I was 18. If you look at the newspaper, it says the convention is from noon to midnight. Now, anyone who's been to a convention knows it's [really from] 8PM to 11PM, but I'm this gullible kid - I don't know that.
So I show up at noon at Madison Square Garden. It's totally deserted. There's two guys running for state representative of Montana on the stage and no one else, but Ed Rendell - who was the mayor of Philadelphia, and went on to be governor of Pennsylvania - was sitting in the audience by himself.
He’s this very gregarious, friendly guy. I said to myself, "Look, he's the mayor of Philly," and I just finished my freshman year at Penn, so I say, "Hey, I go to school in Philly." He's actually from New York and so am I, so I think, "What's the worst that could happen?"
So I go up to him and he's super friendly, because that's just how he is, and we talked for 10, 15 minutes. I realized my time should be up, I say, "Thanks so much, I really appreciate talking to you," and he says, "Are you busy after school?"
I said, "No, not really," and he said, "Do you want an internship?"
I said that'd be great, and he said, "Send me a note, we'll set it up."
I'm very excited. I go home, I write a letter. Every day, I open the mailbox, and there's no reply. What I know now but didn't know then is that correspondence is like the black hole of government. Everything goes in, nothing comes out.
I get back to school, but I'm still kind of interested in doing this. I had this weird thought that I'd go see him.
I go to City Hall - it's a decade before 9/11, so security's not what it is today - and I get not to his secretary, but to the outer office. I walk up and ask, "Is the mayor here?"
Now that I'm an adult, in retrospect, that's a crazy question. You can't just walk up and ask to see the mayor. But I was so young and naive that they kind of took pity on me. I wasn't protesting anything and I wasn't crazy, I was just sort of this nice young kid that didn't realize that you can't just ask to see the mayor of Philadelphia.
They said, "He's a little busy," so I said, "Is it okay if I leave a note?" and they said sure. I write a note and get back on the subway to go back to my dorm, and I’m thinking, "You idiot, what's wrong with you? You can't do that." I thought I'd blown that chance and it was never going to happen. Then I'm sitting in my dorm room about twenty minutes later and the phone rings. "Hold for the mayor."
He says, "When are you coming to work?" I said, "I'll be right there!"
And that was how I got started. Since then, I ended up working in multiple levels of government: city government for Rendell when I was in college, for the New York City Parks Department when I was out of college, and then for Mike Bloomberg at City Hall and running his mayoral campaign in 2009.
In state government, I spent four years as Deputy Governor of Illinois and two years on the Hill as Chuck Schumer's communications director. I also spent about two years at Lehman Brothers creating and running a group to privatize state lotteries, which had the impact of having me in every state capital about five days a week going from capital to capital. The net effect of all of that was that I ended up on this weird journey in New York, DC, Chicago, and Philly - and traveling constantly – and really understanding state, federal, and local government, but especially state and local government all over the country.
When I started my first business, which was a consulting firm, the idea was that we were going to run campaigns for big companies in multiple jurisdictions. No one was doing anything like that before. People would either work nationally or they had a specific skillset - they were a pollster or an ad maker - or they would do a lot of things in one market, like DC or Albany. I said I was just going to run campaigns, since it's what I'm good at, but I'm going to do it everywhere. And it worked.
So I'm doing this for the usual suspects: AT&T, Wal-Mart, Comcast, Pepsi, and so on. The pivot tack that brought us here was the day the phone rang and someone said, "Hey, there's a guy with a small transportation startup having some regulatory problems. Would you mind talking to him?"
This is early 2011, so I become Uber's first consultant that day, and I get even luckier when Travis [Kalanick] calls me and says, "Hey, I can't afford your fee. Would you take equity?" and thank God I said yes. He had a particular problem in New York. We solved that problem, and he said, "Can you do this everywhere else?" and I said yes, then we did it in Boston, Philly, Chicago, DC, Miami - the whole country. That's how I got started in tech - being Travis's political consultant. We built a big in-house team. I still work with Uber, but there's obviously a lot of people there to do most of the work now, so I just give my opinions and go on TV and talk about things, and that's fine.
About a year and a half ago, the mayor of New York City, Bill de Blasio, had this very ill-conceived idea to put a cap on Uber's growth of 1%. One of his biggest donors is the taxi industry, and they literally wrote the bill and handed it to him, then he submitted it to the city council.
I remember sitting in the Dallas airport. The phone rings, it's Travis, and he says,"Did you see what just happened?"
I say, "No, I'm stuck at DFW, it's raining, my flight's canceled, whatever."
He says, "Check it out and call me back."
So I go online, see what happened, and call him back. I say, "I have two questions: is there anything I can't do, and how much can I spend?"
To his great credit, he said, "Whatever you need to do and spend, just make sure we win."
We ran this very fucking vicious campaign, going after de Blasio incredibly hard from the left. We had drivers and passengers saying it was racist to take these opportunities away, we put a de Blasio mode on the app with a 25 minute wait time, we made it possible to click to contact City Hall.