My strange, unexpected love affair with delivering food

"Hi, David, this is Michael from DoorDash. Any chance you have a few minutes to chat over the phone sometime today?"

Oh, shit, I thought. Am I being fired?

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I'd been a part-time delivery driver  —  a "Dasher"  — €” for three weeks by that point, driving around San Francisco on a scooter, delivering everything from burgers to pad thai to frozen yogurt. Can you even fire a contractor? All of the mistakes I'd made over the past few weeks flashed through my mind, like when I ordered the wrong size bubble tea at Boba Guys or when I forgot the hot sauce packets at Taco Bell. Once I had to tell a customer I didn't have his milkshake, or any napkins, because the milkshake had spilled all over the back of the moped, and, hey —I had to clean it up somehow.

I almost never wear the red DoorDash shirt they want us to wear. I bet it's the shirt.

And then I remembered the Red Bull.

A week earlier, an order had come in for 10 cases of Red Bull. I thought about having it reassigned, as there are only so many places to safely stow cases of anything on a moped, but it would pay well, so I figured it was worth it. I zipped over to the pickup location, a BevMo liquor store on Van Ness, grabbed a cart, and set off in search of the energy drink. Ten minutes later, the cashier hardly batted an eyelid as he swiped the magical DoorDash credit card for $94. I managed to squeeze the box he gave me in between the moped's steering column and seat, and with my legs sprawled outward, like a mother giving birth to a giant box of energy drinks, we barreled down Nob Hill in the direction of the hotel where the customer was staying.

I've never had a customer go MIA like the Red Bull guy went MIA. Not only was the name on the order different from the name on his voicemail, the hotel staff had no record of either person staying there. I phoned the overly calm but kind lady from DoorDash support, and she tried calling, texting and emailing the guy as we waited  — me, the front desk staff, and the unwieldy box of Red Bull. Five minutes passed.

Ten minutes.

Nothing.

"It works the same way it does with food," the calm lady said. "If the customer doesn't respond in 15 minutes, you are free to eat or discard whatever it is they ordered." Which for an order like organic churros or ice cream would have been great news. But not 10 cases of Red Bull. The front desk staff didn't want it, either. I was stuck with it.

After I'd stared at the box for a few days and still hadn't heard from the guy, a lightbulb went off in my head. I zipped back over to BevMo, walked up to the same cashier as before, unwanted box of Red Bull in tow, placed it on the counter, and said, "Hi. I'd like a refund, but could you put it on a different card?"

"Sure thing!" he said, without batting an eyelid.

This was the exchange replaying in my mind as I walked out of the restaurant to call Michael from DoorDash and receive my sentence. Maybe some guy just wants his Red Bull. "Hi, Michael?" Oh shit oh shit oh shit.

"Hi, David, thanks for calling. I just wanted to tell you ... congrats! For the month of October you were our Dasher of the month, with more deliveries and a higher rating than any other Dasher in the country."

You've got to be kidding me.

DoorDash came into my life the way most things do: all of a sudden and without careful planning. At the start of October, my friend Evan told me about his short stint as a driver for Postmates, a DoorDash competitor. After passing the background check and sitting through the hour-long orientation, he was eager to begin his first shift. But two hours and three deliveries later, his rating was just 3.5 stars, low enough to land him on probation. Sit through another orientation, they told him, and we'll reset your rating back to 5. So he did. And then never delivered again.

"Why'd you bother?" I asked him.

"I couldn't rest knowing that my rating was 3.5 stars on some app," he said.

At the time I thought this was silly; I hadn't yet agonized over my own rating. The idea was intriguing, though. The next morning, I applied to be a Dasher.

I had never heard of DoorDash before moving to San Francisco, but that was probably just me. There are rumors swirling around that the company is in talks to raise money at a $1 billion valuation, making it a so-called "unicorn." It's expanded from just four cities at the start of 2015 to 22, and according to a recent profile on the company, there are "tens of thousands" of Dashers in these cities.

The company was founded in 2013 by a group of computer science undergrads at Stanford. Just two years later, one in three Silicon Valley households uses the service. Dashers are paid more in nearby San Francisco than in any other city: $10 per delivery, plus tip — usually 15 percent of the order total.

It isn't all tacos and unicorns, however. DoorDash was recently named in a class-action lawsuit for the way it classifies Dashers as contract workers. Critics say the company, as well as competitors GrubHub and Caviar, are taking advantage of the classification to avoid paying payroll taxes and providing employee benefits and health care.

Food delivery was never supposed to be a moneymaker for me. It was never part of any long-term career goals, either. I'd been in San Francisco for four months by that point, working as a freelancer, designing apps and marketing campaigns for startups. I eventually want to start a company and learn to write, but neither would be helped by riding around a city on a moped — or so I thought.

I'm what Peter Thiel would call an indefinite optimist: I have no concrete, long-term plans for my future, but in general I believe it'll turn out okay. Good, even. I dropped out of college not once but twice to pursue this uncertain yet exciting future. Adults call this "finding yourself." I call it living.

Coming from a generation addicted to "direction," I take pride in my relative lack thereof. Without a map, life becomes a series of unexpected turns, kind of like a DoorDash shift. Hours and days fly by, and suddenly you're in a radically different place from where you started.

DoorDash rejected my application three times. The reason? They wouldn't tell me. Contact the company that runs background checks for us, they said. I requested said background check and saw two "Improper Equipment" violations on my driving record from when I was in high school. Really? I was applying to deliver on a bike, for Christ's sake. I pestered them over email for a few days until they relented. Show up here for your orientation, they said.

At orientation, they tell you things like: Here's how to use the platform, here's what to do when shit hits the fan, here's how to keep a high rating. I sat in the back next to a walker from Oakland. She didn't want to deliver with a moped, a car, or even a bike; she would do all deliveries on foot. When I whispered to her that this sounded relaxing but not lucrative, she just laughed.

Later that night, I told my improv partner Sophie about the orientation and my plan to be a delivery driver. "My company makes something that is going to make your life so much easier," she told me. "I work for Scoot."

Scoot is bike sharing for electric mopeds. There are 400 of them scattered throughout the city, and you can drive one around for $4 an hour. When you need to get somewhere, you open the app, tap to reserve the closest "scoot," walk there, turn it on with your phone, and go. It's the ultimate food delivery vehicle. Unlike a car you don't have to worry about parking and you don't have to sit in traffic, and unlike a bike you don't have to suffer up any hills. It's like magic.

At 5 pm on a Friday, five days after I applied to be a Dasher, I reserved a Scoot, opened the DoorDash app, and swiped to start my first shift. And immediately: BEEP, beep, beep. Boom. Go to Little Chihuahua on Divisadero, it said. Whoa.

And 20 minutes after that, Little Delhi.

Curry Up Now.

Pancho Villa Taqueria (the worst).

Blue Barn.

The orders started to blur together at some point. They were coming in so fast, I felt like the blond runner boy from The Incredibles. It was, well, incredible. I drove up hills I didn't know existed, down alleys I wouldn't recommend anyone go on foot. Eventually my shift ended, and I swiped over to the Earnings tab to see how I did. Holy shit. Five hours, 11 restaurants, it said; $175.

I was hooked.

If scientists were to study us Dashers, I swear they'd find something like dopamine released in the brain at the sound of a new order coming in. Dashers have three minutes to accept an order before it is automatically reassigned to another, more worthy Dasher.

The experience for a Dasher is largely thoughtless. Once you accept an order, you just do what it tells you: go to Taco Bell, have the magic credit card ready because they aren't a partner, don't forget the Pepsi.

It can be stressful when you're first starting out, though. You and your ability to earn money are at the mercy of the Machine, the mysterious black box that determines which Dashers get which orders and when. You know nothing about how the Machine works, so when the orders aren't coming you just sit there, wondering about its algorithms and where you should go to increase your chances of being picked. There is no heat map that shows where the most orders are coming in so you can adjust course accordingly.

There's nothing worse than a long wait between orders. When it's really bad, I swear to myself that I'll never do DoorDash again and maybe I'll switch to Postmates or quit this delivery business once and for all, goddammit. Then an order will come in, and I'll drive off and forget about it.

One night I was talking to a man behind the counter of a shawarma place on Valencia Street. He'd owned the place for 30 years. "How do you like working with DoorDash?" I asked him.

"It's good," he said. "Some nights it's slow, and some nights it's good. When it's slow, store busy. When store busy, DoorDash slow." I'd never thought of it working like that, but it made sense. When people don't want to leave their houses  —  because of rain, or cold weather, or because they live on a hill somewhere  —  they are more likely to have food delivered. And vice versa.

I'll chat with staff at the restaurants, and maybe other Dashers I meet on the road, but never the customers. I've learned that the doorstep of a customer is not a place for casual conversation.

Only one guy, out of hundreds, has ever tried to talk to me. After I handed over his tightly packed bundle of Chinese food, he asked me how I liked delivering for DoorDash. "You know," I stumbled, taken aback by the question, "you can set your own hours and stuff..."  He had no follow-up questions. Not that I blame him; small talk is dreadful on even a full stomach. Here's how the exchange normally goes down:

"Hi there," I say, smiling, holding out whatever it is they've ordered.

"Thanks!" they say. Most people smile back, unless I've spilled their chocolate milkshake and stolen all their napkins.

Sometimes I'll add something like, "Good choice, by the way!" I won't say this if I don't actually think it's true, like if they ordered from Pancho Villa or something, but sometimes I lie and say it anyway for the sake of friendliness and, of course, the rating.

Your rating is like gold. Like, if you were trusted with a block of gold and told to moped around a city without losing it or dropping it, that's how you would feel. You don't fuck with the rating. You pull up to a house and put a smile on your face and ring the doorbell or take the elevator up 30 stories or enter through the back gate and take a right and then left and then do jumping jacks and say, "Open Sesame," or whatever the hell it is they put in the Delivery Instructions box. You do not fuck with the rating.

One of the things they tell you in orientation is to never turn and walk away until after the customer has closed the door. It can make the customer feel like they're just another item on your to-do list, they say, so wait until they close the door to turn and leave.

I've found this to be terrible advice. On my first few deliveries, I would stand there, waiting for the customer to close the door, looking them right in the eye so they'd feel like the opposite of an item on my to-do list, and they would ... not move. Am I supposed to tip this guy? they were probably thinking. Is this the part where he follows me into my house and kills me? I now time it so that we turn together, like synchronized swimmers. They go inside to devour the warm grub I've just lugged up the hill for them, and I shuffle back to the moped to eagerly await my next order.

Sometimes when the orders aren't coming fast enough, I'll think of that old man running around behind the counter of the shawarma place on Valencia, and I'll relax a bit.

Michael from DoorDash had called to congratulate me, but he also wanted to know how I'd done it: How was it possible that in just three weeks I'd made more deliveries than anyone else on the platform, and with a higher rating?

I told him about the scooter. And that for those three weeks, I signed on every day during lunch, a few nights during the week, and at least one night on the weekends. I smiled at the customers while handing them their food. Maybe I knocked a few people out with whatever Southern charm I had left after living in Boston for three years. I didn't really know.

What I did know was that I loved every minute of it. Even the icy nights when it felt like my fingers might fall off, the hours spent watching the madness behind the counter of Pancho Villa wondering when the hell they'd start working on my burrito, the agonizing gaps between orders, scooting around aimlessly thinking maybe I should get more hobbies.

I swear I probably know more about the city of San Francisco than Google does. How it's always warmer at the top of Russian Hill, and you feel like you're on top of the world. That there's a Lombard Street knockoff in Potrero Hill. The way 17th Street just keeps going up, and up, and up, and eventually you're in the clouds. The stretch of Market Street with the best views of the city. And elsewhere, the smells of human urine. The smells of food being cooked in homes that aren't expecting a Dasher, and in restaurants that are.

Sometimes I wonder why people are so lazy. Like, why would anyone pay $5 to have a bagel and lox delivered three blocks? It's a question I get constantly from people I talk to about DoorDash.

Maybe the answer lies in something Seth Godin repeats often in his writing, that "people don't buy goods and services. They buy relations, stories, and magic." I think that's so true. That idea that anyone with a smartphone can get to your house with a moped trunk full of Thai food in 20 minutes is nothing short of magic.

And when the Machine is working well, and the orders are coming in, and Pancho Villa is done with the food before I get there, and the hungry person on the other side of the door is genuinely surprised at the speed with which I got to his house, €”well, it's magical for me, too.

Also: Lin (or Grant?) ,  if you're reading this and you want your Red Bull, let me know. I don't have it anymore, but I do have your money.

I am eagerly awaiting your call.

David Oates is a product designer based in San Francisco. In his free time, he delivers for DoorDash. You can follow him on Twitter at @deoates.

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