This article is taken from the second issue of OSV Quarterly, your definitive source for thought-provoking articles from the OSV brain trust, comprehensive updates on our verticals, exclusive editorial insights from Jim, guest posts from friends of OSV, and more.
The second issue of the magazine launched this week and is available (for free) here. Featured articles include a deep dive into the future of work, a masterclass from Jim on transforming ideas into execution, a guest essay from friend-of-the-show Luke Burgis, and much more!
Jim has long been a student of complex adaptive systems: bottom-up phenomena that continually adapt and evolve in response to changing conditions.
A predominant trait of such systems is their aversion to top-down control. Try to introduce arbitrary order, and you risk messing with the magic. Leave them to blossom, and you encounter emergence: the spontaneous creation of a complex and unpredictable ‘system’ or ‘order’ that makes apparent sense retrospectively.
One thing that you could never accuse Infinite Loops of is being subject to any arbitrary top-down structure. For over four years, our interviews have been selected and conducted, not according to any monetary or growth metric, but simply pursuant to Jim’s unbridled, chaotic curiosity. As the man himself likes to say, our episodes are nothing other than a series of conversations he would be having anyway; just this time, he left the recorder on.
We recently celebrated our 200th episode. An opportune moment, then, to look over our now comprehensive dataset (over 250 hours of conversations) and reflect on some of the themes that have emerged over time.
Even a cursory glance over our episodes shows that, like any complex system worth its salt, an order has emerged from the chaos. Over the years, several groups of implicitly linked episodes have materialized — as if by design. Let’s explore some favorites.
The Hunt For the Frontier
Prepare to have your perspective melted by our miniseries of episodes exploring the medicinal, psychotherapeutic, and scientific frontier. What started with Jay Sanguinetti, whose work explores the collision of Eastern philosophy and Western science, has since visited ayahuasca retreats in the Sacred Valley of Peru, explored the collapsing boundary between the mind and the body, confronted the myths and misconceptions around hypnosis, and, most recently, explored the implications of morphic resonance and the extended mind.
The Infinite Loops Leadership Academy
Populated primarily by an Avengers line-up of female leaders and founders, including Dr. Pippa Malmgren, Julie Fredrickson, Dr. Julie Gurner, and Jacqueline Novogratz, the Infinite Loops Leadership Academy presents a series of deep dives into the art and science of leadership in the modern era; from the death of the specialist leader to the benefits of being unreasonable.
The Weird World of Alex Danco
Alex Danco’s episodes are complex adaptive systems in themselves. Seven episodes in, a strikingly cohesive narrative has emerged (despite Alex and Jim’s failure ever to discuss anything they planned in advance.) Come for the chaotic energy; stay for the masterclass in worldbuilding and social hierarchies.
Get Dichotomous
A series of episodes exploring, in different ways, the dichotomy between rationalism and what lies beyond: narrative, myth, meaning. Friend-of-the- show Tom Morgan’s episodes are this theme’s flag bearer, but it has cropped up elsewhere, from Herbert Lui’s distinction of the Madman and the Judge to Edward Slingerland’s exploration of Ancient Chinese philosophies of effortless action.
Creator Economy 101
For those of you trying to navigate the nebulous and fuzzy world of the creator economy, it can be nearly impossible to decipher nuggets of actionable signals from the deluge of noise. We’ve got you covered. This rich seam of episodes features creators at all stages of their journey – Danny Miranda, Kyla Scanlon, Jack Butcher, Eric Jorgenson, Jack Raines, and more – walking you through not only how to survive as a creator, but how to thrive.
How to Upgrade Your HumanOS
We do not have to live with the programming we were born with. Through hard work and persistence, it is possible to fundamentally change how we perceive and interact with the world. By understanding the status games we’re all playing, the stubborn grip of mimesis, the true meaning of happiness, the simple but superpowered truth of ergodicity, and more, we can begin to gather the tools we need to tinker with and upgrade our humanOS.
Progress! Progress! Progress!
Where does progress come from? How is it achieved? Why should we care about it? These questions and more have driven a series of episodes with experts in the field of progress, from Jason Crawford to James Pethokoukis. The goal? To better equip ourselves to navigate and maximize the unlimited opportunities of the Great Reshuffle.
These examples are just the beginning. Dig into the archives and you can find writing masterclasses, founder lessons, creativity secrets, odes to storytelling, and much more. Some episodes are easily labelled, some defy definition. The fun comes not from categorizing but from connecting — finding the ideas that recur regardless of discipline or domain.
Can we extrapolate anything from these mini-series? Is there a meta set of themes lurking underneath the surface?
Here, we return to where we started. More than anything else, Infinite Loops is an extension of Jim’s brain. What lies beneath isn’t so much a set of easily definable themes as a set of outlooks: open-mindedness, creativity, optimism, future focus, playfulness, and, of course, curiosity.
For (much) more, check out the second issue of OSV Quarterly here. Like what you see? Anything you’d like to see included in the next issue? Let us know in the comments!