Last week Airbnb, the home rental service, caught a break when a judge tossed out a subpoena by the New York attorney general for the names of 15,000 Airbnb hosts. It’s illegal under New York law to rent your apartment out for fewer than 30 days, something the AG, Eric Schneiderman, believed Airbnb was enabling on a massive scale. For its part, the company has protested that such laws only apply to traditional businesses, not its users (“there are no laws written for microentrepreneurs,” Airbnb CEO Brian Chesky has opined), and that the AG’s demands were too intrusive in any case. The judge accepted the latter argument, if not the former.

The victory aside, Airbnb’s legal problems are far from over—Schneiderman vowed to submit a narrower subpoena that would presumably pass muster with the court. But, then, Airbnb’s main strategy for dealing with regulations it dislikes has never been so much legal as it is political. Amid the company’s battle with Schneiderman, an Airbnb-affiliated group called Peers gathered more than 200,000 signatures for a petition urging the state to ease up on short-term rentals. According to the San Francisco Chronicle, Peers also ran a crowdfunded ad touting the virtues of home-sharing and dispatched hundreds of zealous Airbnb users to the offices of local politicos, armed with “their personal stories about the impact home sharing has made in their lives.” The company and its various allies have ginned up similar efforts in San Francisco and Los Angeles—suggesting that, win or lose in court, they see public opinion as the more important arbiter.

Every tech boom has a moment when utopian giddiness gives way to the messy reality of running a business. But that moment has proven far more painful in this boom, for two reasons. First, companies like Airbnb have honed in on parts of the economy where powerful regulators have traditionally deterred new entrants. Second, and largely as a result, the upstarts must not only innovate with their technology and business strategy, but also when dealing with the government officials who control their fate.

Unfortunately, not every startup has covered itself in glory amid this new world order. In fact, the companies doing the most innovating on the regulatory front appear to be guided more by their libertarian ideology than what’s best for their customers and the economy as a whole—or even, at times, for themselves.

Like Airbnb (and for that matter eBay and PayPal during the 1990s), the popular car service Uber defines itself as emphatically not in the business it appears to be in for the apparent purpose of eluding regulators. CEO Travis Kalanick is fond of asserting that Uber is a technology company rather than a transportation company, and therefore shouldn’t be regulated the way taxis are. Like Airbnb, Uber also invites its diehard customers to mau-mau regulators on whom this distinction might be lost. As Mark Egerman, a former Consumer Financial Protection Bureau official and recent startup founder, sums it up, the Airbnb-Uber strategy is, “Get super popular, ignore the laws, and if you try to enforce them, we’ll use the power of the bully pulpit.”