Before
A media entrepreneur rather than a financier. He founded Silicon Alley Reporter, then Weblogs Inc, sold to AOL for a reported thirty million dollars, then Mahalo.
The move
He was recruited rather than hired. Sequoia brought him into the earliest version of its scout arrangement because his media platform and founder relationships made him a trusted node in the network the firm wanted access to. That is the mechanism worth studying: the asset was not investing skill, it was standing among founders, and a firm was willing to rent it. He deployed roughly 600 thousand dollars across about twenty startups on the firm's behalf.
The turn
A 25 thousand dollar check into Uber, written after Travis Kalanick showed him the product informally. TechCrunch reported that his scout portfolio grew to over nine figures. He converted that record into his own syndicate and fund platform.
Timeline
- December 2006 to May 2007 formally an entrepreneur in action at Sequoia
- Roughly twenty scout investments made
- The Uber check becomes the outlier that defines the record
- LAUNCH and the syndicate platform built on top of it
What this route asks
Standing that a firm would pay to reach. It is worth being precise about two things: his formal title at Sequoia was entrepreneur in action rather than scout, though he is widely called the original scout, and the Uber outcome is the single most cited and least repeatable data point in the industry. The route is real. The return is not the lesson.