The Art of Taking Risks in Business: A Groupon CEO's Wild Ride

Groupon CEO Andrew Mason is known for his bold and often unconventional approach to business. In a recent conversation with employees, he reflected on his experiences, saying, 'If you don't have those moments where you go too far, then you're probably not going far enough.' Mason has certainly had his fair share of both successes and failures, often walking the fine line between genius and gaffe.

One notable example is his decision to run a series of Super Bowl ads poking fun at various social and environmental issues. While some people appreciated the humor and creativity behind the ads, others were offended by the company's attempts to raise awareness about deforestation, whales, and the Free Tibet movement. Mason initially defended the commercials, but eventually apologized and ended Groupon's relationship with the agency that produced them.

Mason has also been known to come up with outlandish ideas that often have no clear beginning or end. For instance, he once decided to give a pony to New York City Mayor Michael Bloomberg as a gift. The plan was to present the animal to the mayor during a visit to Groupon's office, but things didn't quite go according to plan. One of Mason's employees had Googled 'horse' and 'Mayor Bloomberg' before the meeting and discovered that the mayor's daughter had recently been in a riding accident. As a result, the pony was hastily hidden away, leaving Mason to wonder what had happened to his well-intentioned gift.

Despite his occasional missteps, Mason remains a charismatic leader who is unafraid to take risks. He has a talent for coming up with wild ideas that sometimes pay off and sometimes don't. In his own words, 'I'm the type of guy who comes up with crazy stuff, and then lets it rip.'

As Groupon continues to evolve and adapt to an ever-changing business landscape, Mason's ability to think outside the box and push boundaries will undoubtedly play a crucial role in shaping the company's future direction. Whether or not his unconventional approach ultimately leads to success remains to be seen, but one thing is certain - Andrew Mason is never boring.

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