BACKSTORY

I’ve always thought, “What can I do that opens up possibilities?” I grew up in South Africa and went to an Afrikaans high school, and we didn’t speak English at home. But I pushed myself to go to an English-speaking university, and that opened up a door. Then I chose to work for McKinsey, because I thought it would open another door and maybe I’d get a chance to work overseas.

I was reading about what was happening in Silicon Valley in the mid 90s, before I came to the U.S. Already, I’m starting to see the beginnings of the internet. Did I fathom how big it would be? Absolutely not. I didn’t know what venture capital was. I didn’t know that I would join a startup. I just had an intuition that I needed to be here. A friend of mine introduced me to Elon in 1999 and I joined PayPal. Then when Mike Moritz asked me to come interview at Sequoia, that was just another door opening. Where might this one lead?

Whenever I interview people, I ask about those key moments in somebody’s life where they’ve made career decisions. And I think about companies in the same way—there are these crucible moments that have an enormous bearing on ultimate outcomes.

ON THE LOOKOUT FOR

The unconventional. So many times, I’ve led an investment and been made fun of. YouTube. Instagram. MongoDB. There’s a little defiance in saying, “We’ll show you!” I remember in 2001, when I was at PayPal, there was an article titled “Earth to Palo Alto.” It said we were deranged, we didn’t know what we were doing. In the meantime, I was inside the building, knowing that we were months away from being profitable and on our way to being a public company.

There’s something intriguing to me about somebody who’s an original thinker, who is quirky, and maybe an outsider. I love spending time with people like that. Often, I judge based on how I feel when I meet someone the second time. With most people, you can have a pretty interesting conversation once. The real test is the second conversation—do I lose interest? Or does my imagination start to run off as I think about what this company can become, and understand the depth and significance of the person’s idea? There are few things as exhilarating as sitting in a room with a founder and riffing with them on their idea.