Uber and Airbnb leaders don’t share key traits
Airbnb and Uber are the twin pillars of the sharing economy, two enormously successful startups in San Francisco that have transformed entire industries.
But that’s perhaps where the similarities end. For if Airbnb is the pleasant waitress who cheerfully offers you an extra cup of coffee, Uber is the Soup Nazi, who behaves as if the customer is lucky to even get a table.
To a large degree, each company reflects the persona of its founder/CEO. By now, any avid follower of Uber knows that Travis Kalanick and his fellow executives at the app-based ride company revel in being brash. From bullying journalists and antagonizing regulators to disparaging their own drivers, Kalanick and his cohorts seem to enjoy being bad boys.
Challenging entrenched industries is not for the faint of heart, so being a bit of a jerk is probably necessary to succeed. Or is it? Brian Chesky? doesn’t seem to think so.
In many ways, the Airbnb co-founder is the anti-Kalanick. Chesky is affable, self-deprecating, and seems genuinely as shocked as the next person that his startup has grown into a global phenomenon.
“Airbnb is the worst idea that ever worked,” Chesky said last week at the PricewaterhouseCoopers Corporate Leadership Breakfast, an event to raise money for Larkin Street Youth Services.
Unlike Kalanick, who was already a successful entrepreneur before he founded Uber, Chesky is a startup novice. So maybe Chesky owes a good deal of his humility to his relative lack of business experience.
“Growing up, I’m not sure I
even knew what the word entrepreneur meant,” he cracked.
Chesky started his career as a designer in Los Angeles. But he quickly grew restless.
“One day, you’re at a crossroads,” Chesky said. “I would imagine the next four years of my life looking like the past two years, and that terrified me.”
So with $1,000 in the bank, Chesky quit his job and moved to San Francisco, not exactly sure what he wanted to do.
While sharing an apartment with some roommates, Chesky thought they could occasionally rent it out to strangers. They would even provide an airbed — hence the “Air” in Airbnb.
“We had a lot of space,” he said. “I bet we could make a little money.”
The idea, he said, was not new. Before hotels came into existence, people like Chesky’s grandfather regularly stayed overnight in boarding houses.
Yet Chesky’s grandfather didn’t have access to sophisticated software that automated the business of matching renter to rentee. Airbnb was so fundamentally new that no one, not even Chesky, knew exactly how to define the market.
“We tried to figure out the number of airbeds sold each year, and we thought that was the market size,” he said.
Selling investors on the startup was tough work. Chesky recalled meeting an angel investor at a cafe. In the middle of the meeting, the investor left the cafe with half of his smoothie still sitting on the table and never returned.
Such rejection can keep a man humble, no matter how successful he becomes.
“People ask me what keeps me up at night,” Chesky said. “Is regulation my biggest problem? Absolutely not. It’s how do I continue to lead this rocketship?”
Chesky is in the hospi- tality business, so it probably makes sense for him to be a nice guy. Staying in someone’s home for a few days is inherently a more intimate experience that riding in someone’s car for a few minutes.
But listen to Chesky and it becomes obvious that he is just cut from a different cloth than Kalanick.
While Kalanick seems to relish confrontation, Chesky doesn’t even like the word “disruption.”
“It doesn’t sound like a good thing,” he said. “I was a ‘disruptive’ kid growing up.”
But Chesky also speaks to a broader mission. In a time when technology is automating jobs and replacing people, companies like Airbnb and Uber are putting a measure of control back to the individual, essentially creating a new class of “microentrepreneurs,” he said.
In other words, Airbnb doesn’t just benefit Airbnb but everyone else (not counting those who complain that Airbnb guests keep them up at night, turn scarce housing stock into vacation rentals or are squatting in their homes).
“I totally get that there will be unintended consequences” to what they are doing, Chesky said. “But we really believe that technology can improve the capacity of people, that through the sharing economy we can bring back the community atmosphere.”
Chesky’s efforts seem to be paying off. San Francisco recently passed a law that regulates Airbnb and other short-tem rental companies, a move that finally bestows a legal seal of approval to the company.
“It was a two- to 2½year process,” Chesky said. “I spoke to every supervisor.”
Meanwhile, South Korea recently indicted Kalanick for operating an illegal taxi service.
Uber, though, has been softening some of its edges of late. The company has hired former Obama adviser David Plouffe to run policy and strategy. Uber is also looking to hire its first executive to oversee corporate social responsibility.
Perhaps Kalanick realizes that disrupting things is not enough. To win over the general public, you need to make people to feel good about the business, a strategy that Chesky seems to already have mastered.