The massive success of 50 Cent, Kanye West and P Diddy should leave little doubt that rappers are some of the best marketers and businessmen on the planet. Decades before 50 Cent cleared 100 million off Vitamin Water, Run DMC made adidas relevant and revived the stalled career of Aerosmith while leveraging their fan base to crossover to the mainstream. And at the turn of the millennium, independently distributed white rappers like Aesop Rock, El-P and Slug rode the train tracks laid down by the Beastie Boys to re-invent hip-hop and the recording industry, and pocketed six figure incomes while owning 100% of their publishing rights.

Jay-Z said it best, “I’m not a businessman, I’m a business … man.

Good advice comes from the damndest places, so with that, here are a few nuggets of marketing wisdom distilled from rap lyrics

1. Be a great storyteller

In this journey you’re the journal, I’m the journalist.

- Eric B. & Rakim, “Follow the Leader

Smart brands (and smart rappers) understand that being an effective and compelling storyteller is critically important. The best way to build loyalty and foster true advocacy is by creating a narrative that your customers will engage in and be a part of. Seth Godin defines the word “brand”  as “the set of expectations, memories, stories and relationships that, taken together, account for a consumer’s decision to choose one product or service over another.” In short, your brand is about how people feel about you, and how they tell you apart from your competitors. Given that, what could be more important to a brand than developing a meaningful story that their customers embrace and take ownership of?

2. Know your audience

I rock ready, aim, fire; while y’all rock ready, fire, aim. Then blame the stationary target while the prey escapes the frame.

- Aesop Rock, “Big Bang

The most critical component of a successful campaign is having a finely tuned understanding of who you are trying to reach, and how you are going to reach them. A lot of brands get trapped trying to mass market their product or service, and then throw up their hands in dismay when their message doesn’t connect or deliver a solid ROI. Not only is it cost-inefficient to try and reach everyone with the same message, but by crafting a message that appeals to everyone, you ultimately make a message that appeals to no one.

3. Go for the gusto

I’m not afraid of dyingI’m afraid of not tryingEveryday hit every wave like I’m Hawaiian.

– Jay-Z, “Beach Chair

It’s easy to settle for doing what’s good, instead of doing what’s great. Innovation is risky. Going for great means you might crash and burn. But it’s the brands and entrepreneurs that swing for the fences that make the biggest splash, reap the biggest rewards, and have the most fun doing it. Whether you aspire to be Apple or Mark Cuban, a willingness to go all-in on your big idea is what separates you from the pack.

I quote Young MC, “don’t just stand there, bust a move.