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. JAN 21

    How Andrew Wilkinson Uses Opus 4.5 in His Work and Life

    Entrepreneur Andrew Wilkinson used to sleep nine hours a night. Now he wakes up at 4 a.m. and goes straight to work—because he can’t wait to keep building with Anthropic’s latest model, Opus 4.5. Two years ago, Wilkinson was obsessed with vibe coding on AI software development platform Replit. It was thrilling to describe something in plain English and watch an app appear, less thrilling when the apps were always broken in some way, often full of maddening bugs. So he set his app creation ambitions aside until technology caught up with them. Then, a few weeks ago, he started playing with Claude Code and Opus 4.5. It felt, he says, like having a “$100,000-a-month payroll of engineers” working for him around the clock. Wilkinson is the cofounder of Tiny, a company that buys profitable businesses and holds them for the long term. The Tiny portfolio includes the AeroPress coffee maker and Dribbble, a platform where designers can share their work and find jobs. Dan Shipper had him on AI & I to talk about the automations Wilkinson has built for his work and personal life, including an AI relationship counselor, a custom email client, and a system that texts him outfit recommendations each morning. Wilkinson revealed how all of this individual exploration has changed the way he thinks about buying software companies at Tiny. 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/danshipperReady to build a site that looks hand-coded—without hiring a developer? Launch your site for free at www.framer.com, and use code DAN to get your first month of Pro on the house! Timestamps: 00:00:00 - Start 00:01:07 - Introduction 00:02:48 - Why Opus 4.5 feels like the iPhone moment for vibe coding 00:08:31 - Why designers have a unique advantage with AI00:14:10 - How Wilkinson built a custom email client with Claude Code 00:18:13 - An AI trained on your relationship that predicts your fights 00:30:40 - Using AI meeting notes to make your life better00:35:11 - Don't inject your opinion into prompts 00:40:21 - Wilkinson’s Claude Code tips and workflows 00:47:59 - Your personal stylist is a prompt away 00:53:17 - How AI is changing the way Wilkinson invests in software Links to resources mentioned in the episode: Andrew Wilkinson: Andrew Wilkinson (@awilkinson)The book Wilkinson references in his prompts, when writing copy with AI: Made to StickEvery’s compound engineering plugin: https://github.com/EveryInc/compound-engineering-plugin

    1h 3m

  2. JAN 14

    Why Your AI Learning Projects Keep Fizzling Out

    LLMs have made it absurdly easy to go deep on almost any topic. So why haven’t we all used ChatGPT to earn college degrees we wished we had majored in or pursued a niche interest, like learning how to name the trees in our neighborhood? I know I’m not the only one to feel guilty for well-intentioned attempts at autodidactism that inevitably peter out. Entrepreneur Nir Zicherman has a reason for this disconnect: LLMs can answer most of your questions, but they won’t notice when you’re lost or pull you back in when your motivation starts to fade. As the CEO and cofounder of Oboe, a platform that generates personalized courses about everything from the history of snowboarding to JavaScript fundamentals using AI, Zicherman has thought deeply about why the ability to access information does not automatically lead to understanding a concept. In this episode of AI & I, he talks to Dan Shipper about everything he’s learned about learning with LLMs. They get into Zicherman’s counterintuitive belief that learning is a more passive process than you’d think, the biggest blocker for most people who want to learn something new, and where AI agents currently fall short in providing a meaningful learning experience. 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: 00:00:00 - Start 00:00:36 - Introduction 00:01:49 - Why you need a dedicated AI learning app 00:04:32 - The process of learning is more passive than you might think 00:10:21 - Live demo of Oboe to create a course about philosopher Ludwig Wittgenstein 00:16:52 - Learning works best when it comes in many formats 00:28:21 - Where AI agents currently fall short in the learning experience 00:34:10 - The importance of making learning feel accessible 00:35:56 - How Zicherman uses Oboe to learn quantum physics 00:40:54 - How embeddings spaces remind Dan of quantum mechanics Links to resources mentioned in the episode: Nir Zicherman: @NirZichermanLearn something new with Oboe: https://oboe.com/

    55 min

  3. JAN 13

    Vibe Check: Claude Cowork Is Claude Code for the Rest of Us

    Anthropic just dropped Claude Cowork—essentially Claude Code for everyone, not just engineers—and we got to chat about it with a product engineer at Anthropic who helped build it. In this live Vibe Check, Dan Shipper and Kieran Klaassen explore the new interface together, testing what works (and what doesn't) in real time. Anthropic’s Felix Rieseberg joins midway through to explain the philosophy behind Cowork's design: why it separates "Tasks" from "Chats," how the queue system lets you send messages while the agent is working, and what "agent-native" architecture means in practice. They also dig into Skills—Claude's prompt system that lets you customize how it works—and the Chrome connector for browser automation. This is a raw, unfiltered first look at what might be the future of how knowledge workers interact with AI: async workflows instead of turn-by-turn chat. If you found this episode interesting, please like, subscribe, comment, and share! Want even more? Check out Dan's guide to building agent-native applications: https://every.to/guides/agent-nativeTo hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipper 00:01:00 - What is Claude Cowork00:02:36 - First demo: competitor analysis00:03:33 - Email drafting that sounds like me00:06:18 - Calendar audit running for an hour00:07:39 - Book taxonomy demo00:08:42 - PostHog analytics via Chrome browsing00:14:36 - Chat vs Code vs Cowork: when to use what00:31:06 - Felix from Anthropic joins00:36:39 - Why they built it in a week and a half00:37:57 - Design decision: why a separate tab00:43:57 - Skills as the primary hackable surface00:49:36 - Agent-native architecture principles00:56:57 - The origin story of skills at Anthropic01:03:00 - Our final rating

    1h 33m

  4. JAN 7

    AI in 2026: Reid Hoffman’s Predictions on Agents, Work, and Creation

    From cofounding LinkedIn to backing OpenAI early, Reid Hoffman is in the habit of being right about the future, so we wanted to know what he saw coming in 2026. In his third appearance on AI & I, Hoffman lays out his predictions for where AI will go in the 12 months ahead. He talks to Dan Shipper about how agents will break out of coding into other domains and who’s winning the coding agent race. They also get into how Hoffman defines artificial general intelligence, the way he believes enterprises will use AI, and why public debate on AI might turn more negative, even as the technology becomes more empowering for individuals. Hoffman’s other bets on the future include cofounding AI drug discovery startup Manas AI, investing at venture capital firm Greylock Partners, writing books, and hosting the Masters of Scale podcast. He’s also an investor 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/danshipper Timestamps: 00:00:00 - Start 00:00:52 - Introduction 00:02:20 - The future of work is an entrepreneurial mindset 00:05:22 - Creation is addictive (and that’s okay) 00:09:22 - Why discourse around AI might get uglier this year 00:17:03 - AI agents will break out of coding in 2026 00:24:18 - What makes Anthropic’s Opus 4.5 such a good model 00:28:46 - Who will win the agentic coding race 00:36:13 - Why enterprise AI will finally land this year 00:43:16 - How Hoffman defines AGI 00:55:33 - The most underrated category to watch in AI right now Links to resources mentioned in the episode: Reid Hoffman: Reid Hoffman (@reidhoffman)The AI drug discovery startup Hoffman cofounded: Manas AI

    1 hr

  5. 12/31/2025

    Four Predictions for How AI Will Change Software in 2026

    Tomorrow is the first day of 2026, and to give our listeners a view of the trends that’ll shape the year ahead, Dan Shipper had Every COO Brandon Gell on AI & I to discuss their predictions for what’s next. They discussed how software will be built, who will build it, and what it will take for truly autonomous AI agents to become a reality. 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 — Start 00:01:05 — Introduction 00:01:34 — Reflections on Every’s growth over the past year 00:09:38 — What changes when a company grows from 20 to 50 people 00:11:55 — How agent-native architecture will change software in 2026 00:17:13 — Why designers are slated to become power users of AI 00:23:24 — The new kind of software engineer who will direct AI agents 00:33:42 — Why the next wave of AI training will focus on autonomy

    37 min

  6. 12/24/2025

    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

  7. 12/16/2025

    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

  8. 12/10/2025

    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
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4.9
out of 5
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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 - 2026
  • Episodes
    97
  • Rating
    Explicit
  • Copyright
    © Dan Shipper
  • Show Website
    AI & I

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