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Marketing Lessons from the Top 5 Rapper Entrepreneurs

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I didn’t started listening to hip-hop until 2006, when I discovered The Grey Album. It was a mash-up between Jay-Z and The Beatles. I was hooked.

As I delved deeper into hip-hop, I was surprised to find how many rappers had become very successful entrepreneurs. It turns out Jay-Z’s started his fair share of companies and is worth about half a billion dollars… and he’s not even the richest rapper out there (that info’s below).

Actually, I owe my discovery of the genre to Jay-Z’s marketing savvy. If he hadn’t released a cappella tracks of ‘The Black Album‘, then DJ Dangermouse never would have been able to make the mash-up that kickstarted my love for hip-hop. A willingness to give content away for free in order to broaden your audience is a big part of the marketing strategy for successful rappers and online entrepreneurs alike.

I dug deeper into Jay-Z’s entrepreneurial secrets and soon found more lessons from the top rapper entrepreneurs. In particular, I am going to write about the importance of cultivating your personal brand and how to create a story that works as a marketing tool.

But first, let me introduce my list of the top five hip-hop business people.

Top 5 Rappers Turned Entrepreneurs

#5 Kanye West    a.k.a. Kanye West

#4 Dr. Dre    a.k.a. Andre Young

#3 Jay-Z    a.k.a. Shawn Carter

#2 50 Cent    a.k.a. Curtis Jackson

#1 Diddy    a.k.a. Sean Combs

Yes, Diddy (formerly P Diddy, formerly Puff Daddy) is the richest rapper-turned-entrepreneur of all time. In 2012, Forbes estimated Didd’ys net worth to be $550 million. Of course, Diddy couldn’t have amassed this fortune without first creating a stellar personal brand…

Lesson 1:  Cultivate Your Personal Brand


“I’m not a businessman. I’m a business, man.”

Jay-Z, from Diamonds from Sierra Leone

Back in 1999, Jay-Z was the coolest guy in the room – and he knew it. His swagger was all over the radio with hits “Hard Knock Life (Ghetto Anthem)” and “Big Pimpin'”. His latest album was selling millions and Jay was starting to suspect he could sell more than just records.

Capitalize on Your Personal Brand


Enter Rocawear – a clothing company Jay-Z co-founded in 1999 with Damon Dash. Click here to watch the first commercial for Rocawear. Note the ubiquity of Jay-Z’s persona. We’re treated to shots of Jay-Z looking in the mirror while he tells us his personal story:

“I’m a kid from Marcy projects, from Brooklyn… My goal was to have one gold album and that was it. Then it became I wanted to show that artists could ascend to the executive ranks.”

For a large segment of the population, it didn’t matter if Rocawear was selling clothing, cologne, or candy canes:  it was Jay-Z’s, so they wanted it. Jay-Z’s success comes from cultivating a reputation as a cool, successful, and stylish human being – and then purposefully transferring that to his business ventures by association.

“My brands are an extension of me. They’re close to me. It’s not like running GM, where there’s no emotional attachment.”


Rocawear is Jay-Z. Jay-Z is Rocawear. As Jay thrived, so did the company. It turns out people spend a lot more money per year on clothes than on CD’s. In 2007,  Rocawear had $700 million in revenue. That’s when Jay-Z sold the rights to Rocawear to Iconix Brand Group, personally making $204 million in the process. That’s the single biggest score for a hip-hop entrepreneur to date.

Since, Jay-Z has continued to associate with major brands, including The 40/40 Club (restaurant/bar), NBA 2K13 (videogame), and Budweiser (beverage). In April 2013, Jay-Z announced he’ll be launching his only sports agency, Roc Nation Sports.

How 50 Cent’s Personal Brand Nearly Cost Him Millions vitaminwater_formula_50_cent In 2004, 50 Cent invested in Glaceau, the Queens-based maker of Vitamin Water. Just three years later, Coca Cola bought Glaceau for $4.1 billion. 50 Cent cashed in big, according to Addicted2Success:

50 Cent was thought to have walked away with a figure somewhere between $60 million and $100 million, putting his net worth at nearly a half billion dollars.

But 50 Cent’s biggest payday almost never happened. The reason? Glaceau had concerns about 50’s personal brand. Joel Brown explains:

“By 2004, 50 Cent was undoubtedly one of the world’s biggest pop stars. But it took some amount of convincing… to overcome the trepidation of Glaceau CEO Darius Bikoff and president Mike Repole. 50 Cent’s association with gunplay presented a problem: What if their chief spokesperson ended up dead in a rap beef?”

50 Cent averted disaster by showing Glaceau the safer, savvier side of his personal brand:

“The 50 Cent who showed up for his first meeting with Bikoff was surprisingly different from the rapper’s public image: calm, respectful and deliberate, without too many flamboyant flourishes.”

The Glaceau executives decided that 50 Cent – the person and the brand – were worth taking a chance on after all. For Vitamin Water, it meant being linked with a rap superstar and a special flavor dubbed Formula 50 (pictured above). For 50 Cent, it meant an estimated 10% share of a soon to be billion-dollar company.

More Rappers with Lucrative Personal Brands

Diddy’s lent his brand to clothing (Sean John), TV Shows (Making the Band), and vodka (Ciroc). For Kanye West it’s been fashion, including a pair of Nike shoes called Air Yeezys. Dr. Dre of course has his headphones (Beats by Dre) and that series of commercials for Dr. Pepper.

21st Century Business and the Personal Brand

It’s no surprise that successful hip-hop artists innately understand the importance of the personal brand. Their art form exalts their identity. Each verse they rap is a first-person monologue that states “This is who I am” in 16 bars.

But personal brands are important for more than just rappers and celebrities. In online business, your about page could make the difference between a successful website and one that doesn’t get enough traffic. Your LinkedIn profile could mean the difference between getting the client and getting rejected.

We like it when we can put a face to a business. Apple became the most valuable brand in the world thanks in large part to the personal brand of their CEO, Steve Jobs. Who can forget those black turtlenecks and circle-rimmed glasses? The world at large loved and trusted Jobs – therefore trusting Apple’s products as well.

Facebook, on the other hand, has suffered from being associated with Mark Zuckerberg’s dubious personal brand, therefore instilling feelings of distrust with Facebook’s brand.

I challenge you to take more responsibility for your personal brand – everything from how you dress to how you conduct yourself in a meeting, over email, and on Facebook. If you’re able to build a reputation for being cool and successful like Jay-Z did, you’ll be able to lend that reputation to your business ventures.


Lesson 2:  A Good Story is the Best Marketing

kanye vs 50 cent 1

“[It was] the music industry version of Ali-Frazier, with an avalanche of pre-fight hype to match.”

The Associated Press, via The Daily Illini

In 2007, Kanye West was the second best-selling rapper in the game. Kanye’s last album (‘Late Registration‘) had sold 860,000 copies in its first week.

The best seller? That would be 50 Cent (aka Curtis Jackson), who’s 2005 effort (‘The Massacre’) debuted even bigger:  1.14 million, the third best opening week in hip-hop history.

In an act of typical-Kanye bravado, West pushed the date back of his new album (‘Graduation‘) to the same day as 50’s ‘Curtis‘. Kanye explained why going up against the best was a safe bet, “I was the underdog because I sold less records in the past, so it was a win-win for me. If I lost, everyone would be happy that I even went up against him.”

Throwing Down the Gauntlet

For 50 Cent, the move felt like a challenge to his supremacy. So he made a bet:

“Let’s raise the stakes:  If Kanye West sells more records than 50 Cent on September 11, I’ll no longer write music… I won’t put out any more solo albums.”

50 Cent, in a 2007 interview

kanye 50 cent rolling stone cover smaallWith that one comment, 50 Cent turned his product launch into a story… and a media sensation. NBC’s Today declared “50 Cent promises to quit if Kanye outsells him” and many more newspapers, blogs, and fans chimed in around the world. Rolling Stone‘s cover (pictured) asked people everywhere, “Who will be the king of hip-hop?”

The Result:

  • 957,000 sales for Kanye West’s ‘Graduation’
  • 691,000 sales for 50 Cent’s ‘Curtis’

Kanye won handily, but 50 Cent’s week 1 bow was still the second highest of the year up to that point. Both rappers walked away winners according to Jay-Z:

“The rivalry helped both of them. It was definitely one of those moments in the game that was exciting, everybody could pick a side and weigh in on and have an opinion … it garnered a lot of attention.”

So did 50 quit the rap game like he said? No chance. Two years later he was back with ‘Before I Self Destruct

Find a Story for Your Business

“Storytelling is the game. It’s what we all do. It’s why Nike is Nike, it’s why Apple is Apple, it’s why Walt Disney built Disney World and it’s why Vince McMahon makes a billion dollars.”

Gary Vaynerchuk

A product, website, or Kickstarter launch isn’t much of a story by itself. But if you can inject elements of drama and intrigue, then you can benefit from increased attention and press coverage like 50 and Kanye did.

Let’s say you’re opening a hamburger joint in a small town. You could send a press release to the local paper saying, “New restaurant opens, offers cheeseburger with lettuce and tomato.”

Or you could send one that says, “New restaurant owner vows to sell more hamburgers than local McDonald’s by end of year or She’ll go Vegetarian.” Now that’s something that the paper might pick up.

When crafting your story, remember that all good stories have conflictcharacters, and something at stake.

What’s Your Story?

top rapper banner


Is there a way to make your business into a newsworthy story? Give a shot a telling your story in the comment section below. If it’s got all the right intrigue and drama, we may just write an article about it here at Income Diary.

I would also like to hear about your personal brand and how you think you can do the best job of cultivating it online.

If you’re interested in a more in-depth look at a rapper-turned-entrepreneur, check out Decoded:  17 Secrets to Jay-Z’s Entrepreneurial Success.


  1. Michael Chiong says:

    Being an aspiring Entrepreneur making more and more money online each day and a lover of hip hop I really enjoyed this post. I think the lesson to be learned here is that having multiple streams of income and following your passion is most important. Not many people buy music these days and these guys wanted to prove that they are not just rappers but also can excel in other aspects of business. Truly Motivating ! Thanks for sharing !

  2. Jaime Tagle says:

    Hey Nick

    Great article, i love hip hop. My favorites are Jay-Z and Kanye West.

    Jay-Z is a truly great example of entrepreneurship. I recommend you read his book “Empire State of Mind” where it details all his journey to success!


    • Thanks for the recommendation, Jaime. I’ve read his book which focuses more on his lyrics (‘Decoded’) and was impressed.

  3. Marcus Roman says:

    Great post on teaching marketing 101 in a new way. Unfortunately, many folks I speak with are still in pre-k marketing, and a post like this will definitely open their minds to the possibilities that exist when you focus on more than just the operations of your business. Without a story, or the use of that story through multiple media channels, you set yourself up to be just another face in a sea of sameness.

    • Thanks for the kind words, Marcus. I hope you’re right and I do open readers’ minds up to story-based marketing.

  4. This is arguably one of the better posts that I’ve read in quite some time. This makes me want to share my story and become more of a face behind my ventures. I have to figure out the best way to balance this, because I ultimately want to drive sells and make money. I’m offline and online marketing when it comes to my ventures because I feel that this is my strong suit, but I hope the story that I place on the web would have people all over the web gravitate to me much like many of the current beacons of online success. Question: I want to “sell products” that people need, not the opportunity to “sell products”, so should is it feasible to stay in the background for my particular vision?

    • I don’t see any reason why you would have to be in the background for you to sell products that people need. Maybe I’m not understanding your question fully.

  5. Akshat Goel says:

    Lovely post Nick. Unique Idea and well laid out blog post!

  6. I like the takeaway! 🙂
    In my outlook, even if you can use your personal computer or laptop to search blogs and articles about how to make your business become more productive, it is still wise to learn some lessons and gain ideas to those expert entrepreneurs.
    I suggest all the lessons, and I have to share this, I was glued to the pictures. Nice!

    I found this post shared on, the Internet marketing social bookmarking site, and I “kingged” it and left this comment.

  7. Wao, Fabolous Post, its really worth reading piece

  8. This is one of the best and the most interesting posts that I have read so far. Learning marketing skills from rappers; who would’ve thought about it.
    Awesome post mate.
    Cheers 🙂

  9. Craig Ronaldson says:

    Really enjoyed the article my friend

    Well written, your facts were on the money, overall a great article and blog.

    Really enjoyed the information, and will definitely be back for some more.

  10. This is a very good article. It shows the entrepreneurial side of artists and it takes that savvy to be more than a rapper.

  11. Great article Nick! I have to share this, it’s that good!

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