AI & I

Dan Shipper
AI & I
Latest episode

166 episodes

  • AI & I

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

    25/02/2026 | 53 mins.
    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)
  • AI & I

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

    18/02/2026 | 46 mins.
    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
  • AI & I

    Inside OpenAI’s Agentic Browser, Atlas

    11/02/2026 | 55 mins.
    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
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    [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
  • AI & I

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

    04/02/2026 | 47 mins.
    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
  • AI & I

    How Andrew Wilkinson Uses Opus 4.5 in His Work and Life

    21/01/2026 | 1h 2 mins.
    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

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About AI & I

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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