Jay Z’s 99 Problems: Music Stars Aren’t Very Good at Launching Startups

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If the message behind Tidal feels like déjà vu, it’s because Neil Young has been beating the drum for high-fidelity digital music for years. The renowned folk musician’s endorsement of a startup called Pono Music, which makes a portable music player capable of playing high-def audio files, helped it raise $6.23 million last year on the crowdfunding site Kickstarter. Young’s involvement hasn’t produced a very good product, though. Ars Technica, reviewing the $399 PonoPlayer, called it “snake oil.” Gizmodo said Pono’s underlying logic is “junk science.” A blind (or deaf) sound test conducted by Yahoo!’s David Pogue ruled in favor of the iPhone. Despite Young’s struggles as a startup founder, he’s an unwavering critic of compressed audio. He said in 2012 that he had worked with Jobs at Apple on an iTunes-like service to sell high-fidelity tracks. In the new book Becoming Steve Jobs, a quote attributed to the Apple co-founder shows a not-always-amicable working relationship: “F— Neil Young,” he snapped, “and f— his records.”

50 Cent

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Curtis Jackson, better known as 50 Cent, had already demonstrated his business cred with G-Unit Clothing and an investment in Vitaminwater, which Coca-Cola bought in May 2007 for $4.1 billion. (A month later, 50 Cent dropped his new album, along with the single Straight to the Bank.) Noticing the success of his friend Dr. Dre at Beats Electronics, Fitty decided to get into tech. In 2011, he bought a majority stake in a rival headphone maker, renamed the company SMS Audio, and installed himself as chief executive officer. Despite the celebrity endorsement, SMS Audio is an afterthought in high-end headphones. Research firm NPD Group told CNBC last year that 50 Cent’s company had less than 1 percent of the high-end headphones market by revenue. SMS is working on new hardware with Intel that includes biometric sensors to keep the company’s heart beating.

Justin Timberlake

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After making his debut as a fake digital music executive in The Social Network, Justin Timberlake decided to become a real one. In 2011, he became a co-owner of Myspace, the social network that, in fact, still exists. Timberlake appeared onstage at a Myspace news conference in January 2013, and his face welcomed visitors to the redesigned website. (Sorry, Tom fans.) Timberlake in a suit and bow tie hasn’t been enough to revitalize the website that was once home to some of the worst design on the Internet.

Will.i.am

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You would need a LinkedIn Pro account to keep track of the Black Eyed Peas frontman’s career in the tech industry. Intel named Will.i.am as the company’s director of creative innovation in 2011, and last year 3D Systems made him chief creative officer for the 3D printer maker. Silicon Valley’s favorite creative celebrity struck out on his own late last year with a startup called i.am+. Fast Company described i.am+’s first product, a $399 smartwatch called Puls, as “stupid.” The startup recently hired a prominent Sony Electronics exec and teamed up with Gucci, but it’s a race against the clock until the Apple Watch comes out and probably swallows the market. That clock will chime in 24 days.