“Hey, Jesse, what’s your 20?” Heather MacKinnon, a friendly blonde woman from Boston, asks into her clunky black walkie-talkie. The sleeves of her black and red t-shirt are rolled up, exposing pale arms filled with tattoos.

“Market and 9th,” Jesse Rodarte shoots back, responding to a radio code for location that dates back to the 1930’s.

Our 20 is the corner of Valencia and 21st street – or “the benches” as the bike messengers who congregate here call the spot. No matter that the benches are metal chairs and tables, the shade of the Valencia Whole Foods awning is the Mission base for the messengers who work for TCB Courier. It’s here that they stretch out their legs, divvy up work, and bond during the slow times.

Bike messenger work, historically more geared towards packages and legal documents, has recently made a shift toward food delivery – a trend that TCB claims to have advanced greatly in San Francisco. Some 60 to 70 of its couriers deliver from 70 or so restaurants during two shifts: 10:00 a.m. to 4:00 p.m. and 4:00 p.m. to 11:00 p.m.

The Mission is one of four zones, though their routes can also go between zones. The messengers – around four to a zone – are given an hour for each job, but that doesn’t mean they actually have an hour to deliver it, says MacKinnon. “It all depends on when the job is ready from the restaurant,” she says. So if a restaurant is running late, it’s on the messenger to make up the time.

Gabriel, from central California, who declined to give his last name, says his favorite route follows the “Waggle” through the Mission to downtown. You get the culture of the Mission and the liveliness of downtown, he says.

“He likes the waggle shift?” asks MacKinnon in disbelief. “No one likes waggle!”

“It’s far, it sucks, and sometimes it gets to be too much…and then you have to coordinate with other riders,” says Jerry Kammerzell, referring to large downtown orders that require two couriers.

“Sometimes it just doesn’t work out,” he says, and then you end up with something no customer wants: cold food.

“Taking Indian food from the Mission all the way to downtown with a couple other orders on you, sometimes it gets turned a little sideways,” he adds referring to a dreaded outcome: spilled curry. “But you’re guaranteed to make good money.”

Another messenger named Ian sees routing as a game. “You have to play the whole thing like a chess game,” he says, “You have to be good at mapping out stuff and you have to be proactive.”

You also have to be acquainted with the buildings you’re delivering to, Ian adds. Some are quick drop-offs, but some – especially downtown – involve security passes and multiple elevators to get to the customer.

Messengers more or less get to choose their zone, but newbies have the last pick.

“I was doing the Marina shift for the first two weeks, maybe even the first month. So I had to learn how to get around the hills,” says MacKinnon. “ And it was a lot of learning the hard way, like going up Steiner and thinking oh, I should have gone that [other] way.”

Ian describes the job as “sprinting for 13 hours” except when you aren’t. “You’re going to be working as hard as you can and then waiting in an elevator, sweaty, and then getting out and sprinting again,” he says.

The worst thing that messenger Gabe has ever delivered? “Two cases of wine with 12 bottles each.” Others – like Chas Christiansen, who founded TCB in 2009 – say the most difficult is either curry or milkshakes.

While TCB riders are taught to always keep calm and have a positive attitude, customers can sometimes push their buttons.

“For some reason people out here will pretend not to know how to tip. They’re like oh! I, oh uh…I thought I put it on the card!” says MacKinnon, adding that they will conveniently ‘not have cash’ on them.

Other uncomfortable situations: the people who answer the door naked and arguing couples.

One time Christiansen dropped off sandwiches to a man whose girlfriend had locked him out of the apartment. “In the process of him asking her for the $5 to pay up the order they got into another screaming match.”

Sandwiches flew. “I was just like it’s not worth $5, I just left.”

Although TCB’s main focus is on food, they also do other deliveries.

“A couple broke up and didn’t want to see each other, and I went to her apartment to get the keys and deliver them back to him,” says a messenger named Jake Ricker. “So that was pretty awesome.”

Each delivery company – and there are almost a dozen in San Francisco alone – has a different system: some treat their riders as employees, but TCB’s riders are independent contractors, which means they don’t have benefits but ostensibly have more flexibility.

“It’s a gift and a curse,” says a rider named Dee, who declined to provide her last name and who has been working for TCB for around two years. “It kinda makes it easier to take off and do my own thing and I’m not tied to a company with normy job restrictions, but…it’s harder around tax time now.”

They are paid a delivery fee plus a small percentage of each delivery, plus tips, which makes developing relationships with their customers critical. “On average an experienced rider usually makes between $120-$160 in a six-hour shift,” says Christiansen.

Christiansen says that a lot of riders choose to work the same shifts regularly, so they develop a rapport with their customers. Christiansen, for example, learned quickly eight years ago to bring a treat for Sean’s pitbull Daisy. Other endearing qualities can be remembering security codes or simply a person’s name.

The riders’ pet peeves: slippery restaurant floors, people who ignore their phones after they’ve ordered food, and customers who don’t understand when a gift is being delivered to them from someone else.

“You’ll try to give somebody like, ‘Hey, here’s your flowers!’ and they’re like ‘I didn’t order flowers,’ and I’m like, ‘No, I swear, I promise this is you,’” says Dee.

Bike theft is also a serious issue.

“It’s a huge deal,” Ricker says, after telling me me that every messenger he knows has had either an entire bike or at least a wheel stolen. “You can potentially lose your apartment because some crackhead steals your bike.”

All of this fails to bother Michelle Willcox, a new rider who moved out from North Carolina, partially to work at TCB. She is excited to make her first run.

Ian offers advice: “Super pro move: always carry a fucking sharpie on you and when you get a bag, write the address on it.”

“Wanna know what’s insane?” asks Ricker. “I took 5 [orders from Jay’s Cheesesteaks] at once yesterday, I didn’t do that at all, and I got every bag right, just off of memory and tetris,” he adds, referring to the practice of arranging orders in their messenger bags.

“Yeah, bag tetris is real as fuck, dude,” says Ian. But “seriously, just write the addresses on the bags,” he tells Willcox.

Another piece of advice: always put the heavy deliveries on bottom, even if it’s your first drop, Ricker says.

Willcox appears to take it in and pushes off – entering into what Christiansen says is more than just a job.

“For a lot of people it’s a lifestyle, it’s a culture,” he says.

Part 1: SF Weather and Pay Lures More than Tech Workers

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