Ex-Blackstone Exec’s Sharp Elbows Were Too Pointy for Airbnb

Laurence Tosi—the most prominent executive hired by a unicorn founder—is out at Airbnb Inc. LT, as he is known, clashed with Airbnb Chief Executive Officer Brian Chesky over vision and style. They both had what a banker might call “alpha personalities,” and Tosi was angling for more responsibility, including the chief operating officer title.

The two men’s visions for the company clashed, but they were reconcilable—if egos hadn’t gotten in the way.

Since starting Airbnb in 2008, Chesky has seen it as a design-centric company. He admired Walt Disney and would have the company brainstorm ideas by turning them into storyboards like in the movie business. For years, Chesky has hoped that Experiences, Airbnb’s effort to provide local activities for travelers, could turn into a workforce redefining product. It’s nowhere close. Instead, Experiences has struggled to break out. Broadly, Chesky has been advocating for keeping Airbnb’s warm, fuzzy and local feel.

LT, meanwhile, seemed to want to build a better Expedia. The company needed to get into flight-booking and integrate hotels. It should focus on revenue and cutting loses. When he joined the company, he insisted that Airbnb make a few focused bets.

Think of this as the conflict between what you tell your customers and your investors. Marketing vs. investor relatoins. Chesky vs. LT.

The messages, of course, need not be the same. Apple doesn’t talk to its investors about chamfers and bevels; they hear about margins and sales growth.

The problem with Airbnb (or what makes it so special) is that it’s such an earnest company. It’s not the kind of place, nor is Chesky the kind of CEO, that can talk about the mission one way internally and another way externally. Chesky fashions himself as a visionary, Steve Jobs-like showman. And he buys into his own hype.

Certainly, there are some real trade-offs between the two visions for the company. Adding flights to the platform tactlessly could dilute the power of the brand. There’s a big difference between running an airline and a ticket-booking service.

Belinda Johnson, a longtime executive, is taking the COO job instead. She’s been a key player at the company for years, and she has Chesky’s trust.

But the loss of Tosi is a clear blow for the business. Unlike Uber Technologies Inc., Airbnb had avoided drama and executive turmoil. No longer. Airbnb’s investor whisperer is gone. The man Steve Jobs once wanted to hire couldn’t keep the peace with his startup boss.

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