500 Rides

(Passenger names have been changed. The four-letter Rideshare company name is redacted.)

XXXX App: “4:48 a.m. Jaap, 14 minutes away. 24 Minute trip south-east.”

Me: “Accept.”

The GPS guides me to Jaap’s house. Sometime today I will give my 500th rideshare ride. That milestone feels worthy of some reflection. What have I learned? What have I earned?

I drive early mornings because I don’t like my car puked in.  I’ve tried driving other hours, to find the sweet-spot balancing demand against customer attitude and inebriation. Mornings, especially Monday and Friday, are good. I like coherent passengers, going somewhere important to them – like work, or the airport. Jaap’s trip description in the app means he is very likely going to the airport. 


The offer for my first ride… Ride #1… didn’t tell me that.  Ride #1 said, “Steve: 10 minutes away.” On Ride #1, the app was new.  The offer to accept a ride is accompanied by an ominous, beeping countdown.  I have fifteen seconds to decide. Declining hits my “acceptance percentage.” Acceptance percentage determines whether I get the strategic nugget about ride length and direction.  

I accepted. Someone has to be my first victi… er, customer. The saying “You always remember your first.” flashed through my mind. Steve was a DUI convict headed to a bar, 6 minutes away. I wonder how many lives “rideshare” has saved? I can count at least 5 out of my 500, and remember… I drive days. It’s always five o’clock somewhere.


I pick up Jaap, drive him 24 minutes to the airport. We have an exquisite conversation about sustainable industries, climate catastrophe, our work histories. He gives me two impassioned pitches for stocks I should invest in and hold for the coming green revolution. As I pull away from the departure terminal at General Mitchell Airport, “The App” lets me know Jaap has given me a $10 tip.

Part of me is driving XXXX because I keep 100% of tips. That part of me was not informed that only 10% of riders tip.  The CFO of the Wealth Management firm didn’t tip.  The Marquette University Dentistry professor didn’t tip.  No one who said, “Great ride! I’ll tip you in the app!” ever actually tipped in the app.

The service workers tipped. The riders heading to minimum wage jobs tipped. The grieving family needing a ride to a funeral tipped. The recovering alcoholic on his way to an AA meeting tipped.

I’ve learned two types of people tip: Decent people, and people on corporate expense accounts. Sometimes those groups overlap. 

A lot of people want to know why I’m driving.

Part of me wants to know who uses these services. Part of me wants to write an article. Part of me wants a flexible way to earn some cash, which writing has so far failed to provide. I sold an article to a national magazine for $432 in 2003, before everyone was a content provider. Before blogs were the rage. Before Journals offered “exposure” in lieu of pay. Before service aggregators became monopoly strangleholds on royalty payment. Before the “gig” economy.

But I don’t have to drive. I chose to.

App: “5:42 a.m. Shelandra; 10 Minutes Away; 26 minute ride North”

Me: “Accept”

I arrive at a small ranch home with a wheelchair ramp. This probably means I’m picking up a night-shift home-healthcare worker. I get a lot of them. The rides are long — from some suburban, health-insured person’s home, or a senior living center, to a tattered apartment complex on Milwaukee’s northwest side. Always an African American, almost always a woman.

Shelandra gets in, with her sleeping 2 year old child.  She straps the 2-year old into her car seat, and tells me she’s lucky that her client allows her to bring her daughter to work, sleeping over every night, because she has no childcare available.

Milwaukee Harbor entrance and lighthouse, at sunrise.
Sunrise over Milwaukee Harbor

Shelandra falls asleep in the back seat. I drive over the Hoan bridge at sunrise. Milwaukee at sunrise is beautiful, and with any luck I’ll get three more trips over the Hoan today. I never tire of seeing the clouds and sun dapple Lake Michigan’s ever changing, surface. Subtle shifts, always new. 


This view is one of the major, intangible benefits of driving XXXX. watching the light shift on Lake Michigan is a non-negotiable form of compensation. Great conversations is another.

The view from the Hoan Bridge, heading north.

It’s certainly not the actual payment that makes this worth doing.

Passengers, or PAX as they’re known on the Reddit forums, frequently ask how much I make. They’ve heard “you can make big bucks” driving rideshare.

Big bucks are relative.  One rider, a four-year fiberglas-mold technician, bragged how he had been given a raise four straight years for his excellent work, and would soon surpass $16 per hour. I’m stunned how many of my PAX earn around minimum wage. How many are thrilled to simply be employed. The bills don’t wait.

Here are the big bucks for this rideshare driver:
First, XXXX doesn’t pay me for the trip (time or mileage) to pick up a passenger. They pay only for driving, or waiting for a customer. $0.9375 base per ride. $0.87 per mile. $0.15 per minute, including wait-time for pickup. 

Every time I wait for a customer — who has been told by the app to be waiting outside for my arrival — my “wage” is unilaterally lowered to $9.00 per hour.

Depending on conditions, incentives, local sporting or festival events, and my ability to “play” the game, I can squeeze out anywhere from $16 to $45 per hour, with $24 being average, PRE EXPENSES – Deduct gas, insurance, and wear and tear.

Some PAX think I take home everything they pay. It doesn’t help that the company keeps customers and drivers in the dark about each other’s financial stake in their transactions. I gladly share what I get paid in exchange for a customer showing me what they are charged. I’m happy to raise a customer’s awareness.

“I’ve looked at XXXX from both sides now…”

One home-health worker was shocked, as was I, to find out that I earned $16.06, while she payed $69. Ignore the “elective” charge for a rapid pickup. That cost her $15.00. Her fare for the actual trip — from Sherman Boulevard and Center, to just beyond 76th and Brown Deer — was $5.00 per mile.

I’m not sure “rapacious” is a strong enough word for the price she had to pay to stay employed, or for the “separation” policy, breaking the link between rider fare and driver pay, implemented a few months before I began driving.  Drivers get flat pay, no matter how deeply the company may be able to gouge the customer.


We arrive near 29th and North, and I wake Shelandra, help her unbuckle her daughter. She wishes me a “Blessed day” as she gets out.  I make $19 for the trip, and wonder what percentage of her daily pay goes to transportation.  Does she know the options? Has she done the math on getting a car? I have no way of knowing. She tips $3.00.

App: 7:05 a.m. Cerissa, 8 minutes away. 6 minute ride West

Me: “Accept”

I know, I know. The pick-up is longer than the ride. But I can’t say no. I’m in the middle of a “Streak Bonus” incentive. If I don’t accept three consecutive rides I won’t be able to claim the $12 reward! This app is like a video game; incentives sprinkled here and there like Jewels in Zelda. Subtle nudges to get me on the road and keep me there longer.

Cerissa is a beautiful woman, tired and rumpled looking, in jeans and white tank top.  She rolls into the back seat.

“How’s your day going so far?” I ask, pulling away from the curb. I ask every passenger this same question, to gauge their mood and desire for conversation.

“Tired. Maybe I should have just slept with him?” Cerissa begins.

She unreels a story of the previous evening: a wedding rehearsal, a friend-of-a-friend she kinda knew, cocaine – lots of cocaine, return to his apartment…

“And then, he just talked and talked about his feelings for four hours. I shoulda fucked him to make him sleepy, and I coulda got some rest.” The six minute ride to a Marquette area apartment was over in a flash.


People will apparently tell a driver just about anything.  As it turns out, XXXX riders often need more than a ride. One distraught young man asked if I thought it wise to avoid relationships because they always end in pain? He had just been betrayed by a girlfriend.

When one young female customer answered my questions with a single word and darting eyes, I could tell she was nervous. I revealed that my wife and I are celebrating our 30th anniversary. Tension melted. We ended up comparing techniques for making French macaron cookies.

Customer feedback consistently says I’m a friendly driver. This has been a surprise to me, as I tend toward “misanthropic introvert.” But something about the driver role opens me up. I enjoy dipping briefly in and out of diverse lives, offering perspective and opinion, maybe giving someone a reason to laugh, or hope.  

I begin to wonder if it’s an asset or liability that I can emotionally connect, with empathy and humor in short bursts, when I know I don’t have to really get to know a person… but only if they’re paying me.

PAX frequently need more than a ride.

Around Ride #200 I developed a menu: “What do you need from your driver today? Tour Guide? Advisor? Silence? Priest/Confessor? Therapist? Comedian? Karaoke Singer?” I’m not sure it generated any tips, but I’ve made a few people laugh out loud, and those rides became great conversations.

App: 8:18 a.m. 8 minutes away. Gerald, 16 minute trip SouthEast

Me: Accept.

I’ve lived in Milwaukee 36 years. I thought I knew the city. I did not. I’ve learned shortcuts, and angled streets I have never taken. Everybody knows the diagonal “spoke” roads, radiating out of downtown Milwaukee like the arms of Mark di Suvero’s sculpture at the end of Wisconsin Avenue: Forest Home, Beloit, Fond Du Lac, Lisbon. But the diagonals across those roads? Grantosa, Roosevelt Drive, Flagg, Winnebago. Minor epiphanies.

At least 50% of my rides have come from the northwest quadrant. “The hood.” “The ghetto.”

So many derogatory names for such a huge area of our city. I never hear anyone call it “The place where 1/3 of Milwaukee’s population lives, raises families, and makes a living.” These are the people who tip. Service industry workers who apparently understand that if we don’t look out for each other, “ain’t nobody looking out for us.”

Vibrant. Summer streets burst to life every afternoon. Community. Always busy: either taking people to work, or making “hops” across the North Side – to a girlfriend, a cousin, a party.  I drive with my head on a swivel. Playing defense. I’ve seen the aftermath of 5 head-on collisions in my short tenure.  I’ve been passed from behind at a four-way stop, by someone going 40mph.

The Northwest side is also home to some of the most decrepit roads in the city. I know the embedded realities of red-lined neighborhood politics in Milwaukee, but streets that destroy suspensions don’t selectively choose which cars to destroy by race.  Even if potholes were racist, policy resulting in a majority of them existing in the Northwest quadrant seems negligent at best.  Vindictive at worst.  Wait… maybe potholes are racist?

Gerald, in the car now, a consultant at a defense contractor in “the core” opines “Why would you fix the roads for a bunch of people who just want to tear up the city anyway?” I push back, that I’ve not had any riders from this area who want to tear up the town. Most simply want to get to work in the absence of public transport that has been slowly gutted since I arrived in the ‘80s. Shouldn’t a city government strive to make the entire city functional, and support the well-being of all? Gerald chooses item 3 on my menu. Silence.

In nearly 500 rides, I’ve only encountered three riders I wanted to kick out of my car.

App: 9:15 a.m. Ulysses. 10 minutes away. 30 minute ride Northwest.

A happy, young Black man bounds out of the credit union and enters my car. We’re headed to the Auto-Mall, at Good Hope and I-45. Ulysses is 18. He has plans. He talks openly. He knows where he is, where he’s going, and how he will get there. He’s psyched to be buying his first car, from a dealer he feels he can trust. He’s worked hard, and with the help of his auntie raising him, he’s finally here.

I ask what he’s buying and how much he’s paying.

“2017 <brand redacted>, and I can handle the note. Just a little over $400 a month.”

“How much down, and what interest rate?” I ask.

“$800 down, on $14,000 total,” he says, scanning the contract on his cell phone, “and interest is… 28%. But I can afford the note.”  For the next 15 minutes we talk about the concept of predatory, possibly discriminatory lending. When we arrive at the dealer, I pull out my iPad and show him an on-line calculator: He’ll be paying $26,000 plus on the $13,200 this “nice, trustworthy” dealer is financing for him.

“Fer real?” I show him the numbers and demonstrate a few alternate interest rates to convince him how badly he needs to re-finance, as soon as possible.

“Get a co-signer, get a loan from your credit union. Even at 10% (which is horrendous) you’ll save thousands of dollars.” Ulysses thanks me profusely, as he steps out of his $67 dollar XXXX ride, to walk into the dealership and sign for the car he so desperately needs to make his plans come true.

This is my best moment as a(n) XXXX driver. I’ve hopefully made a life a bit better for a person.

It is expensive being poor, and we allow it. We encourage it. We thrive on it.

Apparently, some of us make it our life’s purpose to take advantage of those without means, at every step. Because we can. Because financial regulation and affordable public transit are simply beyond the ken of city and regional leaders.  “That would be socialism!”

I pray for another ride over the Daniel Hoan bridge. Soon. I need to be reminded that once Milwaukee was a shining example of public infrastructure; policies enacted by a string of socialist mayors.

App: 6:00 p.m. Daniel. 4 minutes away. 14 minute ride South.

Perfect! The Bucks’ NBA championship series is on, and this ride will drop me down in the pre-game action.  The map showing the pickup location looks really familiar.  As I pull onto his street, I realize why it is so familiar.

 I had driven Daniel a week earlier, to one of the Bucks’ Divisional Series games.

“You’re lucky to have tickets to this little bit of Milwaukee history,” I said.

“Oh, I don’t have tickets. I’m going to sneak in.”  For the rest of the ride Daniel outlined his approach to free seating at every major event in Milwaukee. He was getting in, and if not, “What’s the worst they can do? Kick me out.”

Every rider has a plan they’re working.

In 500 rides I’ve had 7 repeat customers. The Menard’s worker from County Sligo, Ireland. The drug mule (a guess). The rent-boy (another educated guess). The fried chicken devotee.  I know Milwaukee’s a “smallish” town, but this frequent deja-vu surprised me.


There at the end of the street was Daniel, but this time with three others. My car is authorized to carry a maximum of 3 passengers. The front seat is off limits because of COVID, but I’m vaccinated, and I arrange a $10 cash-up-front tip in exchange for taking the fourth rider.  Of course, it’s against XXXX policy, and if I had an accident my insurance would not cover the extra rider.  You have to take some risks in life, right? It’s not like I’m trying to sneak into a Bucks playoff game of something!

“So, heading to the Bucks game?” Daniel doesn’t seem to recognize me.  “Getting in free again?”

His head snaps toward me, then a laughing recognition washes over his face.

“Oh damn, it’s you! Yeah… last time I ended up in seats that were $8,000 on Stub Hub.”  It seems that after evading arena security, one must then find unoccupied seats, by going on Stub Hub to find unsold tickets.

“And you’ve got three apprentices this time, eh?”

“Yeah, we’re gonna try.”

There’s electricity in the car, heading downtown to the NBA Finals game 2, at a new arena, in a town that hasn’t celebrated like this in 50 years.  On arrival, four guys roll out of my car to make a “championship run” of their own.  I wish them luck and try to get quickly away from the untenably heavy throng of green-clad Bucks fans pouring into the Deer District.  I call them “The Curd Herd.” Maybe that’ll stick?

App: 7:45 p.m. Stanley. 7 minutes away. 16 minute ride Southwest.

Me: Accept

Riders and drivers are asked, every time they open the XXXX app, “Do you have your mask?” Stanley opens the back door, swings himself in, and simultaneously says, “You don’t need to wear that mask for me.” I cringe. Another one. 

“I’m not wearing it for you. Company policy requires we are masked, and rider policy also requires you be masked,” I say as I hand him a fresh mask from my supply. Another expense.

I could recreate the next 5 minutes of conversation verbatim, but it boiled down to Stanley’s view: “Masks are futile, diapers on our faces. COVID is a hoax. It’s all about government control. I know more science than you could possibly know.”

He’s a professional gambler.

Not with my life, sir. Not for this pay. Get out. It’s amazing how fast free-market libertarians become angry complainers when an independent contractor exercises the invisible backhand of the market against them.

App: 8:40 p.m. Youneek. 8 minutes away. 18 minute ride south.
Me: Accept.  Ride #500

Another home-health worker. Exhausted. She wants to buy a car, but can’t save enough. As I drop her off I thank her. “Congratulations. You are my 500th rider. Have a great evening, and thank you for choosing XXXX.”

Dragging herself out of my car, she says, “Shit… I don’t have a choice,” and shuffles toward her apartment complex. I feel bad, knowing I will drive home and simply choose to never do this job again.

I’d say the 500th ride was anti-climactic, but there were no climaxes in any of the 499 rides that preceded this one.  Maybe a brief pride-swell after giving Ulysses financial advice.  Definitely a new appreciation for the struggle of so many people hustling to scrape out a living. 

I leave my experiment feeling better about the human condition, based on all the good rides and good conversations.  People are loving. People are giving. People are dreaming, striving, and getting by. But I’m drained knowing that the system grinds on: public infrastructure is gutted, enabling profiteers to rule the unregulated new world of internet service aggregators, while the have-nots are fleeced.

And the fleecers don’t tip.


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