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From Paper Boy to Music Mogul: Entrepreneurship Lessons from Sean 'Diddy' Combs

From Paper Boy to Music Mogul: Entrepreneurship Lessons from Sean 'Diddy' Combs
Image credit: Kian, Entrepreneur.com
Music Mogul Sean
From Paper Boy to Music Mogul: Entrepreneurship Lessons from Sean 'Diddy' Combs
Competition finalist Dagim Girma, Sean "Diddy" Combs, finalist
Juny Nguyen, winners Toheeb Okenla and Jesus Fernandez
(left to right).
Image credit: Kristy Leibowitz

The Grammy Award-winning album that shot rapper and business mogul Sean "Diddy" Combs to stardom in the '90s was titled "No Way Out." But if Combs could decide his true legacy, it's that he has inspired inner-city kids to realize they can get out. Just like he did.

When he looks back on his career, Combs wants to be sure that he was an example for others, particularly those growing up in poor neighborhoods. He wants to know that he "was able to give them hope," and that success is possible with hard work, no matter where you start off in life.

Combs spoke to Entrepreneur.com in New York City on Thursday behind the scenes at an awards ceremony for the 2013 National Youth Entrepreneurship Challenge, a business contest for kids in low-income communities. The event honored winners Jesus Fernandez and Toheeb Okenla from South Holland, Ill., who came up with a business plan for selling innovative socks designed to protect soccer players' shins. They were awarded $25,000 worth of prizes and cash to be used for either developing the business or for education expenses. Combs donated $250,000 to the organization behind the competition, the Network for Teaching Entrepreneurship.

It's no wonder Combs was guest of honor at the event. Combs was born in Harlem in 1969, grew up in Mount Vernon, N.Y., and started his entrepreneurship career early with a couple of newspaper routes. In college, he talked his way into an internship at Uptown Records, where he climbed the corporate ladder to become an executive. He launched his own record label, Bad Boy Entertainment in 1993, and signed rap legend Notorious B.I.G., among other hip-hop names.

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Combs – also known as Puff Daddy and P. Diddy – released his own first album "No Way Out" which won a Grammy for best rap album in 1998. He went on to release numerous other albums and star in a handful of movies. Combs launched his own fashion line, dubbed Sean John, and he is currently in production to launch Revolt, a cable music network. Revolt, which premiers on October 21, will be for music what ESPN is to sports, Combs says.

For Combs, being ambitious is about striving for autonomy. "Every kid likes being able to have their own money and their own independence. Everybody remembers that feeling of being able to buy their own first toy from their allowance. And there is a certain pride that comes from being able to have that independence," said Combs. "Being an entrepreneur to me means belief in myself, and belief in my dreams, and independence and freedom."

With a net worth estimated at more than half a billion dollars, Combs has bootstrapped and hustled his way into quite a bit of independence and freedom.

Related: Inventor of the Wildly Popular 'Rainbow Loom' Weaves the American Dream With Rubber Bands in a Detroit Basement

Here are his top business tips.

1. If you are going to run a business, make sure you have a way to make money. Combs says there's truth in the saying "If it don't make dollars, it don't make sense." To run a business, revenue has to come first.

2. Be deliberate, but jump when the time is right. As a business owner, you have to take care of your employees. If you have received outside funding, then you are also the caretaker of somebody else's money. Don't be foolish, says Combs.

"When you are in a business, you are really responsible -- especially if you have a staff -- you are responsible for your investment and you are responsible to the people that work for you and so sometimes you gotta make the hard decisions. Sometimes you gotta make more of the conservative decisions," says Combs. "But also, any true entrepreneur knows that at some point you have to make that gamble."

3. Be the master of your domain. Inherent in taking a risk is the possibility of loss. The way to be sure that you are taking a smart risk, and not a foolish risk, is to know the market you are working in, backwards and forwards, inside and out.

"Make sure the odds are in your favor. And to do that, make sure that you are a master of that category that you are investing in, or you are trying to start a business in," said Combs. "Any business I get into, I go and I do the proper studying and I do the research to make sure I thoroughly understand that business."

As a record producer, rapper and now founder of a music cable network, Combs follows his own advice. Most of his entrepreneurial ventures have all been in the music industry, a field in which he is an unabashed expert.

4. Give people what they want. Know your market and use common sense. You can't sell to consumers who don't want what you are offering. "What do people need? What do people want?" asks Combs. "That is the start of a great businessman or woman -- just understanding what people need and people want."

5. Don't try to go it alone. Individuals who are attracted to entrepreneurship often have exceptional levels of ambition. That can sometimes spill over into a level of perfectionism and desire for control that can be ultimately restrictive. Combs had to learn, throughout his career, that to grow his ventures he would have to be able to step back and let others help him.

"When you start out as an entrepreneur, it is a lonely place. You start out with a dream yourself, and the first person you hire is yourself. And so it took a while for me to be able to start to train and give up some of the power to other people in order to enable myself to continue to grow," he says. "I used to be a micromanager, and I still am some time. But I am more of a macro-manager now." 

Related: How Kat Cole Went from Hooters Girl to President of Cinnabon by Age 32

Catherine Clifford is a senior writer at Entrepreneur.com.

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