False economy What’s in it for me? Understand what makes the

The CEOs of Uber and Airbnb are 
determined, 
but 
sometimes 
court 
controversy.
Bill Gates and Mark Zuckerberg will be 
remembered as two giants of the entrepreneurial 
world. But both are shy and softly spoken, not 
the stereotypical brash and fast-talking CEOs.
The CEOs and co-founders of Uber and Airbnb, 
Travis Kalanick and Brian Chesky, are a 
different kettle of fish. Both are charismatic and 
sharp speakers.
Famously, Kalanick clashed with Christiane 
Hayashi, then director of San Francisco’s Taxis 
and Accessible Services Division, who tried to 
block Uber’s early expansion in San Francisco. 
The taxi drivers Hayashi served were up in arms 
because while they were heavily regulated, 
Kalanick’s company seemed to dodge every rule 
in the book. At one particularly heated meeting, 
Hayashi felt the Uber executives were 
“obnoxious,” while Kalanick described Hayashi 
as full of “deep anger” and “screaming.” His 
willingness to wage this war made it clear that 
Kalanick was not afraid to court controversy.
On the other hand, his style can also be 
inspiring. Fans of Uber rallied in his support 
when the company was locked in battle with 
local government bodies in places like New York 
City.
Meanwhile, Airbnb’s Brian Chesky was so 
charismatic that after speaking once at a 
conference hosted by the investment bank Allen 
and Company, he found himself invited to the 
bank’s yearly soiree. There he worked his magic 
and could promote Airbnb to real powerbrokers.
However, although Airbnb and Uber have 
connected people in bold new ways, their 
methods are controversial.
Uber, for instance, doesn’t actually employ its 
drivers, who are technically independent 
contractors. This means the company avoids 
having to provide benefits such as health 
insurance, which employees of large companies 
are entitled to.
And on one occasion, Airbnb publicly promised 
to compensate a host known as “EJ,” whose 
apartment had been wrecked by Airbnb guests. 
However, the company didn’t actually deliver on 
this promise, and so EJ mounted an online 
campaign to put public pressure on it. 
Eventually, the controversy forced Airbnb to 
change its insurance conditions for hosts.
The lesson is clear. A CEO’s ability to charm 
and force a deal can get them to the top. But it’ll 
likely make a few enemies along the way too.