Fred Wilson on 40 Years in Venture — and Why USV Is Automating Itself

**Fred Wilson** (0:02)
If I was starting a venture capital firm today from scratch, there's only three things that I would be focused on the humans in the firm doing. Startups have to play chess. They have to see three or four moves ahead. I'm not suggesting we all like $25 million on fire, but getting it wrong is just a byproduct of the kind of investing we do.

**Michael Mignano** (0:22)
I would like to show you something.

**Fred Wilson** (0:24)
Okay.

**Michael Mignano** (0:24)
Something we have never talked about.

**Fred Wilson** (0:25)
All right.

**Michael Mignano** (0:26)
Look at this.

**Fred Wilson** (0:27)
Holy crap.

**Michael Mignano** (0:36)
What's up?
Good to see you. Good to see you too. How's it going?

**Fred Wilson** (0:40)
It's going great.

**Michael Mignano** (0:41)
It's nice to meet you on the namesake of the fund, right? Below, that's George Washington, right?

**Fred Wilson** (0:47)
It is George Washington, and this is Union Square.

**Michael Mignano** (0:49)
It feels like an appropriate place to start. Why don't we go sit at a bench?

**Fred Wilson** (0:53)
Okay, cool.

**Michael Mignano** (0:53)
Obviously, you're so associated with New York now, with Union Square. In my mind, you're like the quintessential New Yorker. Sports fandom, et cetera.
But I don't know how you became a New Yorker, and you're not from here, right?

**Fred Wilson** (1:06)
Well, I think that the secret is that I didn't grow up anywhere because I grew up in an army, Brad. I literally moved like 20 times in my life before.

**Michael Mignano** (1:15)
20? Yeah, yeah.

**Fred Wilson** (1:16)
And so when I landed here, Joanne and I landed here, we came to New York together. We both were just like, we're going to become New Yorkers.

**Michael Mignano** (1:24)
Yeah. When was that?

**Fred Wilson** (1:26)
83

**Michael Mignano** (1:27)
Wow.

**Fred Wilson** (1:28)
Yeah.
I was like, I got to pick sports teams, so I had to pick my sports teams. And we lived in Manhattan, and we lived in this neighborhood, actually. And we became regulars at spots in this neighborhood, like we became New Yorkers.

**Michael Mignano** (1:42)
The interesting thing about you saying you had to choose your sports teams, obviously you and I, we talk a lot about sports, we talk about the Knicks, we talk about the Mets.
I was born into the sports fandom of the pathetic New York sports teams like the Mets, and for most of their history, the Knicks. You chose that. Yeah. Why did you choose to join the Mets legion of awfulness?

**Fred Wilson** (2:06)
I like to root for the underdog.

**Michael Mignano** (2:07)
Okay.

**Fred Wilson** (2:08)
I've always been a sucker for the underdog, so I couldn't pick the Yankees and I couldn't pick the Giants.

**Michael Mignano** (2:13)
Are you a Jets fan?

**Fred Wilson** (2:15)
Yeah.

**Michael Mignano** (2:15)
Okay, nice, great.

**Fred Wilson** (2:16)
I mean, no, it's not nice. It's horrible to be a Jets fan.
Awful.

**Michael Mignano** (2:20)
I say to my dad every day, how did you get me involved in this? It's like a miserable existence to be a Jets fan.

**Fred Wilson** (2:26)
It's the worst. I mean, being a Mets fan isn't all that bad.

**Michael Mignano** (2:29)
No, I mean, I love the Mets. I was there two nights ago, but I mean, it's really painful. There's many, many years of heartbreak and frankly, the Knicks too.

**Fred Wilson** (2:37)
Yes.

**Michael Mignano** (2:38)
It's heartbreaking to be a Knicks fan.

**Fred Wilson** (2:39)
The Knicks from 1999 until like two or three years ago were perennially the worst team in the NBA.

**Michael Mignano** (2:45)
Yeah, absolutely.

**Fred Wilson** (2:47)
And you know, like we have to go to San Francisco all the time. During a lot of that time, the Warriors were the best team.

**Michael Mignano** (2:52)
It was horrible.

**Fred Wilson** (2:52)
You can show up in San Francisco and all your friends be like, let's go to a Warriors game. No, no, no, thank you.

**Michael Mignano** (2:57)
Yes, some of those people who were outside of MSG rioting have become like famous.

**Fred Wilson** (3:02)
I know.

**Michael Mignano** (3:03)
Like one of those guys is in Marty Supreme now.

**Fred Wilson** (3:05)
I saw that.

**Michael Mignano** (3:05)
Yeah. It's crazy.

**Fred Wilson** (3:07)
I love that by the way. Well, Shalime is like a huge Knicks fan.

**Michael Mignano** (3:10)
I know. I know. I know. I know. It's really cool.
So I would like to show you something. Something we have never talked about.

**Fred Wilson** (3:18)
All right.

**Michael Mignano** (3:19)
And I'm a little nervous to get your reaction.