Uber and Airbnb were founded around the same time and helped kickstart what is sometimes called the sharing economy.
Now, Airbnb's CEO Brian Chesky is watching as his peer deals with one crisis after another.
When asked about the struggles of Uber CEO Travis Kalanick, Chesky framed the issue as being partly the result of young tech executives learning on the job.
"I think that all of us are on our leadership journeys frankly. I know Travis is. I've been on mine myself. i think we are all learning," Chesky said Monday at event hosted by The Economic Club of New York.
"I think there's a benefit to young people like us starting companies," Chesky added. "We can come up with novel ideas. But it also means we are learning on the jobs."
Uber is currently conducting an "urgent" investigation in response to a former employee who went public with allegations of sexism and harassment at the company.
Uber customers also took issue with Kalanick's decision to serve on Trump's business advisory council. And Kalanick was caught on camera arguing with an Uber driver.
"I must fundamentally change as a leader and grow up," Kalanick said in a statement after the video surfaced last week.
"We need mentors," Chesky said at the event Monday, noting that he has reached out in the past to business leaders like Warren Buffett and Sheryl Sandberg.
Uber is now in the process of searching for a COO to help Kalanick run the business, just as Facebook CEO Mark Zuckerberg did by hiring Sandberg in 2008.
Chesky says he has not spoken to Kalanick about "his challenges," but spoke favorably of the steps Kalanick has taken so far.
"I think he's doing everything he probably should be at this point, which is to say he's owned up to every problem," Chesky said. "Every time there's a challenge that broke out, he apologized, he's owned it and he seems to have established a step forward."
Uber and Airbnb are now the two most valuable U.S. tech startups, respectively -- and neither appears to plan on going public anytime soon.
"Our investors are very patient. None of them are anxiously waiting for us to go public," Chesky said of Airbnb during the interview, which took place at -- of all places -- the New York Stock Exchange. "At least right now we can take big bets as a private company."
Airbnb closed a $1 billion round of funding last week, giving it even more runway to stay private longer.