Dialectic 33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler I talked to @johncoogan and @jordi about making magic everyday behind the desk at TBPN. They have take the tech business world by storm over the last year with their daily news show. They are masters of daily compounding, and we talked about their chemistry, growth, influences, humor, and the "domination of spirit" that they bring to podcasting. I'm grateful to the guys for letting me crash the ultradome and flip the script on them. They do an amazing job of combining high and low: they take the work incredibly seriously and maintain an unseriousness that makes the show light, fun, and addictive. If you're curious why their meteoric rise has been anything but lucky, I think you'll enjoy this one a lot. More so, if you're wondering whether there's still a path to do something fresh in any landscape of homogeneity, John and Jordi offer the playbook. Available on all platforms below. This one was a blast. I hope you enjoy!

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12 Lessons from @johncoogan and @jordi on building TBPN: 1. You can’t copy compounding. 2. Discipline eliminates inspiration as a bottleneck. 3. Entertain, inspire or educate—Simply. 4. Go high and low at the same time. 5. Borrow laterally, not recursively. 6. Your niche is enough. 7. The show is the end, not the means. 8. Start with obsession, not opportunity. 9. Platform-Native or Bust. 10. A brand is what you feel. 11. Humor is a way in. 12. Complementary obsessions multiply.

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I talked to Chris Sacca about storytelling, risk, and playing the game of life by your own scorecard. Chris is one of the great early-stage investors ever, a massive climate and nuclear fusion investor, an incredible writer, a provocateur, a former Shark (Tank), and my old boss. Sadly for the rest of us, Chris is less public than he used to be (and tweets a lot less). I'm thrilled to share a long, winding conversation that exposes some of what I think makes him great. That's a deep-seated love of words, a rational relationship with risk that leans into rigged games, and a lifelong pursuit of authenticity. Available on all platforms and transcript all below. Please enjoy!

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Gabe Whaley and the team at MSCHF have spent a decade perfecting the art of going viral on a biweekly cadence. Now they've given up their own rule. I talked to him about how they got here, what they value, and what it will take to make mischief that lasts. You may know MSCHF by some of their viral shoes (Big Red Boots, Jesus Air Maxes) or their provocative art projects (a chopped up Damien Hirst, 999 forgeries of a Warhol and one real one, mixed together). But Gabe's most interesting creation is the factory that produced these and many others every other week for the last 7 years. I think this conversation will be especially meaningful for anyone interested in the mechanics of creativity, attention, and commerce. OR, for those interested in how the internet is changing us, our attention, and what we value. I'm eager to look back at this someday with another decade of MSCHF as hindsight. This was a special one! Avail on all platforms below, including transcript, and mintable on Zora and Pods.

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Why David Senra of Founders Podcast's #1 most listened to podcast is his own: repetition doesn’t spoil the prayer!

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16 Lessons from /dialectic Ep. 30 w/ David Senra, on creating work people still talk about in 30 years

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/dialectic Ep. 30: David Senra - The Clarity of Commitment David Senra is a podcaster and loves that title more than anyone. He hosts Founders, where he teaches the lessons of history's greatest entrepreneurs by way of the biographies he reads of them. This week, he launched a second show, David Senra, where he talks to the greatest living entrepreneurs (often about the lessons from Founders). The first episode with Spotify Founder & CEO Daniel Ek (@eldsjall) is available now. David is an enthusiast about four things: entrepreneurship, reading, history, and podcasts. His two shows are the articulation of those obsessions in a form of service for the rest of us. He is following Charlie Munger's advice: "take a simple a idea and take it seriously." David is one of the most energizing people I've ever met and has greatly inspired my work. I've had several multi-hour conversations with him that left me buzzing afterward, and I'm pleased that this is no exception. We cover many of his favorite lessons and founders, his process, biographies, focus, fear, endurance, service, and legacy. I hope you are inspired to commit yourself to something worth your days and years. All links available below.

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/dialectic Ep. 29: Billy Oppenheimer - Attuned to Clues I talked to Billy Oppenheimer about looking for clues, letting inputs guide outputs, and the daily practice of becoming. Billy is a researcher and writer who works with Ryan Holiday and Rick Rubin. I've long admired his curiosity and nose for wisdom. Talking to him is a bit like querying an encyclopedia (or LLM) of people, stories, and lessons on making process your north star, rather than outcome. Billy moves at a different pace than the terminally-online, frantic, instant-gratification culture that dominates today. Spending time with him and circle a small set of timeless truths is remarkably grounding. I hope that comes through as you listen. Please enjoy, share with or tag a friend, and subscribe to Billy's amazing newsletter, Six at 6 on Sunday. All links below.

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/dialectic Ep. 28: Maxwell Meyer - Starships & Road Trips 17 Lessons from my conversation about progress, America, capitalism, and more with Max Meyer of Arena Magazine: 1. America’s lodestar is the Declaration of Independence. The founding myth (all men are created equal…) it represents is unique in history, and upstream of everything else. 2. Risk tolerance is an American advantage. Silicon Valley lets people fail hard and come back again, and that spirit is worth defending. 3. The pendulum swings. Alleged one-way trends (political cycles, birth rates, concentration of power, etc) turn out not to be true as most things tend to be cyclical. We, like many who came before, can be prisoners of the moment. 4. Be careful with cliché. Clichés are the lowest hanging fruit when telling stories. The modern media loves them, but describing things as they are is much more important. 5. Markets make us better. The number one rule of capitalism is: you can’t kill your counterparty. This forces you to negotiate instead. 6. We need markets most for basic needs. Many tend to invert this, thinking: capitalism is fine for luxury sports cars, but we need to regulate grocery prices. 7. Good writing is fundamentally good description. Good writing paired with a good reader is two people thinking, even though they've never met one another. 8. Americans are movers. Everyone in America left somewhere for somewhere else within the memory of 10-20 generations. 9. You can't claim to love America if you hate half of the country. Both sides need a lot of humility here. 10. Progress requires dialectic (😏). You need to go back and forth between ideas to move forward, and most important is taking the other side’s premises seriously. 11. Progress is fragile. Growth and abundance, when taken for granted, can lead to regression. Strong times create weak men… 12. It’s easy to overestimate individual leverage. Elon spent millions on a Wisconsin election to no avail. The FBI director may in fact be more powerful than Sam Altman. 13. When being optimistic, be specific. Focusing on the things that are already happening is good way to make people optimistic about the future, rather than promising things that are difficult to falsify, concretize, or are abstract. 14. Pursuing quality leads to universal luxuries. Quality goods make everyone richer because they're made to last. In a sense, they turn everyone into an aristocrat. 15. Remember the back half of the brain. There's a constant push and pull between the rational and irrational parts of your brain. Don’t forget the quieter, “irrational” side. It is wise. 16. Don’t forget the places between places. The most underreported American story is the quiet prosperity of small, uncelebrated American towns. 17. American beauty, big and small. America is great because of our wild ambitions — rockets and markets and science — and because of the huge, little lives that everyday people live. Full episode transcript and links below.

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Dialectic Ep. 27: Mackenzie Burnett - Accounting for America I talked to Mackenzie Burnett about building financial tools for the independent businesses of America's heartland. Mackenzie is the template of a deeply serious, strategic, and tactical entrepreneur whose engine is not purely ambition, but purpose. Hearing her talk about the big and small of her work is infectious. With Ambrook, Mackenzie is focused on enabling the American Dream and by way of bottom-up resilience. She calls it Grassroots American Dynamism. She combines a rare combination of knowledge across technology, agriculture, policy, and finance that has shaped Ambrook's ability to deliver great financial software for underserved customers, starting with farmers and ranchers. Highlights: - the government's complexity: we treat it like a black box that is either fully incompetent or fully trusted; in fact it is many individuals--mostly non-political appointees--responding to incentives - pragmatic environmentalism: meet people where they are with outcomes rather than ideology - language matters: “resilience” travels further than “sustainability” - "biological factories": why farms are deceptively complex businesses - "everything goes back to accounting": Wading into complexity is freeing: it enables long-term thinking, better decision-making, and lower anxiety - make the intractable tractable: the CEO’s job is to ingest lots of information and turn messy problems into solvable ones - explore with niche entry points: generalized explanations or histories can be appealing, but specificity can be more meaningful (like understanding Italy by way of citrus) - physical design systems: why aesthetics and spaces matter Transcript and all links: https://dialectic.fm/mackenzie-burnett Video, podcast, Zora, Pods links below.

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I talked to Cyan Banister about her unique approach to living with childlike wonder in a world of sleepwalking adults. Cyan lives a singular life. She's radically accountable and optimistic despite teenage homelessness, adores other people despite feeling like an alien, and is a world-class investor (in SpaceX, Uber, DeepMind, etc) despite believing more in magic than datarooms. Cyan has told her incredible story in remarkable fashion in a few places, so I decided to simply talk to her about her philosophy for finding wonder in the world. It can be summed up, in her words, as something approximating what the French call dérive, or an intentional drift. Cyan is never bored, always curious, and enamored as much by her inner world as the richness of the outer one(s). Highlights: - "like moths to flame": in the words of her husband Scott, people are attracted to Cyan because everyone wants their childhood back - find ways to put on "magic glasses": see the world in unexpected ways and you'll be amazed what you find - true conviction is rare: when Peter Thiel has to make an exception to a rule at FF for you, you know you're operating at a different level of conviction - collect rare minds: when you meet special people, they wide your perspective and you can mentally ask yourself how they'd view a situation - "everything is my fault": radical accountability changes every situation, and making your bed in the morning is a love letter to your future self - "it is happy": what happens when you observe your thoughts with detachment -- not "I am happy," but "it is happy"? - "it just doesn't matter": why Bill Murray's famous line isn't about nihilism at all, but quite the opposite--it helps us orient to what does matter Full transcript and all links available here and below: https://dialectic.fm/cyan-banister

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I talked to Reggie James (@hipcityreg) about his unique influences and belief that technology is a mirror that reflects and evolves with us -- for /dialectic's first live episode! Reggie combines a unique set of references and inspirations to bring a fresh perspective to philosophy, design, and discussions in the world of technology. From Naoto Fukasawa to Marshall McLuhan to Kevin Kelly, to name a few. This plays a critical role in his design process and creative thinking, whether that was applied to his recently acquired startup Eternal, his prolific writing, his recent book Hardware 2024, his community organization with Terminal NYC, and more. @fwb Fest is a special place for me, and this time I had the privilege to do an episode of Dialectic on stage. Reggie was an obvious fit: he captures so much of what makes Fest special: culture, technology, crypto, philosophy, history, design, art... I hope you enjoy the conversation. A few highlights: - design affordances across hardware and software, and what it means for a technology object to be opinionated - how hardware eras shape our software cultures - "de-fanging loaded technologies" - how all technologies are a mirror - imaging more universal luxuries like the iPhone - how friction creates meaning - Reggie's views on personal and American myth All links below, including transcript.

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I talked to Linus Lee about how technology and software might enable "instruments for superagency," amplifying our humanity rather than diminishing us. Linus's stated mission is using software to help us become clearer thinkers and more prolific dreamers. Today, he builds and explores how AI can enable the the teams at Thrive Capital. Over the years, he's built over 100 personal projects, while researching and building across roles at Notion, Betaworks, and Replit. Highlights: - how interfaces can be more like turn-by-turn nav or maps, trading-off ends and means - why great tools abstract and introduce complexity - why long-division on paper might point us to new thinking tools - why there's "no true generality" with LLMs, even if we convince ourselves otherwise - mapping the latent space of what we mean when we say people are "smart" or "cracked" or "spiky" - what it looks like to bring an engineering mindset to systems, products, and teams - building an "iron man suit" for the team at Thrive - dream, beauty, and wonder as the engine of our technological exploration Available on all platforms, including transcript: https://dialectic.fm/linus-lee

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Switzerland's trains have no gate fares; you just walk on and sit down. Japan's reality show "Old Enough!" features toddlers as young as two running errands alone through busy cities. Both work because of invisible shared social scripts that create trust between strangers. Americans often dismiss these as "surface-level politeness." But those "meaningless" rituals do a lot of heavy lifting. Take small talk, for example, a topic Tamara Winter says she’s the “strongest soldier” of: "When I'm doing small talk in business, I'm trying to see if you know how to read social cues. I'm trying to see what appropriate disclosure looks like when you're just meeting people. And beyond that, I'm trying to see if you're the kind of person I want to be around for extended periods of time." Scale this up to the societal level, and you get what Charlie Munger called “a seamless web of deserved trust." Small, seemingly insignificant soft details are the seeds of a much more robust, hard scaffolding that produces safe, thriving societies. When strangers can reliably signal goodwill, consideration, or trust, entire systems work differently. You get the bookstore owner in Montecito who told Tammy, "Just mail me a check" when she forgot her wallet. Switzerland's honor-system transit. Japan's kids navigating cities solo. Conversely, when these scripts break down, life gets high-friction fast: plexiglass on toothpaste in your local CVS, private security, gated communities. Trust becomes a luxury good available only in curated enclaves. It’s not hard to imagine the path to the physical world of Stevenson’s Snow Crash. When norms hold, you get the freedom to move through the world without negotiating every interaction. The “pointless” rituals aren't pointless. They're the foundation that lets strangers become collaborators. In our latest Dialectic conversation, Tammy talks more about rebuilding these types of societal substrates with intention. All links and transcript available below:

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Excited to do the first /dialectic episode in front of an audience at @fwb Fest 2025, this weekend in Idyllwild. Fest has been home to some favorite talks I've heard over the years. I hope to follow in that legacy. Should be a fun conversation with a special guest!

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