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A
So after running the successful mayoral campaign for Michael Bloomberg in New York City, you gained prominence in the startup ecosystem by successfully lobbying for Uber. Tell me about how you went about getting cities to adopt Uber.
B
When you think of Uber today, you just think of this giant corporation, right? You know, a couple hundred billion dollar market cap, you know, big thing. But back then we were a tiny company, series A. I met Travis in early 2011, and here was this brilliant guy who was incredibly aggressive and relentless with a really good idea. And when you saw the product, a really good product, but still very small. And the taxi industry was very big, very politically powerful, lots of lobbyists, lots of campaign donations, lots of relationships with politicians. And so it was a pretty heavy lift. And we started going into cities. We kind of famously didn't ask for permission because our view is if we did, they would just say no, and then that would be that. So we were better off just going in anyway. And then invariably they would tell us to leave. We would get a cease and desist letter, we'd get another one. And the only way that we could counter taxi's power, because we didn't have at the time the kind of money and resources to match them politically, was to do it with our customers, right? And the first time it happened, in 2012 in Washington, D.C. there was legislation that effectively would have put Uber out of business. And we sent a Note to all 50,000 of our, to all of our customers in D.C. and within a week, 50,000 of them reached out to their city council members to say, hey, I like this Uber thing, don't take it away from us. And it worked so well that not only did the bad bill die, we put it on our own bill, which passed nine to nothing, including the sponsor of the bill that would try to put us out of business. And what that said to us was, at the end of the day, politicians are just going to, which I already know for my time in politics, but they're going to do whatever they think helps them win the next election. And all things being equal, if they can take campaign contributions from taxi and do their bidding, they'll do that, right? But if 5,000 people from their district all of a sudden say, hey, don't mess with this thing, I want this, they're going to listen because they're not going to want to piss off all those people and take that much risk. And so that became the basis for the strategy. And then we ended up effectively using a version of it in pretty much every single city in the US and it worked. Amazingly, everywhere, some were bigger fights than others. New York kind of came back around a second time and we had to fight it again. But the strategy fundamentally worked really well.
A
I mean, the secret to how you go about aligning with politicians, and this.
B
Sounds a little cynical, I know, but keep in mind, just to give context for the listeners, I've worked in city government, state government, federal government, the executive branch, legislative branch. So I've really seen this movie from every conceivable angle. And the main thing that I took away from it is every policy output is the result of a political input. Every politician makes every decision solely based on winning the next election and nothing else. And there are exceptions. Mike Bloomberg in my career was certainly an exception. Everyone listening to this has a couple of names popping into their head right now, sure. But by and large that's the rule, which really means you have to be able to show a politician that by doing what you want, they will win their next election. And if they don't do what you want, it could cost them an exile action. If you can convince them of one of those two things, then they'll work with you. And if they don't think that you can help them or hurt them, you just become irrelevant, in which case they're not going to really waste any time on you. So you have to show that your underlying policy goal is aligned with their.
A
Political same, I guess, with a bank. If they make money, they're going to do it. If they lose money, they're not going to do it.
B
Politicians, at the end of the day, are human beings, right? And human beings want to advance. They want to succeed, they want job security, they don't want to get fired. The only real difference is in the world of tech and finance and venture like we live in, it's around questions of revenue or burn or fundraising or EBITDA or growth. And there it's questions of poll numbers and political fundraising and media hits and social media likes and things like that. And so fundamentally, the people are still people. They just speak different languages and have different sets of incentives and you just have to realign what you need to make sense to them.
A
Michael Bloomberg I think that's a great case of somebody that's not, not purely driven by elections. How, how do you go about ascertaining whether a politician is purely driven by elections? Or maybe they might have some first principles that drive their making.
B
Good question, because obviously, no, there's no sign on the door. And by the way, they all like to think that they're the latter they all want to think they're Mike Bloomberg, when in reality, very, very few of them actually are. And so there's a few ways to tell. One is sometimes there's an issue that is deeply personal to a particular legislator or politician for some reason. And if you can link your thing. And sometimes you can't, sometimes you can't, but if you can link your thing back to that issue so you can show them, hey, here's this problem that you're worried about. Maybe something that affected their family member to, like, not that long ago, I was speaking to a really prominent state legislator, and I didn't even realize, but his daughter had a bunch of online issues with cyberbullying and everything else. And when I kind of made the analogy to what I was talking about, to social media regulation, that clicked for him, right? And then all of a sudden, he's like, oh, okay, I have to. I live this. This is terrible. Let's do something. And so sometimes there might be an issue they really care about. Sometimes you could just get a sense that in the past, they've said or done things that have broken with their party or been unpopular. So, like Mike Bloomberg, in some ways, the most visible example that, to me was, Mike is a New Yorker. He's Jewish, basically. One was running from air during 9 11. And then there was an effort to build a mosque right by ground zero in New York, and it was wildly controversial because the idea was, how could you possibly build a mosque at the site where 3,000 people died from the hands of Islamic fundamentalists? And Mike's view was, you know what? They have an absolute First Amendment right to be there. And it doesn't matter what the symbolism or anything else, that's their right. And Mike stood up for them and allowed it to happen. And it was really unpopular, to be honest. But I really, deeply admire that because it was the right thing to do. Or even the smoking ban. Now, I think everyone thinks it's fantastic. And literally hundreds and hundreds of cities all over the world have followed New York's lead on that. But I remember because I was at City hall when we passed this. It was really unpopular, right? Like, you go marching parades, and people are giving him the finger. And. And the legislature didn't want to do it. City council. And Mike just kind of used all of his weight and pushed it through. And. But collectively, if you look at the result of that and then all the other work he's done around tobacco cessation, it saved millions of lives. And so there are occasionally the Mike Bloomberg's of the world. And sometimes you can tell because either they've shown independence before, they're not total party hacks. They've expressed, you know, a personal story about an issue they truly care about, Things like that.
A
Said another way, if it hurts them in the polling, and they're not idiots, essentially, they're working from something above and beyond getting votes.
B
Exactly. But generally speaking, I think the challenge is there are so many different demands on their time, on their political capital and everything else that they're looking at everything in some ways with the same kind of ROI that investors do. But it's just, again, rather than saying, what's the rate of return that I can generate here? It's what's the political rate of return? Let me give you an example. So one of the things we got at my foundation is we fund and run campaigns to pass universal school meals in different states. So basically, it means that every kid in the state gets free breakfast and lunch. There's over about 13 million kids in this country who still don't get enough food at home and really do need it to get it at school. And we've been lucky. We've had some success. We've passed about 29 bills around hunger in total. But sometimes we fail. And when we fail, it's because ultimately we fail the ROI calculation politically. So when you pull school meals, pretty much everyone says, yeah, we should feed kids, shouldn't let them go hungry.
C
Right.
B
You have to be a monster to say that, to not say that. But then when you get into those final days of the budget, and I used to be the deputy governor of Illinois, and so I was the person that ran the budget, and remember this really well, there's a lot more requests for funding than there is funding, and you have to start making choices. And. And even though the notion of school meals is quite popular, there's no actual political ROI for doing it, because the kids can't vote. They're kids, and the parents don't vote, because either they're not citizens or they work hourly jobs and they can get away to vote or whatever it is. But ultimately, you're not going to really pick up a lot of actual votes at the end of the day by doing school meals. And we've had states, even Democratic governors like Josh Shapiro in Pennsylvania or J.B. pritzker in Illinois, who at the end of the day chose not to fund school meals because I think they realized that, yeah, you know, it's nice for kids to eat, but if I could use that $300 million to pay off some union or some other special interests who could then actually help me in the next election. I'm better off doing that. And so, you know, in many ways, when I made the transition from politics to venture, it actually wasn't that hard to do because early stage startups are a lot like political campaigns. And the, what investors are looking for is fundamentally kind of the same as politicians, just again, different metrics, different kind of buzzwords. But, but, you know, once you can kind of translate the languages, it actually is fairly similar.
A
One, I think misconceptions about lobbying is that you literally take a suitcase and you put it into politicians. Yeah, politicians corner.
B
Obviously, now it's all in crypto.
A
Yeah, highly illegal. Now it's in crypto. But in many ways the most effective lobbying is when a politician doesn't feel like they're being lobbied. When they, when they own that.
B
Sure.
A
Feeling.
B
Yeah. You make them the hero of it.
A
Yeah, yeah. And talk to me about the effective lobbying and how do you get your dollar to go further than just, you know, ROI and getting the emotional appeal in politics?
B
Well, two things. So one is when I started my first company, it's a consulting firm called Tuft Strategies and they run, I still own it, I don't work there anymore, but they run, you know, really complicated legislative regulatory campaigns all over the country. And the thesis that I had for the business, and I didn't know if it was right or wrong, but it was enough for me to take a shot. I did this right after Bloomberg got elected, was that the days that you were kind of joking about where a guy knows a guy and he makes a call and everything kind of gets fixed, like those days are gone. And by the way, if you're ever on a call with someone like that, assume that the FBI is listening to. And the way the campaigns are won today is much more multifaceted. So yes, lobbying is still a big component of anything, but so is earned media, paid media, social media, digital media, opposition research, grassroots, grass tops polling. There's all kinds of other factors. And my bet was because I had experience in all these different things, I could bring all these to bear and do it at the same time in multiple jurisdictions for a client or for a company. And that's what would allow us to win and allow the business to grow. And that is what happened. And so the first thing is you kind of have to really look at it and say, okay, there's, let's say I think I just listed about 10 different tactics. It's a menu. And you don't need all 10 in every single campaign in every case. So the question is, what are the things that are going to be most effective with the particular regulator, the particular politician that you're trying to convince? For some people, maybe it is hiring the right lobbyist because it was also their college roommate and they just explain it to them. That's good enough for a lot of people. It might have to be, you know, having 5,000 constituents like we did with Uber, call their office or text them or something like that for some people. So we have to run TV ads attacking them for some people. Like this past year in New York, Governor Hochul did put universal school meals in her budget and we went the other way with it, which is we just started running ads immediately thanking everybody. Like we basically said, we're going to make the assumption that they've already all agreed to it. It's happened and we're just start giving them credit on day one because it would look so bad to get all of this credit for school meals and then not do it. That that was the, you know, get them really feeling good about it, get them emotionally invested and create a template where kind of no matter what happened with the budget, this thing just had to happen, it couldn't lose. And that's how it went. A lot of it is really figuring out in every situation what's most likely to move the needle with the particular people you need. Oftentimes in some ways, I kind of think our job is psychology as much as anything else because it's figuring out what will motivate this individual person, what will incentivize them, what will scare them, and then how do we then deploy different tactics to make that happen.
A
And You've helped Coinbase FanDuel Lemonade RO and you literally wrote the book on startup lobbying called the Fixer.
B
Yep.
A
Walk me through your framework. How does a startup go about influencing politicians?
B
The first thing is really understanding what your situation is. So, you know, because I talk to founders every single day, whether it's the ones in my portfolio or people pitching us, one of the first things I try to establish is either what do they know? Or by the way, equally important for me, do they know what they don't know?
C
Right.
B
So like take Travis Kalanick, who is a very, very brilliant, very, very hard nosed guy. Travis, to his credit, understood that he wasn't a political guy. And one of the reasons that we were able to work really well together and we still do and succeed is he knew what he didn't know.
C
Right.
B
And he had his opinions and we might argue about stuff, but at the end of the day, he let me do my job. And that ultimately works. So one is, if you are a founder, just because you went to Stanford, just because you were in Y Combinator, just because Andreessen invested in you, around whatever it is does not mean you know everything about everything. You might be great at the engineering, you might be great at marketing or product or whatever it is. Odds are you're not automatically great at politics. And some regulator or elected official is not going to just meet with you and look at your resume and say, oh, this person is so impressive, I should do what they want.
C
Right?
B
So first is any founder actually that really, truly believes that going in, I'm going to meet it. No, I will not invest. That will not work with you. But the first thing is you have to understand what you're facing.
C
Right?
B
So what are the current laws on the books around whatever it is you're trying to do? And odds are, if you're a founder of an interesting startup, you're approaching it in a way the law hasn't totally considered it yet, because by definition, regulation lags innovation. Because until the founder comes up with the new disruptive idea, there's no law to pass around it.
C
Right?
B
So the law is probably going to be gray, but how gray is it? Like, this is definitely not allowed and you have to actually go in there and overturn everything, or is it just kind of like, well, we don't really know. You can make a case that's one to what happens to you if you don't listen to them.
C
Right?
B
So like with Uber, they impounded the cars. Annoying. At the end of the world. With Bird, they take the scooters. Great, take the scooter, who cares?
C
Right?
B
But if it's, you know, an SEC thing, you'd be looking at 10 years in jail. That's a different ballgame, right? So Lemonade or Circle or Coinbase, different approach for us than say, a Bird or an Uber or a mobility company. So what does the current law say? What risks do you take by your actions? Who is against you and how politically powerful are they? Is it a union that's not going to like it? Is it an entrenched business group that's not going to like it? Is it the hotel industry, the casino industry, the taxi industry, whatever it might be? And then how politically powerful are they? How much money do they give to the politicians that matter here? What kind of relationships do they have? What kind of goodwill do they have? Next one would be, who can you get to your side?
C
Right?
B
So it might be your customers, like we've talked about. So in some campaigns, like Uber, like FanDuel, like Bird, like Ease, that really worked. But it may be that you have the kind of product that's maybe a really good business, but it's just not going to inspire your customers to do a lot of outreach on your behalf. So it's like, okay, who else do I have? Maybe there is an advocacy group or policy group, or maybe we're able to, you know, deliver things a lot faster. And so businesses in that jurisdiction are happy about it, and they'll fight for you, whoever it is. But you got to find your allies. You also have to then be able to figure out, like, what's your narrative and what's your message? Because at the end of the day, if you just go in there and say, you should legalize this thing because it's good for me, like, nobody cares about that, right? If anything, they'll sort of not like you for that. You have to make the case credibly that public policy, that society itself is advanced because of the work that you are trying to do. And so if you let me do X, then we can give more people better transportation options or better food options, or give people better ways to get cheaper homeowner insurance or whatever it might be. How do you make that case? And then who can you make the case through? So what's the media market you're in? What are the mainstream media options? What are the things like podcasts and substackers and influencers and creators? And who can you work with there? And then finally, and, you know, like you said, I wrote a book about this, so if you really like this stuff, you can read the book itself. But budget, right? Which is sometimes, you know, I can look at a case and say, all right, you know, what if we spent 50 grand, we probably have enough to go ahead and get this law changed or get this sort of thing approved. And sometimes this is gonna be a couple of million doll, depending on where you are and what you're facing. What we almost always do is, you know, kind of make a stack ranking of what jurisdictions do we think it would be the easiest or hardest to implement this in based on all the criteria I just laid out. And you usually first start with the ones that we know we can win so we can get some points on the board, so we can establish precedent, so we can show that other people do it, and it works and then work our way up so that as the company both has more success and then more resources, they've raised more money or whatever else us, you know, we can tackle the really hard markets.
A
So there's an old quote from Pericles. You may not take an interest in politics, but politics takes an interest in you. I think a lot of startups are a little bit naive to this. Walk me through when startups should start to lobbying when it's too early. And what's the timeline for company that's.
B
That has a disruptive product really depends on what it is you need.
C
Right.
B
So if you are take Lemonade, which is an insurance company that we invested in, we had to do all of the regulatory work at the very, very beginning because you can't sell insurance without a license. And you know, no one eliminated was going to go to jail for this.
C
Right.
B
So at the end of the day they couldn't actually launch operations of the company until we did the political work first. Fanduel we didn't get involved actually on the political side till the series E because know they launched, it wasn't clearly illegal, it wasn't clearly legal, no one really knew. And for a long time they operated pretty successfully DraftKings too. And then all of a sudden there was a political backlash and then State Attorney General, 3rd Edition cease and desist orders and then we had to go in and change the laws, clarify the laws, kind of work through all of this. So I think the first thing is you need to know at least what it is you need from government and when in your product life cycle is that important. It might be something you need on day one, it might be just something that's going to come up later on. And then two, you know, if it's day one, then obviously that has to be one of the initial things that you invest resources into. If it's later on, you got to be aware of it. You have to sort of, at least in your mind, have some budget reserve to deal with it. But also keep in mind it depends a little bit on your own success, which is the faster you grow and the more that you make your VCs happy, that means you're taking market share away from somebody else and that somebody else is probably an entrenched interest that is more political than you, that has more relationships than you. And then they're going to move as fast and as hard as they can to use politics to try to knock you down. And so in some ways if you have success, you have to assume that that's going to bring political challenges with it and you have to be ready for it.
A
Tell me about the crypto lobby and their success in the 2024 election. What changed? Why were they so successful in this last?
B
They were great. So they did a great job, first of all, and I think for two reasons. One is money, right? And it's an industry that ultimately A, already has a lot of money, B, you have people in it who you know are holding tokens in different ways worth a lot of money. So they have the ability to contribute. And see, you know, there's no capex in crypto, right? So other than mining, I guess. So, like, ultimately, regulation is a really, really, really big determinant in your success or failure. And so it's worth a very meaningful investment. And they raised and deployed hundreds and hundreds of millions of dollars. And not only did they raise and deploy a lot of money, they were really smart, strategic about it. Which was rather than saying like, okay, here's three grand to every single person running for office in America, they said, let's pick a few people and make huge examples of them. So like in Ohio, I think they put $40 million into the Senate race and were successful. And what happens is when you do that, every other politician sees what just happened and they get really nervous. And so your $40 million investment might have 4 billion in value because ultimately you were able to change perception and behavior by lots of the other 99 senators because they saw what just happened and they don't want that to happen to them. And so they were smart, they were strategic. And the other thing that works for crypto is, you know, I mentioned this earlier, there are some industries where the customers are really willing to kind of step up and fight for the product. You know, Uber was one, FanDuel was one, Bird was one. Ease, which is marijuana delivery was one that we did. And crypto is very much one of those, right? And so you have customers that are passionate, they really believe it and care. And keep in mind, most people who trade crypto are doing it because, you know, they're interested in it, they think it's a way to make money. But the true believers in crypto fundamentally are saying, look, I don't really believe in sovereign banks and financial institutions. I don't think that they're looking out for my interests. I think they're looking out for themselves. And I would rather actually throw in my lot with like minded people who I'll never even know their names but believe, like I do, that an autonomous currency is actually a better way of doing things. And so one of the things about crypto is, at least for some of the community, there's a real belief system in there. And when people believe in things and doesn't have to be tattooed, you see this with like say abortion or gay rights or whatever it is, they will fight for it.
C
Right.
B
And I think crypto has that.
A
There's this combination of real politic and very strategic financing with this kind of grassroots crowdfunding aspect to it, which, which accelerated. So let's say that you believe that Elon Musk should go into politics. I personally do not believe that. I'm a huge Elon fan. I think he should stick to business. But if he was to go and launch this America Party, where would be the point of highest leverage for him to come in and have an effect?
B
Yeah. So I've not only thought about this a little bit, but I, you know, I've worked on third party issues before. My friend Andrew Yang created the Forward Party. I give them some advice. Before Mike Bloomberg did end up unsuccessfully running for president as Democrat in 2020, I didn't get to play much of a role in that one. But I had put together a campaign 2016 for him to run as independent. And so I really spent a lot of time looking at all of that. The first question is what do people mean when they say that?
C
Right.
B
Which I'm not even sure that Elon knows what he necessarily means, which is it's one thing to say I am going to back and finance an independent candidate for president, governor, senator, mayor, whatever it might be. And if it's a one off and you have the resources, you can do it. So like the first step is getting on the ballot. And it's hard to get on the ballot if you're an independent because the only people who can sign your petitions are other independents. And that becomes harder to find and whatever else. But it's a noble proposition. If Elon really meant an actual party. What that means is an entity that is competing at every level of government.
C
Right.
B
They're running candidates for city council, for mayor, for county board, for state rep, state senator, governor, Congress, senate president, and have a permanent ballot line which the rules differ state by state, but usually it's based on sort of capturing a certain percentage of votes in each election. That is a many, many, many billions of dollars investment. That is a many years investment. It is potentially doable, but it would require one massive financial resources which he has. Right. But he has to choose to put them into this two. You need to stand for something, right?
A
You need.
B
And what you need to be able to do is something that will recruit a lot of people, right? So what Trump figured out with MAGA was you had this group of people who felt really angry at the status quo and that he was able to mobilize and bring them together under this banner. Bernie Sanders, AOCs are on now. Have sort of figured out the same thing on the far left, right, with the socialists. I actually think, ironically, the best opportunity for this is the middle right. You have all these people now who are not radicals on either side and actually feel totally powerless and disaffected and would love to have a political party that they thought was really believed in, the things they believe in, which really most times is just common sense solutions to problems, right? Like if you take almost every major issue, there's a 70% solution where the vast majority of us can agree on it. So take guns. Most of us would say you shouldn't go into everyone's home and confiscate the guns they have. But it also shouldn't be easy to walk into a store and just walk out with an assault rifle, right? Or immigration. Most of us would say we should have secure borders. You shouldn't be able to just walk across and get in for no reason. But we also shouldn't be like, out rounding up and deporting millions of people who have lived here and work here and are part of the economy either. And you can pretty much on every issue, to me find that. But the problem is that 70% on any given issue tend to not vote in primaries. And the way our system works because of gerrymandering is the only election that really ever matters is the party primaries and party primary turnouts, typically about 10 to 15%. And those are usually the most ideologically extreme voters, whether it's the left or the right. And then they end up dictating everything that happens after that. And so I think there's a huge opening in the middle and Elon could center a platform around that. But the problem is I don't know that he personally has the discipline to stick to it, right? So if you're going to do that on your hand, you can't say things that are endlessly alienating, like all women, right? Or all people of color or immigrants or whatever it is, because now they're your potential party members and you need their support. And so if you are. If he were going to go for it in that way, he would really have to be able to rein Himself in either stop tweeting or really, you know, and it seems like he gets a lot out of whether it's good for him or not. He clearly relies on the attention that he gets from being online and really active. Now, look, he could instead go the other way and go super crazy far right and probably form something, but it's going to be a niche party that sort of is filled with lots of really hateful people that don't want to get anything done.
A
Talk to me about your work in mobile voting. First of all, tell me about that and why are you so passionate about it?
B
Every politician makes every decision solely based on winning the next election. And as we discussed, because gerrymandering means that only the primaries typically matter, and primary turnout is really low, politicians are effectively held hostage by the small groups of people who do participate in their primaries, which are typically either ideologically extreme voters or special interests. And the only way to really change that is to change the fundamental composition of the electorate itself. So instead of getting elected with 12% of the vote in the primary, you're getting elected with 36% of the vote, because by definition, 36% of people is more mainstream than 12% of people.
C
Right?
B
And so if you assume that politicians are always just going to make the politically salient choice at every turn, rather than trying to make them different people, because we're not going to do that.
C
Right?
B
And so I kind of realized all this in the Uber campaigns, because what we saw were all these people who typically did not vote in state senate primaries, they didn't know who their city council member was. But for us, they were through the app telling their elected officials like, hey, leave Uber alone. And I kind of started wondering, like, well, what if they can vote this way? And so I started this thing called the Mobile voting project in 2017. And the first thing that we did was test the hypothesis, which is, if you put voting on people's phones, will they do it? And the answer was, yeah, you make something easier, more people do it.
C
Right?
B
Turnout, for example, in an election in Seattle tripled. So, okay, we established, yes, the hypothesis is right. But the tech that existed at the time to do this was pretty rudimentary. And it worked fine for, you know, 2,000 votes here, 5,000 votes there. But to do it at scale, we didn't have confidence in it. And the problem is, nobody was going to otherwise build the tech that we needed, because a private company doesn't want to spend eight figures and then make the code open source and give it away to their competitors. And the US government wasn't working on it, didn't want to, and so we decided we would do it. And so we've spent the last four years building our own mobile voting technology. We're putting the code up on GitHub now as we keep completing each part of it, it'll be fully posted by the end of the year and it will be completely free for anyone, any government to just go to GitHub, get the code and use it. And then now we're in phase three, which is the really hard part, which is legalizing it so that people can start to vote on their phones in actual regular elections. And we're starting at the municipal level because our view is let's start local, one less hacking risk to local elections that have the lowest participation and turnout. So they kind of need the help the most. We're about to start running legislation, different cities around the US that would authorize mobile voting for municipal elections specifically. So mayor, city council, school board, stuff like that. And you know, we've gone from this being a project inside of my foundation, test philanthropies to becoming what hopefully will be a very big movement. Right, because we're going to need to mobilize millions and millions of people to demand that they have the right to vote online because otherwise the status quo is not going to like it. Because typically people in power don't like making it easier for other people to gain power. And so I was lucky to give a TED Talk on it this year. It just came out last week. So that helps us make the case. Wrote a book about this called Vote with your phone. We moved the mobile voting project to its own separate entity with its own team and leadership and board. We're raising money. So I've put $20 million of my own money into mobile voting so far. Again, totally philanthropic, but passing these laws all over the country is probably going to take a couple hundred million dollars. And so we're starting to raise money and we're trying to build a movement. And if you think about every major right in this country that's ever been won, whether it's women's rights to vote, or the Civil Rights act or the Voting Rights act or same sex marriage, the American Disabilities act or anything else, because enough people stood up loud enough and long enough and demanded their rights, and eventually the status quo had to give in. And that's what we have to do here too.
A
Sure. A lot of people are wondering, does this help Republicans or Democrats more? Does it help moderates or Extreme candidates more. What are the.
B
You know, it's a good question. So it helps moderates only in the sense that ultimately more people voting means that the mainstream opinion matters more to politicians.
C
Right.
B
But what's interesting is, so one country in the world has been doing this for 20 years now, Estonia. And I went over there a few weeks ago and got to meet with everybody who works on this, and I was talking to some political scientists and what they told me was really interesting, which was, it turns out that there really is no specific party in Estonia that benefits from mobile voting more than another democracy benefits because turnout is significantly higher, especially in local elections, and whoever candidate loses an election blames the Internet voting for it. But ultimately you would think these would benefit or that would benefit. And in the very early days that might be the case because some people are more apt to do something their phone than others. But at least the data Estonia shows that over the long haul it evens.
A
Tell me more about Tusk Ventures, the venture arm that you invest out of today.
B
My first exposure to tech was, was Uber and then again Clear. And in both cases I took equity in part for doing my work. Those paid off pretty well. And I had this thought that there really wasn't a venture fund out there focused specifically on startups and highly regulated industries where you go out there and solve their regulatory problems. You have venture funds that can help you with engineering or growth in marketing or hiring or whatever it might be, but really no one from politics had ever started a VC fund before. And so I launched my first fund, Tus Ventures in 2016 and Seed Series A. And we invest in early stage startups in highly regulated industries where we believe that we can solve their regulatory problem for them. So things like I've mentioned On this podcast, FanDuel, we help legalize daily fantasy sports betting, lemonade, we got them their insurance licenses, roe, we legalized prescription via text, and so on. So companies like that Circle, Coinbase, Bird Latch, Alma ended up doing three funds, about 300 million AUM total. And then about six months ago, I kind of realized something, which was the reason why those founders took our money was not because we needed our money. Those were all highly competitive rounds. But they wanted the regulatory help and that's how they, that's how they got it. And it kind of occurred to me that like, why couldn't I just do what I did with Uber and Clear and not deal with all of the effort involved in raising capital, managing a fund, and then ultimately returning 80% of the profits back to the investors, which they have every right to. I realize I don't need any of this. And so I now said I'm not taking outside capital anymore. And we changed our model a bit, so we are now doing kind of a hybrid. So it's what we did with Uber and with Clear, where we're taking equity again in return for our work. But we're also taking pro rata and I both have my own capital and then I have partners who are my LPs at the fund to do SPVs in any particular round so that we can deploy capital as well.
A
You're the only VC I think I've ever met that sees regulation as an exciting thing. Why do you love regulation so much?
B
I love politics, man. I think it's so interesting and I think hopefully over the last 45 minutes, for you and for the listeners, I've painted a picture that politics is about psychology. It's about human behavior, it's about emotion, it's about belief, it's about economics, it's really intellectually complex and it plays out in real time. It's important. The things that we do can impact millions, if not tens or hundreds of millions of people. And so it feels like your work really matters. And so that's why I've always been drawn to politics overall. And then to me, you know, like I said, there are a lot of similarities between the campaign world and the early stage startup world. So I felt like I already kind of understood it and felt like I was in a unique position to a help really legalize disruptive things and so help prevent the kind of corruption that you see in French interests use, where they use their political power to block innovation and block new ideas. And we could be a force against that, which I think we are. And then also just from an economic opportunity, you know, I got really lucky that I just made enough money both through my original consulting firm and through the Uber and Clear and whatever else. And I have a very, very high risk tolerance that I was able to go pursue something that sort of hadn't been done before, in part because, you know, no, you don't really get rich working in politics, right? You know, you can do what I did, you start a firm and you can make some money. But it was just luck that Travis couldn't afford my fee and it was luck that I said yes. And it was luck in some part that Uber became Uber. A lot of work too, but luck. And that made me a whole bunch of money. And the truth is, I didn't grow up With a lot of money. I worked in government for a long time. I didn't make a lot of money. I don't need that much money for myself. And so I'm really happy to just deploy it, whether it's into things like mobile voting and hunger, or whether it's into building new businesses and taking risks on things like venture capital, where I think that I have the ability to do it. So there's probably other people in politics like me who would like to do what I'm doing. I just happen to A, amass the capital, do it, and then B, have the risk to owners to do it.
A
You've went against some of these taxi lobbies, against the tobacco lobby in New York City. And I always wonder and I want to really understand the opposite side and essentially how do they sleep at night? But what is their frame of reference? How could you be for something that hurts people? How do they get themselves aligned with these kind of missions?
B
It's a good question and I ask myself that a lot too. And I think the answer that I have come to realize is it's one of two things. Either because again, we all have different perspectives. Part of links human beings interesting is there's 8.5 billion of us and we all have sort of different DNA and different, different thought processes. So there are things like, for examp example, we've turned down a bunch of different things over the years because I didn't want to work on it for that reason. So whether it was the NRA or Philip Morris or Juul or the Sackler family, you know, Sam Bankman fried things I just didn't want to be involved in. I do a lot of gambling stuff, right. I work in that sector quite a bit. And there are certainly people who will say, how could you do that? It is a dangerous, addictive product that can ruin people's lives. And my view is people have the right to choose to gamble if they want to. They've been gambling since day one. And if the choice is to have it legal and taxed and regulated or illegal, you're better off with the former. But I understand that not everyone shares that view and that's my individual moral compass. So one is everyone's got their own moral compass. And it might be that someone who support something that we think is wrong genuinely feels otherwise, or the other one is they just don't care. I mean, there's very much a zero sum mentality that some people have. I would say the president first among them. That is life is a competition. It's everyone against everyone else. And the point of the competition is to amass as much wealth and as much status as possible, as much luxury as possible, and you do what it takes to get there. And those are the rules of the game. And so if you truly have a zero sum mentality and approach to life, you don't care. And if you don't care, then I guess you do whatever you want.
A
What do you wish you knew before starting at the intersection of startups and.
B
Politics for me is more on the the investing side, which is I like big ideas, I like kind of political challenges. I'm an optimist and as a result there are things that I jumped into that ended up being really unsuccessful because I didn't know better, right? Because I let myself think, oh, this is such a cool idea, of course it will succeed. And so for example, I funded the incubation personally. Not even the fund of a tele religion app where the idea was to sort of bring religion online and so that you could connect people in different ways and different ways of monetizing or whatever else. And in my mind that made total sense. And I put $4 million of my own money into building it and it was a disaster. I mean, it failed almost immediately. And other people around me said to me, like, I don't think this is a great idea. But I was like, no, no, no, I'm so smart. I did Uber this and this and that. Of course I know. And like I was arrogant, I was foolish and I paid a price for it right now, luckily I could afford it, but nonetheless, we started off this podcast by talking about knowing what you don't know. There are times where I haven't known what I don't know and I've really, you know, had to pay the price for that.
A
Bradley, this has been a masterclass on politics and startups. I've been wondering about these questions for probably decades. If I think.
B
Glad I got a chance to help you.
A
Thank you. Thank you for answering them and I look forward to shutting down soon.
B
Yeah, we'd love to. Thanks David.
A
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Podcast: How I Invest with David Weisburd
Host: David Weisburd
Guest: Bradley Tusk (Tusk Ventures)
Date: August 20, 2025
Episode: E202
This episode features a comprehensive and candid conversation with Bradley Tusk, the political strategist and venture capitalist most famous for his work with Uber's regulatory battles. Tusk shares insider perspectives on how startups can navigate and influence the complex world of regulatory and political engagement, drawing on his rich experiences from campaign politics through to venture investing. The discussion covers the “playbook” for startup lobbying, realpolitik insights, the evolution of lobbying tactics, the crypto lobby’s ascent, mobile voting, and the moral quandaries of political work.
[00:00–02:45]
Origin Story: Tusk describes joining Uber at its Series A stage and facing the entrenched, politically powerful taxi industry.
Strategy: Instead of seeking permission, Uber entered cities unannounced and responded to regulatory pushback by activating their user base to contact politicians.
Result: Example in Washington D.C.— Uber mobilized 50,000 users to pressure city council, defeating hostile legislation and passing pro-Uber regulations.
"The only way that we could counter taxi’s power...was to do it with our customers...50,000 of them reached out to their city council members...and it worked so well that not only did the bad bill die, we put it on our own bill, which passed nine to nothing."
— Bradley Tusk, [01:01]
[02:45–04:44]
Political ROI: Every policy output is a function of a political input; politicians almost always act to maximize their chance of re-election.
"Every policy output is the result of a political input. Every politician makes every decision solely based on winning the next election and nothing else."
— Bradley Tusk, [02:50]
Bloomberg Exception: Tusk contrasts the typical politician with rare exceptions who act on first principles, using Michael Bloomberg’s controversial but principled policy decisions as examples.
[04:44–07:44]
Identifying True Believers: Look for evidence of personal passion or previous acts of independence to identify politicians who may act outside pure self-interest.
Case Study: Bloomberg supporting the ground zero mosque and smoking ban—taking deeply unpopular but principled stands.
"There are occasionally the Mike Bloomberg's of the world...they’ve shown independence before, they're not total party hacks, they've expressed, you know, a personal story about an issue they truly care about."
— Bradley Tusk, [06:43]
[07:55–10:35]
Program Example: Tusk’s foundation campaigned for universal school meals—popular in polls, but not politically rewarding because the beneficiaries don’t vote or wield influence.
"There's no actual political ROI for doing it, because the kids can't vote. They're kids, and the parents don't vote, because either they're not citizens or they work hourly jobs..."
— Bradley Tusk, [09:22]
[10:35–14:11]
Beyond “Suitcase of Cash” Stereotype: Effective lobbying is now multifaceted—combining lobbying, media (earned, social, paid), grassroots campaigns, opposition research, and more.
"The days that you were kind of joking about... where a guy knows a guy... those days are gone...the way the campaigns are won today is much more multifaceted."
— Bradley Tusk, [11:14]
Psychology as Tactic: The approach is situational; much of the work involves understanding what motivates each individual policymaker.
[14:20–19:52]
Assessing the Situation: Startups must be humble—acknowledging what they don’t know—and analyze laws, risks, opponents and allies, and messaging.
Find Your Allies: Customers worked as Uber’s lever, but in other verticals, benefits may attract advocacy groups or business partners instead.
Messaging: "No one cares if it’s good for you. You have to credibly make public policy better."
Jurisdiction Stacking: Start in easier regulatory environments to build precedent, before tackling tougher markets.
"If you just go in there and say, you should legalize this thing because it's good for me, like, nobody cares about that...you have to make the case that public policy ... is advanced because of the work that you are trying to do."
— Bradley Tusk, [18:22]
[19:52–22:12]
[22:12–24:58]
Why Crypto Won: Unprecedented financial resources, strategic targeting (“pick a few people and make huge examples”) and an activated, ideologically motivated user base.
Impact: Outsized political influence by smartly spending big in high-stakes races, sending a signal to all politicians.
"Your $40 million investment might have 4 billion in value...you were able to change perception and behavior by lots of the other 99 senators because they saw what just happened..."
— Bradley Tusk, [23:18]
[24:58–30:04]
Building a Party: Enormous, long-term investment required; biggest opening is for a “sane center” party, but voter behavior and primary systems favor ideological extremes.
"The problem is that 70% on any given issue tend to not vote in primaries...the only election that really ever matters is the party primaries..."
— Bradley Tusk, [27:31]
[30:04–35:20]
Vision: Making voting easier to change the composition of the electorate and break the hold of ideologically extreme voters.
Progress: Built a robust, open source mobile voting system; efforts underway to legalize in municipal elections.
Impact: More mainstream, moderate views could gain influence as voter turnout increases.
"If you put voting on people's phones, will they do it? And the answer was, yeah, you make something easier, more people do it."
— Bradley Tusk, [31:20]
[35:20–37:25]
[37:25–39:50]
[39:50–42:01]
[42:01–43:23]
Mistakes: Arrogance about unfamiliar markets led to failed investments—humility and self-awareness are critical.
"We started off this podcast by talking about knowing what you don't know. There are times where I haven't known what I don't know and I've really, you know, had to pay the price for that."
— Bradley Tusk, [43:17]
On lobbying’s shift:
"The days...where a guy knows a guy and he makes a call and everything kind of gets fixed, those days are gone." ([11:14])
On moral calculus in lobbying:
"Either...someone who supports something that we think is wrong genuinely feels otherwise, or the other one is they just don't care...there’s very much a zero sum mentality." ([41:07])
On mobile voting & turnout:
"Turnout, for example, in an election in Seattle tripled. So, okay, we established, yes, the hypothesis is right." ([31:30])
On startup humility:
"Any founder actually that really, truly believes that going in...I will not invest. That will not work with you." ([15:38])
Bradley Tusk’s tone is frank, witty, and simultaneously optimistic and realistic about the mechanics of politics and startups. The episode is a “masterclass” (as David calls it) on the intersection of money, power, innovation, and government. Listeners gain a pragmatic framework for startup lobbying, an understanding of the political incentive system, and inspiration to remain self-aware while navigating both worlds.