Doug Leone on Sequoia, Fear, Great Founders & Starting Over at 69

David Senra (0:02)

All right, we were just talking before recording, and you just said something that's very interesting. We're talking about people that dominate for decades. You're one of them that's done so. And you said an interesting question is to ask how and why somebody would dominate for decades. What's your answer to that?

Doug Leone (0:15)

My partner in India said there are many roads to heaven.

And so there are many ways to dominate.

Take Steve Jobs. He had really one job, and he dominated in that domain for a lot of years. Or Jensen Wong. Those are more linear. Those are gifts where you find yourself in the middle of the hurricane. You just want to keep on going because as the world changes, your job changes. What's more interesting is how do you dominate when you have to remake yourself over and over again? And why do you dominate? Starting with the why, I think it's a deep and secure need to remain relevant and prove to yourself that you're not getting old and you're not going to be out of date. I mean, if I look back on my career, each time I remade myself, it wasn't really done out of vision or greatness. It was done out of fear of just being gone. Even a few minutes ago, I asked you, let's not make the interview be about yesterday. Let's make it about all tomorrow. And I still have that fear at the age of 69

And the how, I think you have to be willing to let go of your ego. I think you have to assume you know nothing each time and you're willing to start at the bottom. So when I came back to Sequoia, they gave me this fancy title of chairman. We were in front of our LPs, our investors, the first time about six months ago. And someone asked me about chairman. I told them, it's a bunch of bullshit. What I really am is an analyst. I'm a low level analyst and I have to prove myself. I just got back from vacation just this morning.

I've had 90 days of getting all calibrated. And my partner has asked me, how do you feel after 90 days? I said, I feel like I'm good for nothing. I feel like I've entered and AI has gotten further away from me than when I first started 90 days ago. And so I'm terrified. I told one of my partners just an hour ago that if nine months from now, which is the one year since I returned, I feel just as irrelevant, I'm going to take myself out. And so I don't know if I can do it yet another time. And therein lies the fun and therein lies the answer to your question.

David Senra (2:46)

Do you know who Jimmy Iovine is?

Doug Leone (2:48)

No.

David Senra (2:48)

Okay, Jimmy Iovine, he, another guy, dominated for decades. He was in the music industry for 50 years. But a lot of people know him because he had the insight to start building businesses with his artists. So he co-founded Beats with Dr. Dre. They wound up doing Beats music and headphones. They sell to Apple.

Doug Leone (3:04)

I think he's the guy that was involved with the Beatles at the very end.

David Senra (3:08)

John Lennon.

Doug Leone (3:09)

Yeah, John Lennon.

David Senra (3:10)

He was an engineer and a producer for John Lennon.

Doug Leone (3:12)

He showed up on a Saturday and next thing you know, yes.

David Senra (3:15)

I love him. He's fucking Italian from New York.

Doug Leone (3:17)

I know who he is. I forgot his name.

David Senra (3:19)

He's awesome. I didn't have to go with him, but now we've become friends. We talk all the time. He's a very extra character. But there's two things that where you were talking that he said the same thing. He's like, I don't have a rearview mirror. He said the same thing when we sat down. I said, I don't want to fucking talk about the past. I want to talk about what I'm doing now. He's like, there's no trophy room in my house. I can't even tell you what I did five years ago because I forgot. I'm worried about tomorrow. That was very interesting. But then my question, you brought up being terrified. And then you said fear before that.

What's your relationship like to fear? Because he gave some of the best advice. He's like, most people, when they feel fear, they let it be a headwind. He's like, I train myself to make it a tailwind. As soon as I feel it, that means I have to fucking go forward right now.