Image: Andrew Mason
Noah Berger  /  Polaris
Born in Pittsburgh, Andrew Mason flashed an enterprising side as a kid.
By contributor
updated 12/10/2010 10:06:12 AM ET 2010-12-10T15:06:12

Earth, it’s high time you meet Dot-Com Megastar 3.0. He is nothing like you’ve seen before.

Andrew Mason, the 30-year-old CEO of Groupon, and the latest entrepreneur to spin an inventive idea into an Internet craze – and soon, perhaps, billions of dollars – is, according to his friends and colleagues, “ridiculous, completely unserious and absurd” as well as “intelligent, passionate and organized.” He has been compared to Orson Welles and Freddie Mercury, an unpredictable performance-artist at the helm of the fastest-growing online company in America.

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Last week he walked away from almost unimaginable wealth as talks over the sale of Groupon to Google collapsed, according to several reports. Google had been poised to buy the online coupon company for a reported $6 billion.

Each day, one group coupon or Groupon goes out to at least 20 million subscribers in 29 countries via e-mail, Twitter and the Groupon smart phone app. Mason’s company typically takes 50 percent of the money spent on each deal.

With about 3,000 employees worldwide, up from just 150 a year ago, the company has annual revenues that have been pegged, quite fuzzily, at anywhere from $100 million to $2 billion. 

In his corporate bio, Mason calls himself “flighty” and claims to share an apartment with “over 20 cats.” He told the New York Times his true love is “building miniature doll houses.”

His only dress code: no sunglasses inside — because Mason hates how rock star Bono constantly wears sunglasses. Mason has been in a few rock bands, too, often stopping his shows to hand out family photos or to lead audiences in group exercises.

He lived up to his reputation in an interview Friday with Matt Lauer on TODAY. He declined to confirm or deny the widespread reports of merger discussions, choosing to talk instead about   how kids made fun of his middle name in school.

To Lauer's question about how what he would do with his new "clout" as a digital pioneer, Mason retorted: "I feel like clout is something that builds up on your teeth. I can't even take that question seriously."

Video: Groupon CEO dishes on online deals (on this page)

“Andrew is an eccentric, inspiring genius. And I wouldn’t want any other boss,” said Aaron With, 29, head of Groupon’s editorial department. Back at Northwestern University in the early 2000s, Mason and With were part of a band called Planet of the Planets.

“We played some indie rock,” With said. “But as a CEO, he runs the show like he did the music – smart and driven – but with a very weird sense of humor about the whole experience.”

On the buttoned-down side of the ledger, Mason is ranked No. 25 on Fortune magazine’s list of the most influential young business leaders. In November 2008, he launched Groupon, which features deals “on the best stuff to do, see, eat and buy in more than 300 markets,” according to its website.

Fine. Great. But buttoned-down is such a bore. Let’s get back to the wacky side of the newest business whiz kid.

Mason has played piano for a Billy Joel cover band called River of Dreams. He once went an entire week wearing shoes with the soles cut out, and eating only pizza. While interning at a Chicago music studio, Mason filmed – and posted online – a 30-minute video of him washing windows with newspapers just to prove to the studio’s owner that the cleaning technique (which the owner preferred) did not work.

And then there are his running battles with “Michael Ward,”  a bandaged, Van Halen-blasting tenant who supposedly lives in a wallpapered, studio apartment within Groupon’s Chicago headquarters.

In one episode, in front of 100 Groupon employees, “Michael” shoved Mason, then ran down a hallway after the boss knocked on his “apartment” door, ordering him to turn down the Van Halen music – “Runnin’ with the Devil” – and pay his debt.

Image: Groupon Michael's Room
Dan Frommer  /  Business Insider
At Groupon's Chicago headquarters, "Michael's room" has wallpaper, a bed with burn marks, and lots of Cheerios boxes.

“In the midst of all the crazy stuff he’s doing running this company, he makes sure he entertains himself. He likes to mix business and art in that way,” With said. “That’s the only way, I think, that he can do the job and live with himself and find it satisfying. It’s that bizarre, artistic sensibility he has. And it’s not just the weird interviews he does, but it’s also in terms of his management style and the way he gets along with people. He’s performing in this way as a spectacle.”

Business Insider: Photo tour of Groupon, funniest startup ever

Born in Pittsburgh, Mason flashed an enterprising side as a kid — painting house numbers on curbs, buying candy at retail stores to resell to classmates in the lunchroom and repairing computers in high school.

After graduating from Northwestern in 2003 with a degree in music, Mason interned at Electrical Audio, a Chicago recording studio. He saw engineers like Greg Norman logging long hours, often working through the night to help bands record their tracks. Mason has cited his stint at the studio as helping infuse him with a strong work ethic.

“I think that time might have inspired him to take every venture he had to its limits, to be driven by what he thought was good about it,” said Norman, who still works at the studio. “During that time he was always coming up with all sorts of crazy ideas. He knew how to do computer programs, and he worked out his ideas on his FileMaker.”

One of the early ideas was, which Mason developed after the United States invaded Iraq in 2003. To quell what Mason called the “echo chamber” of arguments over the war from people on the left and right, PolicyTree was designed as a virtual for civil discussions or a "policy debate visualization tool," as he called it. Through PolicyTree, Mason also saw that writing code was similar to writing music. He wanted to do more.

In 2007, he launched, which he described as “a groundbreaking approach to online collective action and fundraising.” The site was meant to be a focal point for altruistic and wealthy individuals to support nonprofit groups or fund specific needs like a school band’s trip to an amusement park.

Mason quickly saw leverage and power, he said, in the “collective buying technology” of and founded Groupon a year later as an offshoot to help make it easier and cheaper for Chicago residents to taste and try an array of experiences in their city.

“The people he’s been working with at ThePoint and Groupon have awakened that capital side of his brain,” Norman said. “Before, he (was more rooted in) socially aware intentions. His upbringing was in that vein, very liberal.”

Groupon’s swift expansion to more than 300 cities was fueled by Mason’s long hours, book smarts and zany antics, Norman said.

“It’s one of those perfect storms where you have the creativity and imagination mixed with really good intelligence and also the ability to communicate with and get along with people,” Norman said.

Now, on the cusp of a potential multibillion-dollar deal with Google, is the genius-prankster at peace with his fast ascendancy within the mainstream business community, the bucks he’s already pocketed and the far bigger bucks he stands to collect?

Business Insider
Groupon's head office in Chicago, with almost 1,000 of the company's 3,000 employees, is in an old Montgomery Ward building.

“I don’t know if he'snecessarily comfortable with the success,” Norman said. “I mean, he’s happy that he’s successful. But as far as being a gajillionaire or whatever? When I hang out with him, he’s conscious of the fact that he doesn’t have to really worry about money anymore.

“But it hasn’t hit him yet that he’s in this place that’s very unique. That’s aided by the fact that he’s so busy all the time. Like he puts it to me: ‘I basically have the same stuff I had before, it’s just that the stuff is nicer.’

“He doesn’t feel,” Norman added, “like he wants to buy an island – yet.”

Bill Briggs is a frequent contributor to and author of the forthcoming book, “The Third Miracle.”  

Video: Groupon CEO dishes on online deals

  1. Closed captioning of: Groupon CEO dishes on online deals

    >>> we're back at 7:41, what if someone offered you billions of dollars for your startup company , would you take it? the folks at groupon have reportedly accepted a $6 million offer. before i get to that, for the uninitiated, let's talk about groupon. basically you send out a deal every morning, it's a great deal on a product or service local to your customers. a certain number of people have to sign up for the deal, and if they do, they get the coupon.

    >> you should be our spokesperson.

    >> so the customer gets a good deal, the business that's providing the discount on a product or service gets exposed to a huge audience. what is your average subscriber like, who's your target audience .

    >> we're mostly people that live in cities, a little bit more female than male. people who are college edge indicate educated.

    >> 2/3 make between $50,000 and $100,000 a year. these are the customers everybody wants.

    >> yes, it's not the typical person you would associate with being a coupon clipper. this is more the type of people that everybody wants to get into their store.

    >> it's a simple formula and it has made you a juicy target for other companies wanting to get a piece of this or the whole pie. the reports of late on the business pages has been that google offed you $6 billion for this company and the same reporting says you turned it down. have you turned down a deal like that lately?

    >> unfortunately, matt, i can't speak to that. but we're excited to be -- to have a cool company that we're continuing to grow.

    >> can you at least confirm that you were in the -- i'm not looking for the specific number, will you confirm that you were in talks with google for such a deal?

    >> let me tell you a story to answer that question, matt.

    >> i have a feeling i'm not going to get an answer here.

    >> my middle name is divens. i was embarrassed at this middle name . and josh wilson made fun of me on the baseball field and i started crying and running after him and mrs. patterson ran after him. the next day on the school bus , someone said hey divens and i tried to squirt suntan lotion on those.

    >> you will stall any way you possibly can?

    >> some people say this business model is fantastic right now, but they worry, they have a major concern that's too easily copyable and that any other company can copy this and someone who wants to be aggressive and come in and undercut your fees can basically push you to the side, are you worried about that?

    >> in addition to being the fastest growing company ever, we have probably been the most copied company ever. there's over 500 groupon claims all over the country. the first groupon claim came out in the first 18 months. 99 of them are completely irrelevant.

    >> last week amazon made a significant investment in one of your competitors called living social. does that worry you that a company like amazon is pouring money into that company?

    >> we think as long as we build a product that our consumers really like to use and is useful for merchants and brings them new customers.

    >> this seems like a great niche right now, but will it feel that way when klaclaustrophobia sets in. it goss on to say groupon will regret passing on google's billions then if it doesn't all right. without going into your middle name and the story of skiquirting again, how do you answer that.

    >> even with the copycat sites out there, we have backlogged for six months for people that want to be featured on groupon. so what we're doing is something that consumers and merchants seem to like.

    >> we are excited by people like you, you are the young guns , you are the pioneers in the digital world . what do you want to do with your clout, andrew?

    >> i want to see if i can get more buildings to have laser in their name. the word laser. i don't know. do i have clout.

    >> you do have clout whether you realize it or not, and you do realize it, you do have clout.

    >>> i feel like clout is something that builds up on your teeth. i can't even take the question seriously.

    >> did i get one serious


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