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. (Andrew, if you’re reading this and are impressed by our song choices, give us a call. We’d love to work with you as a producer on this project. Let’s make some magic together.)

1. Takin’ Care of Business by Bachman Turner Overdrive

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.”

2. Can’t Buy Me Love by the Beatles

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, roughly the annual income of a train hobo. 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. It’s debatable whether declining cash on the grounds that it can’t “buy you love” is a sound investment strategy. And for that matter, can you really take a guy seriously who sings “I may not have a lot to give” when his net worth is estimated at $230 million? But whatever, it’s a catchy song.

3. Make ’Em Laugh from the Singin’ in the Rain soundtrack

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, which has been forever seared into our brains. 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.

4. California Love by 2Pac, featuring Dr. Dre and Roger Troutman

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.” Okay fine, we’ll admit it, we just want to hear Mason rap. This is one of those tracks that will be far more effective during live shows, where Mason can show off his “Death Stare.” You think Dre had a menacing sneer? You ain’t seen nothin’ yet, playahs.

5. Theme from Battletoads

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, you probably weren’t playing Nintendo games during the early 90s. It’s unlikely that video game metaphors are being taught at Harvard Business School, which is too bad because it’s a pretty excellent teaching tool. Battletoads is one of the most difficult video games in history, an endurance test requiring huge risks, photographic memory, and foolish confidence. The music alone will have a Pavlovian effect on listeners, steeling them for the economic challenges ahead. Also, because it’s so synth heavy, it’ll give Mason a chance to show off the piano skills he learned at Northwestern.

6. Umbrella by Rihanna, featuring Jay-Z

Long before Groupon made him a household name, Mason was best-known as the entrepreneur who wanted to build a dome over Chicago. Yes, it sounds like something a Bond villain would propose, but Mason was being completely serious. “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. Bad luck for him, and a helpful cautionary tale for up-and-coming CEOs.

7. Keep the Customer Satisfied by Simon and Garfunkel

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 & Garfunkel song from 1970 doesn’t go into as much detail about Mason’s philosophy, other than repeating the line “Just trying to keep my customers satisfied.” As a bonus, Mason also gets to complain about his 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.

Hidden Track: Independent Women by Destiny’s Child

Yes, Mason said there’d be just seven songs. But he could slip this one in at the end, as a special treat for loyal fans. “All the women who independent/ Throw your hands up at me/ All the honeys who makin’ money/ Throw your hands up at me, baby/ All the mamas who profit dollas/ Throw your hands up at me.” It’s got everything in the Mason wheelhouse: Financial independence, goofy enthusiasm, making “profit dollas”—which admittedly is a little ironic, given that Mason lost billions for Groupon. The bottom line is, a recording of Mason rhyming “honey’s” and “money” would just make the world a better place.

(This story originally appeared, in a slightly different form, in Bloomberg BusinessWeek.)