It would be exhausting to fully catalogue the missteps of Groupon, the Chicago-based daily deals site that launched in 2008, which at last culminated in the dismissal of founder and C.E.O. Andrew Mason yesterday. “I was fired today,” Mason wrote in a letter to Groupon’s ten thousand employees. “If you’re wondering why… you haven’t been paying attention.”

Under Mason’s watch, Groupon did manage to become, according to Forbes, “the fastest growing company ever.” But even a truncated list of the company’s failures borders on breathtaking: when it raised just over a billion dollars in funding over the course of 2010 and 2011, nearly nine hundred and fifty million found its way into the coffers of Groupon executives and stockholders rather than being used to fund the company. In late 2011, shortly before it went public in the biggest I.P.O. since Google’s, it was forced to cut sales estimates, boosted through aggressive accounting practices, by more than half. Nonetheless, its initial valuation was almost thirteen billion dollars. Just months later, an audit by Ernst & Young revealed “material weakness in [Groupon’s] internal controls,” leading it to revise the earnings report of its first quarter as a public company—the revised report reduced its income for the quarter by $22.6 million. And for its most recent quarterly earnings results, announced the day before Mason’s departure, Groupon reported a loss of $81.1 million.

Groupon became an emblem of what many have characterized as a bubble in Silicon Valley as questions about the fundamental soundness of its business model followed its seemingly boundless growth. Shortly after announcing its I.P.O in June 2011, CBS News offered “Why Groupon Looks Like a Ponzi Scheme,” while TechCrunch explained “Why Groupon Is Poised for Collapse.” By that October, Andrew Ross Sorkin wondered how Wall Street missed the “warning signs.”

But the picture of Groupon in the press has been complicated because Mason is the kind of founder that the tech and startup press loves—direct, goofy, a little outrageous, the embodiment of his company. Kara Swisher, reporting just a few months ago that Mason was on the verge of being fired, characterized him as “thoughtful and affable” as well as “the heart and soul of Groupon’s quirky culture and innovative product strategy.” Mason has come out on top in more than one lengthy profile, thanks to moments like the time he intended to give Michael Bloomberg a pony, or when he announced Grouspawn, a service with a $60,000-a-year trust fund for children born to parents who met on a Groupon date. When asked for a funny quote for a headline, he told a reporter, “Unfortunately my commitment to our business is still marginally higher than my commitment to fucking around.” He does yoga in his underwear. Even the letter he penned to employees, announcing his departure from Groupon, was met with acclaim—“After four and a half intense and wonderful years as CEO of Groupon, I’ve decided that I’d like to spend more time with my family. Just kidding.”

Groupon co-founder and chairman Eric Lefkofsky is taking over from Mason until a permanent replacement can be found. Will he be able to salvage Groupon? His history offers little consolation for investors or, perhaps, Groupon’s ten thousand employees: the most extensive piece of reporting about Lefkofsky is a Forbes profile from 2011 that details his “checkered past” of failed companies and shareholder lawsuits. (And of the hundreds of millions of dollars of investor money that fell into the pockets of Groupon executives, over three hundred and eighty million went to entities co-owned by Lefkofsky and his wife.)

And while the tech press, particularly publications that focus on tech startups and Silicon Valley, is essentially enthusiastic—when Instagram was acquired by Facebook, the most well-read chronicler of Silicon Valley, TechCrunch, altered its logo in homage—it also seems unlikely that Lefkofsky will be able to provide the kind of cushioning that Mason’s almost bubbly public personality did. The end of Mason’s letter to Groupon employees says that “this leadership change gives you some breathing room,” but the company may have in fact lost its best source of air.

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Photograph by Christoph Soeder/Redux.