Sublime

The biggest leak in my early years was that I frequently assumed that if I, or my very qualified friends, could execute on a plan, then my investments could, too. I assumed that all founders were dogged and die-hard, but I learned the hard way—after a half-dozen startups gave up and gave their investors five to fifty cents on the dollar back—that n

In order to be an effective angel investor, you need some combination of money, time, network, and expertise.

OnStartups.com

People always ask me, “How do you pick billion-dollar companies to invest in?” You don’t pick billion-dollar companies. You pick billion-dollar founders.

communications.

Why now? This question has been floating around the Valley for a while, and the first time I heard it was from my friend, Sequoia Capital’s Roelof Botha—the venture capitalist who convinced me to become a “Scout” for their firm, which led to my two greatest investments to date: Uber and Thumbtack. If you unpack this question, you’re really asking,

Remarkably, it is wholly owned by Craig Newmark and Jim Buckmaster, who are two of the most understated billionaires in tech.

At times I’ve been incredibly detailed in my feedback, giving founders all the reasons why I was not investing in them and softening the blow by telling them to “keep this email and do a blog post quoting it when you prove me wrong!”