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Goodbye Groupon: Andrew Mason's dance with the devil

Goodbye Groupon: Andrew Mason's dance with the devil


An aspiring entrepreneur partners with an experienced operator with a checkered past

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Groupon co-founders Eric Lefkofsky and Andrew Mason
Groupon co-founders Eric Lefkofsky and Andrew Mason

In the wake of Andrew Mason's firing as CEO of Groupon, there's been a lot of negativity towards the young entrepreneur. In part it's because Mason was always a character, someone who largely refused to take things seriously, and who preferred to defuse tension with humor, as he did in his hilarious resignation letter yesterday. This was charming at first, then increasingly less so as Groupon's financial health, business practices and accounting came into question. But as the smiling face of the fastest-growing company in history, Mason was also a shield, a barrier between the press and Eric Lefkofsky, the co-founder and investor behind Groupon, and a man with a track record of creating hypergrowth companies that have crashed and burned... after he cashed out.

Mason was an unwitting shield, a barrier between the press and Eric Lefkofsky

My mother knows who Andrew Mason is — he was the poster boy for Groupon and a frequent presence in the media. Far fewer people, even among tech investors, are familiar with Eric Lefkofsky. That's a shame, because once you become familiar with his history, it's stunningly clear what happened with Groupon.

Groupon_stock_chartGroupon stock chart via Yahoo Finance

The best reporting on Lefkofsky comes from this Fortune magazine piece, which was published a few months before Groupon's IPO. It traces his history as a Janus-faced business man, someone known as both "the most successful and prolific internet entrepreneur in Chicago," but also as a man with "a history of busting investors after promising to radically transform bricks-and-mortar industries."

Lefkofsky's first venture was Brandon Apparel, which he himself noted "ended up being a huge failure. We over-leveraged the company and it eventually crumbled under the weight of that debt." It's honest of Lefkofsky to acknowledge his failures, but the closing of Brandon was much messier than that. Lefkofsky was sued by his bank, which won an $11 million judgement, leading Lefkofsky to then sue his law firm for malpractice. The former owner of Brandon also sued, as did the NFL and MLB, and the city which loaned Lefkofsky money to build a new factory.

Lefkofsky's first venture was Brandon Apparel, which he noted on his own blog, 'Ended up being a huge failure'

His next venture, Starbelly, was launched during the heady days of the dot-com boom. Again, Lefkofsky raised a lot of capital, this time taking millions in venture funding. In January of 2000 Starbelly — still less than a year old — was sold to Ha Lo, a 50-year-old company, for $240 million. By the end of that year, Ha Lo had gone from profitability to a huge $64 million loss, largely thanks to $48 million in costs accrued from the acquisition of Starbelly. By 2001 Ha Lo had filed for bankruptcy, and numerous lawsuits were again filed with Lefkofsky's name on them.

Lefkofsky's next two ventures, a print-procurement service called InnerWorkings and a supply chain management firm named Echo Global Logistics, showed that perhaps his ways had changed. Both went public and have remained in business.

But with Groupon, a familiar playbook resurfaced. When Lefkofsky met Mason, the latter was a young, ambitious entrepreneur working on his first company, a crowdfunding platform called The Point that was similar to Kickstarter or IndieGoGo. Lefkofsky saw something in Mason, and gave him several hundred thousand dollars to grow The Point. But after a few months, Lefkofsky became impatient. As Mason told Chicago Magazine, Lefkofsky "started prodding me to figure out how The Point was going to make money." Eventually The Point pivoted to become Groupon, with Mason as the brash young CEO, and Lefkofsky behind the scenes, controlling a huge percentage of the shares and voting rights.

With Groupon, a familiar playbook resurfaced

Groupon went on to become the fastest-growing company of all time, hitting a billion dollars in revenue in just 17 months. It followed the Lefkofsky playbook to a T: a hypergrowth company fueled by mountains of investment capital that claimed to be reinventing an old industry — coupons and loyalty cards — with a high-tech approach. In an interview with Bloomberg before the company went public, Lefkofsky claimed Groupon would be "wildly profitable", a statement the SEC later forced him to retract. And while a few journalists raised questions about Lefkofsky's past, most focused instead on the incredible growth and the smiling Andrew Mason, who personified the disruptive youth and innovation of a startup.

Since it went public, the facade of Groupon has come tumbling down. Instead of wild profits, there's been steady losses. And as the red ink has mounted, so have the lawsuits, from investors who said they were misled and from employees who said they weren't paid. The SEC was forced to look into some very fishy accounting which appeared to have been used to prop up Groupon's books. As the bad news piled up, Mason took the brunt of the criticism, with Lefkofsky fading into the background.

Just like his previous ventures, the fall of Groupon had less of an impact on Lefkofsky than many others

With Mason's departure, Lefkofsky will take over as co-CEO, along with vice chairman Ted Leonsis. In some respects that will mean he finally has to face the music. But just like it was with his previous ventures, the health of Groupon's business has less of a material impact on Lefkofsky than many others involved. He and his family actually cashed out to the tune of $382 million before the IPO taking a huge chunk of cash off the table during the last round of venture funding. Insiders cashed out again during the IPO, which valued the company at $12.8 billion. And it wasn't long before talk of a secondary offering, which would allow insiders to cash out for a third time, began to swirl.

In the 16 months since Groupon went public, the stock has plummeted more than 80 percent. It's now worth $3.09 billion, or roughly half what Google offered to pay for it back in 2010. And its most recent earnings, reported yesterday, paint a grim picture, with the company notching losses of 12 cents a share.

Andrew Mason quipped in his goodbye letter that he's taking a break, go to "fat camp", and maybe lose the "Groupon 40", before diving into something new. But as he looks to begin the second phase of his career as an entrepreneur, he will have a reputation to shed. As Mason himself wrote in his goodbye letter:

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 — I was fired today. If you're wondering why... you haven't been paying attention. From controversial metrics in our S1 to our material weakness to two quarters of missing our own expectations and a stock price that's hovering around one quarter of our listing price, the events of the last year and a half speak for themselves. As CEO, I am accountable.

Mason certainly made his own decisions and he leaves Groupon a richer and more well-known man than most. He made far less money on Groupon than Lefkofsky but he certainly did well: Mason took roughly $10 million off the table during the last venture round and no doubt sold some shares after the IPO. In return, he's been labeled tech's enfant terrible and a terrible CEO. His name will forever be associated with a company that flopped on the markets, fudged its financials and generated an unsual amount of lawsuits and hatred from investors, employees, consumers, merchants and the media.

And that's too bad. Because Mason was played. He got a fraction of the benefits and the lion's share of the blame when compared with his co-founder. As Crain's Chicago Business points out, "Mr. Mason also has control over 20 percent of Groupon's voting shares. Mr. Lefkofsky owns 20 percent of the stock but controls 28 percent of votes, thanks to a two-tiered stock structure. His longtime business partner, Brad Keywell, controls another 10 percent of the voting shares. Together, they easily trumped Mr. Mason."

Mason was an ambitious young entrepreneur who got into bed with a man who's run a very dirty game many times before. And once the rocket ship took flight, it was no doubt very difficult to get off before he was unceremoniously shown the door.