Weather Updates

Head for monkey business is a must at Groupon

Updated: September 24, 2012 6:25AM

Aaron With is singing in the rain. Sporting a striped tank top and royal blue briefs, the mustachioed minstrel splashes in puddles and strikes goofy poses; he slip-slides down a grassy slope and does backward somersaults; he twirls an umbrella and dumps a jugful of water into the held-open front of his tighty not-so-whities, which hug him like microwaved Saran Wrap. Gene Kelly, by comparison, is a lead-legged bore.

The tune With is crooning, incidentally, is his own: a lyrically and rhythmically inventive composition called “Africa Just Wants to Have Fun.” He typically performs it alongside other members of his Chicago band, volcano!, as opposed to solo in his skivvies. The alfresco frolicking is part of a video that’s available for your viewing pleasure on YouTube and the group’s website. (With, dryly: “I’m sorry you had to see that.”)

Although he still writes, plays and records, With’s music lately has taken a back seat. As he has on an increasingly labor-intensive basis since 2008, the 29-year-old Northwestern alum spends most of his waking hours overseeing a burgeoning North American editorial staff (now 200-plus) at Chicago-based deal purveyor Groupon. The rapidly growing company made waves and headlines not long ago by shunning a multibillion-dollar buyout offer from Google.

But for all its megabucks ($500 million or more in 2010 revenue) and clout, Groupon remains a place where the bottom line and artistic passion intertwine — where guys like With feel right at home despite the soul-deadening presence of cubicles. In fact, as hiring ramps up and competition gets fiercer, Groupon job applicants would do well to highlight their artsiest pursuits.

“I like to hear that somebody has those kinds of interests,” says Groupon’s managing editor, Brandon Copple. “Because if you’re playing in a band or you’re acting in neighborhood theater, that shows me a real ... what’s the word? Ambition is not quite the word I’m looking for. But you get a lot of motivation. Because you’re not making any money doing that. You’re doing it because you love to do it and because you get a real thrill out of being creative and making something that’s really cool. And those are the kind of people we feel like, when they get in here, we can trust that they’ll really apply themselves to do great work.”

From entry-level scribes and senior managers to its front-desk receptionist, Groupon’s roster boasts visual artists, musicians and comedians. Improv actors, in particular, abound — many of them in the customer service department.

“It’s a starting point for people to build rapport here and to bond,” With says. “And I think it feeds into the work.”

Groupon’s artist-friendly atmosphere is old news in Chicago’s creative community.

“If you were to trace the lineage of every customer service and editorial employee referral, and list the outside accomplishments of each individual employee,” customer service rep and improviser Andrew Smreker says, “you would basically have a diagram of Chicago culture’s central nervous system.” He goes further, claiming that “every person in every Chicago scene either knows a Groupon employee or is a Groupon employee, and everyone has at least applied.”

There’ve been some notable breakouts, too, including recent “Saturday Night Live” hire and erstwhile Chicago improviser Paul Brittain, who temped at Groupon in 2009, and stand-up comic C.J. Toledano, a new Conan O’Brien script intern. Onetime staffer Amanda Velez now works for Lady Gaga’s Monster Ball Tour.

“Collaboration is huge at Groupon,” says Toledano, who’s “still involved with Groupon,” via e-mail during a “Conan” break. “Everyone is constantly doing ‘bits.’ And it’s not like other work environments, where there’s that one unfunny guy who keeps trying to be funny and no one likes him, because everyone who has been hired has more than likely been referred by a friend or collaborator. Thus, they check out and their humor has been approved. I hosted and produced a late night talk show called ‘The Late Live Show’ at Second City, and I can say that about 95 percent of the writing staff is working at Groupon in some capacity. If you go to an improv or sketch show, I guarantee you would see four or five people who work at Groupon either onstage or in the crowd supporting. It’s an amazing environment that makes going to work fun. I can count so many times where I or a co-worker have said something like, ‘Man, I have tomorrow off, but all my friends are at work. I’d rather just go in.’ ”

Prior to its juggernaut days, when Groupon was a struggling startup spawned from a social and political activism site called, Smreker decided he should nix a few stand-up dates to accommodate overtime hours. When With caught wind of his plans, Smreker remembers, he was sympathetic. “You should have told me that,” With said. “Don’t cancel your shows, man.”

That sensibility is validated by, and trickles down from, Groupon’s CEO and founder, Andrew Mason. A 30-year-old graduate of Northwestern’s music program and With’s former college bandmate, Mason no longer plays public gigs but gamely banged out a couple of vintage Billy Joel tunes last month at a Second City charity event. He looked more comfortable behind the keyboard than he did beforehand, onstage, where he was playfully pelted with rich-guy queries by his pal and mentor Steve Albini, one of Chicago’s top recording engineers and Mason’s ex-boss. Mogul-in-the-making though he is, with deep-pocketed suitors and ample entrepreneurial savvy, Mason’s right-brained self dominates his personality.

“The best part of my job is to inject creativity where it’s not supposed to exist,” Mason told in May. “The cool thing about being in business and no longer being a musician is that there are so many opportunities to be weird and goofy.”

Such as his Web spoof Monkey for a Week ( Its marketing hook: “Experience the joy of monkey companionship without the hassle or commitment!”

He also once considered (seriously or not) hiring a violinist to attend company meetings and improvise a soundtrack based on the tone of conversation.

Just as incongruously for the supreme leader of a $1.3 billion business, Mason has staged inner-office performance art stunts and is given to absurdist/satiric pronouncements in a variety of media. In print, he agreed to speak with the New York Times “only if you want to talk about my other passion, building miniature doll­houses.” On television, he evaded “Today” interviewer Matt Lauer’s Google-centric questions by recounting how his middle name, Divens, spurred childhood teasing. On Twitter, he’s all over the map.

“If he wants the evangelicals,” Mason tweeted in September 2008, a couple of months before Groupon launched, “Obama needs to conceive a more tragic fetus than Palin and not have it aborted.”

And this deep thought: “Just spilled some s--- all over myself.”

The colorful and frequently zany verbiage that conveys Groupon’s heavily discounted daily deals — from mani-pedis and skydiving lessons to architecture tours and hotel stays — to roughly 40 million subscribers in more than 300 markets worldwide is the most visible manifestation of its creative core.

“Coral Reef Tanning provides a welcoming atmosphere where visitors can darken their pelts for hunting season and acquire an alluring shine for fishing season,” went a writeup that targeted the Raleigh, N.C., market. “The helpful melanin-manipulating experts at Coral Reef help customers assess their skin types and provide instruction on how to maximize each tan without leaving the earth’s atmosphere.”

It proceeded rather strangely. “Earlier, technologically inferior societies valued powdery paleness and wish-granting leeches. However, it is no secret that a smooth tan waiting to show itself off beneath a suit of armor is the modern mark of refinement.”

The “powdery paleness” line was repurposed for similar deals in Boston, Nashville, Atlanta and Los Angeles.

Text about a yoga session invited would-be participants to “stretch your connective tissues to superheroic proportions.” Doing so, it suggested, was the next best thing to acquiring preternatural strength from a “radioactive-meteorite encounter.” That’s a superhero allusion, in case you’re wondering, and one of relatively few pop-culture references to pepper Groupon’s prose.

Crafted largely by twenty­some­things who earn an average salary of 33 grand a year, reams of writing are sculpted and resculpted and vetted and fact-checked so as to assure accuracy, uphold Groupon’s vow of transparency and project its official voice. David Foster Wallace wannabes can find their own during off hours.

Some passages are more polished than others, and there’s a pleasing dearth of corporate gobbledygook and tired tropes. And while the humor that runs through it all is hit or miss (from the Groupon Guide to Vacation Packing: “Suitcases are called suitcases for a reason. That’s where suits go. Not socks. Take them out.” Groan.), it invariably serves to soften the already soft sell.

“We try to make sure our humor is as innocuous as possible,” Copple says. “We don’t want to offend the merchants who are business partners, we don’t want to offend any of our readers. We don’t do humor at anyone’s expense, and that can be challenging. Because it’s funny to make fun of people, especially when they’re jerks and they deserve it. That’s why the Onion is funny, right? Because they just beat up on people who deserve it.”

When Groupon was still scrambling toward sustainability, With says, things were different.

“On the editorial side, we were making it really difficult on sales early on because we were violating all the offensive taboos that we’ve now learned to avoid. Being too aggressively dark sometimes and making disgusting jokes in fancy restaurant write-ups — all sorts of stupid, stupid mistakes. So we’ve figured out a happy medium.”

With laughingly recalls a spa write-up that was “really dark, apocalyptic, over-the-top depressing. And, like, it was totally our fault; we messed it up. It was funny, but it was stupidly dark, totally inappropriate and the spa flipped out.” He can’t, or won’t, be more specific.

These days, though, that’s the exception. In the same vein, lobsters will never again be pitched — inadvertently or otherwise — as pets instead of food.

“People expect a certain kind of copy,” With says. “Our humor isn’t just silly or coy. It’s not traditional web sass. It’s really smart. I think it instills a sense of admiration. And I think when people read it, it speaks to them in a way that’s like, ‘Oh, somebody smart is writing this. This is weird. They’re weird like me.’ ”

Perhaps. Or it might simply mean that $20 for three hours of unlimited video games, a round of mini-golf, a game of laser tag, one personal pizza and one medium soda in Gurnee is an offer they can’t refuse.

© 2014 Sun-Times Media, LLC. All rights reserved. This material may not be copied or distributed without permission. For more information about reprints and permissions, visit To order a reprint of this article, click here.