Monthly Rewind is a curated summary of the previous month's highlights at Infinite Loops HQ.
🎙️ Podcast Episodes & Deep Dives 🎙️
We hit the ground running in May with the debut Infinite Loops appearance of Ryan Holiday’s research assistant, Billy Oppenheimer.
Billy’s voracious curiosity made him an ideal fit for the show. The whole conversation is gold, but we particularly loved his & Jim’s exchange about whether everything is a remix (edited for brevity):
Jim: Because I wonder, do you think everything's a remix?
Billy: I'm a big believer in that idea.
Jim: And maybe distinctiveness emerges from you, your unique remix, right?
Billy: Yes. Yes, I think so. I was listening to Rick Rubin and he had this filmmaker on it. Rick Rubin asked him, "Could one script make 1 movie, or could it make 500 different movies?" And the guy said, "If you and I had the same exact script, we would make two different movies." And if you, Jim, and I, Billy, had that same script, we would make different movies. I think there's something about like ... And if you and I read the same book, the things we would pull out of it would be different. We're working with the same raw material, but what we find interesting and what we want to pull out and add to our remix, that's where your unique perspective, I think, comes in and allows what we think to be original work. Like Jonathan Latham, the novelist, said that if you think something is original, you just don't know the sources. And I agree with that. I think to be original is actually just to have the most obscure sources.
We sense this isn’t the last time you’ll hear Billy on Infinite Loops…
The full episode is available here. Our notes on Billy, including an easily digestible breakdown of some of his most exciting ideas, are available here.
Next, we had
, who was recommended to us by friend-of-the-show Rory Sutherland.Have you ever felt like throwing your computer out of the window after spending 45 minutes talking to a chatbot?
Sadly, interactions such as this are becoming increasingly common. John explains how we’ve ended up in this position and why it is in companies’ best interests to reintroduce humanity to the customer experience.
One of many points that resonated with us was John’s clarion call for companies to unleash their employee’s human curiosity and creativity (sound familiar…?)
The episode is available here.
Cards Against Humanity co-creator and evolutionary social scientist
joined us to share a series of deliciously 🌶️🌶️spicy🌶️🌶️ takes on happiness, morality, status games, and more.Here, for example, are David’s thoughts on morality:
David: Moralizing is bullshit. Well, I think the way that people think about morality is very wrong-headed. We tend to have very positive associations with morality, with justice, with ethics. We think that morality is all about kindness and compassion and helping and generosity and making the world a better place. But if you actually take a look at the things that humans have done throughout history in the name of morality, it is not nice at all. It is quite the opposite. In fact, morality has been the instrument of cruelty for thousands of years. It is the chief weapon in the arsenal of a warlord or a king or a politician. The best way to rally people to a violent or aggressive cause is to give them a moral reason for doing so, is to make them feel good about themselves, to make them feel virtuous, like they're the heroes waging war against the villains.
We summarised some of David’s most perspective-melting ideas in this note and this Twitter thread. You can listen to the full episode here.
In an era where belief in our societal problem-solving abilities has waned, it was refreshing to have
on the show to reaffirm his belief in human agency and our ability to shape our destiny.As well as making a compelling case for why we need to study progress, Jason drew an important distinction between Panglossian, complacent optimism and practical, solution-orientated thinking:
Jason: So that, to me, is the essence of solutionism. You might be calling out a very dire problem in stark and even alarmist sounding terms, and yet at the same time, you're looking for the best way to move forward with progress and growth.
Jason is a prolific writer, so this episode was a doozy to prepare for. Last week, we shared a post distilling around 100 of his essays into five easily digestible, thematically grouped sections. If you’re interested in learning more about progress studies, it’s a great place to start (alongside The Roots of Progress). You can find the full interview with Jason here.


Finally, we had the pleasure of hosting two BONUS episodes of the show. Firstly, we were joined by OSV Intern and Proprietor to discuss the art & craft of writing and the limits of traditional academia.
Next, we welcomed Nat & Martha Sharpe, the first recipients of an O’Shaughnessy Fellowship. They shared their radical approach to schooling and walked us through how they will use their fellowship grant to study and make documentary films showcasing alternative childhood education schools.
✍️ Essays & Articles ✍️
Demystifying Venture Capital
Back in March, we were delighted to introduce Demystifying Venture Capital, a four-part series guest-written by
(here’s episode one).The series' aim was simple: to demystify venture capitals for young and aspiring creators.
Over four essays, Grace debunked some common VC myths, shed light on the cannibalistic origins of VC (yes, you read that right), explored the rapidly changing relationship between VC and the creator economy, and finally shared six life lessons from our Glorious Leader.
Here’s Grace:
Perhaps the story of venture capital is one that persists far beyond wealthy, middle-aged white men in Patagonia vests; beyond the unhinged glamor and terror of Silicon Valley; beyond, even, the wild and unpredictable Shark Tank tirades that transfix viewers in living rooms up and down the east coast.
Perhaps the story of venture capital is as malleable as Play Doh – evolving, morphing, transforming, becoming.
Perhaps venture capital is not quite what you think.
40 AI Use Cases: How Many Did You Know About?
It’s easy to get overwhelmed by the deluge of developments in AI.
We wanted to take a step back and engage in a bit of horizon-scanning to get a sense of where, if things go right, all of this may lead (stay tuned for our upcoming episode with Chen Qiufan for more on this topic).
The essay shared 40 potential use cases in sectors ranging from education to medicine to transportation.
Here’s the full link. In the meantime, a couple of examples to whet your appetite:
3.4 Intelligent tutoring systems
AI-driven tutoring systems can provide students with real-time feedback, guidance, and support, simulating the experience of a one-on-one tutor and enhancing their learning process.
What this could mean: Affordable, accessible, personalized tutors for every child. A democratization of personalized education.
6.1 Computational Protein Design
AI can predict the three-dimensional structure of proteins, a critical step in understanding their function and designing drugs, by analyzing their amino acid sequences and simulating their folding patterns.
In biology, function follows form. By being able to design proteins in silico, we should be able to more quickly discover useful molecules.
What this could mean: A revolutionary new understanding of human biology. The opportunity to discover new ways of fighting disease.
Are You As Curious As You Think You Are?
Since
joined us as a researcher & writer, he has prepared over 40 research notes covering some of the most interesting people on the internet.What can we learn from such an eclectic range of thinkers & creators? What common themes reoccur across our guests?
In a new series, Ed is going unpack the ideas and mindsets that define our guests and, in doing so, give you the tools to unlock your creativity, broaden your perspective, and unleash your potential.
The first post of the series is available here. Here’s a sneak peek:
Abstract curiosity is going to a new country and wanting to learn about its history. It is hearing a song and wanting to learn about the genre. It is wanting to listen to the backstory of the stranger you meet on the train.
If you listen to our podcast or subscribe to this Substack, I expect you are abstractly curious. And this is great! Approaching daily life with abstract curiosity allows you to retain a childlike sense of wonder toward the world and to remain in a learning mindset where every encounter provides an opportunity for growth.
Nevertheless, I have come to learn from our guests that there exists an altogether different type of curiosity.
Not just abstract, but something more. Relentless, focused, bloodthirsty.
Not curiosity as a state of mind but curiosity as a way of life.
Not curiosity as a noun but curiosity as a verb.
I call it active curiosity.
📰 News 📰
Over April and May, we welcomed several new team members to the Infinite-Verse, including the blockbuster signing of friend-of-the-show
as Infinite Media Head-Honcho.Here’s Liberty’s announcement post and Tweet. Our favorite part:
And last but not least, there’s the media vertical — Infinite Media! — which includes one of my long-time favorite podcasts, Infinite Loops, but is growing up to become a home and friend to all kinds of talented creatives around the world and across mediums.
Books, films, newsletters, podcasts, Youtube channels… The old gatekeepers are on the way out and humanity’s creativity is being unleashed, and we want to be a part of that!
My goal at OSV is to help creators win and help audiences discover more things they love.
Jim also popped over to Liberty’s podcast to discuss his origin story and plans for OSV.
🚀 What’s Next? 🚀
June promises to be another bumper month.
Upcoming podcast guests include
, Chen Qiufan & Pippa Malmgren.Here on our Substack, you can expect a new instalment of Ed’s themes series, the triumphant return of Zanies, and more deep dives into our guests.
There may also be a few surprises along the way…
Onwards! 🚀
Thanks Ed, really enjoyed it!
Looking forward to the podcast with Prof Mollick, he is very good at experimenting with AI and thinking up creative ways to use the tools!