AI and I

Two years ago, Katie Parrott was laid off from a crypto firm and couldn’t afford a career coach—so she turned to a $20-a-month ChatGPT subscription instead. The Every staff writer’s habit of feeding AI good context eventually became compound writing, a codified system for brainstorming, drafting, and editing with AI. Today, that system is a plugin any writer can use. On this week’s AI & I, Natalia Quintero talks with Katie about turning good ingredients into good writing, borrowing the taste of writers she admires, and why AI helped her fall back in love with the page. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Natalia Quintero: Subscribe to Every: https://every.to/subscribe Follow her on X: @NataliaZarina Go to https://attio.com/every and get 15% off your first year. Timestamps for YouTube: 0:00 Start0:49 Introduction1:21 How Katie went from being laid off to using ChatGPT as a career coach8:06 Turning AI into a “content agency of one”10:59 Building the context files and style guides that make AI outputs useful14:15 What makes a Claude project actually work21:18 How AI helped with a mental health crisis and “computer errands”27:03 Katie’s career coach, now a fully autonomous Codex project32:27 What compounding means, and building the Compound Writing plugin38:00 Borrowing Vonnegut, Hitchcock, and Sorkin as AI editing skills44:49 Katie’s thesis: education and access will matter more than ever Links to resources mentioned in the episode: Katie Parrott on X: @kplikethebird Compound writing plugin: ⁠https://github.com/EveryInc/compound-writing Compound engineering plugin (Kieran Klassen): github.com/EveryInc/compound-engineering-plugin Parrott’s companion piece on compound writing: https://every.to/guides/compound-writing Parrott, “I Hired ChatGPT as My Career Coach”: every.to/working-overtime/i-hired-chatgpt-as-my-career-coach Parrott, “AI Turned Me Into a Content Agency of One”: every.to/working-overtime/ai-turned-me-into-a-content-agency-of-one

Will England is the CEO of Walleye Capital, a hedge fund managing nearly $10 billion in assets. An engineer by training with a math background from Oxford, he has spent his career at the intersection of machines and markets—and has made AI fluency mandatory for all 400 employees. England believes refusing to use AI is like refusing to use the internet in 1995 because it wasn’t perfect. His use of AI is public and effusive, including in a firm-wide email that opened with “I used ChatGPT to write this email. You should be using it, too, and be proud of it.” AI informs how Walleye drafts memos and selects stocks. On Every’s AI & I, Dan Shipper spoke with England about why he’s betting his entire organization on AI, why “results are what matter” more than blood, sweat, and tears, and what the American frontier can teach us about leading through technological change. Like, subscribe, comment, and share! To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow Dan Shipper on X: https://twitter.com/danshipper Go to https://attio.com/every and get 15% off your first year. Timestamps: 0:00 Start 0:51 Introduction 3:25 What pushed Will to go all in on AI 15:15 Inside the ‘AI-first’ memo Will shared at Walleye 17:02 Why you shouldn’t be afraid of using AI for work 31:25 How Will uses LLMs to sharpen his thinking 35:57 Walleye’s approach to using AI to reduce risk 39:35 What history can teach us about leading through change 57:10 Will’s first principles for making better decisions 59:23 Why Will journals every day—and how AI makes it easier Links to resources mentioned in the episode: Will England/Walleye Capital: https://walleyecapital.com/bio/will-england Every’s AI tools—Monologue, Cora, Spiral, and Sparkle: https://every.to/studio Every’s AI consulting: https://every.to/consulting

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/danshipperGo 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

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/subscribe Follow him on X: https://twitter.com/danshipper Go to https://attio.com/every and get 15% off your first year. Timestamps: 0:00 Start 1:44 Introduction 2:49 The race to close the "capability overhang" 4:31 How agents will evolve into practical, useful tools 6:48 The role Kevin sees Microsoft playing in the agent ecosystem 12:05 How robust security measures can coexist with open ecosystems 15:39 Kevin's philosophy on being a craftsman in the age of agents 20:52 How the landscape of software development agents will evolve 25:33 The future of agentic workflows Links to resources mentioned in the episode: Kevin Scott on X: https://twitter.com/kevin_scott Model Context Protocol (MCP): https://modelcontextprotocol.io NLWeb: https://github.com/microsoft/NLWeb GitHub Copilot: https://github.com/features/copilot

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