Vomit, guns, and sexual harassment: A Minnesota driver shares his wild Uber tales

Images courtesy the author

Images courtesy the author

When Evan Kail signed up to be a rideshare driver for Lyft and Uber, he had no idea what he was getting into.

At the time, Kail was a screenwriter with an L.A. agent, and he was on the verge of breaking into the industry. He needed a job that would allow him downtime to work on his scripts. He’d read that Lyft and Uber drivers made decent money and the online ads made driving for those companies look like fun. So he traded in his old BMW Z3 for a new BMW 528 and signed up with both services.

Ubered is the story of his bizarre experiences as a rideshare driver. The stories come from a journal Kail kept of his rides. To make the book more interesting, he invented rules, such as: “If a rider invites me in after the ride, I have to say yes.”

“That got a little weird,” he admits. One man invited him into his home…to introduce Kail to his massive gun collection. He even aimed a shotgun at Kail. “He was just showing me, ‘Hey, check this out,’” Kail says. “But it was definitely very dangerous.”

He eventually gave up on that rule, but riders continued to surprise Kail. Once, a college-aged rider punched a guy, fought off the guy’s friends, jumped in Kail’s car, and yelled, “Go, go, go!” Fearful of the mob, Kail sped down the block, pulled over, and told the guy to get out. “He gets in my space, like he was about to fight me, and I go, ‘Sweetheart, I have your credit card information. Get the eff out.’ As soon as I said that, he was out of the car.”

There was also an incident with a touring band, detailed in full in the book. According to Kail, the band’s drummer was trying to get with a fan after a concert, and followed her into Kail’s car. He invited her to his hotel room, but she let him have it.

“This is before the #metoo thing, but everything you can imagine about the #metoo movement is what this woman was saying to this guy. And he was just jaw to his lap when she was done,” Kail recalls. “He gets out of the car and slams the door so hard I thought he was going to break the window. He goes storming into the hotel. I’ve never seen a grown man have a temper tantrum like this.”

Kail himself was sexually harassed “like you wouldn’t believe” on the job. People offered him sex (paid and unpaid), touched him, and tracked him down on Facebook after rides.

It wasn’t all awful, however. Kail admits rideshare driving is a fun, adventurous job. “Cruising around Minneapolis in a BMW at three o’clock in the morning; that’s pretty cool,” he says.

A good or a bad ride often depended on whether he was driving for the day crowd or the night crowd.

“The later it gets, the higher the odds of something weird happening,” he says. The day crowd was primarily tame – though there were exceptions. He once picked up a guy at Stanley’s Bar at 2 p.m. on Tuesday. “This guy is one of the most destructive alcoholics I’ve ever seen in my life,” Kail says. “He’s completely shit-faced and he keeps handing me money to take him to new bars. At one point he comes running out – I’m sitting there waiting because he’s paying me money – and he goes, ‘Let’s get the fuck out of here! The cops are coming! I got into a fight with the bartender.’ There were colorful incidents during the day.”

Another occupational hazard: vomit. Kail jokes of “Bile for Benjamins: the unofficial Evan Kail charity fund,” because drivers receive $150 if someone pukes. On slow nights, he would pick people up knowing they would soil his car just to get the payout. “Puke doesn’t bother me because I was in a fraternity in college,” he explains.

Why does he stay in such a volatile work environment? He attributes his perseverance to a kind of Stockholm Syndrome. “Even though this is a terrible, highly oppressive system that I’m a part of and it’s chewing me up and spitting me out, I keep going back to it like a moth to a flame,” he says. “As far as making money goes, it sucks. There’s better ways to do it.”

Along the way, Kail learned a bit about humanity, too: People are predictable and drinking makes everyone an idiot.

Overall, though, this gritty side-hustle has been life-altering for Kail. “The screenwriting thing, forget it,” he says. “I’m into writing books now. I’ve completely pivoted in ambition.”

Kail plans to release an Ubered sequel this summer, and is finishing a novel. Miraculously, Uber either doesn’t know or doesn’t care that its dirty little secrets have made their way to the printed page.

“Somehow, my account is still active,” Kail says. “I don’t know how much longer that’s going to continue. All Uber has to do is read the book and they can see that they should have probably fired me a while ago.”


Evan Kail, Ubered
Magers & Quinn
7 p.m. Tuesday June 5