Ambitious Baller Syndrome
What Travis Kalanick can teach us about billionaires breaking bad
I started to watch the show Super Pumped when it came out but never got into it. Now, having read the book by Mike Isaac, I realize why it was hard to make a TV show. The Travis Kalanick story doesn’t lend itself to the sort of scene-chewing that Jared Leto was able to do as Adam Neumann in We Crashed, the saga of WeWork’s rise and fall. Kalanick, the former CEO of Uber, wasn’t trying to be a messiah or a guru. He’s a grinder, a founder who fails, falls down, and comes at you ten times harder.
The story of Uber’s Kalanick years is not dissimilar to any other platform tech company driven by a young founder with a bit of a reputation for being ruthless, smart, and tremendously tuned toward taking risks. As Isaac says in the book, for “every Wired cover story of a boy genius striking it rich with a smartphone app, there was a mess of secondary effects left in his wake.”
Silicon Valley has fostered the mythology of the boy king. Venture capitalists have been trained to seek not the product, but the person. The confident asshole, usually male, who will persist, who will stride onto the battlefield like a colossus with one goal, to take an enormous amount of market share. It isn’t about the money at that point, get the market, and the money will come, or at least it will happen often enough and dramatically enough to make all of the failures worth it.
But something happens when these young founders get to a certain point. They shift. Somehow the money changes them. In Super Pumped, Issac calls it ambitious baller syndrome, chronicling the decadence, the predatory behavior against women in the nature of a good time, the endless cycle of yachts, night clubs, and celebrities. It’s banal in its repetitiveness. People ascend to wealth beyond imagination and they mostly all go for the same things, the private jets, the restaurants, the designer things. It’s as if there’s a billionaire playbook with all the same items.
It doesn’t always happen when founders are young, sometimes they make it to their forties or fifties before it hits, but it nearly always does. The three-comma club has a way of changing people. Founders are often different than CEOs because they have so much say over their own companies that they forget that there is any division between who they are and the company itself. The public does the same. That’s great when it’s going well, but when a founder starts to flame out, he can take a company with him.
That was almost the case for Uber, and why Kalanick was unceremoniously removed. In his place, Dara Khosrowshahi steered the company through its stock market debut and the pandemic with a steady hand on the wheel. Steady can be good, Uber’s stock has risen steadily since its IPO although it hasn’t blown the doors off. Khosrowshahi has kept the company focused on what it does best and led the company to a solid profit in 2024, no easy feat for a company that was burning money under Kalanick. Would it have become a better company under Kalanick? Would it have expanded more rapidly or would the fault lines under his feet have widened into caverns, it’s impossible to say.
Kalanick, for his part, has been quietly building his cloud kitchen empire, running in well-funded stealth mode for over eight years. The food prep and delivery area has a lot of competition and he doesn’t have a first mover advantage here but it’s hard to count him out. The move may be toward robotics-driven food prep, something that has been implemented in some places but hasn’t fully taken off yet.
The impact of Uber has been profound. Teens don’t rush to get their driver’s licenses as fast as possible, knowing that they can get everywhere they need to be as long as someone pays for it. It has changed going out at night for the better. I’m old (and old school) so I still drive (most of the time), and I like to cook, but I’m watching a new generation that prefers to skip the daily aspect of these tasks and reserve their efforts for special occasions.
As for the billionaire founders, one thing remains clear, they can’t turn off the impulse that got them there. They may visit a tropical island but they don’t fade off into a Caribbean sunset. Instead, they keep striving or hustling, to use Kalanick’s term. If there’s anything positive about AI it may be that it will mean that fewer employees will be ground to dust following demands that only a founder or a robot could keep up with.