Top 10 Strangest Andrew Mason Moments As CEO Of Groupon


Ah, Andrew Mason, we are certainly going to miss you. By starting Groupon you opened up the entire Daily Deals market, without which we’d never know the joys of half-off rounds of golf and $12.99 designer sunglasses. You also thrilled us with reports of your quirky ways of managing the company you founded, all the way up until the way you announced you were canned by your board. Let’s rehash some of our favorite moments of America’s favorite music-major CEO:

WallStreetInsanity’s Top 10 Favorite Moments of Andrew Mason’s Groupon Leadership:

10. Who can forget Mason’s oh-so-special way of celebrating the holidays by doing a little yoga in front of the Christmas tree… In His Underwear! Uploaded in April 2008 and viewed almost 46,000 times, Mason’s video, “Yoga Bootleg,” was apparently designed as a teaching tool. “I’m appalled that an industry has grown around teaching a practice as wholesome and spiritual as yoga, so I decided to create my own free video to help people get started,” Mason wrote on the YouTube page. It’s hard to imagine Larry Page or Jamie Dimon ever giving such a gift.

9. Mason’s Twitter account is always a hoot. Even after he was fired, his Tweets were upbeat, telling colleagues “sharing oranges” is inefficient, and telling followers he was good on fat camp recommendations. Earlier in the month he took a jab at himself by Tweeting he planned to get “really” fat so he can look at his wedding photos and comment on how skinny he was rather than how fat he’s gotten. And then there’s just his off-the-wall musings you’d never expect from a CEO such as the one in December 2011, “If there is one thing in the world I could change, it would be for Justin Bieber to not have earrings.” And speaking of Twitter, on Feb. 15, Mason Tweeted a YouTube video that takes us to our No. 8 favorite thing about Mason…

8. Under Mason’s leadership, Groupon posted one of the coolest Harlem Shake videos, one that likely would never have happened under whoever his suit-and-tie replacement ends up being…

7. On the subject of videos… Who could forget the infamous Groupon Superbowl commercial that aired in 2011? Mason and his marketing team didn’t seem to realize that making fun of deforestation and the Free Tibet movement might offend a few people… or they didn’t care. The ballsiness of the commercial was awesome, but Mason eventually had to apologize.

6. Remember the early Fox TV show “Herman’s Head?” Well, it might not have been cancelled if the inner workings of Mason’s head had been featured. He’s shared some of his innermost thoughts with the world through his blog, and it’s nothing like you would expect form a CEO, that’s for sure. First there was his poem that paid homage to the vending machine guy:

What does it mean
To a vending machine vendor
If you introduce a new product in a machine
And it is sold out the next day?
It should mean
that the product is very popular
and you should get more.
Not never get that product again for over 3 weeks.

5. Then Mason enlightened the world with his philosophy on friendship:

Having friends is important. If you have friends, that means you are not insufferable. Make sure you meet the friends of your friends. If you can’t stand any of them, then your friend has poor taste and their validation does you no good. Move on. My advice: save energy by befriending people that have no other friends.

4. Mason has an extremely giving spirit. According to Vanity Fair, he planned to present New York Mayor Bloomberg with a pony when the mayor visited Groupon. The plan fell through, however, when Mason learned that Bloomberg’s daughter had been injured in a horse-riding accident.


3. He wasn’t greedy. Back in 2010, Google offered to buy Groupon for a whopping $6 billion—a huge sum for a company that hadn’t even celebrated its third birthday yet. But Mason turned it down. True to his quirky nature, however, Mason said he’d discuss the offer with Google if the tech giant would talk about his “other passion, building miniature dollhouses.” He also joked he was more interested in other companies such as McDonald’s or Exxon making an offer.


2. Mason made no qualms about his eccentricity. In an interview with the Wall Street Journal he explained he planned to use his peculiar personality to his company’s advantage.

“I was weird before we were a public company and managed to get it worth whatever it’s worth. I’m going to continue doing my thing and work my butt off to add value for shareholders and as long as they and the board see fit to keep me in this role, I feel enormously privileged to serve.”

1. Alas, eventually Groupon’s board saw Mason’s unconventionality as a liability rather than an asset. But even as he was fired Feb. 28, he went out with his own style, writing a one-of-a-kind letter to colleagues, shareholders and the public that is unlikely to soon be forgotten.
The letter begins with Mason joking about his termination, “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.” But that’s only the beginning. Later, Mason does something that no CEO, executive or possibly anyone has ever done in such a letter before—he compared the company to Battletoads. “I made it all the way to the Terra Tubes without dying on my first play through.” That’s one way of putting it, Mason. Although we would have probably used a Mario or Zelda reference instead.

[Image of Andrew Mason via Flickr/Kevin Krejci]