Losing Pinterest

You're such a pioneer in the venture capital industry and you've had lots of successes, but I think like most people, we all make mistakes as well. Can you tell me about one big mistake you made when you started your career as a venture capitalist? And how did you overcome it?

Oh, boy. So many. Let's see. Well, there are mistakes in not winning deals. So I think pretty famously in there and everybody knows, so for the firm collectively not winning the Google deal, obviously, that would have been a great one, but more so I think early on the mistakes are, because it's like anything else, the really great entrepreneurs, are going to have lots of choices. So you can't win every deal. But it's around the judgment. And the ones that I think most venture capitalists lose sleep about are the ones that they missed, the big ones that got away that they just didn't get at the beginning.

So what do you lose sleep over?

So I have to say, you know, the early, early round investments in Pinterest. Obviously big mistake. I looked at it before it actually even found like what the initial use case was. So yes, they were pinning, it co-founded by Ben and one of his co-founders, two guys. And it was really much more about doing research on the Internet and having a good way to sort of collect those and pin those. And it really didn't take off until a later round when Ben was, I think the story is pretty well known when he was engaged and then he and his fiancŽ were pinning and creating ideal boards for their wedding and their honeymoon and all of those kinds of things. And that was really kind of the first use case. It really was when it took off. So it was really Ben's fiancŽ, now wife, I think deserves a lot of the credit. But anyway, so, you know, it was at the time there were a bunch of other things kind of sort of trying to do that. And it's really hard to know the ones that are going to take off. And what's the use case that's gonna catch lightning in a bottle. So that was a mistake.

And then so how do you overcome that? You just kind of have to say, OK, that's life. Cie la vie. Move on.

Yeah, you do that. You have to do that. But you also have to see if there are learnings from that. So for me, learning from that is, you know, stay close to the companies because in venture there's always another round. There's always usually five or six rounds these days, more even before a company goes public. So stay close enough. So when you start to see signs of a change in trajectory, you know, reengage.