Driving for Uber and Lyft was a crazy experience. Crazy people, crazy situations. It wasn’t long before I had driven prostitutes, drug dealers, people who would become stalkers, and had a gun pointed at my head. That was the first month.

It was then I started keeping a little black book to remember everything that happened in my time driving.

I published the stories in a book — Ubered: My Life as a Rideshare Driver — in the fall of 2016, left the world of rideshare, and earned my second degree black belt shortly thereafter. Martial arts is one of the most positive parts of my life and I intend to stick with it for as long as live. My backstory is long and complicated, but in short I’ve held unique aspirations for the majority of my life. I will become a master of Tae Kwon Do at 4th degree. To me, this is the equivalent of grad school and it’s something I’m hell-bent on pursuing.

Over the past few years I grew out of my shell, put myself out there, and accomplished major goals in my life. My paths of writing and martial arts are just two more roads for me to continue walking. Where they will take me, only time will tell, but through perseverance, I’m sure to find out. But one thing is for certain- I’m sure glad to be done with rideshare.

Here’s one small excerpt from my book, Ubered: My Life as a Rideshare Driver, which is available at Amazon. Just a little snapshot of much more in the pages of the book:


Here we go again. Same song, 7000th verse.

I shut my eyes and exhaled. Sally’s Saloon was a bustling University of Minnesota campus bar, and the starting point of some of my most hellish rideshare trips ever. Based upon BRETT’S low passenger score of 4.2, his obnoxious location, and the late hour, I had a good idea of what every second of the next five minutes would entail.

My sociological prediction was confirmed with disturbing accuracy when I laid eyes on a drunken trio of college-age boys stumbling towards my car.

Odds are this will be a short trip to another college bar. Look on the bright side. At least they’re capable of walking.

“U-Uber?” bellowed the first as he fell into the front seat. It was a bad sign when the first word was just “Uber,” spoken with the difficulty of a chore rather than a means to communicate.

“Yeah, what’s the name?” I asked. Drunk college kids were notorious for getting into the wrong car.

“Brett,” he answered.

“Alright,” I said, starting the trip. Contrary to what customers believe, drivers aren’t told of a passenger’s destination until they “start the trip”, or begin the billing process. The map loaded to reveal Blarney’s Pub, another campus bar just a mile away.

I knew it. Two for two.

I slipped the car in gear and pulled off. A loud belch exploded from the seat behind me and enveloped my face in a cloud of booze vapor and junk food. I grimaced as I cracked all the windows.

“S-sweet car, brooo!” exclaimed the belcher in a deep, inebriated voice.

“Thanks,” was all I managed to reply.

Let’s see if I can keep this up. One of two in back has never been in a Bimmer. Watch.

“N-never been in a BMW b-beforreeeee,” slurred the one opposite me in back.

And now obtuse assumptions about my sexuality for the finish. In Three… Two… One-

“Bet this car gets you some mad poon!” shouted Brett. “Am I right, dog?!

Not even close.

My name is Evan Kail. I’m 27 and for two years, I was a full time Uber and Lyft driver in Minnesota. The situation above was one I had experienced too many times over the course of my rideshare career, and at first, it caused me a great deal of discomfort. I’m gay, something I didn’t readily advertise to my passengers. They just assumed otherwise and would comment as such, from inquiring about whether or not I had a girlfriend to using adjectives like “gay” or “faggy” mixed in with casual speech.

I was 24 when I first started driving, and although I was out to my family and friends, explaining my sexuality to strangers was something still new and uncomfortable. So when customers would enter my car with assumptions about my identity, I found myself at a crossroads. On the one hand, it was still a very personal subject and not something I was familiar with explaining. On the other hand, I came out for a reason- I was done hiding myself forever.

Over the course of my driving career, I learned explaining the truth yielded mixed reactions. Some passengers started out friendly and then grew hostile after learning my orientation, while others were full of wildly intrusive questions. Other times it would immediately kick off a barrage of unwanted flirtation, sometimes ending with customers soliciting me for sex. “You’ve given me five-star service thus far, but I don’t know if I’m sold yet, Evan. I’ve got a Benjamin on my dinner table that could be yours if you come inside with me. What do you say?”

Yes. That actually happened. More than once.

But reverting back to the drunken frat boy episode from Sally’s, after inquiring about whether or not I got “mad poon”, I cryptically replied, “Not so much.”

“This car is sexy as hell,” he said. We were in a 335 BMW. It was my third BMW in two years driving rideshare. To make a long story short, it was a crazy experiment that got way out of control. “What, you don’t get any girls numbers driving this thing?” asked Brett.

“I’m gay,” I admitted. Silence filled the car as the bro-bros processed what I said.

They must be thinking, “But he looks and talks just like us!”

The trio suddenly exploded with typical rude questions. “So like, do you think I’m hot? If I whipped it out, would you be into that?”

“Drop about forty pounds, take a shower, and maybe we’ll talk,” I fired back. “You two in back, try me again in like fifty years when I have glaucoma.” I’d learned that a sassy reply was always the best way to keep things from getting too personal. My foot gently pressed the accelerator to shorten the trip as best I could. Thankfully they were too drunk to notice my erratic speed and exited my car without vomiting, another commonality amongst college-age passengers.

This was just another night of my rideshare career in Minnesota. For those unfamiliar, “rideshare” is a term categorizing the legal loophole utilized by tech giants UBER and Lyft to keep a multi-billion dollar unregulated taxi service in operation. I fell into it in late 2014 when the services came to my city of Minneapolis. The comapnies advertised “Make $1,500 per week being your own boss!” It seemed perfect. At the time I was focused on screenwriting ambitions. I’d just been signed to a reputable talent management company in L.A. and needed a job that I thought would both pay well and allow me time to write a new work. Instead I quickly realized I’d stumbled onto an incredible subject all on its own, and so I began documenting the wild encounters, the hardships of being a driver, the sociology of those around me, and the subjection drivers undergo by two goliath companies at war with one another.

It was the best, worst time I never want to have again. I grew tremendously as a person in terms of sociability and self discovery. I became fearless in defining myself and projecting my voice to others. Most importantly of all, I made the most of my time between rides. I created and launched a YouTube channel (www.youtube.com/evankail) where I openly broadcasted my sexuality for the first time. I also I returned to the world of Tae Kwon Do after a six year hiatus in early 2015. That summer, I rigorously prepared for my first degree black belt test, an ordeal I previously wrote about for Outsports. Since then, I was able to complete my first book, “UBERED: My Life As A Rideshare Driver.” It’s a memoir built from my rideshare diary about my life and travels as a full time driver, which I wrote entirely in my car between trips. The book is nine chapters and is broken up into short stories, with each story being a “trip.” The following is a sports-related short story excerpt from summer 2015.

Trip #2,496 – “The Unworthy One”

I was like Forest Whitaker from “Ghost Dog: Way of the Samurai” as I rigorously prepared for my upcoming black belt test. Between rides, I would blast Wu Tang Clan, park my car, get out, and practice my moves. I even kept a copy of Hagakure in my glove box! There were a few times I worked up quite a sweat, especially during the weekend of the Fourth of July. Business was totally dead since everyone was out of town at their cabins. That Sunday, I had given a woman a lengthy ride to Maple Grove. She helped quiz me on my Korean terminology flash cards for the entire trip. Though she butchered pronunciation, she was instrumental in helping my memorization. Soon after dropping her off, I was fortunate enough to catch a ride back to Minneapolis with a gentleman who wished not to speak. I dropped him off at the Minneapolis Hotel Autograph Collection on South 4th Street and parked in a metered spot nearby. I whipped my flash cards out and continued my studies.

1. Ye-Ui (Courtesy) 2. Yom-Chi (Integrity) 3. In-Nae (Perseverance) 4. Guk Gi (Self Control)

5. Baekjul Boolgool (Indomitable Spirit)

These are the five tenets of tae kwon do. I’d been deeply contemplating these virtues and their meanings. As I quietly mused, I heard mumbling. I glanced up and saw a shirtless hobo talking to himself outside my car.

Ignore him.

I returned my gaze to my flash cards for just a few moments before I heard an intrusive tap against my window. I looked up again to find the homeless guy was staring at me.

There’s a slim chance he needs something other than money. I’ll crack my window and see what he wants.

The instant the window was cracked, his booze breath crept into my car as he bellowed, “Aye, man! Give me some bus money!”

I think you forgot, “Please.”

I put the window back up and dismissively waved him off, returning my gaze to my notes. “Man, fuck you! Rich- ass white boy piece of shit!”

I have very little sympathy for people like this, ever since my freshman year in college, when I gave a homeless man $20 to buy some food. It was $20 that I really couldn’t spare at the time, and instead of a “thanks,” or “god bless,” he just said, “Is that it?!” Now there I was, working a job, paying off a car loan, and this deadbeat piece of shit was pestering me for my hard-earned money, which I didn’t even have. I never carried cash when I drove.

I diffused my annoyance and continued to ignore him. A moment elapsed before I looked up again and saw the hobo, dick in hand, was urinating on my tire!

I have a lion’s temper that I keep caged, reserving it only for the most enraging of situations. Pissing on my car and desecrating my business was a lovely way to prop thecage open. I sprang out of my car, blind with fury.

“You piss on me, white boy, I’ll piss right back,” he cackled.

Time slowed. I scrutinized his body up and down. Floating ribs are among the easiest bones to break in the human anatomy, and his were wide open. One punch was all itwould take, and there was nobody around. My fists knotted as I lowered my stance and prepared to pounce. Just as I was about to learn this drunken bastard seven ways fromSunday, a voice spoke in my head.

Guk Gi- Self control.

I was about to take one of the most important tests of my entire life; a test not just of skill, but of understanding, too. Was this deadbeat really worth it? Of course not! He probably didn’t even know what day it was. There was no way in hell he was worthy of experiencing the wrath of a tutelage a thousand times older and wiser than he is, was, and ever would be in a thousand lifetimes on this planet.

A calming breath overtook me. My fists undid themselves. I blinked. The lion went back in its cage. I got in my car, hit the ignition button, and drove away.

No doubt about it, I made the correct choice that day. It was a test sent from the depths of fate to challenge me, and I passed with flying colors.


Evan Kail’s book Ubered: My Life as a Rideshare Driver is currently available in digitally on Amazon, and as a PDF on Payhip. He just launched a crowdfunding initiative where signed paperback versions can be purchased, along with a host of other goodies.

You can also view this Rated-R video Kail put together about his book: