In 2010, the sun had set on the aughts, the economy had atrophied, and a whole lot of people were out of work. A freshly minted class of college graduates were entering a recession-era workforce characterized as the worst job market in a generation. It was a dark time. Extreme couponing had become an dystopian sport broadcast on TLC, and even our viral videos came with depressing capitalist undertones.

Then, from the ashes of recession-era economics, an unlikely hero arose. Old-school, Savvy Shopper-style discounts got a techie makeover, and suddenly, coupon-shilling startups — LivingSocial, Groupon, and a seemingly endless swarm of store-brand knockoffs — were sprouting up from the recession’s rot like toadstools. In August 2010, Forbes reported there were more than 200 daily deal companies in the U.S.; by 2011, that figure would more than double. Coupons, the media crowed, had become cool.

In hindsight, the daily deal industry represented the kind of ludicrous bubble that kneecapped early dot-com companies like Lycos and Geocities just 10 years before. But for a brief, dazzling moment, the Coupon Industrial Complex was meteoric. It had a lot to do with timing, J.P. Eggers, associate professor at NYU’s Stern School of Business, told The Outline. In the thick of the recession, companies like Groupon promised to offer cash-strapped consumers a way to save money and to drum up foot traffic for ailing brick-and-mortar businesses desperate for the kind of spending that the recession had made so scarce. “They had a good sales pitch,” he said.

They also gave a whole lot of overeducated, underemployed, and loan-saddled millennials a shot at actually making rent. Writing copy for vajazzling coupons wasn’t quite the same as netting an editorial assistant gig at Condé Nast or making it as a comedian, but it paid the bills. And among Chicago’s talent pool of job-hungry comedians, actors, and creatives, who had gravitated to a city that offered some of the resources of New York at a fraction of its cost of living, Groupon — the most popular of all the coupon startups, headquartered in Chicago — offered an instantly symbiotic relationship.

Patrick Masterson arrived in Chicago as a college grad in 2007, one year before the economy officially shit the bed. Chicago, he reasoned, would be a welcome cultural change from the South, where he grew up, but more realistic than New York, where the cost of living had become astronomical. He worked in the sales department of an ailing publishing house until 2010, when he was laid off shortly before the company declared bankruptcy. Some of his former coworkers landed at Groupon, and Masterson figured it was worth a shot. He applied, and was hired as a fact-checker in January 2011. “I had no idea how long any of it would last,” he said.

Like Masterson, Daniel Cox (whose name has been changed here because he’s currently job-hunting) also entered the industry coming from less-than-ideal employment circumstances — or, in his words, a “shitty temp job at a call center.” A few friends of his had recently jumped aboard the Groupon bandwagon, so he figured he’d try the same. He was brought on in late 2010 as a Quality Assurance Specialist, which meant he double-checked things like fine print before deals went live. “I was really excited to get the gig,” he said. Groupon was “the darling of the tech industry” at the time, but it was also just an honest-to-god income — hard to come by in those days. “It was the first job that paid me an actual salary and gave me benefits,” he said. And, he added, “It was a great job to work at during the day while pursuing your artistic passion at night.” (His, like so many of his Groupon coworkers in Chicago, was theater.)

“If anyone who was under the age of 27 and living in Chicago in 2010-11 tries to tell you they didn’t apply there, they’re lying.” — Patrick Masterson

Another Groupon employee, Alex Bean, joined in January 2011 after completing his master’s and spending one semester teaching as an adjunct. “I applied to Groupon because I knew they were hiring creative/writing/academic types in droves,” he said. Groupon was, as it was for Cox and for so many of their peers, Bean’s first full-time, benefits-included, “real” job.

I was one of them, too: after stringing together an income out of contract work by day and graveyard shifts at a dog kennel by night, I felt fortunate to get a job writing pun-riddled copy on discount deals for suburban pizza joints, strip mall sushi restaurants, and spray-tan booths for an Atlanta deal startup called Scoutmob. I joined the company shortly before it moved out of the founder’s basement. Like Groupon, albeit on a smaller scale, the company quickly earned local “tech darling” status in our city. (No, really: a few months after I started, our city magazine published a 4,000 word profile that used the word “darling.”)

Groupon’s headquarters were festooned with all the trappings of stereotypical startup life: a LaCroix-stocked fridge, a ping-pong table, balance balls for chairs, regular free lunches, and unlimited vacation. Absurdity snuck into every aspect of the workplace; potential candidates were asked to draw self-portraits at their own job interviews, and teams were named after Jean-Claude Van Damme movies. “Everything was themed with cats because that was the mascot,” Masterson recalled. “You know. Of the internet.” He described the general atmosphere — in the beginning, at least — as one of unbridled excitement, with each day bringing a new challenge, a new structural upheaval. “Coming from a job where it felt like time stood still for three years,” he said, “living Groupon’s changes was invigorating to me.”

In an arid wasteland of jobs, Groupon and its imitators were like desert oases for income-thirsty 20somethings, especially white ones. In May 2011, a 3,000-word story in The New York Times about Groupon followed the making of a deal for horseback riding lessons as it shuffled along a conveyor belt of young people, from a 23-year-old English major writing the copy to the 25-year-old assistant theater director-turned-fact-checker to the 27-year-old Second City alum who gave it the final edit. “In the age-old tradition of creative folk, they were just looking for a gig to support their art,” the Times wrote. “Now stock options have made some of them seriously wealthy, at least on paper.” (Mere months later, headlines would tell a wildly different story.)

As Groupon swelled, so too did its ranks. A year after Forbes had crowned it the fastest-growing company in history, Grouponers were some 8,000 in number, and they were everywhere. Cox recalls seeing the company’s souvenir jackets, which the company doled out to employees on their one-year anniversary, practically every time he left the house. “It was so odd to be in public somewhere and just see random people wearing green Groupon track jackets and knowing they worked at the same place you did,” he said. Andi Mitchell, whose name has been changed here because her current job limits her from speaking to the press, was unemployed before joining the company in 2011, says that at one point “it seemed like half the comedians in town worked there.”

At the office, Masterson bumped into people not only from his old job, but also from the radio station where he volunteered. “If anyone who was under the age of 27 and living in Chicago in 2010-11 tries to tell you they didn't apply there,” Masterson said, “they're lying.” In November 2011, Groupon debuted their IPO, priced at $20 per share, closing at $28, raising $700 million, and setting the record at the time for the second-biggest tech IPO in history.

Workers work on projects at Groupons international headquarters in Chicago.

Even if you weren’t sold on changing the future of commerce, the social side of working with hundreds of young, smart, funny people kept things interesting. “It was like a continuation of college and grad school,” Bean recalled. In my own experience, that translated to tons of company-sanctioned binge drinking, one slimy senior-level salesman who foisted himself on younger female coworkers with what we called Creepy Colleague Shoulder Massages, a blow-up doll dangling from the ceiling above the sales pod, and for most of the company’s history, no designated HR professional. What could possibly go wrong?

Of course, that kind of growth — the kind that makes dollar sign symbols pop out of investors’ eyeballs — never lasts. As the industry ballooned and bloated, companies like Groupon began to sag beneath its own weight, and working there started to lose its luster. “Teams grew and shrank and grew again,” says Cox. “No one seemed to really know what to do with a company of this size other than to keep expanding.”

The confetti-showered opening bell rung by Groupon’s CEO that November morning now feels more like a death knell. Today, a share of Groupon is worth about $5, and Groupon’s formerly record-breaking IPO is no longer even in the top 10. It didn’t matter at the time, Bean said. “We all knew this was weird and unsustainable and that we would see few fruits from all this labor, but we were also young and along for the ride.”

Hundreds of new employees were hired each week, and roles were messily shuffled, redefined, and combined. Meanwhile, the myriad clones and competitors began dropping like flies. Even CEO Andrew Mason himself got canned eventually, a mere two years after taking the company public. Seemingly as fast as its meteoric rise, Groupon’s deal emails were left to wither in spam folders, and spotting those green track jackets in the wild wasn’t quite so common.

Eggers chalked that swift demise up to the fact that, in the race for signing up merchants, salespeople began to ignore one very important thing: quality. The relentlessly aggressive sales force started going after a lot of sub-par merchants, and at a certain point, most of the businesses signing up were the ones already struggling. A Groupon deal became a last-ditch effort to survive, when in reality it was more of a funeral dirge. Deal quality suffered. “It was fun for a while, then everyone got tired of checking because deals were lousy and nobody wanted them,” Eggers said.

Today, the daily deal company format is technically still around, but it has more cultural relevance as a Broad City backdrop than as the behemoth it once was. Less than a decade after Groupon turned down a $6 billion buyout from Google, the idea of eagerly checking your inbox each morning for a half-off coupon at your neighborhood pizza joint seems like as much a charmingly throwback cultural relic as an AOL email address. People still work at Groupon, but the company and its counterparts are what Eggers categorizes as “the living dead:” zombie-like organizations that don’t see any new influx of cash and are just stumbling along. “There’s no longer any real expectation of long-term growth attached to the company at that point,” he explained. (In other words, not even Tiffany Haddish can save you.)

As for the employees who hitched their wagons to Groupon’s star during peak coupon frenzy? Well, Masterson fulfilled his dream of becoming a copyeditor. Bean is a media studies professor at City Colleges of Chicago. Cox stuck it out until he was laid off alongside 100 of his colleagues last year; he’s now a freelance editor. Mitchell writes for a television show. She also attributes much of Chicago’s current comedy scene to the jobs Groupon doled out. “Groupon may not have turned out to be as successful as we all thought,” she said, “but there are a few television shows and movies that wouldn’t exist without the support the company provided the comedy community.”

They look back on their rollercoaster ride at the front lines of the bubble with a mix of nostalgia, bewilderment, and gallows humor. For all its shortcomings — the short-sightedness of it, the whirlwind pace, the absurdity of crafting compelling sales copy for things like this — there was also nothing quite like it, said Masterson. “For a little while, at least, it was a really special place to be.”

Get The Outline in your inbox Subscribe The NSA will be in touch.