Insights
On Asymmetric Bets
An asymmetric bet is a small, calculated risk with a large potential upside. Not a gamble: you know the downside, you've capped it, and you make a lot of them. Forty cold calls and one big client. Twelve $20 ads and one winner. A duct-tape first product. The framework, with Dalio and Greene, and why there's no shame in the scrappy version.
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Burn the Boats
In 1519 Cortés sank his own ships so his men couldn't go home. Sun Tzu called it death ground, the Spartans held a pass with nothing behind them, Caesar crossed a river he couldn't uncross. It's not courage. It's engineering: remove the way out and focus follows. I've got news coming, and I'm on the beach right now.
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The Leash Got Longer
I'll die on the human-in-the-loop hill, because AI is terrible at judgment and once tried to expose my Mac mini to the internet. But it's great at the grunt work: UI tests, integrations, bug fixes, browser automation. So the CTO job changed shape, from in the weeds to architect and observer, and the same move applies to the CMO and COO. Preserve the brainpower for the make-or-break calls.
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We're Building a Mobile App for HyppoCRM
HyppoCRM is getting a real mobile app. Why: fragmented systems cost you leads, Slack-style integrations are glue that fails, and most of our users run their business from a truck, not a desk. How: one backend, two doors in, no sync, and Claude writing and testing most of the code while I architect and review.
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