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AI & I

Dan Shipper

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.

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  • 124 episodes
  • Updated Wednesday

Episodes124

Newest first
  • March 18 · 56 min

    How Every Builds a Writing Team in the Age of AI

    Kate Lee has spent her career working with words—first as a literary agent, then in roles at Medium, WeWork, and Stripe. As Every’s editor in chief, she’s been the quiet force behind the newsletter for more than three years. Lately, something has shifted in Kate’s work. After years of watching her colleague Dan Shipper evangelize AI from the front lines, Katie has started rewiring how she works and is integrating more and more AI tools in her work. We had Kate on to talk about her career path from book deals to tech startups, what it really means to run a newsletter as a small team in the age of AI, and what she thinks the bottleneck to automating copyediting is. Plus: the story of pulling off reviews of two major model releases in 24 hours, and how she’s using her AI-powered browser to help her hire. To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Timestamps 0:01 – Introduction and Kate's early career as a literary agent 4:45 – From book publishing to tech: Medium, WeWork, and Stripe Press 12:00 – How Kate joined Every and what made the role click 27:00 – What it's like to be a knowledge worker at the frontier of AI 31:00 – The “aha” moment: using AI to manage hundreds of applicants 36:24 – How Every's editorial team uses AI to enforce standards and train taste 45:06 – Publishing two reviews of major model releases on the same day 51:39 – What automating copy editing requires Links to resources mentioned in the episode: Proof: https://www.proofeditor.ai/

  • March 11 · 44 min

    We Made a Document Editor Where Humans and AI Work Side by Side

    Every has unveiled a new product, built by CEO Dan Shipper. It's called Proof, a free, open-source, live collaborative document editor built for humans and AI agents to work in together. Proof started as a Mac app designed to show the provenance of AI-written text—purple for AI, green for human. But when Shipper rebuilt it as a web app with real-time collaboration, something clicked. Suddenly, everyone at Every was using it for everything from planning docs, to creative writing and even daily to-do lists. The team realized they needed a lightweight space where their OpenClaw agents and humans could co-author documents and leave comments. In this special episode, Shipper is joined by Every chief operating officer Brandon Gell, Cora general manager Kieran Klaassen, and head of growth Austin Tedesco to demo Proof live and share how it's changed the way they work. Brandon walks through a loop where his Codex agent writes a plan, Dan's personal Claw R2-C2 reviews it, and the humans just steer. Austin explains how he uses Proof to write a weekly food newsletter, texting ideas to his Claw on runs and watching an outline take shape. And Kieran makes the case that Proof's power is its lightness—just a link you can hand to any agent or colleague. The conversation covers what "agent native" means in practice, why AX (agent experience) matters as much as UX (user experience), what happens when 10 agents edit one document at the same time, and why some writing is now better read by an AI than a human. 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 Get started building today at http://framer.com/dan for 30% OFF a Framer Pro annual plan. Download Grammarly for free at Grammarly.com Timestamps 00:02:00 — Introduction and the origin story of Proof 00:07:24 — From Mac app to collaborative web editor 00:09:00 — What makes Proof “agent native” 00:14:30 — Live demo: watching an agent join and write inside a shared document 00:20:51 — How Austin uses Proof for creative writing and food journalism 00:24:30 — The challenge of multiple agents editing one document simultaneously 00:26:48 — When AI-written docs are better read by agents than by humans 00:29:30 — Brandon’s agent-to-agent collaboration loop 00:37:09 — Proof as a lightweight scratchpad vs. existing tools like Notion and GitHub 00:42:18 — Why Proof is open source and what that means for builders Links to resources mentioned in the episode: Proof Editor:⁠ https://proofeditor.ai⁠ Proof GitHub repo (open source):⁠ https://github.com/EveryInc/proof⁠ Every's compound engineering plugin:⁠ https://github.com/EveryInc/compound-engineering-plugin⁠

  • March 4 · 45 min

    Meet the Slowest Startup Incubator in the World—Pumping Out Billion-dollar Companies

    Silicon Valley loves billion-dollar moonshots and AI darlings. Sam Gerstenzang and Dan Friedman are doing something different—they're starting medical spas and funeral homes. On this episode of AI & I, Dan Shipper sat down with Gerstenzang and Friedman, partners at Boulton and Watt, which they call the "world's slowest startup incubator." Their model: Come up with an idea, achieve five or 10 million dollars in revenue themselves, then hand it off to a CEO who can take it to the next stage. They've used this playbook to build Moxie, a Series C company that helps nurses open their own medical spas, now with 600-plus customers and a 200-person team globally. Their second company, Meadow Memorials, is a contemporary funeral home with no physical real estate. It has become the largest provider of funeral services in California. Both businesses launched right around the arrival of ChatGPT—and neither was built with AI in mind. So how are they thinking about AI inside companies where the core work isn't going to change? In this conversation, Gerstenzang and Friedman share how they built an AI agent called Matthew Bolton to power their customer discovery process, why synthetic customer calls completely failed for them, and why they believe you shouldn't give anyone credit for using 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 Intent is what comes after your IDE. Try it yourself: augmentcode.com/intent Head to granola.ai/every to get 3 months free. Ready 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 — Introduction and how Sam and Dan's paths first crossed 00:01:40 — What it means to be “the world's slowest incubator” 00:04:50 — Why Bolton and Watt runs companies to several million in revenue before handing off to a CEO 00:07:30 — How specialization across the founding journey creates advantages 00:10:40 — Building AI-durable businesses versus AI-native ones 00:16:10 — How an AI agent transformed their customer discovery process 00:19:30 — Where synthetic customer calls completely fail 00:29:30 — Deploying AI inside established companies 00:32:30 — Why newer projects see huge gains from AI while mature companies see 10 percent 00:37:00 — A preview of what's next for Bolton and Watt

  • February 25 · 53 min

    Meet the Student With No Teachers, No Homework—Just AI

    Depending on whom you ask, AI is either the best or worst thing that can happen to the next generation. The arguments come from educators, venture capitalists, op-ed writers, and anxious parents—but rarely from the young people in question. On this episode of AI & I, Dan Shipper sat down with one: Alex Mathew, a 17-year-old high-school senior at Alpha High School in Austin, Texas. Alpha School, a rapidly expanding network of kindergarten through grade 12 private schools, is not without controversy. Inside Alpha High School, there are no traditional teachers, all academic content is delivered through an AI-powered platform, and the adults in the classroom, known as “guides,” focus solely on supporting the students emotionally and keeping them motivated to learn. The students have two- to three-hour learning blocks every morning and spend the rest of the day going deep on a project in an area they care about, spanning art, sport, life skills, and entrepreneurship. Mathew’s project is a startup called Berry, built around an AI stuffed animal designed to help teenagers with their mental health. His vision is for teens to talk to the plushie for five to 10 minutes a day and, in the process, learn to recognize and cope with their problems in the right way. In this episode, Dan and Mathew talk about what a day at Alpha High looks like, what keeps students from cheating when AI is everywhere, and how Generation Z—people born between 1997–2012—really feels about college, social media, and books. 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 In a world of generic AI, don’t sound like everyone else. With Grammarly, you never will. Download Grammarly for free at Grammarly.com. Intent is what comes after your IDE. Try it yourself: augmentcode.com/intent Head to granola.ai/every to get 3 months free. Timestamps: 00:00:00 – Start 00:01:30 – Introduction 00:04:08 – A typical day inside Alpha High School 00:06:54 – Why Alpha replaced teachers with “guides” focused on motivating students 00:12:09 – Why Mathew doesn’t use AI to cheat, even though he could 00:19:51 – Do ambitious teenagers care about going to college? 00:25:12 – Mathew’s take on how Gen Z thinks about AI 00:27:52 – How Mathew thinks about the effects of social media 00:31:29 – Gen Z’s relationship with books and reading 00:38:57 – Mathew ranks ChatGPT, Claude, Gemini, and Grok 00:47:12 – Why Mathew is building Berry, an AI stuffed animal for teen mental health Links to resources mentioned in the episode: Alex Mathew: Alex Mathew (@alxmthew) More about Berry: https://berryplush.com/, Berry (@berryaiplushies)

  • February 18 · 46 min

    OpenAI's Codex: This Model Is So Fast It Changes How You Code

    OpenAI’s hottest app isn’t ChatGPT—it’s Codex. In the last few weeks alone, the Codex team shipped a desktop app, GPT-5.3 Codex (a new flagship model), and Spark, the fastest coding model I’ve ever used. Usage has grown fivefold since January, and over a million people now use Codex weekly. Codex was also the app that OpenAI chose to run an ad for in the Super Bowl. Dan Shipper talked to Thibault Sottiaux, head of Codex, and Andrew Ambrosino, a member of technical staff who built the Codex app, for Every’s AI & I about what OpenAI is building and how they’re using it internally. 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 Head to granola.ai/every and get 3 months free with the code EVERY. Timestamps: 00:00:00 - Start 00:01:27 - Introduction 00:05:27 - OpenAI's evolving bet on its coding agent 00:09:42 - The choice to invest in a GUI (over a terminal) 00:20:38 - The AI workflows that the Codex team relies on to ship 00:26:45 - Teaching Codex how to read between the lines 00:28:45 - Building affordances for a lightening fast model 00:33:15 - Why speed is a dimension of intelligence 00:36:30 - Code review is the next bottleneck for coding agents 00:41:24 - How the Codex team positions against the competition Links to resources mentioned in the episode: Thibault Sottiaux: Tibo (@thsottiaux) Andrew Ambrosino: Andrew Ambrosino (@ajambrosino) Every’s vibe check on everything the Codex team launched: OpenAI's Codex App Gains Ground on Claude Code, GPT-5.3 Codex—The 10x Engineer, Now More Fun at Parties, AI as Fast as Your Train of Thought

  • February 11 · 55 min

    Inside OpenAI’s Agentic Browser, Atlas

    The AI labs fighting for attention during the Super Bowl call to mind another iconic Super Bowl moment: Apple’s 1984 ad for the Macintosh, which promised that the personal computer would be a source of unbound wonder, freedom, and delight. They were right, but over time, the personal computer has also become cluttered with errands. These “computer errands”—downloading a W-2 when tax season rolls around, hunting for the right coupon code before checkout, or navigating the unholy labyrinth of the Amazon Web Services dashboard just to change one permission setting—have taken over our digital lives. Atlas, OpenAI’s agentic browser, sprang from the idea that AI should handle this tedium for you. In this week’s episode of AI & I, Dan Shipper sat down with two members of the Atlas team, Ben Goodger and Darin Fisher. Goodger is Atlas’s head of engineering, and Fisher is a member of the technical staff. Both are legends of the browser world. They’ve spent decades building the modern web, working together on Netscape, Firefox, and Chrome before arriving at Atlas. From that vantage point, they told Dan how they think browsing is about to change, why building a browser is harder than it looks, and what it’s like to create a new one with AI coding tools like Codex. 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 Move fast, don’t break things Most AI coding tools don’t know which line of code will actually break your system. Try Augment Code, which understands your entire codebase, including the repos, languages, and dependencies that actually runs your business, and use their playbook to learn more about their framework, checklists, and assessments. Ship 30% faster with 40% shorter merge times. [Playbook at ⁠augmentcode.com⁠] Timestamps: 00:01:57 - Introduction 00:11:51 - Designing an AI browser that’s intuitive to use 00:15:24 - How the web changes if agents do most of the browsing 00:25:06 - Why traditional websites will not become obsolete 00:29:00 - A browser that stays out of the way versus one that shows you around 00:39:51 - How the team uses Codex to build Atlas 00:44:47 - The craft of coding with AI tools 00:52:33 - Why Goodger and Fisher care so much about browsers Links to resources mentioned in the episode: Ben Goodger: Ben Goodger (@bengoodger) Darin Fisher: Darin Fisher (@darinwf) OpenAI’s browser, Atlas: Introducing ChatGPT Atlas

  • February 4 · 47 min

    How We Built 'Claudie,' Our AI Project Manager (Full Walkthrough)

    A few weeks ago, Natalia Quintero wouldn’t have called herself technical. But since the beginning of January, she has woken up at 6 a.m. to vibe code with Claude. The AI project manager she built saved her 14 hours a week. Getting there meant scrapping the system three times and starting over. But the result handles everything from onboarding new clients to generating weekly updates across all projects. Natalia is the head of AI consulting at Every. As part of the role, she's spoken with over 100 organizations in the past year and worked with a select two dozen, including hedge funds, private equity firms, and Fortune 500 companies. She’s seen what separates companies thriving with AI from those floundering, and it comes down to patterns that have nothing to do with having the most resources or the fanciest tools. Dan Shipper had her on AI & I to share what she’s learned from this front-row seat to AI adoption. Quintero reveals how a private equity firm cut investment memo creation from three weeks to 30 minutes, why AI adoption needs to come from the top down, and what happened when she learned from her early morning experiments. She also explains why the companies going furthest with AI are the ones that give employees permission to fail—and how that counterintuitive approach is revolutionary. 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 www.Framer.com, and use code DAN to get your first month of Pro on the house. Timestamps: 00:00:00 - Introduction 00:01:30 - Why successful AI adoption requires coordinated, top-down effort 00:07:05 - How a private equity firm reduced investment memo creation from weeks to 30 minutes 00:13:30 - The benefits of connecting AI to proprietary context 00:15:20 - The plan-delegate-assess-compound framework for engineering teams 00:17:55 - How non-technical team members are becoming vibe coding addicts 00:20:50 - Building Claudie: an AI project manager from scratch 00:23:00 - Why creative exploration time outside the 9-to-5 is essential 00:27:50 - Live demo: How Claudie automates client onboarding and tracking 00:38:40 - The human side of AI: spending less time in spreadsheets, more time with people Links to resources mentioned in the episode: Natalia Quintero: Natalia Quintero (@NataliaZarina) What Natalia learned from working with companies on AI adoption: https://every.to/on-every/the-next-chapter-of-every-consulting Every’s compound engineering plugin: https://github.com/EveryInc/compound-engineering-plugin

  • January 21 · 1 hr 2 min

    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/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 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 AI 00:14:10 - 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 better 00:35:11 - 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 Stick Every’s compound engineering plugin: https://github.com/EveryInc/compound-engineering-plugin

  • January 14 · 55 min

    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/subscribe Follow him on X: https://twitter.com/danshipper Timestamps: 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: @NirZicherman Learn something new with Oboe: https://oboe.com/

  • January 13 · 1 hr 32 min

    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-native To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper 00:01:00 - What is Claude Cowork 00:02:36 - First demo: competitor analysis 00:03:33 - Email drafting that sounds like me 00:06:18 - Calendar audit running for an hour 00:07:39 - Book taxonomy demo 00:08:42 - PostHog analytics via Chrome browsing 00:14:36 - Chat vs Code vs Cowork: when to use what 00:31:06 - Felix from Anthropic joins 00:36:39 - Why they built it in a week and a half 00:37:57 - Design decision: why a separate tab 00:43:57 - Skills as the primary hackable surface 00:49:36 - Agent-native architecture principles 00:56:57 - The origin story of skills at Anthropic 01:03:00 - Our final rating

  • January 7 · 59 min

    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/subscribe Follow 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

  • Dec 31, 2025 · 37 min

    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

  • Dec 24, 2025 · 1 hr 1 min

    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 founder 00:08:22 - The fundamental problem with “trolley problems” 00:14:27 - How AI is changing the essentialism v. nominalism debate 00:29:33 - Why embeddings align with nominalism 00:34:26 - How LLMs are being trained to reason better 00:44:52 - How technology changes the way we see ourselves and the world around us 00:46:24 - Why most psychology literature is wrong 00:52:46 - Why philosophers didn’t come up with AI 00:56:30 - How to use ChatGPT to be more philosophically inclined Links to resources mentioned in the episode: Reid Hoffman: https://twitter.com/reidhoffman The 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/0465026567 Reid’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/0374173222 The 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

  • Dec 16, 2025 · 1 hr 16 min

    Jhana Meditation Live: How Anyone Can Achieve Super Wellbeing

    We had someone guide himself toward Jhana live on our podcast. And he narrated himself 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/subscribe Follow him on X: https://twitter.com/danshipper Timestamps: Introduction: 00:00:56 A primer on Jhana meditation: 00:01:18 Zerfas guides himself towards 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 Zerfas Jhourney: https://www.jhourney.io/ The Donella Meadows book Zerfas refers to: Thinking in Systems: A Primer

  • Dec 10, 2025 · 1 hr 13 min

    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

  • Dec 3, 2025 · 1 hr 25 min

    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 app 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 00:01:57 - Introduction 00:03:28 - How Claude Opus 4.5 made the future feel abruptly close 00:08:12 - The design principles that make Claude Code a powerful coding tool 00:10:57 - How Ford uses Claude Code to build real software 00:20:12 - Why collapsing job titles and roles can feel overwhelming 00:22:56 - Ford’s take on using LLMs to write 00:24:09 - A metaphor for weathering existential moments of change 00:25:45 - What GLP-1s taught Ford about how people adapt to big shifts 00:49:36 - Why you should care what your LLM was trained on 00:52:15 - Ford prompts Claude Code to forecast the future of the consulting industry 00:59:18 - Recognize when an LLM is reflecting your assumptions back to you 01:12:39 - 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

  • Nov 26, 2025 · 1 hr 23 min

    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 - Start 00:00:48 - 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: @hursh Josh Miller: @joshm More 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.

  • Nov 19, 2025 · 53 min

    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/subscribe Follow him on X: https://twitter.com/danshipper Head 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: 00:00:00 Introduction: 00:01:16 Why Kieran believes agents are turning a corner: 00:03:18 Why Claude Code stands out from other agents: 00:06:36 What makes agentic coding different from using tools like Cursor: 00:11:58 The Cora team’s workflow to turn tasks into momentum: 00:15:20 How to build a prompt that turns ideas into plans: 00:23:07 The new mental models for this age of software engineering: 00:34:00 Why traditional tests and evals still matter: 00:39:13 Kieran 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: @kieranklaassen Nityesh Agarwal: @nityeshaga The book that helps Nityesh form mental models to work with AI agents: High Output Management

  • Nov 12, 2025 · 1 hr 5 min

    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/subscribe Follow him on X: https://twitter.com/danshipper Head 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

  • Nov 5, 2025 · 58 min

    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/subscribe⁠ Follow him on X: ⁠https://twitter.com/danshipper⁠ Listen 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 Fried⁠ More about 37Signals: ⁠37signals⁠ The book about architecture by Christopher Alexander: ⁠The Timeless Way of Building⁠