From Cowboys to AI: Lessons from History

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.  

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Timestamps:

1. Introduction: 00:00:51

2. What pushed Will to go all in on AI: 00:03:25

3. Inside the ‘AI-first’ memo Will shared at Walleye: 00:14:08

4. Why you shouldn’t be afraid of using AI for work: 00:15:56

5. How Will uses LLMs to sharpen his thinking: 00:31:01

6. Walleye’s approach to using AI to reduce risk: 00:35:32

7. What history can teach us about leading through change: 00:39:10

8. Will’s first principles to making better decisions: 00:56:45

9. Why 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"