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Inside the Uber Side Hustle

For many ridesharing drivers, getting behind the wheel is just a way to market their real ambitions

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

In March of last year, Jonathan Gaurano was in a dark place. A fallout with his business partner left him broke and without a job, all while he was dealing with a recent breakup. The 28-year-old UC Berkeley graduate was unsure what he wanted to do with his life. So he began driving for Uber.

“I was in a weird funk,” said Gaurano, who began driving 10 hours a day for the ridesharing service. “Those things really propelled me just to say: ‘Time to live in my car.’”

But it wasn’t long until Gaurano’s entrepreneurial mind took hold, and he began to strategize how to get the most out of his trips across the Bay Area and his occasional trips to L.A. In his past job, he managed and filmed YouTube stars. So naturally he began plotting the makings of a viral video. When he came up with the idea of rideshare karaoke, Gaurano bought a camera and a GorillaPod, attached the setup to the dashboard of his silver 2014 Nissan Versa, and started asking his passengers to sing along to music.

And viral he went. When he posted a supercut of himself and his passengers karaoking to the Weeknd’s “Can’t Feel My Face” mid-route, it appeared on the front page of Reddit. Two weeks after that, he got a call from the Weeknd’s management: They wanted to fly him out to Toronto to see a concert and meet Abel Tesfaye himself. He asked Tesfaye what he thought of the video.

“He said it was ‘fucking genius,’” Gaurano told me.

More important than the Weeknd’s kudos, though, was the media attention from sites like the Daily Mail and E! News, which earned Gaurano more than 1 million views on YouTube. Less than six months into his time as an Uber driver, he’d found a way to parlay his driving gig into the beginnings of a veritable side hustle.

Gaurano is part of an emerging group of rideshare drivers who — much like a parent driving a teen to school, or a performer in a subway train — have begun to capitalize on their captive audiences. Whether fledgling YouTubers, musicians, artisans, farmers, business owners, or comedians, many contractors of the app economy now use their time on the road to boost their business or craft. What was once a vehicle for creative types to supplement their income is slowly becoming its own stage for industrious performers and salespeople. And in most cases, the underlying goal is the same: to escape the confines of their rideshare job for good. Or, as Gaurano put it to me: “If I’m still doing this next year as a full-time job, I’m going to be honest: I failed myself as a content creator.”

While this story was being reported, Uber became tied up in the controversy over President Trump’s executive order temporarily banning refugees and blocking travel from seven majority-Muslim countries. Some Uber drivers, including Gaurano, quit driving for the company via public announcements.

“I used Uber’s popular brand name to create viral online videos where I’ve been known to do fun things in my car with my riders,” he wrote in a widely shared post that was picked up by TMZ. “But, making a strong stance is something that needs to be done.” His loyalties — and viral video backdrops — now lie with other ridesharing services like Lyft or Juno. While many might see Gaurano’s reason for leaving Uber as legitimate, his Facebook post could also read like another opportunity to garner a little promotional attention.

But could you blame him? As the ridesharing economy has ballooned over the past several years, so have tales of the strain it puts on workers. Drivers are submitted to grueling schedules that sometimes include the use of a “pee jar” or, as Bloomberg recently reported, a night’s sleep in an empty parking lot. Because driving for a mega-contractor can be exhausting, many people sign up for Uber or Lyft with the idea that it will be temporary. According to Harry Campbell, who occasionally drives for Uber and Lyft but has transitioned into running a blog called The Rideshare Guy, it’s common for new drivers to see these jobs as a means to an end, rather than a career path.

“If you are a young, single guy or single girl, you can share a room,” he said. “Your expenses are very low; you only need to make a few hundred bucks a month. You can make that on Uber and then pursue whatever it is you’re passionate about.”

Campbell says that because of both the flexibility of ridesharing apps and the instant connection they create between customers and drivers, he’s encountered more and more drivers pitching their entrepreneurial pursuits during rides. Sometimes it might be something subtle, like laying out handmade jewelry on their seats or handing out business cards. But he’s also come across part-time insurance salesmen, startup founders looking for investors, and even a farmer from North Carolina who drove in the offseason.

“He sold tomatoes out of the back of his car to his passengers,” Campbell said. “It wasn’t strictly to grow his business. It just fit in so nicely with his schedule.”

Some rideshare hustles are less wholesome. Of the many anecdotes passed along to me, there was a driver who attempted to rope his passenger into what appeared to be a life-insurance pyramid scheme, another driver who sold packets of weight-loss coffee powder out of his trunk, and yet another who pitched a self-produced TV pilot about “the early 2000s.” I still have the business card of a Juno driver who tried to persuade me to hire him as a life coach. (I declined.)

But in the age of James Corden’s wildly popular “Carpool Karaoke” clips, live musical performances like Gaurano’s are the most popular ridesharing extracurricular. Take 23-year-old Daynel Artiles, who calls himself “the singing Uber driver.” Artiles started driving for Uber in May when he was discharged from the military because of an injury and needed to find a job that didn’t require too much activity. As he began chauffeuring passengers around Miami for eight hours each day, it dawned on him that he could both make money driving and pursue his longtime passion for music. That’s when he decided he would sing to his passengers and ask them to post his performances on social media to spread the word using the hashtag #SingingUberDriver.

Before he dove into his new dual persona, however, Artiles devised a strategy that’s common among the enterprising drivers who want to avoid seeming overly self-promotional: a short script. He’d kick off a conversation by asking about his passenger’s day, a question they would typically reciprocate. From there Artiles would bring up his goal to “make money and get famous in the process.” Their curiosity piqued, the passengers would ask why.

“That’s when I tell them, ‘Oh, I’m a singing Uber driver and I sing to my passengers,’” he told me. “Once I say that, they automatically want me to sing for them.”

According to Artiles, the strategy has worked. He says that even the most skeptical clients are won over when they hear his voice — aside from a few who were too inebriated to appreciate the show. He typically sticks to hits by Michael Jackson, Justin Bieber, and the Weeknd. And though mimicking these musicians has helped improve his self-taught singing, driving while also attempting to hit the King of Pop’s high notes has proved difficult.

“It’s hard to sing in a car, because you’re sitting down and you can’t breathe really properly, and so the notes that I hit inside a car are not the same notes that I hit when I’m standing in good posture,” he said. (Nevertheless, he plans to continue to release his own music and promote it through Uber.)

BJ Griffin, a cellist and lead singer for a band named BJ Griffin and the Galaxy Groove, says that aside from making his driving shifts more fulfilling, singing for his customers gives him an extra bump in exposure. Since he began driving for Uber in early January, the Virginia Beach, Virginia-based musician has spotted his passengers in the audience at his local shows. One client even began taking guitar lessons at his music school, Galaxy music.

“It’s tough to really promote yourself and get your name out there,” Griffin said. “[We] entrepreneurs have to come up with new ways in this day and age where everything is so fast. I thought this singing Uber experience would be like, the next thing that people — musicians in particular — can do to promote themselves. And make a little money on the side? Awesome.”

Griffin, a self-proclaimed “young Stevie Wonder,” is careful to read the mood of his passengers before offering to serenade them. In some cases, he will forgo a joint karaoke session with his passenger and instead match his music to their mood.

“There’s some people who just want to get to where they’re going as quickly as possible, and I respect that,” he said. “At that point I just customize the music experience with my vast library of songs.”

Gaurano estimates that only 10 percent of his passengers accept his invitation to do karaoke — but that’s partly because he’s picky about who he wants to “cast” in his videos these days. In the past year, the Chainsmokers hired him to film a rideshare karaoke video for their song “Roses” and he partnered with local animal shelters to hand out puppies to his passengers. He now regularly integrates props like hats and instruments into his in-car shoots. His work thus far has landed him a side gig growing Facebook, Instagram, and YouTube feeds for “influencers.” While he’s no longer driving for Uber, Gaurano is still driving for other rideshare services and looking for new ways to get noticed — and eventually graduate to something different.

“I don’t want to be one of those normal Uber drivers who always brag about all the other side things that they’re doing in their life,” he told me before he quit in protest. “Like, ‘I’m not really an Uber driver, I’m also this, this and this and this.’ I think the reason why they do that is because it can be a little bit embarrassing to go to a party and say, ‘I’m an Uber driver.’ I’m very much in that camp.”