Hotelier Trump, who has also been accused of stiffing some contractors himself, told CNBC last year that he was trying to stop the use of Airbnb in his buildings — but he also said that he wouldn't want to regulate them out.
"A lot of people are happy with [Airbnb]. A lot of landlords are liking it a lot," Trump told CNBC. "And then of course there are some groups — hotels in particular — that aren't. As to whether or not it should be regulated, I don't like regulation. I'm not a person that believes too much in regulation."
Linda McMahon, Trump's pick to lead the Small Business Administration, has also called for more certainty about regulations for entrepreneurs. Elaine Chao, who Trump has tapped as U.S. transportation secretary, was favorably received by Uber and Lyft.
Trump's campaign, as well as his opponents', used Uber to get around this year.
'There needs to be safety nets'
The new administration's comments are a departure from the views of current U.S. Labor SecretaryThomas Perez, who told CNBC last year that the gig economy presents "false choices" between regulation and innovation.
"I hear some people who say that, well, we either innovate or we regulate and the best way to help build the 'Ubers' of the world is to make sure that there's no regulation," Perez said. "That's just flat wrong. That's a false choice."
Under the Obama administration, "gig" work has spiked: Over the past decade, contingent workers have increased by roughly one-half and now make up 16 percent of the workforce, according to a study conducted by researchers Larry Katz and Alan Krueger and cited by the Federal Reserve.
But calls for more regulation have threatened to unravel the growth of the freelance economy.
Hundreds of Uber drivers in two dozen cities have campaigned for a hike in the minimum wage, for instance. Workers at Instacart have sued the company over their classification as independent contractors and alleged the company mishandles their tips. Other platforms have faced different regulatory hurdles: New York lawmakers, pressed by tenants' rights groups, have said that Airbnb is breaking the law with its services.
While many of these battles take place at the local level, there needs to be some federal involvement for contractors that work across state lines, said Rishon Blumberg, cofounder of 10x Management, which connects companies to freelance technologists.
"I do think there needs to be some legislation — that there needs to be safety nets," Blumberg said. "I don't want to call it 'benefits,' per se, but if a worker spends a fair chunk of time working for a company, then the company would have to contribute into a benefits pool."
Even without federal intervention, Blumberg said he expects that gig economy companies will begin to self-regulate. One example is Hello Alfred, an on-demand personal assistant platform that treats its workers like regular employees, and was visited this month by Labor Secretary Perez.
"This is a seismic force moving in one direction that transcends administration, that has to do with how successful these business models are," Hello Alfred CEO Marcela Sapone said. "I think the Trump administration will potentially not weigh in on the issue. When you have a growing share of the economy that doesn't have health care built into their employment choice, you have to build that support system yourself."
But battles over benefits also illustrate how "gigs" like driving shouldn't be overemphasized by the new labor secretary, said Zappacosta. Instead, he said, the freelance economy should focus on empowering small businesses or skills-based entrepreneurship, as tasks like driving are replaced by autonomous vehicles.
"It's an unfortunate reflection of the regulatory environment that they want to provide benefits and can't," Zappacosta said. "They want to retain their drivers, but they are worried about the exposure. It's a good example of why we need to evolve what we currently have."
In many cases, this does mean simplifying regulation, Zappacosta said. One such example is Obamacare, which has forced small businesses to battle with convoluted and burdensome regulations, even as it helped younger independent workers stay on their parents' plans and buy from exchanges.
Trump campaigned on repealing Obamacare, but has since softened on some parts of the law.
"As long as there is some form of easy to access, affordable health care, [the freelance economy] will continue to burgeon," Blumberg said. "But obviously the benefits of being at a W-2 position increase."
— Reuters and CNBC's John Harwood contributed to this report.