The a16z Show

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Travis Kalanick Is Back | Building the Future of Industrial AI

Explore episode Jul 22, 2026
Business
When the Pirate Becomes the Navy

Travis Kalanick Is Back | Building the Future of Industrial… · Jul 22, 2026 Business

There's a moment in every company's life when the scrappy tactics that built the business become liabilities. Ben Horowitz calls it 'when the pirate becomes the Navy.' Kalanick never internalized it — running programs named 'Shoplifting' and going right to the line. Horowitz realized it himself at a16z and pulled back before they suffered the same fate.

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The a16z Deal That Got Away: Uber's Series B Auction

Travis Kalanick Is Back | Building the Future of Industrial… · Jul 22, 2026 Business

Kalanick ran a masterclass in venture auction dynamics for Uber's 2011 Series B, using an 'uncapped anchor' technique to drive competing offers from $210M to $375M pre-money. Then a16z blinked at dinner, offering only $210M, and the deal went to Shervin Milner at Menlo Park — beginning a decade of what Ben Horowitz calls 'torture.'