Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258)
Infinite Loops
If you’ve heard me speak for more than five minutes you’ve probably caught me dropping a Robert Anton Wilson reference (or several). Wilson is one of the most interesting (and underappreciated) writers I’ve ever come across — a Nostradamus for modern times. I was delighted to sit down with Gabriel Kennedy, author of the excellent biography Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson. I could talk about this stuff for days, and we had a blast discussing Wilson’s ideas, influence and impact. Consider it a beginner’s guide to avoiding cosmic schmuckery. I hope...
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The Art of Retirement — Christine Benz (EP.257)
Infinite Loops
Christine Benz is the Director of Personal Finance and Retirement Planning at Morningstar, where she has spent over three decades helping investors navigate the complexities of financial planning. She is also the author of "How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement" and serves as the president of the John C. Bogle Center for Financial Literacy. Before focusing on retirement planning, Christine worked as a fund analyst, bringing a unique perspective that combines deep investment knowledge with practical financial wisdom. Christine joins the show to discuss why...
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Luke Fehily — Ireland's Innovation Playbook (EP.256)
Infinite Loops
Luke Fehily is the Director of Innovation Policy at Progress Ireland — an independent think tank backed by the likes of the Collison brothers — that’s on a mission to connect Ireland to proven policy solutions from around the world. Before joining Progress Ireland, Luke cut his teeth in both public and private sectors, developing a unique perspective on how to navigate bureaucratic challenges while maintaining ambitious visions for change. His current work spans housing, infrastructure, and innovation policy, with a particular emphasis on meta-scientific approaches to research funding...
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Rudy Havenstein — How to Fix America’s Accountability Crisis (EP.255)
Infinite Loops
Rudy Havenstein is a writer and satirist known for his sharp critiques of America’s sprawling institutions and the elites who run them. He joins the show to discuss the accountability crisis in America — how it manifests across political life and, most importantly, what we can do to fix it. Important Links: Show Notes: Why we should fear hyperinflation “The Fed is Congress’ drug dealer” The Great Financial Crash & America’s accountability crisis How to disagree agreeably How democracy REALLY works Why we should bring back Glass-Steagall The problem of cluelessness...
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Mark Daniel — How to Find a Kaleidoscopic Alien (EP.254)
Infinite Loops
Mark Daniel is the co-founder and managing partner of the investment firm Digital, whose portfolio extends across accelerated computing, gaming, crypto, social networking, AI, extended reality, cybersecurity, creator tools, spatial computing, and immersive learning. Back in 2013, he was also one of the very first recipients of a Thiel Fellowship. This was a fun one. Mark joins the show to discuss why podcasts are dangerous (😬), why content creators should have a 10 post limit, how he identifies kaleidoscopic aliens to invest in, and MUCH more. I hope you enjoy this conversation as much as I...
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John Kennedy — The Hidden Crisis in American Education (EP.253)
Infinite Loops
John Kennedy, a director at the Corsi-Rosenthal Foundation, is tackling an overlooked crisis in American education: air quality. With the ingenious use of a simple $60 box fan, he's on a mission to revolutionize the health and learning environments of students nationwide. It's mind-boggling how much low-hanging fruit there is here. The difference that clean air makes to health and brain capacity is enormous, and it's a surprisingly cheap problem to fix. In fact, as you'll hear about halfway through our conversation, I was so convinced by John and the Corsi-Rosenthal team's solution that...
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Michael Strong — Let’s Get Socratical (EP.252)
Infinite Loops
Michael Strong has spent decades quietly revolutionizing education by designing innovative schools and programs built around agency, critical thinking, entrepreneurship and creativity. He is the founder and CEO of The Socratic Experience, a virtual school that equips students for lifelong happiness and success through Socratic dialogue. Alongside his work in the US, he has educational consulting experience in multiple developing nations. And… he’s a fellow Minnesotan! Michael joins the show to discuss whether Socratic education can scale, the benefits of the Mormon model, why high agency...
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Sahil Bloom — A Multitude of Wealth (EP.251)
Infinite Loops
Sahil Bloom, a prolific creator, founder and investor, has mastered the art of translating complex ideas about wealth and success into wisdom that resonates with millions. His newsletter, The Curiosity Chronicle, grew from just 100 readers to over 800,000 subscribers in three years - a testament to his ability to cut through the noise with clarity and insight. His upcoming book, "The 5 Types of Wealth," challenges our conventional understanding of what it means to be truly wealthy, arguing that financial success is just one piece of a much larger puzzle. Here's what makes Sahil fascinating -...
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Seth Stephens-Davidowitz — Who Makes the NBA? (EP.250)
Infinite Loops
Seth Stephens-Davidowitz, a data scientist and bestselling author, is known for his brilliant use of data to upend conventional wisdom - often with humorous, surprising, and occasionally shocking results. His latest book, Who Makes the NBA, uses data to interrogate some of basketball’s biggest questions, consistently yielding unexpected insights. Here’s the kicker - he wrote the entire book in just 30 days after discovering Code Interpreter. Unsurprisingly for a former quant, I had a blast chatting to Seth. Topics discussed include why so many NBA players are called Chris, whether...
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Julian Gough — The Egg and The Rock (EP.249)
Infinite Loops
Julian Gough sums up his career as follows: “I just sit in my room and write.” Well, I think being an acclaimed children’s author, novelist, stage playwright, poet and top-ten Irish musician is a little more impressive than he’s letting on… Oh, and I didn’t even mention that he wrote the ending to the computer game Minecraft! His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the universe, arguing that is not some random, dead, purposeless sack of chemicals, but instead...
info_outline“Ignoring what is obvious incurs a huge cost.
It requires you to go about your day numbing yourself to the reality of who you are and what you want—which is a waste of time for you and everyone around you.
By contrast, admitting what is obvious is freeing and motivating. But it’s terrifying to do it. Sometimes the most obvious truths about ourselves are hard to see because the consequences of those truths seem so dire.”
Those are the opening lines of one of my favourite essays I’ve read in the last year, written by this week’s guest on Infinite Loops - Dan Shipper.
Dan is the Co-founder and CEO of Every, a media company that wants to be an intellectual lighthouse amidst the tempest that is the Age of AI.
Every began life in 2020 as a bundle of digital newsletters (almost like a centralised version of Substack with more of an editorial flourish). These days, it’s blossomed into an ecosystem of colourful newsletters, podcasts, courses, and software products, all oriented around the unpacking of a single question - “What comes next?”
Every is already one of my go-to destinations for all things interesting. It’s less brain food than brain buffet (the kind of buffet that serves fresh blueberry pancakes with real maple syrup).
In our conversation, Dan shares his thoughts on everything from AI companions; his approach to erecting the Every ‘Pyramid’; his playbook for building new media companies; the idea of LLMs as mirrors for humanity; and using content to ‘find your people’.
What I love about him is how candidly and thoughtfully he talks about his journey to discover his own truth. His realisation that he didn’t need to hang up his boots as a writer in order to become a founder is something that particularly hit home for me.
Dan Shipper is also my underdog pick to eventually wrest the title of Infinite Loops Emperor from reigning clubhouse leader Alex Danco. By which I mean to say, this is most certainly not the last time Dan joins us on the show, so you may as well get to know him better.
For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.
Important Links:
Show Notes:
- Dan’s Superhero Origin Story
- Writers as Founders
- What Would You Pay To Do?
- The Every Pyramid
- The New Media Playbook
- How To Find Your People
- Our AI Mirrors
- From Explanation Problems to Engineering Problems
- On Intuition
- From The Knowledge Economy To The Allocation Economy
- The Reluctance To AI Adoption
- AI Companions
- Dan, The Emperor of The World
Books and Articles Mentioned:
- Admitting What Is Obvious; by Dan Shipper
- *The Global Brain: The Evolution of Mass Mind from the Big Bang to the 21st Century; by* Howard Bloom
- Against Explanations; by Dan Shipper
- The Trial of Socrates; by I. F. Stone
- The WEIRDest People in the World; by ****Joseph Heinrich
- The Three Musketeers; by Alexandre Dumas