In dark jacket, grey sweater and white undershirt, Travis Kalanick was relaxed in comfy chair, coffee mug before him, shooting the breeze with late-night TV host Stephen Colbert. Then came a cry from the studio audience.
“Shame! Respect drivers’ labour! Respect professional full-time work!” The camera picked out a T-shirt-wearing protester who, standing and cupping his hands to his mouth, yelled: “Uber exploits taxi drivers for profit and kills professional full-time work in the taxi industry!”
Colbert asked the man to sit down and joked to Uber co-founder Kalanick: “That’s my cousin. I apologise.”
This September 2015 incident – a rare moment when a king of the gig economy was confronted by one his powerless subjects – was not broadcast at the time, but finally aired on CBS last month, when Colbert interviewed actor Joseph Gordon-Levitt about playing Kalanick on the small screen.
Super Pumped: the Battle for Uber is the story of how Kalanick led the fastest-growing startup in history, taking on incumbent taxi industries in San Francisco, America and the world. It is a compelling portrayal of a man who is in turns charming and obnoxious, genius and crazy, superhero and supervillain, and who gives new meaning to the word “disrupter”.
It is also a glimpse of a tech industry where there is a thin line between creation and destruction and bad boys such as Facebook’s Mark Zuckerberg, Tesla’s Elon Musk and Twitter’s Jack Dorsey are criticised for moving fast and breaking things with little regard for who gets hurt.
Beth Schacter, an executive producer of Super Pumped, told a recent Washington Post Live event: “They’re kind of modern kings, and in that Shakespearean way of wanting to examine what makes a king and what brings a king down, it’s kind of where many of the kings are, either in the high finance area or in Silicon Valley.”
Kalanick’s rise and fall was certainly Shakespearean. Born in Los Angeles in 1976, he learned to computer code at school and dropped out of university to start his first tech company when he was 22.
He co-founded Uber in 2009, launching its first smartphone app, UberCab, the following year – a revolutionary idea for passengers to hail and pay for taxis on their phones and for drivers to work when they wanted. The first episode of Super Pumped finds Kalanick acknowledging that the original concept came from friend Garrett Camp, making his pitch to venture capitalist Bill Gurley (Kyle Chandler) and defying San Francisco city bureaucrats who want to crush him.
With Gurley’s financial backing and mentorship. Kalanick embarked on a rule-breaking, self-mythologising global conquest that saw bitter battles with entrenched interests that helped drag transport into the 21st century (“We are in the world changing business,” says the screen version of Kalanick. “At least, I am.”)
By 2017 the company had grown to an international operation with a market value of nearly $70bn. But in February that year a blogpost by former employee Susan Fowler blew the whistle on sexism and “bro culture” at the company, and in May, Kalanick was devastated by the death of his mother, Bonnie, 71, in a boating accident.
By June, Kalanick’s wild ride at Uber came to an end when he was forced to resign over a series of lawsuits against the company over workplace discrimination and sexual harassment. It was at last a reckoning over years of poor treatment of workers and the dangerous conceit that high performers went unpunished.
In short, Super Pumped has a lot of material to work with. It does so with slickly produced, tightly scripted, crisply acted relish (Uma Thurman plays Arianna Huffington, the co-founder of the Huffington Post, who was an Uber board member).
The series is made for Showtime by the team behind Billions. Its primary source material is a bestselling non-fiction book of the same name by Mike Isaac, a New York Times technology correspondent who served a consultant, factchecker and co-executive producer. He has met Kalanick on numerous occasions, though the entrepreneur did not want to participate in the book.
Isaac says by phone from Oakland, California: “He’s a very charismatic person. You might not immediately vibe with the guy because he’s a little more masculine than, let’s say, other folks that you want to hang out, with but he’s very sharp, very intense, very driven, willing to argue his points, but he can also charm you.
“The last time I talked to him was right before he went to testify in court in the Google/Waymo trial, and he was still very magnetic. People flock to him in a certain way and he has the charisma, which is an important quality to have if you’re going to be leading the company.”
Asked if he likes Kalanick personally, Isaac admits to having mixed feelings. “On the one hand, I try to see the whole person, and there’s more depth to him than you would have carried away if you were just reading the headlines a few years ago.
“That said, you can’t divorce the person from the sort of things they cause in their life. Under him, Uber became a really dysfunctional place for a lot of people to work. Some people might say he created this new labour model that I know a lot of folks are upset exists.
“So I don’t think he’s a cartoonish villain; I don’t think he’s a complete angel. He, like all of us, exists somewhere in the middle. He has redeeming qualities as well as things that he probably has to answer for at some point.”
Gordon-Levitt, widely seen as a Hollywood nice guy, is cast against type to great effect. At some moments the viewer sees his vulnerability and complex family relationships and roots for him to succeed; at others, we wince at his gigantic ego and callous treatment of drivers and passengers as commodities.
After the first episode was broadcast, Isaac received text messages from sources saying the actor nailed Kalanick perfectly. “Travis is a ruthless person, very driven; megalomaniac is probably a good way to describe him.
“But I also think that you wouldn’t understand that he has nuance to him if you were just reading the headlines from 2017. So I saw them bringing in Joe as someone who could bring depth to the character and round him out in a way that’s not one-dimensional was really important.”
Gordon-Levitt’s performance renders Kalanick as a swashbuckling, visionary businessman facing down opponents through sheer force of will; but also as the boss from hell willing to belittle and insult his employees without pity.
Isaac adds: “He was very good at explaining the math and theory behind why it all worked out, but lacked a kind of empathy for the people directly involved a lot of the time.
“It’s one of these things where he’s a brilliant guy and lives in a sort of fantastical world of how things should be, but isn’t able to connect on an emotional level to someone who’s struggling, or be able to empathise in the moment with someone who’s going through a hard time.”
At one point in the series, Gurley observes: “The best thing about Travis is he’ll run through walls to win. The worst thing about him is he thinks everything’s a wall.” Like a politician who is great at campaigning but terrible at governing, the qualities in Kalanick that helped Uber rise proved useless once it reached the top. In fact, they planted seeds of self-destruction.
Isaac says: “The problem with Travis is that he always felt like he was an underdog and fighting and in one mode, and that’s good while you’re coming up. But Uber eventually won, it became ubiquitous and it destroyed the taxi industry, and he wasn’t able to change out of that fighting mode into a normal, ‘OK, we can be peaceful and operate in cities without having to fight everyone.’
“Maybe there’s a different version of history if he would have been able to grasp that it’s kind of a tragedy because he wasn’t able to see it until it was too late.”
A similar ambivalence hovers over the legacy of Uber, Lyft and other apps that some regard as avatars of progress, much as the motor car rendered the horse and carriage obsolete, and others say are new weapons of capitalist exploitation. The gig economy is worth more than $5tn a year worldwide and was accelerated further by the pandemic but offers little by way of trade unions or safety net.
Isaac reflects: “A lot of folks ask would Uber be Uber if it weren’t for Travis? Can you will a sector like this into being when the folks who are entrenched in the first place aren’t going to let you play ball? Is there a nicer version of Uber that could have come into being?
“There are a lot of amazing things that the company has done just in providing transport for folks who maybe were too scared to get home when they get off work at two in the morning and don’t want to wait for the bus. I know a lot of folks who have to do that sort of terrible commute and feel safer doing an Uber.
“But then there are also the folks who feel that they’re exploiting workers, and [that] this model might not be good for workers in the long run. Like many different kinds of new innovations in the world, it brings with it a host of issues. Like anything with Uber, it’s never easy or straightforward.”
Today, Uber has around 118 million monthly active users around the world while Kalanick is still a billionaire and running a property development company. Super Pumped is a new take on an old question: can you be a nice guy chief executive and still make world changing things happen?
Isaac comments: “For really big swings and big moonshot ideas, you kind of have to be a little … if not crazy, then at least an eternal optimist. It takes a lot to believe in this mission.
“That’s why you get these larger-than-life personalities. I don’t think it’s an accident that they tend to go hand-in-hand.”
Another perspective is offered by journalist Brad Stone, author of The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World, who has interviewed and dined with Kalanick.
He says by phone: “He was confident to the point of maybe arrogance, but a lot of entrepreneurs are. There was a lot of swagger and there had to be because they were trying to change a pretty big industry.
“The whole thing was put on steroids. Suddenly, the speed at which they went from a small startup in San Francisco and Washington trying to fight regulators to being valued at $50bn and having thousands of employees, the wheels came off.”
Stone adds: “At a certain point they just got besieged by not only their success but the culmination of all the mistakes and the problems with growing that fast – and the fact that his confidence did turn into hubris.”