Category: Uncategorized


  • How to Navigate a World of Bullshitters

    How to Navigate a World of Bullshitters

    David Lee Roth, Van Halen’s frontman, came off like Axe body spray in human form—loud, brash, and ridiculous. But that surface read was wrong. Underneath the show, he was playing a smarter game. Here’s how. Yes, this essay is about AI.

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  • My AI Startup Got Steamrolled by ChatGPT

    My AI Startup Got Steamrolled by ChatGPT

    The first time our AI business advisor recommended Viagra to solve a cash-flow problem, I should have known we were in trouble. At the time, it just felt like part of the fun. This was 2019. Before COVID, before “AI” meant ChatGPT to everyone. Back then, TikTok was still a teen fad, WeWork had just imploded, and the hottest tech IPO was Peloton. Large language models were a fringe research curiosity, not the center of the tech universe.

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  • The Ballmer Method for Prompting

    The Ballmer Method for Prompting

    In the late 2000s, Microsoft CEO Steve Ballmer always came off a bit unhinged. Sweaty and loud, he became a meme while ranting about Microsoft’s future. There’s an apocryphal story about how Steve figured out something important, that ended up being a prescient take about an AI-first world. I think about this story once a week; I hope it is equally impactful for you in how you use AI.

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  • Why Experts Are the Worst Teachers

    Why Experts Are the Worst Teachers

    About twenty years ago, I developed a repetitive stress injury from playing guitar. I was in a band, and I had to quit. The pressure I had to apply to the fretboard created a tendon issue that just wouldn’t go away. But I wasn’t ready to walk away from music entirely. If I couldn’t play guitar, I figured I’d get into electronic music. So I bought a copy of Reason, a program used by music producers to make beats.

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  • The Last Moat

    The Last Moat

    At AI Innovation Week in Mexico, we explored a counterintuitive idea: As AI makes public knowledge cheap, relationships and unspoken knowledge rise in value. This piece explores that concept through the lens of a hedge fund manager’s rogue approach to the Enron collapse.

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  • Mexico Stories and Observations

    Mexico Stories and Observations

    I just wrapped up AI Innovation Week at IPADE—Mexico’s most prestigious business school—across their Mexico City and Monterey campuses. The formal recap is on my work site. But here on the personal website, I share the things that caught my attention during my time south of the border. Read on for the interesting and unusual, from the witchraft market to the grandma who tried to seduce me.

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  • A Simple Rule for Managing Complexity: The Double Cushion

    A Simple Rule for Managing Complexity: The Double Cushion

    My favorite business school professor made good money managing extreme complexity: he oversaw consulting gigs involving multimillion dollar real estate purchases, factory operations with thousands of employees, and complicated mergers. He seemed to be able to see around corners.

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  • It’s Perfectly Fine that Origin Stories are Lies

    It’s Perfectly Fine that Origin Stories are Lies

    Blockbuster charged Reed Hastings a $40 late fee, which inspired him to found Netflix. Pierre Omidyar’s wife wanted to trade Pez dispensers online so he spent a weekend building a side project that became eBay. On a trip to Paris, Uber founder Travis Kalanick found himself stranded in the rain for 20 minutes trying to hail a cab. These are all good stories. And they are all lies.

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