Groupon's First Copywriter Says, 'We were a Scrappy Startup, Just Having Fun'

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Founded in 2008, Groupon is among the first and most successful companies to offer daily deals on goods and services from pedicures to wine tastings in cities across the U.S., Canada, Europe and, if you believe their “About” page, “soon beyond (read: Space).” The ad copy on this site raises the question, would Groupon’s clients really be willing share their discounted gym memberships with space aliens? And how, exactly, did online coupons become a platform for publishing fiction? Groupon’s first copywriter (and helmet-wearer), Aaron With, gave Mediabistro Startups the details.

Before he was Groupon’s editor in chief, With had been the community manager of The Point, a fund raising site founded in 2007 that spun off into Groupon in 2008. Like anyone else working for a startup, With had to be flexible to get the group discount site off the ground.”I didn’t have a writing background,” he said, but when it came time for Groupon to run its first deal, With volunteered to write the copy for the landing page, reasoning that “it looked like fun.”

At the time, the company only had about 500 subscribers compared to the 1,000,000 they reported in fall of 2009. “In the beginning we had no idea anyone was ever going to read this,” With said. “We were a scrappy startup, just having fun.”


With started experimenting to see what worked and what didn’t. “We made a few mistakes in the beginning,” he said, but With found that most merchants were “pleasantly surprised” with the results. “If you’re going to do anything creative, you’re going to risk alienating somebody,” he added.

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“Over time we figured out this style of humor that worked really well and that we liked writing,” With said. The Groupon voice is a surreal blend of storytelling and word invention. Today’s $20 voucher for $40 worth of Mexican food and drinks at Sueños in Manhattan comes with instructions to “marinate your tongue in a cooling south-of-the-border specialty cocktail” in the event that “all the spices accidentally give you the power to fold space.” Even the company’s customer service department has a written policy against “transfer-athons.”

“Aside from satisfying our own creative whims,” With said, “it actually ends up making good business sense, too.” According to With, the customers reported that they read the write-ups even when they weren’t interested in the deal. Added With,”it’s our feedback from customers that really gave us the confidence that this is something awesome that we needed to keep doing.”

Now that the company has grown, the biggest challenge for With is keeping the style consistent. “We’re writing enough copy to fill a 190-page novel every day,” he said. It’s difficult “maintaining that kind of excited vibe and ownership.” Today Groupon updated a query for freelancers on our job board, but With said that most of their writers work in-house at their headquarters in Chicago. “We’ve had a lot better luck with full-time writers,” he said. Overall, Groupon has more than 300 employees and a growing second office in Palo Alto, CA.

Applicants should take a look at Groupon’s Style Guides for Details and Voice. “We try to coach writers on the kinds of humorous tangents that really work in a Groupon write-up and what kinds of things don’t,” With said. “We try to define it as much as we can, but not in a way that inhibits writers. We want new writers to come on and help evolve and grow their voice and make it their own. So we try to give them guidance without really restrictive rules.”

It helps that the company’s founders, Andrew Mason, Rob Solomon and Ken Pelletier have created an environment that lends itself to creativity. “A lot of the leaders in this company happened to have some other creative outlet in their lives – from music, to comedy, to writing,” With said, “so there’s a lot of people here with pretty good taste.” With balances his work schedule by playing guitar and singing in a Chicago rock band called Volcano. “What I’ve learned about writing [at Groupon] has helped me as a lyricist,” he said.