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AI and I

Dan Shipper
AI and I
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  • GitHub CEO on the AI Coding Arms Race: One Agent, 150M+ Devs
    GitHub Copilot has 15 million users—more than Cursor and Windsurf combined. So why does it feel like they're losing the AI coding race?Last week at Microsoft Build, I interviewed the CEO of GitHub Thomas Dohmke to find out.I wanted to know: Is their huge existing user base a blessing or a curse? And will their latest launch—an autonomous coding agent built into GitHub—let them retake the lead? Watch this episode of AI & I to find outIf 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.Sponsor:Attio: Go to⁠⁠⁠⁠ https://attio.com/every⁠⁠⁠⁠⁠ and get 15% off your first year on your AI-powered CRM.To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Timestamps:Introduction (00:00:38)Copilot’s place in the AI coding agent race (00:07:40)Inside the product decisions behind Copilot’s new agent (00:10:42)How Dohmke thinks about shaping Copilot’s personality (00:16:18)How GitHub supports both AI-native developers and legacy enterprise users (00:20:29)Dohmke’s predictions for the future of software development (00:26:57)
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  • Kevin Scott on The Future of Programming, AI Agents, and Microsoft’s Big Bet on the Agentic Web
    I interviewed Microsoft CTO Kevin Scott about the future of agents and software engineering for another special edition of AI & I. With 41 years of programming behind him, Kevin has lived through nearly every big shift in modern software development. Here’s his clear-eyed take on what’s changing with AI, and how we can navigate what’s next:The real breakthrough for the agentic web is better plumbing. Kevin thinks agents won’t be useful until they can take action on your behalf by using tools and fetching data. To do this, agents need access across your systems—and Microsoft’s answer is adopting Model Context Protocol, or “MCP,” that allows an agent to access tools and fresh data beyond its knowledge base, as their standard protocol for agents to move through contexts and get things done.How the agentic web echoes the early internet. Just as protocols like HTTP and HTML gave the web a shared language, Kevin believes the  agentic web needs its own infrastructure—the first glimpses of this include MCP (the HTTP of agents) and NLWeb, Microsoft’s push to make websites legible to agents (similar to what HTML did for browsers).Open ecosystems can coexist with strong security systems. Kevin argues that the “tradeoff” between ecosystems that allow “permissionless” innovation and robust security is a false dichotomy. With AI agents that understand your personal risk preferences—and know your communication habits across email, text, and other channels—they could detect when something suspicious is happening and act on your behalf. The craftsman’s dilemma in the age of agents. Kevin is a lifelong maker—of software, ceramics, even handmade bags—and he cares deeply about how things are made. Because this can feel at odds with coding with AI agents, Kevin’s approach is to notice where the process matters most to him, and where it's okay to optimize for outcomes. After four decades of seeing breakthrough technologies, his advice is simple: be curious, try stuff, and use it if it works for you.The future of software engineering agents is plural. Kevin believes the future of software engineering agents will be diverse because developers who enjoy the freedom of playing with different tools is one of the most consistent patterns he’s seen in his decades in tech. What will drive this diversity, he says, is builders who deeply understand specific problems and tailor agents to solve them exceptionally well.How agentic workflows will evolve. Kevin sees a shift from short back-and-forth interactions with agents to longer, async feedback loops. As the agentic web matures and model reasoning improves, people will start handing off bigger, more ambitious tasks and letting agents run with them.Timestamps:Introduction: 00:01:44The race to close the “capability overhang”: 00:02:49How agents will evolve into practical, useful tools: 00:04:31The role Kevin sees Microsoft playing in the agent ecosystem: 00:06:48How robust security measures can coexist with open ecosystems: 00:12:05Kevin's philosophy on being a craftsman in the age of agents: 00:15:39How the landscape of software development agents will evolve: 00:20:52The future of agentic workflows: 00:25:33
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  • OpenAI Launches Codex: An Autonomous Programming Agent
    OpenAI just launched Codex, a brand-new coding agent that can build features and fix bugs autonomously. We’ve been testing it at Every for a few days, and I’m impressed.I invited Alexander Embiricos, a member of the OpenAI product staff responsible for Codex, to demo the agent live on a special edition of AI & I. We talk through:What Codex is and how it works. Codex’s UI allows developers to see the list of tasks the agent is working on, how many lines were changed for each, and the status of the PR. It’s built for the senior software engineer who wants to delegate and review tasks efficiently.How OpenAI is thinking about agents. Codex is one piece of a unified super-assistant OpenAI wants to eventually build—an agent that helps users easily get things done by selecting the right tools for them behind the scenes. Why an “abundance mindset” is best for interacting with agents. Codex is designed to allow users to delegate many tasks at once without getting caught up in the details. This lets you point an abundance of agents at a specific task, like a difficult bug—it’s worth it even if only one of them succeeds.OpenAI’s vision for the future of programming. In the future developers will probably spend less time writing routine code and more time guiding agents, reviewing their work, and making strategy decisions. Programming will become more social, letting teams easily delegate multiple tasks at once, allowing people to focus on ideas and collaboration instead of routine coding.Timestamps:Introduction: 00:00:52The product decisions behind Codex’s interface: 00:01:40How Codex works under the hood: 00:06:20Why you need an abundance mindset to work well with agents: 00:14:06Setting Codex to work on a real task in “Ask” mode: 00:16:28How OpenAI is thinking about designing agents: 00:18:54The future of programming is social: 00:31:16Reviewing Codex’s work live: 00:37:21How the landscape of agents will evolve: 00:39:41
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  • The $10B Hedge Fund CEO Who’s Betting Big on AI | Will England, Walleye Capital
    Will England just pivoted his $10B AUM hedge fund to go all in on AI with a firm-wide email:“I wrote this email using ChatGPT—you should too. As a hedge fund, we should be ashamed to leave money on the table by ignoring AI.”It’s working: 75% of his 400-person team are using ChatGPT daily—and Walleye is well on its way to transforming into an AI-first juggernaut. They record every meeting, use LLMs to ingest and analyze earnings reports, and are building “The Borg”—a firmwide intelligence layer.What’s surprising? Will isn’t some AI hype man: He’s the CEO, CIO, and managing partner of Walleye Capital, a multi-strategy hedge fund competing with firms like Citadel, Millenium, and Point72. He’s Princeton and Oxford educated, but he’s based in Minnesota, doesn’t have an X account, and rarely gives interviews.In my experience, teams go as their CEO goes—and Will is the best example of a CEO going all in on AI that I’ve seen. "It would be irresponsible not to go after AI with maximum discipline and intensity," Will told me—and in this episode he lays out his exact playbook for doing it.We get into:Why AI is essential operating leverage. At Walleye, using AI is treated like using email or Excel. Ignoring it means getting left behind—in an industry where information = money, every edge counts. England makes this not optional for anyone, backed by internal leaderboards and cash incentives.How Will uses AI for journaling and decision-making. Will journals every day using ChatGPT, which helps him with everything from decision-making at work to reflecting on his family life to tracking his workouts. How Will pivoted his billion dollar firm. Will’s commitment to AI isn’t theoretical—he announced AI as the new standard for work at Walleye, and made avoiding it unacceptable. How to lead during times of technological change. Will leads with an ethic of personal responsibility: "If we get disrupted by AI, that's on me.”Why students of history do better at handling the future. Will sees today like the 1860s–1910s era—when the Industrial Revolution introduced factories and railroads and the skills and roles needed inside of companies transformed quickly.How Will uses AI to write faster. Will uses ChatGPT to help him draft emails or memos that would have taken hours in 15 minutes. He bullets out of his thoughts and then uses LLMs to turn that into polished prose. Having AI handle the linguistic syntax gives him more time for conceptual thinking.This is a must-watch for anyone who wants to lead a team through change with clarity and conviction.  Sponsor:Attio: Go to⁠⁠⁠ https://www.⁠⁠⁠⁠attio.com/every⁠⁠⁠⁠ and get 15% off your first year on your AI-powered CRM.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: 00:00:51What pushed Will to go all in on AI: 00:03:25Inside the ‘AI-first’ memo Will shared at Walleye: 00:14:08Why you shouldn’t be afraid of using AI for work: 00:15:56How Will uses LLMs to sharpen his thinking: 00:31:01Walleye’s approach to using AI to reduce risk: 00:35:32What history can teach us about leading through change: 00:39:10Will’s first principles to making better decisions: 00:56:45Why Will journals everyday—and how AI makes it easier: 00:58:58 Links to resources mentioned in the episode:Will England: https://walleyecapital.com/bio/will-england Walleye Capital: https://walleyecapital.com/ Work with Every’s consulting team: https://every.to/consulting  Everything we’ve learned from consulting with clients like Walleye: "How We Built a 7-figure AI Consulting Business in Less Than a Year"
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  • Jhana Meditation Silenced Her Mind—And Changed Her View On AI | Nadia Asparouhova, Author and researcher
    After two Jhana meditation retreats Nadia Asparouhova could silence her mind, change her emotional state at will, and even intentionally slip out of consciousness. It challenged the idea that our minds are not under our control—and made her wonder if we’re more like AI than we realize. Nadia is a writer and researcher of technology and culture. She published Working in Public, a book about the evolution of open-source development, with Stripe Press in 2020. Her latest book, Antimemetics, is about why some ideas don’t go viral even though they’re powerful. I had her on the show to talk about her experience with Jhana meditation and how it reshaped the way she thinks about being human in the age of AI. We get into:Jhana as a means to nurture profound joy and calm. Unlike many meditation practices that emphasize passive observation, Jhana is goal-oriented—practitioners proactively cultivate states of concentrated bliss. Apart from helping her regulate her emotions, it prompted Nadia to reexamine deep questions of our human existence. Self-talk is not essential as it seems. Nadia describes how advanced meditation quieted her inner voice—challenging the idea that self-talk is core to being human.How years of cultural evolution have shaped our sense of self. According to Nadia, our modern conception of “self”  isn’t as timeless as we assume. She draws on psychologist Julian Jaynes’s theory that our inner dialogue—what we often equate with consciousness—only emerged in humans a few thousand years ago; a provocation to reconsider the benchmarks we use to assess the intelligence or sentience of LLMs.What it is like to experience a “cessation.” On her last meditation retreat, Nadia experiences a cessation where your consciousness abruptly winks out—like suddenly flipping a switch. Nadia described it as slipping into nothingness, then returning with the jarring realization that even your sense of self can vanish and reappear.Why she likes the unknowability of AI. The mechanics of exactly how LLMs predict their next token remain a mystery. Driven by thousands of subtle, context-dependent correlations, they’re too complex to distill into a simple explanation. Nadia finds joy in the unknowability of it all, seeing the ambiguity as an invitation to explore. How she uses AI as a writing partner. Nadia believes the trope of the solitary, brooding writer is beginning to shift with the rise of LLMs. For her, ChatGPT has made writing feel less isolating. She turns to it at both ends of the process: to help make sense of early ideas, and later, to sharpen phrasing and land on just the right words.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: 00:01:15The beginning of Nadia’s journey with Jhana: 00:02:34How Jhana is different from other meditation practices: 00:05:51 Jhana reframed the way Nadia thinks about being human: 00:09:52How Nadia integrates her experience with Jhana into her life: 00:14:16Nadia describes her experience of the final stage of Jhana: 00:16:44Why our modern sense of self isn’t as timeless as you might assume: 00:19:11How new technologies can be a mirror to ourselves: 00:23:53Nadia embraces the feeling of not knowing how AI precisely works: 00:33:55How Nadia uses ChatGPT to make writing less isolating: 00:38:03Links mentioned:Nadia Asparouhova: https://nadia.xyz/ Her deep dive on Jhana meditation: https://nadia.xyz/jhanas Nadia’s book: Working in Public, AntimemeticsBooks about how new technology can change our sense of self: The WEIRDest People in the World, Listening to Prozac
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Over AI and 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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