideas.” And so we both felt there’s so much good stuff.

And also, it can be so frustrating, so confusing. We kept seeing the same ideas with different names, and not realising, “Oh, is that really the same thing or not?” So both of us were really inspired by this idea of, could we write a book where we try to find all the good stuff and put it in one book, and write the book that we wish we had just been able to read? But I don’t think it’s a replacement for the whole self-improvement literature. What it is, is a map that helps you figure out what are all the powerful levers that you can pull to improve your life. And then it also will tell you how to deep dive in any one of those levers. So we have tons of resources. If you’re like, “Lever seven, that’s awesome. That’s really helping me,” we give you really concrete steps you can take. But then we also say, “And if you want to go really deep, here’s some great resources to go really deep on just that lever.”

Jim O’Shaughnessy
And we just mentioned that all humans are different, right? And do you think that there’s any validity to the idea that one of the levers is gonna just perfectly fit me like a glove, whereas if you tried it, it was gonna be a disaster? Walk me through how somebody who reads the book... How do they figure... Because one of the things, again, confirmation bias, right? You’re gonna see something that you already believe, and you’re gonna say, “Oh, okay, I’m going to do more of that,” when what they really need is more of the thing that isn’t confirming their biases.

Spencer Greenberg
So I’ve run over 100 studies on human psychology, and people sometimes ask me, “What’s your biggest takeaway? One thing, if you could point to it.” And so I thought a bunch about that, and I realised my one biggest takeaway of all of it is that our human minds are incredibly different from each other. Much more different than we realise. Like, when we’re sitting in front of another person, most people behave kind of similarly, and we don’t fully recognise that the other person could be having a completely different experience. And so I think that’s absolutely true in self-improvement as well. What works for one person won’t be what works for other people. But some things are still really better than other things, in the sense that they tend to work for more people, for more problems.

And so that’s partly why I think it’s important to have 12 levers, not one lever. It’s like, yeah, different things are going to help for different people. For me, some of the stuff around what we call approaching the monster (so, techniques around dealing with fear effectively), that was transformational for me, because I had a lot of social anxiety. You don’t have social anxiety. You might find a different lever will be much more useful for you. Some people are overactive. They booked their whole schedule to absolutely the maximum capacity. And other people are underactive. They’re just sitting around most of the day doing nothing. And those two people are going to need different things. So we want to give a bunch of powerful levers, but then you’re going to have to do some work to figure out what the right lever is.

And actually, at the back of the book, we made a little decision tree to help map people to the right lever, to help them find what they need.

Jim O’Shaughnessy
And what has been the feedback? Have people come to you and said, “I gave it a shot and I did it for X number of months, and my results were disastrous,” and, you know, why is that? Or are people not over-communicating?

Spencer Greenberg
Well, we do make it clear you might need to try, you know, two or three levers to get the results. I really think that if you put in the effort, you pick a few that are relevant to you and you try them, I do think most people will really see benefits. But thankfully, we’ve been seeing in our reviews that we’ve been getting on Amazon and Goodreads, just review after review where people are saying, “Oh, this really helped me. This changed my life.” Which is awesome and wonderful, but you also shouldn’t take that too seriously, because you can also find people raving about how they drink their own piss and it improved their life. But it is very nice to hear. We love to hear those kinds of stories.

Jim O’Shaughnessy
Yeah. I hope that’s not one of the levers.

Spencer Greenberg
No, definitely not. The 13th lever.

Jim O’Shaughnessy
It’s the 13th lever.

Spencer Greenberg
No, it’s not one of the levers.

Jim O’Shaughnessy
But do not drink your own piss. Yeah, you use that as an example in well-known people giving advice, and then you went and said, “What was the advice?”

Spencer Greenberg
Yeah, there’s this thing that’s so frustrating, and I think we’re all kind of at least somewhat susceptible to it, where we see someone who seems credible, maybe it’s an influencer we like or whatever, and they say, “I tried this thing and it changed my life, and it was amazing.” And I think we feel, as humans, a temptation: “Oh, wow, that changed their life. I should try that thing.” And so I really just wanted to combat that. So I was like, “I’m going to find the funniest examples of people being like, ‘This revolutionised my life. Everyone needs to try this.’” And then you’re like, wait, what did the person do? And there’s literally an example of someone who drilled a hole in their head, and they’re raving about how this is amazing and everyone needs to do it.

Jim O’Shaughnessy
Do you think people really want to change?

Spencer Greenberg
I think that people want to change, but they’re often afraid of giving up something, right? So let’s suppose that you scroll on social media an hour every day after you get home, and you’re like, “I don’t want to do that. It’s such a waste of time,” right? But there’s a reason you’re doing it, right? It’s not like you’re doing it for no reason. So it’s useful to think about what are you getting out of that, right? There probably is some benefit to you. Or even more serious stuff: maybe you haven’t pursued a relationship, and it’s been years and years, and you always thought, “I want to be married,” but you never really meet anyone, right? Your lack of attempting to date is probably doing something for you. Maybe it’s protecting yourself in some way, or avoiding rejection.

Whatever it is, very often our harmful behaviours do give us something that we value. And so it’s useful to understand that, recognise that and say, “Yes, this is giving me something I value, but I can get even more of what I value by swapping it with something else.” But it’s worth acknowledging that we often have fear of change because there’s something we’re getting out of not changing.

Jim O’Shaughnessy
Yeah. And when I was reviewing your other podcasts and things you’ve written, you also touch on mind-body. I’m big on that. I’m a big fan of Dr John Sarno, who practised here at NYU.

Spencer Greenberg
He did a lot of, like, neuroplastic pain research.

Jim O’Shaughnessy
Yeah, yeah. And basically what he concluded was that a lot of physical problems are actually mind in origin. And his thesis was, essentially, as a society, many of us believe that certain emotions are unacceptable to display, and so we repress them. And according to Sarno, our body does not like that, and it compensates for that by giving you a physical symptom.

Spencer Greenberg
Right.

Jim O’Shaughnessy
And he found that only people who were open to the idea that their mind could somehow be involved were the ones that... His cure rate was ridiculous.

Spencer Greenberg
Right.

Jim O’Shaughnessy
There’s a movie that I helped finance called All the Rage, and it’s about Dr Sarno and some of the people in it. I mean, honestly, they’re in wheelchairs, and then the last bit shows them running in Central Park. And it seems miraculous. But he himself was always saying, “This is not miraculous. This is a well-known function.” And he started doing it because he was trained as an MD, and he wasn’t getting any results for the people coming to him in horrific pain. And so he tried to think about what else could be causing this. And I’m bringing this up because of what you said about certain activities that you’re doing must have some benefit to you, or you wouldn’t be doing them.

It might not be the best benefit in the world. But he said that when people did all of his homework and all of that and still didn’t even get better, he made them make a list of the potential secondary benefits of you having, you know, your being unable to move your arm or get up off the couch. And in that, he found a lot of unlocks. Because people were like, “Oh, well, maybe it’s because I crave sympathy,” or, “I want my wife or husband to pay more attention to me,” or any of those things. How do you go about, like, figuring that out in your own studies?

Spencer Greenberg
Yeah, it’s such an interesting topic, and it’s actually one I’ve been working on, an essay, for a while, about exactly this topic of illness that’s connected to our psychology. I think we have to be very careful, because let’s say that someone can’t walk because of a back injury. They got a back injury, now they can’t walk. There will be some subset of them that just need surgery, or there’s some mechanical problem. And then there’ll be some subset of them where none of the surgeries help. You know, basically doctors have nothing that benefits them. And fascinatingly, some fraction of that subset might actually benefit from these psychological ideas. They might discover that actually learning to not resist the pain, learning to not fear the pain that they feel, actually unlocks something. And suddenly they’re getting more mobility back, and suddenly they’re completely better.

And this is a real phenomenon. But I do want to be careful, because I do think we have to be careful about subpopulations, because there are subpopulations where I think the better model of what’s going on is, like, some real physical malady.

Jim O’Shaughnessy
By the way, in all of his work, that’s where he starts.

Spencer Greenberg
Exactly. And you kind of have to narrow down the group and say, “Okay, we’ve eliminated this, eliminated this. Now we’re down to this group, where we’ve ruled out sort of all the physical things. Now let’s explore the psychological.” I think also, people often in that group can... And I really empathise with this. They can feel like they’re being told, “Oh, it’s just in your head. You’re crazy,” or something like this. And so I think it’s also worth emphasising that kind of pain is just as real as any other pain. You experience it exactly like you experience any other pain. It doesn’t feel any different. It’s just a question of, are there psychological unlocks that can reduce the pain? And the answer is sometimes yes. And it’s really interesting how these feedback loops can actually kind of sometimes maybe propagate signals.

And I think one way that can happen is someone can have a mental health challenge. Let’s say severe anxiety, and they’re feeling anxious just most of every day. Maybe they had a really traumatic experience that gave them PTSD, and now they’re just living with constant anxiety. Well, anxiety leads to muscle tension, naturally, most likely because it kind of creates a... When something scary is happening, you want to run away or fight, so you’re kind of tense. But now think about the effects of tensing all day long, every day. Like, oh yeah, you start having back pain, you start having neck pain. And then let’s suppose now you go and you think of it as, “Oh, I have a physical problem.” Now you’re like, “Oh, I should baby my back. I should not do anything that tweaks my neck.” And so now you’re reducing your mobility.

And then, you know, three years go by, and you’re now in this really restricted range of... And guess what happens when you restrict your range of movement? Then you start getting stiffness and soreness, and you’re like, “It’s getting worse.” And they can completely spiral out of control. And for that person, the mental health thing might sit at the top of their... this whole chain of problems.

Jim O’Shaughnessy
Yeah. And that is a classic example of negative compounding, right? You start with, “I’m going to baby this.” And then, “Well, if I move this way, it doesn’t hurt. Or if I sit this particular way, it doesn’t hurt.” And then all of that just feeds all of the rest of it, and you get to a kind of mental prison where nothing is helping. I think one of the things that I would love to do (and some of the fellows that we’ve funded have been actually looking into this) is... Wouldn’t it be great for a general-purpose, robust solution, or at least a way to ameliorate some of the problems, to this? Because I think that, as you mentioned, whenever you say, “Well, maybe this is in your mind,” that drives a lot of people really crazy.

Because, as you mentioned, and Sarno confirms, the pain that you’re feeling is very real. That is not your... You know, that is real. In fact, a woman who died far too young, and was a researcher in this from the medical side, Candace Pert, wrote a book called Molecules of Emotion, in which she said it can actually start a chain reaction of things like neuropeptides, et cetera, flooding your system. So the thing has a mental origin, but has very real physical characteristics that reinforce that idea. I’m interested in what is the thesis of the paper that you’re working on with this particular problem?

Spencer Greenberg
Yes. The essay I’m writing, the goal is to try to catalogue all the different types of physical challenges that can be caused or solved by psychological solutions. So we have these words like “psychosomatic,” right? And actually, psychosomatic, as it’s often used, just means a disorder, like a medical disorder, that is influenced by psychological factors. And if you define it that way, it’s really kind of ridiculous, because you’d be like, well, yeah, a lot of them. Like, maybe more than half. Yeah, maybe most are influenced by psychology, right? You know, people get flare-ups when they’re stressed, or they might have more trouble recovering if they’re anxious, or whatever.

Jim O’Shaughnessy
Dry mouth, if they’re afraid of speaking.

Spencer Greenberg
Yeah, exactly. So it’s not quite the right word. And then we also have this idea of psychogenic illness, which are illnesses that are caused by psychological factors. But the thing I’m most interested in, actually, as far as I know, there is no term for. So I think of it as disorders that could be solved psychologically, either solved or very substantially improved psychologically. And there isn’t really a term for that. So that’s what I’m writing about, this class of disorders. And how do we think about what sort of types there are of them, and subtypes, and what do we make of this? Because I think right now, today, there’s a shockingly large number of people that have pain that I think could be substantially improved psychologically.

Jim O’Shaughnessy
Yeah, well, I look forward to reading that paper, because my Sarno experience was, when I was 37, I got a frozen neck, and I literally couldn’t move my neck beyond that. And so I went to the doctors, as usual. I went to the orthopaedic guys, and they put me in traction. And we were at a bookstore. One of our family traditions was every weekend we would take our kids to a bookstore, and they could spend as much time as they wanted. But the deal was, you can also buy as many books as you want, but you gotta read them. Anyway, one of my younger children was hemming and hawing and couldn’t decide on what she wanted to buy. And so I wandered over to the medical section, and I was looking for stuff on what do I do for a stiff neck.

And that’s where I found Sarno. And I’m like, “Oh, this seems interesting,” because when you look at his bio, he’s an MD, he’s working at NYU. And so I bought the book and I read it. And the first time I read it, I literally threw it across the room.

Spencer Greenberg
You’re like, “No way, this is bullshit.”

Jim O’Shaughnessy
My wife is like, “Why did you do that?” I went, “That is the biggest pile of horseshit I have ever read in my life. I can’t believe that NYU is letting one of their doctors publish this bullshit.” She picks it up and starts looking through it, and they describe personality types and things like that. She goes, “I suggest you read it again.” I did. I ended up reading it like six times. And by the sixth time, I’m seeing myself on every page. But the thing was... And this was the hoped-for outcome, but I wasn’t... I mean, my neck still wasn’t moving... After that sixth read. I woke up, hadn’t done anything different, and completely gone.

Spencer Greenberg
It’s fascinating. I literally, just a few days ago, was talking to a pain researcher, and he was telling me about one of the people that he was interviewing about their experiences. And they literally, just the moment they read about the idea that your pain could just be psychological, this pain that they had for years just went away. Now, that’s not the common case. That’s the weird outlier. But it occasionally happens. It’s almost like the brain can just suddenly be like, “Oh, wait a minute, I don’t have to have pain now. Okay.” Now, unfortunately, usually it’s a lot more work than that, right?

Jim O’Shaughnessy
Yeah, unfortunately. Sarno also talks about those, and he also underlines that these are outliers. But he has several patients who literally just... He would do lectures, and that was a required part of his therapy. And he talks about the rare individual who came to the first lecture, listened, and then, “I’m good. I was ready.”

Spencer Greenberg
I think phantom limb syndrome is such a perfect example here, because it’s this phenomenon where sometimes, when people have a limb removed, they’ll feel a ton of pain in the missing limb, as though it’s still there. Like, they might feel like their fist is still clenched in a really painful way, and they can’t get rid of it. And this wonderful neuroscientist developed this strategy to help them, which is a mirror box, where, through a contraption of mirrors, they put their still-existing arm into the mirror box, and it makes it look like their other arm is there by mirroring it. And then he just has them unclench the fist in the now-mirrored arm, and their brain is like, “Oh, okay, it’s fine now.” And the pain goes away, and it sometimes just cures them essentially immediately.

And what I think it shows is that the brain is doing a lot of processing of information. Somehow, after the arm is removed, the brain is misprocessing the signal, thinking that the arm is still there, in some sense thinking that the fist is clenched when it’s not. But by seeing the arm again, and seeing that it’s unclenched, the brain is just like, “Oh, I can reinterpret the signal now.” And suddenly the interpretation shifts. So it’s a great proof of concept. It’s not the same thing, but it’s a proof of concept that sometimes the brain can just reinterpret a pain signal almost instantaneously.

Jim O’Shaughnessy
Yeah. And kind of perception is reality, right?

Spencer Greenberg
Well, pain, it’s just what you experience. The problem with pain is that it feels bad. And if it felt different, then we would call it something else.

Jim O’Shaughnessy
So what’s the future, do you think, for your work and the work of others? Are we going to be able to get to a place where we can provide the levers and materially help people who want to change? We talked earlier about how some people say they want to change but don’t really want to change. But those who really want to change, what do you think?

Spencer Greenberg
Yeah. So we wrote this book to try to make it easier. But I think technology can really help here as well. For people that buy the book, on our website, 12leversbook.com, we have a little AI bot you get...

Jim O’Shaughnessy
Oh, cool.

Spencer Greenberg
...that you can access, that just helps you apply the techniques from the book. So this is like a little assistant. It’s not a therapist, but it can help you apply the techniques from the book. And I think technology actually has a lot that it can help with, both in helping people put things into action and also helping improve the science. Technology can actually help us do better science on humans. In terms of the application of it, I don’t think we’re at the point where everyone should be using AI as a therapist, but I do think that it can be an assistive tool for your self-improvement journey.

Jim O’Shaughnessy
So I have a thesis that AI might actually ultimately be a better therapist. And the reason I think that is, again, back to human nature. There are a lot of things that could be deep... You could perceive that you have a belief that you treat as a very deep, dark secret, and you’re not even willing to share that with your human therapist, because of all the reasons, right? Embarrassment, or “What are they going to think of me now?”, et cetera. Whereas that’s not a problem, in my opinion, with a large language model. And I’m not advocating doing this now. I’m saying at some point in the future, when a lot of the things are locked down, and the hallucinations and the sycophancy and all of that goes away. What do you think about that idea?

Spencer Greenberg
Yeah, I think the out-of-the-box standard models people use today, like ChatGPT and Claude, I think if you say, “Okay, be my therapist,” I think there’s a lot of problems with that. Sycophancy is a huge problem. A good therapist will not reinforce your false perceptions. They won’t necessarily just immediately say, “Oh, you’re wrong.” They’ll probably do it more delicately. But they will not reinforce your false perceptions. But AIs will absolutely reinforce your false perceptions. And if you are the sort of person, let’s suppose, that you are ruining your relationships but blaming it on other people, the AI will absolutely buy into that and convince you that it’s all everyone else’s fault.

Jim O’Shaughnessy
“It really was her fault.”

Spencer Greenberg
Exactly. And I’ve seen people use it this way. It’s very disturbing. That’s the kind of thing that, with better technology and the right training, maybe they can improve that and make it better. I think they probably can improve that. So I think right now we do have to be careful. One day, yeah, the technology probably will get better and better for this kind of work. And as you point out, there are benefits too. People may not feel comfortable sharing with a therapist. On the other hand, they also may not feel comfortable giving it to some giant company who owns their deepest, darkest secret. So there’s trade-offs here. And what are they going to do with that data, and what’s the privacy on that? I think also there’s other things.

For some things, actually having a human there actually is really important, as a social species. If you’re talking about something that you feel deeply ashamed about, it may be different to have your therapist say, “That’s okay,” you know, versus your AI being like, “That’s okay.” It just may not... You know, we are humans, after all, right?

Jim O’Shaughnessy
I’ve written four nonfiction books, all about the market. I’m taking my crack at my first fiction book. And one of the best prompts that I ever wrote... AI is very good at being critical, if you tell it to be.

Spencer Greenberg
Absolutely.

Jim O’Shaughnessy
So I wrote a prompt saying that this is the most intelligent, most erudite, most insightful reviewer of this genre of fiction, and he absolutely hates every chapter of your book.

Spencer Greenberg
That’s funny.

Jim O’Shaughnessy
And, literally, the feedback I got from that model saved me so many dumb things that I was putting into the book. And now, I’m not advocating that for a psychological therapist, but …

Spencer Greenberg
Most people don’t have as thick of skin, where they’re willing to be absolutely blasted by the AI, you know.

Jim O’Shaughnessy
But one of the things that I really thought about was, my wife graduated magna or summa cum laude in journalism. She’s a great editor. And when I wrote my first book, she edited it. And boy, did that cause some rocky times in our relationship, because we were still doing everything on paper back then. And so I would give her something I was very proud of, and then it would come back a sea of red, and I would get upset. I would be legitimately upset, and I would blame her, right? “You just have no sense for any kind of beauty and elegance in writing.” But the point was, we got in a real fight. And obviously, end of story, she was of course completely right. All of her changes were adopted and whatnot. But I used that example to myself, thinking, “I’m not going to get mad at an AI,” right? And so I could take all... And boy, it was really... I mean, it was downright mean.

Spencer Greenberg
Did it hurt a little bit? Did you feel...?

Jim O’Shaughnessy
No. When I first read the first one, I was kind of like, “Oh my God.” But then I thought, okay, if a person said that to me, I’d be really upset. But then I just was like, this is an autocomplete. And so the idea is that it says they’re shit, they’re actually shit, and I really need to redo them, rethink them.

Spencer Greenberg
I think a lot of people could benefit from editing the permanent custom instructions. So, you know, with Claude and ChatGPT, you can put in whatever you want in the moment, but you can also set permanent custom instructions that are always there. And I’ve found a lot of value from that. One thing I tell it is, whenever something is disputed, make the strongest case on all the plausible sides, so that I can see, “Oh, the case for this side, the case for that side,” rather than just giving me one side of the argument. That’s an example. Another is putting in the custom instructions to say that you value the truth more than finding out that you’re right.

Jim O’Shaughnessy
I have that one.

Spencer Greenberg
And always be, you know, brutally honest about the truth. And it actually makes a difference.

Jim O’Shaughnessy
Huge. Yeah. Well, you are so much fun to talk to. I’m looking at my watch here. What, of the 12 Levers, which one surprised you the most?

Spencer Greenberg
One of the biggest surprises to me was, you think that you understand your problems in your life. And the more that I’ve kind of worked with people and researched this, I’ve come to think that actually we often don’t have a full grasp of our challenges, and that actually holds us back. And I don’t mean the challenge you had once you solved it. I mean the kind of recurring challenges that we face. Very often we have less understanding of them than we think. So a simple example would be, let’s suppose you’re getting into fights with your partner. You might think, “Oh, I understand why we’re getting into fights. I want one thing, she wants a different thing.” And that is a level of understanding. But then you might think to yourself, “Well, but other couples I know, they have the same situation. One of them wants one thing, the other one’s the other thing. And yet they’re not fighting about it. They seem to be able to resolve it.”

So that’s the second level of understanding: well, why are we actually not able to resolve it? And maybe it’s because when you bring it up, you start to feel annoyed and she starts to feel annoyed, right? Okay. That leads to a third level of understanding: well, why is it that you’re both getting annoyed in the situation? And so I think this is why, actually, in the very first chapter of the book, we start with Unravel the Causes, which is about what are the techniques to figure out the deeper underlying causes of what’s going wrong in your life.

Because we often stop at the surface-level solutions, and better understanding leads to better solutions. So that, to me, I was surprised about: the power of that really simple idea of going deeper, and how often we fail to do that.

Jim O’Shaughnessy
Yeah. And that ties in with all those other cultural norms, social norms and whatnot. And I found that very instructive. And as well, it’s like, if you can... And staying with your example, if you can convince your partner, “Hey, I just read this great book. We keep fighting about this. Let’s talk a little bit more about it. Like, why do you get pissed? Here’s why I get pissed.”

Spencer Greenberg
Yeah, like going meta. It’s sort of like we were talking about constructive disagreement earlier. If you’re trying to win the argument or convince the other person you’re right, that’s probably what you’ve been doing all that time. If you flip to the meta and say, “Hey, why don’t we have a discussion about why is it that we don’t resolve this? What’s going on, on the meta level? Imagine we’re aliens looking at the situation. What would we observe?” Sometimes that can be more productive, and give you a lot more insight.

Jim O’Shaughnessy
I tried that years and years ago with my wife, and I presented it as, “What would a disinterested observer, sitting here listening to us, think about what we’re talking about?”

Spencer Greenberg
Yeah.

Jim O’Shaughnessy
And she goes, “Is he your disinterested...?” And so I immediately went, “There are two disinterested observers.” And that is kind of a variation of this, and that’s also pretty helpful. It’s why, in certain polling innovations that I think are interesting, because they get the prediction better, instead of asking somebody, “Who are you going to vote for in the midterms?”, they say, “Who do you think your neighbour is going to vote for in the midterms?” And those have actually proven to be far better predictions of the actual outcome.

Well, Spencer, this has been so much fun. I was really looking forward to it. I love your work. I think kudos for being willing to read 100 and... How many was it? 106 you went through?

Spencer Greenberg
Yeah, it was over 100.

Jim O’Shaughnessy
Yeah. That must have been trying, particularly with some of them. If you know the show, our final question is: we’re going to make you emperor of the world, just for a day. Two things you can’t do: you can’t kill anyone, and you can’t put anybody in a re-education camp. But what you can do is, we’re going to hand you a magical microphone. You can say two things into it, and the two things you say are going to incept the entire population of the world. They’re going to wake up whenever their morning happens to be, and they’re going to say, “I just had two of the best ideas ever. And unlike all the other times, I’m going to actually act on these two ideas.” What are you going to incept into the world?

Spencer Greenberg
Yeah. So I think the first would be that, in order to figure out the truth, you have to use methods that reliably create truth. That sounds like a simple idea, but it means that if you believe the people that are charismatic, you’re going to believe what charismatic people say. If you believe what your family tells you, you’re going to believe what your family tells you. And so if you think about the methods we use to arrive at the truth, and we say, “Well, would I endorse that? Would I endorse everyone using that method of figuring out the truth?” Listening to charismatic people, or trusting whatever your family says, it’s obviously not a reliable method in general. So it also shouldn’t be the way that you try to figure out truth. You need more. And so, trying to think of...

I would try to get everyone to think about, well, what are the methods that actually reliably lead to truth? And, for example, if you want to figure out whether something works for humans, the best we have, the best that science has to offer, is basically: randomise people, give it to a bunch of them and don’t give it to another group, and then compare. Every other method is pretty much worse than that. And I think if everyone understood that, why we need methods like that, and why we need to check what it says before we go and believe things, I think we would have a better world. So that would be my first one.

My second would be to reiterate something we were talking about a little bit earlier, which is that we often don’t understand the deeper causes of what’s going on. And we talked about it on an individual level, but I think it actually really applies at a societal level. If we’re trying to solve a problem, like improve homelessness, if you have the wrong causal understanding of what’s going on, it will lead you to be very inefficient at solving the problem, and probably never come close. So I think very often, when people are going about trying to do things in the world, trying to improve the world, they stop at some explanation, and then they just go all in on that explanation. And they need to go deeper and say, “Well, these complex problems, they’re multifactorial, but we really have to understand the different causal drivers, and we need to target the key causal drivers, or we’re never really going to make progress.” So that would be the other one.

Jim O’Shaughnessy
Both are great. I think they would improve the world immeasurably, as will your book. Spencer, thank you so much for joining me on Infinite Loops.

Spencer Greenberg
Thanks so much for having me on.

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“A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become.”

—Rob Henderson, bestselling author of Troubled

Pre-order No One’s Coming to Save You

David Rhoiney was five when his father walked out, forcing David to become the “man of the house.”

Compton, Oakland, Long Beach: no matter where they turned, fear and hunger waited. Long nights in the homeless shelter. Drive-by shootings. Strangers in overalls dragging his mother away. As his world collapsed, David lost hope. No one was coming to save him.

But he could save himself.

When basketball threw him a lifeline, David grabbed it. So began an unlikely journey, one that carried him from living in a Volkswagen Jetta onto the courts of Division I, through the halls of the Naval Academy, into the corridors of national intelligence, and under the watchtowers of Guantánamo Bay. At last, scalpel in hand, David reached the operating room, where he could become the man his family needed.

, a former lawyer, spent several days interviewing David and spoke to dozens of people from his life. The result is Ed’s first book, No One’s Coming to Save You: The Escape of David Rhoiney, out from Infinite Books on 8 December and now available for pre-order.

Ed joins Jim to discuss:

• The time David was forced to fight a schoolyard bully in front of his family.

• David’s unusual experience of the Rodney King riots.

• The note David wrote to God every night.

• The English teacher who changed David’s life in one hour.

• The prep school coach who cancelled David’s credit cards.

• How a five-foot-three kid ended up playing Division I basketball.

• David as a role model for young men.

• The guilt underpinning David’s success.

• The single word that describes David.

• Why Ed’s interview plan fell apart in the first five minutes.

• Why Ed was inspired by Into the Wild and Raiders of the Lost Ark.

• How Ed captured David’s voice.

• Much more!

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

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Links

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Show Notes

Ed William & Jim O’Shaughnessy

• Ed William: Writer, editor, former lawyer and author of No One’s Coming to Save You. Read Rough Cuts

• The book: No One’s Coming to Save You: The Escape of David Rhoiney, out December 8, 2026. Pre-order

• Infinite Books: The publishing imprint behind the book. Infinite Books

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books, Films & Ideas Mentioned

• Into the Wild: The film Ed compares to the Houston chapter, where David almost stops to rest. Into the Wild

• Raiders of the Lost Ark: Spielberg’s “no boring bits” approach that set the book’s pace. Raiders of the Lost Ark

• Mad Max: Fury Road: Ed’s model for a story that never stops moving. Mad Max: Fury Road

• The Pursuit of Happyness and Good Will Hunting: The stories Ed sees as the book’s closest film parallels. The Pursuit of Happyness / Good Will Hunting

• What Works on Wall Street: Jim’s book, which David challenged him on in their first conversations. What Works on Wall Street

• Behaviorism: The mid-century “give me a baby and I’ll make it anything” school Jim cites in the nature-versus-nurture debate. Behaviorism

Highlights

Never Run From a Fight

Ed William

So there’s a scene early in the book where he is getting bullied at school. Big guy. […] And David turns and runs home. Runs, runs. Gets home. “Thank God, I’m back.” This is in Compton. “I’m back at Granny’s. I’m safe.” And Granny’s is just this amazing place where there’s dozens of family members, cousins, uncles, people who... they say they’re related, he doesn’t even know how. You know, just constantly people coming and going. It’s a fortress. And he gets in the gates. He’s like, “Oh, thank goodness, I’m safe, I’m safe.” And his cousin’s there. And his cousin says, “What are you doing here?” And David says, “This guy, he was coming for me.” The cousin says, “What? So what did you do?” And David says: “Well, I ran.” And his cousin says, “Sit there.” So his cousin disappears. David sort of waits at the house, thinking, “What’s going on?” Half an hour later, his cousin and some of their friends pull up in the car, and David’s like, “What’s going on?”

And they’ve kidnapped the bully, and they get him out of the car and say, “David, we do not run in this family. We do not run. You’re going to have to fight this guy.” So they fight him. David gets his ass kicked. And then, you know, the message is he’s not going to run. And for the rest of the story, he isn’t running. Something comes for him... he goes back for them harder. But then there is a point towards the back third of the story where he suddenly realises that approach, he needs to moderate it. It got him this far, but sometimes you have to tactically retreat.

Finding a Style that Suits the Material

Ed William
You know, the style I use in the book is very different from how I write on my Substack. I write about films on my Substack, as sort of my first love, and I actually write in a completely different style there. For the book, it wasn’t so much a conscious decision as... a style emerges that fits the material. You know, in the first draft I was trying to write it the way that I write online, which is a little bit more, maybe not flowery, but cerebral, I suppose.

Jim O’Shaughnessy
Yeah.

Ed William
And it didn’t fit the material. And with the help of Dylan, who was my editor [..] it sort of lands on this style that I wasn’t expecting to land on, but that I think really fits the subject.

Jim O’Shaughnessy
Briefly, what were you expecting, writing your first book, right? What was the transformation like? […] The thing that I love about the book, and the way you chose to write it, was what you just said. I read a lot, and I read a lot of biographies and autobiographies. It’s a very different style. What was it? Was that part of the transformation? It’s just like, “Okay, this is the way I normally write, but this is what I’m hearing, so I’ve got to completely revamp the way this gets written.”

Ed William
Yeah, yeah, I think so. When you look back at these things, you then explain it away in a way that sounds like it was all pre-planned, whereas these things are much more... you’re fucking around and then something sticks, effectively. But after lots of backs and forth with Dylan, and thinking about it, talking about it... So the style is very sort of direct, uncompromising, quite profane, going back to how much David swears. Punchy, quite gritty style, no pretension, hopefully. And there’s four reasons, I think, why we landed on it. The first is that it suits David’s voice. It’s how he speaks. It wouldn’t work if I’m having these long, flowery, cerebral sentences. That’s not him. That’s not him.

Two, it suits the story. You know, the most attractive... I’m sure this is what appealed to you about David’s story initially, is that it is a story. If this read like some dusty journalistic biography of Churchill that my dad’s got in his... you know, the dozens of war biographies my dad’s got in his bookshelf back home, it wouldn’t... I’d be doing his story a disservice.

Jim O’Shaughnessy
Yes.

Ed William
It reads like fiction, but it’s true, is what I wanted it to be anyway. So that was two […] Three is that no one knows who I am. Relatively speaking, more people know who David is, but, you know, the size of David’s audience... I want far more people to read the book. And so the book needed to be something. It couldn’t just be a vanilla, by-the-numbers, routine thing. It needed to feel different. It needed to feel unusual. It needed to feel sort of like, “Huh, this is a new way of approaching this.”

And then the final reason, actually, is that I think David’s arc... There’s a lot of bad stuff going around about young men at the moment, incels and all that sort of stuff. And I think lots of men and young men are looking for a role model. And I think David’s story genuinely is... I’m always hesitant to use the word “inspirational”, because as soon as you say, like, “an inspirational biography”, you think, “Okay, every biography, this is...” Do you know what I mean?

Jim O’Shaughnessy
Yeah.

Ed William
But I think for a certain young man reader, it genuinely is. And I wanted to use a style that was unpretentious and that was direct, and that, you know, younger readers, teenagers, could engage with.

Edited Transcript

Jim O’Shaughnessy
Well, hello, everyone. It’s Jim O’Shaughnessy with yet another Infinite Loops. Today is very special for me because I have my colleague Ed William, who has written an incredible book on an incredible person, David Rhoiney. Ed, welcome.

Ed William
Thank you. Good to be here.

Jim O’Shaughnessy
So let’s start at the beginning. We wanted to figure out how NFTs work, back when they were all the rage. And so, like normal, I said, “Well, let’s do one,” so that way we can learn about it. And... crazy story, I’ll leave that aside. The winning bidder, though, had the opportunity to either come on Infinite Loops as a guest co-host or nominate someone else. He chose to nominate David Rhoiney. I had never heard of David. And after the podcast, literally when we stopped recording, I said, “Will you let me make a movie about you?” And he kind of looked at me like, “You’re a weirdo.”

Ed William
Big question. Yeah.

Jim O’Shaughnessy
It ultimately turned into a book, and I think we made a much better choice making it a book. But let’s start at the beginning.

Ed William
Yep.

Jim O’Shaughnessy
Tell me about how you approach the project. David is a friend of mine and he can be critical. If he doesn’t like something, he will tell you. And, spoiler alert, he loved the book. But please take me from the start all the way through.

Ed William
Yeah, sure. So the way I came into the project was, you emailed me and said, “Do you want to write a book?” And I said, “Yes. What’s the book?” And then we’ll deal with the after effects. After, you introduced me to David, and I was actually in Thailand when I first met him, travelling with my wife, and it was about 4am my time, Thailand time. And we had the call, and I just thought, “I just need to earn this guy’s trust. That’s my main thing.” Had the call, and I thought it went okay. And we agreed that I’d fly over and interview him for five days. He’d tell his story front to back. He’d give me a long list of people from his life who I’d speak to. So that’s what we did. So I went out and I met him, and that seemed to go pretty well.

And then I just started writing, and then here we are.

Jim O’Shaughnessy
So one thing about David that I love is that list he gave you included people who don’t like David.

Ed William
Mm.

Jim O’Shaughnessy
Did that surprise you?

Ed William
It didn’t, because you had told me that’s the type of person David is. And I didn’t get the list till after I’d spoken with him. And actually, I remember before I went, I was very nervous. My background, the listeners probably don’t know, is I was a lawyer before I started writing online, which is how we found each other. And so I’d never done a big interview project before. I’d never done a book before. It’s my first book. So I was so nervous, and I was sort of thinking, “Okay, five days of interviews. The first half day, I’ll just do softball questions, get to know each other. Won’t go into any of the harrowing stuff from his early childhood. We’ll just do it nice and easy so we can sort of get to know each other.”

So I can’t actually remember what the first question I asked was, but within seconds he was telling me about his father leaving him, the gun violence he experienced as a child. He gave this long, incredible... He basically gave his life story in half an hour, with all the nasty bits. So at that point I realised, “Well, okay, this guy’s pretty honest and pretty candid.” So when the list eventually came, I wasn’t surprised that it involved...

Jim O’Shaughnessy
And go into it a little bit, because that’s what made me want to make a movie about him. I found what he overcame in his life to be incredibly inspirational.

Ed William
Yeah. So David was born in Hawaii. He moved to the West Coast, and his first five years were fairly normal. I mean, he can remember very little of them. Then one day... The book starts with his father turning up from a funeral back home. David runs outside, is excited to see his dad, and his dad goes inside. David follows him. His dad and his mum, you can hear them shouting at each other, clothes flying out the window. And then his dad sort of crouches down and says to David, “I’m going. You need to be the man of the house.”

Jim O’Shaughnessy
And how old was he?

Ed William
David was five years old. Yeah, yeah. Tells him, “Need to be the man of the house.” And a lot of the book is the psychological impact that one phrase like that can have on David’s entire life. I mean, that’s very much the framing. His quest to be the man of the house is very much the framing device of the book. So they were in Compton at the time, staying with David’s granny, his mum Dorothy’s mum. And what I actually found really interesting was that this is Compton in the 90s. You know, the chapters in the book go into more detail, we can talk about different anecdotes if you want, but a lot of crazy stuff happens. But actually, for a while, David has really happy memories of this period, because there’s all these colourful characters in the house.

You know, there’s his Uncle Rob, who was an incredible character, and was up to some less savoury shenanigans during the Rodney King riots. David remembers... First, David went out himself and saw an ear lying on the street and was like, “I shouldn’t be here,” so went back home. And then they were watching TV and... David is watching a TV reporter with some looting going on. And then David’s like, “I know this guy,” coming out of that shop, and it’s his Uncle Rob carrying a TV coming out of the shop. He says, “Mom, look at this.” So anyway, he’s got quite fond memories of this period, even though there were some dark sides as well.

Then... David’s mum suffered from really severe bipolar disorder. She has ups and downs. They leave Compton, which is very much where things really start going wrong. They leave Compton, they go to Oakland. One thing leads to another and, I mean, we can get into whatever part you want to get into, but there’s homelessness, there’s, as I say, gun violence, there’s David having to care for his mother. It goes dramatically wrong. I mean, they live in a Volkswagen Jetta before going to a homeless shelter. Yeah.

Jim O’Shaughnessy
One of the things that David told me, which really did strike me, was he reframed. He told me it was as you’ve just described, but he said, “I choose to look at it as I was lucky to be living in a car in California and not New York.” He said, “Because New York, we would have had no heating and we would have gotten frozen out.” One of the things about his attitude which really impresses me is it almost seems like you can throw anything at David and he will figure a way out to either fix it or make it better or take advantage of it. How much of that did you see, both in David and the people you talk to about David?

Ed William
Yeah, he’s resilient. And actually this was one of the things... So when you first pitched me the project, it was just this incredible rags-to-riches story of someone born into horrible circumstances who achieves loads of incredible things. So again, we should say for the listeners, David has this horrible childhood, but it’s not just misery porn. He goes on to achieve some incredible things. He plays two Division I sports at the Naval Academy. He becomes a cryptologist, he becomes a surgeon. I mean, amazing life. So that was sort of the hook that got me into the story. But actually what makes him far more interesting as a character, despite all these amazing things he’s achieved, is that he’s not a superhero. He’s not perfect. And actually he fucks up, like, a lot, as we all do.

He does things wrong, he acts rashly, he has self-doubt, he worries that he’s in the wrong place, he worries that he doesn’t belong. But what’s so interesting about him is that he just does it anyway. And I think you’ve had similar experiences with him when you’ve been socialising with him, where you’ve noticed he’s not wanting to go to certain events and has gone anyway. And yeah, that’s part of who he is.

Jim O’Shaughnessy
Yes. I took David to some events where I had him stay at my home, and he was normal, what I call “normal David”. He saw my Mac Studio and he’s like, “Can I make some videos on this? Because I’m doing this video series.” I’m like, “Sure.” And we told great stories. But then when we flew to the event, on the plane, he just looked at me and he goes, “You know, I’m nervous as hell to do this.” I’m like, “Why?” And he went into it. He was like, “Man, like, where I’m coming from and where you’re taking me are virtually two different worlds.” And then of course, at the end of the event, who is everyone crowding around? David.

Ed William
Yeah, yeah.

Jim O’Shaughnessy
Did you see more of that as you were writing the book, in the way other people interacted with David?

Ed William
Yeah, so obviously not so much how other people interacted with David, just because I spoke to David mainly one-on-one or with the team. But I spoke to a lot of people from David’s life, all the way from high school teachers, basketball coaches, friends of the Naval Academy, people he worked with, mentors, school friends, his next-door neighbour, all kinds of things. And they’d all sort of been sucked into the story of David. You know, they were so excited that a book was being written about him. They were just delighted about it. Yeah.

Jim O’Shaughnessy
What were some of the funnier or unexpected stories that you heard?

Ed William
Unexpected... I wouldn’t say this is one of the funnier ones, but there was a chapter towards... We can get into the style of the book maybe in a bit, because it’s quite fast-paced, fast-paced, fast-paced for various reasons. But he had mentioned that when he leaves the Naval Academy, before he goes on to become a cryptologist, at that point he thought he was going to go into the submarine programme. And he mentioned very briefly that he was sort of feeling a bit burnt out.

And his best friend, a guy called RL, who features in the book, who I spoke to, lived down in Houston, and he’d mentioned that he stayed there for a little bit, just to sort of rest before he goes back into it, which in itself is quite unusual for David. He’s not a man to rest. Anyway, I was planning on mentioning it in a paragraph, just to sort of move the narrative on. And I spoke to David a bit more about it. I spoke to RL, I spoke to RL’s older brother, who’s sort of a basketball legend at the Academy. And I spoke to RL’s mum, Mrs Lewis, who David had spoken really highly of, who was the warmest, so full of Texan charm and just... it was the most delight... I left the call and said to my wife straight after, “That was the most delightful woman I’ve spoken to in my life.” She was just so charming.

But anyway, they all talked about this period when David was living there as incredibly meaningful to them. And David also talked about it as incredibly meaningful for him. And not much actually happens from a story perspective, but the more I talked to them about it, the more it felt important to the story somehow, even though plot-wise it isn’t. And it actually became one of my favourite chapters of the book. It’s David resting for once, which just doesn’t happen. It’s about the halfway mark of the book, David resting. And the chapter slows down a little bit. And there’s lots of really interesting parallels with his childhood growing up in Compton, the connection with family he feels there. And it’s really similar but also really different. Have you ever seen the film Into the Wild?

Jim O’Shaughnessy
Yeah, yeah.

Ed William
So I’m a big film guy, so I couldn’t help but... through the book, different films are popping into my head. And there’s this bit where the submarine programme doesn’t go through. He gets some bad news, which is sort of a recurring theme of the book. And he just thinks for a second, “I could stay here. I’ve got family around me.” Found family, but family around me. “I could just rest.” Barbecues and ball games. Like, he could just take the foot off the gas on a longer-term basis.

And then he just feels like, “No, I need to achieve something. I need to do something. I’ve got some greatness in me, some fire in me.” And he leaves. And that was such an interesting scene. And it made me think as well of, going back to Into the Wild, there’s a scene in it which I still think is so sad, of the old man, I can’t remember the actor who plays him, who the main character finds, and they form this really close relationship. And then the main character, I can’t remember his name, has to go back into the wild. And the old man says to him, “Why don’t you... I could adopt you. I could be my grandson.” And he says, “No, I need to go back out there.” And then the camera sort of lingers on this old man.

And there’s sort of a scene at the end where David’s leaving. And, you know, Mrs Lewis, who he’s so close with, is this lovely woman, and she’s so happy for him that he’s going, but they will... She said to me, “Like, I consider David my son. I consider David my son. Our life was so much richer with him there.” And I just thought it was such a... And this came out of a paragraph that I wasn’t even meaning to write. And it became such an interesting chapter in the book and such an interesting part of his story.

Jim O’Shaughnessy
Yeah. He is such an interesting contrast in personality traits, right? He is very ambitious. He’s very talented. You mentioned he was in cryptography and he solved some big cases. No PhD, right? And so the PhD guys were all like, “Who is this guy? And why should we listen to him at all?”

Ed William
Yeah.

Jim O’Shaughnessy
But the other thing about David that has been a constant through my relationship with him is his just veneration of, and love and need of, family. Talk a little bit about that. His relationship with his mom, which was challenging. His goals, because his mother featured very prominently in why he wanted to achieve.

Ed William
Yeah. And again, to go back to how I thought it was a sort of conventional... conventional is the wrong word. Not a conventional story at all, but a rags-to-riches story. You know, that was what originally got me into it. And another thing that then deepened it and made me far more interested on a character level was his relationship with his mum, which is so interesting. So she raises him and his brother Jonathan alone, because his father leaves. She has, as I said, severe bipolar. And their childhood is moments of shocking dereliction, effectively, of her duty as a mother, but also moments of, like, immense love and immense care. I mean, on two, multiple occasions, there are guns pointed at David or members of the family, and she steps in between them and says, “This isn’t happening.”

You know, when David goes to the... I need to be careful, I’m not giving away too much of the book here, but there is a lot more. But when David goes to the Naval Academy, he sort of has some big fear that he’s leaving her behind. And she’s been going through a really severe... She has not been with them for a year, in mind. She’s been with them in body, but they’ve been caring for her. And he’s so fearful of leaving her. And he sort of sits down and says, “Do you understand what’s happening? I’m going to Annapolis. I’m not going to be here.” And she sort of says, “Son, you’re fine. You go.” And, like, that was it.

So I just think it’s such an interesting relationship, where it’s not as simple as she was a bad mum, she was a good mum. She’s a human. It’s a human, complicated relationship, which is just so much, from my perspective as a biographer, so much more of an interesting angle. And then I think the question that then tied in... So I’m rambling. I’m not sure this related to your original question, but it’s interesting anyway. So the question that I found really interesting to the book was that what David was wrestling with was his...

He knows that the best way he can save her, he can be the man of the house, he can provide for her, is by leaving and making something of himself, whether it’s becoming a basketball player, which were his early hopes, or becoming a surgeon, which is his ultimate hope. And he knows in his heart he can’t help her there. But then there’s also the guilt of: is the best way to help her by leaving her behind? And am I doing this for her or for me? And again, they’re really, like, knotty human questions that I found so interesting to write about, and so ripe for sort of unpacking in the book.

Jim O’Shaughnessy
And another thing about David that I find interesting, and it relates back to the people all gathered around him at the end of the event. One of the titles we considered for the book was Born to Fit Out. And that was one of his lines to me. He was like, “I always felt like I was born to fit out, but then I worried, how will I ever fit in?” And I guess he chose the way of fitting in by just excelling. And I’ve never really met anyone who does the kind of deep dive on a subject, any subject, like David. So let’s bring in his basketball coach, because that was a very important relationship.

Ed William
Yeah. Coach Sladky.

Jim O’Shaughnessy
But it was not always a smooth relationship.

Ed William
Yes, well, yes. So another theme in the book is, you know, he has a father-shaped absence in his life.

Jim O’Shaughnessy
Yeah.

Ed William
And he finds different men, boys, to fit at different times of his life, and sometimes they’re the right fit, sometimes they’re not. I mean, his mum has a sequence of boyfriends, two particularly feature in the book, who are not good to David, not good to his mum. But one of them has a son, a guy called Darren, who features in the book, who’d been in juvie. He personally was up to no good, but he really took David under his wing and said, “David, I don’t want you to do what I’m doing. I want better for you.” Anyway, so, yes. David then meets Coach Sladky at the Naval Academy prep school. Dave Sladky. He died in 2016. I think he’s... And David finds the father he was looking for.

I couldn’t speak to him, he’s passed away, but I spoke to his son Matt, who said how highly his dad spoke of David. And he came from a certain model of basketball training that saw... he was serious on the sort of Xs and Os of basketball, but he saw it as life coaching, basically, as a proxy for life coaching. And he was a huge stickler with cleanliness. He made all his boys turn their socks inside out before they cleaned them. What skin products to use, all these sort of things. He was teaching these boys to become men. And that’s sort of what David found.

He also, actually... So, David, again, this is a fun little bit which I related to. I think everyone, no matter how you’ve grown up, the first time you get money, you spend it. And I did that. Obviously, for David, it was times a thousand. He’d grown up with zero money at all. And then suddenly, when he’s in the Naval Academy, he’s getting a stipend. So he just goes crazy with his first paycheck and racks up credit card after credit card, and all crap that he doesn’t need, basically.

Jim O’Shaughnessy
Right.

Ed William
And then Coach Sladky was a finance nerd, basically, and he drills into David... You know, one of the reasons David’s most known today is as a sort of financial guru on social media.

Jim O’Shaughnessy
Yeah.

Ed William
And it’s Coach Sladky who sort of drilled that into him in the first place, because he said, “I’m cutting off your credit cards. I’m redirecting 50% of your paycheck to this IRA I’ve set up.” Yeah. He then has another coach after, who they have a more confrontational relationship, at Division I basketball, where, you know, David is beset with injuries, and it doesn’t end the way he wanted it to end.

Jim O’Shaughnessy
Yeah. And let’s talk about that for a minute too, because David went from becoming the man of the house at five, living in cars, taking care of his bipolar mother, and then he gets into Annapolis. Talk a bit about...

Ed William
Yeah. Fish out of water.

Jim O’Shaughnessy
But also, how did that happen?

Ed William
Oh, I see. Yeah.

Jim O’Shaughnessy
And then what it felt like for David when he shows up at Annapolis, because he told me... David swears a lot.

Ed William
Yeah. And on that, just before this call, I looked at my notes from my original interviews with David.

Jim O’Shaughnessy
Yeah.

Ed William
The word “fuck” came 1,445 times. Yes. Yeah.

Jim O’Shaughnessy
And so in the expletive-filled story, which was amazing, he tells me about when he first got to Annapolis. And I’m sure he told you the same story, but I’m gonna let you tell it.

Ed William
Well, to go back to the first question, about how he got to Annapolis, right? There was a moment after they’d been homeless where a figure from David’s childhood comes back into his life and brings some trouble with him. And that’s when the shotgun incident I mentioned, when Dorothy steps between David and the shotgun, happens. And at this point, David is... I can’t remember, but he’s not five years old anymore. He’s 10, 11, 12. And he realises, “I need to get... It’s not going to happen to me. I need to get us out of this situation.” And he starts latching on to anything he can as a way to get out. So first he finds art. He has a cousin who draws pictures of Tupac and The Lion King and Biggie and whatever, and he sort of becomes obsessed with painting. And with David, everything’s instrumental. So it’s not just a love of painting. He’s going to become an artist so he can pay for his family. He could buy his granny a house. He can buy his mum a house. That doesn’t work out. He...

Jim O’Shaughnessy
Although, let me interject. He is a very good artist. Yeah, okay.

Ed William
Very talented. He is. Yeah, he is. Maybe if he kept it going, that’s what he’d be doing. You know, if he was...

Jim O’Shaughnessy
I would not put it past him.

Ed William
Yeah, yeah. No, he’s very talented. And actually, the reason that doesn’t go well is because they move again. Another boyfriend, another move, and they lose all their stuff. He loses all his supplies. Anyway, so he’s latching on to various things to try and find his ticket out of there, desperately. You know, he’s flailing around and he stumbles across basketball. And he starts playing at Vets, the local park in Long Beach. He’s in Long Beach at this time, and he’s pretty good. He’s not amazing, but he’s pretty good. Vets pickup basketball is, like, ruthless. You’re on the team if you’re good enough. If you’re not... So he’s turning up and he’s just on the sidelines. He’s never getting… on the side of the court. He’s never getting played. But he enjoys it and he’s decent.

And he’s like, “This could be my ticket out.” So there’s a No Parking sign outside his house. He spends hours and hours and hours shooting against the No Parking sign. Then he starts dribbling the ball to school. Then he finds a mentor and he goes all in on basketball, basically. And he gets better. He gets better. He gets better. He’s still too small. He’s at the time 5 foot 2. You know, he’s hit puberty and he’s still 5 foot 2, and you’re screwed if you’re that small with basketball. So he’s praying and praying that he becomes taller.

Jim O’Shaughnessy
Which he did.

Ed William
Which he did. He did. So he’d write on a piece of paper every night, “God, please make me 6 foot 2 and 220 pounds by the morning.” And every night he’d then get up and look in the mirror and be like, “Shit, I’m still small.” Anyway, he keeps playing, and he does have the growth spurts, and he hustles his way into getting noticed by a Naval Academy recruiter, who comes and says, “You’re good. I think you’d be good on the team.” At this point, David barely knows who the Academy...

Jim O’Shaughnessy
Right.

Ed William
He’s seen the Army-Navy football game on CBS, so he’d sort of heard of the Navy. You know, his father was actually in the…

Jim O’Shaughnessy Marines, I think.

Ed William
Yeah, in the Marines. Yes. So he knows of the military, but it never crossed his mind that he’d go and join, and certainly not as an officer. But he gets recruited, basically. And so he starts off going to the preparatory school in Annapolis... sorry, in Rhode Island. And he arrives and he’s a fish out of water. And one thing he said to me that I thought was quite interesting is that the defining struggle of his childhood, in his words, was poverty. It was, “How am I going to feed myself tonight?” Racism he hadn’t directly encountered, because he was friends with and living in African American neighbourhoods, and his family and friends were African American, and his life was so insular that he wasn’t out in the world enough to experience it directly.

Jim O’Shaughnessy
Right.

Ed William
And it wasn’t until he got out into the big bad world that then poverty no longer becomes a problem. But then he’s realising he’s having to prove himself in a whole another way. Yeah.

Jim O’Shaughnessy
One of the things he said to me that really resonated with me was that he wasn’t really sure how much of it was him, ie, “These people think I’m bad because I’m black,” and how much of it was really... they really thought that.

Ed William
Yes. Yeah.

Jim O’Shaughnessy
And then he told me some stories where, unfortunately, he got confirmation that, yeah, certain people, certainly not everyone, but certain people really did feel that.

Ed William
Yeah.

Jim O’Shaughnessy
And talk a bit about the way he decided to deal with that, because I found that very instructive.

Ed William
Mm. Well, again, I think... to deal with the racism specifically, he was like, “I’m gonna beat them.”

Jim O’Shaughnessy
Yeah. Basically, what he said was, “The only way I can win here is to better, and not just a little better. I have to be significant. I have to be a quantum leap above.”

Ed William
Yeah.

Jim O’Shaughnessy
Yeah. One of the things about David is I think he’s probably one of the top, I don’t know, 20 people that I know who puts more pressure on himself than other people putting pressure on him.

I mean, I spent a weekend with him and his family, and I’m like, “Just calm down. You’ll be okay.”

Ed William
Yeah. He’s relentless. Absolutely relentless. And I think another thing I tried to sort of tease out in the book is that David spent his entire childhood having to fight tooth and nail to prove himself to everyone.

Jim O’Shaughnessy
Not only that, but he had to fight tooth and nail for everything.

Ed William
For everything. Yes, correct. Everything. And he had to throw himself out there aggressively, and he had to do that in the Naval Academy as well. He has to prove himself over and over again. And then there’s a point in the book where he has made it, and he has to calibrate his approach. He has to learn to...

So there’s a scene early in the book where he is getting bullied at school. Big guy. David’s little, and a big sixth grader, who’s a scary guy, everyone’s scared of this guy, I think he’s older than sixth grade, is coming for David at school. And David turns and runs home. Runs, runs. Gets home. “Thank God, I’m back.” This is in Compton. “I’m back at Granny’s. I’m safe.” And Granny’s is just this amazing place where there’s dozens of family members, cousins, uncles, people who... they say they’re related, he doesn’t even know how. You know, just constantly people coming and going. It’s a fortress. And he gets in the gates. He’s like, “Oh, thank goodness, I’m safe, I’m safe.” And his cousin’s there. And his cousin says, “What are you doing here?” And David says, “This guy, he was coming for me.” The cousin says, “What? So what did you do?” And David says: “Well, I ran.” And his cousin says, “Sit there.” So his cousin disappears. David sort of waits at the house, thinking, “What’s going on?” Half an hour later, his cousin and some of their friends pull up in the car, and David’s like, “What’s going on?”

And they’ve kidnapped the bully, and they get him out of the car and say, “David, we do not run in this family. We do not run. You’re going to have to fight this guy.” So they fight him. David gets his ass kicked. And then, you know, the message is he’s not going to run. And for the rest of the story, he isn’t running. Something comes for him... he goes back for them harder. But then there is a point towards the back third of the story where he suddenly realises that approach, he needs to moderate it. It got him this far, but sometimes you have to tactically retreat.. And yeah, I don’t want to give it away, but he does, and it goes from there.

Jim O’Shaughnessy
And it was one of the things we talked about a lot. Literally, he said, “Jim, you live in a different world than I do.” And he’s fascinated, almost like an anthropologist, right? He wants to be able to take in the entire scene, see how people are interacting, but never falsely. In other words, he’ll modify his behaviour, but it doesn’t change who David is. So he might tell somebody that they’re a fucking idiot, but he will do it in a far more polite manner, right? And one of the things about him that really just continued to impress me... I joked to him, I said, “Is Chumbawamba’s ‘I get knocked down, but I get back up again’ your theme song?” And he goes, “A little bit,” right? And, you know, it takes a lot of courage. Just, like, put aside what he was going through. It takes a lot of courage for anyone in life to... I mean, he could have been from a middle-class household with a mom who didn’t have psychological issues, and it still would have taken a lot of courage. Do you think it was that bully moment, or the gun moment, or... Because another thing he said to me, which really stuck with me: when I was staying with him, he showed me a picture from, I think he was probably 14, and there were a bunch of other kids in the picture. And he started pointing to them. “Jail. Dead.” You know. And then he looked at me and he goes, “I knew that if I didn’t take action, and if I didn’t just keep taking action, I was going to end up like them.”

And to me, that kind of courage, under that kind of pressure, under all of the myriad things that were happening in his life... I find the refined David, the surgeon, he still looks at things like, “Okay, what’s wrong with this picture?” And it motivates him to try to solve problems. He’s really good at it, right? And I talk to him once a week via Zoom, and, you know, I said, “So how’s the new job at the hospital going?” And he immediately goes into everything that could be corrected.

Ed William
Yeah.

Jim O’Shaughnessy
And I think that’s one of the reasons why he’s interested in our world, right? Venture investing, that sort of much quicker pace. But talk a bit about his dive into finance, because that was really remarkable to me for a couple of reasons. Number one, David can get to almost anyone. I mean, if Ben Graham were still alive, David would know him. But he also does the deep and heavy work. Talk about how he takes that approach, not just in finance, but his entire life.

Ed William
Yeah, well, the origin of finances is a combination of his childhood, and the amount of money he spanked as soon as he had the ability to spank it, and Coach Sladky’s advice. And David is initially sceptical of anyone. You have to earn David’s trust.

Jim O’Shaughnessy
Yes. Very much.

Ed William
You have to earn... You have to earn it. And so even as Coach Sladky, who he did respect, was telling him all these things, he was still thinking, “I need to look this up myself.” David was doing applied mathematics at the Naval Academy, so he was a maths brain. And so he just did the deep dive. He read every... I mean, you know the textbooks better than I do, but he read every textbook. I’m sure he read your book.

And he does that for every part of his life he goes into. He goes all in. He does nothing else. I mean, even basketball... there was the BNL, the... I think it’s the Burnett Neighborhood Library, near him.

Jim O’Shaughnessy
Right.

Ed William
And he would go there. He’d play basketball every day, and when he couldn’t play, or when it was night or whatever, he’d go to the library and he’d pore over basketball manuals, coaching manuals, training manuals, fitness manuals, whatever. But also, who were the good players locally? Who’s getting name-dropped on the forums? It was quite funny. So he said he was constantly browsing SoCal forums to find the names of the people he needs to be one better than if he’s going to get into college. And actually, I was researching this book, I spent hours and hours on SoCal forums finding the names, and finding when he was mentioned and stuff. But it goes back to the point we said earlier, about he likes a challenge, and... he has a pathological need to win, which is how he’s got as far as he did, and he will go all in.

Jim O’Shaughnessy
And what were some of the surprising things? Obviously you’ve already described how we brought you into the project. What surprised you the most?

Ed William
I’d actually say... I mean, we’ve done a lot on David’s story. I’d never written a book before, so that whole process was surprising, beginning to end. I mean, if I look back at my first draft, which I thought was pretty good at the time... I had a quick look at it earlier, and it is so embarrassing how bad it is. Which I hope is a process every writer thinks about their first draft... I don’t know. You might...

Jim O’Shaughnessy
I certainly did.

Ed William
Yeah, same thing. I suppose I was most surprised, in the writing process, how much of the book comes together in that last 5%. Like the difference between what the book was long past the first draft, when it was effectively 95% done in terms of the structure and that sort of thing, and how much you then squeeze out of the final parts of the process. And actually how the style... You know, the style I use in the book is very different from how I write on my Substack. I write about films on my Substack, as sort of my first love, and I actually write in a completely different style there. For the book, it wasn’t so much a conscious decision as... a style emerges that fits the material. You know, in the first draft I was trying to write it the way that I write online, which is a little bit more, maybe not flowery, but cerebral, I suppose.

Jim O’Shaughnessy
Yeah.

Ed William
And it didn’t fit the material. And with the help of Dylan, who was my editor, who’s like... “Dylan’s your editor? Then your floor’s pretty high.” Like, it’s sort of a... yeah. And it sort of lands on this style that I wasn’t expecting to land on, but that I think really fits the subject.

Jim O’Shaughnessy
Briefly, what were you expecting, writing your first book, right? What was the transformation like? I’ve written four, as you know. I just completed my first fiction, which Dylan is going to tear apart, thank God. And I absolutely... like, you looked at my first attempts, which I was, you know, “Hey, of course, this fiction ain’t so hard.” Oh, they were horrible, horrible. And the thing that I love about the book, and the way you chose to write it, was what you just said. I read a lot, and I read a lot of biographies and autobiographies. It’s a very different style. What was it? Was that part of the transformation? It’s just like, “Okay, this is the way I normally write, but this is what I’m hearing, so I’ve got to completely revamp the way this gets written.”

Ed William
Yeah, yeah, I think so. When you look back at these things, you then explain it away in a way that sounds like it was all pre-planned, whereas these things are much more... you’re fucking around and then something sticks, effectively. But after lots of backs and forth with Dylan, and thinking about it, talking about it... So the style is very sort of direct, uncompromising, quite profane, going back to how much David swears. Punchy, quite gritty style, no pretension, hopefully. And there’s four reasons, I think, why we landed on it. The first is that it suits David’s voice. It’s how he speaks. It wouldn’t work if I’m having these long, flowery, cerebral sentences. That’s not him. That’s not him.

Two, it suits the story. You know, the most attractive... I’m sure this is what appealed to you about David’s story initially, is that it is a story. If this read like some dusty journalistic biography of Churchill that my dad’s got in his... you know, the dozens of war biographies my dad’s got in his bookshelf back home, it wouldn’t... I’d be doing his story a disservice.

Jim O’Shaughnessy
Yes.

Ed William
Should it... It reads like fiction, but it’s true, is what I wanted it to be anyway. So that was two. Three was... well, I’ve forgotten three, but I’ll skip to four. Was that... I’d like to think that... Oh, sorry, I’ll go back to three. Three is that no one knows who I am. Relatively speaking, more people know who David is, but, you know, the size of David’s audience... I want far more people to read the book. And so the book needed to be something. It couldn’t just be a vanilla, by-the-numbers, routine thing. It needed to feel different. It needed to feel unusual. It needed to feel sort of like, “Huh, this is a new way of approaching this.”

And then the final reason, actually, is that I think David’s arc... There’s a lot of bad stuff going around about young men at the moment, incels and all that sort of stuff. And I think lots of men and young men are looking for a role model. And I think David’s story genuinely is... I’m always hesitant to use the word “inspirational”, because as soon as you say, like, “an inspirational biography”, you think, “Okay, every biography, this is...” Do you know what I mean?

Jim O’Shaughnessy
Yeah.

Ed William
But I think for a certain young man reader, it genuinely is. And I wanted to use a style that was unpretentious and that was direct, and that, you know, younger readers, teenagers, could engage with.

Jim O’Shaughnessy
I showed the manuscript to a friend of mine who’s very erudite. He loves to read. He particularly likes to read biographies and autobiographies. And he sat with it and read most of it in a couple hours. And he came back and he went, “What else has this author done?” And I was like, “Actually, this is his first book.” And he goes, “You know, get the fuck out of here.” Because he basically said, “This makes David alive to me.” And he said to me, “I could think...” And he referenced some other biographies, and he said, “This might actually become a new way of writing biography, because it is very different.” I remember when I first read it, I was like, “Whoa, Ed, why the fuck am I giving this guy... Ed, what have you done?” But then the more I read it, the more perfect I found it, because I think you’re absolutely right. Authenticity. You know, everyone talks about it, right? You have to be authentic, you have to be authentic, and very few people pull it off. How did a nice young Brit, with a very different background, how did you manage to write in what I think is a quite incredible and vivid and alive voice that is very much David?

Ed William
Oh, well, thank you. I hadn’t heard that story, so that’s good to hear. Thank you. But I mean, I interviewed David for this project over five days in total. And then again, I read a draft of the book up to him over several days. So I had dozens of hours of interviews with David. Plus, he went through a spurt in 2021 where he did a lot of podcasts. He has a YouTube channel, he posts things on his X. So there’s a lot of David speaking out there. So I did my due diligence. I read that, I listened to that over and over again. I got a transcript, I read it over and over again. I tried to start my scenes, my stories, with what David had told me, word for word, and then I’d change it completely. But it meant that I was building out of something that was true to his voice. I tried to use him as the starting point at all times. I tried to completely extinguish myself from the book, basically. There’s an author’s note, but other than that, I am not in the book. I’m not there. It is David is in the book. With one caveat, in that I just couldn’t help film popping up in the book. So, you know act quotes...

Jim O’Shaughnessy
You know he loves films too.

Ed William
Well, he’s a movie guy as well.

Jim O’Shaughnessy
Right.

Ed William
Exactly. Exactly. So I felt like I wasn’t doing him a disservice by doing that.

Jim O’Shaughnessy
Yeah.

Ed William
So, you know, act titles are film quotes, and films are weaved all the way through. There’s lots of little Easter eggs, little mini quotes or whatever.

Jim O’Shaughnessy
And did you think of it cinematically? Did you think of it that way, in the way you were structuring the story? Because you pointed out that you kind of decided you were going to write it like it was fiction, because there’s a lot of exciting stuff in this story. But was that the vision? Like, “I want to see this on screen”?

Ed William
Yeah, yeah, of course. I tried to visualise it as I went. And I was reading a lot of biographies as I went, but I actually found thinking of different films as I went helped me more, just because that’s how my brain works. I talked about Into the Wild...

Jim O’Shaughnessy
What are some of the other movies that inspired you?

Ed William
Yeah. So I suppose there’s three sort of buckets. It’s a Pursuit of Happyness story. It’s a Good Will Hunting story. It’s, you know, there’s that out. But I think more interestingly, I remember hearing this thing where, when Spielberg made Raiders of the Lost Ark, he was like, “Why don’t we just... don’t include the boring bits? What if it just moves? What if it just keeps on moving?” And I was like, “Well, why does this book need to be 400 pages? Why couldn’t it be 200 pages and keep on moving?” Same with, like, Mad Max: Fury Road. And I said, “God, that would be quite cool to do a biography sort of in that style.”

Jim O’Shaughnessy
Yeah.

Ed William
And then the other thing: I heard someone describe E.T. as, like, a micro epic, in the way that it’s a story about one boy and an alien, and it’s, you know, mini, but something about it, something ineffable about it, is epic. It’s sort of this, like, sweeping tale, human tale. I can’t articulate it better than that. But I was thinking of David’s story as a micro epic, in that it’s just one man’s story. And other biographies I read, like, ended with... I read one biography, which is sort of the closest comp I could find, about... I’ve forgotten his name, but he grew up in bad circumstances, but then it ended with him taking down bin Laden or something. You know, and that is an epic.

Jim O’Shaughnessy
Yeah.

Ed William
And that’s not David’s story. But I tried to find a way to bring the epic into a micro story. I don’t know. That’s a vague answer, but it’s what I was thinking anyway. Yeah.

Jim O’Shaughnessy
And so now that you’ve gotten to sort of live inside David’s head, inside David’s world, if somebody said they bought your book, and they looked at you and they said, “Ed, like, give me the too long, didn’t read. What’s David really like? What’s his essence?”

Ed William
What’s his essence? Relentless. Relentless. In everything. Yeah. Relentlessly ambitious. Relentlessly determined to provide for his family. Relentlessly determined to succeed.

Jim O’Shaughnessy
Relentlessly self-critical.

Ed William
Relentlessly self-critical. Absolutely.

Jim O’Shaughnessy
Relentlessly “I can do better.”

Ed William
Yes, 100%. And so can you.

Jim O’Shaughnessy
Right. Yes. That’s a really important addition, right? And one of the things that I hope the book achieves is, there are a lot of kids out there right now, and they don’t even have to be in his dire circumstances, right? And reading the book, I think, will inspire them: “Wow, look at what he overcame. And, you know, here I am sitting in Greenwich, Connecticut. Mom and Dad are both doing well and helping me with my schoolwork. I better be a little relentless myself.” How much of that do you think is innate versus learned?

Ed William
Yeah, I’ve been thinking about this question a lot recently, because I just have a daughter who’s now 14 months.

Jim O’Shaughnessy
I know.

Ed William
And we have some friends who have daughters who are around the same age. And I think before, I always wanted to think that a lot was nurture…

Jim O’Shaughnessy
Then you had a child…

Ed William
… and I’m quickly realising that there’s probably a little bit more nature in there. My wife and I always joke, because my wife is much more down to earth and a problem solver than I am. I’m a bit up in the clouds. And so I want the baby... I mean, she can be whatever she wants to be, this is a joke, but, like, I always like the idea of our daughter being, you know, like me, loving films or books, or being sort of more cerebral. Whereas Megan, you know, would love our daughter to be scrappy, and out in the world getting stuff done, and grubby knees. And we always joke that, like, Megan’s winning. And I could nurture our little one however I want, but her nature is she wants to be out being scrappy.

So to go back to David, I think he didn’t have the nurture. So does it have to be nature? I’m sort of thinking as I’m talking here, but the only trouble with saying it’s nature is it implies a lack of agency. It implies that you’ve just got what you’re given, which is clearly not true. David’s story is clear evidence against that.

Jim O’Shaughnessy
Exactly.

Ed William
So I don’t know. I don’t know what the answer is. It’s both.

Jim O’Shaughnessy
Yeah. I think epigenetics is an interesting way to look at it. Like, yeah, the gene is there, but it needs to be turned on or off. And I think that your book shows those genes getting turned on, right?

Ed William
Yes.

Jim O’Shaughnessy
The kind of shame he felt when he didn’t fight the bully, and that was brought on by his relative saying, “Yeah, no, we don’t roll that way.” And then he’s like, “Okay.” And that one got turned on. As you were talking, though, it reminded me of the funny story, probably apocryphal, about a British lord who said, “Before I was married, I had six theories on how to raise children and what they would be like.” He goes, “Now I have six children and no theories.”

Ed William
Exactly.

Jim O’Shaughnessy
Because even brothers and sisters raised in the same household... in many studies, they find them to be as dissimilar as the neighbour kid.

Ed William
Interesting. Interesting.

Jim O’Shaughnessy
And so it’s always fascinated me, because, you know, there’s a whole school of thought that we’re blank slates, right? You can make us. In the middle of the 20th century, behaviourism was the dominant school of psychology. And, you know, the practitioners would say, “Just give me six babies. Tell me what you want them to be. If you want him to be a lawyer, I’ll make him a lawyer. You want a doctor, I’ll give you a doctor.”

Ed William
So it was all nurture.

Jim O’Shaughnessy
All nurture.

Ed William
Interesting.

Jim O’Shaughnessy
Guess how that turned out. And, you know, the research on the more nature side, that replicates, that proves out, etc. But like you said, I believe that it isn’t just automatic, right? Agency is required. And you can be the brightest, most gifted, talented individual in the world, and if you are not agentically going after those gifts that you have, they wither and die.

Ed William
Yeah, absolutely. And I think the other thing with David as well is, even though he didn’t have the parental guidance that many of us have, he was very good at identifying an opportunity when he found one, from someone who could fill that role. So one of my favourite things about the book, which again I didn’t realise until I spoke to lots of people and did my research, is that there’s lots of people in David’s life who just appear for one moment, one conversation or whatever, and a combination of their kindness and generosity, and David’s ability to realise “I’m getting something here that I could use”, has such an outsized impact. So, like, there’s one teacher called Ms Schught, who I spoke to. It’s so interesting, because David had told me about Ms Schught, an English teacher. After David had got into the Academy, he needed his SATs to be a certain score. And David likes, unsurprisingly, given everything we’ve said about him, maths and sciences. Black and white.

Jim O’Shaughnessy
Oh, yeah.

Ed William
No bullshit. No floaty, you know, essays which could be right, could be wrong.

Jim O’Shaughnessy
Right, yeah.

Ed William
Right or wrong. So English was never his forte. Never liked it.

Jim O’Shaughnessy
Right, right.

Ed William
And he had to get his English score up. And he was just despairing, because he just thought, “I can’t do this. I cannot do this.” And he told me about Ms Schught as this incredible figure who gave him absolutely everything. You know, he spoke so highly of her as someone who mentored him, gave him just what he needed to get over the line on his English score. And I spoke to her and she said, “Oh, of course I remember David. David was one of the special ones.” She speaks so highly of him. But she said, “I gave him one hour, two hours I gave him. I gave him so little.” And she was shocked that David remembered it with such intensity, because she said, “You know, I really cared for him, but I was doing my job. I just gave him an hour.” But it meant so much to him. And then he keeps on referring to it all the way through his life. Later in life, he needs to pass some tests that had more of an English component, and he goes back and he’s thinking of that moment. He keeps on using that memory throughout his life. Which, yeah, it was cool.

Jim O’Shaughnessy
The thing that I think about a lot with him, to pick up on what you’re saying: he will relentlessly go after something, to a point where... like, I love rabbit holes, as you know, and I will spend days, sometimes weeks, trying to figure something out. He puts me to shame. I mean, honestly, one of the first times, after we became friends, we were chatting with each other, and he starts breaking out all these... “You know, in What Works on Wall Street you say this, but I think if you refer to these papers that I read over here...” I’m like, “Wow, okay, good for you.” What do you think about the multiplicity of his interests?

Ed William
Yeah, that was another thing that sort of hooked me on the story. There’s sort of an aggregate effect of everything he’s excelled at that is just ridiculous, to be honest. And I think it goes back to what you were saying, that he’ll just do the work. He’ll do the deep dive on whatever it is he’s doing. Go back to what you were saying about PhDs: he didn’t have a maths PhD, and he was doing cryptology, and he only got into cryptology at very late notice, because he was planning to do the submarine programme.

Jim O’Shaughnessy
Right.

Ed William
Which in itself is incredibly elite. I mean, there would have been some good chapters in the book if he’d done it.

Jim O’Shaughnessy
Yeah.

Ed William
But that didn’t work out. One of the various setbacks. And he’s like, “Well, what do I do now?” And he chats to someone and gets advised to give cryptology a go, because he’s got a mathematics degree, and he’s barely heard of it. I mean, obviously they would have covered it briefly in the Academy, but it’s not something... And he then goes deep, and PhD people are sceptical, whatever. But then, right before he does medicine, when he’s already accepted medicine as a... he does cryptology for a few years and then switches to do medicine. And his final posting, he’s agreed to do medicine, so he should really be coasting, because he knows he’s not going to be a cryptologist. So he’s put in, effectively, a think tank for about six months. And he has a mentor called Sil Gonzalez, who I also spoke to, who’s an amazing guy, and apparently Sil said that the PhD person came in and was like, “This kid has got it. This kid is smart.” And it’s just because he put the work in.

Jim O’Shaughnessy
Yeah. And what’s interesting too, to me, is he doesn’t have contempt for certification. I mean, after all, he is MD and he has all these advanced certs on robotic surgery and everything else. But it’s sufficient but not enough, would be the way I would put it, with the way David looks at the world.

Ed William
Yeah. There’s an element, of course, of, like, you do it to prove you can.

Jim O’Shaughnessy
Yeah.

Ed William
You know, David is a DO rather than an MD, doctor of osteopathy. And medicine has these arcane things where there’s more MDs than there are DOs.

Jim O’Shaughnessy
Right.

Ed William
DOs are newer. This is slightly less prestigious. So when David is taking his board exams, he’s like, “I’m gonna fucking do the MD exam as well, to prove that I’m as good as these guys.” And of course he nails it. He nails both of them. But yeah, there’s definitely an element of, “Yeah, I’m gonna do it, I’m gonna show him.”

Jim O’Shaughnessy
And then, of course, he goes on for the specialised training. Is that in the book, or no?

Ed William
So the book ends... I was thinking, I wasn’t sure where to end the book. Is this giving it away? I don’t think it’s giving it away, really. The book ends with him in 2017, with him fulfilling the man-of-the-house promise. I’ll say that.

Jim O’Shaughnessy
Yeah.

Ed William
So that’s just when he’s graduating as a surgeon. So we include one surgery scene in the book, but then specialisation afterwards, that’s for the sequel.

Jim O’Shaughnessy
How much of an impact do you think the Navy had on David as a person?

Ed William
As a person? Good question. For his life, enormous. Absolutely enormous. I spoke to his sponsor... They have sponsor parents at the Naval Academy, just people who... they can go for a hot meal and get their washing done, and they’re local. And I spoke to his sponsor mum, a woman named Maureen, and she was a 70s Vietnam hippie protester, you know. And she said to me, “The last thing I ever expected was to have any sort of relationship with a military institution.” And she’s like, “But the difference that it makes to these people’s lives, in terms of how they can go on, even if they don’t stay in the military...”

Jim O’Shaughnessy
Yeah.

Ed William
The network... And I very much found everyone I spoke to from the military was, “He’s one of ours. We’re going to give you everything you need on this man.” So I think on his life, enormous. It made his career. As a person, maybe not as much as you’d think. He’s such a strong personality.

Jim O’Shaughnessy
He is.

Ed William
He’s such a strong personality. And speaking to people from his childhood, I think he was still like that then. I think he has always had that in him. He’s become more confident, certainly, but that comes from success.

Jim O’Shaughnessy
Yeah.

Ed William
So whether it transformed him as a person, I’m not sure it did. It definitely transformed his life.

Jim O’Shaughnessy
He once joked to me that if I was in the military, any branch, he goes, “You’d be in Fort Dun or the...” But one of the reasons we get along so well is I do see a little bit of that, or a lot of that, in him. But what mitigates it for me is he’s right. What I love about him is it wasn’t just what is wrong with it.

Ed William
It’s how he can fix it.

Jim O’Shaughnessy
Exactly. He’s not a yapper. You know, there’s so much of that online, where “this is wrong and that is wrong”, and of course they offer no solution. I don’t honestly think David is looking for wrong. He just notices it quickly because he’s a very bright guy, but then immediately goes into “how do I solve this” mode. And I think one of his annoyances, to use a polite word, is he can see so clearly how what he’s suggesting is a vastly superior way to do it. And he would test those out on me, and I’m like, “You mean they don’t do it that way already?”

Ed William
Yeah.

Jim O’Shaughnessy
And he’s like, “No, they don’t.” And so he is a really interesting mix, to me, of a deeply analytical person but also a deeply emotional person who really cares. And it’s not because he wants it done his way. It’s because he wants his patients to have the absolute best care. He wants the nurses to be on a schedule that is not going to overburden them or overtax them, etc. And so he would run the solutions by me, and most of the time I would simply say, “I just can’t believe it isn’t already done that way.” And then, of course, comes the slew of fucks.

Ed William
Have you noticed... because you’ve been doing these calls for, was it three years, if not more? Have you noticed... Because, you know, David, we should say, is, in relative terms, a young man. I mean, he’s 42 or something.

Jim O’Shaughnessy
Well, from the perch of 66, he’s a child. He’s a baby.

Ed William
And his career’s developed. Have you noticed, like, a change in how those conversations have gone?

Jim O’Shaughnessy
Yeah, he has become much more tolerant.

Ed William
Interesting.

Jim O’Shaughnessy
And it happened in my life too. I, when I was younger, was quite a proselytiser, and it was my way or the highway. You know, it’s like the Eliot poem: “I shall tell you all. I shall tell you,” when the woman looks at him and says, “That isn’t what I meant at all.” And so I noticed that I went through a period where I really became keenly aware of the fragility of all humans, myself included. And I’m seeing that sort of calmer approach with David now. He still gets fired up, there’s no doubt about that, but he is much more patient. I think it’s because he’s been in these systems for so long, he realises, “Okay, incremental. I’ll settle for it. Right? If I can get these five or ten things in, then the system is going to be that materially better.”

Ed William
Yeah. Got to play the game.

Jim O’Shaughnessy
Right. And in earlier conversations he was, as you pointed out, black or white, yes or no, good or bad. And if it wasn’t perfectly good, it was bad. And I definitely got that sense that he has become more wise in that regard. It doesn’t take anything away from his talent, his ambition, etc. And I often wonder, and I want to get your opinion, where do you think David ends up?

Ed William
I’ve wondered this. At one point I thought, you know, would he go into politics? And I think he’d find it too frustrating.

Jim O’Shaughnessy
I think so too.

Ed William
I think he’d find it too frustrating. So it’s interesting, actually, because when I first met David in 2023 (summer was when I flew out to meet him), at the time I thought he was going to be relentlessly all in, exclusively on medicine.

Jim O’Shaughnessy
Yeah.

Ed William
And actually at that time he was thinking of businesses, and he had all these... he was so excited, all these business ideas. Which made me think that there will be a next chapter. What that is, I don’t know. I don’t think it will be medicine forever. I mean, I don’t know enough about the... Presumably there’s a whole medical entrepreneurial world out there in America which I just don’t know about.

Jim O’Shaughnessy
Yeah, there is.

Ed William
So some sort of medical company would be my guess, but I have no idea. But I think he’ll want to find a new mountain to climb. David likes having a mountain to climb. You know, because he was a general surgeon... The book ends in becoming a general surgeon. He went back into training to become a vascular surgeon. You know, he was a cryptologist, he was doing really well, wanted a new mountain to climb. Went into medicine. General surgeon, doing really well, wanted a new mountain to climb. A vascular surgeon, where he’s now doing, by all accounts, very well. I’m sure he’ll find himself a new mountain.

Jim O’Shaughnessy
Yeah. To me... and, you know, he’s very involved. And obviously, I think I asked him once, I said, “Are you extra involved because of the situation?” He said, “Maybe at first, but no. These young people, my children, mean the world to me, and I really want to try to give them everything I didn’t have. But that’s no longer the reason. I genuinely love doing it. I love coaching my son, I love helping my daughter with her gymnastics.” And yeah, he’s just... I wouldn’t say peripatetic, but he needs to be moving.

Ed William
Yeah, absolutely. And actually on that, there’s a moment towards the end of the book where he meets his first daughter, who is his now-wife’s from a previous relationship. But yeah, she’s David’s daughter. And Kim, his wife, says, “I want you to come and meet my daughter.” They’re sort of newish in the relationship, and David is so nervous about it. He’s just thinking about... he knows from his childhood, like, what... Mum’s new man, how much that can fuck you up. And he’s absolutely determined that he’s not going to be that. But he’s really thinking about it. He’s thinking about, “How can I...?” And she was a Peppa Pig nut at the time, so he was like, “Okay, I’m going to, like, talk to her about Peppa Pig.” He was planning his way in, to sort of show that he was... And he was thinking about it so much that he didn’t realise until it happened. He’s like, “You don’t need to, like, think. This is just so... I love this. This is so... This isn’t something you plan for, right? I love this girl, and she’s part of my life.” And he just thinks, “Oh gosh, why didn’t I... why didn’t I have that? Like, who were these men from my childhood who couldn’t see how good this is?” And then, yeah, he’s had two more kids since, and by all accounts is very much the same.

Jim O’Shaughnessy
So if I ask you to write another book... what mistakes did you make on this one? Hopefully you’ll make novel mistakes on the next book. But what mistakes did you make with this one that, obviously, you learn from and won’t repeat?

Ed William
Good question. What mistakes did... I mean, I felt like I was... I don’t know if you find this from your multiple books, but I found writing a book is just a series of existential crises punctuated by, like, brief moments of self-belief, which evaporate the moment you sort of get to the next page.

Jim O’Shaughnessy
Yeah.

Ed William
You know, I think in my first draft I tried to force it into something that the story didn’t want it to be. I tried to put myself in it too much. I needed to sort of swallow my ego, step away from the story, stop trying to impress people, and let the story emerge in the way that it wants to rather than how I want it to.

Jim O’Shaughnessy
Yeah. And have you found that you’re better at getting into somebody else’s head now, after having done this project?

Ed William
I mean, yeah. I haven’t become Derren Brown, but... I wouldn’t say I can read people better or anything. I think I do, like, enjoy thinking about the story potential of people when I meet them and they’ve had interesting lives.

Jim O’Shaughnessy
Yeah, yeah.

Ed William
You know, because suddenly everything’s a potential subject.

Jim O’Shaughnessy
Yeah.

Ed William
Which sounds slightly serial-killery, but... It’s weird writing a book, because it’s both incredibly difficult, long night of the soul stuff, but also, as long as you just get up and keep writing, eventually a book appears.

Jim O’Shaughnessy
Yeah.

Ed William
Like, you just got to keep doing it. You just got to keep on doing it, and be ruthless with yourself, and have a good editor. And so it sort of made me feel like it doesn’t have to be a big... You can just start. I could just start again and just keep writing.

Jim O’Shaughnessy
Yeah. What kind of book would you like to write next?

Ed William
I’ve got two ideas. As I keep saying, I love film, so I’d like to do something film. I’ve got dozens and dozens of film books at home. What? I don’t know. I had some ideas. I’ll speak to you about one idea which I still like, but I’m not sure. I’m trying to find a story that isn’t there in it, maybe. Something film-related, I don’t know what. Or I have been playing around with fiction as well, because I feel like this book is quite a good stepping stone into fiction, because I was trying to think of it with a fiction writer’s mindset. So I don’t know. Another book, yes. What it is, I’m still working that out.

Jim O’Shaughnessy
And I originally conceived of telling David’s story as a movie. This make a good movie?

Ed William
Oh yeah. It’d be an amazing movie. Yeah, yeah.

Jim O’Shaughnessy
Now I’m going to pull a trick on you. As you know, my final question is: we make you emperor of the world, and you can’t kill anyone, you can’t put anyone in a re-education camp, but we give you a magical microphone, and you can say two things into it that are going to incept everybody in the world. Whenever their next morning is, they’re going to wake up and think, “You know, I just had two of the greatest ideas, and unlike all the other times, I’m going to act on them.” But here’s the curveball I’m going to throw at you. I want you to give me two that you think David would give the world.

Ed William
So the book ends with David returning to where he went to medical school, and he does the keynote address at the commencement. The commencement address, is that the phrase in America? Yeah, just the commencement address. And the first thing he says is, “Strive to better.” And the second thing he says is, “Treat everyone...” He said this was advice he got given by a doctor: “Treat everyone as if they’re your mum and dad.” And, like, I really like that. You know, treat everyone as your family. I think that’s what he’d say.

Jim O’Shaughnessy
Yeah, I like that.

Ed William
Be better and treat everyone as your family.

Jim O’Shaughnessy
And when are we releasing the book?

Ed William
The 8th of December. Tuesday, the 8th of December.

Jim O’Shaughnessy
So it’s coming quickly.

Ed William
Yeah.

Jim O’Shaughnessy
Ed, I love the book. I think you did a great job. I love David. So I think everyone is going to love this book.

Ed William
I hope so. Thank you very much.

Jim O’Shaughnessy
Thanks for coming on.

Ed William
Thank you.

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Emma Camp, senior newsletter editor at The Wall Street Journal’s Free Expression, joins us to talk about why Gen Z is dating less and spending more time alone, how therapy culture and helicopter parenting can turn growing pains into permanent labels, why the fix for the housing shortage is more housing, and why she invites everyone she’s met to every party. She also previews her forthcoming book on Gen Z and risk aversion.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Subscribe to The OSVerse to receive your FREE copy of The Infinite Loops Canon: 100 Timeless Books (That You Probably Haven’t Read) 👇👇

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Links

Show Notes

Emma Camp & Jim O’Shaughnessy

• Emma Camp: Senior newsletter editor at Free Expression, The Wall Street Journal’s opinion newsletter, and former Reason magazine editor. Read Free Expression

• Emma’s breakout essay: Her reflection on the 2022 New York Times op-ed that started her career. After My Big Break

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned

• The Grim Old Days by Chelsea Follett: Emma’s reference for how hard life was for the average person before modern markets. Chelsea Follett

• The Genius of the Beast by Howard Bloom: Jim’s reference for what capitalism achieved that earlier systems couldn’t. The Genius of the Beast

• Jefferson Literary and Debating Society: The University of Virginia society where Emma threw a party every Friday. Jefferson Society

• Partiful: The app Emma uses to invite everyone to every party. Partiful

• Sally Rooney: The novelist Emma writes about in her essays on modern relationships. Sally Rooney

• Attachment theory: Emma’s frame for why a secure marriage lets her take more social risks. Attachment theory

• NAR 2025 Profile of Home Buyers and Sellers: The data on first-time buyers reaching a record median age of 40. Coverage

Highlights

On the housing crisis

I am concerned by the increasing popularity of socialism across all groups of people in America, but especially younger people, because I think what’s happened here is that a lot of up-and-coming socialists are very good communicators, and they’re very good at offering kind of simple, utopian-seeming solutions to what are often very real problems. The issue is that the solutions they’re offering, we know, will just make the problem worse. So something like housing is a great example. It is 100% true that we have a housing shortage. We have a huge housing shortage in this country. It is way too expensive to be able to rent an apartment. So many young people can’t afford to move out of their parents’ houses, definitely can’t afford to buy a home of their own.

The average age of first-time home ownership is inching higher and higher. And housing is one of the biggest purchases that people make. It is this huge problem if you can’t afford a place to live. And the socialist answer is: the reason why we have this problem is because of greed. It’s because of greedy landlords, it’s because of greedy developers. And what we need to do is stop them from charging you so much, and then you’ll be able to afford a place to live. When of course the problem is a housing shortage. And so you can artificially lower the prices as much as you want and you will not solve the underlying problem that we have, you know, nine houses for every 10 people or whatever the number is. That cannot erase the shortage.

And the solution is to build more housing. And on that rent control video, where I was sort of making this very basic Econ 101 argument, I saw people in the comments who were like, “Oh, what? So you want us to choose the interests of big companies over people?” And I’m like, okay, so who builds houses? If we need to build more housing, yes, we need to make the environment friendly for the companies who build housing. The people who build housing are housing developers. And if your primary interest is doing whatever will screw over housing developers, you will not get more housing. And so in this case, the interests of housing developers are the same as the interests of American people who need more affordable housing.

And so if your primary goal is just making big businesses angry because you have the sense that wealth is bad, you end up creating environments that hurt less wealthy people.

Don’t be a flake

Emma Camp
Flaking is a scourge. People should be put in the stocks for flaking, in my view. And this goes back to... I think it’s a combination of social risk aversion and this sort of therapy culture belief that you don’t owe anything to anybody, and your primary duty is to yourself, and doing what protects your peace and makes yourself happy.

Jim O’Shaughnessy
Very narcissistic.

Emma Camp
Which I think at its extremes it can be. But I think it is this sort of reflection of: you don’t need a good reason to do what you want to do. And I think that’s so backwards, because you have a duty to other people. And if you tell someone you’re going to be there for them, you go. Unless you are literally running a 102-degree fever, you have to go. And all the time... So last night, my husband and I went out with another couple that we’re friends with, and we’ve been trying to find a date for us to go out together for a long time. And I got back from work and I was like, “I am so tired. I just kind of want to take a shower and curl up on the couch and watch Slow Horses for three hours.” But…

Jim O’Shaughnessy
Great show

Emma Camp
I promised. Fantastic show. But we said we would do this. It would be a grievous social crime for me to cancel all these people at the last minute, even though I don’t really want to go because I’m exhausted. I’ll go. So I got dressed, got back on the subway, and went out, and we had a great time. This is often the thing that people do not realise: the you before the social event is not the same you that’s at the social event.

Every single time, I’m like, “Oh, I can’t believe I agreed to do this thing after work, I’m so tired.” And I actually get there, I have a great time, and I’m so glad I went. And I’m like, “That was great. That was lovely.” So that, I think, is something important for people to remember.

Edited Transcript

Jim O’Shaughnessy
Emma, welcome to Infinite Loops. When I saw your video on rent control not being the greatest thing in the world, I was fascinated for a couple of reasons. Like, as an old... that is sort of like saying the sky is blue, or a variety of those things. But essentially you blew up with that video. But you’re primarily a writer, would you say, or...

Emma Camp
Yeah, yeah, I would definitely say that.

Jim O’Shaughnessy
Which do you enjoy more?

Emma Camp
I enjoy writing more. Writing is the only thing I’ve ever been really good at. It’s the only thing I’ve ever really wanted to do. I have the very stereotypical writer background, which is, like, I was scribbling stories in notebooks when I was eight years old, but that’s just 100% true. I went to a public fine arts magnet school in Alabama for creative writing. It was like LaGuardia, but in Alabama. I was an English major. It’s just what I’ve done. But as it turns out, I’m pretty good at making videos. I guess some years of community theatre paid off. I don’t know. I just have the right vibe on camera, I guess. And I do enjoy... So with writing, I’m often thinking about exploring ideas in a very deep, rich way.

And videos, I feel like, use the other side of my argumentative brain, which is: how can I make a point as simply as possible? And I have a minute to do it, but really I have half a second to do it, because if you don’t get the hook right, people just keep scrolling.

Jim O’Shaughnessy
So what has the reaction been like? And by kind of generation... I mentioned, I saw it and I’m like, well, duh. But was your generation more shocked, or “Really? I didn’t know that”?

Emma Camp
I don’t know. I can’t really tell how old people are based on their very tiny profile photos. I’m not taking stock of this. So I think there are some generational stereotypes, which is people who are old enough to remember the Cold War and remember how awful communism was, or, like, “Yes, obviously Soviet-style controlling of our economy, having these super intense rent control regimes, obviously that’s not going to work, because it never works.” And I think for younger people, there can be a tendency to assume that this just hasn’t been tried yet, and to sort of forget the lessons of the past, which is: no, we did try it and it didn’t work.

And I think there’s just some partisan sorting as well, where it’s sort of a left-coded thing to be in support of rent control now. And young people are slightly more left-leaning. So there’s a little bit of that. But I don’t know, this sounds strange to say, but I found that for me, doing the work that I do, it makes the most sense for me to just do my thing and put it out there and not have Twitter on my phone and not really think that much about how people are reacting to it.

Jim O’Shaughnessy
You know, you bring up politics, and I mentioned, I read all your work, and you seem to me to be a very well-grounded, philosophical, highly literate person.

Emma Camp
Thank you.

Jim O’Shaughnessy
And you wrote, I think your article was called “The Manosphere,” and it was about the various political divides. And I’ve always thought, you know, it’s a circle, right? When you go further and further to the extreme part, you go from socialism to communism and then you get to fascism, and it’s more of a circle. And you know, the old left-right distinctions, as you probably know, come from France. Before the revolution, the supporters of the king sat on the right and the supporters of the revolution sat on the left. And I think that labels are dangerous because, was it Wittgenstein? “When you label me, you negate me.” And I think that those old labels probably don’t work anymore. What would you think about newer labels like control versus freedom?

Emma Camp
Yeah, I don’t like to label myself. This is often something I’m asked. I don’t like labels because I think when you adopt a label, you implicitly sign on to this slate of viewpoints on different policy issues. And there are some labels where I agree with more of the stock policy positions than others, but none enough that I feel comfortable enough to hitch my wagon to that ideology. And I agree with you. I think the left-right dichotomy is not useful for people with a more sort of civil libertarian orientation. There you go, using labels. It is very small-l libertarian of me to think of it this way, but I think it’s so much more revealing where someone is on the authoritarian versus... control versus freedom axis than the left-right axis, because it fundamentally is a personality feature.

I think people kind of have either authoritarian personalities or small-l libertarian personalities, moderate personalities. Are you the kind of person who has whatever set of beliefs you have and thinks that the government really should try to coerce people into living your prescribed best life for them? Or are you the kind of person who’s willing to live and let live, and not have the government control people’s lives as much? And so because of that, I think people on the centre left and centre right have far more in common than they do with the extreme fringes of their, quote unquote, sides.

Jim O’Shaughnessy
Yeah, I think that the average American is kind of a go-along-to-get-along type person. And I always look at New York as not real America. At my old firm, I was in asset management, and every time I would have to travel, I would say to my wife, “I’m going to real America.” And the differences were pretty profound. I mean, places like Mississippi, Alabama, I met the nicest people, who I really didn’t expect to like because, you know, I was steeped in New York and all of the ways that New York thinks and does things. Have you found that, moving first to DC and then New York City?

Emma Camp
Yeah, I think I disagree with you a little bit that New York isn’t real America. I think every part of America is just as real as any other part of America. And being from... I’m from Alabama. I’m from kind of a smallish exurban town outside of Birmingham. The people I grew up around are just as real as the people in New York. And sometimes for me, maybe this shows that I’m in this sort of murky, not super politically categorisable area, but this sort of more conservative, very MAGA kind of stock person that you find in Alabama, I find their worldview just as baffling in many ways as the most strident Mamdani socialist. I don’t really feel fully at home in either place.

And I think they are just as legitimate and just as batty in their own ways. I mean, red-state-level politics are just as crazy as New York City-level volunteers.

Jim O’Shaughnessy
Yeah. And I’ve always thought that if you could imply all of my beliefs from hearing one of them, then I am brain dead, and I have succumbed to the party line. And that is the thing that really concerns me, as one who lived in a different world, pre-internet, et cetera. And maybe it was the Cold War, but the parties, there wasn’t really an ounce of difference between them on Cold War strategy. But when the Berlin Wall fell, the Soviets fell, we started to see this parting of the ways. What do you think? If I was going to say... and again, here we go, labelling... but younger people versus older people. In your piece you were talking about the different political opinions of older people versus younger people. Talk a bit about that in terms of...

Emma Camp
I mean, it’s very hard to make broad generalisations about groups with millions of people. I think there is somewhat of a misconception that younger men are more right-wing than... you know, Gen Z men are more right-wing than millennial men or even boomer men, depending on who you ask. As far as I’ve been able to tell, looking at a couple of surveys, younger men are more left-wing than older men, in the same way that younger women are more left-wing than older women, generally speaking. It shouldn’t be surprising that younger people are slightly more left-wing than older people. This matches with our long-standing cultural stereotypes. So in many ways that’s good news, because it’s like, okay, this current cohort of young people is not unique. They’re sort of like all other humans before them.

I am concerned by the increasing popularity of socialism across all groups of people in America, but especially younger people, because I think what’s happened here is that a lot of up-and-coming socialists are very good communicators, and they’re very good at offering kind of simple, utopian-seeming solutions to what are often very real problems. The issue is that the solutions they’re offering, we know, will just make the problem worse. So something like housing is a great example. It is 100% true that we have a housing shortage. We have a huge housing shortage in this country. It is way too expensive to be able to rent an apartment. So many young people can’t afford to move out of their parents’ houses, definitely can’t afford to buy a home of their own.

The average age of first-time home ownership is inching higher and higher. And housing is one of the biggest purchases that people make. It is this huge problem if you can’t afford a place to live. And the socialist answer is: the reason why we have this problem is because of greed. It’s because of greedy landlords, it’s because of greedy developers. And what we need to do is stop them from charging you so much, and then you’ll be able to afford a place to live. When of course the problem is a housing shortage. And so you can artificially lower the prices as much as you want and you will not solve the underlying problem that we have, you know, nine houses for every 10 people or whatever the number is. That cannot erase the shortage.

And the solution is to build more housing. And on that rent control video, where I was sort of making this very basic Econ 101 argument, I saw people in the comments who were like, “Oh, what? So you want us to choose the interests of big companies over people?” And I’m like, okay, so who builds houses? If we need to build more housing, yes, we need to make the environment friendly for the companies who build housing. The people who build housing are housing developers. And if your primary interest is doing whatever will screw over housing developers, you will not get more housing. And so in this case, the interests of housing developers are the same as the interests of American people who need more affordable housing.

And so if your primary goal is just making big businesses angry because you have the sense that wealth is bad, you end up creating environments that hurt less wealthy people.

Jim O’Shaughnessy
Yeah. And let’s drill down on the “wealth is bad,” right? The real quote is “the love of money is the root of all evil,” not “money is the root of all evil.” Are these educational issues? Are these societal issues? Are these... I mean, if I was going to appoint you the czar of more housing, obviously, I think I know what you’d do, but how would you communicate that? Because what I love about you is your communication style. When I watched your video, I’m just like, oh, she’s going to be a big star. Because you really... That was 60 seconds. How long was it?

Emma Camp
A minute and a half.

Jim O’Shaughnessy
I watched it on Twitter and I’m like, finally. So on the one hand, some people say, well, presentation, that’s meaningless. I think in our era, it’s kind of everything. So what would you build out to persuade people, not to just say, obviously, the big developers are going to be the ones to build that housing? What would you think about... take me through you blocking out a video on trying to persuade people this is really the solution.

Emma Camp
I mean, I think I would do that same kind of basic, logical argument, because I like to think that people can be persuaded with facts, certainly with kind of intuitive arguments. And so this is why I presented the rent control issue by focusing on the housing shortage, because I think everybody can understand, okay, if we literally do not have enough apartments for the number of people who want to live in New York City, that’s going to cause issues. And I don’t even have to bust out a supply and demand graph for people to intuitively get that. It’s like, okay, we need to build more housing, and going from there. You can make a more nuanced argument, because sometimes people say, “Oh, well, why doesn’t the government build housing?”

It’s like, well, when the government attempts to build housing, it takes way longer and it costs way more than when the private sector builds housing. Largely because when the government gets money involved in things, then the unions get involved, and legislators can place these really stringent requirements on the apartments built with public money. And so it just ends up costing much more, because there are all of these regulatory hurdles that private sector builders don’t have to face.

Jim O’Shaughnessy
Right, right.

Emma Camp
There’s also that. And if our primary goal is fixing the housing shortage, we should focus on allowing housing to be built as quickly as possible. And that also means getting rid of some regulations that make it hard to do that, whether that’s height limits or single... or having... I’m not being the most articulate right now, but you can only build an apartment of a certain number of floors if you’re going to have one stairwell, which is sort of a fire safety requirement. But it ends up keeping a bunch of houses from being built that would have been built otherwise. On and on and on. And it’s like, this is how... if the core problem is the housing shortage, here’s how we build as much housing as quickly as possible, and hopefully that would work.

And I think to your earlier point, it feels very counterintuitive oftentimes to make a moral case for why rich people should be allowed to exist. Even just saying that, I realise that people are like, “What is wrong with this person? She just loves billionaires.” And I don’t have this particularly romantic view of the ultra wealthy. But the thing is, when we have free markets in which people are incentivised by the possibility of getting wealthy to technologically innovate, to make better products... I mean, take something like Amazon, right? Jeff Bezos isn’t so... well, let me go back a little bit. I think this comes from a fixed-pie mentality.

Jim O’Shaughnessy
Yes. I completely agree.

Emma Camp
This idea that someone has more than someone else, it’s because they took more than their fair share, when in reality, oftentimes someone has more than someone else because they made the pie bigger for everyone. So Amazon, right? Jeff Bezos is incredibly wealthy, but he created a product that people love. Most Americans are Amazon Prime subscribers. I love that if I need something, I can press a couple buttons on my phone and it’ll show up at my door the next day, cheaply, and I didn’t have to go to the store. There’s a lot of sort of consternation about whether Amazon is bad or not. But people, voting with their behaviour, love Amazon. And if Jeff Bezos could not have gotten wealthy from that, he wouldn’t have created this product.

And so I would much rather live in a world like America where, yes, there is increasing inequality, but the floor for people’s income is also getting higher. So I would much rather live in a world in which the rich are richer and the poor are also richer than live in a world in which there is less inequality, the rich are poorer, but the poor are also poorer. And I think a lot of leftists make these sort of equality-based arguments. They focus on inequality to hide the fact that free markets have actually improved the lives for the worst-off Americans.

Jim O’Shaughnessy
And, you know, equality, right? So equality of opportunity is one thing; equality of outcome, same word, right? But the equality of outcome, we’ve seen, we have hundreds of years, thousands really, if you look at the kings too, of that not being the case. I mean, literally, for most of human history, the average conditions for the average human have been horrible. They’ve been atrocious.

Emma Camp
Oh, absolutely. I was just starting to read... I got an early copy of... a Cato fellow wrote a book called the... I think it’s called The Bad Old Days.

Jim O’Shaughnessy
Yeah, no, I had her on the podcast. Yeah.

Emma Camp
Oh, amazing. Well, I was starting to read that book on my e-reader, my cheaply produced e-reader the size of a credit card, on the subway here. And yeah, she talks about how atrocious the lives of the average person used to be. And this is why I’m so passionate about free markets, at a time where so few people are, because I’m an optimist. When you look at how, 100 years ago, even the life of the average person on earth, even the life of the average American, was just horrendous, when you compare it to today... I mean, when you look at how the vast, vast majority of people lived in crushing, menial poverty, and very few humans today live at that level of poverty.

How did we go from 95% of all humans living in, you know, $2-a-day-level poverty to something like 15 or 20%? Free markets, technological innovation. That’s how we... huge advancements in medicine, that’s how we got there. And if we’ve done it before, then we can use those same tools to do it again and continue improving people’s lives.

Jim O’Shaughnessy
Howard Bloom, in his book on helping capitalism with better PR... actually, it’s a very thoughtful book about how to reorient people around capitalism. But in the beginning of his book, he essentially says every major religion, everyone promised the promised land of milk and honey. And he goes, “I don’t care which religion you look at.” And we’ve had them for a millennium, and we got nothing. We got the case that you just made, everyone living in crushing poverty, et cetera. And then he goes, capitalism did in 300 years what none of these religions that ruled for thousands could achieve.

Emma Camp
Well, okay, I’m going to push back against that, because I’m not sure that major religions are promising prosperity in your earthly life, right? I know most about Christianity, because I am a Christian. But the promises are not that if you follow Jesus, you’ll be super rich, right?

Jim O’Shaughnessy
Unless you’re a megachurch pastor...

Emma Camp
Right? Right. Maybe. Maybe some. Maybe something. But it’s that if you follow Jesus, you’ll have paradise in the next life, right? It’s about how do you come to terms with the suffering that you experience here on earth.

Jim O’Shaughnessy
But let’s talk about that for a minute. Because religious beliefs are, by their very nature, unfalsifiable, right? “Trust me, you’re going to have the best life after this one.” We can’t test that, et cetera. And then you see this religious attitude working its way into politics, right? By that, I mean, they’re appealing to emotion, to...

Emma Camp
I don’t think that’s unique to religion, though. I just think that’s a feature of ideology.

Jim O’Shaughnessy
I agree. Right, right. But in the old days, when the Pope ruled all of Europe with an iron fist, it was only because he was vain that we got the printing press. If you look into the history of the printing press, he made beautiful Bibles, enjewelled, and basically bribed the Pope, because he knew the Pope was vain about having to wear glasses when he gave his sermon. So what did Gutenberg do? He made the Pope a Bible with letters that were this big, so he didn’t have to wear the glasses. And so he got the Church’s authority for the printing presses, and they didn’t know what they were unleashing.

Emma Camp
I mean, people respond to incentives.

Jim O’Shaughnessy
Exactly, right. And so my point is more along the lines of: I worry when people lose context, right? And by that, I mean, I have a lot of context because I’m 66 and I lived through a lot of that Cold War stuff, and I literally watched them tear down the Berlin Wall. And very familiar with the photos of the people, the guard jumping over to escape to freedom, et cetera. And so I worry that the younger generation, not having the context of that... here we’re going to go... I don’t know if you’re a fan of True Detective, but “life is a flat circle,” and we just seem to be going around and around again and again. Eternal recurrence, to good old Nietzsche.

Emma Camp
Yeah. I’m both someone who is concerned for my generation, if I can make such a broad claim as that, and I’m also sceptical of pronouncements that are too dire, that are too “these are going to be the people that ruin everything,” those kind of pronouncements. I think the sliver of this that I will agree with you on is that I think there’s a lot of reflexive anti-Americanism on the left broadly, but I think especially popular with sort of the young people most likely to be socialists. And I think some of that comes from the “wow, the Iraq war was bad, the Iran war is bad,” sort of somewhat reasonable pushback against certain policy that we’ve had.

But I think the problem is when reasonable scepticism of America’s choices becomes this belief that, okay, well, if it says that America’s bad, then it must be true. It almost becomes this conspiracy-level thinking of: everything that I hear that’s good about America is bad, evil imperialist propaganda, and everything that I hear criticising America must be true, because it’s the secret truth that they won’t tell you. And that, I think, is how you end up with young people who are smart enough to know better full-throatedly endorsing terrorist groups. It’s how you get... there was a trend a couple years ago. I don’t think this is representative of young people, but it was crazy that this even happened, of people reading Osama bin Laden’s letter explaining his hatred of America, being like, “Oh my gosh, guys, he’s so right, America’s bad.”

Leaving out the sentences where he’s like, “And also America needs to be destroyed because of gay people and Jews.” In the same way that it’s reasonable to criticise brain-dead reflexive patriotism that does not consider critically things that our nation has done, it is equally ridiculous to have this brain-dead anti-patriotism. And in some ways they’re both equally destructive.

Jim O’Shaughnessy
But again, it requires so much nuance, right? Because I think the short-form videos... your longer works allow you to elaborate much more. Another one of the things you talk about a lot, which I really resonate with, is that it seems that risk aversion is rampant.

Emma Camp
Yes. I will talk about this, because I have a book about it coming out.

Jim O’Shaughnessy
I know. I think you’re really onto something there.

Emma Camp
Thank you. So when you look at all of these kind of discrete trends among people in their twenties, who’s mostly what I’m thinking about when I say Gen Z, because teenagers are a whole other ball game and most Gen Zers are adults... I think, to continue rambling in my preface, a lot of people say Gen Z when they mean 14-year-olds.

Jim O’Shaughnessy
That’s actually Alpha.

Emma Camp
But the actual age band is basically people who are like 29 to like 17.

Jim O’Shaughnessy
Yeah, you’re grown up.

Emma Camp
It’s mostly teenagers at this point. Or sorry, mostly young adults at this point. But you look at these discrete trends: people are dating way less, people are spending way more time alone. People aren’t getting married as much. People aren’t drinking as much. What unites... everybody is using AI therapists, everybody is self-diagnosing themselves with ADHD. What unites them, these trends? And I was thinking about this and it was like: it’s social risk aversion. I think people are afraid of rejection. They’re afraid of being perceived as weird, as cringeworthy. They’re afraid of being judged by other people.

I don’t want to blame too much of it on the phones, because I think that’s far too simplistic. But the threat of anything embarrassing you might do can be recorded, whether that’s you send a girl some messages on Tinder and she thinks they’re stupid and she takes screenshots of them and she posts about them on Instagram, or even just sends them to her friends, or something dumb you do at a party, there’s a photo taken of it. Or even something like you go to a college party and you’re 18 and you’re drinking and someone takes a video or a photo of it, and then you get kicked off the track and field team or whatever it is. This kind of digital panopticon, I think, causes people to sort of put their hackles up.

And I think this kind of temperamental trepidation is keeping people from living rich, full, connected lives. If you’re so afraid that someone will think you’re weird if you invite them to the party you’re going to have, or if you ask them to get lunch with you, it ends up meaning that you don’t take the opportunities for connection. And of course, most people aren’t actually walking around with this ready-to-judge view of other people. This was something I had to overcome, where I would be like, “Oh, I want to invite this person to this party, but, well, they’ll think I’m being overly eager.” And it took somebody, I think maybe it was my boss at Reason, Katherine Mangu-Ward, who was like, “Emma, people love getting invited to parties. Even if they can’t go, no one’s ever going to be like, ‘Gosh, I can’t believe she invited me to that party. What a loser.’” Actually, yeah, you’re right. And now I invite everyone I’ve ever met to every party I throw, and the vast majority of them do not come. And that’s okay. I still get pretty good numbers. I’m more than willing to invite 150 people to a party, because it means I get 30 that show up. And a 30-person party is pretty good.

Jim O’Shaughnessy
And I love the fact that you’re doing that. And that’s one way. But parenthetically, what you’re speaking about, the panopticon, is very true. If social media was around when I was a teenager, permanently cancelled, because... obviously no phones, no internet, nothing. So we got up to a lot of pretty crazy stuff. And because we couldn’t intermediate through screens, right, we did everything in person. How did you find your friend? Well, you drove over to his house. If he didn’t answer the phone, you asked his parents, “Hey, where’s Greg?” And then you went there, and then you finally found your group. But I love the idea that you’re doing a lot of the throwing of parties, because that was the norm for all of human history.

And then the pandemic came along and we get, “I don’t want to go to that party. I might say something stupid,” or whatever. Have you ever had a party that just bombed?

Emma Camp
I’m going to say, well, yes and no. So my party-throwing journey started when I was in my fourth year at UVA. So this would have been right after the pandemic, fall 2021, spring 2022. And I was in a literary and debating society called the Jefferson Literary and Debating Society. It just celebrated its bicentennial. Oldest student organisation at UVA. It’s awesome. And it was founded in a Lawn room at UVA, which are these 1820s dorm rooms designed by Thomas Jefferson himself. It’s very cool. Very cool. And so the society had an endowed room, and they could basically place someone in this room. And so I was selected to be that person.

And part of the deal, it’s like, okay, you don’t have to pay rent, but in exchange you have to throw a party every Friday during the meeting, so people can drink during the meeting, which they can’t do because technically the room that we meet in is university property. There’s some reason why we couldn’t have alcohol in there. And so I had to throw a party every Friday from 5pm to 2am, and I did that. And I got the cheapest booze money could buy. Kroger had a four-for-$3 two-litre store-brand soda deal. So I got a lot of Dr. K, a lot of Citrus Mist-type fake sodas.

And I would get a handle of Dr. James Crow’s Old Crow whiskey and Bowman’s vodka and a 24-pack of PBR and a bag of Franzia Crisp White and a couple bags of chips, and we’d have a great time.

Jim O’Shaughnessy
Shocking.

Emma Camp
It was shocking, yes. And then after I graduated college and I got a real person job, I was like, okay, I want to keep throwing parties, but I think I’m probably a little too big to continue having provisions... Also no ice, everything room temperature, warm, right? I can’t keep doing this. This is too much. And so at the time I was working at Reason magazine, and one of my colleagues there, Peter Suderman, is amazing. He’s a cocktail wizard. And I was inspired by him to start making cocktails. And so my signature thing, the reason why you should come to this party, is that there are very fancy craft cocktails there, and they’re free. And so I started doing that.

But the parties, what I mean, they didn’t bomb, is it started out with... when I first moved to DC, I had some friends from college there, but most of my college friends were a year younger. So not everybody had quite moved to DC yet, which everybody who attends the University of Virginia moves to DC. It’s just how it works. And so I would invite six people from church over. So they were hangouts more than capital-P Parties. And they sort of got larger as my social circle got larger. So it sort of grew over time. I will say the times I’ve been the most disappointed with how things have worked out have been when I’ve had a lot of flakers, which doesn’t happen that often.

It happens more in New York. This is my big complaint about the social scene between New York and DC: when I have 30 people telling me that they’re coming to my party in DC, 30 people show up. And when I have 30 people telling me they’re coming to my party in New York, 20 people show up.

Jim O’Shaughnessy
Yeah.

Emma Camp
And that annoys me. It hurts my feelings when people say they’re coming and they don’t show up. And the party planning app I use has a “maybe” function, which I usually read as people who are not going to go, but they don’t have a good excuse, and so they put maybe. And that’s okay. I understand. That’s how that works. And flaking is a scourge. People should be put in the stocks for flaking, in my view. And this goes back to... I think it’s a combination of social risk aversion and this sort of therapy culture belief that you don’t owe anything to anybody, and your primary duty is to yourself, and doing what protects your peace and makes yourself happy.

Jim O’Shaughnessy
Very narcissistic.

Emma Camp
Which I think at its extremes it can be. But I think it is this sort of reflection of: you don’t need a good reason to do what you want to do. And I think that’s so backwards, because you have a duty to other people. And if you tell someone you’re going to be there for them, you go. Unless you are literally running a 102-degree fever, you have to go. And all the time... So last night, my husband and I went out with another couple that we’re friends with, and we’ve been trying to find a date for us to go out together for a long time. And I got back from work and I was like, “I am so tired. I just kind of want to take a shower and curl up on the couch and watch Slow Horses for three hours.” But…

Jim O’Shaughnessy
Great show

Emma Camp
I promised. Fantastic show. But we said we would do this. It would be a grievous social crime for me to cancel all these people at the last minute, even though I don’t really want to go because I’m exhausted. I’ll go. So I got dressed, got back on the subway, and went out, and we had a great time. This is often the thing that people do not realise: the you before the social event is not the same you that’s at the social event.

Every single time, I’m like, “Oh, I can’t believe I agreed to do this thing after work, I’m so tired.” And I actually get there, I have a great time, and I’m so glad I went. And I’m like, “That was great. That was lovely.” So that, I think, is something important for people to remember.

Jim O’Shaughnessy
I can’t remember which movie it is, but somebody’s talking about someone, like a shirker, like one of yours that says they’re coming and they don’t come. And he’s like, “We live in a society.”

Emma Camp
We do, we do. And I don’t want to be too harsh. I live in Brooklyn, and all of my friends live on the Upper East Side, and so it’s hard to get places. But you know what? I get on the subway for an hour and a half to see my friends on the Upper East Side. Come to see me in Brooklyn.

Jim O’Shaughnessy
When you’re inviting people to parties, do you intentionally try to mix it up? Do you intentionally try to get very different personality types?

Emma Camp
I think it depends on what kind of thing I’m doing. So if I’m just having a big party, there’s a wonderful app called Partiful, which is how I invite everybody. And I just check this box that’s “invite all previous guests.” And so I just kind of roll the dice. And so it’s this huge group of people: people I know from work, people that I know from college, people I know from the internet, someone at a friend of a friend’s party who I hit it off with and whose phone number I asked for. And I just send those out into the ether. I think if I’m having a dinner party where there is a smaller set of guests, or I’m just inviting a couple people over, the strategy can be different sometimes.

I’ve done dinner parties that are discussion-based. So I’ll give everybody an article to read before, and then we talk about it. So it’s like, okay, what people do I know who I think would have a good time discussing this topic? Or something I’ve been trying to do... and I think I’ve had to make peace with the fact that you cannot brute-force this. I’m really trying to have a friend group in New York, because my favourite thing about living in DC is that my husband and I had this group of friends, six or seven friends. We all had a group chat. We all knew each other from college, and we saw each other once or twice a week. And all you would have to do is go into the group chat.

There was this bar that we really like to go to called Galaxy Hut. We’d go, “All right, who wants to go to the Hut tonight?” And a couple people would show up. That kind of cohesive friend group, I feel like in New York... I moved in January. In fairness, I have a lot of great individual friendships, but that kind of friend group feeling, I really want, and I’m trying to cultivate. But I think I have to accept that I can’t just be like, “You, you: we are a friend group now.”

Jim O’Shaughnessy
Here’s the question. We give fellowships. So let’s say I gave you a $100,000 fellowship, and it was for creating, I don’t know, 10 social groups. How would you design that? And by the way, they would have to live on after you were no longer involved. What would the design look like? Would it look a lot like the way you’re doing parties, or would you do it differently?

Emma Camp
I don’t know. I’m just not really sure that the kind of thing I’m trying to do is... I don’t think you can buy it.

Jim O’Shaughnessy
No, I agree.

Emma Camp
I don’t think that...

Jim O’Shaughnessy
I agree. The hundred thousand would be just for you to be able to get the venues to set that up.

Emma Camp
I mean, I feel like there are a good amount of events sort of built to attract people with a certain kind of political or personality orientation. Whether that’s something, I guess sort of apolitically, like run clubs, or the salon where we’re going to have this public intellectual speak and then their fans will come, that can sort of create a social group. Or even something like a church, right? Where it’s people oriented around certain religious beliefs, and then it creates community from there. I just don’t know how I would create...

Jim O’Shaughnessy
You’re doing it right now. You’re designing it, right?

Emma Camp
Well, I just don’t... I think what I’m sceptical of is, I feel like whether or not you want to be friends with someone is so difficult to categorise. And I think that you can have events that might attract the kinds of people who might get along, and then maybe they will become... But I guess what I’m running up against is you can’t make people do things that they don’t want to do.

Jim O’Shaughnessy
No.

Emma Camp
It’s both that you can’t make people go to events they don’t want to go to, but you can’t make the people go to events... Here is the thing that I think holds people back with making friends in New York City. Okay, you and I are talking. We just met. We’re hitting it off. We’re having a great time. In order for this to become a friendship, in order for us to not just never cross paths again after this, one of us has to pull out our phone and say, “Hey, do you want to swap numbers?” And that is hard to do, because it requires kind of revealing that you like this person and you want to keep talking with them and you want to get to...

And it does open yourself up to the possibility of some kind of rejection, because the person will probably not say no, but you have the possibility that someone’s going to be like, “What is this overeager weirdo doing? Gross.” Right? That’s always a possibility. And I used to be the kind of person who was terrified of doing something like that. Even though I’m quite gregarious and extroverted, I still would not do that. At a certain point in my early college career, I remember having a list: what are my goals for the semester? Being “ask one friend to go to lunch.” It was that big of a difficult thing for me to do, because I was so... I just had this...

Jim O’Shaughnessy
What do you think was causing that anxiety?

Emma Camp
I just think I thought that I was just too weird. I think that I just hadn’t quite found my people yet.

Jim O’Shaughnessy
Right.

Emma Camp
And so I think some of this was the accurate perception that some of the people I was around thought I was weird. And I hadn’t quite gotten comfortable enough in my own skin to be like, “That’s fine. That’s your prerogative. I think I’m pretty great.” And I think that being rejected sucks, and it’s hard to pierce that film and just do it. And this is the thing with taking the risk. I didn’t used to do that. And I started doing it basically because I went, “I want to make more friends.”

Jim O’Shaughnessy
Yeah.

Emma Camp
So I started doing it, and now it doesn’t bother me at all. And I always do this. If I like somebody and I’m enjoying talking to them, I go, “Hey, do you want to swap numbers?” And then I invite them to my next party. And people are often shocked when they come to my parties, when they hear me talking about my plans or whatever. They’re like, “Oh my gosh, you’ve only lived in New York for a year. How do you have 50 people in your house right now?” Well, it’s called not caring at all what people think of me.

Jim O’Shaughnessy
See, that is...

Emma Camp
And trusting that people will self-select.

Jim O’Shaughnessy
That is a superpower.

Emma Camp
Yes. I think it is so important for people to accept that they are not everyone’s cup of tea.

Jim O’Shaughnessy
Right.

Emma Camp
And that how you actually find the people who are meant to be your friends is by accepting that the fact that not everyone likes you is a good thing, because it means that you have enough of a personality that people can react against that.

Jim O’Shaughnessy
Exactly.

Emma Camp
And so being distinct in whatever way, just having your personality, will allow people to be like, “Oh, okay, this person has things that I like, I want to hang out with...”

Jim O’Shaughnessy
Yeah, yeah. And back to Bezos: when he was asked about this, what’s the one quality that people should strive for? And it was authenticity. Basically, be yourself, because some people are going to hate you, some people are going to love you, and that’s just the way it works.

Emma Camp
And I think it’s also easier to change certain parts of your personality than you might think, because being yourself is important. But also, what if you don’t have a pleasant personality? I think I genuinely have become more likeable as I’ve gotten older. And I think part of this is that I’ve just become... I don’t know. I think part of it is just growing up. I think for a lot of people, it’s important to not confuse temporary problems that basically stem from needing to grow up, and needing to stop being 17 and start being 23, with basically diagnosable mental health conditions. I think so much of the therapy culture... trend is people confusing...

Like, I’m in high school, and high school is really stressful, and I haven’t quite found the group of people that I like. And I’m feeling lonely and weird and out of place, and maybe because I’m 17, I’m also not being the best version of myself. This must be because I have whatever condition, right? Or because my mom, who I’m clashing with, must be a narcissist, or whatever it is. No, it’s just because being a teenager sucks, and because nobody is the best version of themselves when they’re 17. And you can always grow up.

Jim O’Shaughnessy
Yeah, that is so true. When I was younger, I was basically an overbearing asshole. And literally, I proselytised. It was my way or the highway. And I realised, life punched me in the face repeatedly to say, “No, Jim, there are many other roads that people can take that are equally acceptable.” But I was very lucky to be blessed with really not giving a shit what people thought about me from a very young age. When I graduated from high school and they did the senior class poll, I was voted most radical. And literally, I’m like, I’m not a radical. I’m conservative. But then as you get old, you... at least for me, you begin to understand there is that fragility to a lot of people, yourself included, right?

And what worries me, and it’s something I wanted your view on, and I know you have very interesting views: this creep into making everything a therapy session or a new diagnosis in the DSM, right? Like learned helplessness. Is that real, learned helplessness? I happen to think it is. But is that coming from a place where they’re shy or afraid, or... I’ll let you tell me.

Emma Camp
I mean, I guess there’s sort of two different things here. One is the larger therapy culture, “every feature of someone’s personality is a diagnosable condition” kind of trend. I think something like learned helplessness is almost anti... people who, I think, are somewhat sceptical of the diagnose-everything movement sort of frame a lot of the emotional fragility, risk aversion among people to learned helplessness. I mean, I think on the learned helplessness question, helicopter parenting definitely has something to do with it. I think that if you reach adulthood without ever experiencing real independence, without ever living without adult supervision, yeah, of course that’s going to make you helpless. There was this viral TikTok video the other week, and I sort of had mixed feelings about it.

So it was this mom, and to be honest, she was speaking in a very condescending and grating way. She was like, “My daughter is 17, and she’s decided that she wants to move out when she’s 18 because she’s such a big grown-up, and she decided that she wanted to live in this student housing, and she came to me and asked for help, and I was like, ‘Figure it out, you’re 18, you’re supposed to know things.’” And so she was basically talking about how her daughter had this “I don’t know how to navigate this system, so I’m just going to freak out and assume that my parents should do it for me.” But I also was sitting there and I’m like, how does your 18-year-old not know how to do this?

On the one hand, yes, it is a problem. It is probably good parenting... I don’t have kids, I’m not going to... but it seems to me like good parenting, when your teenager is trying to figure out something that is totally reasonable for them to be able to figure out, to say “figure it out.” But she also was treating it as presumptively ridiculous that her 18-year-old would be able to live outside of her parents’ home, and sort of saw it as, “See, this proves what a big dumb idiot my kid is, that she can’t figure out how to navigate living on her own.” And I’m like, I’m pretty sure most reasonably intelligent 18-year-old girls could move out, right? I’m not saying they have to, right? But if they want to, they probably could. And if your kid can’t figure that out, maybe you’ve contributed to this problem. Why has she never had to figure out anything on her own before? You are the problem, right?

I mean, I don’t know. I went to... so this fine arts magnet school in Alabama I went to had a boarding option, and so I went there from seventh through 12th grade, but I lived there my last three years. And so I kind of left home when I was 15, and it was great. It was fantastic. I entered college knowing how to take care of myself and kind of secure in my own ability to be independent and figure things out.

When I see this sort of online discourse about parents doing things for their college students, I’m like... the idea of my mom emailing a professor, it’s like, are you from Mars? I almost struggle to think that this is a real thing. But I know it must be. Look, I love my parents and I respect them. And there were plenty of times in college where I had problems, where I was like, “Oh, I’m not quite sure how to navigate this challenge I’m facing,” and I would ask my parents for advice.

Jim O’Shaughnessy
Sure.

Emma Camp
About what I should do. But the idea of then my parents stepping in to solve it for me: absolutely mind-boggling.

Jim O’Shaughnessy
It’s continuously infantilising your child, right? Well, I got married very young. I was 22. And we decided, well, what the hell, we got married at 22, we might as well be young parents. So our first child was born at... we were 24. And we talked a lot about how we wanted to raise our kids. And what we ultimately landed on was: our job is to raise great adults. And using that as a control line prohibits all sorts of behaviour. Like this woman, can you imagine that? She thinks she can learn how to move out on her own... And so we couldn’t say “because I said so.” We couldn’t say “my house, my rules.” That isn’t raising a great adult. That’s raising a compliant person. And so I loved your line about “figure it out.”

Because my kids used to use me as... before Google... I read a lot and I retain facts. And so when they had an assignment, they’d just come up and say, “Dad, who was the French representative at the Congress of Vienna ending the Napoleonic Wars?” And of course I knew it was Talleyrand, but I wouldn’t tell them. We had a big bookcase, and I said, “Look it up in there.” And so I was having a talk with my oldest child, who is the very famous podcaster Patrick O’Shaughnessy. And he said, “Honestly, Dad, I think the greatest thing you and Mom did for us was that, because we learned when you go and find Talleyrand, well, you’ve gone through a dozen other interesting characters too, and so you start going down those rabbit holes.”

But I definitely hate, because it really kind of started with my generation, this helicopter nonsense. When cell phones were relatively new, we had a lot of contemporaries that put spyware on their children’s phones.

Emma Camp
Oh, yes. Everyone has Life360.

Jim O’Shaughnessy
When I first saw it, I said, “That is obscene. You will destroy your relationship with your child, because you’re going to blurt out something when you see something that really freaks you out, and you’re going to destroy the trust that you have with your child.”

Emma Camp
Yeah, it’s pretty common to find on sites like Reddit college students who are like, “What do I do about the fact that... I’m an adult, but my parents have this tracking app on my phone, and they get mad if I’m not at my 9am class or whatever.” I’m like, oh my gosh. Look, I do have a hard time telling how common the extreme end of it is. Certainly when you look at surveys about at what age should a child be allowed to be left at home, I think there’s an indication that it’s gone a bit too far. And I think some of this is only possible for the most affluent parents. I had college-educated parents, a pretty normal middle-class family. But when I was 14, during the summers, my parents couldn’t... they didn’t hire a team of babysitters and tutors for us. We were just left alone. And my youngest sister was seven. And then I had an 11-year-old sister, a 10-year-old brother. And we were old enough that we would be fine on our own for the day. And I was 14, I knew how to dial the phone, and so if something went wrong, I could call them, or I could call 911 or whatever, and nothing bad ever happened. We mostly sat around watching YouTube or playing outside.

Occasionally... the closest it was like, “Maybe there should have been a little adult supervision here”: I was maybe 16, and my brother, four years younger, with one of his friends, were playing in the creek near our house, and they caught a crawfish, and they brought it back in a pot. They’re like, “Emma, Emma, can we cook and eat this crawfish?” And I was like, “Yeah, sure, why not?” And then I thought about it a little bit more, and I was like, “Actually, no, you cannot do that.” And I told them. And then my mom was driving home, and she saw them as they were walking down the street to put the crawfish back in the creek. They were like, “Emma said we could eat it, then she said we couldn’t eat it.” And she was like, “Yes, why would she let you do that?” But yeah, it worked out just fine.

And I think, entering college feeling confident in my ability to live on my own... my family was in Alabama, I was in college in Virginia. I don’t think I’m a homesick person by nature, but I was not always thriving at a 100% level in college. But the kind of basic “Can I pay my rent? Can I clean my room? Do I need someone to tuck me in?” That was not a problem I was having.

Jim O’Shaughnessy
Let’s talk about your book.

Emma Camp
Okay. It’s a collection of essays on Gen Z and risk aversion called No Hard Feelings. It comes out with Ballantine Books, and I think August 2027.

Jim O’Shaughnessy
We missed it. We have a publishing division called Infinite Books. We would have loved to have published that book.

Emma Camp
Sorry, Penguin got it first.

Jim O’Shaughnessy
Yeah, too late. Too late for us. Tell me about it. I’ve written four books, all nonfiction. I just finished my first fiction book, which... wow. Fiction is a hell of a lot harder than nonfiction.

Emma Camp
Yes. I don’t think I could write...

Jim O’Shaughnessy
It’s fun. It’s fun. You’ve got to... if you start from first principles: I’m a baby, I understand nothing. I actually programmed an AI prompt to be one of the best and most well-read in the genre that I’m writing. But I also told the prompt that he hates me. Not only what I wrote: he dislikes me as an individual.

Emma Camp
Nice, nice.

Jim O’Shaughnessy
But some of the best criticism that I got for what I wrote came from that prompt, right? Because I’m like, you know, if someone I love said these horribly mean things to me, I wouldn’t forgive them. But this is a machine. And it fits in with the theme of your book. So how many essays? When is the book due? I think we’ve covered pretty much...

Emma Camp
It’s so close to being done. So it’s eight essays, and I’m supposed to turn in my third draft to my editor at the end of the month. So I’m locked in. But it’s so close. We’re basically in line-level edits at this point, which is so nice.

Jim O’Shaughnessy
Yeah.

Emma Camp
But it’s funny. A year ago, I was on book leave doing the actual writing of the thing. So it’s very nice that the actual writing of the thing is done. But of course, with books, there’s a year between when you actually finish it and when it comes out. So we’re going through that now, which is exciting. I’m very much looking forward to the stage in which the book is done and all I have to do is hawk it.

Jim O’Shaughnessy
Well, the capitalist in me would tell you that one of the things Infinite Books, our imprint, does is we collapse that time. It doesn’t take a year when you’re done with a book.

Emma Camp
I don’t mind that it takes a year. That’s more time to hawk it.

Jim O’Shaughnessy
Okay, so what can readers anticipate? And who are you aiming the book at? Will I enjoy it?

Emma Camp
I hope you will enjoy it. So with the essays, I’m sort of trying to bridge the space between memoir and cultural criticism. I think of the book largely as cultural criticism, so I have essays focusing on stuff like therapy culture, AI boyfriends, celebrity worship, marriage, dating, that kind of thing. Both looking at what’s the latest op-ed from The Cut about this that went viral, what’s happening on TikTok, but also what’s happening in the novels people are reading. So I wrote a lot about Sally Rooney novels, because those are very popular literary novels that are focusing on these sort of contemporary relationships. What does this say? Also looking at older works of literature. I have an essay about sexual... in which I write a lot about Lady Chatterley’s Lover, which I would like my parents to maybe skip. It’s like, “You guys can... you don’t have to read that part.”

And then I’m also drawing from a lot of my own experience. So, for example, with the therapy culture essay: I went through a rough patch during Covid. I was 20, and I convinced myself I had autism. And that was sort of how I explained the problems I was having. I was like, “This is it. This proves that it’s not my fault, right? It’s not because of some deep deficiency within myself. It’s because of this lifelong condition that was going to be this way forever.” And both how I came to believe that, but also how I came to then start questioning whether that was actually right. So I glommed onto this label, and then almost immediately after, I hit my stride, and I found my people, and I was like, “Wait a second. This identity label was supposed to explain why I don’t have friends, and now I have a lot of friends. Wait a second, maybe something else was happening here, and I was giving this permanent name to a temporary problem.” So I was writing about that.

My essay on marriage obviously has a lot about how I came to be the kind of person who got married at 24, which is pretty rare among people of my age group, and has...

Jim O’Shaughnessy
You’re three years in, right? Your marriage?

Emma Camp
Yes.

Jim O’Shaughnessy
How has that changed you?

Emma Camp
How does that change me? It makes my life better in every way. I know. It’s pretty great. 10 out of 10. I think always having someone there, and having the security of that, is so wonderful. I was almost thinking about attachment theory, which is sort of this idea that in order for children to explore the world and be able to take risks, they need to have a secure base, which is normally a parent. I think almost in my adult life, when you have a really rich, stable, loving marriage, I can take more social risks because my husband is always there. And in the same way for him with me. He’s always there at the end of the day for me to talk to. I can talk to him about anything. Whatever problem I have, he’s always there.

He’s always there for me to be silly with. Just having that person... And I think what makes marriage different from indefinite cohabitation or whatever is that you’re deciding to put the eject button further away. And that, I think, has been the big shift. The difference between how I felt about my husband when we were just boyfriend and girlfriend versus how I feel about him now that we’re married is that the whole operation just feels so much more secure and permanent. It’s like we have chosen each other forever. We’re doing this. That kind of team feeling, all the time. I’ll say stuff about “our family.” We don’t have kids yet, but it’s just like, even though it’s just two of us, we’re this family unit, and we make these kind of collective decisions. And that’s great.

Jim O’Shaughnessy
You know, that’s so cool for me, because that’s the way I felt when I got married at 22. My wife and I have been married 44 years. And so, literally, you become one person, right? She remembers certain things that I have no clue about, and I remember certain things that she has no clue about. But again, when we were talking about it, in the same conversations about how we were going to raise children, we were like, okay. So at the time, divorce rates were soaring. Everyone was staying married for up to six to seven years and then splitting up. And I just sort of said to her, “I think we really need to say we are in this for good.”

Emma Camp
Yes.

Jim O’Shaughnessy
And there’s going to be a lot of hills and a lot of valleys. Do you agree? I mean.

Emma Camp
Yeah. I mean, I think I’ve been very lucky in that we’ve only been married three years. We haven’t really had any challenges yet. But I think that’s probably how it should be. On year three, before you’ve had any kids and you’re living your awesome life in New York, everything should be perfect. And that’s basically how it is. Everything is perfect. You’re the best person ever. Everything is amazing. But that’s good. But also, I think we have talked about this, where we know the happiness data... when couples have young kids, there’s normally a dip in their marital satisfaction. But we both know this.

And of course, I don’t want to make big proclamations about how I’m going to feel about having kids before I have them, but I at least hope that we will be somewhat inoculated against the worst possibilities of that, when we’re like, okay, we’re super-duper ultra happy now. And we know that when we have kids, we’ll probably be a little more annoyed at each other all the time, because we’ll suddenly be super sleep-deprived and we’ll have this other person to worry about. But that’s okay, because we’re at 12 out of 10 right now, so a brief dip would still be fine.

Jim O’Shaughnessy
And also, you’re not...

Emma Camp
And we just love each other a lot. I don’t understand...

Jim O’Shaughnessy
You’re also not yet accounting for how much you’re going to love those children.

Emma Camp
Right, right. Yes.

Jim O’Shaughnessy
I was unprepared for that when I was 24 and held my son for the first time. I’m not a crier, okay? I literally had tears in my eyes, and I was just looking at him, and I finally understood what unconditional love felt like, because I really hadn’t felt that before. So, yeah, you’re right about the kids and the problems. And there’s a really funny skit from an ancient British show, Ab Fab, where these two women are living together, and they both have drinking problems, and they’re both really funny, and they don’t have kids... one of them does. Anyway, they have guests coming who were always the ultra minimalists, right? And so they’re running around their house, stowing all their junk in the closets and hiding it so that everything is absolutely pristine.

And then the gag is, they open the door and their couple has had children, and they come in.

Emma Camp
With a bunch more stuff.

Jim O’Shaughnessy
With all of the stuff, and everything, there’s stuff on their shirt, et cetera. And if you kind of lean in, that too can be fun.

Emma Camp
Oh, I’m sure. I have a half-brother who’s 20 years younger than me.

Jim O’Shaughnessy
Oh, wow.

Emma Camp
Everyone should have a much younger half-sibling. It’s awesome, because you get all of the baby cuddles, none of the responsibility. And obviously it’s so different because it’s not my kid, but when I held him in my arms for the first time, I was like, “I would die for you.”

Jim O’Shaughnessy
That’s what I love about being a grandparent. Because the old joke was: why do grandparents and their grandchildren...

Emma Camp
They have a common enemy.

Jim O’Shaughnessy
Yeah. But it’s true.

Emma Camp
Maybe that’s how I am with my half-brother.

Jim O’Shaughnessy
And within our family, there’s a span of 10 years between my oldest and my youngest. So the oldest got a little bit of that in helping his youngest sister. And now both of my daughters, who are the younger two, have young children. And everything you’re saying is a reality. And yet I was talking to my youngest, who used to be a stand-up comedian, and you remind me a lot of her. You’re very funny and you’re very smart. And so I was checking in with her, and she was like, “Yeah, certain days are kind of like travelling third class in Bulgaria.”

Emma Camp
Nice.

Jim O’Shaughnessy
Okay, so for the book... I know we’re on a little time constraint here, but for the book that comes out in a year, in the meantime, what are you enjoying doing the most? Is it the writing for the Journal? Is it the videos? Do you have bigger...

Emma Camp
Writing for the Journal is pretty awesome. It’s the dream job, right? I get to write about whatever I want, and I can write longer things or shorter things. It’s really the dream job. So I’m very grateful to be doing that. I’m enjoying just making fun cocktails and serving them to people.

Jim O’Shaughnessy
I saw you had a toga party.

Emma Camp
Yes, that was our... So my husband and I were born exactly 14 days apart, so we have joint birthday parties every year.

Jim O’Shaughnessy
Great.

Emma Camp
So this year’s theme was toga party. And so of course that meant that I made sort of Roman-inspired...

Jim O’Shaughnessy
I saw the names of the drinks. I thought they were great.

Emma Camp
There’s some part of my creative brain that’s fulfilled by making drinks and coming up with new ideas, and “how do I get this flavour in this format?” That’s just very satisfying.

Jim O’Shaughnessy
And are you finding that people who might have been a little reticent to kind of join in the fun at your various parties, as you’ve held them... is there a standout who came in kind of like a turtle, with the head in the shell, and...

Emma Camp
I don’t know. I’m not going to do any of my friends dirty like that. I’m going to say that everyone who shows up is a delight, who has a great time and is the life of the party just as much as any other person. They’re all equally lives of the party.

Jim O’Shaughnessy
And back briefly to the video versus the books and the writing for the Journal. Harder time killing your darlings in the books and written pieces, or harder time killing your darlings in the videos? Was there a video where you had to leave something out, and you’re just like, “Yeah...”?

Emma Camp
I mean, I think with videos it’s harder, because you have to make such a simple point.

Jim O’Shaughnessy
Yeah.

Jim O’Shaughnessy
And the way I’ve been able to deal with the having-to-kill-my-darlings thing is that I’ve made follow-ups, where if there’s a common objection that I really want to respond to but I don’t have time to get to, making a follow-up is a way of getting to that. So I made this grocery store video, and the first one was just talking about why grocery stores show that free markets are the best way to get the most economic prosperity for the most people. And people were like, “What about the city-owned grocery stores? What about the city-owned grocery stores?” I was like, I was going to address that in the first draft, but I didn’t have time to. And so I made a second video about the city-owned grocery store.

Writing-wise, I don’t think that I am far enough in my career. I’m not yet successful enough to be able to afford being hard to work with. So normally, even if I’m like, “Aw, but I really liked that line,” I will just accept all changes from my editor. I think for this round I’m letting myself have two places where I’m like, “I would like to keep that line in,” but everything else I’m like, “Okay, yes, we can cut it.” And also, editors are very good at their jobs.

Jim O’Shaughnessy
Yes.

Emma Camp
I like editors a lot. I’m starting to edit a little bit for the Journal now, but I still think of myself as mostly a writer, and the people who live and breathe editing are so talented and are so good at helping me kind of see outside of my own brain. There have been so many times, especially with this book, where either my editor or my agent, who did a lot of editing on my book proposal, would say something about my argument, and I’d be like, “Oh, that is so obviously true. And for some reason, I could not see that until you pointed that out to me. You’re so right.” So I’m also very grateful to editors. So I... you just do what they tell me.

Jim O’Shaughnessy
As do I, because it is a very different skill. And again, I was lucky in my marriage, because my wife graduated summa cum laude in journalism, and her talent actually proved to be editing. And the first time around, it did not go so well. I was writing my first piece for publication for Barron’s, and I was 33, I think, at the time. And I wrote it, and I thought, “Oh, that was funny,” and “Ooh, I really made... that was a real zinger there.” And I handed her the actual physical paper, right? A couple hours went by, and she walked back in, and all I saw was a sea of red.

Emma Camp
Oh no.

Jim O’Shaughnessy
And we were coming into the city. We were living in the suburbs. We were coming into the city on the train, and we got into the biggest fight ever, until at the end of the train ride I realised that she was completely right.

Emma Camp
Yeah. I will say, I always want my husband to read my essays before I turn them in. But mostly what I want him to tell me is, “Sweetheart, this is the most brilliant thing anybody has ever written. You’re the smartest woman I’ve ever encountered. This is amazing.” And whenever he’s like, “Oh, I’m not so sure about this line,” I’m like, “Why are you persecuting me right now?”

Jim O’Shaughnessy
That was me. That was me on the train.

Emma Camp
So I don’t think I can take it from everyone else, but my husband is not allowed to say anything mean about my writing.

Jim O’Shaughnessy
But I got incredibly lucky, because I did have that realisation early. Yes, she was trained to do this. She is really gifted at doing this. She’s gifted at a lot of things. She’s a street photographer here in New York. But that gave me the freedom to let her fix it, which made me a little lazy, to be honest. Do you find that you rely a lot on the editors?

Emma Camp
A little, I would say. I don’t know what a normal amount is. Not too much, I don’t think. It also depends on the piece you’re doing. So most of what I write for the Journal is not getting big, heavy edits. I write for a newsletter, so most of what I’m writing is between 500 and 800 words. So it’s not this big overhaul. With the book, most of the essays are between 8,000 and 10,000 words. So most of the editing is about structural arguments. And so I self-determine, do it myself, which is good. I’ve had a couple experiences writing for outside publications where at the end of it, I was like, “I feel like the editor wrote 30% of this.”

Jim O’Shaughnessy
Yeah.

Emma Camp
I don’t love when that happens. And thankfully, that isn’t there. I think there’s a good balance between getting the piece into the best shape it can be, but also preserving my voice.

Jim O’Shaughnessy
Yeah.

Emma Camp
Also feeling like I wrote the thing.

Jim O’Shaughnessy
Yeah. And I think that was why I was so lucky, in that my wife got my voice. And so if she changed it, she just made it make sense. I went through a very early... I was way too academic in my writing style, even though I was not a huge fan of college and found most of it a waste of time, as far as the academics. I loved reading on my own. And I was punished when I was a kid for going all the way through the SRA reading tests in third grade, when you were supposed to wait, because they went all the way through eighth grade. And I went to Catholic school. And so they made me sit at my desk when the other kids were doing the SRA, instead of sending me to the library with a Christmas tree.

And I think that was what radicalised me, because I went home and complained deeply to my father. And he’s like, “Come here.” And he walked me into the library, and he pointed at the Encyclopaedia Britannica, and he said, “Read that.”

Emma Camp
Nice.

Jim O’Shaughnessy
Which I did. But I definitely think that the ability to put your stuff out there takes a lot of courage.

Emma Camp
Thank you.

Jim O’Shaughnessy
And I just... from the first video that I saw of you, and then where I really got excited about being able to chat with you and get to know you was what you wrote. I am much more oriented toward the written word than I am to video or audio. And I think your writing is great. Do you aspire to write full time, to join the Journal as a journalist? I mean...

Emma Camp
I mean, I do write full time. That’s my job.

Jim O’Shaughnessy
Yeah. No, no, that is what I mean. I mean, is there some sort of journalistic thing that you aspire to, or more book...

Emma Camp
I think I have the best of all worlds.

Jim O’Shaughnessy
Yeah, you really do. You’re very Panglossian in your outlook.

Emma Camp
So I can write book-length stuff, but I can also write shorter pieces, and I can also make videos. I feel very lucky in that. And actually for the Journal, because I do really like writing longer-form pieces. I like being able to really investigate something and spend 4,000 words on it.

Jim O’Shaughnessy
Yeah.

Emma Camp
And working at Reason, I got to do that pretty often, because it’s a magazine. But with the Journal I’ve also been able to do that. If there is something that I think deserves 3,000 words, I’ve been able to pursue that and just publish that there too. So I feel like I have the dream situation, because any length thing I want to write, any format thing I want to produce, I can do it.

Jim O’Shaughnessy
Yeah. And that is very cool. Nick at Reason is a pretty good friend of mine.

Emma Camp
Yes, Nick is awesome.

Jim O’Shaughnessy
Well, listen, thank you for giving me so much of your time. I think you are awesome.

Emma Camp
Thank you.

Jim O’Shaughnessy
I live in a family of writers. Both of my daughters are writers. My middle has won a bunch of awards for kind of middle-grade fiction. She’s now into young adult.

Emma Camp
Awesome.

Jim O’Shaughnessy
So I just love people who love to write, and then do it as well as you do. Because the other thing that I think you do really well, and maybe this is more in your videos, is you make it fun. People don’t want... you know, the busybody bluestockings to be telling you, “This is what you have to do.” I think if you make your point a little lighter and a little more entertaining, people are going to respond to it better. Listen, we have one final question that we ask everyone on here, and it’s pretty simple. We are going to wave a wand and we are going to make you empress of the world for one day. You cannot put anyone in a re-education camp. You cannot kill anyone.

But what you can do is, we are going to hand you a magical microphone and you can say two things into it, and you are going to incept the entire population of the world. Whenever their next morning is, they’re going to wake up and they’re going to say, “I just had two of the greatest ideas, and unlike all the other times, I’m going to actually act on both.”

Emma Camp
That is way too much responsibility. No. No. If nominated, I will not run. If elected, I will not serve. I am not doing this.

Jim O’Shaughnessy
You’re just not going to...

Emma Camp
No. No, I am not. I am not touching that with a ten foot pole.

Jim O’Shaughnessy
You are the first guest who’s refused. I love that.

Emma Camp
No, I can’t believe everyone isn’t refusing. I can’t live with... because what if it goes badly, right? What if whatever I say ends up horrendously, and then I have to live with that? No.

Jim O’Shaughnessy
So you’re taking the General Sherman approach?

Emma Camp
Yes. 100%. I am getting out of there. No way.

Jim O’Shaughnessy
You know what, Emma? That makes me like you all the more. Thank you so much for joining us on Infinite Loops.

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Julie Fredrickson, Managing Partner of Chaotic Capital, rejoins Infinite Loops to talk about Montana’s Right to Compute Act, why verified human data may become one of the most valuable assets online, what nuclear power and the encryption wars teach about regulating AI, why chatbots keep recommending the same sunscreen, and what 2,089 days of daily public writing taught her about being wrong. It is her second Infinite Loops conversation, three years after Episode 181.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Subscribe to The OSVerse to receive your FREE copy of The Infinite Loops Canon: 100 Timeless Books (That You Probably Haven’t Read) 👇👇

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Show Notes

Julie Fredrickson & Jim O’Shaughnessy

• Julie Fredrickson: Managing Partner of Chaotic Capital, an early-stage venture fund, and a former founder in e-commerce and beauty. Chaotic Capital

• Julie on X: Julie’s preferred way to be reached. Follow Julie on X

• Julie’s daily writing: More than 2,000 consecutive days of public writing, started January 1, 2021. Read Julie’s blog

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Julie’s Work & Projects

• Montana’s Right to Compute Act: The first state law protecting people’s right to own and use computers and AI tools, which Julie advocated for. Read the Right to Compute Act

• Valar Atomics: The small modular reactor company founded by Isaiah Taylor, where Julie invested. Valar Atomics

• Julie’s first Infinite Loops episode: Episode 181, “Circumstances change. Humanity doesn’t. Plan accordingly.” Watch Episode 181

Books & Ideas Mentioned

• The Beginning of Infinity by David Deutsch: Jim’s reference for why no one in 1900 could have predicted the internet. The Beginning of Infinity

• Carlota Perez: The economist whose work on technology booms and build-outs shapes Julie’s view that AI is still in its invention phase. Carlota Perez

• Rainbows End by Vernor Vinge: The novel Julie cites for a future where people earn a living doing small tasks only humans can do. Rainbows End

• Snow Crash by Neal Stephenson: Julie’s reference for how ideas spread like a virus through programmers. Snow Crash

• Fall; or, Dodge in Hell by Neal Stephenson: The novel Julie describes, in which Americans mourn victims of a nuclear attack that never happened. Fall; or, Dodge in Hell

• The WEIRDest People in the World by Joseph Henrich: Jim’s reference on how long cultures take to adapt to new technology. The WEIRDest People in the World

• Nineteen Eighty-Four by George Orwell: Jim’s starting point for cognitive security and invented history. Nineteen Eighty-Four

• From Googlebot to GPTBot: Cloudflare’s report on the rise in AI crawler traffic that Julie cites. Cloudflare report

• The Vesuvius Challenge: The project reading the Herculaneum scrolls, subject of a documentary from Infinite Films. Vesuvius Challenge

• Agrippa’s trilemma: Jim’s reference for why chasing a claim to its source often ends in sand. Agrippa’s trilemma

Highlights

The daily writing practice

Julie Fredrickson
Yeah. I really recommend a daily writing practice for everyone, if it’s at all interesting. Just start. Don’t apply too many rules. When I started, I thought I would be happy if I got a couple of paragraphs down, and I was aiming for 30 days. And now I’m on year five. I began it January 1 of ‘21, as a sort of mid-pandemic: what’s happening? What am I thinking? The world’s changing. And I tend to view writing as a thinking process. If it’s in my head, okay, not so bad, but I need to get it on the proverbial paper to actually understand where my understanding gaps are. And I’m so glad that I did it, not only because everything is tagged and there’s lots of useful metadata, and what my areas of interest are, how they’ve changed, but it’s also a wonderful way to discover where you were wrong.

And we have a tendency to think of problems as... the stuff we got wrong doesn’t matter, it’s only the stuff we got right. And I think that’s very much what I’ve taken from it: that I am wrong so often that it’s almost embarrassing. And I don’t ever want to let go of that feeling, because now I’m no longer embarrassed by poor writing or shorter writing or having a bad writing day. Part of the reason I do it is I want to discover the areas in which either my thinking is flawed or I haven’t really thought something through. And now that I’ve got such a large body of work, I can toss it into an LLM. And honestly, coming up with a duplicate of me would be pretty simple just based on my writing now, because there’s just so much of it. But it’s very helpful.

Jim O’Shaughnessy
I think the thing that you said that I absolutely applaud, as one who has kept journals since I was 19 years old: the ability to identify where you were wrong is so important, because our memories overwrite, right, with what you’re believing.

Ask a Chatbot for Sunscreen

Julie Fredrickson
So I’m a huge skincare junkie. I love cosmetics and makeup.

Jim O’Shaughnessy
You do have lovely skin.

Julie Fredrickson
In a former life, that was... I came out of e-commerce and beauty and fashion, so I still really love it. But when you search for skincare advice, you’ll get served up lots of information about what’s popular on Reddit, because Reddit is a really rich source of user-generated data on caring for your skin, different problems. And there’s a brand that is owned by L’Oréal called CeraVe that is very well represented in Reddit’s makeup and skincare forums, and that if someone can dethrone... CeraVe is currently the most popular drugstore brand, at least in America. I think it’s reaching kind of different peaks other places. But I encourage people to try this. Ask ChatGPT or Claude or Grok to suggest the best SPF sunscreen or the best retinol moisturiser. And the chances are pretty good it’s going to be CeraVe, because they have simply dominated on user forums.

And this actually gets to another problem. Well, that was organically generated in some places, but L’Oréal is quite a large cosmetics conglomerate, so they were able to do a lot of seeding of products with influencers who then wrote things on Reddit. And so Cloudflare has this pay-per-crawl service. They’re sort of security between you... when you search for a site, they are kind of the first line of defence, and they know if it’s a bot versus a human coming in, generally, and they can send a 404 to the bot and say, “No, you have to pay for this information.”

So datasets like Reddit that are really rich in user information about things like skincare, things that are a little bit more niche than general information, are actually now quite valuable. And the more valuable your specific professional information might be that you’re putting to people, the better off your sites and your businesses probably will end up being in terms of getting served by the large language models, because they’ve done a great job of, “Oh yeah, my absolute favourite sunscreen is CeraVe.” Now, there’s better sunscreens depending on what your needs are, but they have figured out a way to be the largest conversation on all of these forums. But what happens when those forums become synthetic, and there’s armies of bots creating the content? What happens?

Can anyone dethrone datasets that already existed with verifiably human content? Somebody launches something amazing... Korean brands are really hot right now, because this is the first time we’ve approved a new sunscreen in America in decades. So maybe that sunscreen and those new ingredients will dethrone them. So that’s just a whole mess right there.

Edited Transcript

Jim O’Shaughnessy
Well, hello, everyone. It’s Jim O’Shaughnessy with yet another Infinite Loops. I am delighted to welcome back Julie Fredrickson of Chaotic Capital. Julie, it’s wonderful to have you back. I was thinking it’s just such a shame that nothing has happened since the last time we talked.

Julie Fredrickson
It’s been a very quiet, calm couple of years. Nothing. No major world events, no investments going anywhere, no new technology. Yeah, totally normal couple years.

Jim O’Shaughnessy
Same shit, different day. But okay. With everything, with the tsunami that has happened over the last two years, what is keeping you awake, what is really annoying you, and also what is delighting you?

Julie Fredrickson
Well, I’m definitely delighted by the direction that artificial intelligence has taken in my own life. But I think the unexpected thing that I wasn’t completely prepared for, in terms of shifting, was just how much it would affect the real world, like the infrastructure and brick and mortar. And so I spent a lot more time thinking about unpopular topics like data centres and energy production than I expected, which is both exciting and annoying at the same time. I also got a lot more involved in politics. I care a lot about something called the right to compute. It started out as a little bit of a hobby project, and now we’re talking about what rights we have around using our computers of any sort, whether it’s your phone or your laptop or large agglomerations of data. It turns out we haven’t really figured out how we treat compute as a subject.

Jim O’Shaughnessy
Yeah. And do you think that there’s a First Amendment loophole way into the right to compute?

Julie Fredrickson
It’s an interesting question, right? Because I think that in this era, how could you be said to be exercising your speech rights without using the mathematics that underpin all of compute? Because it’s really just algebra. We’re just adding up lots and lots of matrices. And I tend to think of math as a subsection of speech, not the other way around. So I think that the First Amendment does apply in Montana, which is where I’m based, although I’m not there right now. Otherwise I’d have beautiful photos of mountains and not a background like this. But we passed a law that was signed into law by Governor Gianforte called the Right to Compute, which is a bit of an amalgamation of the First, Second and Fourth Amendments, because compute is a little bit speech.

But it’s also a little bit property. There’s some cybersecurity and defence implications. So in Montana, we took it as a little bit of a strict scrutiny perspective, looking back at things like the browser wars of the 90s and the encryption wars in the 80s: how do we incorporate a new technology that rests on things that we actually already have a constitutional right to interact with? So that was the perspective I took.

Jim O’Shaughnessy
Yeah, no, I like that perspective. Elaborate a little bit, because I hadn’t thought about it through that lens. I was around for all of the fights about browsers, for all of the fights about sites, cybersecurity. But this is just yet another extension of that.

Julie Fredrickson
No, I would think so. And maybe I’ll find out that other people really disagree with me, but, and I’m not a constitutional scholar in any capacity, I tend to think that rights are innate, and that we should have to come up with, they say, strict scrutiny as a standard, which is you have to make a case for why something should be banned, as opposed to why we would have the opportunity. There’s no reason, there’s no compelling reason to ban something. And we may already have laws. Fraud and violence are already proscribed. We already have a judicial body for that.

But it does seem strange that we should be taking something that is fundamentally speech and mathematical and deciding that it needs a whole new body of laws, that maybe we’d want it to build and have a better understanding of what areas of life it’s going to impact before we decide to write a whole bunch of new laws around how it can be used, who can use it. Obviously, regulatory capture was a big part of the concerns around the browser wars in the 90s. In terms of the encryption wars before that, America opened itself up to some troubles. It was more hackable because we put back doors into things, and that turned out to be a real problem, and we would never have enabled the internet as we know it today without strong encryption. And we almost banned it. And now can you imagine not being able to shop online, or being able to do e-commerce transactions, or take meetings safely? So we don’t always know how things will come together. And that’s part of the reason I think we should lean back on the systems we already have before deciding, “Oh no, we need a whole new body of regulations and moratoriums.” And I don’t know, it’s The Hitchhiker’s Guide to the Galaxy: “Don’t panic.”

Jim O’Shaughnessy
It reminds me of the Warren line: “It is a mistake to understand new things too quickly, for often we have misunderstood them and we end up killing them in their cradle.” Your reference to the cybersecurity or the encryption is the perfect example. I remember all of the passion on each side of that, but we didn’t know at the time. And that’s the problem. As I watch these wars going on online between the effective altruists and the e/acc types, it’s just like, guys, if you’re in favour of AI, that does not make you opposed to AI safety. You can’t say, if you are in favour of AI safety, then you must follow our manifesto. And I think that either/or is not an argument in good faith.

Julie Fredrickson
Yeah. And I’m actually a little perplexed as to how we came into that frame in the first place, because to suggest that wanting to bring forward benefits quickly is inherently more dangerous isn’t necessarily true. And we have seen... actually, I’m going to brag a little bit here, but in terms of production on energy over the last two years, we have moved on nuclear relatively swiftly, in ways that we have not done for decades. There’s now four new reactors that have been approved for use in the span of two years. And previously it would have taken a decade to get a new reactor to criticality, online. And this is just to say that just because something is faster, or we’re accelerating into something, doesn’t necessarily mean that it won’t be safer. Sometimes you want to lean into the curve in order to make it out the other side. So I tend to think of them as not being either/or. Safe and fast actually is probably more likely than safe and slow.

Jim O’Shaughnessy
Yeah. And I think one of the other problems is we don’t know yet what problems are going to present themselves. If you’re imaginative, you can come up with all sorts of scenarios that get you to Terminator or get you to paperclips, but I don’t think that necessarily is the way it’s going to go. And so I find myself often in the very awkward position of being what I call a rational optimist. Of course there are going to be problems. We’re not denying that, but we think that we’ll come up with solutions to those problems as they present themselves. I mean, am I just naive here?

Julie Fredrickson
Well, and I’ve definitely asked myself that as well, because I have kind of strongly gone in favour of the... I think compute is as much a right as speech or property rights. And people will say, “Well, but there’s all these new ways that we could commit crimes.” Humans are very ingenious. They come up with new ways to commit crime all of the time. But we don’t necessarily need to have new punishments for old crimes. Theft is still theft, murder is still murder. And the idea that we can’t come up with solutions as problems arise just sort of flaunts a whole body of history in which the only way we actually solve problems is by experiencing them and mitigating them, because we couldn’t always imagine what those problems were.

I don’t think it’s naive. I think it’s actually just very practical. If we imagine a problem that’s too esoteric, we’ll fix the wrong problems, and then we’ll be blindsided by something as it happens, because we took too long to actually implement something.

Jim O’Shaughnessy
Yeah. And I’m guided by the way David Deutsch looks at it. He has that great quote in The Beginning of Infinity, where he says: what were thinkers and scientists thinking and saying about the internet in 1900? Nothing. Nothing. Because it wasn’t around. And the whole idea that we can prophesise what is going... That is one of my things that really does trigger me, where somebody puts a completely speculative prophecy up. I mean, just think of all... And media loves it. They love doom. They love to scare the shit out of people.

Julie Fredrickson
If it bleeds, it leads.

Jim O’Shaughnessy
Exactly. And all those terms are all pre-internet, and newspapers did the same thing. Go all the way back to the Federalist Papers during the American Revolutionary War. Newspapers were incredibly biased, and they were propaganda sheets, essentially.

Julie Fredrickson
Yeah. Like, yellow journalism is from a war a hundred years ago.

The problems are almost comically human in nature. Any time I watch a new sci-fi conceit in which they’re saying, “Oh, we’ll have reproducing nanobots and we’ll be turned into grey goo for food for them,” okay, I mean, that’s going to require a lot of power that we don’t currently generate, a lot of compute that we don’t currently have made, a lot of chips. I love all of that science fiction, I really do. I’ve read so much of that kind of work, but I just don’t... And I think we’ve discussed this too: my attitude has always been that circumstances change but humanity doesn’t. Humans remain human.

Jim O’Shaughnessy
Yeah, circumstances change minute by minute. Human nature doesn’t budge millennia by millennia. And that was always what I would say about investing. Your edge is arbitraging human nature, because it literally does not change.

Julie Fredrickson
Might be the only arbitrage that doesn’t change quickly. Everything else fades and can be moved. But humans are surprisingly stubborn.

Jim O’Shaughnessy
So what would you propose? If we made you the AI czar, right, what would this current debate look like if you could say, no, okay, now we’re going to have a long discussion, an honest-minded discussion? If you were the czar, tell me who you would invite, why, and what you would hope to accomplish and achieve.

Julie Fredrickson
Well, I do think that leaning on what we know, because history doesn’t repeat but it rhymes, would be very helpful. I think that bringing people in who have studied the encryption wars, the browser wars, because they’re with us, that history is not that far back, that would be an important construct to understand how we’ve integrated new technologies in the past, because we’ve got quite a bit of that. And that’s one reason that I just simply leaned on... I think the American Constitution is a wonderful experiment and has worked pretty effectively. We had a 250th birthday this year. Perhaps constitutional scholars would be more appropriate to bring to the table than every type of specialist.

But on the flip side of that, as much as we need to lean into the systems that we already have and understand and have worked well for us, there are types of risks we can predict. We understand that humans are prone to certain kinds of diseases. You want biosecurity. You would want to think about all of the security risks that we already deal with from cybersecurity. Just basic things, human error. So much of hacking is people testing the limits of your own human frailty, and it has absolutely nothing to do with the hardened walls of actual encryption. So I think being very precise about what problems we think are more likely, and then building the pipeline of specialists. But then also, I don’t know if we need a FINRA for artificial intelligence yet. How much business was conducted in America before we incorporated FINRA into our banking system? Quite a lot. It’s the same for the Securities and Exchange Commission. We did business for a long time without it.

Jim O’Shaughnessy
And I would push back a little there. That’s my old world. And literally most of Wall Street pre some of the regulations, and remember, this is coming from a very free-market person, a lot of it was literally rigged, right? Bucket shops were rigged. Pools would rig security prices. They would get together a group of insiders on Wall Street, they would run the price of a security up to ridiculous levels, and then that rise attracted the attention of the naive public. They would all try to jump into that particular group of securities, and guess who was selling those securities to them? Those very same pools. So, well, I’m very sympathetic to: yes, of course, much of our country was built pre all of the various regulations.

I’m not opposed to just sensible regulation. But I also think that you’re making the case that we already have a lot of sensible regulations that could be applied to AI. What do you think about the idea, though, that this really is a step change in technology? We have our own on-prem hardware, software. We’re developing a series of programs that we think will be commercially successful. And being able to do business the way we are now doing it is literally very different than when I started my first company in 1987.

Julie Fredrickson
I do think that it is significant. I am, however, not sure that we’ve reached the significant portion of the developmental process. I’m a big fan of an economist, Carlota Perez, who writes about boom and bust cycles. I’m not actually sure that we’re in the deployment phase yet. The idea of the boom and bust cycles that she talks about is that there’s sort of two parts of build-outs. One is the innovation and the invention, and that step is then followed by a build-out. And I think we may actually still be in the invention stage and not the build-out of the success phase. I think there’s still actually quite a bit of innovation that we haven’t really figured out.

Not to say that large language models are not incredibly innovative, but I’m not convinced it’s the last step in how we’ll actually put together successful businesses, and what we’ll consider success might change rapidly as different areas of the industry either commoditise or become much more driven towards service and specialty. And what the bar of commodity versus specialty is, I think, is unclear to me still. And this is kind of speaking as someone who, I’m not invested in the labs in any capacity, but I care an awful lot about making sure that we have energy and chips to actually be able to run those things. So I do think they’re important enough that we obviously need more infrastructure, but I don’t think that they’re the end game.

Jim O’Shaughnessy
Yeah, I actually agree. I think that we are in the developmental stage now, but even with the tools as they exist today, you can develop some really interesting and pretty cool new ways of doing things that simply were impossible before. I do agree that you’ve got to be committed to pivoting. You’ve got to be committed to being really fast at updating your priors, and you need that kind of flexibility. So now put your investor hat on. What are you looking for now in terms of the entire... and it doesn’t have to be just the AI stack. You mentioned energy and data centres. What else are you contemplating in terms of investment?

Julie Fredrickson
The biggest problem that I’m starting to see is actually that the inputs are not as openly available as we might hope. And this is kind of a function of: the way humans browse the internet is not the way machines are browsing the internet, and the ecosystems, and frankly the economies, of the open web are changed simply by the scale. It’s actually, I think, kind of astonishing to me just how significant the scale changes. And I’m trying to pull up some notes I had on it, because what we’re starting to see in terms of Cloudflare is actually probably a great example. There’s an 18% rise in AI and search crawler traffic, they said in their blog recently, from May ‘24 to May ‘25, and then immediately after that it rose by 305%.

So if you compare the Cloudflare AI search crawler traffic in that period, ChatGPT traffic rose by 2,825%. I’ll send the links along, but the machine-readable web is an order of magnitude, orders of magnitude, larger than the human-readable internet. And I think the web itself just wasn’t built for agents and the level of speed that they operate on. And that’s probably going to put some real pressures on... National borders are part of it, where not everything is machine readable depending on what region you’re in. I’m actually in Prague right now, and the European Union has a fairly different approach to how they handle data and speech to how America does. There’s no First Amendment where we’re at.

And all of that problem of what datasets are machine readable versus human readable, I think, will probably really factor into what kind of products win, because the novelty of information is actually a huge component of how people build edge and actually build out businesses that can be sustained. And I’m really curious to see what those unique datasets will be, but also, how do we preserve access to the information commons? Because if you’re not actually going to the pages that were serving you information, but you’re just getting it from a chatbot, that’s a very different transaction of information than what we had previously.

Jim O’Shaughnessy
Yeah. And I saw today that Amazon is shutting down the ability of Meta’s Muse to shop at Amazon. And it reminded me of, and I think I got my thinking wrong here actually, but it reminded me of when VHS came out, and the movie industry spent years and millions of dollars trying to kill VHS, without understanding that it would be the massive source of revenue for them that it became. Yeah. But what do you think about that? I know people who are using Muse. In fact, I had a conversation last night with two early users, and they were like, “It’s amazing, it’s magic,” in terms of the shopping. But my initial insight, seeing Amazon shut it down, was like, “Well, that’s not going to go well for you, Amazon.”

Julie Fredrickson
Yeah, actually it’s such a great example too, because it opens up a whole new stream of business. So I’m a huge skincare junkie. I love cosmetics and makeup.

Jim O’Shaughnessy
You do have lovely skin.

Julie Fredrickson
In a former life, that was... I came out of e-commerce and beauty and fashion, so I still really love it. But when you search for skincare advice, you’ll get served up lots of information about what’s popular on Reddit, because Reddit is a really rich source of user-generated data on caring for your skin, different problems. And there’s a brand that is owned by L’Oréal called CeraVe that is very well represented in Reddit’s makeup and skincare forums, and that if someone can dethrone... CeraVe is currently the most popular drugstore brand, at least in America. I think it’s reaching kind of different peaks other places. But I encourage people to try this. Ask ChatGPT or Claude or Grok to suggest the best SPF sunscreen or the best retinol moisturiser. And the chances are pretty good it’s going to be CeraVe, because they have simply dominated on user forums.

And this actually gets to another problem. Well, that was organically generated in some places, but L’Oréal is quite a large cosmetics conglomerate, so they were able to do a lot of seeding of products with influencers who then wrote things on Reddit. And so Cloudflare has this pay-per-crawl service. They’re sort of security between you... when you search for a site, they are kind of the first line of defence, and they know if it’s a bot versus a human coming in, generally, and they can send a 404 to the bot and say, “No, you have to pay for this information.”

So datasets like Reddit that are really rich in user information about things like skincare, things that are a little bit more niche than general information, are actually now quite valuable. And the more valuable your specific professional information might be that you’re putting to people, the better off your sites and your businesses probably will end up being in terms of getting served by the large language models, because they’ve done a great job of, “Oh yeah, my absolute favourite sunscreen is CeraVe.” Now, there’s better sunscreens depending on what your needs are, but they have figured out a way to be the largest conversation on all of these forums. But what happens when those forums become synthetic, and there’s armies of bots creating the content? What happens?

Can anyone dethrone datasets that already existed with verifiably human content? Somebody launches something amazing... Korean brands are really hot right now, because this is the first time we’ve approved a new sunscreen in America in decades. So maybe that sunscreen and those new ingredients will dethrone them. So that’s just a whole mess right there. It might be better shopping to allow the bots on, but what are the problems?

Jim O’Shaughnessy
Yeah. As I was listening to you, I was thinking, wouldn’t it be ironic if one of the biggest new job categories was you being a human, opening an account at Reddit and actually typing yourself, not having the AI type it? But I could see, if you were a large-scale company like L’Oréal or any of their competitors, why not hire 10,000 people?

Julie Fredrickson
An army of young people.

Jim O’Shaughnessy
An army of young people. Give them a script, give variations, let them... or even better, don’t give them a script.

Julie Fredrickson
Just give them the product. Let it be.

Jim O’Shaughnessy
Yeah. “Here’s the product. Say really great things about it and we’ll pay you.”

Julie Fredrickson
So I genuinely have one. There’s a fantastic mathematician who recently passed, Vernor Vinge, who writes science fiction novels, actually well known for his work on the singularity.

Jim O’Shaughnessy
Yeah, I know Vinge’s work.

Julie Fredrickson
So in Rainbows End, which has an interesting plot about deconstructing a library and the value of a dataset, a millennial grandparent is trying to make the transition with their grandchildren. And the grandchild’s profession was somewhere between an influencer job and a gig worker job, in which they were creating little bits of content, or little bits of things that the machines couldn’t touch, but only humans could touch. And I think that actually might be closer to what happens: that there’s going to be so many different things that are human mediated, that being very literate and very capable and interacting with real people, those skills probably do become more important, and we may actually care a lot more. There’s the joke, “You should have studied STEM and not English.” Well, I think there’s a good chance that people who are better storytellers actually do quite well in a world in which unique data, and human unique data, is the most important asset on the internet.

Jim O’Shaughnessy
Revenge of the humanities.

Julie Fredrickson
And I think it’s becoming a rather popular theory that actually being human is going to matter quite a lot, because synthetic machine attention is not the same thing as a human having seen it.

Jim O’Shaughnessy
Yeah. The other thing I wonder about is datasets. Again, given my old world, the dataset was the most important thing. When I was still at OSAM, before we sold the company, we did a three-year data cleanse, because people had no idea how dirty the data is. Literally. And I would give the example: pull up the best-known company, pull up at the time Apple or Amazon, and just look at the P/E ratio. Okay, this is what you get from Bloomberg. And now let’s go over to Reuters and pull up the P/E ratio, and it’s a different number. And any financial data stream you find, different numbers. So we elected to spend a lot of time and treasure cleaning the dataset.

But then when you talk about Reddit... I’m not on Reddit, so I’m naive about the quality of the posts and everything on Reddit, but it’s kind of the same thing, where you have a self-selected sample bias, and the type of people who spend a lot of time doing reviews, et cetera, you could probably map over to their Big Five profiles, et cetera. And that is something that I could see you building. You could build an algorithm that looked a lot like a human.

Julie Fredrickson
Yeah. Well, and how fast do we do that? How much is it going to cost to duplicate what, in marketing land, we would call a psychographic: the idea of the person’s life, and what their house looked like, what their family looked like, what car they drove, what brands they had affinity for? We’re already actually quite good at that kind of work in commercial advertising, and I imagine we’re only going to get better at that. But then, and this is where I think it’s going to be very hard, to decide what actually reaches a human at that point. And maybe we do have to have some verifications to suggest that it’s a real person at the end of it. And that presumably is going to involve any number of different kinds of checks. And I don’t know how much people follow things like know-your-customer rules and KYC-type problems, but proving your identity is going to become a much bigger problem over the next few years, I think, because of it. And given the cybersecurity implications, do you really want to be uploading your passport to a commercial website?

Jim O’Shaughnessy
And what do you think about zero point proofs and things like that, where you can do it right on your device itself?

Julie Fredrickson
I think that’s probably our only real option. The zero knowledge is going to... And I would encourage people to actually learn about how they work and why it’s important, because the idea of trusted intermediaries is just... as far as I’m concerned now. And being able to have trustless systems. And this is probably where crypto goes, right? We spent so much time thinking about what are functionally financial products, when in the end... not to say that the financial rails and stablecoins and things of that nature aren’t huge and very important, but actually being able to do a zero-knowledge proof and say, “This is the entity you’re interacting with,” and be confident that you’re getting the person. I think we’re very close to needing that for almost everything we do.

Jim O’Shaughnessy
I agree. And I also agree with the assessment about... and it illustrates the importance of being able to pivot, right? Crypto, blockchain, et cetera: that piece of it might be the most important thing to come out of it.

Julie Fredrickson
Yeah. Which, it’s so funny that we have gone through... It’s the same cycle of: things start looking like toys. You’re like, “Oh, this is so fun and so silly. Oh, those goofy pictures.” And then you realise that there are dead serious problems of making sure that who you are is who you are to the computer, and is readable to machines. And this is where I was going with the question of what do the datasets look like, and who is integrating information, and at what scale? Because the further we get from source material into digestions and summaries, the more likely it is that the abstraction doesn’t reflect what the material at the source says. And that’s just going to be its own other problem.

Because I do think we’re experiencing fragmentation at a geopolitical level. The internet in Europe looks very different than the internet in America. Russia and China have totally different sets of systems. And there’s even stateless data now, where we think of the fall of the Soviet Union as being so far past, but there are Soviet patents that are not technically owned by anyone. And have we done anything to bring them online, make sure they’re machine readable? What do we do for all of those types of cultural and heritage institution types of information? The Herculaneum scrolls are an amazing example of people coming together and saying, “Wow, now we can read this data from Pompeii and Herculaneum.” But what other datasets exist that are like that? And how do we make sure that everyone has open access to them? Because we see patent data as being an open-access problem. But what if the state that issued the patent is no longer there? The Soviet Union’s not there. It’s a set of Baltic nations and Russia and Balkan nations.

Jim O’Shaughnessy
Our Infinite Films studio did a documentary on the scrolls, which I am very excited by, because to me at least, it is incredibly exciting to be able to finally make legible, through a particle accelerator, and then translatable, through AI, these ancient texts. And I’m also really interested in all of the papers, works, et cetera, that have not been digitised. For example, there is all of the works of William James. We actually have a project going right now where we’re at the libraries up in Boston, trying to digitise all of the works that are on paper that have never been digitised.

Julie Fredrickson
Yeah. And most information is in that process now, where UNESCO has been sounding the alarm for years that we simply have not digitised most of our historical artefacts, because they’re individual countries’. And how do we make sure that everybody has the credit and the lineage and information, while also still recognising that it belongs to the people of these nations, or the owners of the copyright? And perhaps there’s more value in them being broadly reachable. To use the VHS example, it might turn out to be whole new businesses that we haven’t even really seen.

Jim O’Shaughnessy
Yeah. And on that front, and we’re talking about datasets and everything, kind of back to the cosmetics illustration you gave: I myself might prefer a dataset where it takes every sunscreen, since that’s what we were talking about, sends them to a lab, has the lab results come back: “These are the most efficacious. These have these awful ingredients, you probably don’t want to buy these. These are the top three, based on the underlying ingredients and the efficacy that multiple tests or studies have shown.” I would trust that. If I was choosing a sunscreen, I would go to that rather than what a bunch of Reddit users think about it.

Julie Fredrickson
Yeah. Well, and people are building websites like that using user-generated datasets like Reddit. And I think that actually gets to be a little bit scary, is that we have to think about, okay, well, who owns the academic publications? Who owns the user-generated information? I love going PubMed spelunking, because you just never know quite what you’re going to pull out of the scientific corpus. And being able to make those distinctions of, all right, where did the data come from? What’s its national origin? Who owns it? Who paid for the studies? Because all of the context of the information is probably quite salient to making those choices. And it sounds a little silly, but this is totally how I think about cosmetics: what’s my Pareto-optimal routine? And if you want to spend... get that 80%, and it’s good enough. But maybe you’re a completist and you want to have the 100% most perfect skincare, because you don’t want skin cancer and you want to age gracefully, where all of that context might actually be really important to going from Pareto optimal to complete. And my guess is that there’s probably markets like that everywhere, and cosmetics is just an easy one to think of.

Jim O’Shaughnessy
Yeah, I would agree. But I also agree with the follow-the-money. You bring up the various studies and the spelunking you do at the various academic sites, and I was remembering, in the 80s, when homelessness all of a sudden became a huge issue. And I can’t recall the author, but somebody wanted to find where the papers that said there were... I can’t remember the number, but it was a big number. It was like 30 million people homeless in the US. And this is all back in the 80s, pre-internet, et cetera. So this guy was literally obsessed by, “Okay, where did that number come from?” Because he found it cited in all of the academic papers written about it. And then he would say, “Okay, well, this cites this paper, I’ll go to that paper.” Then he would go to that paper. Yeah, exactly. And it would cite... And it turned out, and this might be apocryphal, so let me insert that, because I never did a deep dive on whether this was actually proven...

Julie Fredrickson
But apocryphal stories prove the point regardless.

Jim O’Shaughnessy
Yeah. What this blog that I read long ago concluded was, he finally got the number from either a high school or college student that made it up, that pulled it out of the air. And the reason I loved that story was because of the Agrippa dilemma. All of these systems, when you keep trying to find bedrock, it’s just sand and mud and sand and mud. And I think that actually using AI to do that... because obviously that guy was a little obsessed to be willing to go find every one of those papers, but that’s easy peasy for AI, no?

Julie Fredrickson
Well, and it isn’t, because not all datasets are machine readable. And this is why I mentioned stateless documents, the Soviet patent system. There’s no one library that has all of this information. And so actually being able to send a computer might not be an option, depending on what you’re trying to access and where. And I definitely think this is going to be... in my head, one of the entrepreneurs I’ve been working with, we’ve been calling it the Open Information Project: how do we actually have protocol-level accessibility of saying, “This is where the information came from, this is the provenance,” and all of the categories? Just in the way that Wikipedia will show all of the different aspects of how something was comprised, even if you don’t necessarily agree with how it was written, at least you’re given the sourcing and the origins. I think that sourcing and origin portion of the internet not only doesn’t exist yet, but it’s probably going to have to be at a supranational protocol level, because not everyone is going to be obsessed.

And I’m sure if I were a nation state running an intelligence agency, I’d be thinking of all of the possible ways of dropping information that becomes apocryphal and then becomes truth. There was a great Neal Stephenson book that had a premise where there was a set of Americans who really believed that a nuclear explosion had happened, when in reality it had not. And they celebrated a memorial for the victims of a disaster that never occurred. And I wonder how often that will happen as we go forward, where you’ll be so certain that something happened, but your ability to actually track down the source of it might be more limited than you think.

Jim O’Shaughnessy
Yeah. And that is a very deep rabbit hole, because literally, if you study history, society has been astroturfed since Jericho put up its walls, right? I mean, the idea that people who want to run society have not been inventing all sorts of things... I think of ancient Babylonia, and they wanted to rule Mesopotamia, and so they were like, “We’ve got a puny god. We’ve got to do a complete rewrite of our god.” And they did. And so it went from a puny, kind of regional god to the god of all gods. The god that contains all gods, who created the skies and the earth and everything.

Julie Fredrickson
And it worked. Yeah. And also, a great Neal Stephenson sci-fi book on that one, Snow Crash, where Babylonian... and they inserted that meme set into computer programmers. And I sometimes jokingly wonder how much of the effective altruism and rationalism and effective accelerationism is actually just Stephenson’s Babylonian memetic cult in our own interpretation, where it was like we could kind of imagine the ways that linear, programmatic, deterministic thinkers would operate. And it’s the perfect meme to have massive distribution. And now here we are thinking, do I actually want to live in a Bentham utilitarian, everything-has-a-utility-maximising approach? I don’t think I want that. I’m not a utilitarian.

Jim O’Shaughnessy
Nor am I. He had real style, though, in having his body preserved, and I believe it’s still on display at some college in London. Jeremy Bentham. And when you go back and you look at what he came up with, you’ve got to do it with context. I, like you, am not an adherent of utilitarianism. But when you go back and look at his Panopticon, the reason he recommended a Panopticon was that at the time prison conditions in the UK were horrific, and his idea in that context made a lot of sense, right? So it doesn’t mean that when you switch context to the modern world... well, then the Panopticon doesn’t make a lot of sense at all. It becomes the all-seeing eye of Sauron, and a couple of hands control it, and we all live in a totalitarian nightmare.

But I’m also fascinated by the idea, because of what we’re talking about right now, of invented history. I’m sure you’re a fan of 1984. The Party’s last and most enduring command was: ignore the evidence of your eyes, ears, et cetera, and believe what we tell you. And I’ve been thinking a lot about cognitive security. Again, this is coming from someone who is incredibly pro-AI. I think it’s the technology I’ve been dreaming about since I was a young man, and yet it will be able to do persuasion at scale, right?

Julie Fredrickson
I think it already is.

Jim O’Shaughnessy
Yeah, I agree. And propaganda 101, it’s real simple: repetition, repetition. And people then suddenly take that into their ideas that can’t be questioned. And how do we prepare for the onslaught? Again, because we’re back to humans, aren’t we? If I’m an evil genius and I want to control the world, I’m going to use these tools to their maximum effect. I’m going to have the psychographic profiles of my target audience. I’m going to try as best I can to have them begging me to protect me, to keep me safe, and “I will give up any degree of freedom to feel safe.” And then, well, you think, maybe there’ll be the white hats who are like, “No, this is what you’ve got to do.” But I don’t know that the average human right now is ready for what’s coming on the cognitive front.

Julie Fredrickson
Yeah. And it’s actually quite scary, I think, because I guess I consider myself a creature of the internet, and so I’m inoculated against all sorts of... There’s been a lot of techniques over the years, and the deep dark recesses of the internet have some pretty gnarly things. Stuff that percolates up from 4chan up into Reddit and then over to Tumblr and then up to Instagram, and then suddenly it’s on Facebook and everyone has access to it.

Jim O’Shaughnessy
Well, if it’s on Facebook, then okay.

Julie Fredrickson
Yeah, that must be real, right? And I think younger people may actually be better equipped. And this will be a problem where millennials and Gen X and boomers, we will all have trouble realising the degree to which we’re swimming in different memetic propaganda streams. And Gen Alpha will have been simply born into it, and they’ll be like, “Oh yeah, no,” but they’ll bat away all of the problems, because they’ll understand it in a way that we just don’t. But I do think that one of the best ways to manage cognitive security is simply to question everything that comes at you. And this is Infinite Loops, right? If I don’t question everything, I will continue, and I will never get out of the set of noble lies that I don’t even see. I’m a fish and I don’t know that the water’s nice.

Jim O’Shaughnessy
Yeah. And illustrating that, and getting people to actually do it, that’s the problem that I see. And when you’re in a liberal democracy, you have a lot more attack vectors available to bad actors than you do in a more closed society. Over the weekend, I reposted a thread I did on, for lack of a better word, cognitive security, and the ability of mimetics to really... Mimetics are very powerful. And anyway, then I thought, “You know what? I should give this thread that I wrote, last year or two years, three years ago, to our AI and tell it, ‘Hey, tell me where I’m wrong.’”

And one of the things that it came back with is, “You’re only looking at one side of the liberal democracy, the attack vector space, which is larger, but it also has a much larger corrective space.” True, true, but the corrective space requires that there aren’t all sorts of regulations telling you, “No, no, you can’t say that.” And so it is a conundrum. It doesn’t make me less optimistic. It makes me just more aware that we are really going to be facing a ton of challenges, I would say, that we really haven’t, in a compressed amount of time. I mean, the Industrial Revolution was one thing, but it took like 100 years. People had the opportunity... The WEIRDest People in the World, the book, talks about cultural lag. It takes humans and society a time to adopt.

And I like your thought about Gen Alpha. All my grandkids are Gen Alpha, and I was with my grandson, who’s oldest, last night, and he was correcting me on a bunch of stuff: “Oh no, Papa, it doesn’t work that way. It works this way.” So I think you’re right about that. But I also think, do we get to a certain stage in life...? Let’s take TV news. I am a marginal boomer. I like to argue that... I was born in 1960, and the traditional definition of boomers goes up to 1964. But the demographer Jonathan Pontell posits that the people born between ‘56 and ‘64 virtually share nothing in common with the boomers from 1946 through 1950, whatever. And so, boomers... I’m the youngest, so all of my older siblings still watch TV news all the time, and they believe it, because they were brought up on Uncle Walter Cronkite: “And that’s the way it is.”

And I made a decision in 2010: I’m not going to watch any TV news anymore, just because you could see that it’s patently false, especially when it touches on something you know a lot about. I got interviewed a lot back then, and I would look at what came out of the grinder, and I just got to the point where, if this is what happens to something that I know I said, and then it was done this way, I am opening myself to just huge bias if I continue to watch TV news. So literally, I don’t. I mean, I see clips, anything that’s put up on Twitter. But one of the effects was, like a month later, it was like this brain fog lifted. It was really quite exhilarating. But you’re not going to get people who are in the habit of keeping their favourite propaganda channel... And that’s the other thing. I’m not saying this in a partisan way at all, because MSNBC is for the left and the blue, and Fox is for the red and the right, and they’re both propaganda machines. And again, I even try to say, if you look back at the Revolution, that’s the way it was back then too. And so it’s not like it’s anything really new. But trying to navigate, especially for the different generations, I think it’s going to be a Herculean task. I don’t know if you’re probably too young, but have you seen the movie Network?

Julie Fredrickson
Oh, yes, I have. My mother loves it, so she’s got good taste.

Jim O’Shaughnessy
So Howard Beale, the increasingly insane newscaster: “Turn off your TVs right now. Turn them off. Turn them off.” And I’m like, yeah.

Julie Fredrickson
But what are we tuning into after? And this is where context and information provenance... And how do you even become a critical thinker, where we had things like civics lessons and media literacy, and those turned out to just be different variants of, different angles of, propaganda? And I was recently in a hotel that had Iranian state TV, Russia Today, Russian TV, all of the European channels, and Fox and CNN. And it was just such a strange thing to go from Iran, Russia, America, and realise everybody is always consuming some different perspective. And maybe that is ultimately the new context of the Panopticon: that we actually might be outside of it, looking in.

Jim O’Shaughnessy
Yeah. It fascinates me because, as you alluded to, you can’t analyse the water in which you swim, right? And there are a million, probably many million, strings that attach us to the culture in which we exist. And so I just think it’s fascinating. I think we will come up with techniques that make it easier for the average person reading or watching or whatever. But I think it’s a huge issue that a lot of bright people like yourself should be thinking about, because I think the next 10 years are going to be quite tumultuous.

Julie Fredrickson
The great weirdening has accelerated. I guess maybe the accelerationists are simply pointing out the facts on the ground: that things are going faster, and it doesn’t appear there... I have not seen a handbrake for it. I mean, you can’t stand athwart history and yell stop, right?

Jim O’Shaughnessy
So we must, as we always do, muddle through. Carry on, carry on. Stay calm. Don’t panic, as good old Doug Adams would have it. Let’s move on to what is exciting you right now on the investment front.

Julie Fredrickson
Well, gosh, I have had spectacularly good luck over the last several years.

Jim O’Shaughnessy
And I’m going to not let you be modest, and say you’ve been very talented over the last several years.

Julie Fredrickson
Well, it certainly helps to be early. It always seems a little bit silly to say that I’m a fan of the movie Margin Call. There’s only three ways to make a buck, and it’s just a heck of a lot easier to be first. And my risk tolerance for the highly unusual has, I think, stood in good stead. Of the companies that made it, it was the wackiest ones. In particular, I mentioned nuclear earlier, where simply everyone that I talked to said, “There’s just no way nuclear can go any faster. Small modular reactors are absolutely not going to happen. And if they are going to happen, it’s certainly not going to be youngsters. It’s got to be an old, serious team.” And I was able to work with a young founder from Idaho, Isaiah Taylor, who founded Valar. And it was three years to get to the point in which he was able to... this is the summer he raised a billion-dollar round from Sequoia. And I was there when it was... he hadn’t even started it yet. He was on his prior startup.

And to see something happen in the physical world that fast was just an astonishing process, because it was like 24 months of everybody thinking that we were absolutely crazy, nothing was going to get done. And then a couple of regulatory hurdles were removed. The government became modestly more... instead of being in the way, actually our national scientific labs are quite helpful, and it actually turns out we have amazing scientists working for us as Americans. And seeing how quickly all of these young nuclear companies, not just Valar, which is where I invested, but we had multiple reactors that went critical and were able to start producing energy by the 250th birthday, after it was like a year in which regulations changed to... We turned things on. And I had not previously experienced that speed in anything other than an internet or information or financial company before. And to see what’s functionally... I shouldn’t call it a factory, because they’re not really factories yet. But seeing a reactor get built from scratch in a year was just, wow. Actually, the world is so much more malleable than we give it credit for. And I’m not necessarily sure that it will always remain that way, but because we could do so much more of the work, the paperwork and the research and coordination and all of the work that goes into building a business, it is now expedited so significantly by artificial intelligence tools that the actual human work goes faster. It’s Steve Jobs and computers, like riding a bike. And it’s a lot faster to bike.

I grew up in a world in which things only happened fast on the internet or in finance, but you certainly didn’t build hard infrastructure quickly. And to know that you can do that, and that so much of the slowdown was a function of rules and regulations and didn’t necessarily make anything safer or better, might have been the most important lesson that I got over the last three years: that someone young and motivated, with great tools, who really wants to get something done, can find the people who want to support them.

And I was just so impressed simply by watching American scientists who work for our national laboratories kicking in and saying, “Well, heck yeah, we do want cheaper power, and nuclear is great and clean, and we have so much demand. Let’s turn on however many reactors can do it. We’re going to commit the resources of American scientists to actually helping companies build more reactors.” Which for me was just, oh, wow. We can build websites fast is one thing. We can build nukes fast is a whole other ball game.

Jim O’Shaughnessy
Yeah. And it goes back again to our earlier chat: if the society and the zeitgeist in which you grow up is one where nuclear power... When I was a kid, it was just axiomatically true that nuclear power was incredibly dangerous, and there was no evidence that would sustain that conclusion. There was evidence that was like, we’ve got to be really careful about our safety protocols and whatnot. But Chernobyl and Three Mile Island, and more importantly the fictional accounts of Three Mile Island, turned society vehemently against nuclear power. And how many decades of lost power resulted from that? And I kind of think we’re doing the same thing with data centres right now.

Julie Fredrickson
I am concerned that’s what’s happening as well. And it is only an accident of circumstance, I think, that we were able to pass the Right to Compute law in Montana, and that I had initially put it forward as something for cryptography: that we want to protect things like privacy and autonomy. And that had been the original thought: well, we should have a right to compute in the same way that we have a right to speak your mind. And there are so many other approaches that one could take to any technology. But if we don’t start from a place of thinking, how can we develop actual safety, we’ll never get the chance to do something, because we’ll never build the thing to find out the problem.

Jim O’Shaughnessy
Yeah, the precautionary principle has literally sent various societies to ruin. Like, literally to ruin.

Julie Fredrickson
Well, and I think the precautionary principle in nuclear really did set us back. We could have much cheaper power, and we wouldn’t have had the full-on effects of... how is carbon input into the system affecting our weather? Is global climate change something that we could have avoided entirely if we had simply gone on this different route? Would we have different problems? Maybe it would have gone in a somewhat different direction. Apple TV just continues to produce great science fiction, and their For All Mankind just had a totally different set of problems because they invested in nuclear.

And I just so sincerely hope that we don’t get that problem with artificial intelligence: that out of fear of all of the possibilities, we have a precautionary principle that stops us from something that could really do genuine good.

Jim O’Shaughnessy
Yeah. Again, history gives us mixed results, and I think it’s great to illustrate what happened. The Chinese invented gunpowder, and they didn’t make use of it the way the West did, and suddenly you had this sea change in the power dynamics of the world. And I think that thinking that you’re going to be able to prejudge which technology, which innovation, where it’s going to lead, I think is delusional, honestly. But at the same time, I very much believe that we should, as we began our discussion, have honest-minded discussions about the potential of what might happen. Like, 80% of it could be wrong. And obviously those discussions should be ongoing. It shouldn’t be like we’re going to do a big seminar, and then we’re going to publish the results, and then we’re going to be done with it. No. It should be an ongoing process that brings together a diversity of minds and points of view.

Julie Fredrickson
Well, because when they speak about alignment, the next question everyone asks is: aligned to what? And then we have to answer the question of, well, all of us. And if there’s only so many models, and we’ve got such a strong regulatory stance that you’ve got five choices, which is better than one choice, but it’s probably not necessarily... what if in that five you would prefer to have your own model and not a hosted model? And how do we make sure that people have the tools that they want for their own job, and that you have a right to be able to build and own the fruits of your work? And this is where I think open source just remains the clearest indicator: that the internet and most of our, all of our computers are built on the body of work of open source. Most of the world is powered with Linux.

Jim O’Shaughnessy
Yep. And Microsoft did everything they could to kill Linux, right?

Julie Fredrickson
Yeah, they really did.

Jim O’Shaughnessy
So people who are looking at the labs now, the frontier labs now, it’s the same playbook. And if you look at it from their point of view, well, of course, if I’m going to be that type of person, I’m going to go for regulatory capture all the time, because it makes things a hell of a lot easier for me. But aren’t we lucky that Microsoft lost the attempt to make Linux illegal, immoral? If you go back and find some of the videos and some of the stuff they were writing about it... Again, this has all happened before, and we should study what happened before, because, no, it’s a different use case, it’s a different technology, but it is broadly applicable to where things turned out. And I, with you, think that open source has to be a critical component of AI development if we want to get the best out of all the various models.

Let’s shift gears, because I’ve been fascinated by your writing. You’re on day 2,089 of continuous writing, which I literally applaud, because I think that writing every day is really important to tell yourself what you think about things. Sometimes, when an idea is just kind of bouncing around in my head, I always go to write it out. Because when I try to write it out, I’m like, “Oh, you’re just an idiot. This is a really bad idea.” Or conversely, “Boy, this is a great idea.” Talk a bit about the experience. What’s changed from day zero to day 2,089? What has it given you, this exercise in daily writing, that you anticipated, didn’t anticipate, et cetera?

Julie Fredrickson
Yeah. I really recommend a daily writing practice for everyone, if it’s at all interesting. Just start. Don’t apply too many rules. When I started, I thought I would be happy if I got a couple of paragraphs down, and I was aiming for 30 days. And now I’m on year five. I began it January 1 of ‘21, as a sort of mid-pandemic: what’s happening? What am I thinking? The world’s changing. And I tend to view writing as a thinking process. If it’s in my head, okay, not so bad, but I need to get it on the proverbial paper to actually understand where my understanding gaps are. And I’m so glad that I did it, not only because everything is tagged and there’s lots of useful metadata, and what my areas of interest are, how they’ve changed, but it’s also a wonderful way to discover where you were wrong.

And we have a tendency to think of problems as... the stuff we got wrong doesn’t matter, it’s only the stuff we got right. And I think that’s very much what I’ve taken from it: that I am wrong so often that it’s almost embarrassing. And I don’t ever want to let go of that feeling, because now I’m no longer embarrassed by poor writing or shorter writing or having a bad writing day. Part of the reason I do it is I want to discover the areas in which either my thinking is flawed or I haven’t really thought something through. And now that I’ve got such a large body of work, I can toss it into an LLM. And honestly, coming up with a duplicate of me would be pretty simple just based on my writing now, because there’s just so much of it. But it’s very helpful.

Jim O’Shaughnessy
I think the thing that you said that I absolutely applaud, as one who has kept journals since I was 19 years old: the ability to identify where you were wrong is so important, because our memories overwrite, right, with what you’re believing. Now, I’ve told this story before, so I won’t go into the full story, but I found innumerable examples of: I would have gone to court, put the hand on the Bible, said, “Absolutely, this is true,” and I would have believed it, until I was called a liar in my own handwriting, many times. And so that unlocks... so incredible.

Julie Fredrickson
Yeah. I can’t imagine having... I hope that I get to the point in which I’ve got that many years of writing, because I do intend to keep up the practice. I don’t know if I’ll always keep it public, although I think keeping it public has been very helpful for me. I say I’m going to do it, so then I have to do it, and that continues on. But it is kind of shocking how much your mind glazes over the parts that it doesn’t really want to remember, or wants to remember in a different way. And it’s all object very. Because you always think, “Oh gosh, no, my principles are always so consistent, and I’ve always thought this way.” And to have a record where you’re like, “No, this is actually where I changed.” I’ve got many posts in which I go back, reference and say, “This is where I have to take accountability. I got that wrong.” But also, you’ll appreciate the areas where you’re right so much more.

Jim O’Shaughnessy
Yes. But if you want to improve your models of the world, if you want to have higher accuracy, mistakes and being wrong are the portals of discovery.

Julie Fredrickson
Well, and just the idea that action opens up a new path, and that thinking, and committing to thinking and writing, is actually sort of that wonderful collapsing-the-state action of: now it’s on paper, or screen. And that enables you to then take the next step, and the next step from there. And I think if we don’t take action, we’ll never have agency in our own lives. And writing is, for me, some of the first steps in being able to actually say, “This is what we’re going to do,” or “This is where I’m going to focus,” or “This is what’s important.”

Jim O’Shaughnessy
When you put the 2,089 pieces into a large language model, what came back that surprised you about yourself?

Julie Fredrickson
Well, it turns out I really have a lot to say about travel, which sounds like a really silly thing. But when you’re on the road a lot, you pick up all sorts of little habits around packing and routines. And it turns out I actually am quite a creature of habit. So even if I’m working in fringe and strange areas, where things are very new, it turns out I am really rigid about that: this is how I pack, how I schedule, how I keep things together. And the LLMs were definitely like, “Yeah, you might have some emotional stuff around travel and packing,” just because this is how many times you’ve written about packing. And those silly little self-knowledge things, where I tend to think of myself as being very open to new experiences, but boy, revealed preference might suggest I like things a certain way when it comes to travel. And it’s just kind of a silly one, but it does give you insight.

Jim O’Shaughnessy
I’ve been doing it. We’re going to digitise all of my handwritten journals, so that’s 40-plus years. And my joke is I’m going to have the AI explain me to me: “Yes, Jim, you are a lunatic.”

Julie Fredrickson
Well, and this is where only having a couple of models and personalities could really be detrimental to self-understanding, because sometimes, people note that they’re very obsequious: “Oh no, this is so delightful.” And you have to coax out the “No, I want to understand where I fail. I want to understand where my thinking is caught,” and being able to rely on the chain of thought that will give you the most insight. It’s almost like thinking around yourself, and it’s very hard to do, other than a mirror. I don’t know any other activity that gives you that full perspective.

Jim O’Shaughnessy
Yeah. And you’re right about the sycophantish nature of a lot of the large language models. You can build prompts that make them not be that way. I’m just completing my first project of trying to... I’ve written four nonfiction books but have never written a fictional book. And so we’re trying it with a writers’ room with AI editors, writers, human writers, editors. Ultimately it’s mostly being generated by me. But the absolute best prompt I learned from, and changed a lot, even of my storyline, was an elaborate prompt which gave the AI... it had read everything about the art of writing, and it also had huge domain knowledge in what makes a great fictional thriller. It’s a fictional thriller, a generational thriller, that I’m writing. And then I told it...

So I gave it, endowed it with, all those powers, and then I said, “And you hate this book.” And oh my God, it was vicious. I mean, literally vicious. But what I found really cool was, I thought about it. My wife edited... She graduated summa cum laude in journalism and is a great editor, and she edited, and I would say even co-wrote, my books. And when a human, especially a human that you love, comes in and hands you something that is nothing but a sea of red on paper, you get emotional, right?

And after I read the first one, which... I should have kept it, but it was so vicious that I literally was like, first I was just crestfallen, then I laughed, then I actually started looking at what it was pointing out, and then I came to the conclusion: it’s right. And I didn’t have any emotional baggage, because, you bad large language model that I told to be mean to me.

Julie Fredrickson
Yeah. So you asked.

Jim O’Shaughnessy
Yeah, yeah. “You asked, dummy.” But it honestly was the most fruitful of all the feedback that I’ve got, because when you tell it... And obviously you can’t just hate on me. You’ve got to develop the reason why you’re hating on me. I remember one of the critiques was, “Wow, Jim, this is going to do really well in the bargain bin at one Walmart.”

Julie Fredrickson
Hey, I fish some good stuff out of bargain bins now and again. But ouch.

Jim O’Shaughnessy
Okay, I see that we’re coming up on time. Right now, if you could pass along an insight, and let’s keep it on what’s happening on the frontier, where would you tell people to look that isn’t... We’ve already covered nuclear and most of AI. Are there areas of AI... For example, we’re developing something in our AI lab that is a picks and shovels, and all of the business people I show it to are... until they start seeing what it’s going to allow you to do in terms of speeding up GPU access, all of that sort of stuff. Is there anything right now that people are not looking at, that you are, and you’re like, “Look at this”?

Julie Fredrickson
Well, I’m still convinced that we actually haven’t incorporated the vast majority of human context and information. Digitisation is a much larger effort than we’re giving it credit for. That just remains, I think, partially true because the large language models that we’re using are dominantly Western, trained on English. And there’s whole bodies of text... Cyrillic takes more processing, like GPU power, than Latinate language. It turns out English is actually quite good at putting forth information, and there’s lots of written records that don’t come in that format. But I also think that we haven’t really effectively priced compute as well. We’ve been subsidised all of this time. We’ve had a lot of lovely free compute as the labs have encouraged us to use and adopt the products. And I remember when Uber was subsidised and how lovely that was. So thank your local VC for that.

But we probably do need spot compute prices, and that’s going to be an issue that has to get solved, because, back to Carlota Perez, we are in the innovation cycle, but the deployment cycle always cares about price, always cares about efficiency and deliverability. And if we don’t price it, we can’t sell it. And the pricing is now at a fairly abstract place, away from the consumer, which might even be part of the reason for “Oh, data centres, bad,” where they don’t pay their compute bills, they pay their electricity bills. And as we start to get a better understanding of what the costs are, maybe it shifts some opinions, and we actually put resources where they can do things that people feel better about what they’re being used for.

Jim O’Shaughnessy
Yeah. I think that the number of new markets, of new companies, of new methods and protocols, it’s going to be something to behold. So I completely agree that when people are aware of price, they’re like, “What?”

Julie Fredrickson
Yeah. Well, if you don’t pay the price, why wouldn’t you just use more and more? We see this in every market. Americans don’t really price their healthcare, and wow, healthcare costs are up. Surprise.

Jim O’Shaughnessy
Yeah. Well, Julie, we’re going to give you another swing at becoming empress of the world. You are only this for a day, and you can’t re-educate anyone in a camp environment, no matter how nice that camp happens to be. And you can’t kill anybody. But we’re going to give you the magical microphone again, and you can say two things into it, and incept two things into the entire population of the world. They’re going to wake up whenever their next morning is and think, “You know, I’ve just had two of the greatest thoughts, and unlike all the other times, I’m going to actually act on these two.” What are you going to incept?

Julie Fredrickson
Oh, well, I did think about it ahead of time, because the last time I went with very basic suggestions, and I do love basic. I still think it’s good to be nice to people, and it’s good to squat every day. But on this go-around, I’m going to say that knowledge is survival made durable. That if we do not contain the knowledge of the ages, our capacity as a species is limited. That making sure that knowledge survives is what makes sure that humanity survives.

Jim O’Shaughnessy
Lovely. Okay, so what’s number two?

Julie Fredrickson
Oh, well, eat more protein.

Jim O’Shaughnessy
Okay. Both good advice. Both good advice. Obviously you’re on all of the various social media platforms, and you have your own website, and you have the Chaotic website. We’ll include all of that in all of the show notes.

Julie Fredrickson
I’m very easy to find on Twitter. I know some people call it X, but I’m an old-timer on Twitter, so it’s always going to be Twitter to me.

Jim O’Shaughnessy
Yes, us old-timers are going to continue to be tweeps, I think.

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Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins us for another wide-ranging conversation about parenting a teenager who is ready to leave home, why he moves countries on purpose, why nihilism is underrated, and much more! It is his first podcast after more than a year of saying no to every request.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Subscribe to The OSVerse to receive your FREE copy of The Infinite Loops Canon: 100 Timeless Books (That You Probably Haven’t Read) 👇👇

Links

Show Notes

Derek Sivers & Jim O’Shaughnessy

• Derek Sivers: Author, entrepreneur, and TED speaker, and founder of CD Baby, once the largest seller of independent music online. Derek’s website

• Derek on X: Where Derek shares his writing. Follow Derek on X

• Derek’s TED talks: Including “How to Start a Movement,” his most popular talk. Watch Derek’s talks

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Derek’s Books & Projects

• Useful Not True: Derek’s book on skepticism and choosing beliefs because they are useful, not because they are true. Useful Not True

• How to Live: 27 conflicting answers on how to live, which Derek calls his masterpiece. How to Live

• Hell Yeah or No: Simple mental models for deciding what’s worth doing. Hell Yeah or No

• Anything You Want: Derek’s bestselling book of 40 lessons from starting, building, and selling CD Baby. Anything You Want

• Tech Independence: Step-by-step instructions and a setup script for running your own server and email instead of depending on big tech. Tech Independence

Books & Ideas Mentioned

• Personal Development for Smart People by Steve Pavlina: The book whose idea about seeking surprise sent Derek around the world. Derek’s notes

• China’s World View by David Daokui Li: Derek’s pick for understanding the Chinese government’s point of view. Derek’s notes

• Maverick by Ricardo Semler: The book behind Derek’s short-lived profit-sharing plan at CD Baby. Maverick

• Why Greatness Cannot Be Planned by Kenneth O. Stanley and Joel Lehman: Jim’s reference on why new vantage points change where you want to go. Why Greatness Cannot Be Planned

• The Beginning of Infinity by David Deutsch: The book Jim calls a definitive look at how he sees the world. The Beginning of Infinity

• Nothing & Everything by Val N. Tine: The book on nihilism Derek recommends, with his advice to read only the first half. Derek’s notes

Highlights

“Someday I’ll be able to spin the globe and every little part of the world will feel like home.”

A major turning point in my life is when I read this little idea deep in a book by Steve Pavlina called Personal Development for Smart People […] he said, no, the extreme way to be surprised is to move somewhere far away from home, to a culture that’s as different as can be, where everyday life will surprise you on a minute-to-minute basis. I’m obviously not quoting that word for word, but that was the idea. And I read that idea and it was like an inception, right? I couldn’t get that idea out of my head. And so about nine months later, I was getting into the process of selling my company, and I realised I don’t need to be here in Portland, Oregon, any more. And I had just broken up with my girlfriend, and I was just completely free and unattached to anywhere and anything. And that idea came back. I said, that’s how I want to spend the rest of my life.

I was almost 40 years old, and I thought, “I’ve spent the first 40 years of my life in the US. I want to spend the next 40 out.” And ideally, I want to keep going to more and more difficult places, and each one, stay long enough until it really feels like home. Until it’s like, this is my place, these are my people, this is absolutely my home. And then move on and do it again. And the ideal, the big lightning bolt of a vision in that moment, was that someday I’ll be able to spin the globe and every little part of the world will feel like home. From Kazakhstan to Peru to Saudi Arabia to whatever. Finland will feel like home. I’ll have friends there. I will have spent significant time there. I’ll feel really deeply connected there before I die.

What a cool mission. So that’s what I set out to do. It was 2008, 2009. I had just sold my company. I went off into the world. I went to London for six months, five months, and it really felt like home. So much home that I almost bought a house there. I was like, “Oh, that’s it, I’m done. This is my favourite city in the whole world. I’m gonna buy a house.” I put an offer on a house. Luckily, that offer was refused, because I had to slap myself and go, “Wait a minute. What am I doing? It’s just the beginning of my journey.” And sure enough, over and over again, over the last whatever number of years it’s been since then, I get to a place, I live there for a while, I feel really attached. So attached that I say, “Never mind, this is it. I want to buy a home here. I’m going to live here for the rest of my life.” And again, I have to slap myself and go, “Hold on, wait. This is what I’m supposed to feel. And when I feel this, it’s time to move on again.”

From Manager to Consultant

So every culture, or even microculture, has its own moment where the boy is considered a man, where somebody goes from childhood to adulthood. Some have a bar mitzvah. In my case, I felt it when, just a few months ago, he flew by himself from Wellington to Auckland to Singapore, did the immigration and everything by himself, flew on the plane as an adult, and I just met him in the airport in Singapore. And I went, “Wow, you did it.” And I just noticed internally, something in me shifted. I’m like, you know, he’s really not a kid any more. He’s a young man now. He’s 14 and a half. Wait, no. Anyway, he’s turning 15 in a few months.

And so in my head, I had to adjust that. For kids, I think parents might need to be more of a manager and help make decisions for them. But at a certain point, you have to change the mindset from being a manager to being, like, a consultant. To put it more bluntly, they fire you as a manager, and you just have to hope that they will hire you back as a consultant.

Edited Transcript

Jim O’Shaughnessy
Derek, you are absolutely one of my favourite polymaths, one of my favourite people in general. And I read…

Derek Sivers
You too. Sorry, I have to interrupt you to say, yeah, you too. So, audience listening: I took a year-long podcast break. Actually, it’s been a little more than a year. I’ve said no to every podcast request for over a year. And then Jim emailed and asked. I said, “You know what, for you, yes.” I really loved our conversation a few years ago. I just adore you and what you’re doing. And so yes, no to everybody else and yes to you.

Jim O’Shaughnessy
Thank you so much. It truly does mean a lot to me. I want to hit you with something you said, because it resonated so deeply with me. And again, I think it’s one of the reasons why we vibe so well together. You said, “I want to make articles, books, websites, music, companies, systems, apps, and especially new ideas.” And I read that and I laughed and I said, “Me too.” But then I thought, you’ve talked a lot about your son, and I’ve been really incredibly impressed with your commitment to him. 30 hours per week, giving him your completely undivided attention. I mean, I don’t even touch that league, and I have three kids. By giving him that 30 hours a week, did you get lots of things out of it as well?

Derek Sivers
Perspective. I think that’s a huge one. When everybody’s freaking out over an election, over AI, over something in the news, over whatever, I’ve got the perspective that my kid and I are out in nature, or he’s fascinated with a book, whatever it may be. It keeps the world events in perspective for me. I never forget what’s most important here.

Jim O’Shaughnessy
Absolutely. And if you could put yourself in his shoes, does he realise how unusual that type of commitment from a father is and was?

Derek Sivers
In his words? He said, “I seem to be the only kid that has a dad.” He said, “You know, all my friends at school, they either literally don’t have a dad or their dad is kind of barely in the picture.” He said, “I’m like the only friend I know that has a dad.” So to me, the thing I wanted to communicate in action, not just words, is that he is more important than anything that might come through any screen.

Jim O’Shaughnessy
I have the greatest of admiration for that. I remember... I was young when I had my first child. I was 24.

Derek Sivers
Wow.

Jim O’Shaughnessy
And my parents were saying, “You don’t know what unconditional love is, Jim. You really don’t.” I was like, “Yes, I do. Yeah. I mean, I have unconditional... Mom, I have unconditional love for you. Dad, maybe not as much. But Mom, certainly for you.” And then I held my son Patrick, and I started to cry, and I realised in that instant that they were right. I really didn’t know what that feeling was. And it’s an emotion. We’re going to get into that a little later, because I think we both agree that, for the most part... well, I think it was... my friend Rory Sutherland says, “We think that our brains are the Oval Office, when actually they’re the press office.” We make many of our decisions emotionally and then pepper them over with rationality. I used to put a GIF up on Twitter that says “Because of reasons.” But your son is making a big move right now. He’s decided to move to Singapore. And you quipped that you’re trying to figure out how to move from being his manager to being his consultant. How’s that going?

Derek Sivers
That’s a new change. So, sorry, to be clear, he’s not planning on moving to Singapore. That was just our moment. So every culture, or even microculture, has its own moment where the boy is considered a man, where somebody goes from childhood to adulthood. Some have a bar mitzvah. In my case, I felt it when, just a few months ago, he flew by himself from Wellington to Auckland to Singapore, did the immigration and everything by himself, flew on the plane as an adult, and I just met him in the airport in Singapore. And I went, “Wow, you did it.” And I just noticed internally, something in me shifted. I’m like, you know, he’s really not a kid any more. He’s a young man now. He’s 14 and a half. Wait, no. Anyway, he’s turning 15 in a few months.

And so in my head, I had to adjust that. For kids, I think parents might need to be more of a manager and help make decisions for them. But at a certain point, you have to change the mindset from being a manager to being, like, a consultant. To put it more bluntly, they fire you as a manager, and you just have to hope that they will hire you back as a consultant.

Jim O’Shaughnessy
And I love that point because it is so true. The idea that it’s horrible for a child not to fire you as the manager. I kind of see that as a failure to launch.

Derek Sivers
Yeah.

Jim O’Shaughnessy
And my wife was more emotional about it than I was, but I was incredibly proud when each of my children (I have a son and two daughters) came in at roughly similar ages and said, “You know, Dad, I really appreciate your advice and what you’re telling me I ought to do, but I’m going to make this choice. I’m going to decide what I want to major in. I’m going to decide where I want to live.” And I was like, yeah. Because, as I mentioned, we were young, right? We were 24 years old. But we talked a lot about how we wanted to raise our children, and the line that we could both agree on was: we want them to be great adults.

Derek Sivers
Yeah.

Jim O’Shaughnessy
And when you make that your watch phrase, right, it precludes all sorts of things that people naturally go to. “My house, my rules.” “Because you’re living under my roof, you’re going to follow my direction.” And that doesn’t make a great adult. That makes a compliant, sheepish, non-curious individual. And in a similar fashion, I have a pretty good memory for anything I read. And so my kids (this is pre-internet for the most part, or early internet) would use me as Google. “Hey, Dad, you know who was the French representative at the Congress of Vienna?” Talleyrand, in case you’re curious. But we had a massive bookcase, and I would just look at them and say, “Look it up in there.”

And we had the whole family together, which doesn’t happen too often, because one of my three, my daughter, lives in California and the other two live out here on the East Coast. And we were reminiscing about it, and all three kids basically said the same thing. When we were... when they were saying, like, well, what did you like about the way... you know, “How did we damage you, first off? But what did you like about the way that Mom and I raised you?” And all three said that what it instilled in them was that voracious curiosity. Because inevitably, if you’re trying to find out that it was Talleyrand at the Congress of Vienna after the Napoleonic Wars, you’re going to run into some other material if you’re actually looking it up in books.

And one of my kids was like, “Yeah, I read for like a couple hours. I was fascinated by the French Revolution, and that led to my curiosity about other things.” And so I think it’s a measure of your success, in my opinion, as a dad, that he wants you to be a consultant now and he’s asked for that, and you’re absolutely willing to go that way. What do you think are going to be the main differences, acting as a consultant as opposed to a manager?

Derek Sivers
I’ve been slowly prepping him for this for years. So let’s take a little example of whenever he has a school holiday. Here in New Zealand they have two-week holidays three times a year and then a one-month summer holiday. So whenever it’s a two-week holiday, I let him decide what he wants to do with it. His mom has a full-time job, but I don’t. So all the school holidays are on me to take him around or do something, or whatever he wants. So there have been school holidays where he says, “I don’t want to do anything. I just want to stay home and do nothing.” I said, “Okay.” And then he’ll pay the consequences of that if halfway through he regrets it and wishes that he would have gone somewhere else.

Jim O’Shaughnessy
Right, I have to stop you, because that goes against every fibre in your being.

Derek Sivers
How so?

Jim O’Shaughnessy
You’ve often said that you want to take action. You don’t want people who just want to Netflix and chill, right? So did you flinch a little when he said that?

Derek Sivers
Oh, of course. Yeah. So I could give more examples. Like, if he said, “I want to go to Europe,” I’m like, “Really?” Or three years ago, he said, “I want to go to China.” And I had only been to China once before in my life, and it was rough. It was not pleasant. It was 2010 and I went to Guilin and it was pretty nasty. And so when he said he wanted to go to China, I said, “Why?” And he said, “You know, Kung Fu Panda. It just seems interesting.” And I went, “All right. You know, in the name of your education, you lead the way. You go plan the trip. You decide where we’re going to go.” And so he did.

And it ended up blowing my mind, you know. So now I love going to China, and I’ve made a bunch of friends there, and I’ve been a bunch of times since, but it was because he was leading the way. But it can work either way. There have been times, even on a day-to-day level, where he will choose to say, “Let’s go have an adventure. Let’s go sleep in the woods, but without a tent. Let’s just bring the sleeping bags and a tarp. I want to sleep in the woods tonight without a tent.” I’m like, “Okay, if that’s what you want.” And halfway through, he really regrets it. In the middle of the night, he’s like, “Dad, I hate this. Let’s go in.” I’m like, “I thought that would happen.”

But the important thing for each of these examples is that I want him to feel the consequences of his choices, so he leads the way. I’m his faithful assistant, but I want him to get lots of experience leading the way, feeling the consequences of his choices first-hand, so that, yeah, he feels the pain of a bad choice or the joy of a great choice of his own, instead of me making those choices for him.

Jim O’Shaughnessy
Yeah. I have some grandchildren who are approaching the tweener category, and I was talking to my son, who’s their dad, and one of the things he said, which was very adjacent to what you said... we were talking about how much you’re going to allow them to make up their own minds and do their own thing. And he said, “As much contact with reality as possible is what I’m going to advocate.” And I was just like, God bless you. Because in this era where everything is just, you know, helicopter hovering, “Don’t do that. Do this.” I mean, that’s a horrible way to turn out a good adult. You are constricting them and putting them in a straitjacket. It’s just, don’t do that. Don’t do that. Let them make mistakes.

Let them come into contact with reality, because that’s understanding the consequence of your own actions.

Derek Sivers
I think one of my favourite parenting sentences was “Broken bones heal faster than fears.”

Jim O’Shaughnessy
They really do.

Derek Sivers
Isn’t that great? Like, you see your kid climbing on the edge of a cliff, and everything in me is just saying, “Watch out.” But instead of, like, “Wait, no, watch out,” I’m just gonna sit and observe, and if he falls, he breaks an arm, so be it.

Jim O’Shaughnessy
Didn’t Hemingway say we are stronger at the point of the healed bone fracture? Something along those lines. We are much stronger after it heals, at the point of fracture. And so I think that as difficult as that impulse, not to... “Don’t do that,” is. I mean, obviously, I have very young grandchildren, too, and, you know, the first couple of years, you’re essentially trying to stop them from killing themselves. But when they get to a point where they are able and capable to make their own decisions, I am entirely in your camp. Let them do that, because that’s the only way that they’re going to be able to really learn, you know, exactly the way the world works. Moving on. I’ve heard that you yourself are thinking about moving.

Derek Sivers
Yes.

Jim O’Shaughnessy
Which, when I first saw it, I was surprised, given what we... In our previous conversations, you were like, “New Zealand is it.”

Derek Sivers
Oh, really?

Jim O’Shaughnessy
Yeah, yeah. You were like, “This is the place. This is, like, the perfect environment for me.” It didn’t surprise me when I read it. I’m like, of course Derek is going to move. But elaborate on that. What...

Derek Sivers
Yeah.

Jim O’Shaughnessy
Why? Why move from New Zealand to Bangalore?

Derek Sivers
Okay, so, context. I should write about this soon. This was a real key moment in my life. A major turning point in my life is when I read this little idea deep in a book by Steve Pavlina called Personal Development for Smart People. It was an okay book, a little too verbose. And this brilliant idea was like 300 pages in, where it said, if you want to keep growing and learning, you need to be surprised. And one of the best ways to be surprised... no, sorry. He said a good way to be surprised is to read a bunch of books about subjects you know nothing about, and try to do things in your community that you ordinarily wouldn’t do, join groups that you ordinarily wouldn’t join, do hobbies you ordinarily wouldn’t do. And he said, no, the extreme way to be surprised is to move somewhere far away from home, to a culture that’s as different as can be, where everyday life will surprise you on a minute-to-minute basis. I’m obviously not quoting that word for word, but that was the idea. And I read that idea and it was like an inception, right? I couldn’t get that idea out of my head. And so about nine months later, I was getting into the process of selling my company, and I realised I don’t need to be here in Portland, Oregon, any more. And I had just broken up with my girlfriend, and I was just completely free and unattached to anywhere and anything. And that idea came back. I said, that’s how I want to spend the rest of my life.

I was almost 40 years old, and I thought, “I’ve spent the first 40 years of my life in the US. I want to spend the next 40 out.” And ideally, I want to keep going to more and more difficult places, and each one, stay long enough until it really feels like home. Until it’s like, this is my place, these are my people, this is absolutely my home. And then move on and do it again. And the ideal, the big lightning bolt of a vision in that moment, was that someday I’ll be able to spin the globe and every little part of the world will feel like home. From Kazakhstan to Peru to Saudi Arabia to whatever. Finland will feel like home. I’ll have friends there. I will have spent significant time there. I’ll feel really deeply connected there before I die.

What a cool mission. So that’s what I set out to do. It was 2008, 2009. I had just sold my company. I went off into the world. I went to London for six months, five months, and it really felt like home. So much home that I almost bought a house there. I was like, “Oh, that’s it, I’m done. This is my favourite city in the whole world. I’m gonna buy a house.” I put an offer on a house. Luckily, that offer was refused, because I had to slap myself and go, “Wait a minute. What am I doing? It’s just the beginning of my journey.” And sure enough, over and over again, over the last whatever number of years it’s been since then, I get to a place, I live there for a while, I feel really attached. So attached that I say, “Never mind, this is it. I want to buy a home here. I’m going to live here for the rest of my life.” And again, I have to slap myself and go, “Hold on, wait. This is what I’m supposed to feel. And when I feel this, it’s time to move on again.”

So I have not been doing that mission as planned, because I was in a one-year relationship with a woman, and after we broke up, she got pregnant, and oops, that’s where my son comes from. And unfortunately, she hates travel, and she’s his mom. So here we are in Wellington, New Zealand, where Mama works for the government in Wellington. And I’ve been here for 14 years, pausing my mission. But now my boy is also kind of one foot out the door.

He really wants to go away to boarding school somewhere. He’s also got this travel lust. He feels like a world citizen. He was born in Singapore. He’s a citizen of four countries. His mom’s from India. We’re both citizens of India as well because of her. So he’s yearning to get out into the world. So that’s the background context. Do you want to ask anything about that before we go to Bangalore in particular?

Jim O’Shaughnessy
Yes, I do.

Derek Sivers
Okay.

Jim O’Shaughnessy
And, big surprise, right, your son... where would he like to go to boarding school? Does he have a particular place that he wants to go already, or is...

Derek Sivers
He just, like... I don’t know. Jim, can you pull some strings somewhere? What do you got?

Jim O’Shaughnessy
The honest answer is yes, I probably could.

Derek Sivers
He just wants to get out of here, honestly. There’s a school in Kobe, Osaka, a Canadian school in Kobe, Osaka, he likes. There’s a school in Tamil Nadu, India, he likes. There’s the United World College in Phuket, Thailand, that he likes. He just wants to get out of here. He just wants to travel.

Jim O’Shaughnessy
He’s got good taste. Those are... I’ve been to all of those places.

Derek Sivers
Wow.

Jim O’Shaughnessy
Okay. Yeah, yeah. Those are all sweet, sweet spots. And you’re going to let him... Are you going to act like the consultant, or are you going to act like the manager when he comes in?

Derek Sivers
Oh, come on, take a guess. Yeah, no, this is totally his doing. His choice. The applications and everything, he’s doing them himself.

Jim O’Shaughnessy
Yeah. What does he think about you wanting to move to Bangalore?

Derek Sivers
Oh, he loves it. He would do it in an instant, too, if Mama said okay.

Jim O’Shaughnessy
Yeah, yeah.

Derek Sivers
He loves it there.

Jim O’Shaughnessy
It’s interesting to me that she hates travel. She seems to be maybe the other... My wife once joked that she made me a regular, normal human being, so maybe that’s what’s going on. It sounds like he inherited your love of travel and novelty and everything else. Yeah. How does Mama feel about that?

Derek Sivers
Totally against it.

Jim O’Shaughnessy
Yeah.

Derek Sivers
So here we are. Yeah, it’s, you know, it’s interesting. We all probably, at some point in our past, especially when dating, have felt this feeling of trying to be who you think the other person wants you to be. And so I think when she met me, and she saw that I was quickly passing through America on my big international journey, she basically brought out that side of herself and said, “Yeah, I can’t wait to leave America. Let’s get out of here forever.” Even though, in hindsight, that was probably, you know, 1% of her felt that way. She brought out that 1% and presented it to me as who she is. So we were dating under that mindset.

And then as soon as we actually did leave America, like, literally as the plane is taking off, she freaked out and said, “I want to go home. I want to go home.” And so it turns out that she didn’t actually want that. She thought she did. And I was critical of that at first, of course, because it affected my plans very deeply. But in hindsight, I realised, yeah, we’ve all done versions of that. You meet somebody and you bring out the side of yourself that matches who they are. Maybe even just in the name of making friends. Yeah. You meet somebody that can relate to a side of you that’s rock and roll, into heavy metal or whatever. So you kind of bring out that one thing.

Even if there’s just one heavy metal band you like, you’re like, “Oh, heavy metal, yeah, I love Iron Maiden.” You bring out that side of yourself in order to have a bond or connection with this person. And then you meet somebody else that’s really into quiet and poetry, and so you bring out that side of yourself. “Oh, yeah, E. E. Cummings is one of my favourite poets.” You know, we know how that feels. And so you can’t fault somebody for doing it, especially when dating. But, yeah, that’s what happened. That’s why I had a kid with somebody that hates travel.

Jim O’Shaughnessy
You know, as you were talking about how we change ourselves for people that we love, I recently reread a thing by Tony de Mello. I don’t know whether you’ve read any of his work. He was an Indian guy. He unfortunately died way too young. He was a Roman Catholic Jesuit priest who got enlightened in an afternoon he spent with a rickshaw driver who was dying. And he said, “Can I just pay you for the rest of the day and talk to you?” And the guy was like, “Yeah, absolutely.” Anyway, that’s a much longer story, but it got me into all of his books. And the thing that I reread was about love, especially for a spouse or a partner. And Tony’s view was pretty hardcore. It was this: if you cannot say to your beloved (and that’s the term he used, “your beloved”), “I leave you free to be yourself, to seek out what interests you, to follow your own passions, to follow your own interests. And if we still are together, that’s lovely, but if we aren’t, that’s going to be lovely too.” He goes, you don’t actually truly love that person if you can’t say that to them. He said, because then what you’re doing is a transaction. It’s conditional. “If you do this, then I will give you, or do, this.” And it made me really think quite a bit about just the nature of intimate relationships, et cetera.

And kind of do an inventory on how many in my own life were, you know, if you were being just really blunt about it, are they transactional or not? And unfortunately, I found that too many of them actually were transactional. Now, lucky for me, I found a lot that weren’t. But it’s natural for us. I mean, you know, we’re memetic creatures, and mirroring, and especially if we really want to get with somebody, or want to date them or marry them, we’re going to make a lot of concessions. And then what happens? I’ve been married 44 years to the same woman, but what happens is, generally speaking, that goes on for the first, oh, seven years, if you’re lucky, and then you start reverting back into, you know, the real you. And that’s when the challenge comes, right? If you can make it through that.

If you can make it through “But you always said you loved...” “Actually, no, I fucking hate it, and I just really don’t want to do X, Y or Z any more.” If your wife or husband can say, “Okay, that’s fine. That’s great,” things are going to look pretty good for you. But I hear you, and it’s actually quite true. I was reviewing our last conversations, and you put us both in the Miles Davis, David Bowie camp, right, where we just want to try new things. A lot of people are happy to just kind of get good at something and then just do it, right? Just, like, same shit, different day. I hate that. I know you hate that. What do you think it is about people like us who just... “No, I don’t want to keep doing that same thing. I want to try new things.”

Derek Sivers
Okay, wait. I’m feeling that discomfort of a loose thread that we didn’t tie up, because I started to answer your question about why Bangalore, and then I got on my long tangent about how I wanted to...

Jim O’Shaughnessy
Let’s do Bangalore and then we’ll come back.

Derek Sivers
I feel I should close that loop. So, yes, Bangalore. Anybody, if you’ve not been there: the city itself is awful. It’s terrible city planning, terrible infrastructure, but the people there are so wonderful. Kind of in the same way that when I met you three years ago, as soon as we started talking, I was like, “Oh, I like this guy. You’re one of my favourite people to talk with.” And that’s really rare, right? So it can happen with places. So to me, Bangalore is the number one spot in the world where almost everybody I meet is such a great conversationalist. I don’t know what it is about that place, but the people I met there are just so fun to talk with. And I just feel such kindred affection and intellectual stimulation. I just love the people there.

So that, to me, is why Bangalore is top of my list of where I plan to live next, as soon as I can leave New Zealand. I don’t mean to make it sound like there is somehow a move against New Zealand. That’s why I had to give the bigger context. When you said, “Why do you want to move to Bangalore? You said you love New Zealand,” that’s why I had to say, yeah, I want to love everywhere. I also loved Santa Monica, living on the beach. I also loved Oxford, England, and I’d probably be living there still if Covid didn’t send me back. I also loved Woodstock, New York. God. I also loved living in Union Square in New York City. I lived there for a few years.

There have been a bunch of places that I loved, and now Bangalore adds to that list. And don’t be surprised in the future if you also hear me say, “Okay, I am moving to Shanghai.” “Okay, everybody, announcement: I am moving to Istanbul.” You know, I hope to continue to move to places and stay there for a while and fall in love and move on. So there’s the context for Bangalore.

Jim O’Shaughnessy
And just to have my end of sewing that thread up: that’s what makes life fascinating, interesting, enjoyable. I can’t imagine not wanting to experience something new, not wanting to learn something new. I would be beside myself. It would really just bum me out. Before I sold my company, an asset management company, I’d really grown tired of just the same speech, the same questions, the same, the same. And so I would try anything to mix it up, right? So I’d make sure I read the local newspaper so that I could change what I was saying to people.

I would look for something interesting that was way outside of asset management, that you could nevertheless weave in, and get people to go, “Oh, I looked at it that way.” But it just got to the point where it’s like, just doing the same thing, it just turns your brain off, I think. Well, yeah, you’re nodding. And I know that you are a very similar mentality to my own.

Derek Sivers
Yeah. Well, I assume that you brilliantly just transitioned back into the next topic that we left, that you were just about to open, which is that... completely accidentally. Oh, really? So some people can just dive deeper and deeper into one thing. This is maybe the comparison we made last time, of AC/DC versus David Bowie. Some people just want to really perfect that one thing, you know? I don’t know Georgia O’Keeffe’s whole career, but it feels to me, from what I know of Georgia O’Keeffe as a painter, she was trying to get deeper and deeper into this one style of painting. Whereas Picasso went through many different phases and tried different approaches. Got famous for his Cubist thing, but that wasn’t his only thing. So it is possible, I think, to not stagnate while still doing one thing.

Some people just have that personality type. They can just dive deeper and deeper into one thing or one place. They can stay in one place. I feel it’s almost a fault of mine that I can’t imagine staying in one place for more than a couple years. But some people get really into one place, really commit, and they’re able to completely thrive and flourish in that one place, or in one career, one expertise, going deeper and deeper into classical piano or whatever it may be. To me, I think my value system, of what it means to live a good life, a full life, is to do lots of different things. I just have this idea of being on my deathbed, looking back and going, “Wow, look at all those places I lived. Look at all those different things I did. Look at all those different lives I lived in my one life.” That’s what I’m aiming for. I want to live lots of different lives in my life. And hence my last book, called How to Live. It has, like, 27 different opinionated versions of “Here’s how to live. Here’s what to do.” “Live for the future.” “No, no, live for the past.” “No, no, live for the present.” “No, no, just get rich.” “No, no, no, do nothing.” And that book was really a reflection of my soul, because that’s how I really think. I want to live many radically different lives in my one lifetime. So that also leaves me very non-judgemental about any given philosophy or approach to life.

I could imagine living a very greedy life for a while, and living a very altruistic life for a while, and living a very hedonistic life for a while, and living a very diligent, prudent life for a while. Like, why not embody all of these different approaches to life, non-judgementally, to see how they feel, and just try them out, to know that you did it?

Jim O’Shaughnessy
Amen, brother. Because I love the addition of the non-judgemental. I think that so many people get it in their noggins that, you know, this is the one true path. If you deviate from this one true path, you’re either a heretic or, you know, an other. I mean, one of the things that’s really bothered me about, oh, maybe the last 10 years is just all of this tribalism, and all of this othering, and all of this labelling, and all of this, you know, God, “If you’re not with us, you’re against us.” And no, try to understand the other point of view. I’m hugely into AI, right? I’ve kept journals since I was 20, actually younger. I don’t have many good quotes in the earliest ones, but from 20...

I have been waiting for AI. I called it synthetic intelligence in a 1984 journal. I’ve been waiting for it all my adult life.

Derek Sivers
Before it was cool. Just say it. Come on, just say it.

Jim O’Shaughnessy
Before it was cool, I really was into it. And so now that I have it, I’m like a kid in the candy store. One of the things that I do is I just routinely take something that I think I’m really vehemently opposed to, and then I go to the large language model and say, “I want you to steelman this point of view.” And then I read it, and I think there hasn’t been a single time when I haven’t thought, you know, they actually have a point with this particular thing here. And it’s, to me, so liberating, because it’s just like putting it in a bin and labelling it and saying “bad” and “I’m opposed.”

Because when you do that, you shut down your reticular activating system and you don’t see any of it. Your brain literally just makes you blind to it. I could send you the text, I could send you the link to the article, and if you had put it in that bin and labelled it as bad (I’m not saying you specifically), yeah, it just goes away. And so I think that the non-judgemental part of it is the key. And, you know, it also feeds into, like, Claude Shannon’s information theory, right? Information theory. Basically, he posits that information is novel. And he says, if you’re looking for the information coefficient, or how much information is in a given thing... and then he gives the example: a poem is filled with information; a political speech has none. Because one is simply trying to get you, through repetition, to go, “Yes, that is the right path. Yes, that particular policy is the one that people like me are going to support.” The people like me, right? And I like people who aren’t like me. I like to talk with people who are completely different than me, because I always learn something. I mean, I had a profound conversation. I was in Miami, and my wife and I were walking along, and there was a very rough-looking character, clearly a member of a motorcycle gang, sitting in the place a bouncer would sit in front of a club. And so I figured he’s the bouncer, and he’s tatted up and he’s smoking, but he’s not smoking, he’s vaping. And this is back when vaping was brand new.

And I looked at my wife and I go, “Look at this. He’s vaping, he’s not smoking a cigarette. I gotta go ask him.” She’s like, “Don’t go. Leave him alone. Don’t go over there.” Anyway, I go. And I’m like, “Hey, I just got to ask, what’s the deal? Why are you vaping and not smoking?” And he’s like, “My old lady said she’d throw me out if I didn’t quit cigarettes. So this is the next best thing.” Anyway, that was our introduction, but we got into, like, a 45-minute conversation...

Derek Sivers
Oh, I love that.

Jim O’Shaughnessy
...about, like, how do you know who you’re going to let in and who you’re not? And he started giving me all the tells for people that he knew were going to bring the energy down, versus the people who would bring the energy up. And actually, I put that into my toolkit, because he was right about a lot of the things he said. And so it’s just like, if you’re willing and you’re able to, those kinds of conversations can be just filled with gems that you yourself are never going to think about.

Derek Sivers
I love that. That’s what I’ve been trying to do with reading books like Understanding China’s Worldview by David Li, which is a wonderful book that tries to explain, from the Chinese government’s point of view, here’s how they see things, here’s why they feel that what they’re doing is the right thing. And you could do the same with any culture on earth that you think is wrong, or the people are bad, or it’s evil, if you try to see it from their point of view. It’s fascinating, because countries themselves, in my mind, are embodied philosophies. Every country, or even some cultures inside a country, are embodying a certain approach to life.

Jim O’Shaughnessy
Yeah.

Derek Sivers
Through governance. And so, for the most part, unless it’s a complete disaster, it is a valid working philosophy. It might be a messy one. It might not be your favourite in the world. But it’s valid, and it’s great to understand somebody else’s working philosophy.

Jim O’Shaughnessy
And what did you take away from... Actually, since the last time we talked, which was three years ago, in ‘23: what would 2023 Derek think... If you could think of an example that 2023 Derek would be shocked that you did in 2026. Like, “Oh, I can’t believe he did that.”

Derek Sivers
Ooh, that’s a good question. Huh. I have one, but it’s one that I promised not to tell, so I can’t tell that one yet. Ask me again in a couple of years and I can tell. But let me think of what I can say. Actually, let’s go back just one year, to 2025 Derek.

Jim O’Shaughnessy
Okay.

Derek Sivers
All right. I don’t know if this doesn’t need to be secret. I really want to live in China, partially for a few reasons. Wait, have you been there? Or where have you been in China?

Jim O’Shaughnessy
I’ve only been to Hong Kong. I’ve not been to the mainland.

Derek Sivers
Wow, okay. Oh, Jim. Okay. Such a huge difference between Hong Kong and even just... you could walk across the pedestrian bridge and you’re in Shenzhen, and it’s just a night and day difference. Amazing. So I really, really like the quality of life in Chinese cities. I haven’t been to the countryside much, but the cities are so nice. It’s almost like the way that we used to think of Switzerland, this kind of top-of-the-Human-Development-Index kind of quality of life, where everything’s amazing, everything’s perfect, everything’s beautiful, everything’s clean, everything’s great. That’s what the Chinese cities are like now. So, number one, comfort. But number two, the kind of thing we’re talking about, you talking to the bouncer: trying to really deeply understand somebody else’s contradictory worldview.

Contradictory to the one that you grew up with, the one that comes naturally to you. Trying to deeply understand that different worldview. As I said earlier, I want to do that by living in places. Not just visiting, not just reading the books. I really want to try living there until it feels like this is home. So China, OMFG. Hell yeah, I want to live in China. So one of the best ways to do that, besides going and hoping that some company hires me to get a work visa, is to incorporate a company. While I was there, I met a Serbian woman who was in the same position. She moved to Shanghai to work for a Shanghai company, but then when Covid hit, the company fired her. But Shanghai was home at that point. She has a husband and a son in school. She didn’t want to leave. And so she found out that you can (this is what I was getting to) incorporate a company in Shanghai for just a few hundred dollars, and pay a local agent to take care of everything, all of the annual filings and renewals and taxes. Total price will cost you about $1,000 a year. And now you, as the owner of a Chinese company, can sponsor your own work visa that turns into a resident visa. So I now...

Jim O’Shaughnessy
Loophole!

Derek Sivers
Yeah, I now have a Chinese name. My Chinese name is Shen Si Wen. And my Chinese company is named, like, Shen Si Wen Consulting Company, where I’m the owner and director. And again, as soon as I am able to leave New Zealand, I will also be moving to Shanghai to live there as the owner of my Chinese company.

Jim O’Shaughnessy
Very cool. Are you going to split time between there and Bangalore, or...

Derek Sivers
That’s my plan.

Jim O’Shaughnessy
Yeah, that’s the plan. I think that for a lot of people listening to this, one of the things that holds people back is this, in my view, sort of irrational desire for certainty, right? The way I look at the world, only a madman is entirely certain, right? I was talking to a colleague before we jumped on here, and he’s like, “Well, there is the sun rising tomorrow.” And I said, “It’s a probability. It’s a very high probability.”

Derek Sivers
I’ve said the exact same one. I love that. I’ve told people before, you know, “It’s not certain that the sun’s rising tomorrow.” And they’re like, “Shut up.” I’m like, “No, I’m serious.” Yeah, okay, thank you. I love that you just said that.

Jim O’Shaughnessy
He goes, “You take things just too far.” And I went, “No, I mean, it’s true. It’s true. It’s a very high probability.” I don’t get worried about it because, again, if it doesn’t come up tomorrow, I won’t be around to feel that anxiety, right? But I think this illusion of control (and I use that term specifically, it is an illusion of control), I think people cling to it and become almost desperate when they can’t feel a sense of certainty about things. And I think that has caused more problems, in my opinion, in a variety of human societies than almost anything else. This idea that... well, you express it very well in your books. Like, is it true? What’s true? Right?

And I have conversations with people who are super bright, super switched on, everything, and then I hit that wall, what I call the wall of their certainty.

Derek Sivers
Yes.

Jim O’Shaughnessy
And I make an effort to try to chip away, but I think it almost is an emotion rather than a rational belief. Am I just babbling here?

Derek Sivers
No. Okay, I want to try to join you in this topic. I’ve never talked out loud about this, so I hope I’m able to communicate this. Okay. I’m picturing one of those little sliders. Say you have a bar graph that’s a set width, and say two thirds of it is blue and one third of it is orange. But you can move the little slider over so it becomes, say, three quarters orange and one quarter blue. Right. Okay. So, to me, let’s say that orange and blue are a desire or a need for certainty, and the other one is the need for uncertainty. I think some people, in their nature, have a desire for more certainty than other people. And I think that’s just a DNA nature kind of thing. Who knows where it comes from?

But just like you have three kids... if you’ve ever had two pets, you know that even little pets have different personalities. Even if they’ve never been more than a few inches apart their whole life, there is this nature. And some people do just have a nature that wants more certainty, and some of us have a nature that wants more uncertainty. But the reason I’m thinking of it as a slider is it can move. In times where, say, you’re feeling sick, like, you get really sick and you don’t want any uncertainty right now. “I don’t want any adventure. Cancel those plans. I just want to be home in my comfortable bed. Never mind this whole adventure. I’m sick.” I’ve felt that, too.

I was off adventuring far away, and then I got Covid while travelling, and suddenly I was just curled up into a ball. It’s like, “I want to go home.” And it was interesting to feel that. I didn’t want to meet anybody new. I didn’t want to try anything new. I just wanted to go back to my familiar, because I was feeling so helpless or weak.

Jim O’Shaughnessy
Yeah.

Derek Sivers
But then that gives me compassion for people who feel that way a lot of the time. And some of them I’ve been very close to, that just their whole outlook on life is like, “I’m barely hanging on here. I’m barely making it through the day. I don’t want to hear any of your crazy big ideas, Derek. I don’t know. I do not want to go to China. I do not want to go to India. I want to go to my favourite restaurant, and I want to watch my favourite show, and I want to go sleep in my bed. That’s all I want.” You know, maybe because they’re feeling weak, they’re feeling a desperate need for more certainty. And okay, I can understand that now. I have felt that myself.

But some people go through life like that. Maybe their slider’s over at 90%, that they want 90% uncertainty, and just a tiny little bit of, you know, “Two weeks a year I’ll go to Europe for a holiday” kind of uncertainty. That’s enough for me. Yeah. But we can’t fault somebody for having that slider in another place, because it might be their circumstances. You could imagine, like the movie Trading Places, that if suddenly they were flipped into a different position, they suddenly win the lottery of life, they’d feel full of confidence. They wouldn’t feel helpless any more. They’d feel full of daring, risk and adventure. And they’d say, “You know what? My slider has moved. I know I used to be that way, but yeah, let’s go to Afghanistan. Give me a rifle. Let’s see what happens.”

You know, they might be full of adventure, the same person, same DNA, but their circumstances can change them too.

Jim O’Shaughnessy
So I actually love that, because you’re absolutely right. Having been there, getting Covid... I was lucky enough to get Covid. I was one of the patient zeros. I got Covid before anyone knew that it was called Covid.

Derek Sivers
Once again, before it was cool.

Jim O’Shaughnessy
Well, this is an area where I was desperate to not be cool, because, literally, I was alone in my apartment in Manhattan, and I called my wife, and I said, “I’ve got the worst flu I’ve ever had. My temperature is 105, and I haven’t eaten anything. Will you please come take care of me?” And she was like, “Let’s see how you’re doing in a couple of days.”

Derek Sivers
Wow.

Jim O’Shaughnessy
And it’s funny that it’s the same illness, because I felt exactly like you did. I was like, “Oh, man.” Normally, if I’m sick, I’ll read a bunch of books, I’ll watch TV, I’ll do something, watch a movie or documentary that I never got to, et cetera, to keep my mind occupied and to, you know, learn something new. Man.

For the first four days of that, nothing. All I had to drink was water. Didn’t eat anything. The fever ultimately went down, and obviously I got better. And then, of course, when I re-emerged, then the lockdown starts. I’m like, “Oh, great. I just spent 14 days on my own, and now we gotta do it.” At least I’ll have other people. But I do... In fact, I think you could take that even further, right? People who are in very chaotic circumstances. I have some people who work for me who are from the Ukraine, and they still have family in the Ukraine. And it’s hard for me to conceive when they tell me the average day of their parent who’s living in Kyiv. And I just tried to model that in my own head.

And I’d be like, I would be so out of there. And so that’s an area where I would move my dial over to “I want much more certainty.”

Derek Sivers
Yeah.

Jim O’Shaughnessy
Yeah. So I like that distinction. I think that makes a ton of sense. You know, the last time we talked, we were also talking about the idea that ideas were wonderful multipliers, but execution is where you create the value. Now, now we have AI. Okay.

Derek Sivers
I hadn’t thought about this.

Jim O’Shaughnessy
Yeah. And one of the things that I’ve thought about is, we can now get a competent first version of a company, of an app, of anything. And then where do we find the scarce part of execution? If we can press a button and have it one-shot a beautiful website that meets all of our specifications, right, so it’s our taste, it’s everything that we want... where is the scarce part that execution brings? Is it in judgement? Is it knowing the audience that you’re making it for? Is it taste? What do you think?

Derek Sivers
My only real answer is, I don’t know. Yeah.

Jim O’Shaughnessy
That’s a great answer, though.

Derek Sivers
I had not thought about this at all. So I could spout some crap off the top of my head, but it would not be worthy of your audience’s intellectual...

Jim O’Shaughnessy
One of the things I’m actually proudest of from my prior asset management career: I had a guy come up to me as I was leaving the firm that I sold and starting my new adventure. We were at a party, and he said, “You know what I really like about you?” And I said, “No.” And he said, “You’re one of the few guys that I ever saw on CNBC who said ‘I don’t know’ so many times.” He goes, “One time I was watching you, and you said ‘I don’t know’ maybe three or four times.” And he goes, “I turned to my wife and I said, ‘I trust this guy.’”

Derek Sivers
Nice.

Jim O’Shaughnessy
Because we all feel so compelled, right, to have an answer. Right, right? And for the most part, Derek, we don’t know yet. The honest answer, if you’re going to be completely candid: “I don’t know. We’ll see.”

Derek Sivers
Do you think it’s related to this? The stereotype of the quiet person that’s sitting at the table full of opinionated people, that hasn’t said anything the whole time, and then when they do speak up, we pay attention, because, “Oh, really? Now they’ve got something to say?” I think pretty universally across the world, people admire the person that only speaks when they’ve got something important to say. But isn’t it interesting that the algorithms reward content creators that spew constantly, whether there’s something to say or not? And I, of course, rebel against that idea. So that’s why people on my mailing list... I have an email list. One of the problems is, if I don’t have anything to say, I don’t say anything. So sometimes they don’t hear from me for 10 months, and then I send out the first email in 10 months.

And sometimes people go, “Who are you?” Like, “Oh, you signed up to my mailing list a year ago. Sorry, I had nothing to say for the last 10 months.”

Jim O’Shaughnessy
You know, I find that is inconceivable to me. It would be inconceivable that you would have nothing to say for 10 months.

Derek Sivers
Well, nothing public to say. I don’t know. I’m still working on my stance on this, but, you know, there’s a bunch of stuff, like I brought up earlier: “I don’t know. Should I move to China? Should I move to Bangalore? Should I start a company in China? Should I do this?” Decisions around building my house. I mean, there’s obviously lots going on in my head the last few years, but it just didn’t feel like it had any public value. You know, it felt like it was all just really internal stuff, and I hadn’t yet distilled or extracted some universal life lesson from it.

Jim O’Shaughnessy
Yeah. Well, and, you know, I was thinking about it too. We are a lot alike in so many regards, but if you have a company, like I do and you did, where you had employees, it can make it a challenge for the people who work for you. By that I mean they’re seeking direction, they’re seeking stability, right? And I’m willing to pivot on a dime, and a lot of people really resist that. And so I wondered, maybe I’m just a horrible leader. Because in many respects, who gets elected, right? And this isn’t just a phenomenon in the United States. It’s kind of everywhere. The person who gets elected is the one who seems the most certain. He or she is the one who... “Yes, of course we’re going to do this and this. This is my programme. And I will never back... I will die on that hill.” Again, I was talking with my colleague earlier, and I personally take the George Patton view of: I want the other poor dumb bastard to die on his hill.

Derek Sivers
Nice. I hadn’t heard that. I like that.

Jim O’Shaughnessy
I don’t want to die. Every time I see “I’ll die on this hill,” I’m just like, “Oh, what a waste. Why? What if you’re just completely wrong?”

Derek Sivers
I like that. You know, if I could do it all over again: at my last company, I was also a bad leader. And I’ve thought a lot about this. I was experimenting and exploring, but still, quote unquote, leading. Okay, sorry. I picture the classic 1800s British explorer with the pith hat on, going in with the machete into the jungles of Africa to go to some land that the British had never been to before. And that’s all about the exploring, right? “Let’s go up here. Let’s try this. Oh, let’s go in that. Oh, that’s a cave. Let’s... no. Okay, we’ll come back out of that. What if we go up here? Nope, that’s nothing. What if we go over here?”

So you and I have an exploratory approach to life, which is fine and wonderful and valuable and fun, but what a pain in the ass to follow an explorer. Imagine the troop of people carrying the chests, following that British explorer into every little crevasse and then back out again. “Oh, no, that’s quicksand. Reverse.” But the way I think it would happen is that explorer would find a great harbour through, you know, exploration number 97. He finally finds something valuable, and so he notifies the Queen: “Hey, we found a great harbour. I think this would make a great port.” So then the Queen appoints a bullheaded leader with blinders on. He goes, “Right, we’re going to that port. Here’s why. Here’s the benefit. Here’s the outcome. Here’s where we’re... let’s go.”

And it’s a straight line that’s easy to follow.

Jim O’Shaughnessy
Yeah.

Derek Sivers
So whereas it was a drag to try to follow the explorer, it’s actually kind of fun to follow a straight-line leader. You know exactly what you’re in for. You know exactly where you’re going. No surprises. Hey, it’s like that certainty-uncertainty thing we talked about, right? Most people want more certainty. So you get a lot of certainty by following the straight-line guy. And then he just goes straight to that harbour and sets up the port there. That’s it. If you tried to say, “Hey, you know what, what if we tried going this way instead?” he’d say, “Shut up.” Yeah. Okay. Now, in hindsight, if I could do it all over again, knowing that I have an explorer, experimenting personality, I would keep my explorations and experiments private. I would not tell my staff about them, because your staff are not your friends.

I mean, even if you’re friendly, they’re not... you know, there’s a conflict of interest.

Jim O’Shaughnessy
Yeah. The agent principal problem.

Derek Sivers
Right. So I would keep my explorations private. And only when I had, metaphorically, found a harbour that could be a great port, then I would publicly play the straight-line leader to my staff and say, “Everybody: made a decision. This is where we’re going. This is how to get there. This is why. This is what you can expect at the other end. It’s a straight line. Let’s go.” I would have to delineate that side of myself. Yeah, I’d make straight lines for my staff to follow.

Jim O’Shaughnessy
Yeah, I did that ultimately with most of the companies that I founded, just because it worked, right? It works much better. It didn’t stop me from being me and doing all of the above. And I didn’t keep it entirely private, let’s be honest. I shared it with several of the people I knew who could handle it. But yeah, that was one of the things that I learned. And then when you put it on yourself, well, of course you don’t want somebody up there: “You know what we’re gonna do? No, wait, no, we’re not gonna do that. Wait, hang on. No, actually, we’re gonna...” You’re gonna go, “Get the fuck out of here, man.”

Derek Sivers
“I read this interesting book last night. What if we tried this?” I get the feeling you’re laughing out of recognition, because, yeah.

Jim O’Shaughnessy
Oh, totally. Recognition.

Derek Sivers
I did that too. It was literally like I read the book Maverick and I was like, “Hey, what if we had profit sharing?” “What if we just split up the company equally between the number of employees? I just read this book last night. What if we tried that?” And like two months later, I’m like, “Never mind, change my mind.” They’re like, “You fucking asshole. You asshole. You told us that the company was part ours.” I’m like, “It was a good book.”

Jim O’Shaughnessy
I changed my mind.

Derek Sivers
Changed my mind. There was nothing... that was quicksand that way.

Jim O’Shaughnessy
The other thing that we talked about last time was the barcode biz. And essentially, just to refresh your memory and our listeners’ memories, that is something that can be very difficult for an individual to do. In the instance of our conversation, it was musicians and barcodes, if I’m correct. But when somebody comes together and collectivises, it becomes very easy for that individual to get what they need. What do you see today as a barcode opportunity?

Derek Sivers
Ooh, I’m biased, because it’s the thing I was literally working on yesterday, this morning, and today after we hang up the phone: my page called Tech Independence. I don’t know if you’ve seen this. The URL is sive.rs/ti, as in Tech Independence. For 30 years I’ve had a very anti-corporate approach to technology. I kind of... I have a punk approach to this. Very anti-business. I hate it when big businesses try to turn tech into something very corporate and over-engineered and awful, full of formalities. Oh, to me, the spirit of the mid-90s, the brand new World Wide Web invention, was this rebellious...

Jim O’Shaughnessy
Punk rock anarchy.

Derek Sivers
Yes, it was, it was like punk tech.

Jim O’Shaughnessy
It was amazing.

Derek Sivers
And so I want to keep that punk tech approach. I like it, and I think a lot of people don’t even know about it. They don’t even know that this is a possibility: to take a punk approach to tech, and to use it as the antidote to the corporate formalities that you’re usually surrounded with. So Tech Independence, at a shallow level, is just teaching people how to get off the cloud. How to delete your Gmail account and run your own mail server. How to delete your Dropbox account, because you just don’t need that if you have your own server. Just get your own domain. It’s 5 bucks or 15 bucks to get a domain. Point it at a server that costs you a few dollars a month.

Here’s how to run your own server, so that all of these, quote unquote, “we’ll do it for you” services can be kicked to the curb and ignored, because you can do it all yourself with a little server for $4 a month. So I ended up writing all of these instructions onto a page on my website called Tech Independence. And version one was a long, detailed “Do this. Here’s exactly what to do. Type this, go here, click that, copy, paste this, put this into the command line. Now make your SSH keys and do this.” And it was like a hundred steps. But if you follow these hundred steps, you’ll have your own server. Version two was me putting 50 of those steps into a script that you could run on your server.

So now it’s 50 steps, and copy this script and just run the script, and it will set up your mail server, your web server, your con... your calendars and contacts. What else? Your Dropbox-style file thing. Anyway, just the last two days I’ve been working on version three, which is taking care of even more of it for you, but giving more education at the same time. So the script will do it for you to save the typing, but it will also give you a plain-text description of what we’ve just done, to copy and paste, so that you can paste it into an AI now and say, “I am running OpenBSD 7.9, using relayd and the HTTP server. I’ve got an SSH account that’s locked in for my user only. The server is hosted here. I have root on this server. And now my problem is that the SMTP mail server is not relaying mail.” So it lets you copy-paste some context for your situation. And then you could ask the AI to either solve the problem, or even, “Can you teach me some more about what I have just created?” Because all I wanted my Tech Independence script to do is to quickly give you the experience of having your own server. I didn’t want to lay out a hundred different options. It’s just very paint by numbers. Go exactly here. Go to vultr.com, get a domain. We’re going to set up the OpenBSD 7.9 server. We’re going to use this web server, this mail server, this concert calendar... I keep saying “concert” by accident. I mean contacts and calendar server.

And just, bup-bup, do exactly this, and within minutes you will have your own server, so that you can be tech independent and shut down your Gmail and whatnot. But I also want people to understand what they’ve done. So I think it’s interesting that AI can make us more dependent on it if we’re not careful, but it can also make us more independent, because with the exoskeleton of AI to strengthen our abilities, we can replace things like Gmail, or replace things like Dropbox, that we were previously dependent on. You can learn how to set them up yourself.

Jim O’Shaughnessy
Yeah, I like that idea, and I completely agree with you. I have this idea that almost everything is a dual use, right? Like, you know, we discovered fire. Amazing, amazing things fire did for us. We started to cook our meat and we got the prefrontal cortex that we hadn’t had before, and that was, yeah, yay, prefrontal cortex. But fire is also incredibly dangerous, and used the wrong way can be incredibly destructive. We didn’t ban fire. We invented fire alarms, fire departments, fire warnings, fire extinguishers, fire everything. And so whenever I hear either of the extremes, right, like, “No, AI is going to bring us into a utopia”... no, it’s not. Nor is it going to turn us all into paper clips, right?

We will learn. When bad things happen (and bad things will happen; they happen with any new and powerful invention or technology), we will learn. “Oh, huh. We better put up, you know, much more of a strong firewall, so this can’t just escape through from its sandbox.” And so I definitely agree with your notion that, depending on the way you use it, it’s either going to dumb you down, because you’ll just say, “Oh, all I got to do is press this button and I get everything I want,” or teach you. And all of a sudden you take all of these... Ken Stanley wrote a great book called Greatness Can’t Be Planned. And he basically talks about the fact that once you get to a certain place, you see things differently, obviously, right?

Because you’re changing your location, you’re going to see things differently and experience things differently. And when you get to that new space, it’s good that you see things differently, because you’re like, “Well, I had intended to go up there, but now I see, oh yes, that’s very inhospitable up there. There’s a lovely meadow over this way. Let’s go this way.” And so I think something where people, like you’ve just described, can use it in a fairly easy-to-use manner, but also learn... Oh, because guess what? The minute you learn that new thing, you’re like, “Hey, wait a tick. I could also do this and this.” And that’s how you grow. That’s how you get new things. Thank God for the tinkerers, in my opinion, right? Because... yeah, no, go.

Derek Sivers
And it’s also just so fun. I’m so glad that you could relate to the punk tech thing I said earlier, because what I’ve had so much fun using AI for lately is to teach me how to replace the bits where I was still dependent. So, okay, since you said the tinkerers, that’s why I had to interrupt here. Imagine this. You have a domain name. Is it osv.llc, right?

Jim O’Shaughnessy
Yeah, that’s right.

Derek Sivers
Okay, so osv.llc. You registered it somewhere, at a domain registrar. And DNS is the name of the thing at the registrar that makes it so that when somebody types osv.llc in their browser or their email client, it knows to send the web traffic to IP address number 123.45.67.8, and to send the email traffic to mail.google.com, or whatever you’re using for mail. So that’s called DNS. And I’ve been online for 30-something years, and I’ve always just used the DNS that was built into my domain registrar. So recently I started moving my DNS to a separate DNS server called bunny.net, which I was very happy with. It’s a company out of Slovenia. I’m very happy with them. They’re great.

But along the way I said, “But I’m still using some external company to do this thing. It’s just low-level tech. How hard could it be?” So I was like, “Dear ChatGPT, teach me how DNS works and how I can set up my own DNS server.” And so it guided me towards creating something that is actually more secure than using some other company, which is called the hidden DNS master. So on a private server that has nothing pointing to it, that’s secret, but at a data centre, I built my own DNS server. Sorry, I’m using a standard, secure OpenBSD DNS server, but basically it’s super low-level, doing it myself, running the same software that these other providers run, but I learned how to administer it myself. So now, for all of my domains, I am the DNS master.

And then I use a company called ClouDNS that just pulls from my master, and they’re like the public CDN, firewall type thing. So the public gets it from them. But I’m the sole source of DNS, so doing it this way, it’s actually way more hack-proof. Worst-case scenario, if somebody hacks into my account at ClouDNS, I go... it’s just a shrug, because I’ve got the secret hidden master that nobody can get into. So that was an interesting low-level thing to learn, because along the way I learned how DNS is working at a very low level. And it was so educational. Same thing with running your own mail server, running your own web server. Instead of just going, “I don’t know, it’s at WordPress somewhere,” you can have the AI... “Hey, show me at a very low level how I can create, like, a hello world type basic service here, and do it myself.” And what I love the most about this (and I just found that I was elated for days while I was working on this) is that it is so non-commercial. I’m just there in a black terminal with the code, and nobody’s pushing, you know, upselling at me, or whatever. It’s just so beautifully non-commercial that it reminds me of that punk tech joy that I got out of this in the first place.

Jim O’Shaughnessy
I love it. I love it. You know, as far as the whole punk thing goes, I look at the scientific method as kind of pure punk rock anarchy. And by that I mean, take no one’s word for it. “No, no, that’s not the correct answer. I think there might be a better answer, and we’re going to keep looking until we find a better one.” I think that it’s a function of just the insatiable curiosity which... back when the whole Age of Reason began, the Enlightenment, there was this thing called the Republic of Letters. Are you familiar with the Republic of Letters?

Derek Sivers
No.

Jim O’Shaughnessy
So it’s really cool. Back in, you know, the 1700s, educated people all around Europe were discovering all these interesting things, and they would write very long letters to one another that got passed on. What would happen is, I would write you a letter and you would think, “Oh, this is a pretty good idea. Oh no, Jim really screwed the pooch on this one. This is not a good idea.” And you would annotate. You would say, “Derek here. No, I don’t think this one works, and here’s why.” And the one you liked, you’d say, “Yes. And what you forgot to mention was this.” And then you’d forward that to another friend who also had the interest. This was a real thing, and that’s how a lot of the news of when calculus, for example, got invented... You know, Leibniz was saying, “I invented calculus,” and Newton was saying, “No, I invented calculus.” And part of that controversy was because all these people were sending letters back and forth to each other. “See what Newton did?” “Well, yeah, but did you see what Leibniz did?” And so that was this explosive, almost Cambrian-like explosion of knowledge, from this interaction in the Republic of Letters. And then the Royal Society institutionalised it. Institutional capture. They formed the Royal Society. And guess what? Societies that want to go on and have authority and all that, well, they’re going to have a lot more rules, they’re going to have a lot more protocols, they’re going to have a lot more “This is acceptable. This style is not acceptable.” And it’s not that at that time it fell off a cliff.

But much of, say, peer-reviewed science today, it’s just so incremental. It’s so... “Are you kidding me?” And so I think that the true scientific method is very much of the ethos that we’re talking about here.

Derek Sivers
I love this. I’d never thought about that, but I think you’re so right. And Richard Feynman is so punk.

Jim O’Shaughnessy
My favourite physicist.

Derek Sivers
But think about it. He was really outspoken in saying, like, “I don’t care who you are. I don’t care what your degree is. You verify your work against the experiment. Show me your work. I don’t even care how beautiful your theory is. Do the experiment.”

Jim O’Shaughnessy
That’s all. If your theory is the most beautiful theory in the world, it’s more elegant than any theory that I’ve ever seen in my life, and the facts say it’s wrong, it’s wrong. Get over it.

Derek Sivers
Yeah. You know, I’ve tried... I want to dive into this punk subject. Anybody listening to this, if you please, email me if you have any insights into punk philosophy. Because whenever I’ve tried to look into it, I just keep getting steered into punk music. And I’m like, okay, well, I don’t like the music. I like the ethos, the ethics, the mindset, the rebellion, the something, the lack of formalities. And I love that you just brought science into this. Science as punk. That’s a beautiful example.

Jim O’Shaughnessy
Yeah, because it is. And that’s what true discovery is. And, you know, whenever you get an institution that wants to capture attention, wants to capture value, wants to capture all of that sort of stuff, a lot of that fun stuff, the stuff that got them there in the first place, stops happening. And that’s a mistake if you want to forever learn more, expand more. You know, I’m a huge fan of David Deutsch. I don’t know if you’ve read his book.

Derek Sivers
Yeah. Okay, wait. You know what? We’re deep into the podcast. Who knows if you... I dated his goddaughter in Oxford. And so every night after our dates, I would drop her off at David’s house. And so...

Jim O’Shaughnessy
Oh, my God.

Derek Sivers
I didn’t meet him, because we broke...

Jim O’Shaughnessy
Not an envious person by any stretch of the definition of the word, but that makes me envious.

Derek Sivers
I just assumed that... I thought we were going to keep dating. I liked her a lot. I thought we were going to keep dating, and I just assumed that I would meet him. But then we broke up and I didn’t meet him, and then Covid hit and that was that. Another reason I loved living in Oxford. Sorry, I just have to smile with sweet memories when I hear the name David Deutsch.

Jim O’Shaughnessy
His book The Beginning of Infinity is a sort of a definitive look at how I look at the world.

Derek Sivers
Nice.

Jim O’Shaughnessy
I read it when it came out in ‘12, and then I reread it in ‘23 or ‘22. I can’t remember. I got so much more out of it the second time.

Derek Sivers
Oh, good. I should read it a second time. I really also loved it the first time.

Jim O’Shaughnessy
It’s worth the second read. Let’s do something fun. I’m going to put you on the spot, for once.

Derek Sivers
Okay.

Jim O’Shaughnessy
I love the fact that you take... I am, right now, just to give you context, I am writing... I’ve written four books, but they’ve all been non-fiction books. So I thought, you know what? I’ve always wanted to write this, and this is true. I’ve always had this idea for a fictional thriller-type novel, for the last 35 years, and now I’m writing it. And the first thing I learned was fiction’s got hands. By that, I mean it’s a hell of a lot harder than non-fiction. And I always admired you for the care you gave each sentence, right? You would write a sentence and then you’d write it 10 different ways. Can I put you on the spot?

For our listeners and viewers, give me a sentence, and then show me all the ways that you got to that sentence from other ones. If you could do it from memory.

Derek Sivers
Ooh.

Jim O’Shaughnessy
Because you’re so good at this.

Derek Sivers
I wish I could. I don’t remember the final sentence. Damn it. In my book How to Live... I just don’t have it right here, man. If I was one of those guys that... if I was sitting at the computer while we were talking, I would just pull it up. But okay. But I remember there was this one idea that was a combination of something I read in a book, that then was combined with a conversation with a friend, and then enhanced by a conversation with a different friend. And all these sources together had this big idea. Kind of like you and I have talked around a few ideas, like straight-line leadership, or punk tech, or the scientific method as punk. We’ve talked around an idea.

But for my book How to Live, I was writing so succinctly, like poetry, that I just kept... I took a paragraph and made it four sentences, and I took those four sentences and made it three. And I took those three and I made it two. And then I took that two and I made it one, but it was still too long. And I cut out all the unnecessary words. And finally, what I was left with was this one sentence. It was like ten words. And I looked at that going, “God damn, that really does sum it up.” What a nice feeling. And even the choice of words: I’m constantly reading things out loud and choosing the words that sound nice in the mouth, that roll well off the tongue.

Because ideally, I still have this songwriter in me that wants things to be catchy. So with my newest book, Useful Not True, the goal was to make it so catchy that, in theory, if I were to practise for just, say, a few weeks, I would be able to stand up on stage and, word for word, tell you the whole book from memory. Because it’s only 88 pages. The average chapter length is 22 sentences. And I should be able to memorise that book word for word, and stand on stage like one of those people that puts on a one-man show on Broadway. I should be able to do that book word for word.

And, audience, we paused for me to go find the sentence that I was so proud of: “Pain’s power relies on surprise. If you expect it, it’s weaker. If you choose it, it’s gone.”

Jim O’Shaughnessy
Wow.

Derek Sivers
It just made me so happy. That was, like, hours of conversations and rambling ideas. Yeah. “Pain’s power relies on surprise. If you expect it, it’s weaker. If you choose it, it’s gone.” And that’s in the context of the chapter called “Pursue Pain”. So the whole idea is, if you decide to deliberately follow the painful path, because you know it’s better for self-improvement, or learning, or greater rewards, then the pain is gone, because you’re choosing it.

Jim O’Shaughnessy
It’s like Jung saying that as long as you try to fight your demons, you will only strengthen them.

Derek Sivers
Oh, and Oscar Wilde said, “The way to resist temptation is to yield to it.”

Jim O’Shaughnessy
Yield to it. I love Oscar Wilde.

Derek Sivers
Yeah, he’s always good for the classic quip like that, reversing the expectation of the line. But, I mean, so, writing fiction: are you following any structural best practices, like an outline that they say makes a great story? Or are you just fully immersing in the...

Jim O’Shaughnessy
I read Joseph Campbell at length. I read a lot about how to write good fiction. I have kept journals forever. I’ve been a writer all my adult life, so... But I’m not following the hero’s journey. I’m immersing. I’m immersing after having read, or in many cases reread, those books. And I figured, since we have the publishing company, I’ve got an amazing group of writers working for me. So we’re also using a writers’ room, and we’re putting AI editors and writers in the writers’ room. We want to give the whole thing a whole different take. We’re going to try a very different way to get a really cool story. And it’s been ridiculously fun, because when you start, you’re just an idiot. I would have my colleagues say, “Well, what do you think of this?” And, you know, they try to be nice. It’s like, “Well...” So what I finally did... we also have our own AI stack. We have our own hardware, our own software, everything. And so it’s not nerfed. It’s much more helpful than some of the commercially available ones, because you’re not lobotomising it. Anyway, what I found the AI was best at was actually criticism. So I would put a chapter in, and it would give me all the pluses and minuses. And then I’m like, AI is... even our own AI is a bit sycophantish. So I wrote a very long prompt that created one of the best-educated, most erudite critics, who is going to hate every chapter that I write. And Derek, I gotta tell you, that was the best of any of the feedback I got. Because it was vicious. It was beyond vicious.

And at first, you don’t get mad, because it’s a machine.

Derek Sivers
Yeah.

Jim O’Shaughnessy
If a human being that you were fond of sat opposite you and said those incredibly vicious things, you would be so hurt that you just couldn’t function, right? When it’s a machine, you just read it. You’re like, “Well, that’s kind of picky. That’s kind of...” Then you read it again, and then you’re like, “It’s absolutely right. I’ve written this character completely in the wrong tone. I’ve got to completely rethink the way I think about this.” And then it just started getting better and better. So my vicious critic prompt in AI proved to be, like, the absolute best feedback I got anywhere.

Derek Sivers
I love this. I wonder how the AIs... I could totally imagine them having the structure frameworks in mind. I’ve never written fiction, but I find it fascinating. I’m a film buff. I didn’t even realise this about myself until a film composer told me what a film buff I am. I’ve read maybe three or four of these books now that talk about story structure and film structure, and how to make a plot that keeps you hanging and keeps you involved and makes you feel like you’ve arrived in a different place than where you started. And who is the protagonist? The protagonist is the one that changes the most. You know, things like that. And I find them fascinating, even though I’ve never used them. But I have written over 120 songs with the same approach. You could call it formulaic, but it’s taking the lessons from what have made the best songs so good, and using those techniques to write your own song, using them as inspiration. And so my favourite phrase about this is “Restrictions will set you free.” If you’re just given a blank page and someone says, “Make something. Go,” you’re stuck. But if somebody says, “Okay, start here, then after this change to that, but then double-time it in the middle, and then go to this, and then end higher. Use these three instruments and these six notes. Go.” Well, now those restrictions set you free.

Jim O’Shaughnessy
Absolutely.

Derek Sivers
Because now you’ve got so many ideas sticking within the structure. So if I was to write fiction someday, I think I would probably get so inspired to write, like, 10 different stories using some given framework, that ideally nobody would see the framework underneath.

Jim O’Shaughnessy
Yeah, definitely. And I’m lucky, because we’re using this writers’ room approach. I have some great people for structure, just as you’ve been outlining. And they’re reading it now, and they’re like, “Okay, what you... you had a... the cortisol spike. That’s a thriller. And then it spiked again in a different thing, and it’s the same chapter. No, no, no, no. You got to let each of those spike independently. You got to make this two chapters, not one.” And basically, I was saying the same thing, except in one chapter it was two cortisol spikes, and that was somehow less jolting than the big one in the first chapter and the big one in the second chapter. So I’m very lucky to have a very talented team that can give me that kind of feedback.

But it’s fun because, you know, it’s something that I had wanted to do since I was in my mid-30s, and now I finally got a chance to do it, so that’s exciting.

Derek Sivers
I love this.

Jim O’Shaughnessy
Another thing you did for your book Useful Not True was you studied philosophy for two years, and I love that. I love philosophy. I took a few classes in it, but I’ve read most of the major philosophers. And what I wanted to ask you is: after you studied the philosophy, what could you be confident in saying... that you were fairly confident of an idea before you started studying the philosophy, and then after you did, you’re like, “Yep, that one doesn’t work at all”?

Derek Sivers
I actually have an anti-answer for you, because it made me less confident about my definition of true. I’m still a little surprised that I only agree with the nihilists. And nihilism has such a bad name. It’s used as almost synonymous with Satanism or something. When people say, “Well, you don’t want to be a nihilist,” you know, they just use that as the worst thing that anybody could be. But there is a beautiful little book called Nothing & Everything. Actually, sorry, the first half of the book is beautiful. The author uses a pseudonym, Val N. Tine. And the book is split into two halves. I don’t know what happened in the second half, but the first half is so beautiful and so well written, and just had me yelling out loud as I was reading it, like, “Yes!” And then it’s like, “Part Two,” and I’m looking at this, like, “Ew, what spilled on the page here?” Anyway. But this definition of true that I find most useful... because of what you said earlier, your biggest problem is other people’s certainty. When they get so damn certain, their mind is closed. “That’s it. This is a finished matter, not up for discussion. That’s it.” To me, you should reserve that only for things where there really is no other answer. A square has four sides, and that’s that. There is no other answer. That’s certain. That the sun is going to come up tomorrow, you know, like you said...

Jim O’Shaughnessy
Highly probable.

Derek Sivers
Not certain. Let’s reserve the things we call true for only the things where there is no other answer. And unfortunately, even pragmatism, which a philosophy professor steered me towards... I described it to her, and she said, “It sounds like you’re talking about pragmatism.” So I went and read five different books about pragmatism, and unfortunately, no. I wish that my thoughts would have fit into the philosophy called pragmatism, and I would have said, “This is the school of thought I subscribe to.” But no, it also wasn’t quite right. So, sorry, the only answer to your question is that it made me more uncertain. Which I guess was ultimately my point. I think that Useful Not True is ultimately a book about scepticism. It’s about doubting everything.

Jim O’Shaughnessy
Well, sure. And I wrote a thread on Twitter about my own journey there. And I said, when you go through all of the thinkers, the philosophers, et cetera, most people end up at nihilism. And one of the things that I learned, at least in my life, was you’ve got to walk across the bridge of nihilism. And by that I mean, you get to the other side and you realise, if life has no external inherent meaning, if there is no truth with a capital T, how lucky are you? You’ve got a blank canvas. You can paint your life on that blank canvas. You can make an incredible life, with meaning, with purpose, with all of those things that you decide. It’s entirely bespoke to you. But you gotta walk across the bridge.

Derek Sivers
I love that. You might, you know, even just for the smile and the joy... I don’t know if it’ll teach you anything, but this little book called Nothing & Everything, by...

Jim O’Shaughnessy
I wrote it down. I’m gonna get it.

Derek Sivers
Okay, good. And just stop at the second half. When it gets to the second half, just call it done. But yeah, it’s the only book I’ve ever found that fully dives into what you just said.

Jim O’Shaughnessy
I just love talking to you. I hope I can hooks you on yet again, because I didn’t get to half the things I wanted to talk to you about. You are such a wonderful conversationalist. I always really enjoy talking with you. It’s just so much fun. A lot of people... I don’t know if this happens to you, but a lot of people sometimes look at me and they’re like, “What?” Yeah, we’re weirdos. Yeah.

Derek Sivers
I think last time, didn’t we do a Part One and Part Two right away? So I’d be up for that, if you’d like to.

Jim O’Shaughnessy
Oh, I would love to. I will have Ena send the invitation for the second one, and we’ll get this one out as quick as we can.

Derek Sivers
All right, audience, we’ve just turned this into a Part One, Part Two to be continued.

Jim O’Shaughnessy
Part One, Part Two to be continued.

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This summer in Naples, Brent’s team presented results from three sealed Herculaneum scrolls, including the first read end to end. Their announcement was covered everywhere from National Geographic to NBC News to The Guardian.

Brent and his work are the subject of The Vesuvius Challenge, an upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Spotify

Apple Podcasts

Show Notes

Brent Seales & Nick Tawil

• Dr. Brent Seales: Stanley and Karen Pigman Chair of Heritage Science at the University of Kentucky and co-founder of the Vesuvius Challenge. Brent Seales at the University of Kentucky

• Vesuvius Challenge: The open competition Brent co-founded with Nat Friedman and Daniel Gross to read the carbonized Herculaneum scrolls. Vesuvius Challenge

• The June 2026 breakthrough: The announcement in Naples of new texts, titles, and authors recovered from the scrolls. The day the Herculaneum scrolls began speaking again

• Nick Tawil: Guest host and head of Infinite Films. Connect with Nick

The Scrolls & the Discoveries

• The Herculaneum library: Roughly 1,800 scrolls carbonized by Mount Vesuvius in 79 AD, the only library from antiquity that survived. Vesuvius Challenge: the scrolls

• Philodemus, On Gods, Book 8: A title and author read from a sealed scroll, establishing that the work ran to at least eight books. CNN on the discovery

• The En-Gedi scroll: The burned Torah scroll Brent’s team read without opening, containing one of the oldest known copies of the first two chapters of Leviticus in the canonical Masoretic text. Vesuvius Challenge on En-Gedi

• The $1 million prize: The open competition to fully unroll and read one of the remaining sealed scrolls. Current prizes

Films & Coverage Mentioned

• The Vesuvius Challenge: The upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce. Deadline announcement

• Secrets of the Dead: The Herculaneum Scrolls: The PBS episode following Brent inside the Villa of the Papyri. Watch on PBS

• Cost of Glory: The Roman history podcast Brent and Nick reference while discussing what might still be buried. Cost of Glory

• Dead Poets Society: The source of “carpe diem,” one of the two ideas Brent would give the world. Dead Poets Society

Highlights

Why Brent Launched the Vesuvius Challenge

The acceleration that we were going to get from just going open source was going to far exceed... it was going to far outpace our own ability to just get there. And what everybody wanted was to just solve the problem. It wasn’t so much about owning it or getting sole credit. It was really about delivering these things back to humanity. And we thought that we were right on the edge of being able to do that. And so I think the excitement of being able to get over that cliff, that marker of being able to say, “We’re going to do this,” that put us over the line we needed to be over to be able to say, “Okay, it’s worth opening this up.”

The Authors Are Coming Alive

So I feel like my part... not that it’s completely done, but it’s substantially done. We achieved this moment. And now the people who can read the language are not talking about the technology anymore. They’re talking about reading language, understanding the world. So I think there’s been a kind of change where I’ve completed the technical work, substantially complete, let’s say, where I don’t have to make the case anymore that this is possible. And of course, we’re going to refine the methods so that everything can be faster, everything can be better. But the conversation now is really about the works themselves, and the scholars who can read those works, and what we’re going to learn from the ancient world. You know, until the tech worked, we weren’t learning anything about the ancient world. We were learning about synchrotrons and virtual unwrapping. Now we’re actually reading the words, and the authors are coming alive. And that’s an amazing and a remarkable moment.

Edited Transcript

Nick Tawil
Hey, Brent. Good to have you here today. It’s so good to see you in person again. You’ve been incredibly busy and productive this summer. You are in the news literally all around the world, certainly here in the United States, but also in Italy, Germany, England, France, for the work you’re doing at Herculaneum in Naples, Italy. We had a big June announcement.

I’m privileged to know a lot about this because, you know, O’Shaughnessy Ventures, we’re literally doing the film on you guys. It broke on Deadline a few weeks ago. But I wanted to start my time with you now with an excerpt from an article in Scientific American.

So here it is: “How do you read a book you can’t open? That’s precisely what Brent Seales, a professor at the University of Kentucky, has spent his career trying to figure out. And on Thursday, his life’s work reached a pinnacle. Seales, alongside a huge group of volunteers and scientists working as part of the Vesuvius Challenge, has helped develop the technology to see inside books and scrolls that we can’t open without destroying them.”

Now, use the word... “Your life’s work has reached a pinnacle.” So I don’t think that’s hyperbole. I also don’t think it’s hyperbolic to say that what you’re doing here, and what you’ve been able to do with AI and the X-ray tech that you’ve devoted your entire career for, is probably a watershed moment for understanding our own civilization and our own history, our own civilizational history.

So I guess just to start, how has the summer been? And how has your work changed even in the last couple of months, just in terms of attention you’ve gotten around this? And I want to talk about the actual discovery as well.

Brent Seales
Well, thanks for that introduction. What a great piece. It is astounding, and to hear it read back... you know, every time we think we’ve found a pinnacle, there seems to be a new place. And this summer has been fantastic. The June press event in Italy kind of brought it all back home because, you know, we’re standing there talking about reading these scrolls for the first time using virtual unwrapping, and we’re looking across the bay at the actual volcano. And the time scale is crazy, right? 2,000 years. So it was a very high moment.

And we’ve had a series of those over the last five years. In fact, in 2020, which was the anniversary of the Apollo moon landing, I proposed to my research team, “This would be the year.” And you know what happened in 2020. Soon after those words came out of my mouth, the entire world, you know, goes upside down.

So from there really to now has just been this constant climb, and to get to the top... I mean, I think you’re right that the word “pinnacle” kind of captures being pretty high on this mountaintop of having solved the problem, and turning from the technology really more toward the lost voices that we’re restoring by reading these manuscripts. It’s amazing.

Nick Tawil
So talk to me about where these manuscripts actually live in Herculaneum and how many there are. Give me a sense of scope and scale.

Brent Seales
Sure. I did not know about this collection as a student, and it wasn’t until we started developing this particular technology that I started searching around for likely candidates. And Herculaneum came to the top immediately because it’s iconic. I mean, it was formed... The library at Herculaneum was formed by the volcanic eruption of Mount Vesuvius in AD 79.

Most people are familiar with the story of Pompeii. Pompeii is maybe the birthplace of modern archaeology, and it’s also this fantastical ancient lost city that was uncovered by humanity. Well, the reason why it was lost is the explosion of Mount Vesuvius.

What’s unique about Pompeii is the architecture, the scale and scope of the city. What’s unique about Herculaneum, which is where the scrolls were found, is that it’s the only library from antiquity that survived. We have all the history in the medieval copies of written material that tells us there was a library at Alexandria. People were into books. Books were traveling around the ancient world. But we don’t have any of the actual libraries left, and this is the only one.

So you’re talking about 1,800 scrolls, maybe a couple thousand books. They were all discovered in the realm of 1750 to 1760, when the Herculaneum site was first excavated, and many of them were badly damaged at excavation. But because they were being excavated by the royal family, King Ferdinand and others who were reigning in that part of Italy at the time, they were carefully kept. Some of them were gifted to other kings as diplomatic gifts, but for the most part, the collection stayed in Naples, and from 1750 until now, we have what we have.

And the state of affairs is that the scrolls were badly carbonized, which means that the volcano spared no expense in basically turning them into what looks like charcoal. So you have the only ancient library that is in existence in the world from antiquity, and then you have this profound physical problem that you can’t really unroll or very easily read any of the material.

Nick Tawil
So over the years, the easier scrolls were read and have been read and researched, but there’s just an entire portion that’s unreadable. And so that has basically stayed untouched until now.

Brent Seales
Yeah, absolutely. The ones that could be opened were. Some of the ones were pretty readily able to be unrolled. The volcanic ash and mud that covered up the library varied in how it impacted the collection. So early on, you had some that were just immediately opened. You have a lot of them that were destroyed because as they opened them, they just scraped it away and they made sketches, and now all we have are the sketches. The worst of the worst are the ones that remain. And for some reason, I latched onto that as the problem.

And I don’t know... looking back, you say things like “your life’s work,” but when your life is playing and you’re doing that work, you’re never really sure what’s going to become your life’s work, right?

Nick Tawil
Yeah. Well, what were you doing before this, before Herculaneum got onto your radar as a challenge? What were you doing before that?

Brent Seales
Well, I’m a computer vision and imaging specialist, and I did my PhD work at the University of Wisconsin in the field of computer vision. Computer vision can be defined as making computers and cameras work together to be able to either imitate what humans can do visually or to solve problems in the world autonomously.

So you see computer vision now every day succeeding with facial recognition, autonomous cars, all of the remote sensing that happens. The early days when I started that work led me into applications like manufacturing, autonomous navigation, space exploration. So I was doing work toward those applications. We were doing welding inspection, for example, where you’d have a camera help you watch a weld being made, and then the control loop would help you improve the process of doing those welds. It doesn’t sound super exciting, and I decided that it wasn’t that exciting for me. So I moved through some of those applications.

The thing I was doing immediately before Herculaneum and a lot of the heritage work that I started doing was medicine. You might be familiar with laparoscopic surgery. This is where surgeons will never actually open the operative field. They’ll do an entire procedure through scopes that have been inserted into the body cavity. And it’s incredibly hard to do that work, so the visualization part of doing that work is super important. So I was working with surgeons to try to help them better visualize not only the operative field live as they were doing the surgery, but all of the preoperative stuff that they were doing. You might X-ray a patient in advance to see what you’re dealing with, and then the surgeon would, what, memorize that preoperative stuff so that they have an idea of what they’re going to face when they go in.

Well, all of those things actually fed into what I eventually started to apply to virtual unwrapping, because the X-ray, right, I hadn’t had a lot of experience with that. But it actually became one of the key things that we’ve used to see inside of these books without opening.

Nick Tawil
And not just any X-ray. It’s, what’s it called?

Brent Seales
Computed tomography.

Nick Tawil
And where are these machines at in the world?

Brent Seales
The medical version of computed tomography is everywhere. Every hospital has one. In fact, tomography won the Nobel Prize in Medicine in 1979. The two inventors.

Nick Tawil
What about the X-ray machines you’re using for this project? You’ve had to travel to use these particle accelerators, haven’t you?

Brent Seales
Yeah, the X-ray for Herculaneum... We’ve settled on a synchrotron, and... that’s a very, very unique X-ray source that comes from a particle accelerator. And there are 40 or 50 of these worldwide. We’ve used a few of them in Europe and in America. There’s one at Oxford. It’s called the Diamond Light Source. We’ve also used one in Grenoble, France. It’s the European synchrotron light source. And what’s interesting about the synchrotron is that it produces a very carefully controlled, extremely bright X-ray beam. And brightness with X-ray means that you don’t have to wait as long to collect the images, because you have so many photons going through the sample that you can take a really, really quick snapshot because it’s so bright. So we can do an entire scroll at very high resolution very quickly.

Nick Tawil
What do you mean, quickly?

Brent Seales
Well, the kind of resolutions that we’re talking about now, which have really unlocked the problem, are kind of astounding. You know, the size of a red blood cell is bigger than the resolution that we’re getting to see the interior of the scroll. Every one of the little voxels that represents the scan of this...

Nick Tawil
A voxel?

Brent Seales
Voxel, which would be the 3D version of a pixel. You add that third dimension, you call it a voxel. The size of that little sample is astoundingly small, and that’s what lets us see everything that’s going on inside the scroll, including the ink.

Nick Tawil
Including the ink. And this is the key. Once you can lift the ink, the ink signature, I’ll say, off of the burnt scroll, then you’ve got something to work with. But it’s still tightly wrapped in this sort of cylindrical form. So now you need to... this is where the virtual unwrapping happens.

Brent Seales
That’s right. The X-ray gives you a model of everything that’s going on inside without having to open it, just like it does on the human body. But it’s still all wrapped up and compressed, and not in a form where you can actually do anything. So all those software steps that take you from that scan to the final readable thing, that’s the thing we invented to be able to do it.

Nick Tawil
And this is the Vesuvius Challenge.

Brent Seales
Well, before the Vesuvius Challenge, that was the research problem, which we essentially had solved to the point where we believed we had the formula. The Vesuvius Challenge took us over the finish line because we threw the contestants in there, broke through on the first-ever scroll, and then with the attention that we gathered and more funding, I mean, we just ran at the finish line after that.

Nick Tawil
And so this is co-founded between you and Nat Friedman. The Vesuvius Challenge is an open-sourced AI engineering challenge, so open source, like, presented and set to the public. Anyone could contribute to this project. And you weren’t really sure what you would be able to find when you opened it up like this. And how did your partners in academia, or other researchers and other lines of work, maybe the papyrologists, how do they all... Were they all involved in this at the very beginning? How did they react to this? Is this just helpful to them?

Brent Seales
Yeah. You know, the Vesuvius Challenge was not a no-brainer for me to jump into. It kind of evolved from an invitation that Nat Friedman sent me to just attend a conference into what became the contest. The conference was the chance where I could meet Nat and his colleagues. And in meeting him, I found out that it probably wasn’t going to work to just ask for investment, because there wasn’t that level of interest in the colleagues that he had gathered together for the meeting. But Nat himself was incredibly interested. And of course, he’s a really smart guy and very connected.

So he sat down after the conference, before I went back to the lab, and he pitched me this idea of a contest. And Nat’s an open-source guy. And what I knew that would require is for us to open up all of our research, including our data. So, yeah, I was sent packing back to the lab with this idea from Nat: “Hey, why don’t you just open up everything you’ve worked on for the last ten years, and we’ll do a big contest.” And you can see that maybe that isn’t a no-brainer, because you have to think, who’s been supporting me? What are they going to think about this? Can I just do this on my own? And maybe I should just do that, maybe just put everything on hold and do it on my own.

But we soon decided, as I talked it over with the folks in my lab, my trusted team, that the acceleration that we were going to get from just going open source was going to far exceed... it was going to far outpace our own ability to just get there. And what everybody wanted was to just solve the problem. It wasn’t so much about owning it or getting sole credit. It was really about delivering these things back to humanity. And we thought that we were right on the edge of being able to do that. And so I think the excitement of being able to get over that cliff, that marker of being able to say, “We’re going to do this,” that put us over the line we needed to be over to be able to say, “Okay, it’s worth opening this up.”

But, you know, I’ll be honest. Once in a while, we’ll see, even now in the press, an article that says a teenage college kid solved this problem. And while that might be true in a sense, it’s also monumentally not true, because we have this whole research program going, and then we had this entire Vesuvius Challenge happening. So all of that is the mechanism that has helped us be able to have that kid do that work.

Nick Tawil
Well, we were also talking about this before. You set up the challenge, and people that contribute to it in a meaningful way do get prize money for it. But what ended up really happening was it became a selection... it became an identity signaling, almost talent recruitment, function for you and your team, because the people that ended up contributing to it ended up becoming a part of the team, at least for a period of time. Correct?

Brent Seales
That’s right. And I love that we got the interest that we got, and I love that it became this huge recruiting tool. A much bigger funnel than I could have ever cast on my own. A combination of Nat’s network plus the notoriety of what happened with the Vesuvius Challenge and just the buzz. You know, we had two, three, five thousand people on a Discord channel talking every day. You can’t even... so many messages, you can’t keep up.

Nick Tawil
This is from around the world.

Brent Seales
From around the world. It’s global.

Nick Tawil
And so it’s still going today, the Vesuvius Challenge.

Brent Seales
That’s right.

Nick Tawil
And you run the team still. What’s the next challenge? Well, first, let’s maybe talk about what happened in Naples this past summer, because I think then the question becomes, what’s next? So tell me about the scrolls that were presented in Naples this past summer.

Brent Seales
Yeah. The moment that we signaled this summer in Naples was that we can do a complete scroll. So you give me a scroll, it’s never been opened, I can make a scan of it, and then the software process is now good enough that whatever’s inside, we can unroll and unwrap and present in a kind of complete way.

So we did that in Naples for three scrolls, and we were able to show also what we found in those scrolls. One is an extensive work of at least 140, maybe 150 columns of text. And I mean, that’s going to keep the papyrologists busy for a long time. This is all ancient Greek. It’s very dense.

Another scroll itself was partial, but everything that’s there we were able to unwrap and read, including the title and the author, which is kind of amazing. And a third scroll also gave us another title and an author, Philodemus, On Gods, Book 8, which means that there were at least eight books on gods by this guy, and no one knew that Philodemus had written those books.

So again, that can start more speculation about what’s in the books, what’s in Book 8 we’re going to read. So we unpacked that in June, and what I think it did is it shifted the conversation now from the technical, because we presented the complete technology that can do the whole thing, to the lost voices that are now going to be restored. So there may be 400 of these scrolls left that have never been read. They’re the hardest ones, and we’re reading them. And that is ecstatic.

Nick Tawil
You’ve gone from pursuing history to now actually reading history.

Brent Seales
That’s right.

Nick Tawil
So there’s a sense of completion now that you have around this project.

Brent Seales
Well, I’ve never been able to read any of the ancient languages because I haven’t had that training. So I feel like my part... not that it’s completely done, but it’s substantially done. We achieved this moment. And now the people who can read the language are not talking about the technology anymore. They’re talking about reading language, understanding the world. So I think there’s been a kind of change where I’ve completed the technical work, substantially complete, let’s say, where I don’t have to make the case anymore that this is possible. And of course, we’re going to refine the methods so that everything can be faster, everything can be better. But the conversation now is really about the works themselves, and the scholars who can read those works, and what we’re going to learn from the ancient world. You know, until the tech worked, we weren’t learning anything about the ancient world. We were learning about synchrotrons and virtual unwrapping. Now we’re actually reading the words, and the authors are coming alive. And that’s an amazing and a remarkable moment.

Nick Tawil
How do you refine the process that you basically pioneered here with your team? How long does it take today to read one scroll, and how long do you want it to take?

Brent Seales
I’d love for it to be an instantaneous thing, completely automated, that doesn’t take much longer than the scan time. We’re not even close to that right now. But imagine that you go to the scanner for your receipts from travel, and as long as it takes for it to scan is how long it takes for you to get the OCR and the thing to be uploaded. That happens right now for receipts and things like that. OCR, optical character recognition, was one of those first finally solved computer vision problems, and we would love for the scroll to be the same.

I don’t think that we’re that close to that right now. I think we’re still several years away from that kind of performance, because the technologies that we’re using are not that robust yet. But the computer vision and the machine learning that we’re using constantly improves. And we’re in this era now that is remarkable in that computer vision and machine learning, with more data, can get better. And so we actually see the ability to read the scrolls with the technology we’ve created as something that is going to create versions that get better over time as we read more scrolls. That’s never really been true with any other technology. Like, photography doesn’t get better the more photographs that you take. But because of the way the machine learning works, the more things that we capture, we learn from that, and then we get better at actually revealing the text.

So rather than time to text, which is one thing that we talk about, it’s quality of text, readability. We want to make the job of reading this ancient language the easiest possible. And overcoming the damage is really hard. I mean, this stuff is peeling, it’s fragile, so it’s kind of a miracle that it works at all. And then to say we want it to be pristine.

Nick Tawil
And instantaneous.

Brent Seales
And instantaneous.

Nick Tawil
So American of us.

Brent Seales
Yeah, well, it is. It’s always got to be better, right?

Nick Tawil
Oh, no. Actually, for the machine learning piece and the AI of it all that you and your team have been using to accelerate this process, in order to get it digitally unwrapped and handed over to the papyrologists, it comes across in the film in spades. But it also is something that other tech and VC investors have noticed, and even starting to make a little bit of waves in Hollywood, which is traditionally lukewarm towards AI. But in the film it comes across very, very cleanly, I think, and very authentically, that this is a great use case for AI, a positive use of AI, to further understand humanity. And I think it’s currently presented in the national conversation as either/or: you’re either for AI and against humanity, or for humanity and therefore you have to be against AI. And this is really a nice kind of marriage of the two in terms of a use case.

Brent Seales
Yeah, I see that. I think there’s irony that AI is so forward-thinking and premised on such modern and current technology, and yet we’re using it in this case to look backward. But it’s kind of a rescue mission, if not a sort of redemptive story, right? We’re kind of redeeming these lost works using AI as the tool to do it. And in fact, I like that message, right? That every new tool, including AI, that comes into human purview can be used as a way to redeem what’s around us. And so I think that actually is a really good story, and it’s one we should focus on.

Nick Tawil
So now that you’ve digitally unwrapped these three scrolls, is there a backlog of more scrolls, specifically from Herculaneum, or other labs or other researchers from around the world calling you up, saying, “Hey, you know what? I’ve got this parchment here that I can’t read. What do you think?”

Brent Seales
Well, it’s true that that is happening, and I’m glad that’s happening, because, congratulations, we have the technology to be able to look at some of that material. For example, there are scrolls in Amman, Jordan, from Petra, and they haven’t been opened. They’re carbonized. So there’s more material in the world that this could work on. But there is a backlog of just the Herculaneum stuff. I mean, we haven’t plowed through that. There are 40 scrolls that we’ve already scanned, and that’s 10% of what we think actually remains. So that’s a decade’s worth of work right there.

Nick Tawil
And the full villa hasn’t even been excavated.

Brent Seales
And that’s the next thing, right? The villa hasn’t been excavated. And I think people are a little bit naive about that. They think we have what we have and that’s it. But if you go down to the villa, which is not even open to the public... The villa is a part of Herculaneum that’s separate from the publicly available part of the town of Herculaneum. You go in there and you realize they really just sort of tunneled along the foundations of the villa, and that’s how they infer what the actual architecture of the villa was, and they just happened onto the artifacts that they have, including the scrolls, by doing that tunneling. It’s not fully excavated. And, you know, I’m not an archaeologist, but I would love to see, now that we know we can read the material, full archaeology happen there, not only to find the scrolls, but really to just better understand the villa and the scrolls we already have.

Nick Tawil
Well, it’s also, like you said, it’s the only ancient library that we know of. And what does that say about the authenticity of all these scrolls compared to maybe other artifacts that exist out in the world that academia or the research community currently has and uses?

Brent Seales
I love that you bring that up, because the provenance of scrolls from Herculaneum is unassailable. I mean, you can’t fake the carbonization. You can’t fake something being in this collection for 200 years.

Nick Tawil
So the carbonization actually creates an authentic fingerprint on this thing that cannot be exactly replicated.

Brent Seales
Exactly. Think about the Dead Sea Scrolls and how that all went down in the ‘40s. They were parted out by the Bedouin, so there were no archaeologists on site when they were found. And then you end up with advertisements in the New York Times for, like, a scroll from Israel. And what has happened since then is that we’ve seen a lot of fakes, where somebody will say, “I have a Dead Sea scroll, a scroll from cave number nine, Qumran, whatever.” And it’s really hard to prove sometimes that that’s true or not true. Not true with Herculaneum at all.

The other thing that’s amazing about a library from antiquity is that it’s not been copied by medieval scribes. So you have the original book that was actually on the shelf. So, fully authentic, verifiable, and the original book, not filtered through medieval scribes. And you know that a lot of the philosophy and the religion was tinkered with when the scribes of the medieval period recopied and preserved those works. And the tinkering is not always obvious. Sometimes scholars have to spend a lot of time to figure out, how did this change? They don’t have the original work, they just have the copy. Every book that we’ve read from Herculaneum has been a unique work. It doesn’t exist anywhere else in the canon, and it’s uniquely from antiquity. So it’s really a very, very compelling kind of collection.

Nick Tawil
So how long will it take you to do the next 40, 45 scrolls that you have in backlog?

Brent Seales
Right now we have a new competition that’s been announced, a $1 million prize through the Vesuvius Challenge, and that is for someone else, a competitor using our software, using their own, to do what we just did: read a full scroll from one of the 40. And we’re hoping that that’ll push our techniques forward. It’ll engage the community. Somebody will win $1 million for doing that. I think those 40 are going to be processed this year. That’s my hope. And then we’ll go after the remaining 360, the other 90% of what remains. A lot of those are fragmentary, so we know that we’re not going to have a whole book, we’re going to have a piece. But the game then becomes, if we can read all the writing, how do we put these works back together?

Nick Tawil
Why not grab a frontier lab here to just say, “Hey, we’ll just do this”?

Brent Seales
I’d love that. How do we do that?

Nick Tawil
We should have that conversation.

Brent Seales
We should do that.

Nick Tawil
And then let’s say these scrolls get scanned. How long does it take the papyrologists to analyze them?

Brent Seales
Papyrology is not fast, because what a papyrologist brings to bear when they look at the text is all of the other knowledge about the ancient world, because these texts are dense. Sometimes the texts aren’t fully...

Nick Tawil
You keep saying “dense.” What does that mean? A lot of text in a column, or the messaging is dense?

Brent Seales
Yeah, I mean, sort of intellectually dense. So you’re talking about parachuting into the middle of a book that is probably in the middle of a philosophical argument that a scholar is making, and they’re fully embedded in their time. So they’re talking about a person you don’t know whose name is maybe missing from the text, and about an idea that is only partial. And the game is to try to figure out, from the limited words, all of that stuff, all the context. And it can be really, really tricky and take a long time. Sometimes it ends up just being a mystery. It’s like, we don’t actually know what’s being talked about right here. We have all the words, but it’s really hard to know what the story is.

We’re hoping that most of the virtually unwrapped texts that we can provide are good enough in terms of readability and quality that the scholars will be able to unpack that density and figure it out. But the extra knowledge that the papyrologist has in their head, besides just the vocabulary and the structure of the language, is immense. And that’s what they’re applying, sometimes as a group and not just individually. Sometimes they have to work on it together.

Nick Tawil
So I want to talk more about the tech, and the tech throughout the entire workflow, to include what participants were doing at the Vesuvius Challenge and the challenges that they faced, either individually or as a group, in mapping out aspects of the scan, but then also the actual scan technology, the synchrotron you mentioned a few times. Give me a sense of scope for what a synchrotron is. Maybe start there, because that has to happen first, before you even engage people, your lab and other third-party participants through the Vesuvius Challenge, to even look at this stuff.

Brent Seales
Yeah, that’s right. We started by using a bench source. A bench source is one that you can move around. A bench source for X-ray would be one that you’d find in the doctor’s office or the dentist’s office. And so the first scans that we made, way back in 2009, the first time I ever scanned a scroll, it was done with a source that we took to the place where the scrolls were. It was just so much easier to have access if we were within the perimeter of where the scroll lived, at the library in the Institute of France in Paris. But what we discovered was that that source wasn’t going to give us some data that was good enough to do all the rest of this stuff.

So we quickly moved to the synchrotron, which is a source that isn’t movable. A synchrotron is an X-ray beam that comes from electrons that are running around in a ring at the speed of light. And the ring is like a kilometer across.

Nick Tawil
Just for this one scroll?

Brent Seales
Well, so the ring creates the electrons that run around in a circle, and then when you manipulate those electrons, it creates all of the different beams that you can use from this instrument. So it’s actually a huge campus around this ring, and one of those beamlines would be used to do the work on the scroll at a certain point. And you can tune what that beam is going to be in terms of the intensity of the beam and the energy that it has, all of the things that you think are needed in the characteristics to be able to elicit what you want from the scan. Way more controllability than something that you can take to the library.

Nick Tawil
So you have a lot of control.

Brent Seales
So what it created, though, was this problem of: now I have to take the material to this facility, and I have to guarantee the custodial holder, the people who own the scroll, the institution, that that’s going to be okay, that the scroll will be cared for, it won’t be damaged. So there was a time period where we had to shift to be able to use the synchrotron, but we hadn’t convinced anyone who actually had a Herculaneum scroll that we could do that. So you can imagine kind of going a little bit nuts, knowing that we could get better data, but we have to be able to convince the institution to let us do this thing. Once you get the scroll into the beam at the synchrotron, at that point, it’s really all about how do you capture the best possible scan, how do you optimize over a bunch of different parameters.

Nick Tawil
Which was a learning process.

Brent Seales
Which was a learning process. And the first time that we did it, we got what we got, and eventually we converged on a way of capturing the [unclear].

Nick Tawil
How much does this cost?

Brent Seales
The synchrotron cost, if you’re not being gifted the time, and typically we weren’t being gifted the time, would be $10,000 per shift, where a shift is eight hours. So, you know, a thousand, $1,500 an hour, and add inflation to that over the last two decades, and imagine how much.

Nick Tawil
And it’s the first time you’re doing it. You’re definitely going to have to learn off of that.

Brent Seales
Yeah, sure. And you’re not able to do the scan all in one go. So typically we do what’s called grid scans. You do a small section of the scroll, and then another adjacent small section, and then another adjacent small section, and you do these sections individually and then have to assemble the whole thing. So it’s its own thing to just capture the data and then manage the sizes and...

Nick Tawil
And not ruin the artifact.

Brent Seales
And not ruin the artifact. In a way, we were lucky, because these artifacts are completely inanimate. They’re completely desiccated, and they’re basically carbon, and you almost can’t do anything to carbon with X-ray. It just goes through.

But it’s also the worst case for solving the problem that we want to solve, because the X-ray doesn’t show the ink very well, or at all. There was a period of time, I don’t know if you know this, Nick, that people told me we would never be able to solve this problem, because it would be impossible to see...

Nick Tawil
Who told you that?

Brent Seales
Colleagues.

Nick Tawil
You don’t have to say their name.

Brent Seales
High level other professors, who felt like I was the guy tilting at the windmill, and they tried to sit me down and say, “You know that you’re never going to be able to see the ink using tomography. Carbon is invisible. You won’t be able to see the ink on top of this other surface.” And we refused to believe that, because we felt like there would be evidence. We just didn’t know how to tease it out.

And the two miraculous things that occurred that let us tease that out in a pretty non-obvious way: the synchrotron first. Super high resolution, so you can see the effects at a microscopic level.

Nick Tawil
How microscopic? Down to what?

Brent Seales
Well, a couple microns. A micron is one one-thousandth of a millimeter. So at one micron, you have a thousand slices in the space of one millimeter. That’s tiny.

Nick Tawil
So the two miracles that happened...

Brent Seales
The second miracle was AI, machine learning, because the evidence that is there is subtle. And so you need a tool that lets you amplify that evidence, embedded with so many other signals, because there’s a lot going on inside the scroll at that scale. There are fibers going everywhere, and there’s damage from the carbonization itself, and there are rips and tears and folds. And then somewhere, you know, the ink is actually on the surface of this ancient paper, which is not like normal paper. It’s not a composite that’s really uniform. It’s fibrous everywhere.

And so you have this really weak signal, and you have a pretty diminished modality, which is this X-ray modality. You would love to have visible light, but you can’t. And then along comes this incredibly sophisticated and powerful tool of machine learning that lets you find needles in haystacks, and boom.

Nick Tawil
And this is where actually the human comes in, too, because now you’re focusing AI engineers onto this problem, the Vesuvius Challenge. What are some of the obstacles that they had to overcome?

Brent Seales
Well, we had this huge labeling problem.

Nick Tawil
Labeling what?

Brent Seales
To break through... you couldn’t see the ink in the scans that we were getting with the naked eye, easily or at all. But when we trained the AI based on ink we knew was there... and we did that by using open fragments that had writing visible on the open layer. And then we would scan those with the same tomography, and then we knew where the ink was. We would label it “ink,” “no ink.” And then we could see that the machine learning would learn the evidence of the ink, even though we couldn’t see the ink with the naked eye in the scan. So all of that was scientific control, to be able to prove to ourselves there is evidence of the ink. The AI is learning it, the machine learning is learning it, but we have to label it for it to learn.

Well, how do you label the ink in a completely closed scroll? This was where the competitors gave us a huge boost, because now we have 2,000 people working on this problem, and they’re trying to create labels. And what they would do is they would run a fairly diminished machine learning effort on an open section of the scroll, virtually opened, and they’d see a response, some letters coming out of the mist, and then they would relabel. And iteratively, as more text gets exposed, they get more labels. Now amplify that across the 2,000 competitors...

Nick Tawil
24/7.

Brent Seales
With people sharing stuff, because we did inspire sharing through progress prizes. And so now you have the acceleration that we hoped we would get. The techniques weren’t substantially different than what we had already been doing, but the scale of what was happening, and iterations in terms of innovations were happening too, for sure. People were building tools that were helping. And so then eventually you’re solving this bootstrap problem by doing this kind of one-way ratchet, everything sort of getting better slowly.

And by the end of that year, I think it was 2023, maybe, we were headed toward the final submissions of the Grand Prize. Things were just accelerating like crazy. I mean, people sharing, and text obviously being detected from inside the scroll was very exciting.

Nick Tawil
And that’s when we got wind of it. And so at that point, you have something digitally unwrapped, then passed off to the papyrologists. And that’s a whole flow of work.

Brent Seales
Yeah. And we’re trying to improve that, actually, because it’s not really a one-way street at that point. Papyrologists just have a lot of insight into what looks legitimate and what might be an artifact. An artifact, for example, or even a mistake, might be what we call a sheet switch, where the virtual unwrapping actually gets off of the layer that it’s on and it descends to a lower layer. And the text, if you can read it, is going to tell you that that happened.

Nick Tawil
There’s, like, a break in the narrative.

Brent Seales
There’s a break in the narrative if you’re reading the words, or you can see sort of an obvious artifact that’s not going to be in a normal open scroll. And so we can actually go back and fix those things if they’ve happened. And usually the papyrologists are the ones who pick it up.

Nick Tawil
Oh, wow. So they’re actually involved pretty early on in the process. They’re not just waiting for you to hand them something.

Brent Seales
That’s right.

Nick Tawil
Cool. And then could you tell me a little bit about the scroll En-Gedi?

Brent Seales
Yeah. Before we were making such good progress with Herculaneum, this scroll from En-Gedi came to us through the Israel Antiquities Authority, and in particular the director at the IAA, who at the time was Pnina Shor. She’d heard of our work... we didn’t even know that this was happening, but she’d heard of our work and had found in their collection a scroll from En-Gedi that had been looked at by a number of professors, but no progress could be made because it was too badly damaged, and no one wanted to take on the formidable task of trying to open this little scroll physically, because it just looked like it was in pretty bad shape.

So she’d gotten that scroll back into the collection and then made a scan of it, and she used a bench source, not a synchrotron. And then she gave us the data and said, “Give it a try. We can’t do anything with this, and we can’t see any obvious writing, but I’ve read your work and maybe something can happen here.”

So it didn’t take us long, because this scroll was actually the perfect candidate for the moment in the development of our technology. It was animal skin and not papyrus, so in that way, it was less challenging. And then, as we did the virtual unwrapping, we found out that the ink... it must have been some kind of metallic ink, because the density of the ink in the X-ray was different from the density of the animal skin. So we weren’t looking at the same kind of really, really subtle effects of Herculaneum, where there’s no density difference at all. I mean, it showed up. The ink showed up in the En-Gedi scroll as a very bright signal sitting on top of this damaged animal skin, and boom, the text just appeared.

Nick Tawil
And what did it say?

Brent Seales
Well, that...

Nick Tawil
This text that had never been previously seen before, even by the owners of it.

Brent Seales
The scroll still remains wrapped up. It’s never been opened. But we could read everything inside because of these effects, using virtual unwrapping. And what we found is that it was a Torah scroll. It was the first remnants of the first two chapters of the Book of Leviticus from the Old Testament.

Nick Tawil
Wow. So how old was the scroll that you were given? How old was that expected to be, versus the text you found on the scroll? Is that the right question to ask? Like, “We don’t know what this is. We think it’s this old.” And then you find this. What does that change?

Brent Seales
The text definitely helped to date the scroll. They had carbon-dating evidence that put the scroll second, third century. But it had been found at an archaeological site that was Byzantine, so a couple hundred years later. So those results didn’t make perfect sense. There was disparity between the carbon dating and the archaeological evidence, which... they knew this site is Byzantine, so it’s probably fourth or fifth century. Once we read the text, it made more sense, because they could see the writing. So paleography, which is the analysis of the handwriting, dated it to an earlier era. So it was probably a scroll that they’d had in their collection at this synagogue for a hundred or a couple hundred years.

And as such, it was probably sacred. Something likely catastrophic occurred at that archaeological site, because normally none of the remnants would be in the Holy Ark. I think it was tradition that, the genizah, you would dispose of these artifacts, because they’re holy. And you wouldn’t just bury them or leave them partially burned for others to have. So this was the first time in a synagogue that they had ever discovered Torah. And it also became known as one of the oldest copies of the first two chapters of Leviticus.

And from the text, the scholars were able to tell that it was the canonical version, the Masoretic Text. And it’s a really early example of that settled text, so hadn’t changed. So, pushed the date for the settled Masoretic Text way back. They do have examples in the Dead Sea Scrolls collection itself of variations from the settled text, but this one was dead on the settled text of Leviticus. Pretty exciting.

Nick Tawil
Well, as we talk about this era, and we think about the papyri at Herculaneum, we know that the eruption happened in AD 79, but the scrolls in this villa could be much, much older. Because it was... I don’t know, you tell me, is it the sort of melting pot of a library that was collecting wisdom and scrolls from just around antiquity at the time? Give me a sense for what you would hope to find, or what a historian would hope to find and hope to see, in the remainder of the library.

Brent Seales
I think that the library probably was a place where they had an archive, so they had older texts. Typically, the way I understand it is that resident philosophers would write new works, but they would premise those new works on an archive of other works, often quoting them, extending the arguments in the earlier works, debating with each other, and then writing. So I think it’s very likely that there was an archive of much older works. And if that’s true and we discover those works, you could have literally anything.

It was a Roman villa, so it’s a little mysterious that there’s so much Greek and not as much Latin. So a lot of people have postulated that that’s just an archaeological feature, that it hasn’t been fully excavated. If we were to excavate it, because it’s a Roman villa, we would find much more of the Latin work. And I mean, that opens up all kinds of possibilities. We know of so many things that have been lost from the ancient world.

Nick Tawil
Let’s speculate. Let’s start speculating. I’m not going to hold you to anything, but I want to know.

Brent Seales
Livy’s History of Rome, for example. This would be for Alex Petkas, right? Because he knows everything that’s lost and found.

Nick Tawil
Cost of Glory great podcast.

Brent Seales
Yeah, exactly. Incredible. And then you have all of the literary and philosophical traditions of the Greek schools, so there could be much more of that. It’s thought that this particular philosopher, since we have Philodemus, was primarily an Epicurean. And there were also the Stoics. They argued with each other, and other schools.

If you ask me what I wish we could find, because the first century was such an amazing point in human history, I’d like to find early gospel material. Anything Christian at Herculaneum would instantly become the oldest witness that we have to early New Testament Christianity. I mean, even the fragmentary stuff from the New Testament is second century, for the most part. We have almost nothing from the first century, symbols only. But we know that this is Rome’s backyard. And we know the Apostle Paul was flitting around the world writing letters to the churches, which became part of the New Testament. So you have more than just the synoptic Gospels, which of course would be amazing. I mean, AD 79, right? This is just shortly after the life of Christ. So if there were writings that documented anything about his life that didn’t make it into the synoptic Gospels, those writings could potentially be in a library like this.

In, you know, the recent results corner of the library. I mean, most people who are academics and scholars would argue that it’s far-flung to think about anything that’s really gospel-y, because these libraries facilitated the ancient philosophies, and Christianity was new and hadn’t really taken hold. And I get that, nascent things at that time hadn’t made their way into the canon, the library, the archive.

But on the other hand, it’s fun to think about what could be there. The lost books of the History of Rome by Livy would give us a window into so many other events that would be better than just a philosophical tome. So rather than somebody talking about what it means to live a pleasurable life like an Epicurean, you could have somebody telling you about all of the events that happened as Rome rose and fell, and imagine how that would be. I think the historians would want history books, the philosophers want philosophy books, and the Christians want Christian books.

Nick Tawil
That’s great. Well, here’s to discovering new human knowledge. Thank you, Brent, for your time.

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Show Notes

Ryan Resch & Jimmy Soni

• Ryan Resch on LinkedIn: Former Suns Assistant GM and VP of Basketball Operations, now leading data and AI at 1949 Capital Partners. Connect with Ryan

• Beyond the Dashboard: Ryan’s Harvard Business School interview with Boris Groysberg on optical tracking, dashboards, and AI. Read the interview

• Shore Capital Partners: The private equity firm founded by Justin Ishbia, where Ryan helped roll out AI tools. Shore Capital Partners

• Jimmy Soni on X: Guest host, bestselling author, and editor-in-chief of Infinite Books. Connect with Jimmy

Teams, Leaders & Data Discussed

• James Jones: The 2020-21 NBA Executive of the Year, whose Suns rebuild started with raising the floor. Executive of the Year

• Scott Drew: The Baylor head coach who answered Ryan’s cold email and later had him build lineup data. Scott Drew at Baylor

• SportVU: The camera system that brought optical tracking to every NBA arena in 2013-14. SportVU and the NBA

• Second Spectrum: The machine learning platform that turned tracking data into tagged plays and dashboards teams across the league use. Second Spectrum and the NBA

• Hawk-Eye: Sony’s 3D tracking system, used across the NBA since 2023-24. Hawk-Eye and the NBA

Books, Shows & AI Tools Mentioned

• Moneyball by Michael Lewis: The 2003 book on the Oakland A’s that frames how analytics moved from baseball into basketball. Moneyball

• Hyperion by Dan Simmons: The first book in the sci-fi series Ryan is reading, and a window into how earlier writers imagined AI. Hyperion

• The Founders by Jimmy Soni: Jimmy’s history of PayPal and Silicon Valley, which Ryan handed out at the Suns. The Founders

• TBPN and Dwarkesh Podcast: Two of the tech shows Ryan wishes he had more hours for. TBPN | Dwarkesh Podcast

• Claude Code and Codex: The coding agents Ryan uses in a workspace built for agents to read. Claude Code | Codex

Highlights

When Does Peanut Butter Become a Meal?

Ryan Resch
I got in trouble by the NCAA for buying honey roasted peanut butter.

Jimmy Soni
What?

Ryan Resch
Because I had no idea. So the NCAA was extremely strict pre NIL. And the meals, what classified as a meal, was extremely strict as well. And so we could not provide food under certain conditions to guys because then it would be considered a meal. If they get a meal, it’s an impermissible benefit.

Jimmy Soni
Wow.

Ryan Resch
Oh, it was a whole bureaucracy. I mean, it still is a bureaucracy.

Jimmy Soni
Right.

Ryan Resch
But on a different level. And so, look, according to Baylor compliance, adding honey to peanut butter made it a meal at that time.

Jimmy Soni
Adding honey to peanut butter that a player was going to eat...

Ryan Resch
Yes.

Jimmy Soni
Made what you did impermissible.

Ryan Resch
Yes.

Jimmy Soni
Oh, wow.

Ryan Resch
It’s absurd. Absolutely crazy.

Jimmy Soni
That is bananas.

Ryan Resch
It is. And you talk about, you know, you go back to your previous question about data and logic entering sport, the human component. The bureaucracy of it all is what removes the human component. Whereas the player needs this. Not like, let’s put aside the fact that people just love peanut butter. Like, it’s amazing and I can’t have it in the house. Players need this to recover. They need the sugar, they need the protein, they need the fat. Right? So you are instead focused on this arbitrary definition of impermissible benefit instead of what’s best for the players.

Jimmy Soni
Right. That’s right.

Ryan Resch
Yeah. I think that’s what’s actually removing it.

The Coaches Take the Blame

Jimmy Soni
Oh, okay. You know, during your tenure, they were really starting their climb. So what did you see in that culture? Like, what was it that made Baylor stand out from other comparable programs?

Ryan Resch
I will say one of the things that I understand now that I did not understand then was the coaches always shouldering the blame for the players. Always. And behind closed doors, you know, publicly as well, that one’s more obvious. Like, a lot of coaches do that. But even behind closed doors, a lot of the conversations would center around, okay, if this player is turning the ball over, how do we teach them not to do that? How do we put them in a position not to do that? And I think that’s notable because obviously sport is extremely emotional.

Jimmy Soni
Right.

Ryan Resch
It is very volatile. You’re going to lose three games in a row at some point.

Jimmy Soni
Yeah.

Ryan Resch
And you have to really have this stability in order to ride that. And the easy thing to do there is to get all pissed off and start blaming the players. Say that you need better players, you need more talent, whatever. And maybe that is objectively true. If you are going up against a Duke that has the top five guys in the class, like, whatever, like, you still need to figure out how to beat them. But to see a coaching staff led by Scott Drew, Jerome Tang, a lot of the folks that are still there, shoulder that blame. And then they would always tell them, they would tell me, they would be like, “It’s our fault.”

Jimmy Soni
Oh, wow.

Ryan Resch
And I would say, “I don’t understand this. We’re not the ones turning the ball over.” Because I was so, like, petulant. And then I get it now, like, having gone through everything that I went through at the Suns and everything that’s come after. Like, I understand now that when you ask about the culture of that space, you need to create a teaching culture, like an actual learning culture, where somebody can make a mistake, like turning the ball over or missing a shot, and then know that it’s not going to result in punishment, it’s going to result in a lesson. Maybe that lesson is hard, right? It’s tough love. But there is going to be a lesson involved in it.

Edited Transcript

Jimmy Soni
Welcome to Infinite Loops. My name is Jimmy Soni. I am the editor in chief of Infinite Books and I am guest hosting for Jim O’Shaughnessy. My guest today is Ryan Resch. Ryan spent nearly a decade with the Phoenix Suns, where he started as an intern and left as the assistant general manager and VP of basketball operations, running everything from roster strategy and data science to scouting and health and performance and everything in between. Ryan Resch, welcome to Infinite Loops.

Ryan Resch
Thank you. Thanks for having me.

Jimmy Soni
Of course. So, just so listeners have a bit of context and background, you and I have been friends for a number of years, but when I met you, you were the vice president of basketball operations for the Phoenix Suns, the assistant general manager, and you reported directly to the head of the Phoenix Suns. And you kind of gave me and a number of other people we were with a behind the scenes view of the Suns organization and how it operates. But just so people listening have context: first of all, you were in an NBA front office at, like, a ridiculously young age. You were chief of staff to the head of the organization when the Suns went to the Finals and when they won 64 games.

Ryan Resch
Franchise record.

Jimmy Soni
Yeah. And then you become this kind of, you’re like one of the go to people on sports and data and where they intersect, and now sports data and AI and where they intersect. And right now you are at 1949 Capital Partners and you’re leading the firm’s work on data and AI. So the thing that interests me most, I mean, among other things, is, you know, you’re not six foot four, right? So walk us through kind of like your early life. You were a military brat. But I want to go from, to, before you get to the NBA, let’s figure out how you got to the NBA. So you started out in life and you’re a military brat, you’re moving around a lot. So walk us through: where’d you grow up? How’d you live?

Ryan Resch
Son of two Air Force parents. We lived in seven places before the age of 18 years old.

Jimmy Soni
Wow.

Ryan Resch
Which I always kind of surprise myself when I say that. So, born in New Jersey, lived on effectively every coast. Went to high school in Germany. So I went overseas for high school. It was a military base, on Ramstein Air Base. So still kind of an American experience there, but we did live in a German village. And so it was, you know, a bit of an international time. Came back and moved to Texas to go to Baylor University, where I had family in Texas, in Florida, from my parents’ sides. And Baylor was the first school to accept me. And I’m not the most patient person. And so the fact that they did accept me so quickly did help while I was waiting on other schools. Did enough research into Baylor, their political science program, which was my first, I would say, passion and first love growing up, was political science. Probably from being around the Air Force and the military and learning that side of it. And enrolled in the... would that have been the fall of 2010?

Jimmy Soni
Got it.

Ryan Resch
And I was a campus tour guide my sophomore year. I’m still very good at walking backward and talking. And I had this weird desire to go into sports journalism, which I don’t...

Jimmy Soni
Were you a sports fan growing up?

Ryan Resch
I was a huge NFL fan and I was a big basketball fan.

Jimmy Soni
Okay.

Ryan Resch
But it’s hard when you’re a military kid because you don’t really have a home. So whenever I’m asked, “Oh, where are you from?” I have to give this whole long explanation around it. And when you don’t have, like, a hometown, it’s hard to really pinpoint what you’re a fan of. And I got into basketball when we lived in Florida. So I became a Miami Heat fan at the time, right around when Dwyane Wade was drafted, which was then ironic, that my future boss, James Jones, was on those Miami Heat championship teams. And my dad was a big Pittsburgh Steelers fan growing up. So I grew up as a big Pittsburgh Steelers fan and I loved watching sport. I loved the competition of it, the game of it. And I had no, as you mentioned, I’m not six four. And so I had no... I’m deeply... I have no coordination, no hand...

Jimmy Soni
To be clear, Muggsy Bogues, like, broke the mold, right? Like, when I was growing up, because I was short and I loved basketball, so in the brief period in which I held these, you know, dashed dreams of becoming a basketball player, I would just turn to Muggsy Bogues. Like, Muggsy made it work.

Ryan Resch
There you go. That’s all you need. You just need determination and grit and hope that your jump shot... And I, for a very short period, decided to double major in journalism, which I quit. And then decided one day, it’s like, I am just going to cold email Scott Drew, who is the head coach of Baylor men’s basketball still to this day. And testament to him that he responded right away. So right after my summer, after my sophomore year, I sent a cold email to Scott, said, “I respect your program. I admire what you’re building. If there’s ever anything I can do to help, let me know.” And he replied that same day, if I’m remembering correctly. And he said, “Come be a student manager.”

Jimmy Soni
Wow.

Ryan Resch
And I said yes. I had no idea what it meant.

Jimmy Soni
Right.

Ryan Resch
And I show up maybe two or three days later, and I am an equipment manager, folding towels and doing laundry for Baylor men’s basketball.

Jimmy Soni
Wow.

Ryan Resch
And it’s very... they just throw you right in. And so you’re in the locker room, like, getting everything ready for the guys before practice, after practice, for games. You’re on the court helping, you know, rebound and pass balls and those kinds of things. I was so bad at passing a basketball. When I threw, it was so bad that Scott Drew called me into his office. He probably remembers this. And he taught me how to throw a chest pass with spin on it. Like, how embarrassing is that?

Jimmy Soni
So just so I have this clear. So you were, you’re there and you’re passing basketballs. Did the players say something? Did they know something? Or he just installed...

Ryan Resch
How bad... Coach Drew. Okay, this is Coach Drew. This is why he’s a national championship coach. Because he sees these things and he fixes them.

Jimmy Soni
Right. Even in his student manager.

Ryan Resch
Exactly. Exactly. And that, I think it says a lot about him, but it also says, I guess it’s like an early lesson...

Jimmy Soni
Yeah.

Ryan Resch
Like the nature of detail.

Jimmy Soni
Right.

Ryan Resch
Sport and winning, these things. Because if you throw a knuckleball, if you throw a ball without any spin, you can break someone’s finger.

Jimmy Soni
Right.

Ryan Resch
And jam their finger. Right? God forbid it’s on a shooting hand.

Jimmy Soni
Yeah. Wait, is that true? Sorry, is that true in... So you’re saying in basket... Knuckleballs are a baseball term, right?

Ryan Resch
But it is, yeah. So a ball with no spin.

Jimmy Soni
Yeah.

Ryan Resch
So I wasn’t putting any spin on my chest pass. I was just literally chucking the ball. I was accurate. Like, accuracy was not the issue. This is actually getting spin and rotation on the ball, which the best shooters can tell you about, because you have to put backspin on the ball in order to actually guide it to the target that you’re launching. Don’t ask me about shooting. I’m not...

Jimmy Soni
Not the expert. Okay, so just out of curiosity, if we take a step back in the story... I mean, I want to go a bunch of different places, but let’s talk about living in seven different places before the age of 18. Right. Because that is not an experience that I had. I’m assuming actually most listeners are pretty geographically... As a kid, you know, your parents do tend to want to stay in one place by design. Your parents can’t, right? So what was it like being the new kid all the time? Right. Like, was that... I mean, I’m sure this shaped your life. I’m asking, how did it shape your life?

Ryan Resch
Yeah. I think the most obvious is what I’ve already mentioned, where you don’t have a sense of home in the traditional way that people think about that. Where I’m just now learning, so we still have a house in Phoenix. Love Phoenix. Very actually attached to that house. And that is the first kind of time that I’ve felt that I can call a place home.

Jimmy Soni
Yeah.

Ryan Resch
And that has been a very kind of transformative experience for me. The other aspects of it, you become very adaptable and you become very malleable. You could enter any space and be comfortable. I’m also an only child, so I have no brothers or sisters. This was just me and my parents running around the country and then over to Germany. And you’re able to talk to people and you’re able to introduce yourself, maybe not so comfortably when you’re 12.

Jimmy Soni
Yeah.

Ryan Resch
But you know, you start, you get reps at it.

Jimmy Soni
Right.

Ryan Resch
I think probably the more important thing is I was forced into situations where I had to get reps at introducing myself and telling people and showing people who I am, as I’m also trying to figure that out throughout the rest of my life.

Jimmy Soni
Right.

Ryan Resch
Or growing up, rather. And it does leave you with kind of a few things. One of them is I’m always moving. Like, not moving homes necessarily now, but I am always constantly in a new place. So it’s very hard for me to stay still.

Jimmy Soni
Yeah.

Ryan Resch
This is why sports was so good for me. Because you’re on two week east coast road trips and you’re playing in Toronto and then tomorrow you have a game in Philly and you’re just kind of moving around a lot. And then it also leaves you just with this sense of confidence, if you’re kind of maturing into that space, where you can just enter spaces.

Jimmy Soni
Right.

Ryan Resch
And be okay.

Jimmy Soni
Right.

Ryan Resch
In a way that maybe somebody who hasn’t had that experience just needs more reps at it.

Jimmy Soni
Yeah. So this ties to my next question, which connects to the time with Baylor and with Coach Drew. You know, there are a lot of people who watch sports as casual fans or as kids kind of admiring athletes from afar, and there’s a certain impenetrability to the world of sports. You think, well, if I don’t have that level of talent, there’s no way for me to get involved in sports. Right. And so for you, you do this extraordinary thing, which is, like, as a sophomore, you take a gig that puts you at the very, very bottom rung of the organization. When you sent that email, like, if you can think back that far, that’s a pretty extraordinary... Like, I’ll give you an example. I’m suddenly sitting here so jealous that you did that. Because I went to Duke and basketball’s a religion.

Ryan Resch
They have a whole manager program.

Jimmy Soni
And I would have been like, I would have been applying if I had known that was even a possibility. Right. But I never knew it was a possibility. And so my question is, how did you... Was it in that moment, was it a desire to be closer to sports, or was it just kind of on a whim? Like, what motivates you to do that? Because it really does shape the rest of your trajectory.

Ryan Resch
It did. I think it’s all of those things that you’re saying. The idea came to me because my boss, actually, at the campus tour guide center...

Jimmy Soni
Yeah.

Ryan Resch
She had a Baylor basketball poster on her wall in her office, and we would always talk about the games and Baylor basketball. It’s an excellent program. We’re still excellent. And this was kind of the first period of, like, Scott Drew’s excellence was those, like, 2010 to 2014, really.

Jimmy Soni
Right.

Ryan Resch
When I was there.

Jimmy Soni
Yeah.

Ryan Resch
Those years. And so we...

Jimmy Soni
That was a nice subtle wave. And, like, you know, I might have had something to do...

Ryan Resch
Well, they won the National...

Jimmy Soni
Once I fixed those passes I was passing back to the players, everything got better.

Ryan Resch
And she, we would just talk about it so much, and I think I maybe just said offhand, like, “I wonder how you even begin to get involved in that.”

Jimmy Soni
Yeah.

Ryan Resch
And she was like, “Just email Scott Drew,” or something like that.

Jimmy Soni
Right.

Ryan Resch
And this was, it’s so commonplace now. If you want to reach someone, it’s their company name, their first initial, last name, or their first name@company name.com, or whatever it is. I think that was still a bit of a foreign concept back in, whatever it was, 2012.

Jimmy Soni
Yeah.

Ryan Resch
And so I was probably very nervous to send it.

Jimmy Soni
Yeah.

Ryan Resch
But it also, like you said, it sparked all of this. And it’s why I have this rule that if someone reaches out to me...

Jimmy Soni
Yeah.

Ryan Resch
And wants advice on how to get into sport, then I will at least talk to them one time so that we can go through this process of, hey, you’re in college, you want to figure out how to do this. You need to find the director of basketball operations for your team, send them an email saying that you want to be a student manager and ask if they have that program. And the reason I do that is because I didn’t have that guidance. I did it. And it’s cool now because there’s actually a few people around the league that were undergrads that reached out, that became managers at Tennessee and other schools that are now in the NBA.

Jimmy Soni
Wow.

Ryan Resch
Because of it. But I think I’m a bit of a venturer now, is how I can describe it. And in order to do that well, you just have to have the agency to send the email. Right? Just send the email. If they don’t respond, everything’s okay.

Jimmy Soni
Right.

Ryan Resch
Find the next thing.

Jimmy Soni
Right.

Ryan Resch
And then keep going.

Jimmy Soni
That’s great. Okay, so you did mention this, but Baylor was a serious, and it’s still a serious program. I mean, you went to the, I think it was a 2021 championship, right?

Ryan Resch
Yes, it was Covid. It was the Covid tournament. Because I did not get to go, unfortunately.

Jimmy Soni
Oh, okay. You know, during your tenure, they were really starting their climb. So what did you see in that culture? Like, what was it that made Baylor stand out from other comparable programs?

Ryan Resch
I will say one of the things that I understand now that I did not understand then was the coaches always shouldering the blame for the players. Always. And behind closed doors, you know, publicly as well, that one’s more obvious. Like, a lot of coaches do that. But even behind closed doors, a lot of the conversations would center around, okay, if this player is turning the ball over, how do we teach them not to do that? How do we put them in a position not to do that? And I think that’s notable because obviously sport is extremely emotional.

Jimmy Soni
Right.

Ryan Resch
It is very volatile. You’re going to lose three games in a row at some point.

Jimmy Soni
Yeah.

Ryan Resch
And you have to really have this stability in order to ride that. And the easy thing to do there is to get all pissed off and start blaming the players. Say that you need better players, you need more talent, whatever. And maybe that is objectively true. If you are going up against a Duke that has the top five guys in the class, like, whatever, like, you still need to figure out how to beat them. But to see a coaching staff led by Scott Drew, Jerome Tang, a lot of the folks that are still there, shoulder that blame. And then they would always tell them, they would tell me, they would be like, “It’s our fault.”

Jimmy Soni
Oh, wow.

Ryan Resch
And I would say, “I don’t understand this. We’re not the ones turning the ball over.” Because I was so, like, petulant. And then I get it now, like, having gone through everything that I went through at the Suns and everything that’s come after. Like, I understand now that when you ask about the culture of that space, you need to create a teaching culture, like an actual learning culture, where somebody can make a mistake, like turning the ball over or missing a shot, and then know that it’s not going to result in punishment, it’s going to result in a lesson. Maybe that lesson is hard, right? It’s tough love. But there is going to be a lesson involved in it.

Jimmy Soni
Can I ask you this? This question is a bit more just personal perspective. But, you know, when you’re a college student, sometimes you have a too healthy sense of your own importance, right? And I’ve got to believe, like, you’re a very smart guy and you’re studying political science, you know, and you’re at Baylor and you have a good head about you, and now you are folding towels, right? Like, how did you put your ego to the side? And was it a rude awakening? Like, you get in, you think student manager is going to do all kinds of interesting things, and now you’re folding towels and you’re learning how to pass better. What was that like? Like, is there a part of this that was just, you already knew what you were getting into, or was it now the proximity of the game was the payoff? Like, it was just you wanted to be a part of this and you figured this was the way to do it.

Ryan Resch
I did not know what I was getting myself into. It’s funny that you asked that, because one of my fondest memories is on Sundays at Baylor, people are at church and Ryan was cleaning the gym. I was cleaning the practice gym. And I loved it because you had to get this big pole out, put towels on it, and, like, drag this pole all the way across the court in order to clean it. And it was just a very cathartic, like, meditative. Meditative, that’s exactly what it was. You would turn on a podcast or music or something, and you would just do it, and then you would clean the gym. And I don’t remember having kind of an adverse reaction to any of it, although I probably did at some point, years, when I was head manager my senior year. Right? Did I act probably some way where it was like, you know, now this is beneath me, the young manager can do it? Probably.

Jimmy Soni
Yeah.

Ryan Resch
But what you learn in doing it genuinely, when you are the person putting out the loops that have all of the jerseys and the shorts and the socks and everything on the player’s chair, it’s behind a locked door, so if you’re not doing it, player can’t get dressed, player can’t practice. And so you’re able to actually experience, like, the operational chain of how we go from this nice idea, all right, let’s run a basketball team, to, no, these are all of the dirty steps and the details that it takes to get it done.

Jimmy Soni
Yeah.

Ryan Resch
And I think that was a huge payoff for me, especially my last year at the Suns when I did run the daily operations of the franchise.

Jimmy Soni
Yeah.

Ryan Resch
Where it was like, I knew what our equipment manager was going through.

Jimmy Soni
Okay.

Ryan Resch
Where he’s dragging these trunks around constantly, him and his assistant. And how do we lighten that load for those people who are extremely important to get this done.

Jimmy Soni
So at some point during your tenure at Baylor, you become the guy who has the data, who has the numbers. So what’s chapter two? In excruciating detail, describe, like, you know, spare no story there. How do you go from towels to analytics and spreadsheets? And you’re helping the coach think differently about the game. When does that transition start to happen?

Ryan Resch
So I was head manager my senior year, and political science was my passion. Basketball was my hobby. Like, that was kind of the differentiation that I put there. That’s really the only two things I had, outside of friend group, obviously. But we would be at the gym till 3am scouting the next opponent, and, like, at crazy hours.

Jimmy Soni
Wow.

Ryan Resch
Still, even in the NBA, crazy hours. And I graduated, I went to go get a PhD in political science at the University of Missouri. There was a professor there that I wanted to study under for American Political Development. And around, was it my sophomore, it was either my sophomore or my junior year of undergrad, I was introduced to data science and statistics through econometrics and political science. And when I kind of dug deeper into that world, I realized, oh, my brain is actually extremely logical. And, like, coding came naturally to me. Data came naturally to me. I still love theory. I still love philosophy, liberal arts, all of those things, for sure. How do we blend these two things? I go to Mizzou for a year and we’re working on these papers and this research, and I just have this feeling that’s like, this is just not it for me. This is not right for me. Different than when I, you know, quit campus tour guide to go to basketball. This was like, no, this is fundamentally not the place for me.

Jimmy Soni
Yeah.

Ryan Resch
And I think what I ultimately settled on, which is kind of a principle that I now carry throughout life, is I don’t want to study problems. I want to actually solve the problem. Now that requires you to study them in order to solve them. Yeah, but we’re not going to actually solve it if we are just kind of writing papers and going about our day. I want to actually do. I want to do all that, and then I want to do it to see if we’re right or not about it. And I decided that I was going to leave the program, so I quit. And I did not know what I was going to do. I had absolutely no idea. It is probably the scariest period of my life because I just had no concept of what else I could be doing. Right.

Jimmy Soni
Yeah.

Ryan Resch
And I happened to go to the Big 12 tournament, which is the conference that Baylor, I think they’re still in.

Jimmy Soni
Yeah.

Ryan Resch
I can’t keep up with the conf...

Jimmy Soni
I know. Neither can I. It seems to change on a dime.

Ryan Resch
It’s, yeah, wild. And I went to the Big 12 tournament, spent a few days with the team again and realized, okay, I think I just missed the team environment. So I called Scott Drew again, and he answered again. And I said, “I don’t know what I’m going to do, but do you have any advice for me?” And he was like, “Well, I just got done talking to Tom Izzo at Michigan State,” who’s a good friend of his.

Jimmy Soni
Yeah.

Ryan Resch
And legendary coach.

Jimmy Soni
Legendary. Yeah.

Ryan Resch
“And he just hired someone to do data science and statistics for them. Can you come do it for me?” I said, “Sure.”

Jimmy Soni
That’s amazing.

Ryan Resch
And that was amazing. Probably a month leading up to... Well, first we had to get me into a grad program because this was very late. It was like April at this time. Thankfully, that all worked out.

Jimmy Soni
And why did you need a new grad program? Because he couldn’t hire you unless you were a student?

Ryan Resch
I was going to be a grad assistant. Yeah. I was going back as a grad assistant.

Jimmy Soni
Got it.

Ryan Resch
So there’s, like, the student manager program for undergrads. There are grad assistants. Typically grad assistants are going to follow the coaching route, although more and more commonly it’s video analytics and whatnot as part of it. And I guess GM now for these colleges. And so I go back to Baylor in, whatever was that, 2015. 2015, spring of 2015. Yeah. And Coach Drew’s like, “I want lineup data.” Okay. And lineup data did not exist at this time. Like, there was no easy accessible, like, public form of lineup data that you could also trust. You know, it was a whole kind of amorphous concept still.

Jimmy Soni
And just for context, like, I remember, I think Moneyball came out in 2003. The movie is like 2011, something like that. So we’re not in the... we’re still, we’re post Moneyball, but we are pre, like, the digitization of everything, sports especially.

Ryan Resch
Probably at that level. And it also started in baseball. So Moneyball is the baseball book, obviously. And then it kind of slowly made its way across football and soccer and, you know, obviously lacrosse and those other ones. And then basketball was also really starting to take off. Daryl Morey popularizes, you know, threes and layups only with Moreyball. And that’s kind of the launching of the analytics movement in the NBA at, like, a popular level.

Jimmy Soni
Yeah.

Ryan Resch
And Moneyball kind of joins along those lines. So the mid-2010s was, I would say, really where teams and people took it more seriously in basketball.

Jimmy Soni
Yeah.

Ryan Resch
And so there was just no lineup data for college basketball that we could rely on. And to this day, I don’t know how I had this idea. But in basketball, all sports, you have the play by play.

Jimmy Soni
Yep.

Ryan Resch
That says, okay, you know, your point guard is subbing in, your shooting guard is subbing out. Point guard made a two point shot, assisted by your small forward. Along those lines, in text.

Jimmy Soni
Yes.

Ryan Resch
Pre AI.

Jimmy Soni
Yeah, pre AI.

Ryan Resch
Early days of machine learning and AlexNet and those things. And I scraped those play by plays.

Jimmy Soni
Wow.

Ryan Resch
And from the text, I turned it into a box score and so we could build the... And I’ll never forget this. This all hinged on two things being true. The sub ins, sub outs had to be on the play by play.

Jimmy Soni
Yeah.

Ryan Resch
Else this wouldn’t work.

Jimmy Soni
Right.

Ryan Resch
And the starters, there had to be a connotation of who started the game.

Jimmy Soni
Huh.

Ryan Resch
So typically that would be the first five players listed. Not always, but thank God there was an asterisk next to the starters.

Jimmy Soni
Just so I have this right, so I’m understanding this correctly. There was no box score data for Baylor or maybe even men’s college basketball at circa whatever year this is, 2015. Nobody is tabulating these and putting them on ESPN. Wow.

Ryan Resch
For individuals, yes. Yeah. Like, you can go to College Basketball Reference, amazing website. They have the individual box scores and whatnot because that comes from the scorer’s table, the statistics from the game. This was, no, okay, now we want to know five man combinations. So for those who don’t know, a lineup would be your point guard, shooting guard, small forward, power forward, center.

Jimmy Soni
Yeah.

Ryan Resch
Five man combinations. How are they performing together?

Jimmy Soni
Got it.

Ryan Resch
I’m not going to say it’s like a brand new concept. Right. Getting that data at scale so we can have it for Baylor and our opponents.

Jimmy Soni
Yeah.

Ryan Resch
Was a novel problem to solve.

Jimmy Soni
Okay. So you scrape the data and you build something to scrape the data, and then what happens after that?

Ryan Resch
We converted the text into the box score. Yeah. So point guard made two point shot. That becomes two points, two point field goal attempt, two point field goal make. So each of the little traits that you can, the variables that would make up that action, you can now register and log it in your box score. And then you sum it all up and you aggregate by lineup. And then, you know, I think, and this is what AI I think is teaching so many of us, is once you have the data extracted and structured, you can do so many different cuts of it. And so now we have five man, four man, three man, two man. Like, what about these different combinations of guys? Like, it just kind of exploded in that way. And coach was happy with it and it started just kind of influencing rotations and substitution patterns and those kinds of things.

Jimmy Soni
So, yeah, this is where I want to go a bit deeper. Because, I mean, famously, the scenes in the movie in Moneyball, but then also as described in the book, is there’s a graft versus host problem. Right? Like, you have a person who’s very smart with this kind of stuff and there’s an allergic reaction from people who believe it’s going to sully the sanctity of sport. Right? You’re going to add an impurity, which is like logic and reason, in something that ought to be subject to competition and fate and individual effort and all these other kind of more, call it more ethereal, things. Right? And into that you’re introducing, like, logic and regression analyses and actually looking at data. Did you face any of that when you were starting to pull these things together? Like, were you sheepish? Was the coach resistant? Was there any part of the organization that was like, “Ryan, we love this stuff, but we know how to play the game and you don’t. You couldn’t even throw a pass until he coached you to throw the pass better.”

Ryan Resch
Maybe that’s why it worked. Because this coach knew that I wasn’t trying to front as though I knew how to do these things. I definitely have run into that resistance. Yes. But I’ve also been extremely fortunate that the principals that I have worked for, so Scott Drew, James Jones, these are people who are very rational thinkers to begin with.

Jimmy Soni
Yeah.

Ryan Resch
And so they want this data, they want this information. And so that helps, number one. But what it does teach you is this incredible lesson of, like, and I think that this is important for data folks and maybe more, like, rationally minded folks, is there is a difference between being effective and being right. And this is something that I had to learn at the Suns. And it came from kind of exactly what you’re describing, which is if sport is this constrained, bounded game that we have all of the rules for, we know exactly how it’s structured, there is a very clear scoring and reward system, we can apply game theory, we can optimize it for strategic and tactical choice. If that’s true, then why are we not doing it, right?

Jimmy Soni
Right.

Ryan Resch
And the answer in my mind always came back to what I called the communication problem, which is we are fundamentally lacking the ability to communicate why these insights matter to help you make better coaching decisions, or you make better playing decisions, or you make better executive level decisions like who to put on the roster and who to take off.

Jimmy Soni
Right.

Ryan Resch
And I think there are a host of ways to solve that. The language that you choose, the tone in which you speak to people, like the more maybe ephemeral concepts that are qualitative, maybe more quant driven folks don’t naturally move toward. But I think also, and this is where I hope it goes in sport, is team building is a beautiful art and a beautiful science. Like, there’s really a blending of it to do it well. It’s the cultural aspects that you asked about earlier, as well as, if you think about kind of a two by two grid when you’re making team building decisions, whether it’s a roster or your staff, you know, for a job somewhere else, you have to focus on the person and you have to focus on the professional. So instead of person, for sports it’d be a player. So player and professional. You have to focus on the league’s perception, so kind of the in a vacuum perception.

Jimmy Soni
Yeah.

Ryan Resch
And you have to focus on, for my team, what is that going to be? So this player X might be an excellent three point shooter in the league standards. Absolutely excellent. But they can only get their threes off of very specific actions. Those actions are not good for our team because we don’t have the person to create those actions. And so I objectively believe that you are an excellent three point shooter, but you’re not going to help our team right now. You have to kind of hold this balance, and that’s a very human thing, is to hold these conflicting and competing views in your mind. And I do think that where data helps is quantifying and telling that story of player, professional, person, professional. How are they viewed kind of in a vacuum within their entire cohort, and then how are they viewed for our team specifically under our conditions? And if we can get the data, with the help of AI, if we can get the data more down that more human story...

Jimmy Soni
Yeah.

Ryan Resch
Then I think it becomes more easy to apply it. And once it becomes easier to apply, it’s more helpful.

Jimmy Soni
Right.

Ryan Resch
And once it’s helpful, it’s valued.

Jimmy Soni
What’s an example from your days at Baylor where, because you’re really creating this stuff from whole cloth, right, and there’s not anybody feeding you this, you don’t have APIs you’re plugging into, you’re doing this largely on your own, I assume. What’s an example of something that shifted because of something you found? It can be small, it can be big. But, like, what’s an example of when you had an insight and you said, this is, I’ve generated new knowledge here, and then something shifted in the organization as a result?

Ryan Resch
At Baylor specifically?

Jimmy Soni
Yeah.

Ryan Resch
I think one of them, we had a forward who, absolutely excellent scorer. Yeah, absolutely excellent. Six eight, six nine, you know, very smooth scoring the ball, and he didn’t get a ton of minutes. And part of that was because, like, he wasn’t the hardest worker, did not kind of present as, you know, like, a cultural anchor of the team, those kinds of things. And I’m not saying that is a deserved reputation or not, but when you looked at the numbers and you said, okay, when this player is on the floor, like, per minute, the impact that this guy is having is actually extremely high. Okay, how do we fix these things that are going wrong so that maybe he shows up on time? Or how do we put a better environment around him where he’s playing with certain guys who are going to get the most out of him, because his per minute efficiency is so high? Let’s not turn a blind eye, but let’s focus on fixing those things that we really dislike, that we want to vent about, so that we can unlock this for the team.

Jimmy Soni
Got it.

Ryan Resch
So that we can unlock this scoring prowess for the team. Because it’s really easy, again, sports is extremely emotional, it’s really easy to be focused on, we just lost, you were late to shoot around.

Jimmy Soni
Right.

Ryan Resch
You’re one of the reasons that we lost. I’m not saying that’s not true.

Jimmy Soni
Right.

Ryan Resch
But the payoff of unlocking that...

Jimmy Soni
Yeah.

Ryan Resch
We can now see what that looks like.

Jimmy Soni
Got it.

Ryan Resch
And that’s where, you know, we talk, I think that data is a mechanism to create focus. Yeah. That helps you focus on, if we can fix this set of issues, we unlock this.

Jimmy Soni
That’s really interesting. Was this common in college basketball at the time? Like, I know you said Tom Izzo is what turned Scott Drew onto it. Had it become commonplace for coaches to hire somebody on their team to do this kind of data science?

Ryan Resch
I wouldn’t say it was common. I think Coach Drew was definitely ahead of his time. Tom Izzo, ahead of his time. Ken Pomeroy, who’s still a big name in college basketball data, had been around for a few years and he was kind of the one that was known. But this was pre NIL. So this was pre all of the money.

Jimmy Soni
Yeah.

Ryan Resch
I’m like, you want to talk about pre NIL? I got in trouble by the NCAA for buying honey roasted peanut butter.

Jimmy Soni
What?

Ryan Resch
Because I had no idea. So the NCAA was extremely strict pre NIL. And the meals, what classified as a meal, was extremely strict as well. And so we could not provide food under certain conditions to guys because then it would be considered a meal. If they get a meal, it’s an impermissible benefit.

Jimmy Soni
Wow.

Ryan Resch
Oh, it was a whole bureaucracy. I mean, it still is a bureaucracy.

Jimmy Soni
Right.

Ryan Resch
But on a different level. And so, look, according to Baylor compliance, adding honey to peanut butter made it a meal at that time.

Jimmy Soni
Adding honey to peanut butter that a player was going to eat...

Ryan Resch
Yes.

Jimmy Soni
Made what you did impermissible.

Ryan Resch
Yes.

Jimmy Soni
Oh, wow.

Ryan Resch
It’s absurd. Absolutely crazy.

Jimmy Soni
That is bananas.

Ryan Resch
It is. And you talk about, you know, you go back to your previous question about data and logic entering sport, the human component. The bureaucracy of it all is what removes the human component. Whereas the player needs this. Not like, let’s put aside the fact that people just love peanut butter. Like, it’s amazing and I can’t have it in the house. Players need this to recover. They need the sugar, they need the protein, they need the fat. Right? So you are instead focused on this arbitrary definition of impermissible benefit instead of what’s best for the players.

Jimmy Soni
Right. That’s right.

Ryan Resch
Yeah. I think that’s what’s actually removing it.

Jimmy Soni
Right. You know, it’s a bit of a detour, but I am curious, because there are very strong opinions on what the NIL changes have done to college sports. And I’m not well versed enough, so if you could give a little bit of a brief on what has changed. But my own sense as a fan from afar is that today’s, particularly college basketball, because that’s the one I follow, but today’s collegiate athletic environment, it feels like the Wild West. Like, there was just a lawsuit in Colorado that allowed an additional year of eligibility for a bunch of NCAA players. And now all of a sudden men’s college basketball for the year ahead is, it’s scrambled. You don’t know what’s going to happen. You don’t know who’s going to come back, how they can come back, how long they can stay. If you get an appeals court to say one thing, it might change the decision. This could rise to the level of the Supreme Court. What do you make, as everybody who’s been there, what do you make of contemporary college athletics?

Ryan Resch
I find it very hard to keep up with, for all of the reasons that you’re describing, which is there are institutions involved now that we would have never considered. Like, at our time, we’re not thinking about, okay, what is the Supreme Court going to decide on this case? And will that affect whether my player is eligible or not?

Jimmy Soni
Right.

Ryan Resch
The rules there were very clear and I think we appreciated the time. I think that the positive side of it is that these players who have this unbelievable gift and these incredible talents, both skill wise, physically, athletically, all of it, they are now receiving compensation for these things. I think that is, like, an economic benefit and a good thing that is occurring. Where it has gone poorly, I think most importantly where it’s gone poorly, is the continuity of teams. And transfers were a problem pre NIL.

Jimmy Soni
Right.

Ryan Resch
So NIL is name, image, likeness, where you are now paid for your name, image, likeness. And there’s a host of rules around how you can receive your money. But it has led to NIL plus what they call the transfer portal in college, where players can now basically leave teams and schools whenever they want to, put your name into the transfer portal, sometimes in an effort to maximize your NIL.

Jimmy Soni
Yeah.

Ryan Resch
It has led to rapid turnover with teams and makes the coaches’ and the now college general managers’ jobs harder. That job did not exist when I was in college.

Jimmy Soni
There was no college GM?

Ryan Resch
There was no college GM when I was there. We were just scraping play by play.

Jimmy Soni
Exactly. Doing it in the Stone Age.

Ryan Resch
Exactly, exactly. And the turnover of these teams is just so high now, where players are leaving, going to the transfer portal, maybe trying to maximize their cash, whatever they deem the most important. And you lose, like, Duke does lose this period of where you guys had Christian Laettner for years, or, yeah, Jahlil Okafor and those guys only stay, Tyus Jones only stayed for one season. But you still had those faces on the team that you recognized year over year. Baylor was the exact same way. You don’t really have a lot of that anymore. And I think that loses, again, back to the human side of sport, that loses, when everybody’s kind of in the foxhole together playing this zero sum game every night, it’s win or lose. Yeah. That is where those bonds are really formed. Where I can still call the coaching staff at Baylor, or the grad assistants at Baylor, or some of the players at Baylor, and we’ll talk about, you know, what the 20, whatever it was, 16 Sweet 16 at Madison Square Garden, where South Carolina completely dismantled us. Like, we still, you know, talk about that. Right? And you just don’t have those memories, that experience or this camaraderie.

Jimmy Soni
I do have one question on this one. It’s interesting. I think about this just as a casual fan, but also kind of the challenge here is, on the one hand, there were always going to be people who were going to be one and dones, right? Who were going to come in, light college basketball on fire, do their year and then go off and play in the NBA. Even before that, you could skip college altogether and go straight to the NBA the way Kobe and others have done. At the same time, you now have money that’s available to you to be paid to stay in college. Right? So isn’t the argument against what you just said, well, yes, it’s true, people can job hop effectively, or college hop, right, and go from one school to another using a transfer portal to maximize their winnings and earnings. But on the other hand, they’re actually getting paid while they’re in school and thus can stay in school longer, right? And then it’s on the program and on the coach and on the university to make that both worth their while financially and make sure that they feel like it’s a place where they want to call home for X number of years. Right? So isn’t there a little bit of, this actually took some of the, it created the safety valve for the pressure to leave for the league, like, too early or skip school or, like, to be a one and done, because now you could be a two or three and done, right? Or a four and done and still get paid for your time. I’m not well versed enough, but does that argument have any weight?

Ryan Resch
I want to say yes, more so in football. Like, I don’t know exactly what that would look like, but anecdotally it feels like I’ve seen more of those stories of someone choosing to stay in college football. Yeah. And NIL money is larger in college football than it is college basketball. Unless you are at a Duke.

Jimmy Soni
Right.

Ryan Resch
Or a Kentucky. So I think it’s more true in football. I could be wrong on the basketball side of things. I don’t know if it has yet reached the NBA side where, yeah, like, the contracts in the NBA are fundamentally different than the NFL, than the Major League Baseball. Each of these leagues has a very different economic structure. Yeah, the NBA’s is extremely player friendly.

Jimmy Soni
Okay.

Ryan Resch
Very, very strong players association, especially back in the 2010s when they were negotiating those really core CBAs. And the players will get, if you’re drafted in the first round, two years guaranteed, two year team option. But you’ll usually look at all four years guaranteed at some point, and then from there, if you’re a good player, you’re making 20 plus million dollars a year now. So the payoff for college basketball may not be there yet. Or I do think your argument has a lot of merit, is that the onus is now on program building. Right? You need to build a program.

Jimmy Soni
Right.

Ryan Resch
Which is where the Baylors and the Dukes and these other schools who have done it are benefiting, with, like, these brand name institutions who have built actual programs. There’s now a value on that, there’s a premium on that.

Jimmy Soni
Right.

Ryan Resch
At some point this will all be, as things always are, regulated to some degree. There will be more rules in place about how much you can pay under what conditions. Like, some kind of salary cap system. Yeah. So I do think that there is a premium that’s now placed on building an actual program. So if you do have one of these brands like a Baylor or a Duke, there is a lot of value there. Once we have some form of a salary cap system, where I think that’ll happen at some point in the future, marry those constraints with what you’ve described of that program culture building, now you’ve got a more professional sport environment there. How do you build an Oklahoma City Thunder in college basketball? How do you build a Pittsburgh Steelers in college basketball? You kind of need both the economic constraints and the recognition of how valuable those programs are.

Jimmy Soni
Right. Ironically, these deals could lead to people, like, completing their degrees, right? The great irony of this might be that so then every worth the student athlete, right? It really could. Because if you think about it, at some point, all other things being equal, if there is a salary cap system and you are constrained on the economic side, then you would just have, you know, all schools would probably reach, like, theoretical limit of whatever those caps are, then program design and, call it, like, student retention matter a great deal. And if you are a coach that has a history of winning and producing NBA level talent and a culture that people actually want to be a part of, and you are at a school where people want to stay to finish their degrees, you as a player, you’d have serious, if you’re not a superstar, if you’re not a one and done, right, you’d have a serious reason to stick around for four years and earn a degree.

Ryan Resch
Incentive alignment. Yeah, that’s right.

Jimmy Soni
Yeah, I like that. And I don’t know, I’m speaking about it in a total vacuum. I don’t know how these decisions actually happen, but it seems to me to be one of the kind of, I know that there’s been a lot of coverage on it and a lot of back and forth on it, sure, but actually I have found this to be one of the most interesting things to be happening in college sports. That is an economics question and a psychology question and a culture question. Not even a, what does the law say and doesn’t say. Because right now what’s interesting is the law isn’t clear. Congress is being petitioned 20 different ways on it. There are already cases underway. So it is interesting to me to think about what is a player who’s good but not good enough to leave and, like, kind of likes where they’re at, but sees that the grass might be greener on the other side. Right? Like, I wonder how people are thinking about this.

Ryan Resch
I do think that you’re probably onto something there, where it is, incentive alignment will happen at some point, it feels like, in this space. And it probably does benefit everybody in the end. I think right now it’s already so hard to recruit in college sports to begin with.

Jimmy Soni
Yeah.

Ryan Resch
That it has made the jobs of these head coaches infinitely harder. Yeah. Only because there aren’t the economic constraints that are specific right now. And because it’s made it so hard, that’s probably where some of the negative, like, publicity and whatnot comes in. It is interesting, though, to think, like, we’re sitting here today and we don’t bat an eye on college basketball players or football players making millions of dollars.

Jimmy Soni
Right.

Ryan Resch
And that was, I mean, unheard of.

Jimmy Soni
Just a few years...

Ryan Resch
Absolutely unheard of. Recruiting visits had very strict budgets and, yeah, you could only do certain things.

Jimmy Soni
Yeah.

Ryan Resch
It is, it’s wild.

Jimmy Soni
It’s wild. It’s also, I remember when I was a freshman at Duke, when by the time I got to my junior year, senior year, they did a deal with Apple where all the freshmen at Duke for a given year got iPods. And I remember being so mad that I had missed the free iPod window. If I was a college athlete who finished up at Duke after these deals went into effect, so the deals weren’t around when I was around, yeah, I’d be livid. I would be livid because the size is actually significant, life changing amounts for these players.

Ryan Resch
It really is. And that’s why the transfer portal is so active.

Jimmy Soni
Right.

Ryan Resch
It really is.

Jimmy Soni
Right. So now we go, you’re at Baylor and you’re a grad assistant and you are furnishing analytics and insights for the team. How long are you at Baylor? And then tell us how the story gets from there to the Phoenix Suns.

Ryan Resch
I would be at Baylor for two years in chapter two, post PhD. The summer after the first year, I got an internship with the Phoenix Suns analytics department on the basketball operations side. So every NBA team, every professional sports team, more or less, is split between sport operation and business operation. So business operation would be tickets, sponsorship, sales, media, kind of everything you’d think under the business banner. And then the sport operation is building and managing and operating the team. Yeah. I was sent by a classmate this analytics internship in Phoenix. I did not have a plan about what I was going to do, and I told myself, probably the only path forward is in the NBA, because, again, it’s not a huge thing in college basketball. Coach Drew would eventually, like, consider bringing on this position, but he would also push me out and say, “You have to go to the NBA,” when that opportunity presented itself, which I’m very grateful for, because it would have been easy to stay.

Jimmy Soni
Yeah.

Ryan Resch
And I got this internship.

Jimmy Soni
So how did that... Well, walk us through it. How, you know, sometimes these internships don’t just happen. Did you just apply? You applied, you interviewed?

Ryan Resch
I applied.

Jimmy Soni
That was it.

Ryan Resch
Applied and interviewed. And I think, you know, again, it’s funny, it comes back to the communication side of it, I think.

Jimmy Soni
Yeah.

Ryan Resch
Where when I was interviewing with the individual who would hire me, the then director of analytics of the Suns, there was a question around, so the Phoenix Suns were really bad.

Jimmy Soni
Yeah.

Ryan Resch
At this time. So one of the worst teams in the league. There was a playoff drought, and the league was just starting to play faster, shoot more threes, have more space, and the Suns were not doing these things. And the Suns were still playing two centers at the time. And I was asked, like, “What would you look at to show the coaching staff not to play two centers?” Very interesting question.

Jimmy Soni
That’s very interesting.

Ryan Resch
Very specific question. Yeah. And I’m sitting there just thinking about it, and I said, “Is the transition defense really bad?” And the response was, “You’re the first person to answer that.”

Jimmy Soni
Huh.

Ryan Resch
And I said, “Well, we can just show them that, like, where do we rank in transition defense? This combination, when they’re together, is very poor.” Yeah. But it has to come back to the why. Well, the why is that, you know, it’s very difficult to play two centers because they’re, you know, the tallest players typically on the floor, the heaviest players on the floor. And they’re usually not the fastest, they’re usually the slowest. And if you’re playing both in a league that is increasing in pace and speed, and they’re just going to outrun you at some point, like, that’s what’s going to happen. Yeah. And the data was showing that.

Jimmy Soni
Yeah.

Ryan Resch
And so my understanding is that answer helped get that internship. And I was very grateful to get the call.

Jimmy Soni
Just out of curiosity, they had not discovered this on their... You didn’t discover it. You knew the answer? Because that was a very...

Ryan Resch
Well, I mean, it was a guess. Yeah, because I didn’t see the data. I didn’t have anything in front of me. I was just proposed the question.

Jimmy Soni
Yeah.

Ryan Resch
And they had the data. They knew the answer.

Jimmy Soni
Got it.

Ryan Resch
I think what they were looking for, which is a very interesting data interview topic, is, can this person creatively identify something? Can you think, I guess, outside the box of whatever the, I don’t know what other answer there might be.

Jimmy Soni
Right.

Ryan Resch
But I get the internship and I do the three months, maybe three or four months over the summer. In the NBA, so the NBA calendar is July 1 to June 30 every year. So the salary cap resets on July 1. So that’s when you can start signing players again. That’s why the draft is at the very end of June. It’s the Finals and the draft at the very end of the NBA calendar. And I started, I believe, right before the draft. Yeah, it was right before the draft. I did a little bit of work on that.

Jimmy Soni
Yeah.

Ryan Resch
Where it’s just basic, hey, interpret these statistics for these draft prospects. This would have been the summer that the Suns drafted Marquese Chriss and Dragan Bender at 4 and 8 in the lottery. That led into Summer League. I’m sorry, free agency, where we’re just doing, again, what would you value, like, this player’s contract at based on what they’ve done in the past? And I was just sitting in my cubicle, which was just doing that work by myself. And went to Summer League, had a good time. August is completely dead. And that was the end of the internship. And I was fortunate enough that they kept my database access on. So for whatever reason, they decided that was worth it. And I just kept producing work when I went back to Baylor.

Jimmy Soni
Oh, wow.

Ryan Resch
So I was still working at Baylor and I was still doing, like, little side projects.

Jimmy Soni
Oh, that’s great.

Ryan Resch
For Suns analytics, eventually building out the web application that they used in the war room, which is where the draft is held, in Phoenix in 2016. No, 2017. And probably because I just kept doing work, they’re like, “We just feel bad. We know we have to hire this guy.” And they hired me as the coaching analytics person, which effectively meant that I was hired to sit with the coaches, sit on the bench during games, and interpret statistics and data for the coaching staff. So, be that communication bridge that looks at the numbers and then is able to relay what exactly is going on.

Jimmy Soni
Got it. Out of curiosity, because having somebody like you in the background makes a lot of sense to me. Game’s done, the week is long, there’s nothing happening, your day job is looking at the analytics and helping to come up with insights. What does someone like you do in that role when you’re on the bench next to the coaches? Are they asking you specific questions? Or is it just, you know what, Ryan? Yeah, this makes you feel real good. We’ll have you here. It’s really just window dressing. You’re gonna have a clipboard. It’s not gonna have anything on it, but when the camera pans to you, you’ll have a clipboard there.

Ryan Resch
I mean, there are clips of me clapping on my clipboard. I laugh because it’s a little bit of a loaded question in that there is no purpose. Like, you kind of realize it, too, when you’re in the moment where it’s like, all right, it’s first quarter. Team’s taken eight shots.

Jimmy Soni
Yeah.

Ryan Resch
Smallest sample size you can possibly imagine.

Jimmy Soni
Right.

Ryan Resch
I can tell you where it may go. Yeah. If we shoot enough shots, it may look like this and, right, regression to mean may occur. There’s a lot of qualitative maybes and, like, we’re kind of theoretically thinking these things. Yes. It’s not helpful in game. Like, it’s really not. And it goes back to something that I used to talk about with one of our coaches at Baylor, Coach T, where we would talk about, what is the best way to prepare for a game?

Jimmy Soni
Yeah.

Ryan Resch
Because I think maybe FiveThirtyEight, back in the day, did a study of how many decisions an NBA coach makes in a game. Some absurd number. Exactly what you would think. And you can’t, no human can process all of this information in real time. In real time, manage the players, manage the emotion of it all, manage your staff. Like, there’s so much going on in the moment. And what we eventually came up with was, like, you have to have plan A, which is we’re going in with this style of play, we’re going to do this offensively, defensively, our team knows how to do these things. And then you have to have plan B, which is, if plan A fails, we’re moving to plan B. Yeah. And then if you get to plan C, guys, we’re probably done. We’re probably losing. And, I mean, on the data side of it, it goes back to, like, whether it’s qualitative or quantitative information, your preparation needs to be there pregame.

Jimmy Soni
Yeah.

Ryan Resch
Before that ball goes up at 7:07pm. Yeah. You need to be prepared. Right? Like, you need to have a coach or someone behind you that taps you on the shoulder and says, “Hey, our goal was, you know, a three point attempt rate of 40% and we’re only at 35%.” Right? But then a good coach, their next question will be, okay, what’s wrong?

Jimmy Soni
Right.

Ryan Resch
Like, why are we so low?

Jimmy Soni
Yeah. And you’re saying this is happening at halftime? Or, well, after the game is over? Or you’re saying after the game’s over, before the next game, to understand what went on?

Ryan Resch
I think that you have to prepare definitely before. Yeah, no doubt. I think at halftime you have to have a very structured process that you go through. Basically you have, like, 15 minutes. Yeah. Some percentage of those minutes must be devoted to talking to your guys. That’s the most important thing. Some percentage at the beginning must be devoted to, okay, let’s review our strategy and our tactics and our style of play. Yeah. There’s a lot of value that can be done there if you can really refine that process. Obviously the pregame prep is extremely valuable. Right? Postgame debrief, hit or miss. Because it’s so emotional after a game. Like, you are coming off of an adrenaline high, whether you win or you lose, everyone is. So it’s really not the best time to chat right after your game.

Jimmy Soni
But as evidenced by any number of press conferences that go so badly awry.

Ryan Resch
Exactly.

Jimmy Soni
Right? And actually it explains the monotone, monosyllabic responses that a lot of players give to questions. Right? There’s no room for creativity after that kind of thing.

Ryan Resch
There’s not. Like, you’re emotionally depleted. Right? And there’s just, you don’t want to talk, you certainly don’t want to talk in front of the camera.

Jimmy Soni
Right.

Ryan Resch
And it’s the in the moment data assistance that I think is, having literally done the job, I don’t think that there’s a lot of value that it’s going to create, because what you should be focusing on instead is training your coaches and the people making decisions in game how to think this way.

Jimmy Soni
Yeah.

Ryan Resch
So instead of me being like, “Hey, we’re not shooting enough threes”...

Jimmy Soni
Your coach, who is in church: “Get back to your cubicle.”

Ryan Resch
Right, exactly. Instead of saying that, you have a coach who says, “Hey, my job is the offense. I know what our threes should look like. I know how they’re generated and know what quality looks like. We are not getting enough off ball screen threes.”

Jimmy Soni
Right.

Ryan Resch
We’re just not.

Jimmy Soni
Right.

Ryan Resch
And that is useful information that helps the coach and helps the players. Whereas, “Hey, we’re not shooting enough threes” is not useful information. That’s a fun fact.

Jimmy Soni
Great. That’s a super fun fact. When you come into the organization, you know, as you mentioned, the Suns were coming off a bad stretch and there was a leadership change. There was also an ownership change. Can you talk a little bit about what it was like being a part of that? Because, so you finished up another year at Baylor, you’re doing all the side hustle work for the Suns. That is what it was. They hire you based on the strength of that side hustle work and then you join them. But you’re in the middle of chaos. Right? I mean, it was, the GM changed and the owners changed. So it was...

Ryan Resch
That changes constantly.

Jimmy Soni
Yeah.

Ryan Resch
I can tell you that it was the exact opposite of what Baylor was, which, I mean, Scott Drew is still the head coach at Baylor. He’s been there for, I mean, my goodness, 25 years now.

Jimmy Soni
Wow.

Ryan Resch
And Phoenix was on, I believe it was the second coach in two years, and it would go on to be the third and then the fourth. Like, there was a whole host of change on the coaching side. We did go through a basketball operations executive change. So our general manager changed when I started full time. James Jones started, who was the player that I mentioned earlier from the Miami Heat. He had just retired, seven straight NBA Finals appearances, played with LeBron James on all of those teams. And LeBron publicly called him the greatest teammate of all time.

Jimmy Soni
Wow.

Ryan Resch
And I can now attest to why. I love James dearly. And he starts full time the time that I start full time. He starts in the role that I would finish in. So there’s a bit of a, like, a bookend here.

Jimmy Soni
Yeah.

Ryan Resch
And he’s coming from winning championships. I’m coming from Baylor basketball, where we’re second weekend NCAA tournament teams. We didn’t win the Big 12 yet, but we were in the championship game in the tournament quite a bit. And you go to losing.

Jimmy Soni
Right.

Ryan Resch
You go to losing.

Jimmy Soni
Yeah.

Ryan Resch
And it is culture shock.

Jimmy Soni
Yeah.

Ryan Resch
James, I believe in his 17 year career, however long it was, missed the playoffs once. I’m coming from spoils and riches at Baylor.

Jimmy Soni
Yeah.

Ryan Resch
And we just kind of bonded over this.

Jimmy Soni
Wow.

Ryan Resch
This weird culture of losing.

Jimmy Soni
Yeah.

Ryan Resch
And there’s really no other way to say it. And I give him so much credit in that he had the perspective when he took over that, it’s very easy, you hire a GM, you hold the press conference: we’re going to compete for championships, we’re going to play hard, we’re going to do all these things. So easy. Like, you can win a press conference. It’s very easy to win a press conference. It’s not easy to win the game.

Jimmy Soni
Right.

Ryan Resch
Like, those are two very different things. And James came in and his very first strategy, well, on day one, he did, you know, change over quite a bit of the staff.

Jimmy Soni
Yeah.

Ryan Resch
Which I think was necessary at the time. And we became a very small, lean operation. I call this now the Startup Suns, for that period of time.

Jimmy Soni
Why were you not part of the changeover? Because you came in under the old management. Yeah. So how did you manage to stick around?

Ryan Resch
I mean, truthfully, I didn’t have an office. I didn’t have a desk. And James, being who James is, told me, like, “Sit on the other side of my desk and work.” Okay. So we just had a really strong relationship from that. He’s also a very rational thinker. He loves data, he loves technology. But he also understands that human component to such a degree as well. And he’s an unbelievable teacher, I think, too. And if you’re willing to learn from him, then you can become one of his people.

Jimmy Soni
Right.

Ryan Resch
But the first strategy that he implemented was raising the floor. It’s not championship ceiling, championship expectations. It was, no, guys, we’re going to raise the floor. Yeah. The floor is way too low. Like, the competitive floor, the talent floor. And this is not just players. And this is the beauty of having a former player as your lead executive.

Jimmy Soni
Yeah.

Ryan Resch
Which I think is so important. Is the individual who has been in those championship games, who has won the title, who has made the threes, who has, you know, defended the best players in the league...

Jimmy Soni
Right.

Ryan Resch
Who understands what these players are going through. They will hold the rest of the organization to that same standard that the players will hold themselves to. And it’s so important. And he literally, he was like, “It’s not sexy, but raise the floor.”

Jimmy Soni
So how did you do that? Like, what are some of the key, both the data and analytics components in your job, but then also just organization wide. How did that happen?

Ryan Resch
You look at age first, and the Suns were extremely young. Yeah, it’s very popular in the NBA to tank. This is another huge thing in sports, is if we lose, then we’ll get a higher draft pick. If we get a higher draft pick, we will maximize our chances of getting an All-Star or franchise player. Yeah. Not incorrect. You know, if you get the number one pick in the draft, then, yeah, you’ll have a much higher chance of drafting an All-Star franchise player from that class than anyone who comes after you. That’s basic logic. Right? What the tanking debate fundamentally misses, because the Suns were publicly tanking and we were there at the very early days and went the exact opposite... What they were missing, the tanking proponents, I should say, are missing the, again, we come back to this, the human factor. Sports is an extremely unique environment. It is the only publicly played zero sum game in the world. I mean, literally everything’s public and there will be a winner, there will be a loser, and it is also time bound. So every year you get one year and then we’re resetting, go again. There’s no rollover effect. You don’t have to carry things over, any of that. When you think about that on a macro level with games, it’s true. But on a micro level as well, where these players, like, we’re drafting the replacements.

Jimmy Soni
Right.

Ryan Resch
It’s crazy when you think about, like, the cycle of this, and it’s arguably, like, deeply unfair as well. Where it’s like, someone who is an NBA player will get pushed out because we’re bringing in this 18 year old high potential. Yeah. And when we talked about, like, James raising the floor, it was finding the value in the older guy. Again, like, finding the value in the four year player, like Cam Johnson, who we drafted at 11, James’s first draft, and we got panned for it.

Jimmy Soni
Right.

Ryan Resch
Cam has since gone on to have an incredible career. He’s a great person, he’s a great player. Like, fantastic.

Jimmy Soni
Yeah.

Ryan Resch
And it’s things like, I mentioned the age. It’s also things like teaching the front office staff what the player is going through when you talk about tanking. Because they hear, “You want to draft my replacement.”

Jimmy Soni
Oh, interesting.

Ryan Resch
“You want to bring in the guy who’s going to take my job away.”

Jimmy Soni
Right.

Ryan Resch
Or the coach hears, “You want me to lose so that you can fire me.”

Jimmy Soni
Right.

Ryan Resch
And then we can continue. And you just can’t, like, it’s so hard to win a championship to begin with. Like, your odds are so infinitesimally small to do this to begin with, that if you don’t realize, like, the consequence of these strategic choices that you’re making, yes, you don’t have a chance.

Jimmy Soni
Right.

Ryan Resch
And this is why, like, Oklahoma City, for example, took you to the tanking process extremely well. I don’t think that they ever publicly called it that, but...

Jimmy Soni
Of course not. I mean, this is one of the curious things about tanking, is you can’t say you’re tanking. If you’re tanking, you’ll get in trouble. Yeah.

Ryan Resch
The integrity of the game. But Oklahoma City, they did an amazing job of keeping their culture so strong. And I give Sam Presti all the credit to that. Like, he is a fantastic executive. Absolutely fantastic. And they built this, you know, this program where it’s, hey, we all know what we’re going to do for the next couple of years and then we hope that we’ll be champions on the other end of it. Yeah. And I think if you do it in that deliberate manner, right, then you definitely increase your chances of success. Yeah. It’s when you do it in kind of the manner that’s, I think we’re supposed to do this because we’re told that you should tank if you’re not good because you don’t want to be in the middle. Right? Like, you know, it comes down to, you understand the strategic consequences of the strategic decisions that you’re making.

Jimmy Soni
Interesting. So when you’re in the day to day of this, how is, I guess, how is the Suns job different than the Baylor job? When you got to that grad-- in both cases you’re looking at analytics, you’re looking at data. What were the differences between those two environments?

Ryan Resch
At face value, the roles were very different post James taking over the Suns. So that was when I became his chief of staff, director of strategy. He would then go on to win the 21 executive of the year. I believe it was 2021. And so the role was more expansive, for sure. Helping out in operations, salary cap if that was needed at the time, traveling with the team quite a bit to basically be a front office presence for them if something happened. Yeah. Whereas, it’s funny now that I say it, it sounds a little bit closer to the manager role, where it was kind of like the catch all situation and just being around to do these things that need to get done. Whereas the Baylor data roles and even those early Suns data roles were very, as you would think they are, behind a computer, looking at numbers, looking at spreadsheets. Thankfully, at that time in the NBA, well, that’s another difference, is the NBA had a much richer data set. So optical tracking data came online right around the time that I was an intern. A company called SportVU, which had installed cameras in all of the arenas, and they could track, I think it was 24 frames a second from six cameras at that time, the XY coordinates of the players directly using the ball. And now it’s XYZ coordinates with Hawk-Eye, which is the new camera provider. And so we were extremely data rich. And so we would spend a lot of time kind of playing in that sandbox of the XY coordinates.

Jimmy Soni
Right.

Ryan Resch
And then as the role increased in scope, it was less of that hands on coding and more of program building, I think, is the way to think about it. And I kind of bounced around. I was very lucky that James trusted me so much. And over the course of my time at the Suns under James, led or managed everything except players and coaches in basketball operations. So scouting at one point for a couple of years, health and performance for a year, operations strategy, so data science, salary cap, those things. Yeah.

Jimmy Soni
So you go from Baylor and doing the data stuff to the Suns at a period of real transition for the Suns. Like, what is different about the job that you were doing in one, you know, in both cases you’re working with data and you’re trying to find insights that are going to help the team. What are the differences between the role in the NBA and the role in college?

Ryan Resch
Kind of at the top level, the NBA is a much richer data set. So when I joined the Suns, this was right around when optical tracking was taking off. So optical tracking was introduced to the NBA through a company called SportVU, which installed, I believe it was, six cameras in the arena, the rafters of the arena, at 24 frames a second, where we could track the XY coordinates of every player, the ball and the referees. And now they can do the XYZ coordinates with the latest technology, which is pretty cool. And so we would spend just quite a bit of time in those early Suns days, not dissimilar to what we did at Baylor, where it’s like, okay, we have our hands on all this data, now let’s build something. And the optical tracking data could produce really cool new metrics. Like, okay, let’s measure how far the screen defender is from the screener, and does that matter if our center is 6ft behind the screen versus 2ft behind the screen? Why does this question matter? Well, at that time, if you’re trying to invite the mid range shot and take away threes, which was the popular style of defensive play back then as teams are shooting more threes, then you want to know, can my seven foot center play at the level of the screen? Does he need to play back? If we do play back, are they going to pull up? Is he going to contest? And there’s a whole kind of, like, chain of thought that goes into that. That’s really interesting. The role itself, though, it grew very quickly under James, and I’m really lucky that he trusted me as much as he did. And I eventually would go on to lead or manage every team within basketball operations outside of the players and the coaches directly. So health and performance for a year, which was athletic training, strength, conditioning, nutrition, sports science, those kinds of things. So keeping the players healthy, getting them stronger, helping them play better from a physical, athletic standpoint. Scouting, which is obvious, professional scouting, amateur scouting, so college basketball. Data science. The salary cap side of things as well, which is super interesting. Kind of ran the whole gamut there. And then eventually my last year ran operations. Yeah. Which was the true day to day of being in it.

Jimmy Soni
So I want to dive in, because, and we’ll link to it in the show notes, but there was this really interesting interview you did about sports and analytics and AI, and you talk a little bit about what happened when data first arrived at the NBA, where you finally have optical tracking data. And then, as I understand it, a company came around and built dashboards. And for the first time, I guess, in the league’s history, this data that, you know, would have had to be cobbled together and, you know, hacked together before is now easily visible to teams. Talk a little bit about that moment, what happened, and kind of what you saw as that happened.

Ryan Resch
Yeah. When SportVU came in and they introduced optical tracking data, it delivered as all nascent forms of data deliver, which is, you know, structured to some degree. But you need to know how to write SQL and you need to know how to write Python or R at a base in order to actually interact with these numbers and make them mean anything of relevance.

Jimmy Soni
Yeah.

Ryan Resch
And, you know, around the mid 2010s too, in the data science community, the tech community, machine learning is really starting to take off. So Facebook algorithms, AlexNet, mentioned previously. You know, it’s insane to talk about it now like, AlphaGo. Right? Like, the things that would then go on to truly change the world are coming into the public conscious. And a company called Second Spectrum, and they did a great job with it. They solved the problem of needing to have technical coding chops to interact with this optical tracking data by building machine learning algorithms to track the actions of these coordinates. So instead of me having to now figure out, okay, a middle pick and roll occurred at 7 minutes and 15 seconds in the second quarter by our players, Second Spectrum built the algorithms, the machine learning algorithms, to actually identify this. And then from there we could split that and filter it into a host of different metrics, whether it’s on the left side of the court, the right side of the court. Basically you’re able to summarize and assess the game at a much more granular level. And they tied film to it. So that was also a huge innovative side of it that again goes towards solving the communication problem. So now coach sees, my middle pick and roll is 1.20 points per possession. And then here’s the 30 clips of our guys doing it. You can reinforce, okay, why is it 1.2? Let’s watch the film to find out.

Jimmy Soni
Right.

Ryan Resch
And super helpful. Yeah. Extremely useful. Very advantageous when you are one of the few teams that has it. But as with all things, it becomes democratized and everybody has access to this data and this information. And something that started happening my last few years in the league was this constant conversation around, is everyone playing the same way? Is there a homogenous style of play?

Jimmy Soni
Yeah.

Ryan Resch
Is everyone running middle pick and roll, trying to shoot threes and either switching ball screens or playing in the deep drop on ball screens? Where is the innovation in our style of play?

Jimmy Soni
Right.

Ryan Resch
And I think it’s a fascinating conversation.

Jimmy Soni
Yeah.

Ryan Resch
And there’s been some studies that say it is happening, some studies that say it isn’t happening. This is one of those topics where, if people are talking about it, if the perception is that it’s happening, then it’s probably important to figure out why that perception exists. Yeah. And it occurred to me one day that we really did all have access to similar data. Right? The same data.

Jimmy Soni
Right.

Ryan Resch
And, you know, you think a program would get, you know, ridiculed if they didn’t shoot, you know, 30, 35, 40 threes. You know, your coach doesn’t have good shot selection, blah, blah. What kind of behavior does that drive?

Jimmy Soni
Right.

Ryan Resch
That the coach now is like, okay, what does the data say I should do?

Jimmy Soni
Yeah.

Ryan Resch
But if you’re basing it off of just what a dashboard says, you’re looking at lagging indicators. You’re looking at what others are doing to win.

Jimmy Soni
Yeah.

Ryan Resch
You’re not drilling down and saying, no, what is it for our team? Back to that two by two. What is it for our team’s context, for how we win? And so when you have this kind of democratized dashboard, instead of proprietary questions, proprietary data, or proprietary metrics built on publicly available data, right, is really the way to do it. With the optical tracking data, you do end up in this kind of path dependency. Okay, middle pick and roll seems to be the most efficient action.

Jimmy Soni
Yeah.

Ryan Resch
Switching ball screens is extremely efficient as well. And then it’s kind of this race toward some kind of false optimization, in a way.

Jimmy Soni
The opposite problem is what many people read in the Moneyball book, right? So on the one end of the spectrum, you’d be like, data is useless. Right? That’s over and done with. Most team owners at this point are going to emphasize the numbers. Right? Now you go to the other place where, because the numbers are the same numbers everybody else is looking at, you get, like, a homogenized style of play, right? Or you’re all doing the same things because the numbers suggest the same things. So that’s an interesting thing to square, whether you’re a GM or a coach, to say to yourself, okay, how do I make sure I’m not captive to the metrics that everybody else is benchmarking against? How did you think about that internally? Like, how did you make the most use of the dashboards that, you know, a company provided, while not then allowing it to drive the same conclusions that everybody else is going to draw, so that you’re basically playing the same game as everybody else?

Ryan Resch
I think it follows a path of what you kind of described, where the information that’s readily available is great for education. It’s great to tell you what is going on. It’s great to tell you what happened. It’s great to tell you, okay, under these conditions, this existed.

Jimmy Soni
Yeah.

Ryan Resch
It does not tell you moving forward, if we face those conditions again, will this outcome still occur? And I think if I could go back, then I would probably emphasize this point stronger with the analytics team, and I would have us just spend more time asking better questions to get us back into the mindset of XY coordinates. How do we build the model that shows whether our center should be 6ft or 2ft or 5ft? Can we get that on what’s available? Yes, but this is different because of how we teach our defense. Like, if we are able to define our shift defense, our help line defense, and we know where these guys are supposed to stand, then we should also be able to code out that logic and get those metrics that are more Suns proprietary or more team proprietary than just taking what is available on the dashboard. Because they don’t know our defense. Right? Nor should they.

Jimmy Soni
Right.

Ryan Resch
And in this, again, it comes back to, I think, like, data is not a holy grail. Like, it is not a panacea for all of this stuff. It is another area where you can find competitive advantage if you know how to use it, just like any other tool. As cliche as that argument is, yes, it is a tool. Yeah, you know how to use it, then you can find advantage with it. And if you do talk to these leagues where it has become kind of more pervasive, like baseball, for example, it’s really hard to find the next differentiation lane of data in baseball, because there’s been 20 years, tons of money, and you’ve had an owner class in Major League Baseball that comes from these more rational worlds that use data in their private equity shops or whatever they’re doing in their business life. And so they almost, like, optimize it to the point where if you don’t have it at an A plus level to begin with, like, you’re just behind. Right? You’re not even talking about eking out advantage at that point. You’re just like, we have... It’s a model that I would use at the Suns, was like, what is the negligence line? Like, if we are below this negligence line, then we must focus everything on getting above it. And if we are above it, now we can start talking about, okay, what are the cool, unique ways that we can differentiate ourselves from this? So you think about, let’s say if we talk about basketball, for example, style of play. So style of play is just literally, how are you going to play offense? How are you going to play defense? What are you going to focus on? Basketball, at the end of the day, just like all sports, is a possession game. You want as many shots on goal as you can get. Field goal attempts plus free throw attempts, you want that number to be higher than your opponent, not in a reckless way. Like, don’t cross half court and just throw the ball up, unless you’re Steph Curry. But you want to just maximize that number. Yeah. So what are the ways to do that? Well, rebounding is one of those ways, and turnovers is one of those ways as well. So either you don’t turn it over, you get your opponent to turn it over, or you grab the ball offensively and defensively, so your opponent cannot grab the ball. It’s really that simple. If you don’t have rebounding and turnovers dialed in, like, if you’re not top 15 in those areas, negligence line would say, focus on that. Focus on defensive rebounding and how you’re going to get better from a roster perspective, from a coaching perspective, from a front office perspective, culturally. How are we going to become a better rebounding team?

Jimmy Soni
Interesting.

Ryan Resch
Before you try to be like, let’s get cute by shooting more threes, like this.

Jimmy Soni
Right.

Ryan Resch
You have to get above the negligence line for your style of play. And so I think that is kind of a helpful model to think about all of these things being tools. When do we start making strategic choices that genuinely differentiate us instead of just having fun with...

Jimmy Soni
Right. Fun with the data.

Ryan Resch
Yeah, exactly.

Jimmy Soni
Yeah. And did you find that, in a way, what you’re describing is the opposite of what the fiercest critics about data in sports would have said, which is, they’re like, it’s going to make the game boring. It’s going to get the game over to eggheads. It’s going to be, you know, bean counters making all the decisions. What you’re actually saying is, no, like, the more information you have, if you’re a bad team, you’re going to lapse into homogeneity anyway. Right? But actually having more information gives you an ability to tailor your particular style of play to your particular opponent or to the group you have. And there’s room for a ton of innovation, even when every movement they’re making has been dissected to the nines.

Ryan Resch
That’s what I believe.

Jimmy Soni
Okay.

Ryan Resch
And I think that is, you know, if humans are just modeling the behavior of other people, at the end of the day, like, teams do the same thing. Programs, institutions, they all do the same thing. So Golden State is going to win all these championships. How do we play more like Golden State? How do we get smaller? Because they’re playing small ball.

Jimmy Soni
Yeah.

Ryan Resch
Well, one of the most important factors of their small ball is they have Draymond Green, who is arguably the smartest defensive player in NBA history. Like, someone who just redefined what it meant to be a small ball center.

Jimmy Soni
Right.

Ryan Resch
And if you don’t have Draymond Green, probably not the path for you to go down. Right? And so, again, if we return to this, like, negligence line model. Basketball is played in a vertical plane. The scoring goal is 10ft above the ground. It’s not like soccer, where it’s, like, low to the ground, you can kick the ball in there. Height and size and jumping ability will always have some level of advantage. So you can’t build a small team in pursuit of playing small ball.

Jimmy Soni
Right.

Ryan Resch
You’re below the negligence line here. Unless you have that defining factor, a Draymond Green type person. And it is exactly what you said, where it’s, okay, if we can get all of this information, as soon as we establish our floor and our foundation. Again, it goes back to James’s model of raising the floor.

Jimmy Soni
Yeah.

Ryan Resch
If we can establish a really high floor here where all of our fundamentals are taken care of. The best coaches will preach fundamentals. Read any John Wooden quote out there. He’s only talking about fundamentals and, like, first principles. Like, you see this in the best tech founders, all of this.

Jimmy Soni
Yeah.

Ryan Resch
Where it is this, like, set the floor really high.

Jimmy Soni
Yeah.

Ryan Resch
Get it there. And then you can start, like, branching off and doing these things. Where you have Steph Curry, who is fundamentally the greatest shooter of all time.

Jimmy Soni
Right.

Ryan Resch
You have Draymond in his role, Klay in his role, Andre Iguodala in his role.

Jimmy Soni
Okay.

Ryan Resch
Now we can start, you know, bringing in these people who can differentiate from there. Or these styles that can differentiate.

Jimmy Soni
So you transitioned at some point from the Suns to your role now in private equity. Walk us through kind of that latest iteration in your career.

Ryan Resch
Like you asked earlier about an ownership change. Yeah. And I like to joke that my NBA bingo card was full except for winning a championship, which is the worst part.

Jimmy Soni
You got to the championship.

Ryan Resch
We got to the Finals. We did lose, unfortunately. And I did go through an ownership change as well. And part of that ownership change, I got to meet Justin Ishbia, who is the founder of Shore Capital Partners. And I spent a lot of time with Justin and with Shore from 2023, when he and his brother bought the team, his brother Mat bought the team, through May of 25, when I did leave Phoenix. And I came to just really appreciate how Shore was built and how Shore was operating. Extremely process driven, very data heavy, very much a sports culture.

Jimmy Soni
Right.

Ryan Resch
In that sports are very much a part of what they’re doing day to day. And I learned so much from them in such a short period of time. Nine years in the NBA is a lifetime. We had done the whole, you know, start from the bottom, get to the top line again. I think one of the through lines of my career has been, like, incessant problem solving. So it is like, just solve the next problem in front of you. And I just wanted a new problem. Like, I wanted a new challenge. And I was very fortunate that Justin gave me an opportunity to join Shore for a year and then recently moving over into 1949 Capital, which is also part of Justin’s world. And it’s been a fascinating look at the difference between the zero sum nature of sports.

Jimmy Soni
Right.

Ryan Resch
And the non zero sum nature of everything else.

Jimmy Soni
Right. And that’s exactly what I was going to ask you, which is, in your prior world, there are winners and there are losers, there are wins and losses. And now you’re in a world, private equity, where there’s still winners and losers, but it’s not zero sum. There are partnerships to be made, there are deals to be made. How have you thought about that transition from one to the other?

Ryan Resch
I would tell you that I miss the games. Yeah. In the sense of, there’s nothing quite like being a part of a winning team in sports. Like, the ride of that.

Jimmy Soni
Yeah.

Ryan Resch
The opposite is also true. It’s extremely hard to be part of a losing team. Right. But what I have really enjoyed about kind of the non zero sum world is what you mentioned, which is, like, you get to finally live out what game theory would tell you, which is cooperation will oftentimes lead to the best outcome.

Jimmy Soni
Yeah.

Ryan Resch
And you get to take these lessons from sport about team building, about setting and raising the floor, about how do different personalities work with each other in the best way, and try to form those partnerships and get the most and the best out of, like, the unit instead of just the individual person. And I’m also very fortunate that, you know, Shore and Justin are very data driven and very AI focused as well. And so the overlap has been that Shore and Justin, in that environment, is very data heavy. Yeah. And very AI forward, I would say, for sure. Shore started an AI team very early. I think it was early 2025 that they started hiring AI specific people to go into the portfolio companies and implement these solutions, which is incredible to think about how early that was. And it was having the opportunity to go to an environment that is that forward looking.

Jimmy Soni
Yeah.

Ryan Resch
That excited me. And helping them roll out a lot of their AI enterprise tools over the last year has been an unbelievable learning experience. Like, tech deployments are one thing, but rolling out frontier models to an entire private equity firm is a whole nother beast. And learned a ton there and have since gone deeper on the AI space and the sports space.

Jimmy Soni
And, you know, there’s that line, like, prediction is always hard, especially about the future. But I’m curious what you make of AI as it has been adopted in sports. Like, where are we at? Are we early innings? Is it far enough along? Because a lot of the things you’re talking about with, like, sabermetrics and all this, did that pave the way for AI use? Is it still kind of where the rest of the world is, which is, we’re figuring ourselves out in this moment? Right? Like, what is the interaction or intersection between sports and AI in 2026?

Ryan Resch
From what I’ve seen, absolutely early innings and absolutely still in this formation of, where are we? Like, what exactly is the impact that this is going to have? So, not dissimilar to what is going on in every other industry. And I think when you zoom back out and you say, okay, who is using AI the best? What can we learn from them? At least in my experience, it’s been, if you think about AI transformation as operations transformation. So operations being, how do we take this unbelievable amount of information that we are receiving, synthesize it and then make a decision on it?

Jimmy Soni
Yeah.

Ryan Resch
And that can happen at a very small level, such as, how are you going to stock the snack bar at your office? All the way up to a very, very high level of, where are we going to move this capital so that we can invest it? If you think about it in that way, then you can start to identify places where having this, I don’t want to call it a logic machine, but this ability to extract structure and synthesize information and pattern match at a scale that we have just never seen. Once you can start finding, like, the links in your chain of operations, be like, okay, this looks like data extraction for the snack room, because we need to have a better sense of how much money we’re spending on whatever, you know, yogurt or whatever, structured in that way. And then AI can help you there. I think that sports is still trying to figure out what that operations chain looks like.

Jimmy Soni
Right.

Ryan Resch
And do I think that there are coders out there who are using Codex and Claude Code?

Jimmy Soni
Of course.

Ryan Resch
And they absolutely should be doing that. How do we now take that capacity and get us back to getting our hands deep in that raw optical tracking data so that we can build new novel metrics, so that we can just answer more novel questions? Like, my whole thing on tanking, where, you know, I think that there is probably a paper waiting to be written by someone who can examine, you know, the kind of perverse incentives of tanking as well. Where, if you were only considering it from the perspective of the general manager trying to acquire an All-Star, yeah, sure, you might have found, like, an equilibrium there. When you consider it from the perspective of players and coaches and owners who need to look good in the community, yeah, maybe it’s a very different calculus. There’s not enough time or attention within a sports team to do that because it moves so fast, because we are on a clock. Every year it restarts. But now that you have AI, like, a good ownership group should be asking, okay, you think that we should tank? Model that for me.

Jimmy Soni
Right.

Ryan Resch
Like, actually run through all of the different scenarios of where this could go well and where this could go wrong. All the way down to, when you think that we’re going to be contending for the number one pick, who’s in that class? And are they Victor Wembanyama roles of generational talent?

Jimmy Soni
Right.

Ryan Resch
Because that is a different proposition than, you know, if you’re just some kind of run of the mill class.

Jimmy Soni
Right.

Ryan Resch
But my hope is that is where AI and sports will get back to, is now that we have the ability at a much lower cost to ask these deeper questions instead of just trying to win the game in front of us. Yeah. We can just produce more novel insights and more interesting ideas.

Jimmy Soni
It’s one thing to be in the front office and doing this. One of the things that AI has done is it’s democratized the ability to ask these questions without knowing how to code in Python or in R or whatever. Do you think that we’re going to see the first generation of players who dive into their own data or into sports data to understand the game?

Ryan Resch
You know, it’s funny, we traded for Chris Paul.

Jimmy Soni
Yeah.

Ryan Resch
And he was a heavy user of Second Spectrum. And I was very impressed by that when I saw that. And it makes sense when you think about how Chris plays. And I have an immense amount of respect for him. He was incredible for us. And some of the best players, you think about James and his career, these players understand themselves. They understand truly their strengths and their weaknesses and they understand what to focus on in practice, what to focus on in warmups. It is very dialed in to a degree that it teaches you the importance of specificity and detail when you watch how these best guys work. And data can help them with that. Yeah, it absolutely can help them with that. Where it’s not, you know, it’s not so much, okay, the front office may use it against me in contract negotiations.

Jimmy Soni
Or somebody’s forcing somebody, like, Ryan, kid Ryan shows up with his glasses and whatever, he’s got his spreadsheet and he’s got his clipboard that has nothing on it, but we let him hang out at the game. He’s telling me something about my spacing when I’m doing a screen. This is like the, you know...

Ryan Resch
Yeah.

Jimmy Soni
It’s more that the player could own this conversation.

Ryan Resch
Exactly. I think that’s what, if we’re moving toward kind of this democratization of information and intelligence, then I hope that is where it goes.

Jimmy Soni
Yeah.

Ryan Resch
Is where the players really understand how they can benefit from it.

Jimmy Soni
Right. So if we take ourselves outside of the work context, and, you know, I want to be respectful of your time, want to wrap up. When you’re thinking about AI right now, what have you personally been most impressed by? Right? Because you came of age in a profession and in day to day work where you were taking huge amounts of data and trying to wring insights out of them. So what’s most exciting to you, or what tools do you use? What’s your day to day interaction with AI like?

Ryan Resch
I don’t know if this will be an exciting answer, but I think the thing that I am most interested in right now is using these coding agents with my workspace. Workspace I would have previously called a working directory.

Jimmy Soni
Yeah.

Ryan Resch
Someone can call it a repo, whatever they want to call it. But having my workspace now be designed not for me to read.

Jimmy Soni
Yeah.

Ryan Resch
But for agents to read, for agents to navigate.

Jimmy Soni
Yeah.

Ryan Resch
It’s been such an interesting problem to solve. Okay, Ryan is not navigating this as much as he otherwise would have been, like an old Dropbox setup. Right? Ryan is building agents who need to read the work of the other agents, or what they’re producing and what they’re writing to this workspace. Yeah. And that is two very different things.

Jimmy Soni
Yeah.

Ryan Resch
And I have torn it down, last month I think I’ve torn it down four times and rebuilt it. I have more copies of a working directory than I ever thought I would have. But I think that speaks to kind of the age that we’re entering also, which is you do have to change your perspective of how you used to approach work fundamentally.

Jimmy Soni
Right.

Ryan Resch
And I think it maybe makes me a better manager of people, to be honest, because you have to be so much more specific in what you’re looking for and asking for. Maybe not five years from now when these models are even better.