The personal assistant wears Prada
Posted on Nov 21st, 2007
The personal assistant wears Prada

How style entrepreneur Fonzworth Bentley became the Emily Post of the hip-hop world

By JORDAN TIMM -- Maclean's

Bentley's rise reflects the growing prominence of the PA as a pop-cultural archetype. (AP/Chris Weeks)

Holding a parasol above the head of a hip-hop mogul, shielding him from the French Riviera sun: it's an unlikely way to launch a career, but it worked for a dandy named Fonzworth Bentley.

In 2001, a photo hit the wires of a well-appointed Diddy (formerly known as Puff Daddy) on vacation in Saint-Tropez, attended by his dapper personal assistant (PA). The shot appeared in Time and People, got talked up by television hosts, and helped turn Bentley into a celebrity in his own right. Riding his stylishness to TV appearances, endorsements, a record deal and a new etiquette book, Bentley is living the fantasy that's drawing many ambitious graduates to the booming celebrity personal assistance field.

Bentley's rise reflects the growing prominence of the PA as a pop-cultural archetype. Consider the fictional Andy Sachs, chasing her dream job in journalism by working as PA to a tyrannical fashion magazine editor in The Devil Wears Prada. On celeb tattle websites like TMZ, assistants often slip into the spotlight.

Britney Spears's PA, for instance, is regularly photographed by her side as the singer escapes a nightclub at 3 a.m. Sometimes, PAs even become part of the story itself: when Lindsay Lohan was arrested for drunk driving and cocaine possession, the bizarre late-night escapade involved both her assistant Tarin and Tarin's mother.

People are drawn to the profession by the prospect of travel and reflected glory - but the old notion of the Girl Friday who gets coffee and runs errands is outmoded, says Dionne Mahaffey-Muhammad, the founder of Celebrity Personal Assistants Inc., a U.S. firm with A-list clients from the worlds of film, fashion, TV and sports. "You have the educated and the middle class looking at these behind-the-scenes entertainment positions," she says. "You have individuals who would otherwise come out of college and seek a position at a Big Five firm."

Even the most recent edition of The Princeton Review's Best Entry Level Jobs guidebook for college grads features a section on being a PA. "Personal assistants now are lifestyle managers," Mahaffey-Muhammad says. "When you have someone who has a very complex lifestyle, you have to have impeccable management skills - people management, communication, PR, from negotiation to accounting to customer service to etiquette, dining, fashion - there's a plethora of things that an assistant needs to know to be effective. I would liken it to a co-CEO."

In this regard, Bentley - well-educated, suave and entrepreneurial - is the prototype. Atlanta-born with the name Derek Watkins to parents active in the business world, he attended tony Morehouse College - alma mater to the likes of Dr. Martin Luther King, Jr. and Spike Lee.

In his authorial debut, Advance Your Swagger: How to use Manners, Confidence, and Style to Get Ahead, he offers tips on etiquette and dress; but the book's underpinning - and no doubt the attraction for many readers - is the story of how he moved to New York City "without knowing a soul in the entertainment industry," charmed his way into a job as Diddy's PA, then used that opportunity to "brand [himself], and become one of the players in the industry."

The Bentley-style crossover is the draw for lots of the wannabes who respond to CPAI's job postings. "There are people who want to use it as a stepping stone," Mahaffey-Muhammad says. "We shy away from candidates who say, 'I want to be an actor, so I want to be an assistant to an actor.' Go find an agent. You're hoping you'll get discovered because you're getting his dry cleaning? Nine times out of 10, that's not going to happen."

Even Bentley's story isn't that simple. Though he claims not to have known a soul in the industry, he was childhood friends with Andre 3000, one half of superstar hip-hop duo OutKast, and dined with Bill Cosby at the comedian's home while still a Morehouse student. Those who do land PA jobs may find less glamour than they expected, even if they follow directly in Bentley's footsteps.

Diddy is currently taking advantage of the PA fantasy with a publicity stunt, looking for a new assistant via YouTube. In a video filmed on his yacht in Saint-Tropez, the hip-hop star surveys the scenery and announces to his prospective applicants, "You'll probably be places like this with me." Then he points to a mountain of luggage. "And you'll probably be carrying a bunch of motherf--king bags like these." Ten thousand candidates responded on the first day the job was posted.

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