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Andrew Mason

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Andrew D. Mason (born 1980) is the founder and former CEO of Groupon, a Chicago-based website offering users discounts on local businesses. He started a Saturday morning delivery service called "Bagel Express" when he was aged 15. After graduating from Northwestern University in 2003 with a degree in music, Mason worked in web design for Chicago entrepreneur Eric Lefkofsky. Mason was employed as a developer at InnerWorkings, a company founded by Lefkofsky, in 2006. Lefkofsky provided Mason with $1 million in "seed money" to bankroll The Point, a now largely inactive web platform, which was Mason's first entrepreneurial venture on the Internet. It was found that The Point was too abstract to market, and it was stripped down to the Groupon concept. Groupon is a website that sells deals to local businesses. Groupon's website states that since its beginning in November 2008, Groupon has sold more than six million deals. With Groupon taking 50 percent of every deal, plus a small credit-card handling fee, in late 2010 it was reported by Mashable that Groupon's annual revenue was $800 million. Mason was dismissed as Groupon's CEO on February 28, 2013, the day after the company missed analysts' expectations for sales, and fell far short of the mark when it came to profit.

Companies and Investments

  • The Point (Co-Founder)
  • Groupon (Co-Founder)

Lessons Learned

Find Leverage

While Groupon was still a side project of The Point, they didn’t even own groupon.com. The person who owned the domain name was living in England and wanted to work on a group coupon idea with it so he was unwilling to sell. Andrew offered to collaborate with the owner when they started pushing into Europe. But the owner still didn’t want to sell. But because they had already trademarked Groupon in England too, the owner couldn’t use that name to launch his own group coupon company. In the end, they were able to buy the domain name for just $250,000.

Bring More to the Table

One of the reasons Groupon caught on so fast with merchandisers is that it took out risk out of the equation for them. If a small business owner wants to advertise on a newspaper, he pays money and hopes people show up. But with Groupon, the feature is free so business owners had a lot more incentive to use the service--- they had nothing to lose!

Viral Success

Groupon’s success was viral and it became a highly praised by the media. It went public in 2011 with great fanfare. However, the company faltered, reporting losses in its first earnings release and restating 2011 revenues in the next year. The stock plummeted and Andrew starting finding himself in the heat. The expectations for being the CEO of a public company were different from that of being a startup and for one reason or another, along with Groupon’s tanking stock price, Andrew was lambasted by the media and eventually left the position in 2013.

Inspiring Quotes

It’s like flying a plane and you’re trying to find the right altitude and you’re doing it with a four-year-old company and four-year-old processes and four-year-old systems.

Eric Lefkofsky

Andrew Mason's Quotes

I never thought of myself as an entrepreneur before this and I still really don’t. I just like to build things and do things.

Andrew Mason

Influential Books

Frank Sennett - Groupon's Biggest Deal Ever: The Inside Story of How One Insane Gamble, Tons of Unbelievable Hype, and Millions of Wild Deals Made Billions for One Ballsy Joker


Eric Lefkofsky, Steve Albini



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