Matthew Brightman and Alex Danco talk about technology, the future, and the present: where we think the world of tech is going, and what has it already become (but hasn't been properly articulated yet).
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Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that’s interesting!"
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For the smart, curious listener. Shows: Age of Miracles Hyperlegible Not Boring Founders Deeper Dives Anton Teaches Packy AI
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Natasha Joukovsky — On Recursion, Status Games & Manufactured Nonchalance (EP.268)
1:32:08
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1:32:08Strategy consultant turned writer Natasha Joukovsky joins me to discuss why bourgeois comfort is more conducive to writing than you think, why choice-plots make for better fiction, the eyerolling prevalence of manufactured nonchalance, our shared distaste for Atlantis Bahamas, and MUCH more! I hope you enjoy this conversation as much as I did. For …
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Tiago Forte — Unlocking the Power of the Annual Review (Ep. 267)
1:36:30
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1:36:30I’ve said before that one of the best parts of hosting Infinite Loops is the chance to connect with people who consistently make me think differently — and few do that quite like Tiago Forte. Tiago Forte joins Infinite Loops for the first time, and within minutes we closed the door on his best-selling “Building A Second Brain” and were off to the r…
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Golden Age with Mike Solana (Hyperlegible 008)
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55:17Mike Solana is the founder and Editor-in-Chief of Pirate Wires, one of my favorite publications on the whole internet and the only one I read every day. You’ll hear this about a lot of our guests, because this is why I do Hyperlegible, but Mike is one of the best writers doing it today, one of the few whose name in my inbox gives me a little dopami…
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Nir Eyal — The Psychology of Addictive Products (EP.266)
1:02:30
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1:02:30Author, speaker, founder, investor and behavioral design maestro Nir Eyal joins me for his second appearance on the show. Today, we dig into Nir’s first book, “Hooked: How to Build Habit-Forming Products.” We also discuss the difference between coercion and persuasion, AI’s use case as our personal Jiminy Cricket and MUCH more! I hope you enjoy thi…
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50 Things I've Learned Writing Construction Physics with Brian Potter (Hyperlegible 007)
1:03:35
1:03:35
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1:03:35Nobody on the internet writes about all of the complexity involved in actually building things -- from homes to jet engines -- better than Brian Potter, the author of Construction Physics. I am a huge fan of Brian's writing. I use it as a reference for a lot of my pieces. I once tweeted, "Construction Physics is a national treasure and the presiden…
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Nathan Baschez — On AI Writing, Thought Design & Solo Foundership (EP.265)
1:31:12
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1:31:12Nathan Baschez is the cofounder and CEO of Lex, an AI word-processor. He also cofounded Every, was the first employee at Substack AND co-created Product Hunt. Suffice to say, Nathan knows a thing or two about building on the internet. He joins the show to discuss how AI is changing writing, why it’s time to rethink the article, the rise of solo fou…
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Tommy Potter — Building the CIA for Entrepreneurs (EP.264)
1:45:51
1:45:51
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1:45:51Young, 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 …
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Forsaking Industrialism with Conrad Bastable (Hyperlegible 006)
1:34:45
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1:34:45In this timely conversation, Conrad Bastable joins Packy to break down his epic essay Forsaking Industrialism and explore why the West has abandoned manufacturing while China built a world-beating industrial platform over decades. Read it here for the full experience: Forsaking Industrialism Conrad has been planning this essay for months, and he co…
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Alex Danco — On Strollers, Slop & Citizen Kane (EP.263)
1:42:14
1:42:14
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1:42:14Shopify 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 diffe…
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Skittle Factory Dementia Monkey Titty Monetization with Parakeet (Hyperlegible
59:35
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59:35Pseudonymous writer Parakeet joins me to discuss her viral essay "Skittle Factory Dementia Monkey Titty Monetization." I first heard about Parakeet a couple weeks ago when I saw half of my Twitter feed and half of my Substack Notes feed sharing her essay, including a bunch of people I wouldn't expect to share an essay with "Monkey Titty" in the tit…
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Hyperlegible 004: Alex Danco, Scarcity and Abundance in 2025
1:01:59
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1:01:59On Episode 004 of Hyperlegible, I speak with Alex Danco. It was a treat. Alex is on my Mount Rushmore of internet writers. When I’m writing well, his writing has probably had an influence on mine. In this conversation, we talk about his new essay, which is an update to some of his older pieces, Scarcity and Abundance in 2025. If you want to underst…
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Vizi Andrei — The Way of the Tinkerer (EP.262)
1:20:09
1:20:09
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1:20:09My 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 risk…
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Julian Lehr, The Case Against Conversational Interfaces
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39:07In Episode 003 of Hyperlegible, host Packy McCormick talks with Julian Lehr about his recent essay The Case Against Conversational Interfaces and why natural language might not be the ideal way to interact with computers. Julian explains why conversational AI should complement rather than replace graphical user interfaces, and shares insights about…
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Hyperlegible 002: Utsav Mamoria, How to live an intellectually rich life
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41:00Utsav Mamoria recently wrote How to Live an Intellectually Rich Life on his Substack, Tumse Na Ho Paayega. It blew up, breaking out of containment in India and spanning the globe to the tune of 1,100 likes at the time of recording. For good reason: Utsav combines philosophy, mathematics, biographies, personal experience, and hand-drawn sketches to …
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Barry Ritholtz — Make Fewer Errors, Make More Money (EP.261)
1:27:53
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1:27:53My 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…
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Hyperlegible 001: Tina He, Jevons Paradox: A personal perspective
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40:20For the first episode of Hyperlegible, I talked to my friend Tina He (@fkpxls on twitter) who writes the excellent Fakepixels, which she recently brought back to life after a four year hibernation and on which she’s dropped gems each week since.Last week, Tina wrote an essay called Jevons Paradox: A personal perspective about something surprising s…
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Jason Carman — Filmmaking at the Frontier (EP.260)
1:45:39
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1:45:39The 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 …
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Anne-Laure Le Cunff — Experiment Your Way to a Better Life (EP.259)
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1:30:05My 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 f…
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Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258)
1:26:52
1:26:52
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1:26:52If 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 P…
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Ryan Delk: To Fix the School System, Build Schools
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46:56In April 2022, Packy wrote a Deep Dive on Primer: https://www.notboring.co/p/primer-the-ambitious-home-for-ambitious Three years later, a lot has changed. Primer is building schools. The opportunity is both bigger and more challenging than it was then. In this conversation, Packy and Primer CEO Ryan Delk discuss the need to fix in K-12 education. R…
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The Art of Retirement — Christine Benz (EP.257)
1:13:03
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1:13:03Christine 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 Ce…
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Luke Fehily — Ireland's Innovation Playbook (EP.256)
1:10:38
1:10:38
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1:10:38Luke 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 perspecti…
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Rudy Havenstein — How to Fix America’s Accountability Crisis (EP.255)
1:40:11
1:40:11
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1:40:11Rudy 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…
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Mark Daniel — How to Find a Kaleidoscopic Alien (EP.254)
1:26:31
1:26:31
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1:26:31Mark 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. T…
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John Kennedy — The Hidden Crisis in American Education (EP.253)
1:10:31
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1:10:31John 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 t…
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Michael Strong — Let’s Get Socratical (EP.252)
1:31:36
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1:31:36Michael 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 h…
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Sahil Bloom — A Multitude of Wealth (EP.251)
1:09:10
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1:09:10Sahil 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 …
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Seth Stephens-Davidowitz — Who Makes the NBA? (EP.250)
1:24:31
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1:24:31Seth 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. H…
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Julian Gough — The Egg and The Rock (EP.249)
1:41:48
1:41:48
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1:41:48Julian 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, T…
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Ben Reinhardt — Speculative Technologies (EP.248)
1:19:55
1:19:55
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1:19:55Ben 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 entrepr…
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