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.

  1. 3 days ago

    The AI Alien Companion App That's Bringing In $4M a Year (Best of the Pod)

    LLMs are a new medium for storytelling. That’s according to the creators of Portola, the company behind Tolan: an embodied AI companion that lives on its own planet and chats to you with a distinct personality. In 2025, Portola's founder and CEO Quinten Farmer and Head of Story Eliot Peper joined Dan Shipper to explain how they’re building this new medium from scratch. Their aim is to help users go from overwhelmed to grounded through conversations with Tolan that feel personal and spontaneous, not scripted.  On this week’s AI & I, Dan revisits his conversation with Quinten and Eliot. They discuss why response time is everything for voice-based AI interfaces, how Portola designs AI personalities users will click with, and why character-driven AI could become a new computing interface. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipper Go to https://attio.com/every and get 15% off your first year. Timestamps: 00:01:30 - Introduction 00:04:07 - Talking to the Portola CEO's Tolan, Clarence 00:09:11 - How Portola went from building software for kids to AI companions 00:23:40 - Why response time is everything for voice-based AI interfaces 00:29:54 - Tolans don't use scripted prompts—they're taught to improvise 00:37:23 - How to know which AI personalities your users will click with 00:42:27 - Developing the character traits of an AI companion 00:49:48 - What does it mean to build technology that makes us flourish 01:01:10 - How Portola evaluates whether Tolans are resonating with users 01:11:01 - Inside Portola's viral growth strategy

  2. 12 Aug

    Microsoft’s Vision for an Internet Made for Agents With CTO Kevin Scott (Best of the Pod)

    In 2025, Kevin Scott bet that the agentic web would be the next big thing in AI.The Microsoft CTO argued that for agents to be genuinely useful, they'd need to be able to take action on our behalf—which would mean giving them access to the same sprawl of tools, data, and systems that make up the internet. Today, that bet is starting to pay off, as the foundational infrastructure for the agentic web is now being built. On this week's AI & I, Dan Shipper revisits his conversation with Kevin. They discuss Microsoft's role in the agentic web, why openness doesn't have to come at the expense of security, and why programmers should stay curious about new tools rather than resist them on principle. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipper Go to https://attio.com/every and get 15% off your first year. Timestamps: 0:00 Start1:44 Introduction2:49 The race to close the "capability overhang"4:31 How agents will evolve into practical, useful tools6:48 The role Kevin sees Microsoft playing in the agent ecosystem12:05 How robust security measures can coexist with open ecosystems15:39 Kevin's philosophy on being a craftsman in the age of agents20:52 How the landscape of software development agents will evolve25:33 The future of agentic workflows Links to resources mentioned in the episode:Kevin Scott on X: https://twitter.com/kevin_scottModel Context Protocol (MCP): https://modelcontextprotocol.ioNLWeb: https://github.com/microsoft/NLWebGitHub Copilot: https://github.com/features/copilot

  3. 5 Aug

    Why the Next Hit AI Product Will Be Social Why the Next Hit AI Product Will Be Social (Best of the Pod)

    Most consumer AI so far has been single-player: you and a chatbot, alone. Benchmark partner Sarah Tavel, one of Pinterest's first 30 employees, is betting that's about to change. She's looking for a product genius who can build an AI product with social DNA: status, network effects, and multiplayer dynamics. That'll enable users of ChatGPT and other models to learn from how others use AI and level up. On this week’s AI & I, Dan Shipper revisits his conversation with Sarah. They talk about why technical founders dominate the early days of a platform shift while product-minded founders win later, what ChatGPT is still missing, and what separates a founder's real network effect from a slide with a flywheel diagram. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Timestamps for YouTube: 0:00 Start 1:10 Introduction 2:26 Why the future of consumer AI belongs to founders with product intuition 11:09 What Sarah sees as ChatGPT's biggest weakness 18:45 How Sarah would design a consumer AI app with social DNA 24:10 The kind of founders Sarah invests in 28:33 How to know if your startup's network effects are real 35:40 What's catching Sarah's eye beyond AI 40:41 How AI will change the way top venture capitalists invest Links to resources mentioned in the episode: Sarah Tavel on X: https://x.com/sarahtavel Benchmark: https://benchmark.com Agentio (marketplace for YouTube creators and brands): https://agentio.com/  Chainalysis: https://chainalysis.com The Five Temptations of a CEO by Patrick Lencioni: https://www.amazon.com/dp/B007BZBRB8 Thinking in Bets by Annie Duke: https://www.amazon.com/dp/B0HBBW23PM

  4. 29 Jul

    Best of the Pod: Wired's Kevin Kelly on Why AI Is a 50-year Overnight Success

    Kevin Kelly has spent over 30 years experiencing the edge of new technology: from the earliest days of the internet to the first years of Burning Man. But he’s always treated the frontier as a place to visit, not somewhere to live. It’s partially how he’s been able to stay grounded through tech’s various hype cycles.As founding executive editor of Wired and author of The Inevitable, Kelly spends as much time analyzing the latest in AI as he does reading about significant moments in history. It’s a discipline he traces back to his work with the Long Now Foundation, which he cofounded to encourage long-term thinking, reaching from the last 10,000 years to the next. On this week’s AI & I, Dan Shipper revisits his conversation with Kelly. They get into why historians can be the best futurists, and how our bid to understand what intelligence is has parallels with early scientists' attempts to figure out electricity. Kelly also describes the joy he found in creating an AI-generated saga featuring Leonardo Da Vinci, Christopher Columbus, and Martin Luther—one that will only ever be read and enjoyed by him. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipper Timestamps for YouTube:0:00 Start 0:50 Introduction 1:10 Why Dan and Kelly love Annie Dillard 12:52 How to predict the future like Kelly16:10 What the history of electricity can teach us about AI 20:13 How Kelly thinks about the nature of intelligence 25:44 Kelly's advice on discovering your competitive advantage 29:33 How Kelly assembled a bench of star writers for Wired 34:43 How Kelly used ChatGPT to co-create a book 39:12 Using AI as a mirror for your mind 43:43 What Kelly learned from betting on VR in the 1980s Links to resources mentioned in the episode:Kevin Kelly on X: https://twitter.com/kevin2kellyThe Inevitable by Kevin Kelly: https://www.amazon.com/Inevitable-Understanding-Technological-Forces-Future/dp/0525428089Pilgrim at Tinker Creek by Annie Dillard: https://www.amazon.com/Pilgrim-Tinker-Harper-Perennial-Classics/dp/00612333231,000 True Fans by Kevin Kelly: https://www.amazon.com/1000-True-Fans-Kellys-Simple-ebook/dp/B01N9P9O4GFull episode transcript: https://every.to/podcast/transcript-be243312-ea22-4193-8c56-b9cd45a79a87

  5. 1 Jul

    The AI Workflows Behind Every's Consulting Team

    Natalia Quintero joined Every as head of consulting with a mandate to bring AI into the workflows of executives at hedge funds, private equity firms, and tech companies. She is also a recent Codex convert—someone who spent months resisting the tool before Dan Shipper’s daily pestering finally got her to try it. Natalia encountered Codex as a non-technical builder who had learned to navigate file systems and folder structures in Claude Code through sheer effort. She’s now used Codex to do everything from automate her CRM setup to build a portal to manage her father’s medical care.Dan talked with Natalia for AI & I about what it looks like to go from non-technical to building software with Codex, why Every still uses software-as-a-service products from Attio and Asana instead of vibe coding their own tools, and where she thinks AI agents like Every’s internal Claudie employee require human managers. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipper Timestamps:00:01:05 Introduction00:02:35 How Natalia manages Claudie, the consulting team's AI project manager00:04:55 Why the consulting team still pays for SaaS products00:11:47 Codex as a game changer00:14:55 Building personalized learning guides and illustrated explainers with AI00:21:40 Inside Natalia's AI-powered email triage system00:26:44 The shift from knowledge work as sculpting to knowledge work as gardening00:28:57 Using Codex to one-shot a custom CRM00:33:16 Using Codex to build an app that coordinates her father's medical care Links to resources mentioned in the episode:Natalia Quintero on X: https://x.com/NataliaZarinaAsana (project management): https://asana.comEvery Consulting: https://every.to/consulting Go to attio.com/every and get 15% off your first year.

  6. 24 Jun

    Building a School Where AI Models Learn About Humanity

    If scaling laws hold—and Surge AI CEO Edwin Chen believes they do—we’re hurtling toward a future where there’s nothing humans can do that AI can’t do better. When OpenAI’s models disproved an open conjecture posed by mathematician Paul Erdős using novel algebraic geometry techniques, Fields medalist Timothy Gowers felt the shift acutely. He initially thought the model had proved an upper bound, and braced himself: that would mean it was “all over for mathematicians very soon.” When he realized it had only found a counterexample, he was relieved—it bought him another year or two before the thing he’s devoted his life to becomes something AI does better. As founder and CEO of the company behind the data environments and evals the major model companies use to train their models, Chen has a unique perspective on how quickly AI models are absorbing tasks we used to think of as uniquely human. Dan Shipper talked with Chen for AI & I about what the act of creating or building means when AI can do it better—and whether an answer to that question already exists within science fiction. If you found this episode interesting, please like, subscribe, comment, and share! Join the membership for Where You Live at ⁠https://www.joinbilt.com/dan To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipper Timestamps:00:00:54 Introduction00:01:49 Surge as a "school for AGI"00:04:46 What AI's capacity for novel mathematics says about human achievement00:07:29 Motivation in an era when AI can do everything00:14:34 The trap of optimizing AI models for engagement00:29:34 Training using datasets versus training using environments00:35:09 The value of personal data00:39:40 Why models are bad at writing00:42:00 Chen's AGI timeline Links to resources mentioned in the episode:Edwin Chen on X: https://x.com/echenSurge: https://surgehq.aiRiemann-bench (research-level math benchmark): https://surgehq.ai/leaderboards/riemann-benchHemingway-bench (creative writing benchmark): https://surgehq.ai/leaderboards/hemingway-benchTalkie-1930 (language model trained on pre-1930 text): https://huggingface.co/talkie-lm/talkie-1930-13b-itTed Chiang, “What’s Expected of Us”: https://www.nature.com/articles/436150a Every is the most AI-native startup on the internet. Through ideas, software and education, subscribers get the tools to work at the frontier of AI. Start your free trial today: https://every.to/subscribe?utm_source=youtube Follow Every: https://x.com/everyFollow Dan Shipper: https://x.com/danshipper

  7. 17 Jun

    GitHub’s COO Explains Why AI Hasn’t Replaced Developers

    Last year, there were 1 billion commits on GitHub. This year, Kyle Daigle expects that number to exceed 14 billion, a two-component explosion caused by more humans—and their agents—issuing pull requests. In March alone, 17 million pull requests on GitHub were created by agents.Daigle is the COO of GitHub and Microsoft’s chief marketing officer for developer products. He’s been at GitHub for 13 years, and is paying close attention to how AI is expanding the platform’s user base. Along with agents, legal, sales, and marketing professionals are building apps with the GitHub Copilot app. The line between developer and non-developer is disappearing.On this episode of AI & I, guest host Mike Taylor sat down with Daigle at Microsoft Build to discuss how GitHub is building infrastructure for an agent-native world: agentic code review, model routers that automatically select the right model for the task, and a philosophy that the most durable advantage in this market is developer choice. If you found this episode interesting, please like, subscribe, comment, and share! Want even more?To hear more from Mike Taylor:Subscribe to Every: https://every.to/subscribeFollow him on X: https://x.com/hammer_mtTimestamps for YouTube:00:00:52: Introduction00:03:27: The agentic PR flood00:04:33: GitHub's approach to helping open-source maintainers manage the surge00:06:15: What 14 billion commits means for code quality00:08:03: Moving from per-seat licensing to usage-based pricing00:09:45: Kyle's dual role as GitHub COO and Microsoft's chief marketing officer for developers00:13:03: Developer choice as competitive moat00:14:57: How to balance dogfooding your own tools with staying honest about the competition00:19:45: Hill climbing, frontier tuning, and solving the model-routing problem00:24:45: Kyle's agentic communication hackLinks to resources mentioned in the episode:Kyle Daigle on X: https://x.com/kdaigleMike Taylor on Every: https://every.to/@mike_2114Mike’s piece on building an AI version of Kyle Daigle: https://every.to/also-true-for-humans/i-interviewed-an-ai-version-of-github-s-coo-then-spoke-to-the-real-oneGitHub Copilot: https://github.com/features/copilot

  8. 10 Jun

    How Anthropic Uses Claude Fable 5 With Mike Krieger

    Mike Krieger built one of the most consequential consumer apps of the last two decades as the cofounder of Instagram. He is now at the frontier of AI-native product development as head of Anthropic Labs, the team responsible for figuring out what the most capable AI models can do in the hands of real builders.When Krieger first got access to Fable 5 months before its public release, it was exciting and disorienting. “I feel like a total newbie again,” he remembers telling his team. The way he’d been thinking about productivity, strategy, and time management was out of date. The model had outpaced his workflows.Dan Shipper talked with Krieger for AI & I about what it looks like to build with a model as capable as Fable 5, including the new rhythms, challenges, and possibilities it reveals.If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipperGet started with Braintrust at https://www.braintrust.dev/  Timestamps:0:03 Introduction1:48 How Fable completely reshaped Mike's workflow4:48 When to use Sonnet versus Fable10:06 What the media tracker Mike built over a weekend reveals about agent-native architecture15:00 The cost to build has collapsed19:03 Is software engineering over?21:48 How Anthropic's engineering teams work today38:39 The mechanics of verification44:39 What people should use the model to build47:24 Dynamic workflows Links to resources mentioned in the episode:Mike Krieger on X: https://x.com/mikeykAnthropic Labs: https://www.anthropic.comClaude Code: https://claude.ai/codeEvery: https://every.to

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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
    127
  • Rating
    Clean
  • Copyright
    © Dan Shipper
  • Show Website
    AI & I

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