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Preface
Paris was a city known for its beauty, but Travis Kalanick and Garrett Camp were too annoyed to notice their breathtaking surroundings. The entrepreneurs were in France to attend the 2008 Loïc and Geraldine Le Meur’s LeWeb Conference, an annual international assembly held to discuss the future of digital and tech innovation. Kalanick and Camp had fallen in love with the local cuisine, but sadly, they were also experiencing why Americans regarded the French as having deplorable customer service skills. One fateful night, they found themselves poised with the challenge of hailing a cab. They fruitlessly waved at countless passing taxis, but no matter how hard they tried, their plea for a ride fell upon deaf ears.
Earlier that evening, Kalanick and Camp were asked,
“What’s next?” from their entrepreneurial peers. Both were
fresh from respective sales of hugely successful startups:
Camp with Stumbleupon to eBay for $75 million, and Kalanick
with Red Swoosh to Akamai for $18.7 million. They knew
their futures would be bright. They just didn’t know what
the sun lighting those horizons might look like.
Somewhere during that conference, the words “get a cab
with a button” were uttered. Exactly who uttered those
words is not entirely clear. What is entirely clear is that
Kalanick and Camp would take their frustration with cabs,
return to the United States, and unleash a leviathan of
change onto the worlds of transportation, technology, and
capitalism. Their creation’s name was Uber, and it would
grow to become so revolutionary, another company of equally
intriguing origins called Lyft would vie for its throne.
Uber, the giant, and Lyft, the underdog, would wage a
vicious back-and-forth battle to the tune of billions all
in a quest to wear the crown of rideshare domination.
Meanwhile, I was an insignificant voyager adrift in
the strange seas of life. Little did I know what a
marvelous storm I would sail through.

I. November,2014(The First Week)
Trip #1
What have I done?
Perhaps this was a big mistake. Perhaps I’m in way over my head. I had just spent $50 to fill up my gas tank with 93-grade octane. $50! That was an entire shift’s worth of tips!
“No,” I said, speaking aloud to myself.
I have taken such a reckless leap of faith that I
cannot falter now. I have to own my decision and grab it by
the horns!
Just two weeks prior, I was dreading yet another
holiday season aboard the mast of the “slave ship,” the
restaurant I had been working at for the past two years. It
was a sleazy, overpriced steakhouse located inside of a
tear-down dump of a hotel in Bloomington, Minnesota.
The service industry is well known for breeding
alcoholism amongst its workers. As a busser, I was coming
to experience this firsthand. By the end of every shift, I
was dripping sweat and covered in filth. My co-workers were
astounded I lasted so long, and so was management. I was
hired in mid-2013, and after six months, my duties were
diversified into the bar, where I began casually drinking
on the job. The bar housed a giant beer cooler that lacked
security cameras. I would sneak back to “cool off,” kill a
beer, (usually an expensive craft label), tuck the empty
bottle into my apron, and dispose of it amidst the
restaurant fervor. Two beers per shift eventually became
five or more. One night I got so drunk, I couldn’t drive
home. When I asked one of the bartenders for a ride, he
said, “I’ll do you one better.” He showed me an app on his
phone called “LYFT,” plugged in a coupon he found on
Google, and scored me a free ride home. “It’s like Uber, if
you’ve heard of that. A driver comes and takes you wherever
you want to go. It’s all on your credit card. You tip them
and rate them when the ride is done.”
I was familiar with Uber from all of its bad
publicity. This Lyft thing had only been legalized in
Minnesota a few months prior. The driver who came to pick
me up made it sound like the best job in the world. “You
start and stop whenever you want. It’s one hundred percent
up to you. Sometimes I give hundred dollar rides, or more,”
he said.
“What about competition? The cab lobby is strong,” I
asked.
“Please. Cabs are going the way of the dinosaur. It’s
us now, and there’s big money to be made from it.”
I started doing research as soon as he dropped me off.
The Lyft website advertised “MAKE $1,500 PER WEEK,” which
was a hell of a lot more than I was making at the
restaurant. All I needed to do in order to join this
rideshare movement was obtain a vehicle with four doors.
Mine had two.
My initial attempt to secure a new car for free didn’t
quite pan out. I had contacted the Lincoln Motor Company
and pitched them “The Lincoln Lyfter,” vowing to turn every
ride into an advertisement in exchange for a vehicle to use
for free. The proposal was rejected and I was forced to
revisit the drawing board.
The very next night, I worked a shift so frustrating I
almost quit on the spot. I drove home swearing up a storm.
I had to find a new job. There was no way around it. Once I
was back in the comfort of my living room, I found myself
browsing online for used BMWs.
My new idea was simple. Trade in my car, finance a
used luxury sedan, and turn it into my office by driving
full time until I could make my dream job as a writer a
reality.
Seven years before any of this, I began writing “spec”
screenplays, which are written for free with the intent of
selling, while I was a junior at the University of
Minnesota. What started as a hobby quickly became an
obsession that took over my life. Everything I had done
since completing my very first script revolved around
making my Hollywood ambitions a reality. I kept telling
myself that it would not be long until I found success.
Just that summer, I had been signed to a reputable Los
Angeles talent management company. I assumed everything
would fall into place for me thereafter, although I was
sorely mistaken. Even with representation, Hollywood is
tough to break into, especially when you live nearly 2,000
miles away. I was too preoccupied with my state of
destitution to see just how foolish it was clinging to
existence in Minneapolis. My plan was to bide my time, put
a roof over my head, and write until something caught fire.
At the time, all of my spec scripts were too expensive to
get produced as a first-time writer. My manager told me I
needed to write something new that could be made for dirt
cheap. I had no idea what that script might be. I thought
rideshare could provide me with the perfect opportunity to
figure that out, and also make a sizeable paycheck doing
something that wasn’t back-breaking labor.
Though I have a college degree, I have never once
pursued what a normal person would constitute as a real
job. Instead I’ve always been a hustler. It was bred in me
after I experienced how shitty it was to go broke. Whether
it was raiding the Goodwill for designer clothes on $1.49
Tuesdays and flipping my finds online for a 1,000 percent
markup, or abusing an employee discount from a major
retailer to obtain shoes at wholesale cost, crafty has long
been my middle name. I would also sooner kill myself than
be enslaved as a corporate drone. I’ve always known I would
never be suited for a life of cubicles and spreadsheets.
I’ve also always been a firm believer in my own
creative potential. I wanted to be a writer more than
anything. I knew it would be my one true key to real
success, and so, up until this point in my life, every job
I took was high labor, low skill mixed with my sideline
entrepreneurial gigs to maximize time and effort toward my
creative endeavors.
I found a used 2008 BMW 528xi online at a local
dealership. It was navy blue, had a peanut butter interior
with 98,000 miles on its odometer, and carried an asking
price of $16,500. I didn’t have anywhere close to enough to
afford it. In truth, I had been living like a rat for the
past eight years with one item of value: a sports car that
gave me the appearance of wealth. It was an illusion, a
relic to a time that seemed more dream than memory. Up
until the 2008 financial crisis, my family had been
extremely well off. My very first car when I turned 16 was
a 2001 BMW Z3 roadster with a 3.0 liter engine. After I
graduated high school, my parents suddenly went broke, and
I was left with nothing but that car. I have vivid memories
of taking the Z3 up to the roof of this one parking garage
on campus, pot smoking my face off and cackling with
laughter at the horrible irony that had befallen me. There
I was, driving a sports car, living on less than $5 per day
with a diet consisting mainly of fast food. Even as it fell
into disrepair, I cherished that car. It was the one place
where I could go and pretend that my grim reality was just
a nightmare that would end as soon as I woke up.
But it wasn’t a nightmare. It was real. I was like a
jungle cat that had been transported to Antarctica and left
for dead. Going from riches to rags hardened me, but I had
yet to rise above it and reclaim prosperity. I had been
down in the dirt for far too long. Now I was ready to make
a change.
I felt like I was bringing the family dog to the
veterinarian’s to be put down. I still can’t determine who
got the best deal. Blue Book value on the Z3 was around
$10,000, but it was in rough shape under the hood. The air
conditioning was broken. The sound system was all but shot.
It needed new brakes. The glove box didn’t latch. It hadn’t
even been insured for several years. It was a miracle
nothing horrible had happened in my latter years of
ownership. Bottom line, Blue Book value was probably closer
to $7,000, if that.
The dealership offered me $5,000. I accepted before
they got a chance to thoroughly inspect the car and drop
their offer. Once the paperwork was finalized, I drove my
528xi off the lot and immediately met up with a Lyft
Recruiter named Brian in a hotel parking lot near the
Minneapolis/St. Paul International Airport. We went for a
road test, and an extensive one at that. We drove for more
than 20 minutes, and Brian had me talking for almost the
entire time. It was more like a job interview than
anything. When he was done asking about me, I turned it
around and asked him about Lyft recruitment. He told me
that he was paid on every driver he approved.
“Do you just approve everyone who shows up?” I asked.
“No, I actually turn most people away. If anything,
you’re atypical. I’ve tried to trick you a few times, and
you know all the rules of the road well. You pass. Now you
just need to pass the background check and you’ll be good
to go.”
For the next five days, I obsessively checked my
email, waiting for confirmation to tell me I was approved.
I was eager to start making money as soon as possible. The
thought of a $320 monthly car payment scared me, not to
mention a $130 monthly insurance payment too. It was my
first time having auto insurance in years.
After six days of waiting, on November 26th, 2014, at 1:45 a.m., the email came through:
“Congratulations! You are now approved to start
driving!”
So now here I sit, 2:15 a.m. and it’s colder than shit
out. Dressing in layers was a lesson I would remember going
forward. Yet I was too concerned to feel the cold air
seeping into my car as I loitered with the engine off. I
still could not believe what I had done as I stroked the
leather steering wheel. My heart was pounding. I had no
idea what to expect or how long I was going to have to wait
until I caught my first ride.
20 minutes went by. Just as I was about to turn around
and go back home...
That sound. “The Chime of Opportunity,” as I would come to call it. It was a pleasant tone that signified it was time for business.
JESSICA, rated 4.7 out of 5 stars by previous Lyft
drivers, was calling for a ride. I eagerly hit the “ACCEPT”
button. She was only two blocks away, according to my map.
I started my engine, put the car in gear, and pulled
out of the gas station. I was anxious and also still a
little bit stoned. I began smoking pot every single day
while I was an undergraduate in college. What started as a
crutch to escape the pains of my reality morphed into a
poor daily habit, and I had yet to break it. This night was
no exception. I had not been anticipating Lyft’s approval
email to come when it did, so when I got home from work, I
got high. The weed was nothing to prevent my driving
abilities, just my sociability. I had always been a “loner
stoner;” big in mental thoughts, microscopic in
conversation. I wondered if Jessica would be able to
notice.
I hit the “TAP TO ARRIVE” button and put my hazard
lights on, like every other driver I had seen doing
rideshare. The hazard lights seemed to be the universal
symbol for, “I am a rideshare driver waiting for my
passenger.”
After a few minutes elapsed, a phone call came
through. It was from an unknown number with a 415 San
Francisco area code. I would later realize all rideshare
calls were routed through generic numbers like this. I
reluctantly answered the phone.
“Hey, we don’t see you,” a confused woman’s voice said
via Bluetooth over my car’s speakers.
I felt a churn inside of my stomach.
Where could they be? What do I do?
They repeated their address to me again.
Heck if I know where that is! I’ve only lived in
Minnesota for my whole life!
I navigated the block, then the next, and then the
following until I spotted two shivering young adults
standing on a corner. They must have been boyfriend and
girlfriend.
I cranked up the heat, unlocked the doors, and came to
a stop. “Apologies, this is my very first ride. Your pickup
location was a few blocks off.” I told them.
They were too drunk to care. “Take us to Taco Bell,”
was all the man could say.
“Okay, let me see if I can find one here.” I typed
“TACO BELL” into the “FIND DESTINATION” tab on the app. It
pulled a location up just a mile away.
“Got it. Away we go,” I said.
As they snuggled in the back seat, I heard the sound
of a wet sloppy kiss, which made me cringe. Not just because it was rude, but because I have something called Misophonia. It’s a neurological condition which elicits extreme emotions of anger, rage, or fight/flight responses whenever I hear the sounds of slurping, chewing, swallowing, breathing, and in this case, kissing. Oddly, it’s never when I do it; it’s only when I hear it being performed by someone else. My weed habit significantly softened the condition from its height when I was younger, yet even still, it persisted. The two face-smackers unknowingly saved their lives by stopping on their own accord after just a few blocks of torturing me.
We drove the mile, only to discover Taco Bell was
closed. We tried McDonald’s next. That was closed too. 30
minutes went by as we bounced from shit hole to shit hole,
all of them turning up closed.
Eventually, we came across a White Castle that was
still open. As Jessica and her boyfriend proceeded to order
every single item from the menu, I could feel the glaring
eyes of the inebriated drivers waiting behind me. Our junk
food odyssey lasted nearly an hour by the time we returned
to their apartment on Humboldt Avenue South. I was excited
to see what the ride would come out to. We had driven less
than five miles, but so much time had elapsed that I was
confident...
Confidently screwed! The fare amounted to a pathetic
$14! They wordlessly got out without so much as a “Thank
you.” I was still negative for the cost of filling my gas
tank.
“I’ll resume this tomorrow,” I grumbled to myself as I
whipped the wheel around and headed home. I had burned
about two gallons of gas driving to Uptown, taking the
trip, and turning back home. It had cost me $5 off the $14
fare, and Lyft was still taking a 20 percent cut. When all
was said and done, I was paid a little more than $11; $6
factoring the cost of gas. I hoped to hell things would
improve, or I was in for a world of problems.

Trip #2 – “Back-Seat Beast”
It was the day before Thanksgiving, and I found myself
anxiously pacing around the phone in my living room.
Should I turn the Lyft app on, or should I just leave
the driving for tonight?
The trip the night before was more trouble than I had
anticipated. I had no idea what the day crowd might be
like.
After a lot of pacing, I decided to turn the app on.
Two hours insignificantly rolled past. As I was about to
shut the app off, just like the night before, a call came
through at the last second.
CLAIRE, rated 4.2 stars. She was six miles away at
Costco in St. Louis Park.
I raced down to my garage, fired up the engine, and
set off. In no time, I was pulling into the Costco parking
lot. The store was packed with Thanksgiving grocery
shoppers. Now I found myself tasked with finding Claire
amidst a sea of people. I looked down at my phone as I
idled with my hazard lights flashing.
Lyft allowed its customers to upload a personal
picture onto their account so it’s easy for drivers to
identify them. Claire, like many others I would encounter
after her, had a picture of her dog, and nothing else.
Unless Claire is a pudgy black lab mix, I don’t think she understands the function of the Lyft profile picture. When I looked up, I noticed a beastly woman of about
250 pounds frantically waving her flabby arms at me. She
stood in front of a cart full of groceries; her husband and
son stood on either side of her. Based upon the looks on
the their faces, they more closely resembled a hostage
situation than a family.
I flashed my high beams to acknowledge I saw them as I
put my car in drive and pulled forward. She continued to
wave at me despite the fact that I obviously saw her.
Does she think I’m an idiot?
I came to a stop, stepped out, and helped with the
groceries. Her prisoners piled up in the car; the son rode
shotgun, the father sat behind me on the driver’s side.
Claire just stood there and watched as I loaded everything
from her cart into my own trunk. I could feel her breathing
down the back of my neck as I labored.
I was awkward. I didn’t quite know how to initiate
dialogue with someone who, for no apparent reason, was in a
terrible mood and about to ride in my car for the next 20
minutes. “Looks like quite the feast,” I chimed in an
attempt to break the ice.
She glared and wordlessly got into the car, leaving
the cart for me to put away. I swear I heard my car’s
suspension yelp like a dog upon encountering her behemoth
weight. We were less than a minute into our interaction,
and already I did not like her. But there was one important
thing I had to always keep in mind:
Customer service.
My job literally depended upon my driver score from
passengers to stay above 4.6 out of five stars. In any
other context, four out of five stars would be considered a
good score. You’d probably stay at a four-star hotel, eat
at a four-star restaurant, or buy a four-star car. With
rideshare it was far more cutthroat. Allow me to explain:
You enjoyed the ride. The driver was relatively
pleasant, but they got honked at. They also drove a car you
weren’t in love with. You stepped out and thought you were
being generous by rating them four stars. Eighty percent is
a good score, right?
Wrong. You just recommended that the driver be fired.
4.6 was known as the “Death Zone” amongst drivers’ forums
online. If your score dipped below it, you woke up one day
and found yourself out of a job. No warning; just like a
bullet to the head. In theory, it created a system that
only allowed the best drivers on the platforms. In reality,
it added a layer of stress to an already stressful job. I
was an independent contractor, or “small business owner.”
That meant I could be terminated for any reason whatsoever
without recourse or restitution. If I got fired, I would
have been stuck with a car loan I couldn’t pay. It was
something I could never allow to happen.
I returned the troll’s cart to the stockade and got
back in the driver’s seat of my car.
“Nice car. Looks brand new.” growled the beast.
“Thank you. I just got it last week for the sole
purpose of doing Lyft,” I replied as we exited the parking
lot.
“You bought a BMW to be a cab driver?”
“I’m all about customer service.”
“Pretty stupid if you ask me,” she muttered.
Having worked four years of retail hell and another
year and a half aboard the mast of the “slave ship,” I had
come to learn that some people just couldn’t help
themselves. They’re terrible. They were born terrible.
They’ll die terrible. It’s rooted in their terrible DNA.
Nobody’s perfect, and the unsightly creature called Claire
was far from it. When we turned onto the highway, her
insufferable persona revealed itself to be just as ugly as
her outward appearance when her fanatical back-seat driving
began.
“You’re driving like a maniac! Slow down,” she snarled.
Her vocal cords were strained as she spoke, buried in deep
layers of neck fat. The husband and son didn’t say a word.
My theory was they weren’t allowed to speak unless spoken
to. I silently obliged her.
“I said slow down,” she bellowed again. I was doing 55
in a 55.
Is this practical joke of a human being serious right
now?
A weird tingle suddenly hit me. I glanced back in my
rearview mirror to find Claire’s eyes burning into the back
of my head.
Of course she’s serious. She reeks of boredom, misery
and self-loathing. I bet she wouldn’t know a joke if it
bitch-slapped her across all six chins.
I appeased her by slowing down to 50 miles per hour.
Other cars were ripping past us. A few honked. One person
even raised their middle finger as they shot past!
“How long have you been doing this?” she asked as yet
another blaring horn whizzed by.
“You’re my second ride,” I meekly replied.
“You better figure out how to drive, and quick, or
you’re not going to last.”
I was doing everything within my power to please her
and it still wasn’t enough. My frustration began to simmer
until I reflected upon the golden rule of customer service.
The customer is always right. Remain calm and kill
with kindness.
I had dealt with customers just like Claire far too
many times to count. I knew all she wanted to do was elicit
a reaction out of me. Instead I did the unexpected and
warmly replied, “Thank you for your advice, ma’am. I will
keep that in mind going forward.”
I could sense her growing anger. I felt bad for the
husband and son more than anything. She probably wouldn’t
allow them to eat Thanksgiving dinner. It would just be her
wolfing down the food and drinking the tears of their
misery as they were forced to watch and go hungry.
My cruel imagination caused me to snicker. Claire
failed to hear it over the chorus of horns shooting past
all around us.
We finally exited off the highway, where we
encountered thick traffic as we navigated through downtown
Minneapolis. When I merged into a narrowing lane, she
literally gasped like we were about to be struck. I was
doing 25 miles an hour.
Perhaps her life is so dull, she has to create
conflict wherever she goes and imagine situations are far
worse than they really are.
I was surprised to discover that Claire and her
prisoners were staying at an apartment complex and not a
barn. Despite my annoyance, I still got out and unloaded
the trunk.
“Have a wonderful Thanksgiving!” I cheerfully chirped.
It was met with nothing more than “Mmmmhmmm.”
Maybe the groceries were just for show and she was
planning to eat the husband and son instead. In either
case, I was two for two on bad passengers. I would find out
the next day that Claire had elected to use the “NO TIP”
option.

Trip #7 – “The Creep”
The night before Thanksgiving is traditionally known
as “Alcoholic’s Christmas,” or at least it is to me. It’s a
night where nobody has work the next day, so they go out to
bars and get shit-faced. This also makes it the busiest bar
night of the entire year.
The evening was non-stop from the moment I turned the
Lyft app on. I had gone from the suburb of Edina, which was
my hometown where I was situated in a dirt-cheap apartment
complex designated for senior citizens, to St. Louis Park,
to Downtown Minneapolis.
I picked up these two guys at the corner of Hennepin Avenue and North 7th Street. They were heading to northeast Minneapolis, just a few miles away. One sat in front, the other in back. The one in back, who was paying for the ride, made a comment about the comfort of my seats with an indecipherable drunken slur before he proceeded to shut his eyes.
“Well aren’t you adorable,” the one in front said when
his friend was out. “How old are you?”
“Twenty five.” I answered. When I glanced into his
eyes, I didn’t like what I found. They were dark brown with
a dead glaze. His face bore sharp, reptilian-like features
that struck me as untrustworthy.
“Do you have a girlfriend?” he asked.
The hell do you care?
I have always hated this question. I’m gay. I’ve never
had a girlfriend in my entire life, and it wasn’t something
I wanted to readily share with my passengers. I also didn’t
want to earn a bad rating by being rude, so a simple “No”
was all I could say.
“Oh why not? You’re so cute!” Even his voice was
creepy.
“I don’t like women,” I admitted.
Coming out was a struggle for me. I told my parents I
was gay two years prior, and ever since that moment, the
thing that terrified me for my entire life became a pillar
of pride. I don’t act gay or come across as being
flamboyant, so when I tell people, it often comes as a
surprise. I was done hiding my true self forever, even if
the information would compromise me.
When I saw his face, I realized I should have either
kept my mouth shut or just lied and said I was a snatch
hound. His flirtation grew excruciating as he touched my
hand. I removed it from the center console and tucked it
into my pocket.
“So do you go to gay bars?” he asked.
“Sometimes.” I wasn’t about to tell him which ones or
when.
“How come haven’t I seen you around?” he asked as he
opened my glove box and started digging around.
“Hey, stop it!” I ordered.
Before I could stop him, he extracted my insurance
card and read my name aloud.
Oh, crap!
Within seconds, I saw he was searching for me on
Facebook with his phone.
My foot steadily pushed into the accelerator. I wanted
to end the trip as soon as I could.
“So, Evan Kail, tell me. How big is your dick?” he
asked.
Is this really happening right now?!
I pursed my lips and contemplated shoving him out of
the moving car.
“I bet it’s really big,” he added.
“That’s a very rude comment. There’s nothing uglier
than someone with bad manners,” I said as we pulled up to
the destination, a sleazy dive bar.
“Give me your phone number so I can make it up to
you.”
“Out!” I snapped. I turned and tapped his friend’s
knee to wake him up. “We’re here. Time to go.” His friend
obeyed. The creep just sat there and stared.
“Go!” I barked. After he studied the legitimate anger
in my glare, he yielded and stepped out. I pulled off
hoping never to see either one again. I was told if I rated
a passenger three stars or less, I wouldn’t. Even though it
wasn’t the one paying for the ride who caused the problem,
I still had to issue a bad rating. Anything to protect
myself from ever seeing the creep again.

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