What if the biggest barrier between you and your dreams isn’t talent, connections, or luck— but simply the belief that you need permission to act? Jay Yang joins Infinite Loops to challenge one of the most limiting assumptions of our time: that opportunities must be handed to us rather than created by us.
At just 16, Jay cold-emailed the CEO of Beehiiv with a concrete plan that led to an internship. At 17, he sent Noah Kagan a 19-page audit of his email funnel with ready-to-ship assets, ultimately becoming head of content and helping put “Million Dollar Weekend” on the New York Times bestseller list. His secret? Understanding that preparation beats bravado, that most doors don’t even have locks, and that the fastest way to get what you want is to do the work upfront and make saying “yes” a no-brainer for others.
This conversation dives deep into Jay’s philosophy of permissionless action, exploring why most people accept the “standard pace” when there’s actually no speed limit, how to reprogram limiting beliefs through small wins, and why high agency people focus on outputs while low agency people get trapped tracking inputs.
I hope you enjoy this conversation as much as I did. We’ve shared some highlights below, together with links & a full transcript. As always, if you like what you hear/read, please leave a comment or drop us a review on your provider of choice.
— Jim
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Highlights
The Obsession Factor
Jay Yang: When you are obsessed, continuing to persist is an obvious choice because there’s nothing else in the world you’d want to do. It’s that question, ‘If you know what you want to do with your life, why are you doing anything else?’ And so obsession isn’t what you want to do. Obsession is what you can’t not do. And so a few people ask me, ‘Why did you write this book?’ It’s because I couldn’t not write about it. Every night before bed I was thinking about this idea of ‘you can just do things,’ this idea of high agency. Why do some people get what they want out of life and other people don’t? It’s more often than not the mental scripts they have running in their brain.”
Jim O’Shaughnessy: “The math is pretty simple, right? If you wait around to take your perfect shot on goal and you only make ten shots, even if you’re 80% correct, you’ve made eight goals. If, on the other hand, you take a bunch of shots on goal that you think, ‘Okay, maybe,’ you take 100. Even if you’re just half—even just half of them go in, you’ve made 50 goals.”
You Can Just Do Things
Jay Yang: “What I’ve slowly realized is that when you say ‘it’s easy for you to say,’ you’re placing your own agency onto the other person, you’re not giving yourself agency. And so the question I would ask is ‘Who wrote the mental software that’s running through your mind? And are you sure that’s what you want running in your mind?’ And so if you’re constantly thinking, ‘Oh, I can’t just do things,’ or ‘Someone else, they’re just lucky,’ or ‘Things don’t go my way’—are those really the thoughts that you want in your head? And so it’s realizing that, what if it is that simple? What if it’s as simple as realizing that you can just do things?”
The TAG Method
Jay Yang: “I think Charlie Hoehn, Tim Ferriss’s Director of Special Projects calls it the TAG method, which is step one. You want to pick a target—who do you want to work with? Who do you want to get an opportunity from? Step two would be audit. Now that you have this person, do your homework. And then step three would be gift. Give that for free, no strings attached. I think the exact line I used was like, ‘Here, I made this for you because I’ve been loving your work for the last few years. If you like it, let’s work together. If not, no harm, no foul.’ And what that does is it decreases the friction it takes for them to say yes.”
Inputs vs. Outputs
Jay Yang: “I like to think of it as inputs versus outputs. And so a lot of low agency people track the inputs. It’s like, ‘Oh, I worked hard on this. I spent ten hours on this, so I deserve to be successful. Why isn’t the world responding the way I want it to respond?’ And what I’ve observed is that high agency people focus on the outputs. Did I actually get what I wanted out of this? It’s that Naval quote: ‘The only true test of intelligence is whether you get what you want out of life.’ Low agency people think linearly. ‘I put this amount of effort hours in, I should get this amount of stuff out.’ High agency people think in exponentials.”
🤖 Machine-Generated Transcript
Jim O’Shaughnessy: Well, hello, everybody. It’s Jim O’Shaughnessy with yet another Infinite Loops. I’ve been chatting already with today’s guest, Jay Yang. Jay is a very impressive young man. We’re talking about also one of my favorite topics: high agency. The majority of people wait around, right? They wait for somebody to tap them on the shoulder or say, “Hey, you look like you’re talented. Why don’t you come and work for us?” And I think Jay and I agree about this—you can correct me later, Jay, if I’m wrong and assuming too much—but that isn’t going to get you where you want to go, especially in today’s world.
Jay, you, at age 16, cold emailed Tyler Denk, the CEO of Beehiiv. But you didn’t just say, “Hey, can we grab coffee sometime?” You actually gave him a concrete plan that led to an internship and, of course, Beehiiv 101 that’s helped hundreds of creators get more out of the platform. But you weren’t just sitting around at age 17. You sent one to Noah Kagan, a 19-page audit of his app that analyzed his email funnel. And you also included ready-to-ship assets. It reminded me very much of a friend of mine who ended up an incredibly huge success by doing a different version of that. What he did was when he would get anything in the mail—this is back in the Paleolithic era of the 1980s—when he would get a bill in the mail, he would analyze it, find everything that was wrong with it, redo it and send it to the company. And they ended up in more cases than not literally hiring him.
And kind of like you, I think your result with the email you sent to Noah was becoming head of content and leading campaigns that put the book “Million Dollar Weekend” on the New York Times bestseller list. But today, Jay, I want to talk about your book, “You Can Just Do Things: The Power of Permissionless Actions.” It’s a field guide for stacking small, bold moves until something ultimately compounds. Jay, welcome.
Jay Yang: Thanks for having me on, Jim. That was an amazing intro. Been a long-time listener of the podcast, so appreciate you having me on.
Jim O’Shaughnessy: Terrific. Well, let’s get into it, right? You’ve argued that preparation beats bravado, that speed beats depth is a real thing, and that doors that many people assume are locked actually don’t even have keys and you recommend they just try the handle. Elaborate on that for our audience.
Jay Yang: Yeah, that philosophy has been reinforced in my life. The older I get, the more I realize that a lot of the opportunities that we want in our lives aren’t handed to us. They have to be created. And if you are somebody who is naturally more ambitious than the average person, expect to take different actions than what most people take.
Jim O’Shaughnessy: One of our north stars at O’Shaughnessy Ventures and Infinite Loops is compounding knowledge. Skin in the game has to be married to actions, right? They always have to be. Because otherwise you’re just playing with yourself, right? You can sit and daydream all day long even if you’ve got great ideas. Great ideas that aren’t acted upon tend to slip away. How would you tell our listeners and viewers—don’t do that, do this. What advice would you give them?
Jay Yang: I think the biggest thing I’ve learned is not to accept the standard pace as the pace that you have to go at. I think a lot of times we grow up and it’s like you have to go to college and you have to study for four years and then you have to get an internship and then you have to get a job and then you have to put your head down and work and then, and only then will you get what you want out of your career and out of your life. And a lot of what I’ve learned is that instead of accepting that the standard pace is the only pace for you, it’s realizing there is no speed limit and it’s asking yourself, “What’s stopping me from going faster?”
It’s that question: “How can I achieve my three-year goal in the next three months?” It’s just constantly asking yourself, “Is what everyone else is telling me to do actually right for me? Or am I just listening? Am I just outsourcing my thinking to parents, teachers or society?”
Jim O’Shaughnessy: And I’ve thought a lot about that. And one of the things that I’ve concluded is all of us, myself included, are far more influenced by the reigning ideas of our era than we might like to admit. And I often think, you know, if you went back 500 years, you would be such a fish out of water. Because ideas of what’s right, what’s wrong, what’s the correct path, what isn’t the correct path, were very different back then. And so I definitely believe that it’s going to take true action and effort on the person’s part to be able to say, “You know what? For many people, yep, that traditional path makes a lot of sense. But it doesn’t make sense for me.”
I was very lucky to kind of come of age when it wasn’t like “What? You’re not going to get your graduate degree, you’re not going to get your PhD? You’re crazy, man.” When I formed my first company, O’Shaughnessy Capital Management, I was 28, 29, and this is in 1988. And I had a friend who was just like, “Wait a minute, so who are your backers?” And I’m like, “Well, I don’t really have any backers.” And he’s like “That simply isn’t done. You can’t just start your own asset management company.” And I went, “Well, I did. So we’ll have to see where that goes.”
But talk a little bit about when you say permissionless action. I know what you mean, but elaborate on it for our listeners and viewers.
Jay Yang: Yeah. Permissionless action is this idea that it’s about doing the work upfront. I always say that if you want to have an opportunity, the best way to create that opportunity is to do the work upfront. It’s to show that other person that, number one, that you want the opportunity and number two, that you can do the opportunity. And so doing the work upfront might mean doing your research on the company you want to intern for, or putting together a pitch deck with your favorite entrepreneur and dissecting his entire social and email funnel. It might be doing your research on the founder and figuring out what problems he has in his company. And so the question I always go back to is “How can I make this a no-brainer for the other person?”
I always like to say empathy is the greatest asset you can have as an entrepreneur, marketer and just human being in general. And so it’s all about reducing the friction it takes for the other person to say yes. And so when you take permissionless action, when you do the work upfront, it makes it super easy for the other person to say, “Oh, this guy knows what he’s talking about,” or “This girl, she really wants this job or she really wants this opportunity.” And so that’s what permissionless action is—it’s doing the work upfront.
Jim O’Shaughnessy: Yeah, I’m a big believer in that as well. But consider when I was still running an asset management firm. We would have candidates who were being considered for sales jobs, right? And they made it all the way through. They made it all the way through my colleagues and everything. And they didn’t ask for the job. And I kind of made that a litmus test. If you’re a salesperson and you make it all that way and then you fail to ask for the job, you haven’t done the sales job properly. And the more I thought about it, the more I think that there are these invisible societal barriers that seem to affect a lot of people. They’re like, “Oh, you know, I gotta wait until such and such or so and so,” and they make their life conditional. And I think if you make your life conditional—”I’ll be happy when,” “I’ll be a success if”—you’re probably going to be disappointed in my opinion.
I think that one of the things that appeals to me so much about your message is, and it’s right there in your title, “Hey, you can just do things.” But walk me through—have you ever had somebody who read the book and kind of took issue with you and they’re like, “Jay, well maybe you can just do things. But you know, because I’m fill in the blank, I’m this or that and these are all kind of limiting functions, I can’t do that.” What do you tell them?
Jay Yang: Yeah, I actually had a reader email me about a month ago. She was like, “You know, it’s easy for you to say, Jay. You’re a guy and you grew up in a well-off household and you’re just privileged. What about me? I’m a 45-year-old mom, I’ve got kids. I can’t just do things. I have obligations.” And I do feel for that. I think everyone starts off with different circumstances in their life. It’s that type one luck—things that are outside of your control. But things that aren’t your fault are your responsibility. And what I’ve slowly realized is that when you say “it’s easy for you to say,” you’re placing your own agency onto the other person, you’re not giving yourself agency.
And so the question I would ask is “Who wrote the mental software that’s running through your mind? And are you sure that’s what you want running in your mind?” And so if you’re constantly thinking, “Oh, I can’t just do things,” or “Someone else, they’re just lucky,” or “Things don’t go my way”—are those really the thoughts that you want in your head? And so it’s realizing that, what if it is that simple? What if it’s as simple as realizing that you can just do things?
Jim O’Shaughnessy: Yeah. The angry man lives in an angry world. The sad man lives in a sad world. The happy man lives in a happy world. And the self-talk part, I think, is incredibly important. You are essentially programming yourself. Listen to what you say to yourself and say, “If I was saying that to someone else, would they think that was a good thing for them?” The answer with a lot of these limiting beliefs is absolutely not. And yet there does seem to be this sort of pervasive attitude—I joke about often—school is their attempt to install the one correct answer machine in your head. And there are a lot more than one correct answer. Sometimes there’s no answer. Sometimes the answers are obvious.
But if I was going to give you an assignment and say, “All right, Jay, I’ve got this brilliant guy. He is incredible. She is amazing. But they just can’t get past that barrier because they think it’s rude, or they think they’re being pushy, or they think, ‘What right do I have?’” How would you coach them? How would you get them to get across that chasm?
Jay Yang: Yeah, that’s a great question. I would say it’s about starting small. There’s that quote from Alex Hormozi: “Confidence doesn’t come from shouting affirmations in the mirror, but giving yourself an undeniable stack of proof that you are who you say you are.” And so if you have these scripts that are running in your head that you don’t want and you want to change them, it’s about giving yourself evidence that you are the type of person that can just do things. You are the type of person that can do the work upfront. You are the type of person that things go your way. And so it’s doing really small things, like smiling to the barista and seeing them smile back and realizing, “Oh, I just had a positive impact on somebody.” It’s walking up to a stranger and giving them a compliment and realizing that you just did that. You just made someone’s day. And so it’s doing these small micro actions and then paying attention to them, that helps you rewire those mental beliefs.
Jim O’Shaughnessy: I think that’s great advice. I think a lot of times people that I’ve chatted with about this, people kind of start out way too big and then that often leads to failure and then they’re out. As I was saying before we started formal recording, the math is pretty simple, right? If you wait around to take your perfect shot on goal and you only make ten shots, even if you’re 80% correct, you’ve made eight goals. If on the other hand, you take a bunch of shots on goal that you think, “Okay, maybe,” you take 100. Even if you’re just half—even just half of them go in, you’ve made 50 goals.
And yet, one of the things I’m absolutely fascinated by human operating system because I, like you, agree that it’s highly reprogrammable and a lot of people don’t think that. And I sometimes just shake my head when I talk to, again, the same person that I was asking you to encourage and coach a little bit. They’re just like, “Well, yeah, that’s okay. And same thing, right?” And I look at that as, are you outer oriented or are you inner oriented? I’ve been lucky to be inner oriented for most of my life. And one of the things you see when people are outer oriented, it’s like, “Well, I didn’t succeed because—” And then they point a finger outwards, because that person was mean to me or that person just doesn’t get it or all of the excuses.
And one of the things that I decided to do early in life and I was very lucky that I decided to do it, is I took the idea “everything is my fault,” and I took it seriously. And people are like, “Well, just fault.” And I’m like, “No, by extension, success is too.” But the old adage, “Success has a million fathers, failure is an orphan.” And that’s why I said “everything is my fault,” because it really internalized for me at the end of the day, really, it is my fault. If I didn’t get—if I wasn’t persuasive enough to get that book contract or I wasn’t persuasive enough to get that person to trust me to manage their assets, that’s my fault. That’s not their fault.
Are there any other ways that you can upgrade your internal human OS, your mental models that would be able to at least soften that urge that many people have to blame others?
Jay Yang: I like to think of it as inputs versus outputs. And so a lot of low agency people track the inputs. It’s like, “Oh, I worked hard on this. I spent ten hours on this, so I deserve to be successful. Why isn’t the world responding the way I want it to respond? Because I put so much effort into it.” And what I’ve observed is that high agency people focus on the outputs. Did I actually get what I wanted out of this? It’s that Naval quote: “The only true test of intelligence is whether you get what you want out of life.” And I think when you operate with that mindset, it’s about what actually happened or the result more so than what you put in. That’s when you start to realize that everything is your fault, everything is your responsibility.
And so that simple reframe of—you are both responsible for the inputs, but more so for the outputs. Obviously, some things are outside of your control, but for the things that are, it’s like, did you do everything you possibly could to control the outputs? And the questions I like to ask myself are, “How do I increase the likelihood that this is a success? And how do I decrease the risk of failure?” And so then every decision you make, you filter that through that lens. It’s like, “Well, does knowing what you want increase or decrease the likelihood of getting what you want?” Well, probably increases it. It’s like, “Well, once you know what you want, does learning from those who have what you want increase or decrease the likelihood that you get what you want?” Well, probably increases it. It’s like, “Does getting over your limiting beliefs and taking ownership or agency over what you can control, does that increase or decrease the likelihood that you get what you want?” And you go down this list of every single decision, every single thing that goes on in your life, it’s like, “Does this increase the likelihood that I get what I want? And does it decrease the risk of failure?” And I think that simple reprogramming has played a tremendous role in how I view the world.
Jim O’Shaughnessy: Yeah. And I often say that it’s the difference between a probabilistic mindset and a deterministic one. My joke is that many of us are deterministic thinkers living in a probabilistic world. And often hilarity or tragedy ensue. And so what do you do when you’ve done all that and you’ve done the work ahead of time and you’ve minimized the chance for failure as best you can, but you fail anyway. What’s your framework for both dealing with that and then moving on?
Jay Yang: Yeah, I just chalk it up to the game. I don’t think that failure is the opposite of success. I think it’s just the road to success. I think the only true failure is failing and then quitting or giving up because you got discouraged. And so I view all failure as feedback. It’s like I didn’t get the outcome that I wanted. Well, why? How can I improve next time? And so it’s more like when you view it that way, it’s like everything is reps, everything then becomes reps. And I think you and I both are writers, you kind of view anything as something that you could potentially write about. So nothing really is a failure. It’s like if you tried something and you failed, it’s like, “Well, that’s a great story I can write about.” And it’s like you approach that with “everything works out in your favor.” And so when you have that mindset, there really is no failure unless you stop.
Jim O’Shaughnessy: Yeah. Failure is the ladder. And failures are portals of discovery and opportunity, in my opinion. Now you don’t want to keep making the same mistake. So my friend Jeremiah Lowin would call novel mistakes incredibly magical things because you’re like, “Oh, okay, what can I learn from this?” And it got me to do postmortems on the many times I failed at something I was trying to do. And it just makes you better for the next time around. Because it’s like, “This pattern looks like that one where I totally shit the bed. Maybe I’m going to approach this in a different way.”
But I think at the heart of this is our emotional regulation of how we look at the world. My son Patrick has a friend who has this great distinction. He calls people “pre-fall” or “post-fall.” And I really enjoyed that because pre-fall, that’s when you’re filled with piss and vinegar, when “my shit doesn’t stink” and blah, blah. Post-fall is you’ve gotten hammered in the face many times by reality and you’ve learned some humility and you’ve learned that you are not God’s gift to creation. And yet you continue to persevere. And we do a lot of early pre-seed type investing and I really want to find post-fall founders because they have learned a lesson that you can’t teach them. They have to experience it themselves.
And what would you say to the pre-fall guy who’s listening to this or woman who’s listening to this right now? As I just said, we can’t teach them that message, but you can maybe encourage a way of looking at the world that will make their fall hopefully a little more gentle. Maybe we’ll throw a couple of mattresses down on the floor for them rather than having them hit the concrete.
Jay Yang: Yeah, I like that frame. Pre-fall versus post-fall. I just think the only thing you can tell them is to expect it—it’s going to happen at some point. And when it does happen, realize that how you respond is what truly makes who you become. It’s like character isn’t tested when things are easy. Character’s tested when things are hard. And so it’s like right now I’m training for a marathon, and this past week I got food poisoning and it was awful. Things were coming out of every hole in my body. It was terrible. Now that I’m all better, it’s like, well, I can let that affect the rest of my training. I can say, “Oh, well, you know, there’s only 40 days left. I’ll just put it in, I’ll just show up.” Or you can see that as just another part of the process and not get too emotional about it because things like that happen, so you can expect it and then you can choose how you respond. It’s like, “Okay, I’ve missed a week. I’m going to go even harder this week to make up for it.” And so I just think it’s how you respond shows who you truly are.
Jim O’Shaughnessy: Yeah. Carl Jung has a great line, which is, “You are not what you say you will do, you are what you do.” And I really take that one to heart. Because in this era of anyone with a smartphone being able to yap online about this or that, pessimism just seems to be too easy to me. It’s much harder to be a rational optimist. It’s pretty pedestrian and simple to be able to find problems in anything. If you go looking for problems, it’s also a shitty way to program your mental model. Because if you’re only looking for the problems of a situation, guess what? You’re probably not going to try that particular thing because, “Oh, that’ll never work.”
And persistence. As I was getting ready for you, I was reminded of Calvin Coolidge, who was the 30th president of the United States. And he became incredibly famous for his maxims on persistence. And I actually jotted a couple of them down. And he’s like, “Nothing can take its place”—he’s talking about persistence. “Nothing can take its place.” And then he goes, “Talent can’t. Lots of unsuccessful people who are really talented. Genius doesn’t. Unrewarded genius is almost a proverb. Education doesn’t. The world’s filled with highly educated”—what did he call them?—”derelicts. Only persistence will lead you to what you want.” And I was thinking, that’s really true.
And as I was reading your stuff, you talk about specific individuals and it made me think of our editor-in-chief, Jimmy Soni at Infinite Books is currently working on a book, he’s tentatively titled “The Dao of Kobe.” And you’ve mentioned Kobe in regards. Also you’ve mentioned Jim Walton, the founder of Walmart. What do you think the connections—what are the underlying connections between them and others. Dyson, who just kept going. Edison, who famously said, “I’ve come up with a thousand ways to not make a light bulb.”
Jay Yang: Well, first of all, I am so beyond excited for Jimmy’s book. I’ve been obsessively studying Kobe Bryant for the last six years of my life. And so I’m definitely excited to check that book out. I think the only through line that you can confidently say about them is that they were obsessed with what they were doing. And it’s like when you are obsessed, continuing to persist is an obvious choice because there’s nothing else in the world you’d want to do. It’s that question, “If you know what you want to do with your life, why are you doing anything else?”
And so it’s like, if you know that you want to make the world’s first superpowered vacuum, or you want to be the best basketball player in the world, or you want to nail retail, it’s like, well, the only thing you can do is continue to persist. And so I think it’s that obsession. Obsession isn’t what you want to do. Obsession is what you can’t not do. And so a few people ask me, “Why did you write this book?” It’s because I couldn’t not write about it. Every night before bed I was thinking about this idea of “you can just do things,” this idea of high agency. Why do some people get what they want out of life and other people don’t? It’s more often than not the mental scripts they have running in their brain. And so that’s the through line of why are people persistent? Why are people extreme? It’s because they’re obsessed with what they’re doing.
Jim O’Shaughnessy: Yeah, obsession is a hell of a drug. And in hindsight I didn’t know it at the time, but in hindsight I was obsessed with trying to figure out why public stock markets did what they did. And I just kind of viewed it as the Olympics of business. If I can figure that out, that’s going to be really cool. And so several friends at the time were like, “Dude, what the hell are you doing going to the library on a Saturday to look up—what? You’re crazy, man. You’re obsessed.” And yet I didn’t look at it as obsession at all. I just looked at it as, “I gotta know, I got to figure this out.” And I certainly didn’t nail it. But I managed to get good enough at figuring it out to be able to start a successful business.
What about—back to Kobe though? The thing I find interesting, I’m not a sports guy. I don’t know much about sports and people make fun of me constantly for it, particularly my own children. But what really fascinates me about Kobe is he was a polymath. Most of Jimmy’s forthcoming book on the Dao of Kobe is not about sports at all. It’s about Kobe’s multitude of ideas and things that he had cooking. Do you think that’s another trait of the type of person who ends up being high agency?
Jay Yang: I think high agency people are naturally more curious about the world around them. They, because they question the visible thing that they see in front of them and want to go deeper, they naturally, I think, are more interested about other areas. And so yeah, I mean when I was studying Kobe, he was an avid writer and he got into meditation and he would go seek out the composer who did the Star Wars soundtrack. He was just—he wanted to be around other high agency, obsessive, curious people. And so yeah, I think there’s definitely a through line there.
Jim O’Shaughnessy: And I completely agree that curiosity is like magic. And by that I mean everyone that I’m working with now at O’Shaughnessy Ventures, the through line there, is that they’re all intensely curious about a lot of various things in life. And what’s interesting from my perspective as the head of the company, is that when you marry intensely curious people, but people who are intensely curious about different things, you get oftentimes this wonderful synthesis where—again, back to Jimmy. He’s not paying me to mention him continually here, but we have a fellowship program, as you know. And last October we had a gathering of people, OSV people and the fellows, and Jimmy sat with a scientist who was explaining her concept to him. And then he asked her the question that she’d never really even thought of, and it was, “Okay, so how are you going to market this?” And she kind of was like, “I hadn’t even thought of that.”
Anyway, long story short, he spent an hour and 45 minutes with her. And she found me afterwards and she said, “I just gotta say, the price of the ticket coming here, I just earned ten times that by being able to do this with Jimmy. Because she goes, “Honestly, I wasn’t even thinking about how to get other people interested in my invention here. And he kind of gave me a master class on how I could do that.”
So one of the things that I’ve learned and seen intensify is when you get these intensely curious, high action people together, the cognitive diversity can really lead to really cool things. Have you experienced that? Have you ever worked with somebody who is kind of just as obsessive and persistent and curious as you are, but in a very different area? And you’ve like, “Wow, I would have never thought of that.”
Jay Yang: Yeah, dude, all the time. I think what’s special about being online and on Twitter is there’s just so many other people who are obsessed with what they’re doing, and so it’s an insane opportunity to learn. One of the past guests you had on, Tommy Sami Potter, I went to one of his retreats as well, and that was one of my favorite things ever because there were so many other young people who were high agency and building things in completely different verticals that I was building in and just to be able to sit around in a circle and share about what we’re building and then share our problems and have everyone chime in and talk. And even aside from that, just talking to them about religion and philosophy and relationships with other people who are from all sorts of places with all sorts of different backgrounds and perspectives. I think there’s something underrated about being in a room like that.
Jim O’Shaughnessy: Yeah, I totally agree. And it just invites serendipity and increases your surface area of luck, I think, many fold. Let’s go back to permissionless action. What does that look like in the era of AI? I mean, because OSV, for example, we are an AI-first company. Everything has to have an AI workflow built into it. Because to me, I’ve been around a long while and the impact that AI will have I think is probably even greater than Gutenberg. And a lot of people just are either afraid of it, don’t get it, think it’s kind of cheating.
It’s like, for example, I’m taking a stab at writing a fictional thriller. I’ve never done that before. But am I using AI? You bet your ass I’m using AI. I was able to do what in an earlier non-AI era would have taken literally months of research. I can get done in an afternoon. Of course you’ve got to make sure it’s—you have to verify it and fact check it and do all of that. But it seems to me almost a weird obsession when I see people especially authors and “Did you write that with AI?” And you see on Twitter people saying they’re no longer going to use the em dash because AI does. To me that is so fucked up. It’s kind of like—would you have preferred that Michelangelo didn’t have paint and brushes? Would you prefer that—when radio came on the scene, symphony orchestras took out full page ads in newspapers saying how that wasn’t real music. The only way you can listen to real music is to do it live.
When I was a kid, the only thing I wanted when I was ten in 1970 was a calculator. Because back then they were just coming on the scene. And then you got this huge backlash. “You can’t use calculators in class. That’s cheating.” It’s like you often hear people say that about AI and writing. Do I take my raw chapter that I’ve written and put it into AI and ask for improvements every single time? Does that mean they’re all good? No, many of them aren’t, but they give me a jumping off point to be like, “Oh, wow, I hadn’t thought about that connection.”
Another thing I do is I’ll put them into Google’s NotebookLM and I’ll put full chapters in there and then listen to the hosts talk about them. And guess what? I have gotten more good ideas that did not occur to me by just taking the thing I wrote, putting it in there, and seeing the way that those AI hosts interpret it. I’m like, “Oh, I hadn’t even thought about that. What a great idea.”
But back to AI—models can summarize, pattern match. They can simulate expertise. How are we humans going to be able to get others to recognize, “Hey, it’s me.” In terms of, we now have limitless graduate students in our pocket whose work is pretty damn good. What advice would you give there? How are you using AI, for example? And what would you tell other young people who might be struggling with that?
Jay Yang: Yeah, well, I completely agree with you. I think I use AI, I talk to AI probably more than I talk to humans on most work days.
Jim O’Shaughnessy: Me too.
Jay Yang: And so people often will ask, “Well, if you used AI to help you write or research, is it really your stuff?” And I feel like the analogy I would counter that with is like, “Well, I use a calculator to solve this math problem. Was it me who did the math?” Does it matter? You got the outcome that you wanted to get. And so I use AI all the time. So I’m writing my second book, and so AI is currently helping me with the research process and the structuring process. And I find that it is an incredible—it’s taking the job of an entire research assistant, probably two. And so, as you mentioned, I think throughout history, humans have always been averse to change and new things. But as long as it’s humans with tools against humans with tools, it’s the humans that embrace the tools more efficiently and more effectively that will beat the humans who don’t. And so if you are a young person and you’re not using AI even just to ask silly questions and to familiarize yourself with the technology, I think you are going to be surprised by how fast you fall behind those who do embrace it.
Jim O’Shaughnessy: Yeah, again, we’re very simpatico on this because it makes me a little crazy, though, because what it is, it seems to be a philosophy that wants stasis, that wants, “You can’t use that tool.” That’s because that’s what we’re talking about here. We’re talking about tools that can help us. And it just seems so bizarre to me when people get really emotional about it and they—”That’s not real writing or that’s not real art or fill in the blank.” And it reminds me of—I was saying to a friend yesterday in conversation about this, actually talking about being excited to be able to chat with you. And it reminded me of the idea of, “Hey, we can’t—this fire thing, it’s way too dangerous. It’s way too dangerous. Man, we gotta ban that stuff because, man, is it dangerous.”
And it just seems to me that—by the way, I mentioned Gutenberg earlier, do you know how many people were opposed to the advent of the printing press? A huge number of people. Guess what? Guess who was most pissed off? The scribes. Because—but the innovation. Every tool has its positive and its negatives. And I’m not saying AI is going to be the absolute best and it will solve everything. Of course it won’t. It will hopefully lead to newer and much better problems than we had before. And yet we have this kind of kink in human OS where I’m shocked where otherwise creative people are—I was talking to one of our editors at Infinite Books and we have an AI tool that ranks, we call it the Portal, and it ranks manuscripts on a variety of categories. For us, it’s just a first pass. But one of them is an AI detector in there. And I’m like, “Why? What? Why do we even have that?” And he laughed, he goes, “Because, man, there are some people right now who, you know, they’re great thinkers, they’re great writers, but they have this thing against AI and I can’t get my head around it, just seems so limiting to me.”
It’s kind of like if you have access to a tool where you can 10x your output, use that tool. And it seems to me that it’s almost kind of a Kantian category error, in my opinion. And by that I mean it’s the ideas that I’m reading in a book or watching in a film or listening to a podcast that matter. I don’t really care who or what wrote them. They’re good ideas or they’re bad ideas or they’re just so-so ideas. But this bizarre obsession to me with the tool used—as you mentioned, you used a calculator. Does that mean I didn’t do the math? And do you think that’s just yet another of these self-limiting things that we impose on ourselves?
Jay Yang: I think it’s this idea where humans conflate things that are hard for things that are good. It’s like if I wanted to get to a far-off location, I could ride a horse or I could take a bullet train. And it’s like, does riding a horse make me a better person because it was harder? It’s like busy isn’t better. Just because you are working harder doesn’t necessarily mean that you are morally superior to everyone else. And so I just think—does using the AI tool help you get to where you want to go faster, more efficiently? Does it help you learn new things and explore new things as you’re going there? Yes. Then what is it that you’re afraid of using AI?
Jim O’Shaughnessy: I love that. And we’ll be stealing that analogy from you forthwith. You could even walk. It’s kind of like the Marxist theory of value. Which equates effort exerted should equal compensation. And I had the science fiction writer Devon Eriksen on the show and he’s got this great theory about that. And it’s like, “You know, what if you go into the sweltering Sahara desert and you spend twelve hours exhausting yourself building or digging holes in the Sahara? What am I going to pay you for that? Nothing. Because I don’t give a shit that you’re digging holes in the Sahara.” And so he equates money equals “give a shit.” And I think, I love that because it’s crass, but it gets right to the point. Like the—and you mentioned busyness. I am absolutely—drives me crazy when people are like, “Yeah, I worked fourteen hours a day and I did that for years and I deserve, I’m entitled to—” No, no you’re not. If somebody who didn’t work fourteen hours but had better output had a better thing that people gave a shit about, they’re gonna beat you.
And this busyness epidemic is just kind of crazy to me. It’s like, am I busy? Well, yeah, because I’m doing a lot of things that I want to do. But I don’t think that the time I expend writing this new fictional thriller should determine whether it has good sales or not. It’s the book that’s going to determine whether it has good sales or not. And it will have good sales if readers like it. Just seems so simple to me and conflating it with the amount of hours or—”Oh, do you know how hard I work to make this book?” By the way, writing fiction is really, really hard. I was talking to my daughter yesterday and she’s an award-winning fiction writer for middle grade fiction. And I said, “I certainly have learned that what you do is incredibly hard, but it’s also fun and taking a page from your book. I’m doing it because I want to do it. And will I fail? Okay, fine. Then maybe if I write a second fictional book, that one will do better.”
But the confusing hours put in—I call it the time punch card fallacy. We came up historically in a world where when you went to work, you had to punch your time card and then you punch out. And then you were paid for the hours that you worked. Well, that’s fine for a factory in 1905, but it isn’t the world that we live in today. And what do you say to people who have kind of—you can sense that vibe when they’re talking to you. They’re like, “Jay, you know, I love your advice. This is great, this is great work and everything. And I was highly agentic and I put all my time and effort into it, and yet I failed. So you’re wrong, Jay.”
Jay Yang: Yeah, back to what you’re saying on the busyness part. I completely agree because there’s this analogy that I—me and my analogies. But I like this analogy where it’s like if we have a competition at sea, who can chop down as many trees as possible, and you have this really sharp ax and you’re chopping the trees. And I have an army of 500 people with tractors. I will win every single time. And the answer isn’t for you to swing harder and faster. The answer is to get more leverage. And so yeah, I completely agree. Low agency people think linearly. “I put this amount of effort hours in, I should get this amount of stuff out.” High agency people think in exponentials. And I think that’s the fundamental difference.
Jim O’Shaughnessy: Yeah, again, just giving you advance warning, I am going to be stealing your best analogies. But I like that one a lot because Ken Stanley’s book “Greatness”—he’s coming on the podcast. I’m really excited to be able to talk to him because he wrote the book “Greatness Cannot Be Planned.” And what he meant by that was that it’s the things that you learn while working towards that goal that oftentimes are the eureka moment. And the broader your aperture, in other words, the more open minded you are to the idea that, “Hey, this particular version of my—let’s stay with my book. This particular version of my book might be good, but I just learned this thing over here and if I change it’s going to be much better.”
And so it’s this circuitous path of learning that if you can maintain that attitude and be persistent and be, “Yep, I’m just going to keep doing this and hope that I get a great result.” That is going to be a much better way to do things. And I agree on the exponential versus linear. What’s your attitude? Because really what we’re talking about here, if there was an overstory, it would be prefer great signal over vast amounts of noise. And you are kind of a very strong signal guy. What tips would you have for people listening or watching us to be able to have their signal be a lot higher and cut through?
Because back to AI, there’s going to be a lot of AI slop because people are just going to go, “Oh yeah, I’m just going to have the AI do it” and they’re going to put it out there. Going to be slop because they haven’t really been the architect of it themselves. They’re not using it as a research or a rewriting tool or writing helper. They’re just saying, “Yeah, write me a book about.” And guess what? That book’s probably going to be not good. But what advice would you give people who they bought in on being high agency? They’ve got great ideas, but there’s a lot of noise out there. What tips would you give them for helping their signal break through that increasing cacophony of noise?
Jay Yang: Yeah, that’s a question I’ve thought a lot about, which is in an age of AI, there’s so many mentors that you can find online, there’s so many people you can listen to. Who should you listen to? And I think a lot of people mistake someone with charisma as someone with a lot of deep insight and experience. And so the question I like to ask myself is not “Did this person achieve what I want to achieve?” But “Did this person help other people achieve what I want to achieve? And then did this person help other people like me achieve what I want to achieve? And then did this person help other people like me achieve what I want to achieve many times?” And I think that’s often a signal of who should you be listening to? Who should you seek out for insight? Not someone who’s charismatic, can speak well and tell stories, but who is someone who has gone through the fire and helped others go through the fire as well.
Jim O’Shaughnessy: That’s a great distinction. And yet again, we’re back to human OS and I’m baffled by the amount—I think doubt is uncomfortable and sometimes unpleasant, but certainty is insane. To me, somebody who believes that they have a truth with a capital T is generally somebody that is probably misguided and is probably not going to end up doing very well. And that’s not me being nihilistic and saying there are no truths. It’s me saying that you’re probably much better off in terms of doing it the way you’ve just described.
And yet, who do we elect? We elect the people who give that speech that they’re certain. Who are we charmed by? The charismatic talker who’s really wonderful at telling wonderful stories, and you just feel so good listening to them, etc. And that does seem hardwired into our human OS. What—I mean, I know you do it. How would you encourage others who really like that charismatic YouTuber or podcaster or writer to go about finding the nearest neighbor to what you’re looking for? I myself have an idea about it that does involve AI, but I’d like to hear yours.
Jay Yang: How do you go about finding that person?
Jim O’Shaughnessy: Yeah.
Jay Yang: I think it goes back to probabilistic thinking, which is—let’s say your goal is to climb Mount Everest, right? Do you find the person who is telling all these crazy stories and has—he’s really tall and he’s wearing this nice jacket and he has a crowd around him? Or do you go look at that person who’s sitting off to the side, who you can tell his calves are just really built. He’s kind of sitting off the side drinking out of a metal canteen. He’s got his big pack next to him. He looks tired, like he’s gone up the mountain several times. It’s like, who do you listen to? Do you listen to the person who you can tell is trying to put on a show, or the person who has built, has gone up the mountain several times, has taken people with him and isn’t trying to look for attention?
And I think maybe a hot take. But most of the people that you can learn the most from actually aren’t super huge on social media. They don’t have huge followings. They’re not going viral. They’re the operators who have been in the trenches and have been quietly compounding their years of experience in the dark. And so if you can find those people, I think you’ll be way better off.
Jim O’Shaughnessy: So, in other words, find Tenzing Norgay. Not Edmund Hillary. Tenzing Norgay was the Sherpa who got Hillary up to the top of Everest. And yet Hillary became the very famous one, at least in the West. Whereas Tenzing was like, “Yeah, do this every day, man.” But on that point, doesn’t that conflict a little bit with your work? Your idea that people should work in public?
Jay Yang: Yeah, I think the difference is the person who is trying to be charismatic and posture and put on a show, they’re doing it for the sake of attention. Whereas the people who build in public, the people who work in public, they’re not trying to teach things. The lens is different. When I wrote my book, I wasn’t trying to say, “Hey, I’m the guru. I’m the professor up here lecturing to the rest of you little students.” It’s more like, “You’re the guide, not the guru.” I’m that kid in the back of the class who’s taking this class before, and I’m just writing down things in my journal, and then I’m sharing. “Hey, friend to my left. Hey, friend to my right. Here’s what I—here are my notes.” It’s like, “This isn’t the way or the best way or the only way. But I took this class last year. Here’s what’s worked for me.” And so when you work in public and you document the things that are working for you, it’s more like, “Here’s how I’m doing it” more so than “Here’s how to do it.”
Jim O’Shaughnessy: I love that distinction. And if I was going to put you on the spot and say, “Hey, can you build a template right here, a repeatable playbook based on maybe we’ll just take your email breakthroughs”—is there a repeatable playbook that people obviously would modify for their own specific needs? But is there what I like to call an error pattern, a primitive pattern that is repeatable and that people listening to us right now and if you were able to generate one for them were like, “Damn, this really works”?
Jay Yang: Yeah, I would say there’s a repeatable approach to doing it. I don’t think there’s a repeatable template because the process of doing it is by definition, will be unique every time. But I think I like to call—I think Charlie Hoehn, Tim Ferriss’s Director of Special Projects calls it the TAG method, which is step one. You want to pick a target—who do you want to work with? Who do you want to get an opportunity from? And so right off the bat, I like to choose people who are one to two steps ahead of me, not on the top of the mountain. Because it’s like, “Hey, would you rather learn entrepreneurship from someone who’s currently in the trenches or someone who’s already been a billionaire, but did it decades ago and may not remember what it’s like to be a beginner right now in the current state that the world is in?”
Step two would be audit. Now that you have this person, do your homework. Can you listen to old podcasts that they went on? Can you go to Twitter and do Twitter advanced search and figure out some of their favorite thoughts or ideas? Can you Google them and then not look at what’s on the first page but go to the second page of Google or the third page? Can you go to the third page of YouTube? Can you ask people they used to work with and really try and understand who is this person, what are their goals, what problems are they facing, and then how can you help them?
And then step three would be gift. Now that you’ve done this work, you’ve done this audit. So for Noah, for example, I realized, “Hey, he has this book coming out. Well, if you want to launch a book, what do you need? You need a strong newsletter so you can reach and contact those people.” And then I was like, “Well, what do you need to have a newsletter? Well, you need to grow the newsletter. Well, how is he doing it now? Oh, he’s doing it like this and this. Well, it looks like he’s not using these social media channels and he’s using only this one. What would happen if he did this?” And then, “Well, if we did use these channels, well, what would that look like? Okay, so here’s someone else who’s been doing it. Well, here’s how we can do it for you.” And then when you do that audit, you showcase your thinking. It shows that you want the job because you’re doing the work. And then it shows that you can do the job because you’re actually thinking as if you’re already having that opportunity.
And then step three would be gift, give that for free, no strings attached. I think the exact line I used was like, “Here, I made this for you because I’ve been loving your work for the last few years. If you like it, let’s work together. If not, no harm, no foul.” And what that does is it decreases the friction it takes for them to say yes. Because when you get—I mean, I’m sure you’re on Twitter, all these people cold DMing you like, “Hey, I want to work for free or I’ll work for you or whatever,” it’s like it puts the burden on you to figure out who they are and how they can help. And so by doing the work upfront, by using the TAG method, you decrease the friction it takes for them to say yes.
Jim O’Shaughnessy: I love that idea. And we have changed the way we hire. At OSV, for example, everybody, even if we think they’re the greatest thing since sliced bread, we start everyone off as a consultant. Because one of the things that I have found is the traditional way of hiring is in my way of looking at it, kind of looking at a snapshot. Did they have a great day? Were they super on in that particular interview with you? Or what about the guy I really don’t, or woman I really don’t want to miss. They had an off day. On that particular day. They didn’t sleep well and they got into a fight with their partner and they got a ticket on the way to the interview and you’re not seeing them at their best. It can be either or. I want to watch a movie of that person. I want to see how they do over—typically we’ll give three to six month consulting arrangements.
And my newest chief of staff, that’s how he got the job. He got the job by using your idea of a gift, sending a really cool video that he made about some of the possibilities within our media franchise. And I’m like, “Huh, this is interesting.” And so we hired him for a six month period to work on that and other things. And in working with him, I found him to be just incredible and ended up offering him the position of new chief of staff. My previous chief of staff had developed into the exec on our film division. And so he moved over there to be the head of that, and now Jean-Marc is here doing that.
Why don’t more people do this? Why don’t more people just—I mean, there’s a ton. One of the reasons I started the fellowship and grant program was because I felt for almost all of human history, a genius was born, lived and died without even knowing that they were a genius without an opportunity. Because if they were in, I don’t know, Bangladesh and I was in Connecticut, unless I travel to Bangladesh, my chances of meeting that incredible innovator are virtually nil. But now we can find them everywhere. And that does necessitate being at least a little bit online. We’re not going to be able to find you if you have no online footprint.
But the idea that we can do this kind of said to me that I must do this. Because I personally think that we are at the beginning of an explosive period of innovation, creativity, etc., not only because we can now find these people, but these people we can interconnect. We can do all of those things that—if you blink your eye, that’s how long we’ve had this capability. For most of our history. And by the way, that’s one of the reasons why I think the whole idea of gatekeepers and accreditation and all of that are still very much in our psyche. Because in the old days, you couldn’t do an online search, you couldn’t do all of the things we’re able to do now. So you had something, and so went the route of accreditation and who your references were and did you make it past the gatekeepers and all that. That’s still in our cultural DNA. And I think the faster you realize that ain’t the way things work anymore, the better.
But another great way to learn, in my opinion, my friend David Senra. I’m sure you’re familiar with his podcast. The guy’s a maniac, and I love him for that. And you can learn more, in my opinion, just spending an hour with David because he did all the heavy lifting for you. It’s like, David doesn’t just—when I had him here for the first time, rather than like, “Hey, how’s it going?” and everything the first thing he did is go to my library. And then we didn’t hear anything. We didn’t hear anything from David for 25 minutes. And he came back. He’s like, “Where did you get this book?” And I love the idea that you can leverage these obsessive types like David, like you, and learn a tremendous amount from them.
But I’m reminded of one of my favorite philosophers who masqueraded as a science fiction writer, Douglas Adams, who said, “It is remarkable that the species, we humans, who have the easiest path of learning from the experience of other people, are remarkably disinclined to do so.” Is there a way to kind of break down that resistance that you found that works reasonably well?
Jay Yang: I think it’s reminding yourself of the opportunity cost of not learning from those who have come before you. It’s like the greatest people and entrepreneurs and builders and athletes and artists of all time were so amazing. Somebody wrote a book about them, and you choose not to learn from them. The greats of all time speak to you through books, and yet you choose not to listen. And I find that crazy, to be honest. There are million dollar lessons, billion dollar lessons hidden in $30 books. And I don’t see why you wouldn’t spend an hour of your time trying to learn from them so that you don’t have to go through life bumping your head against the wall trying to figure everything out by yourself.
Jim O’Shaughnessy: Yeah, you can knock on a deaf person’s door forever. And if they can’t hear you, all the knocking in the world isn’t going to get you there. Another thing that you’ve said in your work is that people don’t lack motivation, they lack clarity. Expand on that.
Jay Yang: Yeah, that was an idea I thought a lot about in my own life. I found the times where I procrastinate the most, the times where I work but not very hard or not very efficiently. It’s honestly not that I lack motivation. I’m a very driven person. It’s when I don’t really know why I’m doing something and why what I’m doing matters. And once I do understand why I’m doing what I’m doing, it makes working so much easier. It’s like hard work isn’t a prison sentence if you have a reason for working hard. And so I think that’s why, you know, principle number one, and I think chapter two in the book is identify your North Star. It’s very hard to get what you want if you don’t know what you want. And so once you know what you want, then it makes everything else clear.
It’s like, why did Kobe Bryant become one of the best basketball players of all time? It’s because he knew that’s what he wanted. And so every decision he made, he filtered through that North Star. It’s like, “Does paying attention in class help me pay attention on the court more? Yes, okay, I’m going to do that. Does practicing my pivot moves over and over again so it becomes automatic. Does that help me get there? Yes, okay, I’m going to do that.” And so for everyone, especially young people, it’s like, truly ask yourself, “What do I want my life to look like?” And not what my parents want for my life, not what my teachers or society wants for my life, but what do I actually want? And then ask yourself, “What do I not want? What are my anti-goals? What do I not want in my life?” And so when you have the north and the south, you’re able to make clear decisions. You’re able to work harder on things that you want to do that move the ball forward because you have those North Stars.
Jim O’Shaughnessy: What are your North Stars now? And interestingly to me at least, what are your southern—what you don’t want and how do you keep both of those top of mind?
Jay Yang: Yeah, my North Star, my mega North Star is a play off of Naval’s quote, which is “a fit body, a calm mind, house full of love, meaningful work, and enough wealth to not have to worry about it.” And I think those are very vague and amorphous terms on purpose. I don’t think I’ll ever fully achieve any of those things completely. But I think it’s in striving to be 1% better in each of those domains that I find the most joy. Because to me, at least in this season of my life, progress equals happiness. And so when I make progress towards those North Star goals, that’s when I feel the most sense of fulfillment and meaning. And so I try to keep that in mind pretty much every day. It’s like, what am I going after?
I want to be high energy and fit. I want to be calm and not reactive to things that happen during the day. I want to stay close with my friends and family and actually have them want to have me around and hang around with me. I want to work on things that give me joy and that I feel like are important in the world. And I want to have enough money where I don’t have to worry about what tomorrow will look like. I can—I have the freedom to then design the rest of my life to be the way I want it to be. And so then what would the anti-goals for that would be? It’s like, well, I don’t want to be fat, just always stressed with no friends or family, just in my room, just kind of alone, just in the corner, like a little gremlin. I don’t want to be working on things that I feel like are busy work or meaningless just for the sake of getting a paycheck at the end of the day. And I want to not live a life where I get to the end of it. It’s like I regret that I didn’t experience the vastness and the beauty of life, of this beautiful thing we call life.
Jim O’Shaughnessy: Those are great things to move towards and move away from. And that underlines very nicely your point about clarity. I can’t remember whose quote it is, but it’s along those lines. “You can deal with almost any what if you know why.” Viktor Frankl, is that Viktor Frankl?
Jay Yang: Yeah.
Jim O’Shaughnessy: I love—okay, so another quote of his that I love is “When we find that we cannot change a circumstance, we must change ourselves.” And I really liked that idea as well. In other words, if you know his story, the—it brings—if you’re not crying when you’re reading “Man’s Search for Meaning” at certain parts of it, you don’t have a heart because he went through horrible things during the war and yet came out the other side this amazingly inspiring human being. And because he found his why.
And I think that might even be really good advice for people listening to us and watching us right now. It’s like if you can’t immediately say what your why is, you might really want to think about that because you can get—these fitness landscapes. People oftentimes when they’re young and they haven’t had the full experience, they’re like, “Well, I want all those things, but for right now I’m going to take this job at McKinsey or one of the big consultants because I’m going to make a lot of money. And but then after I make the money, then I’m going to go and do what I really want to do.” And that very rarely happens because guess what? People forget about the path dependency. So you take that high paying job and I’m not going to just pick on consultants here. You take some high paying job that you don’t really want to do, but you’re good at it. So you take it. But then what happens? You get married or you find a life partner and maybe you have kids and well, the kids have got to go to this great school which happens to cost thousands and thousands of dollars and well, we really should join that club over there. And then all of a sudden what’s happened to you is you’ve reached the top of your fitness landscape and you’re like, “Oh, if I stop doing this and go do what I say I really love and want to do, there’s going to be a tremendous amount of collateral damage there.”
And I’ve actually seen in real life it lead to divorces and all of that type of thing. And so know your why seems like really good advice to me. And also, be calm and carry on. I think another thing of yours I read “No risk, no story.” And so I’m not saying that you should make your life so that it’s a great story. You should make it a great story for you. If you are the author of your life, and I hope you are, you should be interested in it from that point of view.
I’m also interested in when you are working in public. What has been the biggest upside that happened from that you didn’t expect?
Jay Yang: I would say getting the opportunity that I’m in right now. So I currently work at Acquisition.com and it completely caught me off guard. I wasn’t expecting it at all. And it’s been an absolute crash course in business and sales and psychology and marketing. It’s been incredible. And yeah, at the time I was running a marketing agency and it was going well and I love my clients, they love working with me and because of the stuff that I put out onto the Internet, someone on the team found me and they offered me a position and at first I was like, “Well, I kind of like what I’m doing right now.” But I ended up realizing that the fastest way to where you are is not the fastest way to get to where you want to be. So I decided to shut down the marketing agency and join Acquisition. And it’s been an incredibly fulfilling time here. And so I think there’s so many non-obvious, serendipitous things that happen when you put your work out onto the Internet. And I’ve met lifelong friends on Twitter. I’ve gotten to have incredible conversations with people like yourself. I’ve gotten—I’m waiting for that one day where I say I’ve met my wife on Twitter, but not yet. But you know, I can’t understate how much writing online has changed my life.
Jim O’Shaughnessy: Yeah, I think doing it in public, warts and all, is a great way to do it because you never know who’s watching, you never know who’s interested. And they can’t know about you if you don’t put it out there. You can’t ask until you know, you’ll never know until you ask. And if you don’t ask, if you don’t try that handle, to use your metaphor, that door has remained forever locked to you. You mentioned you’re working on a second book. Same concept or completely different?
Jay Yang: Similar. So the first book was about how do you create opportunities without waiting for permission. And the second book is, well, okay, you’ve gotten this opportunity. Well, how do you stand out within the opportunity that you have? And so it’s kind of the situation I’m going in now. It’s like I’m working at Acquisition when everyone else is great and everyone else is an A player. How do you stand out? And so that’s the big question for the next book. How do you make yourself impossible to ignore?
Jim O’Shaughnessy: I love that theme. Can you give us a hint? Just give us one way to do that so our listeners will rush out to buy the book to see all the rest of them.
Jay Yang: I will say, “Descend into hell to create heaven.”
Jim O’Shaughnessy: I love that. Yeah, so you got to be Dante and go all the way. I used to joke that I personally have a block of ice right next to Satan waiting for me in hell. That’s a great one. When do you think that book will be coming out?
Jay Yang: Not anytime soon. I think I’m taking more of my time on this one. I want to weave the stories a little bit deeper than the last book. So the last book was more for a lot of people at the time. It was for young people in college. People don’t read a lot. And so it was meant to be short, meant to be you can read it in a day, get in, get out. I think this next book, I want to be more intentional about interweaving themes a little bit better.
Jim O’Shaughnessy: Very cool. Jay, I think you are an amazing sort of North Star for a lot of people your age, at least I hope you are, because there’s never been a better time to be young and have access to all of these tools. I’m 65 years old and they excite me every day. I can’t imagine what it must be like to be your age and just think, “Holy shit, look at all the things that I get to use and play with and use as tools to get what I want.” And the thing that’s going to block you is what you’re writing about. You gotta take the plunge. You’ve got to take that first step. And I highly recommend that people of all ages read your book because it really makes its points elegantly about unless you are high agency, the world’s going to pass you by.
George Mack, the fellow that we were chatting about before formally starting the recording, he has this maxim that if you want to think or learn pretty quickly who the highest agency person you know is, think this. “If I was locked up in an emerging country or a third world prison, who would I call with my one phone call?” and he says, “That’s your highest agency friend.”
Jay Yang: I love that.
Jim O’Shaughnessy: Yeah, me too. Listen, Jay, this has been fantastic. If you’ve listened to the podcast in the past, you know that we—our final question dubs you emperor of the world for just a day. You know the ground rules. You can’t kill anyone. You can’t put anyone in a re-education camp. But what you can do is take a magical microphone that we’re going to hand you right now and you can say two things into it. And everyone on Earth whenever their morning is going to wake up that next morning and say, “You know what? Unlike all the other times when I had these great ideas when I was waking up and I failed to act on them, I am going to act on these two starting right now.” What are you going to incept in the world?
Jay Yang: I think you know what I’m going to say. But number one would be “You can just do things.” And number two would be, “Define your North Star.”
Jim O’Shaughnessy: I love both of those. And I did have kind of an intuition about what they might be. Where can people find you online? I know you’re ubiquitous, but just to make sure that everyone who has a preferred platform or whatnot, where can they find you?
Jay Yang: Yeah, I am @jayangispires on pretty much every social media. And for a little bit of my deeper thoughts, my newsletter is jayangispires.beehiiv.com.
Jim O’Shaughnessy: Perfect. I wish you the greatest success. I love seeing people like you coming up in the world. We need a lot more of you, and I hope your book helps people who are kind of teetering on the edge think, “Oh, fuck it, I’m doing it.”
Jay Yang: Well, I appreciate you having me on, Jim. This was an absolute pleasure.
Jim O’Shaughnessy: As it was for me, Jay. Take care. That was great.
Jay Yang: That was awesome. As I mentioned, long-time listener to the podcast, so it’s been an honor, truly.
Jim O’Shaughnessy: Oh, wow. Really great having you on. I love your work. I wish that there were many more of you because I think the more people like you, Jay, the better the outcomes, the better the world becomes. So keep doing what you’re doing.
Jay Yang: Thank you. I’ll certainly do my best to increase the number of those types of people out in the world.
Jim O’Shaughnessy: Terrific. All right. Good luck with the marathon.
Jay Yang: Awesome. Thank you.
Jim O’Shaughnessy: Cheers.
