In May 2011, soon after Uber made its New York City debut, the ride-sharing startup faced staunch opposition from the Taxi and Limousine Commission and its advocates in City Hall. Travis Kalanick, the company's notoriously hard-driving chief exec­utive, was given the name of the one person he needed for the battle ahead-- Bradley Tusk.

Tusk, a former campaign manager for then mayor Michael Bloomberg, had a two decade career in politics that made him fluent in the obscure language that marks bureaucratic officials. It also didn't hurt that he had just started consulting with Walmart and AT&T, honing his ability to talk business. When Tusk got Kalanick's call, he didn't know much about Uber but figured, "What the hell--I can help."

Tusk ended up leading Uber's relentless New York City campaign, setting a new bar for how startups hurtling straight toward regulatory gray areas can bend ambiguity to their advantage. Since then, he's been selling his brand of Wild West optimism to other startups with his New York City-based political strategy firm, Tusk Ventures. He's now working with a variety of young companies--Handy, a housework platform with a contractor work force; controversial fantasy sports site FanDuel; and medical cannabis delivery company Eaze.

Tusk urges upstarts to think like political operatives from day one. He says they need to first understand the motivations of individual regulators, and then try to win them over ahead of launch. For example, politicians don't care about a company's customer-acquisition strategy; they're much more concerned with how they're perceived by the press or whether they can raise enough cash for reelection. "The more you can frame what you want as something in sync with their agenda-- or very much threaten the success of their agenda if they don't do what you want--the better your chance," says Tusk.

If a company decides it's not going to play by existing rules, it needs to weigh the consequences. "If you beg a regulator for forgiveness, probably not a big deal," says Tusk. "If you beg a U.S. attorney for forgiveness, bigger deal." He says apologize-later companies need to build a  passionate fan base. If lawmakers complain, a startup can leverage that public support.

Should regulators still threaten the company, Tusk has no qualms about playing dirty. "We can publicly question a particular politician's friendliness toward innovation: Are they from the future, or are they from the past?" he explains. "We can look at who their opponents are and also see if we can make the case for corruption."

This is a lever Tusk pulled deftly with Uber. He stoked the media narrative connecting taxi-medallion owners' political contributions with elected officials. Then, last summer, when New York City mayor Bill de Blasio tried to halt Uber's growth, the company ran paid TV ads implying that his proposal would kill 10,000 jobs. "What you have to figure out is what the local politics are, who the politicians are beholden to, and how to make the argument that what you're doing is for the public good," Tusk says. "Take them on in a language they understand, like a high-stakes political campaign."