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AI CMOs are Coming
If you’re like me, you’re noticing AI is writing pretty much everything you’re reading these days. If you’re REALLY like me, you’re getting a bit sick of it. “It’s not X, it’s Y” is making all the Substacks I was unwittingly subscribed to even more intrusive. The minute I identify that AI wrote what I’m…
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Digitizing Voice Buttons
In the movie Arrival, there’s a scene where Ian reads from Dr. Louise Banks’ book: “Language is the foundation of civilization,” she wrote. “It is the glue that holds people together. It’s the first weapon drawn in a conflict.” Arrival is based on Ted Chiang’s “A Story of Your Life” which is about the difference…
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FMB 15: How Founders Choose Investors
This is an extension of my #FMB “Founders are Made, not Born: How Founders Become Learning Animals” series. Originals based on research at Stanford: Part I, Part II, Part III, Part IV, Part V, Part VI, and Part VII. Extensions: Parts 7, 8,9, 10,11, 12, 13, 14. During fundraises, founders often ask how to choose investors. I’ve met 1,000+ of investors and been part of dozens of boards.…
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FMB 14: The Anatomy of a “Why Now”
See the original linkedin post. This is an extension of my #FMB “Founders are Made, not Born: How Founders Become Learning Animals” series. Originals based on research at Stanford: Part I, Part II, Part III, Part IV, Part V, Part VI, and Part VII. Extensions: Parts 7, 8, 9, 10, 11, 12, 13. One of…
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The Hierarchy of Metrics
Metrics are not all made equal I’m on the board of a startup where, a few weeks ago, our board group chat got into a fun debate over text. It wasn’t about product direction or hiring plans, but about metrics. Ranking metrics. One of the founders shared this metrics snapshot and asked, “which metrics should…
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Search is at War
Defensibility in the Age of AI Search Search is at war. LLMs are quickly changing how consumers search. A lot is at stake, including the market caps of 2 of the top 5 most valuable companies in the world. Google (GOOG: $1.9T market cap) and Amazon (AMZN: $2.04T) each dominate different types of search: knowledge…
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NIM Innovation: A Lending Mental Model
Foreword: I’ve long been a mentor of startups in the Entrepreneurship and VC class at Stanford. Recently I was hosting several GSB students from the class who were working on a lending startup, and we got to “whiteboarding.” Well, napkin writing. I shared my lending mental model with them and realized I’ve never encapsulated it…
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Prime Directive: How Sci-Fi Lessons Map to Investing
Our planet is dying. Or, at least it always is in my favorite books. At its core, science fiction is about founders—pioneers who envision radical futures and take radical action. And just like Kirk, Picard, Janeway, or really anyone in space wearing a yellow shirt, the founders I look for don’t just iterate in the…

