Zibby interviews venture capitalist, political strategist, philanthropist, and writer Bradley Tusk about OBVIOUS IN HINDSIGHT, a funny, eye-opening political satire about a campaign to legalize flying cars in major American cities, featuring a flying car startup and its various opposition groups (including Uber, socialists, transit workers, and the Russian mob). Bradley provides a fascinating look into the real workings of politics and technology, drawing from his extensive experience in both fields. The interview also touches on Bradley’s venture capital work, where he helps startups navigate regulatory challenges, his personal bookstore venture, P&T Knitwear, and his broad interest in reading, particularly contemporary fiction.

Transcript:

Zibby Owens: Welcome, Bradley. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss your book, Obvious in Hindsight. Welcome.

Bradley Tusk: Thanks for having me.

Zibby: You’re welcome. You’re obviously so much more than just an author. Although, I think that’s a pretty big deal. I’m excited to talk about your bookstore and your whole career and everything. First, Obvious in Hindsight, tell listeners, why this book? When are we supposed to expect flying cars? I don’t know.

Bradley: First of all, flying cars are coming sooner than we think. When I started this project, it was like, what would be a fantastical thing to write about? Since then, they’ve made insane progress. They’re starting to get permits for testing and things like that. The book is about a campaign to legalize flying cars in New York, Los Angeles, and Austin. On one side is the flying car startup and their vicious political consultants. On the other side is Uber, the Audubon Society, the socialists, the transit workers, and the Russian mob. The point of the book is to try to show people in a hopefully very fun way, here’s why decisions are really made in politics. Here’s how decisions are really made in tech. If you want to be in a position to understand what’s going on and potentially do something about it, you have to know how these people actually think. That’s what I try to show in the book based on the fact that I spent the first twenty years of my career in politics and now run a venture capital fund. I’ve lived both of those worlds.

Zibby: What would we not know from the politicians and everybody? You get kind of a bad rap, right?

Bradley: It may be deserved, actually. I’ve worked in city government, state government, federal government, legislative branch, executive branch. I’m a lawyer. I’ve really seen this thing from every conceivable angle. The lesson’s pretty simple. Every policy output is the result of a political input. Every politician makes every decision solely based on reelection and nothing else. If they think that you can either help them win their next election or if they don’t do what you want it could potentially cost them their next election, then they’ll work with you. If you can’t convince them of one of those two things, you are irrelevant. I wish human nature were different than that. Sure, there are exceptions. I worked for Mike Bloomberg for a long time. He’s clearly an exception to it. By and large, this is how politicians are. This is how politics work. If we want different outputs, we got to change the inputs.

Zibby: That’s so depressing.

Bradley: Thank you.

Zibby: I like to believe it’s not that, but it is.

Bradley: No, it is. It is.

Zibby: Okay. All right. Well, great. When you thought about turning this idea — the whole book is a “show, don’t tell.” How do you exhibit all of these things? How did you come up with this particular thing? Then what was the most fun to write about?

Bradley: Originally, this started off as a TV show. I was working with Steven Soderbergh, the movie director, on a totally political thing that he needed to get done from a regulatory standpoint for a company that he owns. At the time, I had written my first book, The Fixer, which is a memoir about my time in tech and politics. The galley came out. I gave it to Steven and said, “Hey, I would just love your opinion.” He said, “Okay. I’m flying to London tonight. I’ll read it on the plane. I’ll let you know.” I wake up the next morning. He says, “We got to make this a TV show.” Amazing. Steven Soderbergh wants to make a TV show with me. That’s the greatest thing ever. I start thinking about, what would a fictionalized version of The Fixer look like? I knew it had to be around some kind of campaign because you can tell a really good story around a specific campaign. Flying cars, at the time, was like, okay, it’s not impossible, but it’s also not happening tomorrow, so it can be a fun way to go about this and still show how politics really works but in a really entertaining way. I wrote the pilot with Steven, then wrote the next nine episodes. We had our big meeting at Apple TV to pitch them the show on March 10th, 2020.

Zibby: Oh, no.

Bradley: Little bit of a global pandemic in the way. The show kind of went away. I really loved the characters and the concept. I started to try to convert it into a novel and started working on it and worked on it and worked on it. You’ve written a novel, so you know how this is. Eventually, got it to a point where somebody wanted to publish it. I’m really excited.

Zibby: I don’t know why you can’t just bring back the whole show. Is it really too late?

Bradley: No, no, we’re working on it right now.

Zibby: Okay, good. Not like you needed my encouragement for that, but I’ll just throw my hat .

Bradley: Nonetheless, it’s nice to hear it. In fact, if the book reads a little bit like a script, that’s why. It was written that way first.

Zibby: Interesting. Go back a little bit. When did you get into the whole political sphere? Did you ever want to just be the president? Have you given up on that? Are you so jaded now?

Bradley: I think I’ve given up on being president. Look, when I was a kid, I just had this strong view, mainly, in large part, because I was this misfit that didn’t really fit in, that I didn’t want to live an ordinary life where you have a good job and live in the suburbs and have two and a half kids and retire at sixty-five to play golf or whatever it is. That just didn’t interest me. I felt like it would be more meaningful to me if whatever I did had a broader impact on the world. Politics was clearly the way to do that. I got into politics in a really lucky way. In 1992 — I’m dating myself — the Democratic Convention was at Madison Square Garden in New York. I was eighteen years old. I had just finished my freshman year of college. My family are immigrants. We don’t know anybody, have any money, or anything like that. My dad had a friend who was a lawyer for the carpenters’ union. This guy, Brian O’Dwyer, was a lovely man, knew I liked politics. He called me and said, “Hey, would you like a one-day pass to the convention, a carpenters’ pass?” I said, “Sure.” If you look in the newspaper, it says, “Convention: noon to midnight.” Having now been to a few of these, it’s really like eight to ten PM. I didn’t know that. I show up at noon at the Garden. It’s empty. It’s two dudes running for state rep in Montana speaking. For some reason, Ed Rendell, who at the time was the mayor of Philadelphia, was sitting in the audience by himself. I was pretty nervous. I was like, you know what? He’s a Jewish guy from New York originally. So am I. He’s the mayor of Philly. I had just finished my freshman at Penn, so lived in Philly. I said, let me just go say hi. What’s the worst that could happen? Rendell, of course, was probably just literally talking out loud to the empty chair until someone showed up anyway. He was happy to have an audience.

We talked for fifteen minutes or so. He said, “Look, when you get back to school, are you really busy?” I said, “No, not particularly.” He said, “Would you like an internship?” I said, “That’d be amazing.” He said, “Send me a note. We’ll set it up.” I go home. I write a letter. Every day, I’m checking the mailbox. What I know now but didn’t know then is that correspondence is the black hole of government. Everything goes in. Nothing comes out. I never heard back. I get back to school. This was a decade before 9/11, so security was not what it is today. To show you how naïve I was, I thought, all right, I’ll just go see him. I showed up at city hall and started wandering around. I found his outer office. I said, “Is the mayor here?” They looked at me like, that’s a crazy question to ask. You can’t just show up and ask that. The people who do either are genuinely crazy or they’re protesting. I wasn’t protesting anything. I didn’t look genuinely crazy. These old ladies from South Philly, they were like, “He’s not here, but you can leave him a note.” I write a note. I explain. Then I’m on the subway back to the dorm. I’m like, you idiot. You can’t just do that. Forget it. Cross it off the list. Then, get in the dorm. Twenty minutes later, the phone rings. It’s Ed Rendell. He said, “When are you coming to work?” I said, “I’ll be right there.” I worked for him all through college.

Zibby: Oh, my gosh, what a great story. That’s amazing. Then why venture capital?

Bradley: Spent the first chunk of my career directly in politics culminating with being Mike Bloomberg’s campaign manager for mayor in 2009. We won. Coming off of that, I started a consulting firm, traditional political consulting firm. You’re Walmart. You’re trying to open up stores in four major cities. You’ve got union issues, zoning issues, community issues. We figure all that stuff out. I was sitting in a meeting in early 2011. A friend of mine called and said, “Hey, there’s a guy with a small transportation store up. He’s having some regulatory problems. Would you mind talking to him?” I become Uber’s first political advisor that day. I get really lucky when Travis calls me back and says, “Listen, I can’t afford your fee. Would you take equity?” I had no idea what equity meant, but thank god I said yes. That was back during the series A.

Spent the next few years mainly running campaigns all over the US to legalize Uber and ridesharing. It worked. We figured out that we could turn our customers into kind of a political force and mobilize them through app. Did it again for Clear to get them into airports. Then I met my partner. He was running Blackstone’s at the time. You wouldn’t know him because that was very low level. The problem is, they were rounding errors at Blackstone venture capital. Jordan wanted to have his own fund. We started talking about, if you really understand regulation, you could do something about it. Would that make you a better investor? Off of that thesis and the Uber experience and Jordan’s experience at Blackstone, we went out and raised our first fund in 2016. We’re now raising fund four. We invest in all kinds of startups in regulated industries, not only to give them money, but then we run all of the political efforts for them, whether it’s legalizing FanDuel or prescription via text for Ro or getting the insurance licenses for Lemonade or whatever it is. Basically, I live in real life the story that you see in this book.

Zibby: Wow. You’re just Mr. Red Tape. If there is red tape, you know how to take it off.

Bradley: I wrap myself in it, absolutely. It’s funny. I don’t have this libertarian view that all regulation is inherently bad. I think some is good, some is bad. When it’s regulation aimed at the best interests of the consumer, that’s great. What often happens, though, is that whatever entrenched interest is regulated, over time, builds up so much political power that the regulator, instead of looking out for the average person, looks out for the really crappy taxi owners instead or the casinos instead or the hotel lobby instead or whatever it is. Then there’s a big fight because a startup has a better way to do it. They get a lot of political pressure from the other side. Then we come in and hopefully solve the problem.

Zibby: Amazing. I know who to call next time I want to start a business in a regulated industry. You never know when that’s going to happen.

Bradley: Luckily, as I’ve learned, other than getting our tavern license to sell beer and wine at the café, have not had to do much politics at the bookstore.

Zibby: Exactly. Tell me, did you always want a bookstore? I always wanted a bookstore.

Bradley: Yeah, always wanted one. Until Uber, really, I never had any money. We didn’t grow up with a lot of money. I worked in government. Never made a lot of money. It was just sort of like, wouldn’t it be cool? Then all of a sudden, I got lucky, and I did make a pretty good amount of money pretty quickly. When COVID hit, I started something called a Gotham Book Prize with my friend Howard Wolfson. We give fifty grand a year to the best book set in New York City that year. I started working with authors on the jury and the nominees and really enjoyed it and said, what else can I do in this space? At the same time, the city was getting ravaged by COVID. We lost 600,000 jobs. I realized, look, if you’re going to do something nice for New York City from a retail perspective, you could do it when you retire or you could do it right now when the city really needs it. That led to me finding this space on the Lower East Side and opening a bookstore.

It’s got a funny name. The reason why is, when my family came to this country in the 1950s from the refugee camps in Germany — if you were an uneducated Jew and you didn’t have any other type of job, you could always work in the garment business. My grandfather and a guy that he knew in the refugee camps both came here around the same time. They opened a three-hundred-square-foot sweater store on Allen Street called P&T Knitwear. When I signed the lease for this place — we’re on Orchard between Houston and Stanton. I texted my dad and said, “Where was that original store?” I knew it was around here somewhere. He told me. I said, “That’s the next block over. What was it called again?” He wrote, “P&T Knitwear, but you can’t name a bookstore P&T Knitwear.” Of course, I now own a bookstore called P&T Knitwear. We are also the only free podcast studio in New York that anyone can use. You just go on our website and sign up for it. We’ve got an event space. We’ve got a café. We’re a cool indie bookstore. It is a labor of love, as you well know. It’s been fun.

Zibby: That’s amazing. I love that so much. Were your grandparents in the concentration camps as well, or they just —

Bradley: — Everyone else was. My grandfather, he grew up in a town called Łódź in Poland. was super orthodox. He was the rebel of the family. His rebellion was to join the Polish army. He was fifteen, but he lied about his age. When the Russians invaded Poland, Poland lost in thirty-six hours. He got captured and sent to Siberia as a prisoner of war, which sounds like the worst possible thing that could happen to you, except all of his eleven brothers and sisters and parents ended up at Auschwitz and died in the camps. Because the Nazis never made it as far as Siberia, he survived. My grandmother was from Odesa. Her father was shipped into the Red Army, died in the war. They fled the Nazis as the Nazis started coming into Russia, also went to Siberia. She somehow met my grandfather there. The war eventually ended. He was freed. They had my father and made their way back across Europe and then ended up in the refugee camps for years in Germany. Then finally, a cousin in Brooklyn sponsored them for a visa, and they came here.

Zibby: Oh, my gosh. All these stories, it’s just amazing how life goes one way and not the other way.

Bradley: By the way, there are so many little variables. I’ve had so much luck. I think about that a lot. If this thing went just in one direction instead of the other or this call didn’t happen or this person wasn’t there, who knows? It probably wouldn’t be this.

Zibby: When you do your podcast, what are the conversations you are most excited to have?

Bradley: My podcast, it’s tech, politics, and the pursuit of happiness. It’s really that intersection of tech, regulation, politics. On a typical episode — on the one we did on Tuesday, for example, I had my chief of staff on, who’s a millennial, very left wing, about why the DSA has been pro-Hamas. Then I laid out my plan why New York City should have a city manager. Then I laid out my pedestrian rules for the road of how people in New York City should and should not walk so that we can save a little bit of time. None of those were actually tech oriented. Usually, it’s that plus some combination of some big tech thing, whether it’s Tesla or Apple or Amazon or Uber or whatever it is. Then we have guests on, typically either from politics or tech, who talk about the company they’re building, the idea they’re pursuing, the thing they’re trying to change. I’m not a journalist by any means. They’re very positive interviews. It’s called “Firewall.” We’re on twice a week, about thirty minutes each episode, no ads. You can find it on any platform.

Zibby: Amazing. Then when do you find time to read? I’m assuming you do with the bookstore.

Bradley: I read a ton. In fact, I read a ton, and then I make a list of — I assume you do this also — the books that I read. I finished number fifty-one this morning. It was nine nonfiction, forty-two fiction. I read a lot of fiction. The dirty secret is I read a lot on my Kindle. As a bookstore owner, I’m really not supposed to say that or do that. For me, it is really efficient. I also just walk into the store and grab whatever I want and walk out too. I read paper as well. I read a lot of contemporary fiction. In fact, one of those fifty-one books was yours, which I loved.

Zibby: Thank you.

Bradley: Devoured it, by the way. It’s a wide variety of stuff. It could be stuff that’s considered to be kind of literary fiction, like Demon Copperhead or The Heaven & Earth Grocery Store, books that have come out this year that I’m sure you’re selling lots of copies of. The book that I finished this morning was the new John Grisham book. I remember loving The Firm when I was really young. Read the sequel. It’s mainly fiction. It’s mainly contemporary. The other thing I would say is I have a very quick trigger finger. Let’s say I end up reading this year, sixty-five books. I will have probably started 130. If by page forty I’m not into it, I’m out. My view is life is too short. There are too many books to make myself read something I don’t want to read.

Zibby: I have the same philosophy, but if everybody loves a book and I can’t figure out why, I read a little more.

Bradley: Did you read Trust by Hernan Diaz?

Zibby: I didn’t. I have to. I just got this paperback, actually.

Bradley: Look, everyone loved it. It was one of the finalists for the Gotham Book Prize last year. I didn’t dislike it, but I just was like, there must be something wrong with me. Why does everyone think this book is so amazing? I just didn’t see it. It’s all subjective.

Zibby: I know. I feel like that a lot too. I’m like, well, I passed on that book, and now it’s the biggest seller ever. You know what? Those books, I still don’t want to read. It is what it is.

Bradley: In a weird way, it’s not unlike venture capital. I sometimes pass on companies that go on to be really successful. It’s got to be founders that I want to work with and ideas that I’m interested in. If I’m not, it doesn’t matter.

Zibby: What is your next thing, your next innovation, your next project? Another book?

Bradley: Mobile voting. I’ve got a book coming out on this next year from Sourcebooks, which is a Random House imprint. In fact, the file edits are due on Friday.

Zibby: Good luck.

Bradley: Thank you. We’re pretty close. A lot of stuff that I’ve already talked about on this podcast. I spent all this time in politics and learned that every policy output is the result of a political input. Then I ran these campaigns for Uber and saw that the same people who were never voting in city council primaries, state senate primaries, things like that, were willing to advocate for us because they could do it from their phone. The question was, what if we could vote this way? Wouldn’t that really increase turnout? The problem we have right now is because of gerrymandering, the only election that ever really matters is the primary. Primary turnout in this country is typically ten to fifteen percent. Who are those voters? They’re the furthest left wing. They’re the furthest right wing. They’re special interests that can move money and votes and will turn out an election. The message to politicians is, you’ve got to be ultra-pure. That’s why we see this craziness right now in the republicans not able to pick a speaker. Everyone has to be so ideologically extreme because the few people who actually do show up to vote, that’s what they want. My view is politicians will do whatever they need to do to stay in office.

Let’s say you’re a republican congressman from Florida. Turnout in your primary is twelve percent. Half of those voters are NRA members. You’re never going to vote for an assault weapon ban because even though you know intellectually that it’s crazy that someone could walk into a store and walk out with an AK-47, you also know that you would lose your seat immediately if you said that you were for it or at least you would think about it. As a result, it never happens. Imagine if turnout in that same primary were thirty-six percent instead of twelve percent simply because we made it much easier to vote, then just based on all the polling we see around assault weapons, your view would flip because you want to keep your job, and you would only keep your job if you supported an assault weapons ban. If we want the views of the majority to become our laws, to become our policies, if we want the two parties to actually work together and get things done, we’ve got to empower them to do so. They’re only going to do it if they feel safe politically. They’re only going to feel safe politically to do that if turnout is exponentially higher in primaries.

In 2018, I created this thing called the Mobile Voting Project where we started funding elections in different states where either deployed military or people with disabilities were voting in real elections on their phones. We ended up paying for seven states, twenty-one jurisdictions to do these elections. They were all independently by the National Cybersecurity Center and came back clean. Turnout, on average, doubled. City of Denver did a poll. The people who participated, a hundred percent said they preferred it. Of course, you prefer to do something on your phone than having to go somewhere. The cybersecurity community was very worked up that it wasn’t secure enough. In 2020, we started a tech bill to build our own mobile voting technology funded out of my foundation. Three years and ten million dollars later, we are just about done. We are going to release the software next January. It’s going to be free and open source. Anybody who wants to use it can have it. People can build on it. Then I’ve got a book coming out about it. The next step is really to hopefully, and it’s going to be really hard, but build a movement to demand this. Ironically, if you want to unite the parties, the one thing that will bring republicans and democrats together, as well as every union and every lobbyist, every trade group, is to change the system and make it more like they could lose power. The only way that we’re going to win this thing is that I can get millions of people in Gen Z and Gen Alpha, just like we got for Uber, to demand it. That’s the next big thing, is rolling out the mobile voting technology and hopefully building this movement so that we can make it happen.

Zibby: That’s amazing. I wonder that every time I’m there. I’m like, there has to be a better way. What on earth?

Bradley: There is. There is. There is. We have built it. We will be sharing it with the world very soon.

Zibby: Amazing. I’m just going to follow along with all the things you invent forever. You’re looking out for the maximum efficiency of the rest of us. Thank you for that.

Bradley: It’s fun. Look, to your point about sliding doors and everything else, I got lucky in a lot of ways from being able to be born in this country and be free and safe, different opportunities that came along over time, and lucky to make some money. My view is I just want to do the things that really interest me and use the resources I have to do things that I think are important, especially if they’re things that other people aren’t taking on. As a result, the stuff that I do looks pretty weird and random but makes sense to me. I like it. If you go to bradleytusk.com, you can get updates on all the different stuff we’re doing.

Zibby: I did not say it was weird and random.

Bradley: No, I think.

Zibby: Okay, just to be clear.

Bradley: I think most people think it is. You understand it. Hold on. One might think that someone who chooses to open up an indie bookstore and write a novel and do the podcast and all the stuff that you do might also be a little weird. You may not be the best judge.

Zibby: Fair. Fair point. I’ll take it. Bradley, thank you so much for coming on. Congratulations on your book.

Bradley: Thanks for having me. Thank you.

OBVIOUS IN HINDSIGHT by Bradley Tusk

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