But then you eventually went on to become a venture capitalist.
It was a big transition. You go from kind of being a player on the field to being a coach. It is really hard, and there’s certain rules you kind of learn over time. One of them is: only pick one thing to really focus on. Not 50. Pick one and be very thoughtful and deliberate about what that one thing is because it’s like Whac-a-Mole otherwise. Also, just keep asking questions; not directing, but asking questions and just trying to be helpful overall.
Do you ever invest in a founder rather than invest in an idea?
There are times when we just see a phenomenal C.E.O. and we think, “Wow, no matter what this person does, they’re going to figure it out.” It’s like, do you bet on the jockey or the horse? You always bet on the jockey, because good jockeys won’t ride bad horses.
You invested in Lending Club and then were on the board. Were there any signs of some of the troubles to come?
Oh, dear. They had a phenomenal executive team, especially when they were like a Series C or D company. But they never added to it. They didn’t get a C.O.O. in. There were a lot of things like that, where they just maybe were a couple steps too late in adding some more seasoned executive talent.
You’ve been working in Silicon Valley for 20 years now. What’s changed during that time?
I was reading The Economist on my last European plane flight, and they think the next Democratic candidate will run on an anti-tech platform. I think that’s highly possible. If you poll other areas of the country, it’s not thought about like we like to think about ourselves. I think we need to really embrace the responsibility of how many lives we impact and how those lives are touched. I’m from the Midwest. I understand that the rest of the country doesn’t love California at all. We have to be a little more aware of ourselves and what we’re doing in tech, and try to do good things and help people.
What’s your biggest concern?
I think society is going to have a come-to-Jesus moment about what the true state of privacy is. It isn’t existent today, and I think people are just sort of blissfully ignorant of that fact. If you look at these companies and what they have on you, I think most people would be highly alarmed.
Is the tech backlash affecting how you think about investing in companies?
I think being in companies that we believe are at least net positive is the right thing to do. At the board level, a lot of what I push on very early in a company’s life is, “What’s your culture, what is it you guys are about?” It’s helpful for recruiting, it’s helpful for your product direction, it’s helpful for your company decision-making. As my old C.O.O. said, “There’s only one person you have to sleep with every night, and that’s yourself.”