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The Self-Made Man: Andrew Mason

If you’re like me, you probably get Groupon offers for esoteric crap in your inbox two or three times a day. And, again if you’re like me, you’ve wondered who exactly is responsible for all these yoga class and hot stone massage discounts you keep getting, and how the Groupon service even got started.? Of course, if you’re not like me then this entire paragraph has been one wrong assumption after another, but never mind. We’re here to talk about Andrew Mason, young entrepreneur and founder of Groupon.

The great Andrew Mason

Andrew is something of a change of pace from the other young go-getters we’ve been profiling lately. Sure, he grew up in affluent circumstances (Mt. Lebanon, Pennsylvania) and was one of those super-ambitious kids who started his own business at 15 (a Saturday morning delivery service called Bagel Express), but Andrew has more of that Tim & Eric goofiness to him than many of his peers. Some of that is probably due to his college internship with recording engineer/abrasive workaholic Steve Albini, but I think Andrew has a foot in the artsy and weird. Which is nice ? as interesting as other 30-year-old millionaires are, after a while they all start sounding like members of the bad guy fraternity in Animal House.

Anyway, after Andrew graduated from Northwestern (with a degree in music, of all things) and dropped out of a Master’s program at the University of Chicago, he got $1 million from entrepreneur Eric Lefkofsky, whom Andrew had worked for as a web designer at one point, to start his own online business. Andrew used the money to start The Point, a web platform that is only notable for morphing into Groupon, which has been a good return on that initial investment, to put it mildly.

Money hasn’t stopped him from indulging his inner goofball from time to time, though. He insisted that The Wall Street Journal use his driver?s license photo as the model for their trademark stippled engraving of him, and his Groupon bio paints him as the cat-obsessed budding author of a book, titled Unleash the Power Within the Power Within: Self Help For Self Helpers. He also hired a guy to walk around the Groupon office in a ballerina outfit once, just to see what his employees would do. Harmless fun, really.

Predictably, Andrew’s sense of whimsy has the business community clicking its tongue about how that sort of behavior keeps investors from taking him and his company seriously, but c’mon. If Peter Thiel’s libertarian seasteading nonsense is acceptable, then there’s room in corporate America for guys like Andrew Mason, who certainly works as hard as everyone else we’ve talked about so far. He had a business at 15, for crying out loud, an age when most everyone reading this was popping zits and watching Dawson’s Creek. If he wants to pull ideas from Chicago’s improv comedy scene for Groupon’s copywriting manual, let him. He’s earned it.


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About Dave Kiefaber Dave Kiefaber is a Baltimore-based writer who regularly contributes to Adfreak and the Gettysburg Times. His personal website is at

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