Philip Howard joins Infinite Loops to explain how America's legal and regulatory system became too complicated to function effectively—and how we can rebuild it around judgment, accountability, and human agency.

We discuss why government has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.

What if the great stories were more than just stories?

Jameson Olsen, host of Becoming the Main Character, joins guest host Liberty to explore fiction as a kind of operating system for life — a way to study agency, ambition, empathy, failure, courage, and change without having to live every consequence yourself. Through Hamlet, Frankenstein, Sherlock Holmes, Lord of the Rings, training montages, NPCs, and the Hero's Journey, they discuss what it means to stop drifting through life and start holding the pen of your own story. Important Links: Listen to Jameson's podcast here: https://www.becomingmain.com/

David Gelles joins guest host Jimmy Soni to discuss his career covering business for The New York Times. They talk about his books - Mindful Work, The Man Who Broke Capitalism, and Dirtbag Billionaire - and the reporting behind major stories on Bernie Madoff, Jack Welch, Boeing's 737 Max crashes, and Patagonia's Yvon Chouinard.

David explains how he broke a front-page story five weeks into journalism school, how he convinced Bernie Madoff to grant him a prison interview, and his process for writing books while working full-time. They also discuss raising kids who read for hours every day and why meditation helps him stay sane.

Important Links:

Learn more about Gretchen: https://gretchenrubin.com/

Read more of Gretchen's work: https://gretchenrubin.com/books

Listen to Gretchen's podcast: https://gretchenrubin.com/happier/

Wall Street Journal columnist Ben Cohen joins guest host Jimmy Soni, CEO of Infinite Books, to explore the hidden art of making things better. They explore the hot hand phenomenon in basketball, why Moneyball shaped a generation of journalists, the peanut butter and jelly crisis in the Warriors locker room, why ASML is the most important company you've never heard of, the strange story of Driscoll's tastiest berries, and the troubled development of The Princess Bride. Important Links: Learn more about Ben here: https://www.wsj.com/news/author/ben-cohen Read The Science of Success: https://www.wsj.com/news/types/science-of-success Read The Hot Hand: https://www.harpercollins.com/pages/hothand

AI is no longer just a tool creators use to make content faster. It is beginning to reshape the entire creator economy.

Revan Lazarus is the founder of Jamie, an AI platform for podcast networks and digital sales teams.

He joins Infinite Loops, guest-hosted by Nick Tawil, to discuss how AI is changing podcasting, media sales, audience analytics, creator monetization, brand deals, and the future of content itself. Important Links: Learn more about Jamie AI: https://www.jamie-ai.com/

In this episode of Infinite Loops, hosted by OSV's Nick Tawil, we sit down for a roundtable on the hidden global economy of secondhand textiles with Brian London, Marisa Adler, and Eric Stubin, all experts in the field. We discuss how the industry works, why fast fashion has made the problem harder, why 70% of the world uses secondhand clothing, what AI can and can't solve, and why turning an old shirt into a new shirt is still much harder than it sounds.

Substack: https://newsletter.osv.llc/

Jason Buck, founder and CIO of Mutiny Funds, joins Infinite Loops to tell the painful and darkly funny story of how the 2007–2008 crash destroyed his real estate business, wiped out his paper wealth, and taught him one of the hardest lessons in markets: being right is not the same thing as making money.

Jason explains how he went from real estate developer to volatility trader and eventually built his philosophy around survival, resilience, and the "Cockroach Portfolio." He and Jim explore why true diversification always feels uncomfortable, why human behavior is the most persistent source of market mistakes, and why investing beliefs often resemble religion. Important Links: Learn more about Mutiny Fund here: https://mutinyfund.com/ Listen to more from Jason here: https://mutinyfund.com/podcasts

Chelsea Follett joins Infinite Loops to explain why the "good old days" were far darker than most people imagine — and why progress should never be taken for granted.

Chelsea is the managing editor of Human Progress and author of Centers of Progress and the forthcoming The Grim Old Days. We discuss why humans are so drawn to nostalgia, what life was really like in the preindustrial past, why doomsday predictions keep failing, and how freedom, innovation, and open inquiry helped create the modern world. Important Links:

Learn More about Chelsea's upcoming book here: https://www.simonandschuster.com/books/The-Grim-Old-Days

Read more of Chelsea's Human Progress work here: https://humanprogress.org/authors/chelsea-follett