Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306)
Infinite Loops
In this episode of Infinite Loops, we speak with Adam Mastroianni—experimental psychologist and sharp critic of modern culture and science. We ask, why does creativity feel like it’s fading? From endless remakes to cultural sameness, Adam argues that as society becomes more stable and risk-averse, we may be unintentionally reducing the “deviance” that drives originality and breakthrough thinking. We also discuss why science should get weirder, how to fight credentialism, and the dangers of professionalization. Important Links: To learn more about Adam Mastroianni: Adam's Piece on...
info_outline
Arkady Kulik - The Psychology of Self-Deception (Ep. 305)
Infinite Loops
In this episode of Infinite Loops, we sit down with venture capitalist and physicist Arkady Kulikov to explore the psychology behind founders, responsibility, and self-deception. Kulik discusses why the hardest problems in business are almost always human problems, how great founders deal with stress, and why the biggest lie entrepreneurs tell is often to themselves. He also explains how investors evaluate founder psychology, why difficult conversations are essential in business, and why resilience is more about adaptability than stubbornness. Important Links: Listen to our last...
info_outline
Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304)
Infinite Loops
In this episode of Infinite Loops, Jim O’Shaughnessy sits down with Angus Fletcher, Professor of Story Science at Ohio State University's Project Narrative and author of multiple books at the intersection of narrative theory, psychology, and brain science. Angus’ research challenges one of the most widely accepted ideas in modern culture: that the human brain works like a computer. Drawing on his work with U.S. Army Special Operations, he argues that humans think not in equations, but in actions and stories — and that modern education systems are failing to cultivate the...
info_outline
Jonathan Tepper - Growing Up in the Heroin Capital of Europe (Ep. 303)
Infinite Loops
In this episode of Infinite Loops, we sit down with author Jonathan Tepper to discuss his extraordinary childhood. In 1985, when Jonathan was seven, his missionary parents moved the family to San Blas — then the heroin capital of Europe — to start a drug rehabilitation center. Jonathan and his brothers grew up alongside former bank robbers, prison survivors, and people living through the AIDS epidemic. These recovering addicts became like older siblings to them. What began with one man in a small apartment grew into a global movement operating in 20 countries. Jonathan's memoir, Shooting...
info_outline
Paul Millerd & Jimmy Soni — The Creative Opportunities of a Boring Life (EP. 302)
Infinite Loops
Fresh off releasing hardcover books we’ve ever seen, Paul Millerd returns alongside Infinite Books CEO Jimmy Soni for a deep dive into the broken incentives of traditional publishing, why the industry breeds “cynicism at scale,” and how the internet is powering a second Renaissance for creators. We get into what it means to build a creative life on your own terms, the Taoist approach to growing an audience, how to navigate financial uncertainty while raising a family, and why seemingly boring daily routines fuel extraordinary creative work. I hope you enjoy this...
info_outline
Packy McCormick - How Writing Shapes Companies (Ep. 301)
Infinite Loops
Packy McCormick is one of the most thoughtful writers in tech and investing. In this episode of Infinite Loops, we talk about why writing is still the most powerful way to think clearly, how optimism becomes rational when you spend time with people actually building things, and what happens when the internet punishes you for being early and wrong. Important Links: Packy McCormick on Optimism: The Internet Contrarian: Elliot Herschberg on GitLab Founder and Cancer: Ben Thompson's Aggregation Theory:
info_outline
Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300)
Infinite Loops
What happens when you design a company assuming AI should do everything it possibly can? Jean-Marc Daecius, OSV's Chief of Staff, joins Infinite Loops to explain what it means to be “AI first” — and why he believes he may be the company's last human chief of staff. The conversation explores how AI can remove meaningless cognitive load, protect deep work, and unlock creative leverage — from reshuffling priorities and filtering email, to reinventing publishing, agriculture, education, and even how we discover books, movies, and ideas. Important links: Substack: Jean...
info_outline
John Wang - The Man Who Built The Queens Night Market (Ep. 299)
Infinite Loops
The Queens Night Market is one of New York City’s most beloved institutions — but it was never supposed to last more than a year. John Wang, founder of the Queens Night Market, joins Infinite Loops to explain how a side project with a “terrible business model” unexpectedly became one of the most celebrated food markets in the world. From leaving a traditional legal career to imposing a strict price cap in one of the most expensive cities on earth, John shares how the market evolved into a cultural institution representing more than 100 countries through food. Important links:...
info_outline
Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298)
Infinite Loops
Cliff Asness — co-founder, managing principal, and chief investment officer at AQR Capital Management — is one of the most influential quantitative investors of the last 30 years. He's also one of the most candid. In this conversation, Cliff joins Infinite Loops to talk about why losses hurt more than wins, how bubbles form, why modern investing increasingly resembles gambling, and what the dot-com era can teach us about today’s markets. Important links: Substack: Cliff's Perspectives: Cliff's X:
info_outline
Tomás Pueyo — Explaining the World Through Geography, History and Data (EP. 297)
Infinite Loops
Tomás Pueyo, the French-Spanish engineer and writer behind the successful "Uncharted Territories" Substack, joins us to dismantle the invisible forces that shape our history and future. We cover why humans are horrible at understanding exponential change, the geographical advantages of the U.S, why the Luddites might have been right, the "social media politician" of the future, why education is mostly signaling, and how air conditioning and mosquito eradication could change the destiny of nations. Important Links:
info_outlineChristine 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 retirement isn't just about hitting your "magic number," how to overcome the psychological barriers to retirement spending, why keeping your inner circle vibrant is crucial for long-term happiness, the surprising power of lifetime giving, and MUCH more.
I hope you enjoy this conversation as much as I did. 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:
- Retirement Focus: Finances or Lifestyle?
- Bring Your Kids In The Loop
- Embrace the Challenges of Social Health
- A Day in The Life of a Retiree
- Defaulting People Into Saving
- Genesis of the FIRE Movement
- Horsemen of The Investment Apocalypse
- The Delicate Balance of Investment Buckets
- Dodging A Single Point of Failure
- How to Sniff Out Fishy Financial Advice
- The Saver vs the Investor Personality Type
- Keeping Up With Mr. Market
- Annuities: The Low-Risk Underdog
- Christine as World Emperor
Books / Authors Mentioned:
- How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement; by Christine Benz
- The works of Jonathan Franzen