Internet History Podcast | The Life And Career Of Bradley Tusk Of Tusk Ventures

I was sitting... I started my first company, Tusk Strategies, in 2010. It's a political consulting firm that runs big legislative and policy campaigns all over the US. And I was sitting in a meeting in early 2011 and a friend of mine called and said, 'Hey, there's a guy with a small transportation startup. He's having some regulatory problems. Would you mind talking to him?' I became Uber's first political adviser that day. And then when Travis Kalanick called me back — Travis was the founder and CEO — he said, 'Listen, I can't afford your fee. Would you take equity?' I didn't know what equity meant, but for some reason I just heard myself saying yes. And that meant I started getting stuck in Uber very, very early on. But more important, it meant that became my job to legalize Uber in New York and then markets all over the US.

Yeah. Hey, Brian. Thanks for having me.

Oh, it's definitely politics for sure. You know, that came first, right? Yeah. And I think I'm kind of much more of a political junkie than a tech junkie for sure. But the funny thing I've noticed though is that people who work in politics now see me as like a tech and business guy, and people who work in tech see me as a political guy. So wherever you are, you assume I'm the opposite.

Or maybe not, actually.

Well, so when I was in college, I was actually in the creative writing program, but at the same time, I had worked for the mayor of Philadelphia, Ed Rendell, all through college. And so I kind of hit that point towards the end where I'm like, okay, I could probably pursue a career in either of these. And I really liked both a lot. And my thought process was, I was a pretty good writer, but like my ceiling would have been like a showrunner on a sitcom. I probably would have done just fine doing that, but that was my ceiling. I wasn't going to win the Pulitzer Prize. I wasn't going to win the National Book Award. Whereas with politics, I felt like, who knows what I could do. And so I pursued that instead. And I got incredibly lucky that the things I did in politics were interesting enough that I ended up being able to write a couple of books anyway. But definitely politics.

Well, I grew up in Brooklyn and Long Island, and then came back after college, came back again after law school, and other than four very crazy years back in Chicago as the deputy governor of Illinois, I've really been in New York the whole time. And when you talk about sort of true loves, what I really love is New York City politics even more than state or federal.

I did. I did.

The StarQuest. Yeah.

It was how municipal government works, I would say. So in the sense that Henry was appointed — he had been an elected official, city council member, earlier in his career. I got an incredible education from Henry as to how city government works, how the levers of power work, how to get things done even kind of around the system as opposed to sort of working through the bureaucracy. You know, what was incredible about Henry, that was both wildly irresponsible and yet wildly effective, was he just hired all these young people from these really good schools, paid us 22 grand a year, and said, 'Okay, go run whatever at the parks department.' And the good news is he got really talented people, you know, for very little money, working 80 hours a week. He definitely violated all kinds of civil service rules along the way, and then the city ended up paying a big fine because of it. But I got a great education in kind of what makes people tick. And the thing that I really realized — I was Henry's spokesperson — is Henry was like most politicians, which is he desperately, desperately needed as much affirmation and validation as he could possibly get. And seeing his face on TV, reading his name in the newspaper is what provided it. And so because I was this press guy and I was pretty good at it, it gave me a sense of like, one, okay, here's the kind of power and influence that I could have with this skill set, but two, here's what makes these guys tick.

The parks was two stints. It was sort of '95 to late '96, and then again like '98, '99 or something like that.

I'll give two different ways to answer that question. So the first is, yeah, look, I was, you know, early 20s, so I think I probably had — you know, I would have had a ton of energy in any scenario. But you combine that with New York, where we had a job where the commissioner worked 24/7 literally, and there's stuff that happens in the parks 24/7, right? And so like I was working probably a solid 80 hours a week, but also I was, you know, young in New York City and I was going out every night till 3 in the morning and sleeping very, very little. And I just, you know, I was at the age where I had the energy to burn the candle on both ends. And then, you know, from a city governance standpoint, Rudy — while he ultimately sort of lost his mind — you know, he did some really innovative things in government. And so, you know, being part of some of those things and that experimentation was really exciting and it felt really meaningful. And then right around the same time, you had the kind of emergence of the dot-com era in New York City. I think my first exposure to it — I don't remember if this was — Kozmo.com.

And it was like they would deliver you anything.

And it was effectively like free. Like you didn't have to pay. You couldn't tip them. It would cost like half of what it normally would cost.

Yeah. And I remember being like, 'This is amazing. How does this work as a business?' And of course the answer was it didn't. The guy named Matt Higgins, who's since become a successful tech guy and a judge on Shark Tank, but was in Rudy's press office, went to Kozmo. He was the first person I knew that went into the startup world, and he's done really well. I just spoke to Josh Harris of Pseudo.com fame, and so we were talking a lot about like, again, the money coming in, the parties downtown, the art scene, but also like the tech scene. And like, was there a sense at the time that New York City was becoming a tech hub? Well, I don't know that we even had a sense of tech hubs at that point, but you could tell that there was something happening. And to me where the two really coalesced was fast forward a few years when Mike Bloomberg became mayor, because then all of a sudden you had the organic tech scene and industry develop in New York City along with a mayor who came from tech, is a trained engineer, and identified, hey, one of the things I want to try to get done in my time here is to diversify the city's economy, and to him it was very clear that that other sector should be the tech sector. And so he started actively really pursuing it and saying, 'Okay, I want to make this a thing.' So then you had the marriage of something happening already because the market allowed for it, and then the government with all its resources saying, 'We love this. We want to really grow it.' And that's when I think all the fuel was added to the fire.

Yeah. I mean, really what I learned in working for Chuck — and look, it was an incredible learning experience. It was a two-year PhD, effectively, in how media works, how politicians work, how they think, what motivates them. And Chuck was sort of Henry Stern times a million. And Chuck was easily at the time the most sort of media-friendly and hungry member of Congress. My guess is at this point now, maybe some people have surpassed him, but so we just did vast amounts of press for Chuck every single day, of course, culminating every week with his famous Sunday press conference. I think in the 104 Sundays that I worked for him, I got one off for my wedding and one for my honeymoon, and I did press conferences the other 102. And you know, what I realized was, one, if you could come up with clever ideas, people would cover it, talk about it. You know, the press sort of had its need to sort of deliver somewhat entertaining content that seemed important. And at the same time with Chuck, if I could come up with ideas that would get him attention, that became the legislative agenda, because the thing that he cared about the most was getting on TV, getting his name in the newspaper. And because I became the person who could like think of stuff that the press would then want to talk about and cover, effectively, if every Sunday plus the rest of the week you have to announce something, that effectively becomes your agenda. At the same time, I don't think we passed a single bill in the two years that I was there. It almost felt besides the point. You know, the point was this Kabuki theater, of which, you know, we worked incredibly hard at it and it felt important, but in reality, if not for 9/11, I don't know that a single thing that I did in the 24 months I was there had any real-world impact whatsoever. But 9/11 did happen about almost exactly halfway into my tenure there. And that became a point where, one, the people just really needed to see their leaders and elected officials out and about and on the case as much as possible. I wonder if in today's world that would be the same, but it was the case then. And two, I remember we were trying to get $20 billion in funding for New York, which is such a — it's almost cute now because it's like the amount you get after there's like a fire and then for reimbursement, but at the time it was sort of the biggest, you know, amount that had ever been given. So getting all of that and some of the subsequent 9/11-related legislation through Congress was really a big deal.

Yeah, for sure, because I'm running all of it. So, you know, I'm 29 years old. I'm sitting — at this point I'm working at City Hall for Mike Bloomberg. We all sit in a bullpen with Mike in the middle, and I'm sitting in the bullpen and my phone rings and it's a guy I knew from Washington, and he said, 'Hey, do you want to be the deputy governor of Illinois?' And I said, 'What's a deputy governor and why are you calling me?' And the answer was, 'It's the person that runs the state.' And insanely enough, I got this job where — and by the way, there's just one deputy governor. Like in New York City, there's like seven deputy mayors at any given time. So I was in charge of the state's budget, operations, legislation, policy, and communications. And that meant every dollar, every employee, every policy, every program, every everything. And of course, a logical person might be wondering, why would you give a 29-year-old from New York that much responsibility, especially in a place where he really didn't even know? And I think it was a mix of a few things. I think the governor was a guy named Rod Blagojevich, who certainly made himself famous later. And he was so crazy that they understood that they needed someone really young who would view this as a career-making opportunity and would put up with any of his sort of nonsense to be able to have that job. And I did. But I got there and I remember my first day being told, 'Okay, there's a $4.8 billion budget deficit. You know, figure out what to do about it.' And working with the budget director, a lot of people around the clock, we — you know, Rod gave us some broad dictates, which was, I don't want to raise taxes, I don't want to cut funding for schools or healthcare or public safety, but make the budget deficit go away. And that, you know, that certainly meant we had to be pretty creative. But really I spent a good chunk of my time over the next four years figuring out what the budget should be, how to pass it, how to legislate it, negotiating it with the speaker and the Senate majority leader. And the same thing with the policy agenda. You know, and Rod was a very, let's call it, absentee governor. Rod had this view of politics that was both completely insane and yet also wildly logical, which was the job of running for office and the job of holding office were two totally different jobs. And his job was running for office. And he genuinely believed that by winning he did his job. He's like, 'I'll see you again in four years.' And that meant he had virtually no role whatsoever in the actual governance. So, you know, for the State of the State, which would be the speech he would give that would lay out all of our legislative priorities for the session, I'd write the speech. We'd figure out what we wanted to do. I'd write the speech. I'd hand it to him and say, 'Hey, you're going to deliver this off the teleprompter to the legislature on Tuesday.' And he would do so brilliantly, by the way, and wildly talented guy. And then go back to Chicago and watch Cubs games and exercise and do all the stuff that he liked to do. And it was my job to try to pass all these bills and run the state. So, yeah, it was an incredible learning experience. It was not easy because Rod was not an easy person, and luckily I never really got caught up in his corruption stuff, but he did once slip up and ask me to do something illegal, and fortunately I knew not to do it and reported it, so I didn't get in any trouble. But as a result, I did have to testify against him at his trial.

For sure. Because I think in the Senate it was so performative that it just — there wasn't that much sausage made to the extent that it was. Chuck at that point was a very junior senator and wasn't really part of it. Now of course he is the sausage maker. And you know, in the Bloomberg world, the stuff that I did definitely gave me some sense of it. So like I ran the city's charter revision commission and I had to both get the process done and then run the campaign that won to change the city charter. So I learned parts there, but yeah, I learned more in Illinois about how politics work and really about how people work than anything I've ever done.

Yeah. By the way, the Lehman blip was pretty uninteresting. So feel free to skip it if you want. Like, I don't think in my memoir I even covered it.

Yeah. So, you know, after Illinois, I had this idea about privatizing state lotteries and took a job on Wall Street to try to do that. And in my great wisdom, picked Lehman Brothers. And Lehman Brothers, as everyone knows, both crashed and burned and took down the global economy with it. And the day that that happened, I get a call from Mike saying, 'I need to see you.' And you know, I remember him saying, 'What are you doing now?' And I said, 'Nothing.' And he goes, 'I know.' And he goes, 'Well, I feel like I need to run for a third term because the city is now in the middle of this massive fiscal crisis and economic crisis, and so I need to do it, but I need the council to allow me to run for a third term. So you're now the person in charge of passing a law to change that.' So that became sort of my immediate job. It was a hard process, but we won. Very controversial. Definitely made our margin a lot smaller in the subsequent election, but we did. And then I ran his mayoral campaign. And you know, it was obviously a difficult time in the country in a way, but it was also a really exciting time in the country too because, like you said, the tech sector was taking off in New York City, even if it took a couple of years for the economy to feel it. You could see the seeds of it happening. Obama took office and there was a lot of excitement around that. And what's interesting was there, you know, because it was the Mike Bloomberg campaign, which meant, A, he's a tech guy — you know, if you asked him the question politics or tech, he would say tech, right? He's a tech guy through and through. And we also just had unlimited resources. I remember like experimenting with like this thing called Twitter that just came out, or like making a Wikipedia page for him, or like, you know, all these things that obviously now are very, very, you know, old school, but at the time, you know, they were really at the edges of what was happening. And you know, he loved all of that and encouraged it as much for New York City as possible. And then I think in a way, you know, you had this sort of second tech boom come out, you know, not long after the Great Recession, and Uber and Airbnb and lots of companies. And I think one of the reasons that New York — you know, if you like those things — New York had them, is because Mike Bloomberg saw the potential of all those and said, 'Hey, you know, I know the taxi system sucks. Here's a better way to do it. Hey, I know the hotel system sucks. Here's a better way to do it.' If you were a Bill de Blasio type, your neighbor, then you probably would say that those things were all regretful decisions. But one of the things when you look at Mike Bloomberg choosing to run for a third term, changing the law, and everything else, I don't think that the tech sector in New York City is half as strong as it is today if he didn't have those four more years to really tend to it and grow it and prioritize it.

Yeah. I mean, just — I honestly, I'd love to say that I was a genius and I saw it and I made it happen. The reality is I fell into it. I was sitting — I started my first company, Tusk Strategies, in 2010. It's a political consulting firm that runs big legislative and policy campaigns all over the US. And I was sitting in a meeting in early 2011 and a friend of mine called and said, 'Hey, there's a guy with a small transportation startup. He's having some regulatory problems. Would you mind talking to him?' I became Uber's first political adviser that day. And then when Travis Kalanick called me back — Travis was the founder and CEO — he's like, 'Listen, I can't afford your fee. Would you take equity?' I didn't know what equity meant, but for some reason I just heard myself saying yes. And that meant I started getting stuck in Uber very, very early on. But more important, it meant that became my job to legalize Uber in New York and then markets all over the US. And you know, in many ways it was just an incredible education because I think even now when people think about the sort of archetypical tech regulatory fight and campaign, I still think they think of Uber. And in many ways it was David and Goliath. And we were David at the time, right? So the taxi — and now Uber is this $200 billion company, but at the time the taxi industry was incredibly politically powerful, incredibly wealthy. They didn't want competition. And we couldn't compete with them in terms of lobbying or campaigns or anything like that. And you know, we tried something that was really unusual, and thank God it worked, which was — and this is Travis's doing — he just said, 'I think our product is so much better than what taxi offers that if we ask our customers to fight for us, they will.' And I'm not sure he even knew what to do with it, but he had that thesis and he was right. And so I remember the first time actually was in DC. The city council had legislation that would have basically banned Uber. And we at that point, we had a list of our customers and we didn't even have like anything in the app yet. We just literally sent them an email saying, 'Hey, here's what's happening. And if this bill passes, you won't be able to use Uber anymore. So if you like it, would you please reach out to your council member?' And then we just listed like all of their names and numbers, like hopefully people would know which one was theirs. And 50,000 people reached out like in a week. And the council was so — usually a city council member, if they get like nine calls about something, that's a lot, right? And then all of a sudden they're getting like thousands. It's like, holy... So, not only did we beat the bad bill, we wrote our own bill and passed it unanimously. Even the sponsor of the bad bill ended up voting for our bill. And what that taught us was, wow, there's a lot of power in this thing. And then from there we started sort of, you know, making it better and building the functionality directly into the app to allow our customers to reach out to government. And in pretty much every market in the US it was the same playbook, which was taxi would come after us with the things that they knew how to do, is kind of the inside game, and you know, all the people that they give donations to, you know, telling us we had to shut down. And then us going to the people. And you know, what it really showed me — and this was the basis for the Mobile Voting Project afterwards — is if every policy output is the result of a political input, if every politician makes every decision solely based on...

next election, which is pretty much always true. You know, Mike might have been different, but by and large that's true. Um, then you just have to shape the equation differently, right? To the equation before what we did was you're a council member in Denver or New York or Seattle or wherever. The taxi guys give you a couple of grand per campaign cycle. You do what they want. Now, I just had 6,000 of your constituents who normally don't pay any attention to you whatsoever tell you, "Hey, I like this thing. Don't mess with it." And all of a sudden, you're just doing a cost-benefit analysis, and not pissing off 6,000 of your constituents is a lot more important than the couple thousand dollar contribution you got from the taxi industry, and the politicians flip. They will just do whatever they need to do to stay in office. That's it. Um, and so we sort of learned that, and in many ways I think the playbook that we did became sort of the standard playbook for the tech regulatory fights over the next decade.

Correct.