Learning From Jay-Z's Successes -- And Failures (BLOG)

Six years ago, Shawn “Jay-Z” Carter found himself on the verge of finalizing one of the biggest deals of his life. The prize: A Jay-Z branded Jeep Commander that would roll off the lot boasting an audio system preloaded with all of Jay-Z’s songs, an interior swathed in butter-cream leather and an exterior slathered in a coat of patented Jay-Z Blue paint. For his efforts, the rapper would receive a 5-10% royalty on each $50,000 vehicle sold.

The Jay-Z Jeep would have been a multimillion-dollar bonanza had it ever hit the streets, but it fell through at the last minute. Through no fault of Jay-Z’s, a change of management at Jeep parent Chrysler iced the plans (the episode wasn’t reported until I stumbled upon it while reporting my new Jay-Z biography, Empire State of Mind). Those close to the negotiations say that the situation turned into a fiasco of epic proportions.

“That deal was the most [screwed]-up deal that I’ve ever seen or heard of,” says Michael “Serch” Berrin, the rapper-turned businessman who helped put together the Jay-Z Jeep proposal. “I came to Jay with the automobile industry in my back pocket to do a Shawn Carter edition vehicle that he approved, only to have the automobile industry basically shoot it down for fear that he was a bigger star than the car.”

Though Jay-Z is a perennial hip-hop Cash King, the eponymous Jeep is one of many deals crowding his entrepreneurial wastepaper basket. But listen to some of his work and you might get the impression that he’s never made a misstep in his life. He utters the phrase “I will not lose” in at least three different songs and constantly peppers himself with godlike monikers “Jay-Hova,” “Hova,” and “God MC” throughout his oeuvre.

In many ways, though, Jay-Z’s failures are more instructive than his successes, especially for people who aren’t lucky enough to be famous rappers. Take the Jeep deal. Two years after talks with Chrysler fell apart, rival General Motors hosted a gaudy gala in a gigantic tent on the shores of the Detroit River. A procession of celebrities, including Carmen Electra and Christian Slater, escorted new vehicles down a brightly lit runway. But the star of the show was the man who emerged from a blue GMC Yukon—none other than Jay-Z. For his efforts, sources told me, Jay-Z received a seven-figure sum.

Though the evening’s events suggested a Jay-Z Yukon might have been in the works, that vehicle never emerged, either. It seems Jay-Z was mostly interested in promoting the truck’s Jay-Z Blue paint and receiving a hefty payout. To be sure, that sum was a lot less than what he could have gotten had the Jay-Z Jeep ever come to fruition. But as Warren Buffett says, “Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely to be more productive than energy devoted to patching leaks.”

Jay-Z took that advice, which resonates for many people across a spectrum of situations, from workplace drama to relationship problems to actual vehicle trouble. Like many successful people, his time is simply too valuable to waste on a troubled situation, even if the payoff could be huge.

Another lesson from the Jeep episode: Don’t publicize your failures. By all means, tell your significant other, tell your best friend, tell your shrink. But don’t make a scene every time something goes wrong, or people may start to judge you as harshly as you judge yourself. Jay-Z’s invincible aura, both as a musician and a businessman, has been cultivated through constant emphasis on victory—and by sweeping under the rug anything with an unsavory result.

To the aspiring entrepreneur, there’s something heartening in knowing that even Jay-Z doesn’t get it right every time. Sure, he’s got the fame, the money and the girl (and soon, the baby), but he’s taken his lumps like everybody else. That might be even more inspirational than his success—and Jay-Z probably knows it. But publicizing his defeats just doesn’t work for his image.

Besides, “I will not lose” just has a better ring to it than “I might lose sometimes, and though it’s not necessarily my fault, it’s a lot more instructive than when I win, which is what usually happens these days.”