When Airbnb (ABNB) -) was founded in 2007 out of the San Francisco apartment of Chief Executive Brian Chesky and Co-Founder Joe Gebbia, all the two had to go on was a good idea: providing a more pleasant way to enjoy out-of-town accommodations than staying in a generic hotel room.
Now, 16 years into the apartment-sharing company's life span, it's a staple that can be found across 220 countries. But as with most new businesses, its founders experienced some critical bumps along the way.
Related: Here are the few cities where an Airbnb is (still) cheaper than a hotel
Chesky discussed his experience on the Oct. 9 episode of "The Diary of a CEO" podcast, highlighting several of the mistakes he made in the early years of Airbnb's development.
The CEO says that while the "addiction" to work he had at the time was very productive for the company, he felt guilty "any second [he was] alive but not working."
Loneliness was also mentioned as an issue Chesky faced, partly because he founded the company with, and hired, friends.
“No one told me … how lonely it would be, and it doesn’t have to be,” said Chesky. “When I started Airbnb, I started with my friends, then we hired people, and those people were our employees but also kind of our friends.
“As we got successful, then we became more of a corporation, there was a chain of command, there were more boundaries. … It becomes more formal. And that’s the moment your employees become your employees and less your friends, and that gets more and more isolating.”
Chesky learned a valuable lesson from his experience, eventually turning some energy away from the business to focus on his family and friends.
“We need to have some healthy relationships to probably make good decisions,” he said. “Lonely leaders are probably not the best leaders.”
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