Robert asked:


Puffy Daddy? P. Diddy? Sean John? Whatever you call him, to say Sean “Diddy” Combs wears multiple hats would be an understatement of gargantuan proportions. He is a record producer, label executive, rapper, actor, fashion designer, TV producer, party promoter, entrepreneur and, sometimes, dancer. Amazingly, even as he does business in this Attention Deficit Disorder style, the Renaissance man finds incredible success in every field – making him more than the toast of the hip-hop community, but the business community as well.

Like so many hip-hop entrepreneurs of his ilk, Combs had humble beginnings. He dropped out of Howard University to taken an internship at Andre Harrell’s Uptown Records. But the young upstart exceeded every expectation, and within a matter of months, he had risen from an unpaid internship to become a vice president at the label. He was just twenty-one years old.

That said, Combs’ poor attitude was soon rubbing Uptown’s staff the wrong way, forcing Harrell to fire the young executive. In retrospect, it was probably the best thing to happen to Combs. It taught him humility while forcing him to go out on his own, forming his own record label, Bad Boy Entertainment.

Bad Boy would go on to have huge success with acts like The Notorious B.I.G., Ma$e, 112, Faith Evans and more. Combs himself came out from behind a desk to take a starring spot behind the microphone under the name Puff Daddy. As an artist he has won three Grammy awards and two MTV Video Music Awards.

Like so many young entrepreneurs, Combs wanted to parlay his music industry success and take advantage of opportunities in other arenas. That said, it would be his clothing line, Sean John, which found the greatest success.

Started in 1998, Sean John is a men’s clothing line that merges urban style with mainstream fashion. With annual sales of nearly $500 million, Sean John was nominated for the CFDA Designer of the Year award in 2000 before winning the prestigious honor in 2004.

In 2002, Combs made his entry into television when he began producing Making The Band for MTV. Since then he has added shows like Run’s House, I Want To Work For Diddy and The Bad Boys of Comedy to his production slate. He recently produced a mini-series for CBS based on the award-winning Broadway play he starred in, A Raisin In The Sun.

Sean John Combs’ success has taken him from the block and into the boardroom, but as it takes him into the future, one thing is certain – he’ll be working nonstop and will find success by any means necessary. Did we expect anything else from the original Bad Boy?



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Robert asked:


Brooklyn-raised rapper Jay-Z has taken hip-hop’s entrepreneurial spirit to all new heights, parlaying success on the mic into a multi-million dollar business empire that includes a clothing line, nightclubs, film production, sports team management and much, much more.

Born Shawn Carter on December 4, 1968, Jay-Z was earning an education on the streets of New York before attending George Westinghouse High School with a number of future stars: The Notorious B.I.G. and Busta Rhymes. Of course, he wasn’t in school long. At an early age, Jay-Z started selling drugs to make ends meet. It’s a life he would recount again and again in his records.

Even as he dabbled in the drug game, Jay-Z always had his mind set on something greater, a way out of the Marcy Houses housing projects in his run down Bedford-Stuyvesant neighborhood. Rapping had always been a hobby, but it looked like a possible way out when he started earning a reputation as one of the better battle MC’s in New York. When his talents didn’t lead to a record deal, Jay-Z and a young up-and-coming music exec, Damon Dash, decided to take matters into their own hands, forming a record label of their own, Roc-A-Fella records.

The endeavor proved to be a success as Jay-Z first album, Reasonable Doubt, became one of the most critically acclaimed hip-hop albums of all time. Jay-Z and Dash sold a 50% stake Roc-A-Fella to Def Jam for $1.5 million.

Always looking to reinvest their earnings in an effort to grow their brand/business, Jay-Z and Dash formed the Rocawear clothing line in 1999. By the late 90s, the hip-hop clothing niche had already exploded. Competition was stiff. Still, Rocawear was a stand out and was one of the last brands standing once the hip-hop trend subsided. The label sells a wide range of urban inspired clothing: from men’s and women’s clothes, children’s clothing and other accessories. After a break with Dash, Jay-Z sold Rocawear to the Iconix Brand Group for $204 million.

Jay-Z’s success hasn’t stopped there. His recording career continues to flourish as he has sold more than 50 million albums worldwide. On top of that, he continues to reinvest in his most valuable asset, himself. He is co-owner of several successful nightspots called the 40/40 Club. He recently purchased partial ownership in the New Jersey Nets (with an eye to moving them to his hometown of Brooklyn, NY.) There’s no telling what the future will hold for Jay-Z, but one thing’s for sure – it will be bright.



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Robert asked:


Born in 1972 to a Jewish family out of East Brunswick, New York, future clothing designer Marc Ecko was born Marc Milecofsky.

An early interest in art and, in particular, graffiti led to a fondness for clothing design. It wasn’t long before the entrepreneurial teen was selling painted t-shirts out of his family’s garage.

It was an uphill journey, but those modest beginnings led to the creation of one of the most influential urban clothing lines of our generation – Ecko Unlimited. Today, the Ecko umbrella of brands include Zoo York, Avirex Sportswear, G-Unit Clothing Company and the Marc Ecko “Cut and Sew” Collection.

In 1993, Ecko Unlimited was one of the few apparel lines in the urban space. Today, there are dozens of lines competing for the same dollars. That said, as one of the original hip hop clothing lines – Ecko Unlimited remains a leader in the industry, racking up more than a billion dollars in sales each year.

As recognition for his many success, Ecko has been included in New York Magazine’s “Influential” list and Crain’s New York Business “Under Forty” list. He recently earned the first ever Stoked Award for Outstanding Achievement

Of course, Marc Ecko has used his success in fashion to explore new opportunities and challenges that have become available to him: He publishes a men’s style magazine, Complex Magazine. Also, the thirty-seven year old has expanded into entertainment – teaming with Electronic Arts to produce a successful graffiti-based video game appropriately titled Marc Ecko’s Getting Up: Contents Under Pressure.

And even with successes, it’s possible Ecko will become best known for his philanthropic work. He has been very active in trying to reverse the plight of the world’s rhinoceros population and has lobbied to have the ban on graffiti art lifted in New York City.



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