Analysis: Without Andrew Mason, Groupon’s Got a Whole New Deal

Andrew Mason has been ousted as Groupon CEO.

It's about time. 

I’ve been covering Groupon since Inc. Well started two years ago and, honestly, this was a long, long time coming. No one was ever actually rooting for Mason’s head to roll, but it was pretty astonishing how long he was allowed to stay on as the company continued to plummet, tank and scorch and burn.

I have been feeling for a long time now that Groupon was keeping Mason on as a sort of scapegoat in waiting — that they’d give him the boot as soon as things got their absolute worst so they’d have someone to pin it on and use him as a figure to depart from. Unsurprisingly, the release of Groupon’s quarterly results on Wednesday, in which the company’s shares dove a whopping 24 percent, was the final blow.

There’s little sense in making wild predictions about where Groupon will go from here, because most likely the new interim co-CEOs Vice Chairman Ted Leonsis and Co-Founder Eric Lefkosky will be boldly announcing where the company will head from here. But Groupon’s time of being conservative are obviously over. The company badly needs a Hail Mary, and the time is clearly now.

It was clear before I was hired on at Inc. Well that Mason’s time at Groupon had a fairly limited shelf life. It wasn’t a matter of if he’d be fired, it was a matter of when. With Mason at the helm, the company could never really mature past being awkwardly charming (heck, his farewell letter to employees spends far more time comparing his career arc to tough-as-nails video game Battletoads than specific obstacles), and after its IPO, the deals continued to get less and less interesting, service started to suffer globally and there was just a sense the company was expanding far too much.

Mason, who infamously uploaded videos of himself doing yoga in his underpants and being photographed with cats or telling stories about bringing a pony into the office as a gift for New York Mayor Michael Bloomberg, never was able to quite mature into the role of a CEO. He cut his hair, he started dressing better but much like the company he ran, underneath is was still bumbling along.

I say this not to be mean, but it’s a good thing Mason likely still has his job at that undisclosed Japanese restaurant in the city ostensibly as research for Groupon’s POS services. Jobs are very tough to come by in this economy, and while he never grew into being a proper CEO, perhaps Mason’s legacy is that he is able to cook up and execute slick ideas that people will gravitate towards. But growing a business? That’s not for Mason.

Whether the break-up (and Mason was fired, as he admitted in that aforementioned note to Groupon employees) was amicable is immaterial because, in all honesty, it’s the savviest move for both parties. Mason helming Groupon was a lot like an unhealthy relationship that went on far too long. They wanted to stay together because they had a good thing going in the beginning. But that was nearly five years ago.

Half a decade later, though, this could be just the thing to turn Groupon around and perhaps a shaken Mason, who now understands that the studying data to better serve their customers (which he said was his downfall), will use that knowledge to lead him to starting the another Big Thing in Chicago. And that, really, was Groupon’s best gift to Chicago: It put us back on the map. And now it's time to chart a new course, which isn't necessarily a bad thing.  

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. His first career aspirations were to be a game-show host.

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