Keep Your Face to the Sun: What’s Next for Groupon’s Andrew Mason?


F. Scott Fitzgerald claimed famously “There are no second acts in American lives.” His immanently quotable pronouncement has become conventional wisdom without much scrutiny or consideration. Although sadly true for Fitzgerald whose career fizzled after early genius, in example after example, seconds acts do occur in American lives.

Six years after telling the media in a valedictory press conference “You won’t have Nixon to kick around anymore,” he became President. After 70’s fame with Grease and Saturday Night Fever, John Travolta’s career went into a free fall before his Academy Award nominated performance in Pulp Fiction. Ben Affleck’s rise, fall and redemption were recently chronicled here. Nancy Pelosi didn’t even run for Congress until after she had raised five children. California Governor Jerry Brown in the seventies was the wacky “Governor Moonbeam” from California. Today he’s back as the parsimonious elder statesman flying Southwest Airlines without staff. Steve Jobs went into the wilderness after being kicked out of Apple.

All of which leads us to this question: What happens now in the life and career of Groupon’s Andrew Mason?

Last week Groupon, after a year of falling stock prices, ousted its CEO and founder, Mason. What had made news wasn’t his firing — CNBC had named him the worst CEO of 2012 — but the content of his letter to employees after he left.

As I read it, the letter, the hurt feelings and the general circumstances immediately brought to my mind one of the other more dramatic departures in corporate history, that of Steve Jobs in 1985.

After founding Apple, presiding over its meteoric rise and its IPO, Jobs left the company amidst declining sales and stalled development. At the time Jobs penned a public letter, sent to Newsweek that expressed his sadness and confusion by Apple’s “hostile posture” towards him. The departure was far from peaceful.

Similarly, Mason founded Groupon, presided over its meteoric rise and its IPO, which valued the company at $13 billion. He was young as well and like Jobs, a bit eccentric.

Now if I were to declare Andrew Mason as the next Steve Jobs, I think there’d probably be a mob of angry investors at my door. There’s plenty of nearly vituperative articles out there like this as well, which are representative of most of the thinking of the day.

So don’t worry, although I’ve drawn the similarities above, I won’t go that far as Mason has to earn that comparison. However, I recall years ago watching Heidi Fleiss: The E! True Hollywood Story and in a move only a Los Angeles-based attorney could make, I’m going to draw some wisdom from the Fleiss documentary.

As the narrator detailed Fleiss’ shrewd climb to being America’s most famous Madam high in the Hollywood Hills, I remember thinking to myself that if Fleiss had used her entrepreneurial instinct to start a bank or other legitimate business, then it would have become a household name. She’d probably be on the board of Wells Fargo today.

And of course, Steve Jobs’ ability to sell, persuade and cajole became known as his “reality distortion field.”

The point is that certain people have innate gifts.

I have not yet met Mason or seen him at work in person. I only know that his spirit and leadership was the drive behind Groupon and that at one point in time he presumably convinced everyone to turn down Google’s offer to buy the company for $6 billion. Sheesh, let’s be glad he’s not a cult leader or there’d probably be another 900 people dead in Guyana.

What happens to Mason? I don’t know. Let’s just say that an incredible amount of reality had to be distorted in order to turn down the Google offer and even more still to conduct the IPO. I would think that such talents will be deployed again and with more wisdom. Perhaps even back at Groupon.

My advice to Mason. Don’t be a fool. Get the hell out of Chicago and to the West coast as soon as you can. The laundry list of second acts noted above have a common thread: California. This is where people can start over. A yoga class is a much better place to work off your “Groupon 40” than a fat camp. To roughly paraphrase the words of Walt Whitman, here you’ll be able to keep your face to the sun, and the shadows will fall behind you.

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