“My next guest is the co-founder and CEO of ride-hailing app Uber,” Stephen Colbert said on one of the first episodes of his Late Show before taking a beat to tap on his smartphone. “And he’ll be here in 10 seconds.”
Indeed, by September 2015, the 5-year-old private transportation company had become so pervasive in American culture that its CEO was granted a prime seat at the relaunch of a marquee late-night franchise. There was Travis Kalanick, booked for airtime alongside Vice President Joe Biden, with actresses Scarlett Johansson and Amy Schumer as well as rapper Kendrick Lamar among the premiere-week guests.
The visit was part of a big year for Kalanick, one that found his company becoming the most valuable privately held startup in the world, exploding domestically and across the globe (especially China and India), cementing its status as the go-to ride-sharing app on planet Earth and endeavoring to blow apart what it sees as overly stifling regulatory problems. It might not have always been the smoothest of rides, but the numbers tell quite a story.
In July the company closed a funding round that valued it at more than $50 billion. Only two venture capital-backed startups have passed that level of valuation, and the other was Facebook, which took nearly seven years to do it, compared with Uber’s five. Also last spring, the 39-year-old made Forbes’ list of the world’s billionaires with a net worth of $5.38 billion; that amount has since grown to $6 billion. Uber has 1.1 million active “driver-partners” (those who’ve driven at least four trips in the past month), and 400,000 of them are in the U.S. It has 4,800 full-time employees worldwide (five years ago that number was 300), and as of mid-November, it was operating in 356 cities in 64 countries across six continents.
Even by Silicon Valley standards, it’s been a pretty shocking rise. Kalanick grew up in the Los Angeles suburb of Northridge; by some reports, he’s been coding since the sixth grade. In the late ’90s, he dropped out of the University of California, Los Angeles (UCLA) to launch the music file-sharing service Scour, a bit of a tricky proposition then, and Scour was eventually sued for $250 billion, forcing the company into bankruptcy. From there he founded Redswoosh, a file-sharing company that he sold to Akamai for a package that included $19 million in stock, plus other compensation.
With more than a few dollars in his pocket, Kalanick commenced traveling the world, which continued until one snowy night at the LeWeb conference in Paris. As the myth goes, Kalanick and Uber co-founder Garrett Camp were standing outside waiting for a cab. Cold and annoyed, Camp wondered aloud why he couldn’t just take out his phone, push a button and fetch a dry ride home. Eighteen months later, in the summer of 2010, Uber launched in San Francisco with a small fleet of cars, seed money and 100 friends. “Garrett brought the classy,” Kalanick said in a five-year anniversary address to employees in June, “and I helped to bring the efficiency.”
“In many cases [doing something new] means going up against powerful incumbents that will do whatever it takes to keep your idea down.”
By now Uber’s benefits are well-recited: Drivers use their own cars. They make their own hours, and their shifts are 100 percent self-directed. “People decide where, when and for how long to drive,” he wrote in the Pacific Standard’s “Future of Work” project in October. “They are free to turn off the app and stop working at any moment. In other words, their needs determine their work schedule—and nothing else.” Nearly 90 percent of drivers, he says, cite the flexible schedule as a major reason they work with Uber.
Kalanick and his company faced unprecedented scrutiny and their fair share of obstacles in 2015, including controversies about surge pricing (the practice of increasing rates during busy times), driver and passenger safety, and continued protected battles against regulatory groups. (It also faced off with New York Mayor Bill de Blasio in the summer over the number of cars on city streets.) Several of those battles saw Kalanick participating directly; he’s known as much for his success as he is for his spirited defenses of himself and his company.
“In many cases,” he told UCLA students during a visit in October, “[doing something new] means going up against powerful incumbents that will do whatever it takes to keep your idea down—but in any case, it means going against the crowd—against what everyone else is doing. This requires an infallible belief in your idea, your principles and your ability to withstand the pressure to go with the crowd, and instead determinedly seek the truth regardless of where it leads.”
Kalanick spent a good bit of 2015 working to mentor would-be game changers like himself. In addition to stops at events like UCLA’s, where he privately mentored students and young alumni, he was active with the educational organization Girls Who Code, whose members pitched him ideas for new apps in September. In November he spoke at Summit at Sea alongside former Google CEO Eric Schmidt; before departing he spoke to South Florida community college students about being an entrepreneur and how they could capitalize on their ideas.
He has more ideas of his own: Uber is said to be investing $1 billion in its Indian market and another billion in China. The company is part of the discussion about driverless cars, as you might expect. The carpool-based service UberPOOL marked its first birthday in San Francisco in August and has since expanded to include Paris, New York, Los Angeles, Boston and Austin, Texas. The bike-courier service UberRUSH has opened in New York, Chicago and San Francisco; instead of delivering passengers a car, it delivers businesses… well, pretty much anything.
And on Colbert, Kalanick touted something even closer to people’s hearts than convenient rides home: UberEATS, a lunch-delivery service (currently operating in select cities) that’s geared to small restaurants; the kitchens make the food, deposit it into temperature-controlled packaging and then it’s delivered.
He’s not just gunning for your car—he wants it all.
Read more 2015 SUCCESS Achievers of the Year stories:
This article appears in the February 2016 issue of SUCCESS magazine.
Jeff Vrabel is a freelance writer whose work has appeared in such publications as GQ, Men's Health, Time, Billboard and the official Bruce Springsteen site, because though he's had many bosses, there is only one boss. He lives in Indianapolis with his wife and two sons—the older just stole bacon off your plate and the younger was personally approved by Springsteen (long story). He can be reached at the cleverly named JeffVrabel.com.