I was really young. The best thing that happened to me was, AOL was in a period of deep decline, and they were firing everybody in sight. They would obviously fire the people that were getting paid the most, which roughly equated to the people that were the oldest, and doing the least. And what was left over were all these young people, and we would just get increasing responsibility because they just didn’t have an alternative.
I tell people now that was the luckiest thing that happened to me in many ways. When things work, I think a lot of people pretend they know what happened, but you actually learn more when things aren’t working. You know what your effort hasn’t done, versus, what could have been a whole bunch of things has done.
Was it your effort? Was it timing? Was it skill? Was it an accidental PR thing?
Twitter blew up — if you remember, I mean literally, and no offense to Ev and those guys — but not because of those guys, I mean that team has done more to retard the progress of Twitter. It blew up because Fred Wilson and those guys decided to blow it up at South by Southwest.
We had the fail whale constantly, and infighting. All you do in success is conflate luck and skill, but in failure you learn why all of these things aren’t working. You learn how to build a better team. A small, lightweight, fast, nimble team.
You learn how to try and iterate and test stuff. You learn how to celebrate failure because most things aren’t working. And you keep trying stuff, and trying stuff, and trying stuff, and you just dispense with the ego.
I was surrounded by these people that were credentialed. They had all these degrees, they were just able to check all these boxes. They had a name that was pronounceable. Like all this shit, and they were fucking morons. You just realize, that’s just not what it’s about.
I look at this [room] and I see an unbelievably diverse group of people. You people are gonna take over the world, you people are what I was 10 years ago. And there’s this establishment change that is happening now.
And so for me, what I learned was that establishment change has to happen.
And so that’s what sustained me, because I was like… I’m a little frustrated, but I’m learning. And I’m getting self-confidence to realize what the old parochial white man tells me, is not right: “He don’t know what the fuck’s going on.”
That’s a huge realization, and everybody’s realizing this in their own, sort of, personal shape and form now. And so we’re unlocking different parts of people’s brains to be able to think they’re capable of anything. I felt that at AOL. But the problem was, I didn’t feel it enough of a way. So when I got offered a job to go and work at Mayfield, I took it because I went back to the same patterns that I was exhibiting when I took that job at Bank of Montreal.
It’s the job that people wanted. It’s what society tells you is important. It’s the hardest seat to get.
But I walked in there and I thought within two months, “Wow I made a huge mistake.” I played to the rules of the man.
I didn’t listen to my own gut. I didn’t have a way to tell my parents why something else I was doing wasn’t the right [thing.]
Today, it’s the easier it’s ever been for you guys to be independent, you know, because you can point to success cases that validate the choices you’re making.
Six years ago, there were fewer of those. Ten years from now there’ll be even more, because a bunch of you guys will be crushing it. So it’s gonna get easier, and easier, and easier. But at the time, it was hard for me.
I grew up on welfare. How do you tell your parents, “Listen. I had a job making a lot of money, and I quit.” And I was making not that much. Then I finally got promoted at AOL, I’m making a couple hundred thousand dollars a year, I quit again.
So every time they’re like, “Okay, economic light right around the corner, right around the corner,” I left!
It just seemed like that’s not what you do. You get in a seat… and for them, the idea that you’re an executive, I was 27 years old. “You’re an executive, at this company, that’s known. That’s everything!” And to me, it was nothing.
And I just didn’t have the courage to do anything about it. And then, this Facebook thing, I finally just said, “I just gotta follow my gut.” My instincts were telling me this is it. Something is here. And I made the most important and the best investment of my life, which is I made a choice of my time.