Traditionally, Kalanick has tackled obstacles with the same approach: ignore and proceed.
When he started Uber with a few friends in 2009, the idea was to create an app that would give town car drivers extra fares during their down time. It was less about starting a world-changing business and more about helping his friends get cool upscale rides.
But as the concept caught on, Kalanick had to face off against irate taxi commissions and politicians, groups that had managed to derail past tech startups hoping to get in the transportation game.
"This industry required a certain personality to change it, someone willing to stand up to regulators and change laws or make new ones," says Brad Stone, author of The Upstarts, which chronicles category-altering companies such as Uber and Airbnb. "So, the thing that made him and the company successful is now causing havoc."
That "thing" would be a take-no-prisoners approach to business that pervaded the culture inside the startup, attracting a sharp-elbowed lot: Goldman Sachs bankers, Amazon engineers, Google policy veterans. And it worked. In a mere five years, Uber would raise $1.2 billion.
For Kalanick, that "baller" lifestyle was less about the world of rapper Jay-Z and more about taking on the world with everyone lined up against you, says Chris Messina, who was Uber's developer experience lead and left last month.
"I got the feeling that early people at Uber have a sense of pride for their 'ballerness,' the willingness to go out and do (stuff)," Messina said.
But the havoc along the way would be a range of withering incidents that followed as Uber grew exponentially from Bay Area sensation to global force.
In December 2013, 6-year-old Sofia Liu was killed in San Francisco after being struck by the vehicle of Uber driver Syed Muzaffar. Uber's blunt reaction was to say that Muzaffar "was not providing services on the Uber system during the time of the accident," and it cancelled his account.
In February 2014, GQ published an article about Uber in which Kalanick was interviewed by Pitch Perfect author Mickey Rapkin. Calling Kalanick a "bro-y alpha nerd," he teased him "about his skyrocketing desirability, (which) he deflects with a wisecrack about women on demand: Yeah, we call that Boob-er."
In October 2014, Uber's French operations had to quickly pull down an online promotional offer that appeared to be targeting male riders by promising "incredibly hot women" as drivers.
Among those writing about that incident was Sarah Lacy of Silicon Valley-focused website Pando Daily. Lacy blasted Uber and Kalanick and deleted her app.
A month later, at an off the record dinner party with journalists, senior exec Michael grumbled that Uber should hire opposition researchers to dig up dirt on reporters it did not like, and mentioned Lacy. Buzzfeed published the comments. Michael apologized but was not fired.