Confessions of a Milwaukee Uber Driver

Uber has been called many things. One driver, returning to ferrying passengers decades after his stint as a Milwaukee cabbie calls the new ride-sharing service something else: a cure for loneliness.

My evening starts Downtown.

The passenger, a woman in her 40s, works in an office building and is headed to an address in a working-class neighborhood on the North Side. This is her first experience with Uber – her daughter usually picks her up, but can’t today – so I have to explain how it works: Uber will charge your credit card, and after I drop you off, you’ll get an email telling you the cost.

It’s Friday evening, about 5 p.m., but the woman doesn’t seem to be relieved or excited that the weekend is here. On the ride out Fond du Lac Avenue, I get a hint of why: She’s talking in my back seat on her phone, trying to sort out a drama involving a relative, some missing money and some people “you don’t want to mess with.” Seems she had to leave work early to deal with the situation. “I’m done with this,” she says a couple of times. But she’s still on the phone when I drop her off.

My next passenger is a young woman I pick up at a Head Start school on North Teutonia Avenue. Long black hair, with a bit of a North Side accent. I’ve got NPR on the radio, with somebody talking about Irish comfort food, and I ask her if she wants music, and if so what kind. Almost as if she’s sharing a secret, she tells me to turn it to 103.7. It’s KISS-FM: All that reveals is that she is young, which I already can see. On the way west on Silver Spring Drive to her apartment, we pass Growing Power headquarters, and I tell her about its founder, Will Allen, the national leader in urban farming who teaches kids how to grow vegetables. She hasn’t heard of him, but she’s interested. “It’s good they have a role model,” she says.

Next is Bridget, 40s, with a pleasant, round face, glasses and curly hair. I pick her up at the Northwest Side social services agency where she works with at-risk youth. I ask her how long she’s been using Uber. “About two months,” she says, “since my daughter got her driver’s license and I found out we were sharing my car.” But she’s speaking with affection, not complaining. Her daughter’s a junior at High School of the Arts, she says, majoring in dance. They’re just getting ready to start the search for a college with a good dance program. The girl’s going to do well, her mother says – she’s mature for her age, self-directed. “You must be doing something right,” I say, and then I share a little bit of the pride I feel for my own son.

What I like about driving for Uber is that you get the chance to see briefly into so many people’s lives, and sometimes, to connect with them, even if only for 10 minutes.

I started driving for the ride-hailing service in October, when my severance checks from 24 years at the Journal Sentinel were about to run out. Ubering was not the most lucrative of jobs, but it had the advantage of allowing me to work whenever I felt like it, and it supplemented the part-time freelance editing and writing I was already doing. (It also took me back a bit to the cab-driving days of my youth, but more about that later.) Still, more than the money, driving for Uber helped fill a need I didn’t realize I had – for fellowship. Freelance writing and editing were a little lonely, after decades in a sociable newsroom. Not all my passengers feel like chatting – and I’m not always talkative, either. But with many of the people who climb into my Prius, a ride is a great way to become at least cursorily acquainted. And on a longer ride – say, to the airport – you can go a little deeper.

So it is this Friday night in mid-March. On a cruise down I-43 from Glendale, I get to know a 30-ish woman who, in contrast with my first passenger, is completely ready for the weekend. She’s an occupational therapist who now works in health care quality control, open and friendly, just back from a business trip to Michigan. She’s on the way down to the Potawatomi casino, where she’s meeting some girlfriends for Asian food and the singing performance of a guy they know. Then maybe a little gambling? Maybe, she allows. We talk about ethnic dining in Milwaukee – I’ve just finished editing this magazine’s April issue – and she says she grew up in a small Wisconsin town, and when she first arrived in Milwaukee, she didn’t want to try any unusual foods. The city has made her more adventurous, she says.

A couple of rides later, I become acquainted with Jared, a slim young MIAD student with a thin goatee and a big brown cowboy hat. He’s got a case of audio equipment and a backpack, and he’s headed first for the art school to pick up some headphones, and then up to G-Daddy’s BBC at Farwell and North avenues on the East Side, where he has a DJ gig. “Whenever I DJ, I go by the name Turtle Sooup,” he says. He’s a junior, majoring in “time-based media” (animation and video) at MIAD, and is working on a cartoon about a jock and a hipster joining a fraternity. He ran track at Rufus King High School – sprints, mostly – and when he graduates from art school, his ideal job would be working at a music magazine.

I could go on – for example, later I overhear a young woman in my back seat dissecting with a friend an exchange of texts with her boyfriend, and wondering if it indicated that they were finished (her friend’s verdict: Just a communication problem) – but let me switch lanes….

Passengers on the way to a Turner. Photo by Adam Ryan Morris.
Passengers on the way to a Turner. Photo by Adam Ryan Morris.

I first drove for Yellow Cab in Milwaukee more than 40 years ago, on a hiatus from grad school, when the Boynton family owned the company, and you had to tip the supervisors if you wanted a decent car to drive. Newcomers and drivers on the outs were put in old rattletrap taxis we called “buckets,” as in “I’m putting you on buckets tonight.”

I continued driving in between Milwaukee journalism jobs until sometime in the mid-1980s, long after the taxi company had become Yellow Cab Co-op and I was renting cabs by the week from individual owners/co-op members.

I never made much money driving back then. I think my biggest year was 1982, when I was a full-time cabbie and cleared somewhere in the mid-four-figures.

But I sure had fun. The cabs were radio dispatched in those days. The dispatcher would call out intersections near the rides – “Cap and Oak, Oak and Loc, Murray, Brady, Astor…” (Hopkins and Hampton was “Hoppity Hamp,” by the way.) You’d click on your mic and volunteer for an intersection near you – and the dispatcher would give you an address. Often the address was a tavern, and the dispatcher would add, “at the house of refreshment.” Or if it was a grocery store, he would say, “Don’t break the eggs,” an announcement that you were about to load six or eight bags into your trunk, drive the passenger about eight blocks home, unload the bags from the car and not get a tip. There was one driver who would let out a derisive wolf howl on his radio whenever somebody got a grocery load. I don’t believe the dispatchers ever figured out who the guy was.

All to say that in fall 2015, I thought I’d get back into the taxi game. So I paid $75 for a taxi driver’s license from the city, with the aim of working with Yellow again – but I signed up for Uber, too, just to keep up with the times. Once I started with Uber, I never got around to being a cabbie again.

Tom Tolan watches for his next passenger on a rainy night of driving in March. Photo by Adam Ryan Morris.
Tom Tolan watches for his next passenger on a rainy night of driving in March. Photo by Adam Ryan Morris.

Uber is huge. In December, the New York Times reported its valuation at about $62.5 billion, which the Times said made it the world’s most valuable private start-up. An Uber spokeswoman, Lauren Altmin, told me that as of that same month Uber was operating in 67 countries and more than 360 cities. It is known for being extremely aggressive entering new markets; taxicab companies do not like it. Its growth is based on an extremely clever app that allows its drivers – they’re called “partners,” and they’re independent operators – to use their own cars to transport riders. In Milwaukee, at least, the rates are in most cases lower than cab fares, except during so-called “surges” – periods of high demand and therefore high fares – but those ensure that passengers will always be able to get a quick ride if they’re willing to pay extra. The app also sends riders a photo of their driver and a description of his or her car, with license plate number, and it allows drivers and passengers to rate each other on a five-star system at the end of each ride.

Uber arrived in Milwaukee in early 2014 along with a similar service called Lyft. The Common Council passed a requirement for ride-sharing drivers to get city cab licenses (which require a police background check, with fingerprints) in July 2014 – several months after the apps were launched here without city approval. Then in 2015, the state Legislature passed a law outlawing local regulations and setting statewide standards for the services. Uber and Lyft clearly have been growing here ever since. Back in October, somebody in the local Uber office Downtown told me there were already 2,000 Uber drivers in the Milwaukee area. Altmin told me in March that there were more than 5,000 in Southeastern Wisconsin, though she added that a national survey of Uber drivers in late 2015 found half of them drove less than 10 hours a week. Milwaukee’s License Division figures show somewhere in the neighborhood of 2,000 licensed taxi drivers – though clearly some of those licenses (such as mine) are not being used, and some were issued to Uber drivers, who now don’t need them.

Whatever the numbers, with Uber growing in Milwaukee, the business for individual taxi drivers is shrinking drastically, I’ve been told by multiple cabbies. And many cab drivers feel the situation got worse in March, when the county started allowing Uber and Lyft to make pickups at General Mitchell Airport, on a trial basis. I can’t say I’m happy to be part of this equation, especially since cab-driving is a prime entry-level job in American cities. (My favorite episode of the old “Taxi” TV series back in the 1970s and ’80s was when the cabdrivers were brainstorming possible jobs for ’60s burnout Rev. Jim Ignatowski, played by Christopher Lloyd. What could a guy with no skills and no education possibly do, they asked each other. “Drive a cab,” they all answered.)


Demand surges on the North Shore. Photo by Adam Ryan Morris.
Demand surges on the North Shore. Photo by Adam Ryan Morris.

Still, right or wrong, Uber seems to be in Milwaukee to stay. And when I’m behind the wheel, the experience does feel much as it did when I was driving Yellow cabs all those years ago.

For instance, the driver’s seat of an Uber is every bit as good as that of a cab for observing your home city.

When I say this I’m thinking of all the immigrants who ride in my back seat. I don’t know if Milwaukee is more cosmopolitan than it was in the old days, but I certainly ferry around a lot of people who hail from other parts of the world. On one long drive to the airport I got to know an engineer who had emigrated from Indonesia, and we ended up in a conversation about Indonesian President Joko Widodo, about whom my son had written during an internship with CNN. I’ve had at least four different UWM students from Saudi Arabia in my car; also Ukrainians, Nigerians and an Asian Indian who grew up in Singapore and now attends Marquette University. A Middle Eastern woman and her visiting mother rode Downtown from Glendale in a snowstorm to check out The Shops at Grand Avenue. (They plugged into my car radio and played Arabic music all the way down I-43.) And one day I picked up a German history professor visiting Milwaukee to research the role of German immigrants in the early years of the U.S. brewing industry.

But at the same time we’re a world city, we’re still also an intimate one, as I discovered when my passenger at a barbershop on East Pittsburgh Avenue turned out to be David Tolan, my dad’s first cousin, and when two others turned out to be my son’s Shorewood High School classmates, going to their jobs as cooks at a Cathedral Square restaurant. One day I was working at home with my app turned on, and got a call to pick up my neighbors two doors down. And once I picked up a young lawyer from Quarles & Brady Downtown and told him my late father had been a partner there. “Small world,” he said. “Small town,” I replied.

There also are good days driving and bad ones, too, just as there were long ago.

But sometimes, when the lights are all turning green at just the right time, and one ride follows another in smooth succession, you can get into a rhythm, and you sort of merge into the city, and it’s like you’re just a thought zipping around Milwaukee’s big mind.

I like it when that happens.

Tom Tolan is the copy editor at Milwaukee Magazine.

Random thoughts on Uber driving

Photo by Adam Ryan Morris.
Photo by Adam Ryan Morris.

The Young and the White:
Just one man’s observation, but my average Uber customer tends to be younger, whiter and perhaps more wealthy than the average cab passenger, at least judging from passengers back in my taxi days 30-plus years ago. Back then, I often spent much of a night driving the North Side (or in old-time cab speak, “The Hill”). Working overnight Saturdays, I loved to witness the transition from wee-hours carousers to early-morning churchgoers. In my Uber experience, though, North Side rides are the exception, not the rule. Why these apparent patterns? Perhaps because people with more money are more likely to have the smartphones you need to hail an Uber ride. And younger people tend to be more comfortable doing business on an app.

Uber Geezers:
But there’s a place for the elderly, too: in the driver’s seat. The New York Times recently reported that many retirees are driving for Uber, to augment their retirement income, and that an AARP subsidiary is involved in recruiting older drivers. Older drivers would include 66-year-old me.

I’m Not Getting Rich:
With the exception of New Year’s Eve ($250 in five hours!) and the odd Saturday night, I have usually cleared somewhere between $10 and $15 an hour of having my app turned on, which is less than Bernie Sanders’ idea of minimum wage. I admit that I could make more if I focused on being out there during the busiest hours. But the fact is, I want to drive when I feel like it, not when Uber needs me out there handling their business.

The Dark Side:
Since that Uber-driving gun owner in Kalamazoo, Michigan, shot six people to death in February – well, I haven’t noticed any change in the atmosphere of fellowship in my Prius, so that’s good. The story got weirder in March, though, when it was revealed that the guy said the Uber app was controlling him during his attacks. Ride-sharing drivers have been charged with other crimes around the country, and many of them are listed at this website:

Talking Back

You don’t find a lot of Uber fans among the cabbies outside the Pfister Hotel. Here are the opinions of three of them.

Country of origin: Morocco
Number of years driving: 10
“There are too many taxis in Milwaukee, too many Ubers…
“I am a citizen of America. What I do for a living takes care of my family,
“It’s just so hard, man, very hard to live. Our life is upside down now.”

Alex Friedman
Country of origin: Ukraine, when it was part of the Soviet Union
Number of years driving: 20
Details: In 1999 and 2000, he paid $58,000 for his city and airport permits, now virtually worthless.
“People who use Uber and support Uber look to me like somebody who robs your house, steals your stuff and sells it to somebody else for half-price.”

Abdul Mustafa
Country of origin: Born in New York City, raised in Jerusalem
Number of years driving: 25
“If you and me are doing the same thing, we should follow the same rules. If we are operating in the same city, we should follow the same rules of the city.”
His final word on Uber: “What grows big fast, falls down faster.”

‘Driving Through Time’ appears in the May 2016 issue of Milwaukee Magazine.

Find the May issue on newsstands beginning May 2, or buy a copy at

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Tom Tolan is managing editor at Milwaukee Magazine, where he's worked since January 2016. He spent 24 years at The Milwaukee Journal and the Milwaukee Journal Sentinel as a copy editor, assistant metro editor and reporter. He lives in Shorewood.