Bradley Tusk began his career in politics before transitioning to helping high-profile startups dismantle legal barriers and take on entrenched interests. As he lays out in his new book The Fixer: My Adventures Saving Startups From Death by Politics, Tusk's self-styled job is to help companies do the illegal--and make it legal. His first major client was Uber--which was in the midst of a city-by-city war against local regulations that at times (such as in the odd case of Miami) prohibited it from operating.

Tusk went on to help Lemonade launch its disruptive insurance model, legalize on-demand cannabis company Eaze in some locations, and develop strategy for the constantly under-siege FanDuel and DraftKings. "Confession: Uphill political fights are kind of my thing," Tusk writes in The Fixer.

Inc. spoke with Tusk about when to push the limits, how to deal with extreme stress, and his unique path to becoming the go-to consultant for turning not-quite-legal startups into thriving above-board businesses.

Inc.: How'd you carve out this position of being a political fixer for startups?
Bradley Tusk: I had good experience early in my career working for New York City Mayor Mike Bloomberg--and bad experience working for Rob Blagojevich [the former governor of Illinois, who was impeached in 2009, and against whom Tusk, who was deputy governor, testified], which showed me what can go wrong.

A friend called me saying there's a transportation startup whose founder wants to talk with you. I got really lucky when Travis [Kalanick, co-founder and then-chief executive of Uber] said, "I can't afford your fee. Will you take equity?" I helped Uber navigate local politics, and thought it was fun--and had potential to be sort of lucrative. Before long, other companies, like Airbnb, started having regulatory problems.

So, since then, you sort of specialize in keeping startup founders on the right side of the law? Or is it more about finding the limit of how hard to push when regulations are in the way?
Yeah, there are moments of, "is it ethical or not?" There are also times there are fights that are perfectly ethical but you're not going to win. If you're going to disrupt an industry, you have to know: Is this a winnable fight? Also: What is it going to cost me? One of the best things that founders can do from the start is to consider who you are going to be pissing off. You can make decisions that can save you lots of heartache.

What's the craziest thing that happened working with Uber?
Probably the de Blasio fight. [In 2015 New York City mayor Bill de Blasio supported a proposal to cap growth of the number of Uber drivers at 1 percent a year.] Never in the history of New York City have the mayor and the city council president announced something together and it didn't happen. We only had a month to do it because they just wanted to ram it through. We came at him from the left with a huge media campaign, and framed it as "This is racist, you are hurting black and brown people who rely on Uber." No one had ever tried calling him on it. We made everyone so crazy. We created a de Blasio option on the Uber app, which added a 25-minute wait time [to show users what would happen if the cap were passed]. We raised such a stir that individual council members were saying, "I don't need this."

The TV ads were everywhere for a few weeks--and really appealed to customers to reach out to their representatives. Most people don't even vote in local elections, so how do you get customers to actively advocate for your company, and to pick up the phone to do it?
It doesn't work for every startup. They have to think, "I love what you are doing and I don't want that taken away." It works for fantasy sports. I don't see people starting a campaign for Dropbox. What Uber and FanDuel have shown is that you can get people to engage. People who never show up to vote in a city council primary, will advocate over Twitter or email if you make it easy for them. Technology can help the situation. We should all be voting by phone. That's something I'm really interested in promoting.

You were interviewed by the FBI during the Blagojevich affair...while your wife was in labor. So I guess you aren't so bad at handling stress. Any pointers?
The older I get the more I realize that when I know myself, I make better decisions. I know I'm socially awkward, so I just don't go to parties anymore. But I do really get a rush of adrenaline when I'm in a stressful situation, and I'm good at harnessing that. People in technology and politics are both often the sorts of people likely to get something out of that rush. It's our drug.