“I used to be hot stuff”: Groupon’s Andrew Mason contemplates the future

Groupon’s Andrew Mason sat down with Henry Blodget last week at Business Insider’s Ignition Conference to discuss whether he’s still the best person to lead Groupon, the quirky coupon empire whose stock dropped 80 percent since its IPO. The interview left a lot of reporters wondering if Mason’s days at Groupon really might be numbered, and a few of us remembering a time when Groupon was synonymous with new opportunities.

A pitfall of the world of entrepreneurs and big ideas is that you have to invest emotionally (beyond the financial bid) in the notion that somebody unconventional can create something truly spectacular and profitable. Groupon changed how people in all tax brackets bought gifts and planned for experiences. It changed (for better, and sometimes worse) how small businesses attracted customers. For some of us, Groupon changed how we thought of employment–more on that in a minute.

So to see a man once so secure in his entrepreneurial greatness that he chugged beer at a company townhall meeting about poor performance and serious accounting errors contemplate his former “hotness” feels a bit like being told you’re all grown up, dreams aren’t real, and you’re going to be paying full price for your avocado facials from now on.

Groupon burst onto the scene when I was living in Chicago as a recent college-grad and immediately became a huge part of my life–and everybody else’s–both as the only way I managed to afford doing things like kayaking the Chicago River during a nighttime fireworks display and as a place I was just maybe dying to work. It ushered in a pre-Chicago-based-Onion era when the Groupon Careers page was bookmarked on all of our homepages.

Recent Second City and Improv Olympics grads, people writing web content from their childhood bedrooms for pennies a clause, actors doing live product demonstrations at Macy’s, and those of us slogging through sputtering freelance careers and maddening marketing/comm jobs clamored for the salary, health insurance, and work-from-home-Wednesdays the company promised those capable of pounding out enough deals for Scranton and Poughkeepsie to meet a strict daily quota.

A New York Times profile of the Groupon work environment immortalized it as a place where aspiring poets circulated their work in the lobby. Sam Weiner, a writer who had previously worked at a kennel, provided the crown jewel of quotes: “‘My dream,’ says Mr. Weiner, 26, ‘was to get a job writing comedy and make more than minimum wage watching dogs die.'”

Deliberately or not, Groupon created not just a couponing empire, but a place where young writers could (gasp) work for money.

But after whispers last week that the young CEO might be on the chopping block, Business Insider’s Jim Edwards reported that Mason “emerged unscathed from a meeting with his board of directors Thursday around which there was speculation he might be fired.” A paragraph at the end of Edwards’ analysis seems written precisely for those who want to believe in odd men with good ideas:

“Groupon is Mason’s first real job. He didn’t have CEO experience before this. He’s an unusual guy. The company now has 12,000-plus employees. Which means it’s only normal for board members to ask whether the company might be better off with a more seasoned executive. That notion is as old as the company itself. And it ignores the Mason-[Executive Board Chair] Lefkofsky relationship. And it ignores the fact that Groupon, despite (or because of) its weirdness, is a success.” 

Groupon’s stock has been making moves in the right direction this week. If it continues to rise, investors may go on betting on the “unusual guy” who’s a first-time CEO, and Mason may be able to crack open another cold one.

Bonus: Henry Blodget and Jim Edwards have a gentlemen’s disagreement in the comments section of Edwards’ post.

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