In 2009, one year after Brian Chesky co-founded Airbnb, his company hosted over 21,000 guests. Six years later, the home-sharing company has served over 25 million. Despite intense criticism and legal pushback, Chesky is expanding.
Most recently, the 33-year-old New York native announced a move into Cuba following President Obama's loosening of travel restrictions. His first thoughts were "'We are going,' and 'When are we going?'"
"I called up our team immediately and they said, 'It would be great for us to get 100 homes in Cuba and I said 'What about 1000?'" Chesky said Wednesday on "CBS This Morning."
He sent a team to investigate options and they were welcomed with "open arms" by residents who had been sharing their home for a generation. "Casas particulares," similar to bed and breakfasts, are already a popular form of stay in Cuba.
But it's not so easy just yet. Americans must be traveling to Cuba for one of 12 reasons approved by the government - options Chesky said can be selected when checking out online.
"We worked with the State Department and some other organizations to make sure we could go there," Chesky said.
In late March, the Queen of England signed new rules permitting London residents to share their homes, updating more restrictive and antiquated laws. France and Portugal similarly overhauled laws to make it easier for locals to provide housing.
The company also announced their successful bid to provide housing for the Rio 2016 Olympic Games. Chesky said during the 2014 FIFA World Cup, one fifth of attendees, 120,000 people, stayed in over 18,000 Airbnb Rio homes.
The company has their foot in over 10 countries and over 34,000 cities, their most popular of which is France with nearly 50,000 homes.
But success has not been without a series of hurdles. In October of last year, New York Attorney General Eric Schneiderman's office released a report calling 72 percent of Airbnb listings in the state illegal. In April 2014, a California Airbnb renter was caught in legal crossfire when a rentee refused to leave her home.
Chesky said, "It's pretty hard to stop" people using the system in unintended ways.
"We tell them to check with their local landlord and their local laws and regulations and we try to provide a lot of education and we have a direct hotline for people to call us and I think over time we want to become more proactive," Chesky said. "One of the things I'm looking forward to here in New York and cities around the country is to actually have more proactive partnerships with landlords so we can actually work together with them."
In May 2013, New York officials fined Nigel Warren $2,400 for violating the city's illegal hotel law. In both the San Francisco debacle and Warren's, Airbnb stepped up to help, but Chesky said, "the fundamental problem" is not every U.S. state has home-sharing-friendly laws.
"There are laws written for business like hotels, there are laws written for people for how to live with roommates and Airbnb is this thing in between, it's this third category: people acting as businesses," Chesky said. "And so for many, many, years there were no real laws written for it so people tried to put somebody in one bucket or the other."
Despite troubles they've faced, Chesky said the "sharing economy" has become a huge form of work in the 21st century.
"The notion that in 60 seconds you can suddenly be entrepreneur, you can share home, your car, anything in your life that hasn't been monetized before, you can actually share with somebody," Chesky said. "It's really the notion that a person can become micro-entrepreneur."