Jake Kenney, owner of the North Philly bike shop Cycles PHL, is standing in his store, remembering one of his worst days on the job. Not his job at the shop. He likes that one. He’s talking instead about his old side gig.
“The whole app-based thing,” Kenney trails off and kind of laughs. “Yeah, the app crashes, and you’re sitting on a corner when it’s 20 degrees out, and you have no idea where your food is going, and you can’t even call them because everything is shut down.”
Kenney was a bike deliverer for Caviar, a San Francisco-based company that debuted in Philadelphia in 2014. The main draw of the service is that users can choose from a variety of restaurants, tap out an order on their phones, and have it brought right to their doorsteps — even if the eatery in question doesn’t have an in-house delivery option. Crave some disco fries from Alla Spina, or guacamole from El Vez? A Caviar employee can deliver it to you.
As Kenney tells it, the job often involved freezing his ass off while the app sputtered and the food got cold.
Caviar numbers among a host of similar app-based delivery start-ups that have boomed in cities across the U.S., including Philadelphia. And much like the car-for-hire juggernauts Uber and Lyft, these companies rely on freelancers to exist. In fact, they have no full-time delivery people on the ground.
That’s pretty much the point. Postmates, which launched in Philly only a few months before Caviar, says in its mission statement that it not only wants to help customers get delivery from their favorite spots, but also to empower employees with the flexibility to work on their own terms, choosing their hours and which orders to accept. On its application webpage, the company tempts potential employees with the promise, “Earn up to $25+/hour on your own schedule!”
Caviar operates similarly to Postmates, but with a slightly upscale M.O. The app only works with certain partnering businesses — including those owned by famed restaurateurs Mark Vetri, Stephen Starr and Jose Garces — whereas Postmates touts the convenience of “delivery from anywhere.” (In parts of San Francisco and New York, Caviar also offers Fastbite, a specialized service where users receive curated meals from their city’s top restaurants.) You may have seen Caviar’s cyclists zipping around Center City with boxy orange thermal bags on their backs.
These cyclists, and others — drivers, motorcyclists, anyone with a set of wheels — employed by delivery apps, represent a new breed of worker. Just like drivers for Uber and Lyft, their work hours, and wages, are entirely up to their own motivation and schedules. But the promises of freedom and flexibility sometimes clash with the limitations of each company’s system and each employee’s needs.
Patricia Madej, a recent college graduate in Philadelphia, saw Caviar’s loose structure as an opportunity to work around her busy life. She delivered for the company until she got a full-time job.
“Working as an independent contractor was perfect at the time because that’s what I was looking for,” Madej, 22, says. “You could make your own hours, you didn’t really have a boss to report to, you could also make as much or as little as you wanted. But I don’t see myself doing that long-term. It just really worked for the situation I was in.”
Because of the independent nature of the job, many use it as a way to make a little extra scratch between school semesters or to supplement income from a day job. Tom Hope, 36, saw it as a way to help pay the bills during the off season. His full-time gig is with a private tour company, where he does walking tours of historic areas in full Colonial-Era costume. “I was like, ‘Why not?’” he says. “It’s pretty easy to get into.”
But all this flexibility puts you at risk of being expendable. As in other industries, companies have very little incentive to keep independent workers on. That’s especially true when the company benefits from a seemingly endless revolving door of labor.
“You were very replaceable, for sure,” Madej says. “There was always someone jumping at the chance to do it because it sounds dreamy.”
The job often involved freezing his ass off while the app sputtered and the food got cold.
Kenney, the Cycles PHL owner, spent time as a Caviar courier to make ends meet while his business got off the ground. Surrounded by the bikes, gear and grease of his shop, he remembers his time delivering food to the hungry masses.
“I think they don’t expect much of you,” he says. “But they also can’t really offer you any business incentive. They can’t offer you benefits, they can’t reimburse you for bike parts or repairs. All kinds of stuff.”
Hope calls it a give-and-take relationship. “I’m an independent contractor, so I don’t get the same kind of benefits that a [full-time] employee would,” he says. “But at the same time, I’m not obligated to work when they want me to, you know what I mean?”
Angela Hallinan is an operations manager for Postmates, handling the company’s emerging markets in cities like Pittsburgh, St. Louis and San Antonio. She says that while the business depends on labor from private contractors, it’s not as if they don’t have a place in the company.
“They are independent contractors,” she says. “They’re on 1099s. They’re their own boss. They can accept and reject whatever they want.”
Both Hallinan and April Conyers, senior director of communications for Postmates, point to a specific case where an employee in San Francisco started as a deliverer and worked his way up to a management position. It bears mentioning, though, that this employee started early in the company’s history, benefitting from its small size at the outset.
“He was one of the first Postmates when the company got started, so he worked a lot with the CEO and had direct contact with the CEO as the company grew,” Conyers says. “He ended up joining the company a year later.”
Nowadays it’s far less likely that new employees will have that kind of connection to the Postmates management, but it doesn’t mean there’s no room for growth within the company. “I’ve definitely interviewed couriers for specific field manager positions,” Hallinan says.
“You were very replaceable, for sure.”
So while there’s hope for those looking to create a more substantial work life from freelance bike delivery, Kenney isn’t sure that the majority of employees would need or even want that. “Caviar is a more transient thing,” he says. “People do it on the side. It’s not really their full-time gig a lot of the time, so I’m not sure it would really work.”
And while Uber drivers in New York City have established a guild to represent their interests to management, it’s unlikely that we’ll see similar efforts to organize among freelance deliverers any time soon. “I don’t know that [a union] would be necessary,” Hope says. “We’re all independent contractors, so if we all went on strike, they could just hire new people.” (Meanwhile, Uber has incorporated food delivery into its business model, launching the standalone app UberEATS last year. )
Conyers agrees that the platform works best for people looking for supplemental income, not a long-term career. “It’s probably not realistic [as a full-time job],” she says. “We don’t have too many people who deliver on the platform full time. It’s more of a, kind of, extra income.”
In other words, you might be able to make $25 an hour working for Postmates or Caviar. But you probably won’t.
For the most part, Jake Kenney looks back positively on his time pedaling for Caviar. He does have one major complaint, though, and that was with the app itself. Whenever it crashed, he would feel stranded with quickly cooling food and no idea where his delivery was supposed to go.
“It happened badly once while I was there,” he says. “I was on a corner in Center City, and it was literally 20 degrees out. The servers were down, so I didn’t know where I was supposed to go, and I just had to wait for 30 minutes.”
Hope agrees that the app could be finicky, but says it wasn’t a complete disaster if something went wrong.
“I’ve had some issues here and there,” Hope says. “Sometimes an order gets messed up at a restaurant and you’re just sitting around. Or, like, soup spills in your bag. The one thing I will say about Caviar, at least, is they have a dispatcher. So it’s not all automated. If something goes bad, I can text them. And they’re generally pretty responsive in terms of getting back or trying to find solutions.” (Postmates, too, has a number couriers can call if they encounter a problem.)
“Caviar is a more transient thing. People do it on the side.”
By focusing pretty much all of their business on a smartphone interface, app-based delivery companies set themselves up for technical difficulties that can interfere with the whole operation. Traditional bike messengers, who ferry documents all over the city for legal and architectural firms, don’t really have that problem.
Which raises the question: Are the new companies stepping on any toes?
Like many local bike messengers, Mikey Thomas, 22, hangs out in Rittenhouse Square between jobs. He doesn’t see Postmates or Caviar as a threat to his work. If anything, he might look into making it a side gig.
“I do legal work, and they do food,” he says. “At the same time, I respect Caviar. People are out here biking and making money. I thought about working for Caviar, too, because it’s not as busy with legal work… If the money’s good, I’d do it full time.” ◆
Illustration by Hannah Agosta