AI & I

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

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/subscribe
Follow 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 Kelly
16:10 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/kevin2kelly
The Inevitable by Kevin Kelly: https://www.amazon.com/Inevitable-Understanding-Technological-Forces-Future/dp/0525428089
Pilgrim at Tinker Creek by Annie Dillard: https://www.amazon.com/Pilgrim-Tinker-Harper-Perennial-Classics/dp/0061233323
1,000 True Fans by Kevin Kelly: https://www.amazon.com/1000-True-Fans-Kellys-Simple-ebook/dp/B01N9P9O4G
Full episode transcript: https://every.to/podcast/transcript-be243312-ea22-4193-8c56-b9cd45a79a87