Inside The World Of San Francisco’s Millionaire Uber Drivers
"My privilege is probably showing right now, but turns out fuck you money is overrated."
David — at least, that’s what the app said his name was — is no regular Uber driver. Instead of driving a Honda Civic or any regular car, he drives a black Tesla as he picks up passengers around the city. He’s 20-something years old, wears a tech t-shirt and Ray-Bans, and he’s super rich. David is a member of a new, strange, but increasingly common demographic: the millionaire Uber drivers of San Francisco. Halting Problem was able to arrange an interview with David as he facilitated our morning commute to work.
Halting Problem: I like the Tesla. What’s the story behind it?
David: Coming out of college, I cofounded a startup called Rivalta that sold to Salesforce. I stayed around long enough to vest, and then I bounced. It was a good exit: I bought the Tesla a year later because I thought it was a cool car.
How do passengers react to the Tesla?
People are pretty shocked. Like, “Nice, a Tesla! I’ve never been in one!” or, “Why are you driving randos around in such a nice car?” I feel like most people get into Ubers and want their drivers to shut up and drive them where they need to go. But with the car, people are more curious about who I am and where I come from, so it’s definitely a conversation starter.
I used to turn on the autopilot during rides and let the car drive itself, but some of the passengers would freak out when I took my hands off the wheel and started Snapchatting my friends. Can’t lose that five star rating.
How did you get into driving for Uber? Why are you still working?
When I was working on Rivalta, I got 2 hours of sleep a night because I was working so damn hard. So when we got bought by Salesforce, I was like, “Great! I hit the jackpot!” Then I rested and vested at Salesforce until I was sick of it, and I thought I’d take a break and chill out for a while, so I left.
I spent a few months travelling around, then I came back to SF. At that point, I felt like that guy from Office Space. “If I had a million dollars… I’d do nothing. I’d just relax, sit on my ass, and do nothing.” Turns out if you do that, it’s actually super boring. I stayed in bed and browsed reddit all day. Like, all my friends were at work during the day so they couldn’t hang out, so I had nothing to do. I told my cofounder how bored I was and she said, “Why not drive for Uber?” So here I am.
Wow. That’s like prestige mode in Call of Duty. You reached level 100, successful entrepreneur with fuck you money, and you went back to level 1, bottom of the totem pole, as a 1099.
My privilege is probably showing right now, but turns out fuck you money is overrated. For years, all I thought about was Rivalta. All the time. I’d be at a bar or at a party and I’d be thinking about new ways to growth hack our service so I’d land a great exit and have fuck you money. Then I did that, I left my job, and the thing that I had spent so much time and effort on just disappeared from my life.
Why did you start driving for Uber instead of, say, becoming a Taskrabbit?
There’s not much that’s shared about other sharing economy jobs. You’re usually alone all day, and you’re doing boring menial stuff. Since I had my choice of shit jobs, I figured driving around would be a lot more pleasant than cleaning people’s houses, and I was right. It’s a really chill job, I get to explore the Bay Area, and I get to meet interesting people. It never gets old to see people’s reactions when their UberPool pulls up in a Tesla.
Are there a lot of millionaire Uber drivers?
Kind of. The startup community is pretty tight, so we know each other. We actually have a Facebook group called “Techie 1099s.” Most people in the group are founders who exited and drive Uber or Lyft for fun. There’s one guy who founded a pretty successful company and still works there, but he bikes for Postmates after work just to get some exercise. Instead of paying for a gym membership, he gets paid to bike up and down the hills in SF.
Have you gotten any negative reactions to being an Uber driver?
One passenger said that we [millionaires] were taking business away from people who actually need to drive Uber to make a living. I think that’s a bit silly. There’s only a hundred or so of us, and that number’s probably going to go down given the performance of tech stocks recently.
So what’s next for you? Are you going to drive for Uber forever?
Definitely not. I’ve been thinking of doing another startup. I actually picked up a VC while I was driving around Sand Hill Road and pitched her, so maybe I can tell people in the future that I raised a seed round by driving for Uber.
Oh wow. What was that conversation like?
It was pretty interesting. We talked about wearables. Apparently you can buy a wearable that shocks you whenever you go on Facebook, so you’re conditioned to be more productive. She put $1000 into the Indiegogo for shits. Now I think about it, a cushy VC gig would also be nice as a next job.
Alright, this is my stop. Any final words for our readers?
If you order a burrito through Postmates and a guy named John delivers it to you, ask him to give you a tip.