If you’ve ever taken driver’s education you’ve probably been forced to sit through videos about the basic rules of the road, like how to proceed when you arrive at a four-way intersection, how often you should check your rearview mirrors, and what precautions you should take while driving in inclement weather. Chances are, at least a couple of these videos tried to address the rules of the road through the lens of entertainment; the clips used the kind of flimsy narratives typically associated with porn videos and starred teens who are supposed to be just like you because they’re interested in pop culture (which ensured that the videos would age poorly). These driver’s ed videos didn’t so much sugarcoat important lessons about drunk driving and safety belts as much as they doused them in pounds of the sweet stuff, often to the point where it seemed like the videos’ creators didn’t think young drivers had the capability to comprehend the meaning of one of those octagonal red signs emblazoned with the word “stop.”
That’s the tone former Groupon CEO Andrew Mason takes on a new album called Hardly Workin’. Mason dropped the news that he’d be releasing a collection of “motivational business music” tracks back in March, and he explained that he was inspired to make the album so he could feed nuggets of wisdom to youngsters entering the workforce who don’t have much of a grasp on business know-how. As he wrote on his site, many of the twentysomethings he worked with at Groupon weren’t interested in reading business books, so “I came to realize that there was a real need to present business wisdom in a format that is accessible to the younger generation.” Mason has a degree in music from Northwestern, so the idea to make an album is natural, and the dude has an unusual sense of humor that makes the concept of Hardly Workin’ come off as a joke. Shortly after Mason released the album former Time Out Chicago editor in chief Frank Sennett dragged up a point he made in his book Groupon’s Biggest Deal Ever—that Mason sticks to a bit no matter what—that makes the very idea of Mason going through the motions of releasing his album sound like a genius joke.