AI & I

Dan Shipper
  • 4.9 (29)
  • TECHNOLOGY
  • UPDATED SEMIWEEKLY

Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the show. Join us to discover how AI is changing how we think about our world—and ourselves. For more essays, interviews, and experiments at the forefront of AI: https://every.to/chain-of-thought?sort=newest.

  1. 1D AGO

    Best of the Pod: Reid Hoffman on How AI Is Answering Our Biggest Questions

    Learn how to use philosophy to run your business more effectively.Reid Hoffman thinks a masters in philosophy will help you run your business better than an MBA. Reid is a founder, investor, podcaster, and author. But before he did any of these things, he studied philosophy—and it changed the way he thinks. Studying philosophy trains you to think deeply about truth, human nature, and the meaning of life. It helps you see the big picture and reason through complex problems—invaluable skills for founders grappling with existential questions about their business. I usually bring guests onto my podcast to discuss the actionable ways in which people have incorporated ChatGPT into their lives. But this episode is different.  I sat down with Reid to tackle a deeper question: How is AI changing what it means to be human?  It was honestly one of the most meaningful shows I’ve recorded yet. We dive into:- How philosophy prepares you to be a better founder- The importance of interdisciplinary thinking- Essentialism v. nominalism in the context of AI- How language models are evolving to be more “essentialist”- The co-evolution of humans and technology  Reid also shares actionable uses of ChatGPT for people who want to think more clearly, like:- Input your argument and ask ChatGPT for alternative perspectives- Generate custom explanations of complex ideas- Leverage ChatGPT as an on-demand research assistant This episode is a must-watch for anyone curious about some of the bigger questions prompted by the rapid development of AI. If you found this episode interesting, please like, subscribe, comment, and share!  Want even more?Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper  Ready to build a site that looks hand-coded—without hiring a developer? Launch your site for free at framer.com, and use code DAN to get your first month of Pro on the house! Timestamps:00:00:00 - START 00:04:35 - Why philosophy will make you a better founder00:08:22 - The fundamental problem with “trolley problems”00:14:27 - How AI is changing the essentialism v. nominalism debate00:29:33 - Why embeddings align with nominalism00:34:26 - How LLMs are being trained to reason better00:44:52 - How technology changes the way we see ourselves and the world around us00:46:24 - Why most psychology literature is wrong00:52:46 - Why philosophers didn’t come up with AI00:56:30 - How to use ChatGPT to be more philosophically inclined Links to resources mentioned in the episode:Reid Hoffman: https://twitter.com/reidhoffmanThe podcasts that Reid hosts: Possible (possible.fm) and Masters of Scale (https://mastersofscale.com/)Reid’s book: Impromptu https://www.impromptubook.com/The book Reid recommends if you want to be more philosophically inclined: Gödel, Escher, Bach https://www.amazon.com/G%C3%B6del-Escher-Bach-Eternal-Golden/dp/0465026567Reid’s article in the Atlantic: "Technology Makes Us More Human" https://www.theatlantic.com/ideas/archive/2023/01/chatgpt-ai-technology-techo-humanism-reid-hoffman/672872/The book about why psychology literature is wrong: The WEIRDest People in the World by Joseph Henrich https://www.amazon.com/WEIRDest-People-World-Psychologically-Particularly/dp/0374173222The book about how culture is driving human evolution: The Secrets of Our Success by Joseph Henrich https://press.princeton.edu/books/paperback/9780691178431/the-secret-of-our-success

    1h 1m

  2. DEC 16

    Attaining A Jhana Live: How Anyone Can Achieve Super Wellbeing

    We recorded someone guide himself into a Jhana live on our podcast. And he narrated the whole process from start to finish. Jhanas are meditative bliss states and they traditionally require thousands of hours of practice. But Stephen Zerfas and his team at Jhourney are changing that—creating retreats where most participants hit a Jhana in their first week. Dan Shipper went to one of their retreats earlier this year, and it was by far the best he’s been to. So we had Stephen on AI & I to show us how he gets into a Jhana and what the future of super wellbeing might look like. If you found this episode interesting, please like, subscribe, comment, and share! Want even more? Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipperTimestamps: Introduction: 00:00:56 A primer on Jhana meditation: 00:01:18 Zerfas guides himself into a Jhana: 00:05:47 Why Jhana is about resting into what already exists: 00:36:04 Approaching meditation with play and curiosity: 00:39:30 The potential pitfalls of Jhana meditation: 00:45:04 How to hack your personality through memory reconsolidation: 00:48:21 Why Jhana won't let you numb yourself to real problems: 00:53:10 How Jhana meditation has changed Zerfas: 00:55:36 How Jhourney is using AI to make Jhanas more accessible: 01:09:41 Links to resources mentioned in the episode: Stephen Zerfas: Stephen ZerfasJhourney: https://www.jhourney.io/The Donella Meadows book Zerfas refers to: Thinking in Systems: A Primer

    1h 16m

  3. DEC 10

    She Turned Her Whole Life Into Training Data—For an AI Baby

    Sarah Rose Siskind is incubating two types of intelligence at once: her unborn child, and FetusGPT—an LLM trained on nothing but what she hears and says throughout the day. This includes Seinfeld episodes, YouTube videos about lemurs, eight hours of snoring per night—and even conversations with me, all condensed into MP3 and text files that are used to train the AI. Since FetusGPT is learning English from such a narrow, idiosyncratic slice of the world, it mostly babbles right now, and if she swears, it picks that up too. FetusGPT is one zany example of how Siskind uses humor to make a bigger point: AI is what we make of it. It’s an approach that feeds through her comedy writing and work as the founder of science and technology communications agency Hello SciCom. We had Siskind on AI & I to talk about how she uses AI in her creative process as a comedian, and the unexpected support it's become, both practical and emotional, as she navigates pregnancy. Want even more? Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Pitch is the AI presentation platform that helps professionals collaborate on, create, and deliver winning slide decks — all while staying on brand: https://pitch.com/use-cases/ai-presentation-maker/?utm_medium=paid-influencer&utm_campaign=every  Timestamps: 00:00:00 - Start 00:01:54 - Introduction 00:02:03 - How Siskind is running an experiment between her unborn child and an LLM 00:07:34 - A demo of Siskind’s FetusGPT 00:15:16 - Siskind’s pick for the funniest LLM 00:17:12 - How Siskind uses AI in her comedy writing 00:24:41 - Dan and Siskind use ChatGPT to write a joke together live on the show 00:37:21 - Why AI is useful even when you don’t use its output directly 00:44:15 - How Siskind used a ChatGPT project to biohack her energy levels 00:57:09 - A question we fundamentally couldn’t have asked in pre-ChatGPT times 01:05:29 - How ChatGPT is a source of emotional support for Siskind in pregnancy Links to resources mentioned in the episode: Sarah Rose Siskind: https://sarahrosesiskind.com/ Siskind’s agency Hello SciCom: https://www.hellosci.com/ Siskind’s book recommendations: I Forced a Bot to Write This Book, The Let Them Theory, Artificial Intelligence: An Illustrated History

    1h 14m

  4. DEC 3

    Why Opus 4.5 Just Became the Most Influential AI Model

    The world changed last week—Opus 4.5 is the best coding model Dan has ever used.It can keep coding and coding autonomously without tripping over itself—and it marks a completely new horizon for the craft of programming. The dream is here: You can write English, and make software.We had Paul Ford on AI & I to talk about it. Ford is the co-founder of Aboard and also a prolific writer. He authored one of Dan’s favorite pieces of technology writing What Is Code?—so he’s the perfect person to unpack this with him.We talk about the wonder—and genuine unease—that comes with using tools this powerful. We also get into what people who love technology should care about as the ground under us shifts faster than we can imagine.If you found this episode interesting, please like, subscribe, comment, and share! Want even more?Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: ⁠https://every.ck.page/ultimate-guide-to-prompting-chatgpt⁠. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper:Subscribe to Every: ⁠https://every.to/subscribe⁠Follow him on X: ⁠https://twitter.com/danshipper⁠ Head to ⁠ai.studio/build⁠ to create your first appReady to build a site that looks hand-coded—without hiring a developer? Launch your site for free at ⁠Framer.com⁠, and use code DAN to get your first month of Pro on the house! Timestamps:00:00:00 - Start00:01:57 - Introduction00:03:28 - How Claude Opus 4.5 made the future feel abruptly close00:08:12 - The design principles that make Claude Code a powerful coding tool00:10:57 - How Ford uses Claude Code to build real software00:20:12 - Why collapsing job titles and roles can feel overwhelming00:22:56 - Ford’s take on using LLMs to write00:24:09 - A metaphor for weathering existential moments of change00:25:45 - What GLP-1s taught Ford about how people adapt to big shifts00:49:36 - Why you should care what your LLM was trained on00:52:15 - Ford prompts Claude Code to forecast the future of the consulting industry00:59:18 - Recognize when an LLM is reflecting your assumptions back to you01:12:39 - How large enterprises might adopt AI Links to resources mentioned in the episode:Paul Ford: ⁠Paul Ford⁠Ford’s company Aboard: ⁠https://aboard.com/⁠The piece Ford wrote for Bloomberg in 2015: ⁠What Is Code?⁠Alan Kay’s concept of a personal computer for children: ⁠https://en.wikipedia.org/wiki/Dynabook⁠

    1h 25m

  5. NOV 26

    Best of the Pod: Would You Shut Down Your Most Successful Product? The Arc to Dia Story

    If you had millions of people using a product you spent years building, would you kill it? That’s exactly what The Browser Company did with Arc. Originally recorded in July before The Browser Company’s acquisition by software giant Atlassian earlier this year, we’re republishing this episode because its lessons are truly timeless. Today, the team continues to operate independently under Atlassian’s umbrella. The internet backlash when the company killed Arc in May 2025 was intense, but cofounders Josh Miller and Hursh Agrawal saw that AI was about to make the web something you talk to, not just click into. The best home for that assistant was the thing that's already between you and the internet—the browser. And they realized they couldn’t just duct-tape it on to Arc. One year of heads-down work later, the team launched Dia in beta, and people are raving about it. Dia is a sleek, fast, browser with AI at its core—it gets better with every tab you open, becoming more and more helpful with time. And even though it’s still early, Josh and Hursh’s big pivot looks like one for the ages. In this episode of AI & I, Josh and Hursh spoke for the first time in a full-length podcast about their pivot from Arc to Dia. We talked through their decision-making process, the very public backlash the company faced, and the grit it took to stay the course. If you found this episode interesting, please like, subscribe, comment, and share! Want even more?Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Timestamps:00:00:00 - Start00:00:48 - Introduction 00:02:22 - The story of how Dan might've been the CEO of The Browser Company 00:09:40 - The moment Josh and Hursh knew they had to walk away from Arc 00:16:59 - How to handle the weight of the unknown in a pivot 00:23:24 - The prototype-driven culture that kept The Browser Company alive 00:25:06 - Why having a product loved by millions of users isn't enough 00:32:12 - The architectural decisions underlying how Dia was built 00:46:04 - How Dia almost shipped without its best feature 00:50:45 - The best ways people are using Dia in the wild 01:07:27 - How Josh and Hursh think about competing with incumbents 01:17:13 - How romanticism informs the product decisions behind Dia Links to resources mentioned in the episode:Hursh Agrawal: @hurshJosh Miller: @joshmMore about Dia: https://www.diabrowser.com/ Writer and investor M.G. Siegler’s essay about the AI browser wars: https://spyglass.org/ai-browser-wars/ Note: This episode is a rerun from our archives.

    1h 24m

  6. NOV 19

    Best of the Pod: Claude Code - How Two Engineers Ship Like a Team of 15

    If you’re using AI to just write code, you’re missing out. Two engineers at Every shipped six features, five bug fixes, and three infrastructure updates in one week—and they did it by designing workflows with AI agents, where each task makes the next one easier, faster, and more reliable. In this episode of AI & I, Dan Shipper interviewed the pair—Kieran Klaassen, general manager of Cora, our inbox management tool, and Cora engineer Nityesh Agarwal—about how they’re compounding their engineering with AI. They walk Dan through their workflow in Anthropic’s agentic coding tool, Claude Code, and the mental models they’ve developed for making AI agents truly useful. Kieran, our resident AI-agent aficionado, also ranked all the AI coding assistants he’s used. If you found this episode interesting, please like, subscribe, comment, and share! Want even more?Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipperHead to ai.studio/build to create your first app. Pitch is the AI presentation platform that helps professionals collaborate on, create, and deliver winning slide decks — all while staying on brand: https://pitch.com/use-cases/ai-presentation-maker/?utm_medium=paid-influencer&utm_campaign=every  Timestamps:Episode start: 00:00:00Introduction: 00:01:16Why Kieran believes agents are turning a corner: 00:03:18Why Claude Code stands out from other agents: 00:06:36What makes agentic coding different from using tools like Cursor: 00:11:58The Cora team’s workflow to turn tasks into momentum: 00:15:20How to build a prompt that turns ideas into plans: 00:23:07The new mental models for this age of software engineering: 00:34:00Why traditional tests and evals still matter: 00:39:13Kieran ranks all the AI coding agents he’s used: 00:42:00 Links to resources mentioned in the episode:Try Cora, our AI email assistant: https://cora.computer/ Kieran Klaassen: @kieranklaassenNityesh Agarwal: @nityeshagaThe book that helps Nityesh form mental models to work with AI agents: High Output Management

    53 min
  7. Building AI Agents to Launch a Million Businesses

    NOV 12

    Building AI Agents to Launch a Million Businesses

    Henrik Werdelin wants to launch a million businesses that each make $1M—and he’s doing it with AI. After helping launch Barkbox and Ro Health through his incubator Prehype, Henrik is distilling everything he knows into Audos, a platform that helps you use AI agents to turn your idea into a profitable, lasting company. We had him on AI & I to talk about “portfolio entrepreneurship”—a new breed of entrepreneurship shepherded in by AI, where founders build families of products around the same customer, instead of one moonshot idea. It’s a philosophy we hold close to our hearts at Every. If you found this episode interesting, please like, subscribe, comment, and share! Want even more? Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipperHead to ai.studio/build to create your first app. Ready to build a site that looks hand-coded—without hiring a developer? Launch your site for free at https://www.framer.com/, and use code DAN to get your first month of Pro on the house! Pitch is the AI presentation platform that helps professionals collaborate on, create, and deliver winning slide decks — all while staying on brand: https://pitch.com/use-cases/ai-presentation-maker/?utm_medium=paid-influencer&utm_campaign=every ! Timestamps: 00:01:33 - Introduction 00:02:50 - Dan and Henrik on the new breed of entrepreneurship that AI makes possible 00:11:08 - Why Henrik believes the future belongs to a million $1M companies 00:16:14 - How to build “relationship capital” with your customers 00:21:35 - Why “customer-founder fit” shapes lasting companies 00:23:01 - Everything Henrik learned about himself from a decade of building companies 00:31:44 - How Henrik finds focus and meaning in the daily chaos 00:34:17 - How Henrik is parenting two kids in the age of AI 00:50:33 - The way AI can fix what social media broke 00:56:59 - What happens when AI agents become part of how we tell stories Links to resources mentioned in the episode: Henrik Werdelin: https://hellohenrik.com/Try Audos: https://www.audos.com/Henrik’s new book: https://www.amazon.com/Me-My-Customer-AI-Entrepeneurship/dp/B0FCSQ1C7H

    1h 6m
  8. What Jason Fried Learned from 26 Years of Building Great Products

    NOV 5

    What Jason Fried Learned from 26 Years of Building Great Products

    37signals makes tens of millions in profit every year but ⁠Jason Fried⁠ isn’t all that interested in running a business. Instead, he cares most about making great products—like ⁠Basecamp⁠, ⁠HEY⁠, and ⁠Ruby on Rails⁠—products that are centered around a single, coherent idea. These products are complete wholes, where each piece matters—like a Frank Lloyd Wright house or a vintage car. But how do you create products like that? In this conversation, we talk to Jason about what two decades of building 37signals has been like—and how to build products that have soul. If you found this episode interesting, please like, subscribe, comment, and share! Want even more? Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: ⁠https://every.ck.page/ultimate-guide-to-prompting-chatgpt⁠. It’s usually only for paying subscribers, but you can get it here for free. To hear more from Dan Shipper: Subscribe to Every: ⁠https://every.to/subscribe⁠Follow him on X: ⁠https://twitter.com/danshipper⁠Listen to Working Smarter wherever you get your podcasts, or visit ⁠workingsmarter.ai⁠.  Timestamps: 00:00:00 - Start 00:00:32 - Introduction 00:02:06 - What architecture, watches, and cars teach us about software 00:10:54 - How Jason thinks AI plays into product-building 00:20:58 - How developers at 37signals use AI 00:25:47 - Jason’s biggest realization after 26 years of running 37signals 00:29:58 - Where Jason thinks luck shaped his career 00:32:41 - What Jason would do if he were graduated into the AI boom 00:37:22 - Dan asks for advice on running a non-traditional company like Every 00:46:39 - Why staying true to yourself is the only way to build something lasting 00:49:38 - Wholeness as the north star for building products—and companies Links to resources mentioned in the episode: Jason Fried: ⁠Jason Fried (@jasonfried)⁠, ⁠Jason Fried⁠More about 37Signals: ⁠37signals⁠The book about architecture by Christopher Alexander: ⁠The Timeless Way of Building⁠

    58 min
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4.9
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About

Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the show. Join us to discover how AI is changing how we think about our world—and ourselves. For more essays, interviews, and experiments at the forefront of AI: https://every.to/chain-of-thought?sort=newest.

Information

  • Creator
    Dan Shipper
  • Years Active
    2023 - 2025
  • Episodes
    92
  • Rating
    Explicit
  • Copyright
    © Dan Shipper
  • Show Website
    AI & I

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