#1277 Bradley Tusk on Insane Story Of How Startups Beat Politicians

Bradley Tusk is a venture capitalist, political strategist, writer, and owner of P&T Knitwear bookstore. In this conversation, we talk about his brand new book, called “Obvious in Hindsight.” It is all about a fictional story of innovative technology, flying cars, and what they have to go through with politicians, mafia members, etc. This is a great conversation about how technology meets politics, and the reality on the ground. ======================= Base is making it their mission to bring a billion people onchain. But what exactly is Base? It's an Ethereum L2 offering a seamless experience for both builders and users. With near-zero gas fees and rapid transaction speeds, Base is shaping the future of the onchain world. Base is a canvas for everyone, with hundreds of apps in the Base ecosystem, whether you're an emerging creator, a seasoned developer, or someone exploring the onchain space for the first time, Base is designed to bring your ideas to life. So, if you're looking for a platform where the future of onchain is being built daily, Base is your destination. Join in and make onchain the next online. Learn more at ⁠⁠⁠⁠⁠⁠⁠base.org⁠⁠⁠⁠⁠⁠⁠ and follow along on Twitter at @BuildOnBase to see cool things to do onchain, everyday. ======================= Trust and Will has simplified the process of creating and managing your will or trust online. They leverage a data-driven, design-first approach and amazing customer support to help you protect your legacy from the comfort of your home starting at just $159. Sign up today for 10% off using ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://trustandwill.com/pomp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ======================= Pomp writes a daily letter to over 250,000+ investors about business, technology, and finance. He breaks down complex topics into easy-to-understand language while sharing opinions on various aspects of each industry. You can subscribe at https://pomp.substack.com/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Anthony Pompliano?

  What's up everyone? This is Anthony Pompliano. Many of you know me as Pomp. You're listening to the Pomp Podcast, which is my effort to find the most interesting people in the world and sit with them for hours while I ask questions in an effort to learn. So it would mean the world to me if you would subscribe to the show on your favorite audio platform, watch episodes on YouTube, and tell your friends and family about the podcast. My goal is to help millions learn from the world's most interesting people. So let's get into today's episode. Bradley Tusk is a venture capitalist, political strategist, writer, and owner of PNT Knitwear Bookstore. Now Bradley has a brand new book. It's a novel called Obvious in Hindsight, and it's all about a fictional story of an innovative technology, flying cars, entering into various cities across the country

• 0:47Anthony Pompliano?

  and what they have to go through in terms of fighting off politicians, mafia members, and many others. Bradley and I have done multiple podcast episodes together, and each time I learn something all about how technology meets politics and the reality on the ground. He is one of the most sought after political consultants in the world, and he's continued to help companies from Uber to Bird to Lemonade and many, many more, figure out how to navigate the regulatory environment. Here is my conversation with Bradley Tusk.

• 1:16Speaker 01

  Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments. You should not treat any opinion expressed by Pomp or his guests as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only.

• 1:41Anthony Pompliano?

  Today's episode is brought to you by Base. Base is making it their mission to bring a billion people on-chain. What exactly is Base? It's a layer-two offering a seamless experience for both builders and users. With near-zero gas fees and rapid transaction speeds, Base is shaping the future of the on-chain world. Base is a canvas for everyone with hundreds of apps in the ecosystem, whether you're an emerging creator, a seasoned developer, or someone exploring the on-chain space for the first time. Base is designed to bring your ideas to life. So if you're looking for a platform where the future of on-chain is being built daily, Base is your destination. Join in and make on-chain the next online. Learn more at base.org or follow along on Twitter at BuildOnBase. Again, that's at BuildOnBase

• 2:26Anthony Pompliano?

  to see cool things to do on-chain every single day. Today's episode is brought to you by Trust and Will. I've gone through a number of different changes in my life over the last few years. I got married, I had a kid, and I had to start thinking about how could I ensure that my wife and my child would be okay if anything ever happened to me? That's where trust, wills, and estate planning come into play. Now, most people, what they do is they get introduced to a friend, an uncle, or someone in their local community. It tends to be someone who's really expensive, a lawyer, an accountant, or somebody who does estate planning, and they just simply are using a one-size-fits-all template and just telling you, "Pay me thousands of dollars and I'll use the same thing for you as the guy down the street." But that's not what Trust and Will does.

• 3:07Anthony Pompliano?

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• 3:50Anthony Pompliano?

  be the difference between someone being taken care of and someone not. Go check them out today at trustandwill.com/pomp. All right, guys. Bang, bang. I've got Bradley here. Bradley, you've got a brand-new book, "Obvious in Hindsight." It is a fictional novel, but I think it is really tied into your work with Uber, as Uber and others have gone into these cities. And there's kind of this, I don't know, competition, maybe this abrasiveness between the old world and how things have been going, and then these new world tech companies. Talk just a little bit, it's like, why did you want to write a novel? Most people I think expected you to do that.

• 4:26Speaker 02

  I know. So when I was in college, I was actually in the creative writing program, and I really loved to write. And I knew I was like, good enough that I could have made a living doing it, right? I would have written like sitcoms and been fine. But I knew I wasn't good enough to win a national book award or write a number one bestseller or anything like that. And at the same time, I was also working in politics all throughout college and felt like sort of the upside there was higher. So I pursued that instead. I wrote, and you know, because you had me on when I wrote this, I wrote a book called The Fixer a couple of years ago. That was a memoir about all of the stuff that I've done in tech and politics. So legalizing Uber and Lemonade and Bird and FanDuel and all of these different startups. And do you know who Steven Soderbergh is? He's like

• 5:10Speaker 02

  a movie producer, director. He made like Aaron Brockovich, Ocean's Eleven, Traffic, a bunch of stuff like that. Anyway, you know how celebrities like to buy liquor companies?

• 5:20Anthony Pompliano?

  Yes.

• 5:21Speaker 02

  So he bought a Bolivian brandy company. And from a regulatory standpoint, he had a couple of challenges. The first is that it's importation. The second is it's alcohol, which is highly regulated. And the third is Bolivia is a communist country that we don't really have any diplomatic ties with, right? And he needed a federal rule change at the Department of Treasury in order to do the business the way he wanted to do it. So we got introduced through a mutual friend. And he read The Fixer and he sent me a note and said, Hey, let's turn this into a scripted TV series. Awesome. So I started thinking about like, what would be a fun way to do this? And it clearly should be based on a campaign to legalize something because that's what I do. And the reason I picked flying

• 6:06Speaker 02

  cards was it seemed pretty fantastical and out there in the future. E-Tal has made so much progress from when I started this to now that actually it's much more present day. And wrote the pilot with Steven, wrote nine more episodes, and our big pitch meeting with Apple TV was set for March 10, 2020. As you can imagine, that didn't happen. And show went away. But I kind of liked what I had, the characters I created, the plot line, all of that. So let me see if I can turn this into a novel. It was really hard to do. In large part because it's just, I had no idea how to structure a novel and that just took forever to get it right. But eventually we did. Got it published. And the fun thing is Steven and I are now back on the TV show again.

• 6:50Anthony Pompliano?

  I love it. I want to kind of pull out some of the lessons from it. I know, again, I know it's fiction, but you are probably the world expert.

• 6:57Speaker 02

  Very barely fiction. Yeah.

• 6:59Anthony Pompliano?

  Yeah. You are the world expert. You have done this over and over and over again. And one of my big takeaways from the book was, okay, so I'm a founder. I have some, you know, brand new shiny technology or company. I'm going to go into one of these jurisdictions and most people think I gotta fight the regulators, right? And fight all uses just like they don't want me to be successful. I want to be successful. There's some sort of abrasiveness there. That seems like only the start of the problem. You have other competition. You have the mafia. You have all sorts of lobbying groups. Like just talk about maybe the apparatus that these founders are up against when they go into a city.

• 7:32Speaker 02

  So I'll give you the scenario in the book and then how it works in reality. So in the book, the book's about a campaign to legalize flying cars in New York, Los Angeles, and Austin. And on one side of the campaign is Flight Deck, which is the flying car startup. And then there are vicious political consultants, namely us. And then the other side is Uber, the Autobahn Society, the socialists, the transit unions, and the Russian mob. And it's satire and it's ridiculous. But like you said, it's not really ridiculous, right? Because the underlying motivations of why the founders in the book, the VCs in the book, the politicians in the book, the political lobbyists in the book, whoever is, why they make the decisions they make, those are all

• 8:13Speaker 02

  based in reality, right? And so when you think about this as the construct, whether you're Uber or Bird or Roman or FanDuel or Lemonade or all the stuff that we've invested in and helped legalize, there's really two buckets of work. And tell me if this gets a little too complicated. But the first is sort of the Uber situation, which is Travis did not invent the idea of paying someone to take you from point A to point B. Travis came up with a dramatically better way to do it, but he was competing with an entrenched interest in the taxi industry. And while we had these mega regulatory fights, what it really was, was us fighting with taxi through the guise

• 8:55Speaker 02

  of regulation. It was really a fight for market share, but couch As you know, legislation to either legalize us or ban us or whatever, whatever it was. So that's about half the stuff I would say that we work on, invest in. And then the other half, which is a lot of stuff that you focus on are sort of the white spaces where no one's ever done it before. So that can be crypto, that could be AI, that could be flying cars, that could be drones, whatever it is. So there's good and bad news, right? Good news is you don't have to take out some entrenched interest. Bad news is there is no regulatory framework, right? So you gotta make it up. And so in a certain way, if you take um the example autonomous vehicles versus flying cars

• 9:37Speaker 02

  or eVTOL is is in real life, kind of what what they call it.

• 9:43Speaker 02

  So you would think that autonomous cars, if I asked you or myself, I when we started writing this book, like, okay, in five years, what will be further along? Autonomous vehicles or flying cars, I think a hundred to nothing, we all would have said autonomous vehicles, right? You know, um, but you know, who's standing in the way of regulating autonomous vehicles, especially trucks? The Teamsters and Donald Trump saw himself as a Teamsters guy and Joe Biden sees himself as a Teamsters guy. And as a result, nothing has moved in like the last seven, eight years. So it's stuck, whereas in eVTOL, which is regulated by the same agency. So the FAA is part of the US Department of Transportation. It's all the same regulator. They've made a lot of progress simply because there's no one standing in the way, right?

• 10:28Speaker 02

  Now they've had to come up with like, okay, what does the flying car look like? What are the safety requirements? How do we certify it? And there's still a whole world of hurt coming that the flying car companies aren't even aware of yet in terms of and that's what that's what the novel is about, local zoning and permitting, building these vertiports. You know, where do you take off? Where do you land? You know, there's going to be a million fights around that. But typically speaking, a startup falls into one of those two categories. And depending on which category it's in, we figure out how to proceed politically from there.

• 10:58Anthony Pompliano?

  Now, when we look at something like the flying cars, or actually, let's talk about the autonomous driving. On that front, we now have insurance companies coming out. So these are people who are betting money in the market to be accurate in their underwriting. They are saying, I think the latest report is that a self-driving car is four times safer than a human driver.

• 11:18Speaker 02

  Yeah.

• 11:19Anthony Pompliano?

  Whether it is two times, four times, 10 times, they are saying it's safer. They're betting money. We have no reason not to believe them. How is it possible that their regulators can then sit there and say, hey, we can't let you do this, blah, blah, blah, whatever. Like, it almost feels like it's data and safety versus something else. Is that how you see it?

• 11:37Speaker 02

  Yeah, it's data and safety versus politics, right? So you've got two things. I mean, you're absolutely right. If there's, I think, something like 26,000 traffic fatalities in the US every single year. If we had full-on level five, everyone's car was autonomous, it would be zero or close to that, right? Maybe something weird would happen, but basically zero. The reason why we're not at that is for two reasons. One is you have some entrenched interest, whether it's sometimes the original car manufacturers are called the OEMs, the original equipment manufacturers, or the big trucking unions, or anyone whose business model would be disrupted by this, and they haven't innovated, and so they can't compete. So the only way they can stay in business is to use

• 12:22Speaker 02

  political contributions and lobbying and all kinds of forms of soft corruption to stop innovation. The other problem is regulators are appointed by politicians, and politicians, and just for context for the audience, so I spent the first 15 years of my career before I got into tech, working in government. I was Mike Bloomberg's campaign manager, ran for mayor of New York. I worked for him at City Hall. I was the deputy governor of Illinois for four years, ran the state's budget, operations, legislation, policy, communications. I was Chuck Schumer's communications director in the US Senate for two years. So I've seen this from every angle, state, federal, local, legislative branch, executive branch, drunk campaigns, all of that. And the sad thing is,

• 13:04Speaker 02

  what I learned is 99% of politicians are desperately self-loathing, insecure people that can't live without the validation of holding office. It fills a hole in their psyche that nothing else can fill, and so they will never do Two things. They will never take any risk that could cause them to lose their next election. I mean, think about, and I don't even know your view on guns, right? But like, clearly, the fact that we have school shootings and Walmart shootings and church shootings, like, it's hard to argue that we shouldn't try to do something about this. And the reason that we don't is because if you are, and keep in mind, I'm an independent at this point, and I hate both parties, but I'll pick on the Republicans in this example. You're a Republican congressman from Florida, turnout in your primaries 12%.

• 13:47Speaker 02

  Half that 12% are NRA members. If you were to say, we ought to consider some sort of assault weapon regulation, you'd lose your election immediately, right? So they're never, ever going to risk that to do what's right. And the other thing is, they're there for the attention, they're there for the validation. And so, you don't get good press by saying, here's the data and here's the stats, and yeah, there's going to be some bumps in the road, but over time, we have to allow this to play out so that we have autonomous vehicles and make everyone a lot safer. It's, you get attention by haranguing against the evils of tech and against capitalism, especially if you're on the far left. And, you know, in the press, because they're so focused on every AV,

• 14:32Speaker 02

  you know, 100 people can die, literally, in the course of a couple of hours in car accidents. No one pays attention at all. Couple of AVs bump into each other across the yellow line or whatever it is, or even what happened in San Francisco where they dragged a pedestrian, and that was legitimately bad. And it's international news. And so, the politician is like a moth to a flame, right? They're always going to take whatever position is politically safe and gets them attention. And so, ultimately, that's what the regulators are constricted by and dealing with. And so, your real question at the end of the day, pomp is... If common sense dictates it would be much safer and regulators' jobs are supposed to make us safer, why wouldn't they do this?

• 15:16Speaker 02

  And it's because safety is not their underlying goal. Their underlying goal, and especially from the politicians, is political preservation and validation and attention.

• 15:25Anthony Pompliano?

  Now, I'm gonna go from one side that has a monopoly on violence and rules, uh, being the politicians in government, to, uh, especially taxi industry, construction, things like that. There is a whole nother group. Most people will, I think, um, naively just say the mafia, but it really is a whole bunch of different groups of people who kind of have their hands in. They have a financial incentive to see things stay the way that they stay. Uh, how do you see that playing out? Both in, you know, a city like New York City, but also just in any city across America?

• 15:55Speaker 02

  Let me just give you two New York City examples, because I'm, I'm, I'm sitting here right, right now. And then we can, but, but these apply everywhere. Um, so the illegal weed shops, right? So New York State has legalized recreational cannabis. Great. Um, we have 27 licensed dispensaries and as many as 5,000 unlicensed dispensaries, which is fucking crazy, right? That you have stores openly selling drugs to children. I got a 17-year-old and a 14-year-old. I live in Manhattan, um, and I know that either of them, anytime they want, could walk into a store and buy weed. Um, and we do nothing about it. Why?

• 16:34Speaker 02

  Because like you said, uh, I don't, whoever owns those illegal weed shops, they've got some juice somehow. Um, it seems to me that likely it's not 5,000 separate small business owners. It's probably a handful of guys, which is called organized crime. And whether they've got protection in the police department or city hall, um, or something else, they're getting away with this thing, which is fucking crazy. Because if New York City, for anyone who listens to this, feels kind of out of control and unsafe. When you literally allow drugs that are unlicensed, and by the way, therefore, uninspected, right? So whether it's fentanyl could be laced with, or just lead, or anything else,

• 17:16Speaker 02

  really unhealthy. When you just turn a blind eye to that completely, then, you know, you're not gonna, uh, you're sending a message to everyone, like, go for it. Now, we have an epidemic in shoplifting, in fentanyl poisoning, um, you know, all homelessness, everything else, and the city feels like a mess. Another one's scaffolding. Um, so, we have a law in New York City called Local Law 11, and it requires that every couple of years, maybe every seven years, a building over four or five stories has to go undergo an inspection of the facade, which kind of makes sense. It happened because sometime in the 60s or 70s, a brick killed somebody. Fine, we get it. However, um, there's a few problems. Problem one is, as anyone who has spent any time in Manhattan knows, scaffolding is

• 18:01Speaker 02

  everywhere, right? It goes up, and there's no enforcement of any kind, and it never comes down. In fact, often by the time they finish, it's time to do it again, so don't even bother taking it down. So the entire city feels covered in scaffolding, and I've talked to the DAs of both Brooklyn and Manhattan about this, and they would both tell you, it increases crime, right? When you have these dark spaces, it leads to more assault, more rape, it gives junkies places to shoot up, um, it makes the city less safe. And the crazy thing about this is, one, there's a technological solution that would require virtually no scaffolding called drones, right? You don't need guys on these, like, you know, bell platforms that kind of with, with ropes and pulleys to look at it. You could

• 18:43Speaker 02

  have a drone just fly through the building pretty quickly, by the way, find out exactly what's wrong with far more accuracy than a human being's going to, and then you go fix that one thing, right? Um, so you have a technology solution, and what's even crazier is- There's not even like a strong union or particularly politically powerful interest behind Local Law 11. It's just kind of always been this way and no one's ever done anything about it. Um, and so you have the combination of corruption, like you said, you have incentives for politicians that are not aligned with the incentives for the actual public. And then you have bureaucracy and inaction and indifference and you put all that together.

• 19:24Speaker 02

  And unless you have a great mayor in a city, so look, when Mike Bloomberg was mayor of New York, a lot of this shit didn't happen because Mike was really on top of it, right? And if, if Mike were mayor right now, there wouldn't be illegal weed shops because he would have had the NYPD padlock, every single one of them and say, anyone who's caught in any of these facilities is going to Rikers. Now, is it possible that he'd get sued or people would protest about it or whatever else? Sure. And you know what he would say? Go fuck yourself. Um, and that's the kind of leadership that you need. We don't have that with Eric Adams and most cities around the country don't have strong leadership and as a result, they feel out of control.

• 20:00Anthony Pompliano?

  Now, when we look at either the weed shops or the scaffolding, are they like, uh, paying, I don't know, business taxes or like, is the city somehow generating revenue or something?

• 20:09Speaker 02

  So, so definitely the weed shops aren't paying any taxes, right? So, I mean, the crime is the people who actually have the licenses to sell cannabis went through a whole licensing process, background checks, they hired lawyers, they hired accountants. And they were supposed to be people who, um, were the victims of overly harsh cannabis laws in the first place. So people gone to jail for a long time for, for cannabis related crime or veterans, whatever it is. They're totally screwed over because the illegal weed shop pays no taxes, no licensing fees, doesn't have any lawyers, doesn't have any accountants. Um, doesn't have to pay to have regulator inspected products. So they can sell at a much cheaper discount. Um, than the regulated shops can. And so the regulated shops can't stay in business.

• 20:51Speaker 02

  Um, and so, no, it is actually not only not contributing, it's sucking away the tax revenue that we should have, right? If you hit the scaffolding, I, I assume the scaffolding companies pay their taxes, but I don't really know. And it wouldn't shock me if the answer is no. But here's what's happening is you have this. Feeling of lawlessness in New York City and we have a shoplifting epidemic. Uh, I think something like 95% of stores have said that they've been shoplifted from. If you want to buy like a tube of toothpaste at CBS in New York, it's CBS New York City. You gotta go press a button, wait for someone to come over, unlock a plastic case and hand you your like Crest or Colgate or whatever it is. So guess what you do instead? You order on Amazon, right? Cause you don't have 10 minutes to sit there and wait.

• 21:33Speaker 02

  And then what happens? The stores close, people lose their jobs, more empty storefronts, more vacancies, more crime. Um, and so, you know, yeah, this is all a reoccurring cycle and technology often can be the solution to a lot of these problems. But I think we're oftentimes founders don't realize, and you know, I, I see this all the time, my own funds. Is, you know, they're good at thinking about the engineering problem at hand. They're sort of good at thinking about the marketing challenge at hand, but because they've been so removed from politics and government and regulation. The way things really work doesn't even occur to them. And how much they're going to have to deal with that oftentimes is a total surprise. And so, look, it's great for me because I have the one fund that then solves the problem. So like, gives us a ton of deal flow and we don't, we don't lose many deals.

• 22:18Speaker 02

  But overall it would be a lot better society if we had regulators and politicians that actually acted in the best interest of the people instead of themselves.

• 22:25Anthony Pompliano?

  So what's interesting to me is, uh, I'm fascinated by, um, the drain on city finances where something like the congestion tax in New York City. Uh, all of a sudden is going to generate, you know, billions of dollars of revenue. And it looks like they're going to have to come up with many, many more creative ways to tax or kind of, uh, drive revenue. And so whenever I see something like that, it would suggest that these cities, when a technology company is coming into them. Now all of a sudden you're not just dealing with somebody who is looking at it from a regulation standpoint. They also may be looking at it from a, hey, how could we tax these people? How could we generate revenue from these people in order to solve some other problem that has nothing to do with the technology or the problem they're trying to solve?

• 23:04Speaker 02

  Totally. And there's, they're, they're thinking way too small, right? So take San Francisco, it has become like a dumpster fire, right? I think pretty much everybody would agree with that, including most people in San Francisco. Um, the, it is a kind of one industry town, which is tech, but a lot of tech has fled to Miami and Texas and other places with lower taxes and, and less regulation and better weather and everything else. And it seemed to me that the one hope for revival that San Francisco had was AI. And when they legalized self-driving taxis, like, oh, that's really smart. They recognize that if they can give regulatory advantages to AI companies in different forms, which could be generative or AV or whatever it is, they can keep those businesses in San Francisco.

• 23:47Speaker 02

  And if the AI industry grows up in San Francisco, that can produce a huge economic recovery, right? And then they went ahead after one problem and banned the cruise, the autonomous taxis. So, you know, they're only thinking about it from the perspective of solving today's political problem. And they would gladly sort of overtax someone right now and destroy the long-term value of that industry if it meant that they don't have to deliver a spending cut to some politically powerful constituency who support they rely on in the next election.

• 24:20Anthony Pompliano?

  Yeah, it, it, um, it really is, I, I, I think, uh, a founder is so under, uh, prepared to go into these environments. How do you identify what success looks like, right? In, in the book, obviously with the flying cars and stuff, like, like it's very clear kind of what you're optimizing towards. But you've done everything from Lemonade to Uber and, and everything in between. How do you start to try to understand like, okay, what exactly is success? And like, are we willing to actually compromise from, we get all of everything we want, like, how does that work?

• 24:50Speaker 02

  Yeah, so, so ultimately, a- as we look at investments, my fond touch venture partners, invest in seed and series A companies. And we're a lot like every early-stage investor. We're looking at the TAM and the founder and the underlying concept. But we ask two questions that I think are unique to us. First is, is there a gating regulatory issue or opportunity that if it were solved can really drive growth and valuation? And if so, can we solve it? Like you said, we invest in FanDuel, ran a campaign to legalize fantasy sports betting, invested in Row, legalized prescription via tax, Lemonade got their insurance licenses and so on. So part of it is the analysis on the front end, where we have to believe not only is there a potentially a regulatory issue or opportunity here, but can we then convert it, right? Because sometimes the answer is like, yeah, this company would be highly regulated.

• 25:35Speaker 02

  And if it could be legalized, it could be. Great business and our opinion is it can't be right like the political forces that they're up against. Are too powerful for a seed or series A company on their own. To be right, which is partly why Uber is a remarkable story because who would have thought that a seed and series A company. Could have taken on the entire taxi industry and taken it down. Um, and that's why Travis doesn't get nearly the amount of recognition in my view that he deserves. Um, because he accomplished something truly remarkable, um, and people don't really seem to to get that. Um, but most of the time, you know. You have to say. Is there either other people with aligned political interests that we can team up with to help us win this fight? Or are people taking on?

• 26:17Speaker 02

  Paper tigers, right? So one thing about taxi where it turned out was they were. They had tons of lobbyists, they gave out tons of campaign contributions, but they had a product that everybody hated. Right? Everyone had shitty experiences in taxis all the time. And as soon as they saw a much better, you know, more option in Uber, they were willing to fight for that, right? And rallying our customers is how we won, um, in every single jurisdiction, uh, for Uber. So it's really figuring out. The relative political strengths and weaknesses. Of what we could muster on our side versus what the entrenched sisters on the other side are going to have. And sometimes the analysis will be like. In one state, you're like, you know, I can't win this fight because this union.

• 26:58Speaker 02

  In this state is super connected to the governor and if they tell the governor to kill the bill, he's going to kill the bill. And then the same union, but in another state, the leader there is weak. Or endorse the wrong person in the last campaign. And it's not going to be a problem, right? So we have to do this multi jurisdictional analysis of. All 50 states or 100 cities or whatever it is. And then based on all of that data, Jordan, my partner and I just have to sort of make a judgment call of like. Okay, on the totality of all of this. We believe we can solve the regulatory problem and it is worth us, you know, risking a couple of million dollars of our LP's capital to try to do so.

• 27:37Anthony Pompliano?

  On Amazon, I always like to look at the description of the book because it tells a lot about kind of how both the author, the publisher, et cetera, all is trying to position the book. And there was a phrase that caught my eye. This is a cautionary tale. Who is the cautionary tale for? Is it for the governments? Is it for the tech entrepreneurs? Is it for somebody else?

• 27:57Speaker 02

  It's a great, probably for everybody, but really for the tech entrepreneurs, right? Because people in politics understand how it works, right? Like when I wrote The Fixer, I had two groups of readers. I had people in tech, I had people in politics. No one in politics called me up afterwards and said, I was so surprised, right? They might say, I enjoyed the book, you got it right. But no one was surprised. People in tech were like, holy shit. That's what you have to do to legalize a product. And so, yeah, ultimately, I think founders and VCs need to understand that the regular story stuff can be just as fatal as hiring the wrong engineers or not raising enough money or having the wrong, you know, marketing plan for customers

• 28:42Speaker 02

  or anything else. And you've got to be able to both anticipate that on the front end and navigate it and devote sufficient resources to it, right? So, you know, there are times where you get to a point where you need a million dollars to pass your bill. And it's a tough call, right? Because if you're a series eight company, a million dollars is a big chunk of your funding. But at the same time, if you literally can't exist without this bill, then what's the difference, right? It's a binary choice. And so, yeah, I mean, I think really, you know, a lot of what I do, whether it's the books I've written or the podcasts that I host or the teaching that I do or speaking or whatever else, is really designed to try to help people in tech understand here's how and why politicians make decisions. Because if you understand what's motivating them,

• 29:28Speaker 02

  then you could at least figure out a strategy to do something about it.

• 29:32Anthony Pompliano?

  When we see maybe the lessons from Uber, lessons from Lemonade, et cetera. Do the governments change their tactics if they realize that something worked from the private market? Like in terms of, you know, Uber, one of the stories I always remember is like, basically one day you guys wiped the app. And was like, this is what it would be like if this legislation passes, or you know, whatever the story was. But like, do politicians like, oh, cool. Like, we saw that one time. The next company that walks through the door and tries that, now we've got this new tactic that's going to be able to mitigate that strategy?

• 30:01Speaker 02

  Yeah, sometimes. So I think Uber and Bird are actually a really good set of comparison here, right? So when, when we did Uber, you know, this, we started these campaigns back in, in 2011. And the, the bad news was no one took us seriously, but the good news is no one saw us coming. Right? Like, people just laughed at us and no one really paid attention to us. And then all of a sudden, we were mobilizing tens of thousands of customers and more important voters in those districts to say, no, leave this thing alone. I want it. And that changed the underlying politics and we won. So we took them by surprise a little bit, which was great. So when Bird came along five, six years later, and we were launching Bird in cities all over the country. And this is true for Lime and the other scooters too.

• 30:45Speaker 02

  It was both better and worse, right? It was better because we were at the table, right? They understood what would happen. And, you know, it's easy for me to basically say to a transportation commissioner, you saw what I did to the last commissioner and their boss politically. You want me to do that to your boss and then you lose your job? Or do you want to have a meeting and figure this thing out? The people took the meeting, right? At the same time, we lost Yalman in Surprise and entrenched interests. And we were lucky in the case that there's no like big scooters. We didn't have to sort of take anybody out in this case. But, you know, 10 years ago, big insurance, hotel, casino, whatever it is, they were really slow to recognize the threat and that gave us room to run and, and time to mobilize.

• 31:29Speaker 02

  And now that they've seen over and over again, how startups can kick their ass politically, they have become a lot more aware, which actually makes the fight harder.

• 31:39Anthony Pompliano?

  Yeah, it's interesting that like you would think the politicians in the government are so powerful, but actually the nimbleness, the creativity, the tech solutions of the tech startup could could give an advantage. And then in some weird way, the CEO of the company is still going to be here five years from now. The politician is not necessarily guaranteed that. And so they've really got to make sure that they get reelected.

• 32:01Speaker 02

  Yeah. So if you think about it, and it actually at the end of the novel, if you saw there's a list of the 10 rules of demystified politics. And I wrote these a couple of years ago, and I just use them all the time. And the first rule is every policy output is the result of a political input. Every politician makes every decision solely based on reelection and nothing else. Other exceptions, sure, Mike Bloomberg was certainly an exception. And there's dozens of them. But overall, the exceptions of anything kind of prove the rule. And so let's just use Uber again as an example. It's an easy one. You're a city council member in Tulsa, and you go to any city you want here. And the taxi guys give you three grand per campaign cycle and contributions. All things

• 32:43Speaker 02

  being equal, you want the three grand for your next campaign. So you did what they want. Now, I just mobilized 4,000 people from your district to email, tweet, text, call, and say, leave this thing alone. I don't want to lose it. Now, my 4,000 people may not necessarily be regular voters, but you don't want to wake these people up and piss them off, right? And so the input changed. So the input went from, I'll take the three grand and do what taxi wants to, I'm not going to piss off these 4,000 people. I'll do what Uber wants, right? And it's all about changing those underlying inputs. So I think for any startup, when you're thinking about this, especially if you're trying to displace and entrench the interest, and you're disrupting something, you've got to figure out, can I change the inputs? And look, there are other startups that I've

• 33:26Speaker 02

  worked with that are great companies. But the customers just aren't passionate about the product in the way that they were for Uber, or FanDuel, or Ease, or Bird, where we were able to mobilize lots and lots of people and be successful. Sometimes it's like a platform or a company that's like a really good company. It's a really good service, but like, no one cares quite enough to like, take time out of their day to do anything about it, even through the app. And in which case, you know, that strategy doesn't work. So you've kind of got to think about like, do I have the kind of product that people will get passionate about and fight for? And if you don't, and you're disrupting someone in entrenched interest, and they're very politically powerful, you're going to have a problem.

• 34:09Anthony Pompliano?

  What is your single biggest lesson over the process of doing this for so many years? That when you went to write the book, you were like, I cannot put this in the book.

• 34:21Speaker 02

  Um, that's a great question. So, so there's a subplot in the book or a kind of central plot, actually about um, a corruption, political corruption investigation into the mayor of New York City, a guy named Joe Navarro, um, and, and there are FBI agents who are characters in the book. And so I, do you remember getting Rod Blagojevich?

• 34:42Anthony Pompliano?

  No.

• 34:42Speaker 02

  So he was the governor of Illinois.

• 34:44Anthony Pompliano?

  Yes, yes.

• 34:45Speaker 02

  Yeah, who went to got a 14 year jail sentence. He had the poofy hair and he tried to sell Obama's senate seat after Obama became president. So I was his deputy governor, right? So I spent four years running the state of Illinois for this lunatic. And um, when he got arrested, you know, I had the FBI show up at my doorstep and say, we need to talk to you. And I ended up having, and they charged him with um, do you know who Rahm and Ari Emanuel are?

• 35:11Anthony Pompliano?

  Yes.

• 35:11Speaker 02

  Okay. So Rahm at the time was the mayor of Chicago, Ari was and still is the CEO or chairman, whatever it is of Endeavor, which is the biggest kind of talent agency in Hollywood. And Rod had apparently promised Rahm two million bucks for athletic facility in Rahm's district. Um, and then it didn't happen. And then one day I get a call from Rahm. And by the way, the, if you remember the, the character Ari from Entourage.

• 35:37Anthony Pompliano?

  Yes.

• 35:37Speaker 02

  He's based on Ari and Rahm in real life. And a call with Rahm in real life was like what the script would be in Entourage. You know, just get hung up on three times. You're told go fuck yourself six times, whatever it is. But eventually you kind of get the gist of what he needs. And then I'm on the phone with Rod that night and I say, hey, Rod, Rahm called me and he's really upset about this thing. I don't really know what it is, but you know, I can just make sure the, the money gets released. He said, no, no, no. And I said, why not? He said, Ari owes me a fundraiser. What do you mean? He said, Ari's supposed to have a fundraiser for me for my next campaign. I'm not giving Rahm the money until I get what I want from Ari. And I said, Rod, we got a problem here because one's political, one's governmental. You can choose or not, choose not to support this discretionary grant, but your basis for the decision can't be on whether or not they give you money. Right? That's corruption.

• 36:23Speaker 02

  He said to me, you tell Rom that no, no grant till the fundraiser. Luckily, I was smart enough to instead call our general counsel and say, hey, uh, Rob is doing this. It's highly illegal, put a stop to it. Um, and luckily the grant was given, the fundraiser never happened. Uh, but I had to testify to that in a grand jury, in a trial, and then they had a fucking hung jury. And then another trial, so three different times. I had to go back to Chicago, um, with tons of media around and everything else. And so a, a lot of what's in the book is shaped by these crazy experiences that I've had, um, in real life. And look, maybe I've had a higher share of crazier experiences than, than most people in politics.

• 37:07Speaker 02

  But I think that generally speaking, the stuff that you see in this book is reflective of real life a lot more than you want to think. And just again, and we're talking about New York City. Guess who's, uh, guess which mayor of New York City is under federal investigation right now? Our current one, Eric Adams. So literally the same week that the book came out, the FBI met Adams on the street, seized his phones, uh, and launched a major criminal investigation into him. So life and art kind of imitate each other quite a bit.

• 37:35Anthony Pompliano?

  There is a politician who I don't want to say their name, but one of the staffers told me, uh, every single day at like two or three o'clock, there's a press conference. And I was like, like it's scheduled weeks in advance. And they were like, yeah. And I was like, well, what do you talk about? They're like, we'll, we'll find something.

• 37:53Speaker 02

  Right.

• 37:54Anthony Pompliano?

  Like, like basically like we're gonna have a press conference every day and like we'll figure out something to talk about.

• 37:58Speaker 02

  Totally. So when I worked for Chuck Schumer, so Chuck is the Senate Majority Leader. So he is the most powerful person in the U.S. Senate, one of the three most powerful people in the U.S. government. Chuck is the most aggressive kind of media conscious member of Congress that I've ever met. And every single Sunday, we would have a press conference. And the reason we had it on Sunday is there was very little competition because most people are with their families or watching football, going to church or whatever it is. Um, happens to be really highly rated local newscast that night because people are kind of at home and they're not very anxious. We're doing on a Sunday night. And so every Sunday we had a press conference and my job was to make up something that would get attention every single Sunday with absolutely no relevance at all to real life, right? All that mattered.

• 38:41Speaker 02

  And one of the things that we would do, if we'd have anything better, is we would write a letter to some company or somebody protesting like, writing a letter to Kellogg protesting the high price of breakfast cereal, right? And Because the internet was around then, but it was nascent. So things weren't moving at the same speed. The company people weren't working on Sunday. And, you know, kind of, we had a one sided story, right? Because it was hard for them to respond. But I started noticing that when there were responses, a lot of the responses were, we never got Senator Schumer's letter. And what I realized was, it was so besides the point that after the cameras left, it didn't even occur to me to actually send out the letter to the company that we were publicly attacking. And I had to put

• 39:23Speaker 02

  a post a note on my computer screen that said, remember to send the letter. So yes, that's the way your friend described it is exactly right.

• 39:32Anthony Pompliano?

  When I see things like, um, who is it? Elizabeth Warren recently went after Big Sandwich? I don't know if you saw this. Yeah, she, uh, somebody is trying to buy Subway, I think it is. And they also own like a deli and another, I don't know, Jimmy John's or something. And she's like, you know, we can't let the monopolies get like the sandwiches. I almost look at it. I'm like, is this tweet being written specifically to elicit trolls and to go viral and to like, create even more news?

• 40:00Speaker 02

  Yeah. Well, it's funny. I was thinking that you could do a great piece of performance art of running someone for office, who is just sort of your run of the mill crazy left winger or right winger, depending on wherever you are. And they start off, it's just sort of the usual now. And then they keep slowly getting crazier and crazier. So like, for example, I saw an article the other day, that there was a strike by the teachers' union in Portland, Oregon, right? So you can only imagine how fucking left wing that all is, right? Um, and I was like, imagine if like this politician or this candidate, you know, was on the other picket line, marching with the teachers, and then kept slowly advancing it to the point where by the end they're arguing, it is unreasonable to ask teachers to come to work at all, or to teach at all. We should just

• 40:44Speaker 02

  be paying them for nothing. Um, and my view is, A, they could keep getting attention and they'd keep getting supporters, because people will go along with it, right? And sort of the performance art would be, kind of, how long can you keep the joke going for before someone finally figures out like, oh, this is a parody, it's not real. And the game would be, can you make it to election day without anybody noticing?

• 41:06Anthony Pompliano?

  You think it could happen?

• 41:08Speaker 02

  Yes, I think it definitely could happen. I think you need to do it for sort of a lower level office, but maybe not. I mean, think about George Santos, right? This guy is a member of the United States Congress. He lied about every single thing, his sexuality, his religion, his ethnicity, where he went to school, where he worked. Nobody found out. He got elected. I mean, in New York, by the way, so the New York Times never bothered to check, New York Post, Daily News, Democratic candidate didn't check, his primary opponents, nobody. And so, you know, the whole premise I just laid out is based on cluelessness. And I was thinking, well, it's going to be some small town somewhere, but it just fucking happened, you know, here in Long Island and Queens. So, yeah, maybe you could do it anywhere.

• 41:51Anthony Pompliano?

  It, uh, it blows my mind, um, you know, how, how kind of crazy the politics stuff is. Uh, obvious in insight, a novel, or I'm sorry, obvious in hindsight, uh, a novel by Bradley Tusk. Um, what's kind of like the one sentence pitch for people, why they should go read something, uh, that is one fiction, which a lot of people I think kind of shy away from at times, uh, but two, still has a very serious, um, I think, kind of lessons for business people.

• 42:15Speaker 02

  Yeah, it is a fun, funny, easy way to understand how and why politicians think and make the decisions they make. So that if you are a founder, a startup, a VC, whatever it is, as much as you hate it, you need to know it. Um, and this is going to be the most fun way you can learn it.

• 42:32Anthony Pompliano?

  That, uh, that makes sense to me. Bradley, thank you so much for, uh, for doing this. Uh, the book is available, Amazon, everywhere else that, uh, the books are sold. So, uh, hopefully people go and they grab it and, uh, we'll do this again in the future.

• 42:43Speaker 02

  Thanks, Bob.