Airbnb CEO Brian Chesky says his dad did him ‘a service’ by never complimenting him—it’s a lesson he’s kept while building the $82 billion giant

However, for Airbnb CEO Brian Chesky, a little tough love from his dad helped him overcome his fear of losing it all—and may have just been the secret sauce needed to drive success in his rental company.

“My dad never told me I was talented or smart, and he probably did me a service,” Chesky said on Simon Sinek’s A Bit of Optimism podcast. 

“He only rewarded effort… if you reward a child for being intrinsically good, they’re going to be afraid to try because they don’t want to disprove you. But if you reward effort, the only way to fail is to not give it your all.”

This lesson was especially needed during Airbnb’s early days, Chesky said, when rejection occurred often as investors weren’t quite sold on the company’s ability to scale. And Chesky couldn’t turn to his mom for some sympathy either—he revealed she, too, wasn’t afraid to tell him the hard truths.

“At that point, my mom said, ‘So I guess you don’t have that job with health insurance anymore.’” Chesky recalled to students at Stanford University’s Graduate School of Business. “And I said, ‘No, mom, I’m an entrepreneur.’ And she said, ‘No, you’re unemployed.’”

But instead of throwing in the towel, Chesky turned that tough love into motivation—and over time, it paid off for the now 43-year-old. Airbnb is now valued at over $82 billion.

Coins2Day reached out to Chesky for comment.

‘The role of a leader is to just get everyone to do their best’

As the CEO of a Coins2Day 500 company (Airbnb is ranked No. 382), Chesky has developed his leadership style into one that praises success. In fact, he told A Bit of Optimism podcast that he tries to help his employees “reach beyond their potential.”

“I think the role of a leader is to just get everyone to do their best, but not participation trophy best,” Chesky said. “I’m talking about better than you ever think you could. If I tell somebody you could do better, I’m not saying you’re not good enough. I’m saying I see potential in you that you may not see in yourself, and I know that we can do more.”

“I think so much of leadership is believing. I think the biggest gift a leader can give to a person is to believe in them,” he added.

Chesky learned this philosophy in part from the wisdom of his own parents, but also from mentors he sought out in his career—including former President Barack Obama. In fact, he recently said that he and Obama would speak on the phone once a week. The former president advised Chesky to be an intentional leader who thinks long and hard about relationships and is active with the impact he wants to make.

Billionaires bank on failure

Chesky isn’t the only founder—or billionaire—who has been outspoken about not being afraid of failure. 
For example, both Bill Gates and Mark Cuban have been open about their experiences with failure. While many ventures that weren’t successful aren’t well known to the public, they’ve both shared that the experience shaped who they are as business leaders.

In his book, Business @ the Speed of Thought, Gates encouraged people to embrace unpleasant news as evidence for change: “You’re learning from it. It’s all in how you approach failures. And believe me, we know a lot about failures at Microsoft.”

In today’s age, in particular, when founders are trying to navigate entrepreneurship in the wake of AI, it’s more important than ever to take risks, Cuban said in 2023. 

“Even though it seems like a lot and like it’s complicated, you have to be curious enough to figure it out,” Cuban said. Otherwise, “someone is going to kick your butt.”   

“It doesn’t matter how many times you fail,” he added. “You only have to be right one time.”