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Politics, Innovation and the Built World: My Conversation With The Fixer

You may not have heard of Bradley Tusk but you definitely know his clients. He is the political strategist turned technology investor that has worked with companies like Uber, FanDuel, Bird, and Lemonade as well as run campaigns for New York Mayor Michael Bloomberg and disgraced (and jailed) former Governor of Illinois Rod Blagojevich. Now he just wrote a memoir-slash-political-influence-DIY book called The Fixer: My Adventures Saving Startups from Death by Politics and was the keynote speaker for our last Propmodo Live event.

I’ve followed Bradley’s rise into the top levels of venture investors after I interviewed his Head of Investments and Partner in Tusk Ventures Jordan Nof a few years ago. When I found out that he was going to be the headliner for the event I pushed to be the one on stage with him so I could ask him some burning questions. I mean, here is a guy that has been in the trenches for some of the biggest political fights of our time that don’t involve a presidential race (although it is rumored that Bloomberg is eyeing a run at the 2020 presidency and Tusk has agreed to be his head of strategy so stay tuned). Not only was Bradley able to navigate what could be two of the most entrenched, financially charged places in the United States, New York and Illinois, but he was also able to harness the power of small technology companies against corporate giants with healthy lobbying budgets. If you need to know how to get something done when it came to dealing with the government, this is your guy.

His firm has been incredibly successful with multiple unicorns in its portfolio already. For me, this shows how many of tomorrow’s most valuable companies have to burn down the current economic ecosystem in order to make way for new types of growth. Doing this means finding ways to assert power politically, both against established companies that stand to lose their footing and towards regulators who see no reason to go out of their way to do more work.

Bradley did not make the transition from being a political strategist to a technology start-up advisor working primarily for company equity intentionally. As he says in his book:

“After starting a consulting firm, I was sitting in a meeting one afternoon about Walmart’s zoning issues. The phone rang and a friend of mine said, “Hey. There is a guy with a small transportation startup. He is having some regulatory problems. Would you mind talking to him?” I became Uber’s first political advisor that same day and spent much of the next five years kicking the shit out of the taxi industry all over the United States to make ridesharing legal everywhere. I also made a bet that paid off pretty well, taking half my fee from Uber in equity when the startup was still in its infancy, a bet that ultimately produced 250-fold returns.”

The reason that there are not many political advisors that focus on emerging tech startups is that these two worlds have opposite appetites for risk. “Most of the people that start in politics don’t want to take the risk of consulting startups,” Tusk explained. It also has a bit to do with the disconnect between the business world and what matters to those in the public sector. Bradley said, “When I was first consulting I was talking to a lot of companies trying to convince them that they needed help with regulators and I would often get a similar answer, ‘You don’t understand, I went to Stanford, I was in Y-Combinator, John Doerr is on my board, when regulators see that they will do whatever I want.’ I would just tell them I am pretty sure that politics doesn’t work like that.”

The failure to understand the political landscape is not exclusive to tech startups. Real estate is one of the assets most heavily influenced by all levels of regulators but besides hiring a lobbyist I have heard very few innovative strategies about influencing regulation from the property industry. Bradley’s successes show how a little bit of strategy can go a long way when it comes to convincing elected officials and new technologies are providing more options than ever to make that case. He told me, “The fundamental point of the book has very little to do with technology. It is about what politicians are really like, how they make decisions and how they can be influenced. With the exception of Mike Bloomberg, I have never met a politician that wasn’t a desperately insecure, somewhat self-loathing and couldn’t live without the validation that comes with holding office. It is oxygen for them. Being in the spotlight, even something low level like state representative is the most important thing to them. Every decision that they are going to make revolves around ‘Am I going to be able to win my next election,’ and that is it.”

Framing the incentive this way helps create a much clearer picture of what argument needs to be made in order to get the attention of government officials. The American political system also dictates which part of the process is the most critical to politicians. “Because of gerrymandering the real action takes place in primaries,” Tusk told the crowd during our talk. “Even in a place as big as New York City many council members only win their district by twelve thousand votes so you just have to show them that the people supporting your side of the issue can sway that number.”

This is exactly what Tusk Ventures did for Uber when he was finally able to get them into Manhattan. The startup wanted to make sure politicians understood how many people preferred Uber to the taxi-cab medallion system that New Yorkers had loved to hate for decades. So Uber added a “DeBlasio Mode” for any of the users in the NYC area. Clicking this tab would limit the number of available cars and spike wait times, showing the possible effects of a new regulation that was being passed to protect the taxi interests in the city, and then it provided the ability to write an email to council members telling them of their preference for ride sharing to exist. The result was a flood of tens of thousands of emails to offices of every elected official involved that eventually resulted in dropping the regulatory approach to this new, popular service.

His suggestions for those of us who want (or more likely need) to change regulations or create new ones start with framing the narrative. Finding the right way to sell the idea that appeals to those that vote for a politician is critical to the rest of the campaign. Then, it is about finding people that believe in this narrative enough to make their voices heard. “When we helped FanDuel we realized that even though the population of users was much smaller than that of Uber, they really loved fantasy sports and would do a whole lot to protect it if they knew how to help,” Tusk said.

In this process, Tusk advises to not be afraid, even if your political advisors are. “Lobbyist think in terms of political capital. They want to utilize it as best as possible but never use so much that they run out. That means not burning bridges or rocking the boat. That might be what is best for them but it is usually not what is best for a company.” That also means not being afraid to go negative.

It was easy for me to tell that this is a place where Bradley’s personality helps him. He is not afraid to make bold statements but never seems to get emotional about the conflicts that he has had. For him, it is all just part of the game, not something to be taken personally. Bradley doesn’t seem to take all of this negative energy around with him, switching effortlessly between conversations about testifying in front of a grand jury and his family life with his wife and two daughters. “The vast majority of people are totally afraid to piss officials off,” he said smiling. “It is not about playing the game in a certain way, it is about making people understand the negative consequences of not doing what you want.”

Bradley Tusk is one of the rare people that likes a good fight. He sees opportunity in it. He wears a pair of scratched up cowboy boots that look like they have been to hell and back, probably because that is exactly where they have been. Just like his boots Bradley seems perfectly fine with taking his licks and wearing them as a badge of honor. Luckily for all of us, we can learn from Bradley’s battles without having to go through them ourselves.

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