Groupon founder Andrew Mason is trying to get his groove back. In a blog post on May 16, he announced his relocation from Chicago to San Francisco and his involvement with the startup accelerator Y Combinator. He also mentioned that he’s recorded a seven-song collection of “motivational business music,” which he’s given the brazenly 1980s-honky-tonk-album title Hardly Workin’.
Of course, he could be pulling everyone’s leg. But Mason says the record drops on iTunes in the next few weeks. We couldn’t begin to guess what his original numbers might sound like, but we took the liberty of assembling a viable set list of actual covers—with real business lessons embedded in the lyrics—that have relevance to Mason’s life.
This is a not-so-subtle reminder that getting fired isn’t necessarily a bad thing. That “slaving job” you’ve been schlepping to every day might’ve been cramping your style. It’s part mockery of those fools with offices and desks, and part call-to-arms to all the pudgy CEOs wondering if there’s something better: “If you ever get annoyed/ Look at me I’m self-employed/ I love to work at nothing all day.” This clearly applies to Mason as an ousted executive. Although there’s some self-deprecation in there—another trademark of Mason’s business worldview—it coexists with a solid work ethic. While the song brags about “work that we avoid,” that doesn’t mean they’re slacking. Business, as always, is being “takin’ care of.”
During his tenure at Groupon, Mason was famous for not caring—or at least publicly pretending not to care—about money. First he turned down a $6 billion acquisition offer from Google in 2010, a deal that would’ve personally made him $420 million richer. Then he slashed his profits even further in 2011, cutting his $180,000 salary down to $756.72. Perhaps he was listening to this Beatles classic, with the lyrics “’Cause I don’t care too much for money,” and he took them a little too literally.
Mason tried hard to be funny. Sometimes too hard—he once apologized for drinking “too much beer” during a company meeting, and there’s that YouTube video of Mason doing yoga in tighty-whities. Mason clearly thinks it makes good business sense to keep things light and goofy, which makes this chestnut from Singin’ in the Rain all the more appropriate. Mason may not have Donald O’Connor’s song-and-dance chops, but lyrics like “They’ll be standing in lines/ For those old honky-tonk monkeyshines” sound like they were written just for him.
Mason’s recent blog post wasn’t just about his musical ambitions. He also revealed plans to move to San Francisco this summer. And what better way to celebrate his new area code than with some old-school rap bragging? If this seems contrary to the whole “motivational business” mission, check out these lines: “And pimps be on a mission for them greens/ Lean mean money-making-machines serving fiends.”
Mason’s farewell letter to his employees in March had plenty of memorable moments, but one line in particular stood out. “If Groupon was Battletoads,” he wrote, “it would be like I made it all the way to the Terra Tubes without dying on my first ever play through.” If you were confused by what Mason meant, know that Battletoads is a difficult video game requiring huge risks, endurance, and photographic memory. Its theme song, a cult favorite, is often covered by rock bands. Perhaps it will have a Pavlovian effect on workers, focusing their concentration. Also, because it’s so synth-heavy, Mason would have the opportunity to flash the piano skills he learned at Northwestern University.
Long before Groupon made him a household name, Mason was best-known as the entrepreneur who wanted to build a dome over Chicago. “I started a campaign … to raise $10 billion to enclose Chicago in a dome that would protect us from the winter weather,” he told Time magazine in 2009. He only raised about $250,000 before the project was shelved.
A cover of Rihanna’s Umbrella has obvious parallels to Mason’s kooky dome project, with real business references. “Comin’ down like the Dow Jones,” Jay-Z raps during the song. “When the clouds come, we gone.” It’s almost like he had a premonition of Mason’s fate. Just one day after Groupon’s stock plummeted 24 percent, Mason was out.
Mason’s farewell letter to Groupon wasn’t just jokes and admissions of guilt. He also shared a little business wisdom on the way out. “Have the courage to start with the customer,” he wrote to his former employees and colleagues. “My biggest regrets are the moments that I let a lack of data override my intuition on what’s best for our customers.” This Simon and Garfunkel song from 1970 repeats the line “Just trying to keep my customers satisfied.” As a bonus, the song references bad press. “It’s the same old story/ Everywhere I go/ I get slandered/ Libeled.” Sounds like something a guy named “Worst CEO of the Year” in 2012 might say. Well, at least he’ll go out with a mid-tempo bang.