I’ve Got 99 Problems But a Pitch Ain’t One: What Entrepreneurs Can Learn From Rap Music

Allow Me to Reintroduce Myself
Two years ago I presented at an investor conference and when I used the phrase “making it rain” the audience of VCs and angel investors returned only blank stares. Ever since, I’ve been interested in exploring and discussing the relationship between rap music and entrepreneurship. A month ago I delivered a keynote at Startup Week hosted at The University of Texas at Austin. This piece is an adaptation of that talk.

Rap music is one of the few genres that embraces business principles. When was the last time you heard an opera singer, jazz guitarist, or dubstep producer talk about the business of what they do in their art? Rappers, however, talk about this topic all the time.


There are a staggering number of commonalities between rap and startups. For example, the culture of “performance enhancing substances” is heavily referenced in both industries.


Lil Wayne with codeine cough syrup and 3 Day Startup Alum Sri Sonti (cofounder of Remark, a 500 Startups accelerator company) with energy drink

Another common thread is that the parental approval rate for kids wanting to pursue a career in rap music or entrepreneurship is still relatively low. This is the case because both endeavors still maintain a high failure rate: 90% of new businesses fail and the number of rappers that fail is probably even higher.

Given these commonalities, there are several insights that these industries can provide to one another. Here is what entrepreneurs can learn from rap music.

Get a Cofounder

Rapper Snoop Dogg and Producer Dr. Dre/Business cofounder Steve Jobs and technical cofounder Steve Wozniak

Left: Rapper Snoop Dogg and Producer Dr. Dre / Right: Business cofounder Steve Jobs and technical cofounder Steve Wozniak

Rap music and startups resemble each other at the earliest stages. Rap music starts with a rapper and a producer. The rapper provides the words, the voice, and handles the more public-facing activities. The producer (also called a beat maker) creates the tracks that the rapper raps over. Some of the biggest names in rap music today found their initial success due to their own in-house producers (see: Drake and 40, Kendrick Lamar and Ali). Often this person not only supplies beats, but helps architect the sound of a rapper’s signature style.

This duality is eerily familiar to the beginning stages of a startup. Two people — a business and a technical cofounder—represent the best foundation on which to build a new company. The tech cofounder usually builds the software that powers the product, and the business cofounder runs operations, fundraising, or other activities that are needed for the startup.

Aside from the obvious benefit of having a cofounder with a set of skills that complement your own, having another person with dedication and passion that equals yours increases the chances of capturing opportunities by way of identifying early employees, discovering initial investors, and more.

And attaining success in a startup is difficult. There are ups and down in the process.  Having someone to balance you out is of enormous value. Single founders often endure a lonely journey.

The best way to choose a cofounder is to collaborate on projects, in hackathons, or at programs like 3 Day Startup. This is the fastest way to see a potential cofounder in action and test them out so you can understand their work ethic, capabilities, communication style, and sensibilities. How do they lead a team? How strong is their execution ability? How are they in front of a crowd? Can they build what they claim they can build?

Fail Fast
The RZA is the leader of the Wu-tang Clan, the biggest and most successful collective in the history of rap music. He is known for a gruff rapping style, grimy beats, and an obsession with kung-fu films and asian mysticism. But he had to try a few times before he found the winning formula — or what the startup world might refer to as product/market fit. Signed to Tommy Boy records in 1991, he released his first single “Oh We Love You Rakeem” under the moniker “Prince Rakeem”. Prince Rakeem’s persona was that of a smooth talking loverman character. This record flopped and rap music fans paid it little mind. Undeterred, the RZA re-emerged a few months later with an altogether new project: he and his neighborhood crew reformed as the grimier, gloomier Wu-tang clan and released one of the greatest rap records ever.

Prince Rakeem vs. The RZA

Prince Rakeem vs. The RZA

Grammy award-winning rapper Common followed a similar path: his first release, under the name “Common Sense”, represented a thuggish portrayal of life at the bottom. This release failed to gain the reception he was looking for so he retooled and eventually ended up releasing more emotional, progressively-minded lyrics referred to in the rap industry as “conscious.”

Common vs. Common Sense

Common Sense vs. Common

Initial failures provide learning and feedback to eventually reach success. Just like the The RZA and Common, several of the most famous startups in the world experienced a bump in the road before they hit it big.

Paypal began as a mobile payments company and pivoted several times before realizing that the greatest customer need their product met involved handling transactions inside the Ebay platform. This was the first step upon which Paypal created their dominance of online payment processing. Twitter, originally known as “Odeo”, represents another notable example of the founders going back to the drawing board. Odeo provided directory and subscription services for podcasts before scratching that concept in favor of short-burst messaging. Finally, Instagram began as a complicated, feature-heavy geolocation app with a Swiss army-like array of features. User behavior indicated that photo-sharing resonated most with their users so they scrapped the excess features and honed in on what really excited their users.

Practice Rapid Prototyping and Customer Feedback
The rap industry follows an extremely effective product development cycle unlike any other genre. Rappers use mixtapes as de facto beta products. A rap “mixtape” is not a cassette — it is an unofficial album not fully refined and developed, usually given away for free online. The goal of releasing a mixtape is to generate awareness and receive feedback from the market before the release of a full-length record.

Aspiring rappers release mixtapes through various channels, allowing them to build a following and catch the ear of more established rappers who run their own labels. This process is know as “co-signing” — in the startup world this could be compared to partnerships.

In the early 2000s, Lil Wayne proclaimed that he was the greatest rapper alive and the rap world let out a collective laugh. Up to this point, Wayne was considered an afterthought in the cannon of rappers on the Cash Money record label and mostly known for being the weak link in the Louisiana supergroup the Hot Boyz, which featured more marketable rappers such as Juvenile and B.G.

But he kept cranking out music at a rapid pace, eventually releasing 14 mixtapes in the early 2000s.

Lil Wayne mixtapes

Lil Wayne mixtapes

With each release, Lil Wayne was refining his sound based on feedback from listeners before releasing an official album. This proved to be successful for him. When he released Tha Carter III in 2007, the album achieved double platinum status.

Share Ideas and Tools: A Tale of Two Apaches
Ecosystems and communities matter for a slew of reasons. Good ecosystems encourage sharing ideas and tools. Rap music is built upon samples, which borrows beats or small snippets from other songs. A “break” — short for break beat — is the part of the song where the instrumentals and vocals drop out and all you can hear is the drums. Kool Herc, the father of hip hop, had the idea to get two copies of the same record and play the break beats one after another, creating an uninterrupted beat over which rappers could rap. Others starting copying this technique, searching for and sharing popular breaks from records. Some of the most famous rap songs ever are built on some famous breaks.

The image below maps out popular songs that sample the Apache break:

Songs that sample the Apache break

Songs that use the Apache break

The way the rap community uses breaks is exactly how the startup community uses open source software. Open source software is software developed and shared by hobbyists, amateurs, and professionals.

Coincidentally, one of the most important pieces of open source software is the Apache web server. This software runs major infrastructural components of some of the biggest software companies in the world.

Companies using the Apache break

Companies using the Apache web server

Represent Your Local Community
Unlike other genres, rappers constantly remind you where they are from. The regionality of rap is one of its greatest strengths: region-specific genres such as the Bay Area’s hyphy, Texas’ chopped and screwed music, and traditionalist East Coast rap all have unique signatures that provide identity, character, energy, and relevance to each community.

Startup ecosystems have similar regional differences, and coincidentally, these three rap music hubs* represent three of the largest startup ecosystems. In the startup world, the Bay Area is known for innovative consumer-facing startups. Texas, specifically Austin, is known for profitable B2B software startups. New York City is known for media and content-focused companies.

Note: Atlanta is the current center of the rap music universe but the Atlanta startup scene, while impressive, does not map as cleanly into this analogy

Note: Atlanta is the current center of the rap music universe but the Atlanta startup scene, while impressive, does not map as cleanly into this analogy

Rap regionality is a big deal because it is empowering on a local level. Successful regional artists provide success stories to others from that community. Global names matter and they always will: Global rap superstar 50 Cent and Facebook founder Mark Zuckerberg are similar in this respect. Both of them represent huge successes. But both of them emerged from fairly predictable sources, i.e. locales where lots of successful rappers and startup founders are from, respectively (50 is from Queens and Zuckerberg went to Harvard).

Tech N9ne (Kansas City), Nipsey Hussle  (Compton), or E-40 (Bay area) may not be household names in popular music. But each of these artists is stylistically inseparable from their hometowns; they embody the idea that someone from their community can make it in the rap game.

Anyone who attended Harvard can look to Zuckerberg’s success as a motivator. But it can be more motivating to see a local entrepreneur having regional success. This is why Dan Graham’s Build-A-Sign is important to Austin and Brett Martin’s Castle Branch is important to Wilmington, NC — these companies may not be well-known outside of their regions but they are symbolic of the potential of their respective ecosystems.

It is an exciting time for both rap and startups. Both of these cultural forces have boomed in popularity over the last two decades: demand for rap music and entrepreneurship are at all-time highs. The change in tide for both indicates a change in attitude of the new millennia. The current generation of young people that are driving our culture and shaping our economic future resonate with the values inherent in both rap and startups: innovation, a healthy sense of risk, and the power of community.

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