This Chicago host started in his parents’ Chinatown basement. Up next: a treehouse?

Some people move in with their parents to save money. This Airbnb host moved in to make it.

At a recent meeting of Airbnb hosts affiliated with Keep Chicago Livable, a nonprofit that advocates for more favorable home-sharing policies in the city, Milo Chan had a captive audience.

Chan was detailing his plans to fly to Texas to stay at a treehouse he saw listed on Airbnb. His summer trip wasn’t drawing envy because of the warm location or adventurous accommodations — several hosts balked at the idea, joking about whether the bathroom was also in the tree. It was Chan’s motivation for choosing the treehouse that had their attention: He wanted to learn about the design and the guest experience behind an Airbnb treehouse rental so he could replicate it.

“When it comes to Airbnb, creating the best experience through a really emotional, visceral connection is one of the most effective strategies,” Chan said. He figured that relatively low building costs, combined with the high price people would pay to stay in such a novel property, would make a treehouse a worthwhile investment.

That sort of creative and entrepreneurial thinking is common among many of Airbnb’s most successful hosts, who see endless opportunities with the platform. Chan spoke about his treehouse ambitions with a level of confidence that might suggest he had been managing Airbnbs for years. But Chan, 33, only got started on the platform in June 2017, when he and his wife, Chandra, listed their Chinatown apartment before moving in with Chan’s parents nearby.

Chan grew up in Chinatown, where his parents have owned a restaurant they still run. He still works there as well, but less so as his Airbnb business takes off. Much of his approach to hosting is explained by his upbringing: Growing up with two entrepreneurs, he picked up business skills here and there and learned a lot through trial and error.

“With this new sharing economy, people often don’t realize that they’re operating a business and specifically one in hospitality,” Chan said.

His own efforts notwithstanding, Chan attributes much of his success to help from others and sheer luck. When he first started with Airbnb, Chan’s mentor — who had five listings of his own — offered hosting advice, while his parents gave him a place to crash and became co-investors in subsequent properties.

Chan had also been nervous that Chinatown might not be a desirable location for guests. But his apartment was also close to McCormick Place convention center, which has seen an increase in business and tourism activity in recent years. Out-of-town guests often don’t know the difference between neighborhoods, Chan says, so his proximity to popular attractions meant his fears went unrealized.

While picking and investing in the optimal real estate came with significant financial risk, Chan was excited that he could “retire” from a traditional job, at least for now.

“Anyone doing this business is trying to create a lifestyle for themselves,” Chan said. For him, that lifestyle involves staying in palatial estates in Hawaii on family vacations, having the freedom to work and travel on his own schedule, and being inspired to explore new business ideas like building treehouse rentals.