Sean Combs’ Advice For Aspiring Entrepreneurs

Before he was Puff Daddy or Diddy, Sean Combs was a 12-year-old just trying to land a paper route.

Sean Combs’ Advice For Aspiring Entrepreneurs
[Photo: Tommaso Boddi/Getty Images]

We’re suckers for an inspirational startup story. And the man formerly known as Puff Daddy has a great one.


Last week, Sean Combs, chairman of Combs Enterprises and founder of Bad Boy Worldwide Entertainment Group, spoke during Chicago Ideas Week about his first job, overcoming fear, and the quote that inspires him the most.

Here are his three tips for success:

1. Make Everyone A Winner

At the age of 12, Combs’ entrepreneurial spirit was already in full force. Paper routes were generally procured by 15- and 16-year-olds who held the job until they left for college, and routes were passed down to people they knew.

Combs says he learned the names and addresses of all the people who had routes that were leaving for college and “made them an offer they couldn’t refuse.” He’d deliver the papers and send half the profits to them at school. That year, he had six paper routes.

2. Identify And Fill Gaps In The Marketplace

Combs knows a thing or two about music. A Grammy winner himself, he’s produced songs for artists ranging from Aretha Franklin to Sting. Combs’ latest venture, 24-hour television network REVOLT, seeks to be “the CNN or ESPN of music.”

Combs notes the consumption of music content is at an all-time high, and there’s a void in the market, with BET and MTV not playing music videos. People are searching YouTube and online for the next big thing. The landscape of television is changing, he says.


The network, aimed at Millennials, curates content across several platforms and through social media. Combs says launching a cable network is the second hardest thing he’s ever done, next to running a marathon. “I almost died,” he jokes.

3. Keep Moving Forward

A turning point in Combs’ life occurred when he broke his leg as a senior in high school, putting an end to his dreams of playing football. His Uncle “Shrimp” helped him realize he had to choose his path: Either follow in his father’s footsteps in the street (he died when Combs was 3 years old) or find another dream.

Inspired by his mother’s work ethic (she worked four jobs to support the family), Combs opted for the latter. One of his favorite quotes, from his uncle, inspires him every day: “Don’t be afraid to close your eyes and dream, and to open them up and see.”

Combs admits he sometimes second-guesses his decisions–being responsible for 2,000 employees and their families and wanting to make the right decision will do that to a person, but he doesn’t let it keep him from taking risks in business.

It’s okay to have some fear and insecurity as you’re going through it, but you need to push through it, he says. “If there isn’t a bit of fear, you can’t be fearless.”


About the author

Lindsay LaVine is a Chicago-based business and lifestyle freelance writer who's worked for NBC and CNN. Her work has appeared online in,,, NBC News, MSNBC, Yahoo, Business Insider, and Fox Business.