AI & 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:
0:00 Start
0:49 Introduction
1:21 How Katie went from being laid off to using ChatGPT as a career coach
8:06 Turning AI into a “content agency of one”
10:59 Building the context files and style guides that make AI outputs useful
14:15 What makes a Claude project actually work
21:18 How AI helped with a mental health crisis and “computer errands”
27:03 Katie’s career coach, now a fully autonomous Codex project
32:27 What compounding means, and building the Compound Writing plugin
38:00 Borrowing Vonnegut, Hitchcock, and Sorkin as AI editing skills
44:49 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/subscribe
Follow 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

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