Duolingo’s AI Strategy: What to Borrow, What to Avoid

Company Breakdown #04 · Four decisions about people, products, markets and value.

Oct 9 • James Kerr

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How Ramp got 800 people building with AI

Company Breakdown #03 · Over 90% of its staff already used AI, but most were stuck in a chat window. Here's what Ramp changed, and what I'd borrow.

Oct 2 • James Kerr

10

5

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September 2026

Ozymandias’s Curse: What’s Worth Building?

Essay #13 · When anything can be instantly made obsolete, why you build becomes more important than what

Sep 29 • James Kerr

7

4

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How to earn your AI stripes, in 4 moves

Company Breakdown #02 · 83% of Stripe's staff use its AI every week. Three moves you can copy, and the one bet that hasn't paid off yet.

Sep 24 • James Kerr

10

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The 4 Secrets behind Shopify’s AI Strategy

Company Breakdown #01 · A masterclass in moving quickly, keeping what you learn, and staying useful as the market moves.

Sep 17 • James Kerr

8

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To Build a Mockingbird

Essay #12 · So... what happens when your customer can build?

Sep 8 • James Kerr

11

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August 2026

For God’s Sake, Don’t be Original?

Essay #11 · Trojan Horse Product Strategy: Adoption relies on building for the tools that already exist

Aug 26 • James Kerr

8

2

July 2026

How to Win in the Age of the Artisan

Essay #10 · When capability becomes abundant, advantage moves to the people who can combine craft, systems and distribution.

Jul 21 • James Kerr

16

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How to Use AI Like a Strategy Consultant

AI Guide #01 · The issue-tree method I use to turn a vague problem into something AI can actually investigate.

Jul 17 • James Kerr

12

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Building for an AI-Native Operating Model

Essay #09 · People are talking about AI-native. What we actually need is companies that can optimise and explore at the same time.

Jul 9 • James Kerr

8

4

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Utopia: The Case for Hope

Essay #08 · Not enough people are asking the question: how might it all go right?

Jul 2 • James Kerr

9

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June 2026

The Big Blind

Essay #07 · The risk of rockets and AI is being quietly transferred to our families' life savings. The least we can do is understand what we own.

Jun 25 • James Kerr

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