The a16z Show

Snapshot · The a16z Show

Travis Kalanick Is Back | Building the Future of Industrial AI

Explore episode Jul 22, 2026

Where this was said

The Uber Series B Auction That Almost Went to a16z

At 6:01 · chapter starts 2:32

The story of Uber's Series B is a masterclass in venture deal dynamics, told from both sides of the table for what feels like the first time. Kalanick describes his 'uncapped anchor' method — setting a valuation floor, never a ceiling, and walking competing investors through successively higher numbers until the market clears. At $375M pre-money, a16z was in. Then came dinner with Andreessen, who revealed the partnership wouldn't support the number and came back at $210M. For Kalanick, having built that much momentum and having it collapse was a reputational crisis he had to scramble to repair — ultimately landing the deal with Shervin Milner through Menlo Park. Horowitz's version is stripped of the auction mechanics but heavy on the regret: he knew the deal was his, handed it off because he had too many board seats, and then spent a decade watching Uber win while sitting on the Lyft board as consolation.

Business
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.'

Similar snapshots