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 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:

• Website
• Twitter
• LinkedIn

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

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 and development.

In this episode we discuss why Ireland should embrace techno-optimism, how to beat the NIMBY challenge with win-win solutions, why young scientists need more research funding, and MUCH more. Plus, we even touch on drone coffee deliveries (happening now in Dublin) and the things needed to unleash Ireland's entrepreneurial spirit.

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:

• Progress Ireland Website
• Twitter
• LinkedIn

Show Notes:

• The Irish GDP Boom
• The Origins of Progress Ireland
• The Path Past Bureaucratic Barriers
• Where the State Meets the Street
• How Bad Political Vibes Can Seep in
• Where the Creme De La Creme Goes in State Projects
• Innovation Amidst EU’s Strict Restrictions
• National EU Friction
• Densification Dilemmas
• Balancing Efficiency and Equity in Public Procurement
• How to Handle NIMBYs
• Pushing Past Infrastructural Comfort Zones
• Fostering Cultural Shifts
• What is Metascience?
• Recalibrating Success Metrics
• The Irish Brain Drain

Books Mentioned:

• Where the State Meets the Street by Bernardo Zacka

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:

• Rudy’s Twitter
• Rudy’s Substack

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
• Solutions to the accountability crisis
• What has happened to investigative journalism?
• Why partisanship is overstated
• Rudy as World Emperor
• MORE!

Books Mentioned:

• Yellen: The Trailblazing Economist Who Navigated an Era of Upheaval; by Jon Hilsenrath
• Deterring Democracy; by Noam Chomsky
• The Rule of Nobody: Saving America from Dead Laws and Broken Government; by Philip K. Howard

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 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:

• Digital
• Mark’s Twitter
• Mark’s LinkedIn

Show Notes:

• Why podcasts are dangerous
• Why content creators should be limited to 10 posts
• Advice is simple; life is hard
• How to find a kaleidoscopic alien
• How to win the great game
• Mania-immune investing
• Jim’s “I’m a sports guy” algorithm
• What beliefs would you die for?
• What have you unlearned in the past year?
• The fragility of morality
• Passion as a forcing function
• Movie recommendations: My Dinner With Andre & Elevator to Gallows
• Mark as World Emperor
• MORE!

Books & Articles Mentioned:

• How to Be Successful; by Jim O’Shaughnessy
• How to Win Friends and Influence People; by Dale Carnegie

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 I committed to offering him a $100k Fellowship on the spot.

But our discussion went far beyond air quality. John shared fascinating insights into the future of education—how we can reorganize it from the ground up to produce happy, healthy, and high-agency adults ready for the challenges of the 21st century.

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:

• The Corsi-Rosenthal Foundation
• John’s LinkedIn
• John’s Twitter

Show Notes:

• Nobody gets to choose the air they breathe…
• Why has air quality been overlooked?
• When Jim got stranded up a mountain
• How do you scale a K-12 solution?
• What would it cost to put a Cori-Rosenthal box in every New York classroom?
• Surprise! Welcome to the O’Shaughnessy Fellowships
• What would a model 21st-century K-12 system look like?
• How to overcome systemic inertia
• Do Charter schools work?
• Why public schools can’t mimic private school innovations
• What exciting developments are happening in edtech?
• What does public school look like in 2044?
• John as World Emperor
• MORE!

Books Mentioned:

• The Unwinding: An Inner History of the New America; by George Packer

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 is the default, 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:

• Michael’s Substack
• Twitter
• The Socratic Experience

Show Notes:

• One book a night and mental chess - a Minnesotan childhood.
• Can Socratic education scale?
• Are we entrenching a new elite?
• Why high agency is the default
• Creating new subcultures & the benefits of the Mormon model
• Experimenting our way to prosperity
• Tearing down the citadel, secret censorship & claiming the moral high ground
• Prediction markets & why we should be betting on our reputation
• The heroic tradition of reason
• Michael as World Emperor
• MORE!

Books Mentioned:

• Dr. Semmelweis vs. the World (Infinite Loops Substack)
• Ignore. Fight. Ridicule (Infinite Loops Substack)
• The Habit of Thought: From Socratic Seminars to Socratic Practice; by Michael Strong
• Be the Solution: How Entrepreneurs and Conscious Capitalists Can Solve All the World's Problems; by Michael Strong and John Mackey
• The Case Against Adolescence: Rediscovering the Adult in Every Teen; by Robert Epstein
• The Status Game: On Human Life and How to Play It; by Will Storr
• The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson
• Hierarchy in the Forest: The Evolution of Egalitarian Behavior; by Christopher Boehm
• Collective Illusions: Conformity, Complicity, and the Science of Why We Make Bad Decisions; by Todd Rose
• Can Gambling Save Science? Encouraging an Honest Consensus; by Robin Hanson
• Skin in the Game: Hidden Asymmetries in Daily Life; by Nassim Nicholas Taleb
• Hothouse Earth: An Inhabitant's Guide; by Bill McGuire
• Think in Bets: Making Smarter Decisions When You Don't Have All the Facts; by Annie Duke
• The Ultimate Resource; by Julian L. Simon
• Keep Your Identity Small; by Paul Graham

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 - he's built his empire not through traditional paths (he left his high paying private equity job), but by following his curiosity and sharing what he learns along the way. Today, we'll explore the frameworks that have helped him impact millions, why traditional definitions of success might be holding us back, and how Sahil’s relationship with time reshaped the way he thinks about wealth, wisdom, and the pursuit of a meaningful life.

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:

• Sahil’s Website
• Sahil’s Twitter
• Sahil’s Blog

Show Notes:

• The Ripple Effect of spreading good ideas
• Sahil’s Origin Story
• The Finite Impermanence of Time
• Would you trade lives with Warren Buffett?
• The Loneliness Epidemic
• The Paradox of setting Big Goals and needing Small Steps to get there
• Why waking up at 5am can rewire your brain
• Why do people chase the wrong things?
• Jim and Sahil’s Memento Mori
• Factoring in the 5 Types of Wealth when making a decision
• What makes A Wonderful Life?
• Money As a Byproduct of Pursuing Purpose
• Sahil’s Message As World Emperor

Books Mentioned:

• Zorba the Greek; by Nikos Kazantzakis
• Adventures of a Bystander; by Peter Drucker
• The Anxious Generation; by Jonathan Haidt
• Tao Te Ching; by Lao Tzu
• Collective Illusions; by Todd Rose
• The Psychology of Money; by Morgan Housel

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 basketball is due for a Moneyball moment, and why so many of us misunderstand the rags-to-riches story.

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:

• Seth’s Website
• Twitter

Show Notes:

• Author, data scientist… comedian?
• Using Code Interpreter to write a book in 30 days
• The trait that makes it incredibly easy to become an NBA player
• Why the best NBA player in history isn’t who you think it is
• Is basketball due a Moneyball moment?
• Why are so many NBA players named Chris?
• What people get wrong about the rags-to-riches story
• The hidden magic of data storytelling
• Finding your audience
• The danger of glamour
• Keep it simple, stupid
• Why the standard interview sucks
• Doppelgangers & the power of A/B testing
• The overdue revolution in health data
• Why Google should be worried
• Stated vs revealed preferences
• The power of enormous data sets
• Seth as World Emperor

Books Mentioned:

• Who Makes the NBA?: Data-Driven Answers to Basketball's Biggest Questions; by Seth Stephens-Davidowitz
• Don't Trust Your Gut: Using Data to Get What You Really Want in Life; by Seth Stephens-Davidowitz
• Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are; by Seth Stephens-Davidowitz
• What Works on Wall Street: A Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy

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 a living, evolving organism.

Julian joins me to discuss why the arc of human evolution bends towards man-made black holes, the hidden catastrophe at the heart of materialist science, the strange life of subterranean ice aliens, and MUCH more!

This was such an interesting conversation - I can’t wait for you to hear it. 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:

• Julian’s Website
• The Egg and The Rock
• Julian’s Twitter

Show Notes:

• “I just sit in my room and write”
• Why write a book in public?
• Materialism & science’s hidden catastrophe
• “The scientific method is in conflict with human nature”
• The faulty assumption at the heart of cosmology
• Big bangs, supermassive black holes & Darwinian evolution: A ~30 minute masterclass in cosmological natural selection
• “I'm predicting very, very large amounts of life in this universe”
• The strange life of subterranean ice aliens
• Could we spot man-made black holes?
• Bringing consciousness into physics
• Pulling back the curtain
• Julian as World Emperor
• MORE!

Books & Articles Mentioned:

• The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson
• Against Method: Outline of an Anarchistic Theory of Knowledge; by Paul Feyerabend
• What the Tortoise Said to Achilles; by Lewis Carroll
• The Life of the Cosmos; by Lee Smolin
• What Is Life? The Physical Aspect of the Living Cell; by Erwin Schrödinger
• Isis Unveiled: A Master-Key to the Mysteries of Ancient and Modern Science and Theology; by Helena Petrovna Blavatsky
• The Bhagavad Gita
• Did the Universe evolve?; by Lee Smolin
• The Great Filter - Are We Almost Past It?; by Robin Hanson

Ben Reinhardt is the founder of Speculative Technologies “a nonprofit industrial research lab that’s working to unlock a wonderful, abundant future through technologies that don’t have a home in other institutions.”

He has previously worked at NASA and Bay Area startups/VC firms, founded a startup building robotics for eldercare, and helped entrepreneurs start companies in Singapore. Oh, and he has a Ph.D. in space robotics from Cornell University and is one of the few people with a B.Sc. in history!

Ben, who brings his expertise in emerging technologies to the OSV advisory council, joins the show to discuss why tech people don’t do philanthropy, when to trust a credential, why there aren’t more government moonshot programs, why academia is beholden to the new, 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:

• Speculative Technologies
• Ben’s Twitter
• Ben’s LinkedIn

Show Notes:

• Speculative Technologies: the four-stage roadmap
• How early VC funding can affect incentives
• From ‘eureka!’ to getting it out into the world
• Market failure & institutional consolidation
• Where are the moonshot programs?
• The skills needed to run a research program
• Why tech people don’t do philanthropy
• Turning philanthropy into a status game
• The hidden importance of materials & manufacturing
• When to trust a credential
• Agency & American culture
• Lean ideas vs. fat ideas
• Why academia is beholden to novelty
• Ben as World Emperor
• MORE!

Books Mentioned:

• What Works on Wall Street, Fourth Edition: The Classic Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy
• The Beginning of Infinity: Explanations that Transform the World; by David Deutsch
• The Road; by Cormac McCarthy
• The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; by John D. Gartner
• The Coffee Can portfolio; by Robert G. Kirby

My guest on Infinite Loops this week knew he wanted to be an entrepreneur from the time he was buying and selling things on eBay.

Jay Reno claims he didn’t know what the word ‘arbitrage’ meant back then, but if you tug on the colourful threads of his career, you’d reveal the kind of tenacity and resourcefulness that allows special founders like him to repeatedly find value in places that have long been deserted by everybody else.

If you listen in on today’s episode, it will become apparent why O’Shaughnessy Ventures invested in Jay and his current venture. Jay is the CEO and Founder of Pointhound, which helps people find amazing deals on flights and travel using their credit card points and miles. He’s also a partner at 645 ventures.

Among other fun pursuits, he’s spent the last ten years building all sorts of cool things; like a same-day grocery delivery service, a craft coffee company, a restaurant and bar reservation app, and a furniture rental service for city dwellers.

We spent our conversation talking about his advice for first-time founders; his learnings from building Pointhound; the whimsical world of credit card point programmes; his thoughts on consumer psychology; and much more!

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:

• Jay’s Twitter
• Jay’s LinkedIn
• 645 Ventures
• Pointhound HQ

Show Notes:

• How To Bring Your Idea To Life
• The Virtues of the Y-Combinator Model
• Picking the Right Investor
• Pointhound & The Points Game
• On Consumer Psychology and Trying New Things
• Removing the Invisible Barrier
• Product Cycles and User Feedback
• Slow Down to Speed Up
• The Common Pitfalls in Building Consumer Products
• The Credit Card Prestige Factor
• The Cashback Conundrum
• The Future of Pointhound
• Jay, The Emperor of The World

Books & Articles Mentioned:

• My Inventions: The Autobiography of Nikola Tesla; by Nikola Tesla
• Mistakes were Made. (And, Yes, by Me.); by Jim O’Shaughnessy