Travis Kalanick
Kalanick would probably be identified as the leading man in this story if not necessarily its protagonist. Kalanick is, of course famous now—or, perhaps, infamous—as being one of the co-founders of Uber as well as its CEO during the years it went from zero to omnipresent, 2010-2017. The book draws to a close on the image of Kalanick becoming a billionaire several times over literally overnight on the day Uber went public.
Bill Gurley
While still basically able to walk down any street in most towns in America and remain completely unrecognized, Gurley is a rock star in the world of Silicon Valley. He went from analyzing investments on Wall Street to becoming an investment wizard as general partner at Benchmark. It was in that context that Gurley would go on to become a prime mover in the story of Uber as he was one of its earliest and most ferocious supporters. Some have compared to relationship at its closest between Kalanick and Gurley to that of former being Vito Corleone and the latter being Tom Hagen. Unlike that semi-familial relationship, however, things turn sour and Gurley is identified as being the prime mover in Kalanick’s eventual fall from grace.
Tim Cook
The facts are these: Uber could never have happened in a world without smartphones. And for a brief time before everyone in the world owned a smartphone, only Apple iPhone owners enjoyed bragging rights. The dependence upon smartphones as part of Uber’s business model foundation at a time when Tim Cook was literally taking ownership from Steve Jobs as the face of Apple is just one of the weird coincidences that conspired to allow Uber to enjoy success not because of but in spite of its founders.
Arianna Huffington
You hear a lot of inspiring Horatio Alger-type stories about billionaires who started out in their garage, but the truth behind almost every one of those stories—if not literally every single one—is that it takes a coincidence like Kalanick meeting the rich and famous and influential Arianna Huffington at a tech conference in 2012 for even the most brilliant idea to ever actually produce billions. (And only on paper, at that.) Huffington is the Greek-born woman who married and divorced a Republican politician before founding the mostly-liberal Huffington Post on her way to routinely making lists of the most powerful women in the world. When you have friends like Huffington and Oscar-nominated actor Edward Norton believing enough in your "crazy" idea to pump money into it, it wouldn’t matter whether you started in a penthouse, garage or abandoned sewer pipe.
