Curtis "50 Cent" Jackson should be hawking headphones. That's why he's sitting in a mixing booth at Engine Room Audio in Lower Manhattan at 9:40 a.m. Instead, though, the Jamaica, Queens-bred rapper is talking about his next Silicon Valley investments--and Sean Parker.
"I think Sean Parker damaged the music business with Napster," Jackson says. "Now he's trying to fix it."
In a charcoal gray suit with a wine-red handkerchief, Jackson looks more Gordon Gekko than chart-topping rock star. Then again, what's a modern rock star if not a branding machine. For 50's part, he's moved on from hit singles to hit investments. Jackson runs his own label under Interscope Records; he's built successful sneaker and clothing lines; he's starred in movies and video games; and he's injected capital in everything from 3-D glasses startups  to energy drink companies. In 2007, an early investment in Vitamin Water-maker Glacéau proved prescient when Coca-Cola bought the company for $4.1 billion, an acquisition that earned 50 Cent a reported $100 million. Today, he's technically here to promote his next business venture, SMS Audio, makers of high-end headphones. "The category is huge," he says. "These headphones are definitely going to be the biggest stocking stuffer."
But first, let's talk about Spotify. Jackson has invested mainly in physical products so far--vitamin drinks, fashion, headphones. But he's looking to invest in tech startups. "I have some ideas now," he says. "I don't want to discuss the deal until the papers get signed because everyone else will get excited--and then we get scattered."
When pressed, Jackson flashes a knowing grin. I ask him whether he's investing in a small music-related startup. "Well, they're really well established companies that I'll end up being involved in," he says. Like Spotify? "Those are the kinds of guys I want to hang out with, down there in Silicon Valley," Jackson answers coyly. He says he knows Parker but declines to go into any more detail. But clearly he's impressed by streaming services like Spotify, which he says, "are the future of music--the experience with Napster gave them the insight--all the information [they needed]."
Jackson ticks off characteristics that he learned from finding new talent and producers in the music industry. It's not so different looking for successful entrepreneurs, he says. It boils down to four traits: quality of material, performance, appearance, and personality. It was those qualities that led him to Brian Nohe, founder of KonoAudio, which SMS Audio acquired in August to support its sound technology. "Ultimately the vision is not just a headphone company," says Nohe, now SMS's president. "I mean, 50 wants to create an audio company. You will see us move into laptops, speakers, and home entertainment."
Jackson and Nohe say you might expect them to partner with device makers like HP, but it's SMS's technology (not to be confused with the alternate name for text messaging) that they feel will help distinguish them from competitors. Jackson is well aware he's entering a saturated market, introducing yet another offering of celebrity-endorsed headphones. Ironically it was 50 Cent's bosses, Dr. Dre and Interscope chairman Jimmy Iovine, who sparked the craze with their line of Robert Brunner-designed Beats by Dr. Dre headphones, from Monster, which led to similar cross-branding deals with Lady Gaga, Ludacris, P. Diddy, Justin Bieber, Daft Punk, and even Quincy Jones and Miles Davis. But Jackson believes SMS's wireless technology will help it stand out--technology, he adds, that's even impressed Dre and Iovine. "It uses Kleer technology, which is a higher level of technology than what's presented with Bluetooth," he says. For his Sync headphones, for example, up to four headphones can be wirelessly synced to one single source, enabling users to hear CD-quality music as far as 50 feet away, be it from an iPhone or stereo system.
Jackson also looks forward to the challenges of a competitive marketplace, especially with his mentor Dr. Dre in the mix. "[Dre] is so competitive," he says. "They're not offended by me [doing this]. This project allows me to show you from my perspective what the best quality is. [Beats by Dre] are all over the place. It's just time for a new version."
He's excited about the headphones project--not the first time he's been charged up by a new venture. When 50 Cent tweeted to his 3.8 million followers about H&H Imports, a company his G-Unit label owns 30,000,000 shares of, the company's stock nearly quadrupled, earning the rapper an estimated $8.7 million overnight. Trouble is, the self-promotion ran afoul of financial authorities. "I tell you that was a nightmare," Jackson says, laughing. "I had some conversations with the SEC."
Before the meeting draws to a close, 50 and Nohe want me to try out a pair of the new Sync headphones. I slip on a pair, and wait for the music to come on. Moments later, a song begins playing, magically streaming into my ears. It's "Disco Inferno." By 50 Cent.
Clearly he's still capable of some self-promotion.