Anthony Pompliano — How to Live an Extraordinary Life (EP.242)
Release Date: 11/14/2024
Tommy Potter — Building the CIA for Entrepreneurs (EP.264)
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Young, polymathic, and full of energy — Tommy Potter is on a quest to build a “CIA for Entrepreneurs.” He calls it “The Power Hour” — a startup community in Michigan that hosts dropouts, undergrads and PhDs across many industries: enterprise, consumer, CPG, aviation, gaming, robotics and AR/VR, as they work together to build cool projects. I had a great time chatting with Tommy as we spoke about non-linear career paths, embracing authenticity, working with dazzling, delusional people and more! I hope you enjoy this conversation as much as I did. For the full transcript, episode...
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Alex Danco — On Strollers, Slop & Citizen Kane (EP.263)
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Shopify Product Director Alex Danco returns for his NINTH appearance on the show — and he comes in hot. As you’ll hear, I didn’t even get a chance to introduce him before he launched into his take on what everyone gets wrong about Citizen Kane. We also unpack the performance art of parenting, why dinner parties are the new status signals, the difference between meme and slop culture and MUCH more. Unsurprisingly, this was a fun one. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out...
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Vizi Andrei — The Way of the Tinkerer (EP.262)
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My guest today is my former teammate Vizi Andrei, founder of The Sovereign Artist program and author of Sovereign Artist: Meditations on Lifestyle Design. Vizi’s journey has been anything but conventional. After dabbling in various creative projects, he realized that the internet offers a unique opportunity: the freedom to take countless small risks without catastrophic consequences. He built The Sovereign Artist program to help creators step away from the toxic hustle culture and build sustainable, meaningful lives rooted in creativity, deep work, and sacred leisure. His insights into Slow...
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Barry Ritholtz — Make Fewer Errors, Make More Money (EP.261)
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My friend Barry Ritholtz has spent his career being an astute market observer, investigating behavioral finance and data analytics. He runs Ritholtz Wealth Management which has been named ETF Advisor of the Year, Financial Times Top 300 Advisors, and one of America’s fastest-growing RIAs. He’s also the host of Masters in Business, Bloomberg Radio’s most popular podcast (50+ million streams/downloads), which he started way back in 2014. In his new book, How Not To Invest, Barry emphasizes how avoiding rookie mistakes can significantly help you do better financially. He blends engaging...
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Jason Carman — Filmmaking at the Frontier (EP.260)
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The relentlessly prolific Jason Carman is making the films our culture needs: optimistic, inspiring and positioned at the frontiers of modern tech and science. In under two years, he has shipped more than 70 high-quality mini-documentaries exploring the startups shaping the future, racking up over 130,000 YouTube subscribers along the way. His new venture, Story Company, premiered “New Space”, its 100+ minute-long exploration of the modern space industry, to a packed San Francisco theater this year. Story Company has multiple projects in the pipeline, including a full-length sci-fi...
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Anne-Laure Le Cunff — Experiment Your Way to a Better Life (EP.259)
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My guest today is Anne-Laure Le Cunff, founder of Ness Labs and author of Tiny Experiments: How to Live Freely in a Goal-Obsessed World. On paper, Anne-Laure had it all: top grades, a high-flying job at Google, and a life that seemed to hit all the markers of success. But something was off. No matter how “traditionally” successful she became, she felt… “empty.” So, she decided to do something about it. A neuroscience PhD, 100,000+ newsletter subscribers, and a newly published book later, she’s developed a new model of success — one built around conducting “tiny experiments”...
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Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258)
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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)
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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)
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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)
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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...
info_outlineAnthony Pompliano — investor, entrepreneur, and media powerhouse — returns four years and 228 episodes later to discuss his new book, How To Live an Extraordinary Life, a collection of 65 heartfelt letters to his two children.
At just 36, Anthony has already invested in circa 200 companies, served in Iraq with the U.S. Army, built and sold multiple businesses, and created one of the world’s largest independent media platforms. You don’t accomplish all that without learning a thing or two, and in this episode we dig into his hard-earned insights — from the uniting traits of the world’s smartest people, to the luxury of pessimism, to why luck isn’t real.
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:
- The hidden power of “I don’t know”
- Why Anthony started writing letters to his children
- Today is practice for tomorrow
- Carve your ethics in stone, but your opinions in sand
- How bad positioning poisons decision-making
- Are there any parts of the book Anthony no longer believes in?
- What unites the smartest people in the world
- Why luck isn’t real
- The luxury of pessimism
- Power laws everywhere!
- Anthony as Emperor of the World
- MORE!
Books, Articles & Podcasts Mentioned:
- Adventures of a Bystander; by Peter F. Drucker
- The Art of Learning: An Inner Journey to Optimal Performance; by Josh Waitzkin
- How Will You Measure Your Life?: A thought-provoking approach to measuring life's success; by Clayton M. Christensen, James Allworth and Karren Dillon
- Rules for a Knight; by Ethan Hawke
- The Rise and Fall of American Growth: The U.S. Standard of Living since the Civil War; by Robert J. Gordon
- Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults; by Polina Pompliano
- Shane Parrish on the Clear Thinking podcast
- Lucky vs, Repeatable; by Morgan Housel
- What Kind of Lucky Are You?; by Jim O’Shaughnessy