Date Unknown

Brandon Fletcher

Serial entrepreneur, Brandon Fletcher.

By Jennifer Hadley

You know that je ne sais quoi feeling you get when you meet someone, and for no discernible reason you just know that they are “going to be somebody”? To me it’s a palpable feeling. It has nothing to do with the way someone is dressed. It has nothing to do with an air of superiority. Confidence? Sure. Uppity? No way. Yet this hard-to-pinpoint feeling struck me immediately upon meeting Brandon Fletcher.

In a hoodie, jeans, sneakers, and Urkel-esque glasses (albeit Burberry or remarkable knock-offs), there isn’t a single thing about his physical appearance that gives any indication of how much life he’s crammed into his 23 years. On this occasion, I’m not going to be privy to this information either, as I’m merely there to observe a taping of his Web show Date Unknown. Date Unknown documents the first actual date of couples that have met online. Well, at least it used to. For two years, no new episodes have appeared. And none of them have taken place in Los Angeles.

Observing the shoot is interesting enough. The location is the Seven Restaurant and Bar at 555 West 7th. The date begins with individual interviews. Armed with only his iPad and cameraman, Fletcher asks each, oh, let’s call them “cast members,” a series of questions ranging from, “What physical feature are you most often complimented on?” to, “What would you do if you had a million dollars?” And as I’m to find out later, he makes it a point to capture both parties giving a shout out to exactly which online site they met through. In this case, it was plentyoffish.com.

From start to finish the shoot takes just more than an hour, but if previous episodes are any indication, online we’ll see only five or six minutes. I leave the shoot a little disappointed because there really was a lot of directing on Brandon’s part, and even though I should know better, I still prefer to think “reality” shows are real. Now, I have at least a general sense of what goes into making an episode, but I still know nothing about Fletcher. We agree to meet at the Standard Downtown a few days later, where I’ll finally be able to pry into his personal life.

He’s quick to give credit to producer, songwriter, and singer Ryan Leslie for being the most important mentor in his life. But when it comes to finding out how a teenage Fletcher met up with Leslie, he’s far more nonchalant than I’m prepared for. To hear Fletcher tell it, he contacted Leslie through MySpace, with a message he admits was nothing if not arrogant: asking to come learn under him. I can’t help but ask where he got the nerve to do that.

“Why should this guy give you a chance?” Brandon just shrugs, and says it never really occurred to him that he shouldn’t ask. His response doesn’t come laden with conceit, but it rolls off his tongue with self-assurance. And while I’m slack-jawed at the sheer boldness of his action, Brandon’s candid retelling of his younger years helps the pieces start falling into place.

As the youngest of three children, Fletcher began making music before he was even a teenager. By 13 he had dropped out of school because he wanted to be a rapper. He admits to breaking his mother’s heart. In her desperation she made the decision to send Brandon to live with his father in Kingston, Jamaica. But even as a teen Fletcher wouldn’t be told what to do. “She took me to the airport three times. I wouldn’t get on the plane.” Finally the third time was the charm and he moved into “the ghetto” with his father, where he goes onto say he spent the three most difficult years of his life.

Depressed, but not defeated, Brandon finally got his way and returned to the states where he lived briefly in Palo Alto, California, Boynton Beach, Florida, and ultimately back in Harlem, New York, where his big break with Ryan Leslie came to fruition. Leslie took him under his wing and across the globe, helping Brandon earn a co-writing credit for Cassie’s debut album in the process.

But things began to crumble a bit in his relationship with Leslie, and ultimately “he sort of fired me,” he says. But Brandon sheepishly admits he had it coming, as he had launched his first online venture, a consulting/advice service to upcoming musicians, You Should Be A Star, while still under Leslie’s guidance. Naturally, this presented a bit of a conflict of interest, as he had to an extent become his mentor’s competition. However, the termination was amicable and to this day Fletcher counts Leslie one of his best friends, speaking of his influence with humble gratitude.

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