Four key lessons in entrepreneurship from the hottest names in hip-hop

Metro Boomin performs during UMG’s Music is Universal Showcase Presented by O Organics and PUMA at SXSW on Friday, Mar. 17, 2017 in Austin, Texas.
Metro Boomin performs during UMG’s Music is Universal Showcase Presented by O Organics and PUMA at SXSW on Friday, Mar. 17, 2017 in Austin, Texas.
Image: Rick Kern/Invision for UMG/AP Images
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“The first billionaire in hip-hop, right here from the motherfucking West Coast.” That was Dr. Dre on a video posted just hours before Apple acquired his Beats by Dr. Dre headphones business for $3.2 billion.

The transaction propelled Dre into the exclusive cadre of rappers who moonlight as successful entrepreneurs, joining the ranks of 50 Cent (Vitamin Water), Jay Z (Tidal, Rocawear, Brooklyn Nets), and Diddy (Sean Jean). These rappers adorned my bedroom walls as a teenager, and now as an entrepreneur I’m searching for ways to absorb lessons from their business savvy.

My 38-year-old #dadbrain finds the current crop of rappers quite perplexing. I can’t handle the preponderance of rappers named Lil, the face tattoos, and the need to Google how to pronounce XXXtentacion. But in my futile quest to stay hip, I’ve found that today’s rappers, particularly those of the SoundCloud genre, provide a great crash course in modern entrepreneurship. Here are four lessons I learned from the likes of Metro Boomin, Lil Pump, and Childish Gambino.

1. They just start

Donald Glover, who raps under the stage name Childish Gambino, got his namesake using the Wu-Tang Clan rap name generator. Austin Post, whose song “Rockstar” spent 17 weeks as Billboard’s top song, also used a name generator to come up with his stage name, Post Malone.

The entrepreneur in me is truly dumbfounded that anyone, particularly a musician, would entrust a random webpage to pick their name (and along with it, brand and identity). But maybe that’s because my auto-generated rap names turned out to be Big Corky and Urkel Urkel.

In fact, whether you’re in the board room or a solo entrepreneur, sometimes it pays to have someone else make some of the critical choices. Making decisions is hard. A surfeit of options (or resources) can lead to what psychologist Barry Schwartz calls the “paradox of choice.” In a 2005 Ted Talk, Schwartz explained that choice has two negative effects. First, it produces “paralysis, rather than liberation,” he said; and then, once we make the choice, “we end up less satisfied with the choice, than if we had fewer options to choose from.”

Using a rap-name generator has at least one other important advantage in business: Speed. Consider this message from Amazon CEO Jeff Bezos on high-velocity decision making, from his 2016 shareholder letter:

To keep the energy and dynamism of Day 1, you have to somehow make high-quality, high-velocity decisions. Easy for start-ups and very challenging for large organizations. The senior team at Amazon is determined to keep our decision-making velocity high. Speed matters in business—plus a high-velocity decision making environment is more fun too.

2. The tools are practically free

In 2003, I was hired as the first employee of a new investment firm. This tiny firm required me to wear many hats, including that of resident IT guy, making me responsible for overseeing the consultants installing our Microsoft Exchange email server. It cost $50,000 and required us to install a custom HVAC system, only to go down often enough times to give me my first gray hairs at age 23. These days, email accounts with 99.99% uptime can be had from any cloud provider for a couple of dollars a month.

The proliferation of cheap tools has also infiltrated hip-hop, as illustrated by yet another (non-generated) silly name: Fruity Loops. Fruity Loops (it has ditched the silly name and is now sold under the brand FL Studio) is the music production software that powers a lot of hip-hop’s beats today and costs less than $100. Metro Boomin, described in Forbes last year as “one of the most in-demand hitmakers in the world,” got his start with the software when he was 13. He told Fader:

In seventh grade (…) I wanted to rap, but I needed beats. I couldn’t buy any so I just made my own. On Christmas when I was 13, my mom got me my first laptop. I downloaded it Fruity Loops, cause I had heard about it, and started messing around. Shit just blew from there. I still use Fruity Loops today.

Today, simple, creative tools for entrepreneurs are abundant, whether it’s IFTTT and Zapier to create complex (and code-free) workflows, or Stripe to add payment functionality to any website. Tiago Forte, the founder of the productivity consultancy Forte Labs, describes how a new type of worker, the “Full-Stack Freelancer,” can use software and online platforms to integrate “a ‘full stack’ of capabilities,” which “allows them to capture a much greater percentage of the value they create, instead of giving it away to gatekeepers and distribution bottlenecks.”

3. Make language your leverage

Lil Pump repeated the phrase “Gucci Gang” 53 times in a span of two minutes in the similarly named song, which hit #3 on the US Billboard Hot 100 and has been viewed over 600 million times on YouTube.

Other successful entrepreneurs also are known to use rhetorical tricks and compressed language to ensure that a growing staff stays focused on key ideas. For example, each annual shareholder letter Bezos sends to Amazon investors invokes the term “day one” to signal a commitment to staying vigilant despite the company’s massive growth.

In Richard Dawkins’ 1976 book on evolution,The Selfish Gene, he defines the concept of memes as “a unit of cultural transmission” shared through writing, speech, rituals—or, these days, the internet. He writes:

We need a name for the new replicator, a noun that conveys the idea of a unit of cultural transmission, or a unit of imitation. ‘Mimeme’ comes from a suitable Greek root, but I want a monosyllable that sounds a bit like ‘gene’. I hope my classicist friends will forgive me if I abbreviate mimeme to meme. If it is any consolation, it could alternatively be thought of as being related to ‘memory’, or to the French word même. It should be pronounced to rhyme with ‘cream’.

Metro Boomin catalyzed one of the most popular memes in 2017 with his sample “If young Metro don’t trust you, I’m gon’ shoot you,” which appeared on Drake and Future’s 2015 hit “Jumpman” and then on Kanye West’s “Father Stretch my Hands (Part 1)” and cemented itself in internet history.

4. Everything’s a WIP

It’s hard to pinpoint the release date of Kanye West’s seventh studio album, The Life of Pablo. This is intentional—West intentionally treated the album as a work in progress (or WIP). He teased tracks on SoundCloud, released the initial track list via Twitter, live-streamed the album release during Fashion Week in New York, launched it exclusively on the Tidal streaming service, and then continued to tweak the music well beyond the album’s broad release. The Life of Pablo was never really “finished”—it remains a WIP.

A similar paradigm is emerging in the way we treat our documents, and ultimately our work. This divergence can be clearly seen in Windows-based work environments versus those that are more reliant on Gmail or Slack. (Just ask your Gen X friends if they’ve ever converted a Google Doc into a PDF so they could set a document’s contents in stone.)

In Breaking Smart, a 30,000-word analysis of how “software is eating the world,” Venkatesh Rao, then serving as philosopher-in-residence at the venture capital firm Andreessen Horowitz, described this paradigm as a transition from a world of “containers” to one of “streams.” In his meta-analysis of Rao’s essays, Forte observes that containers (emails, PDFs, albums, newspapers) served well “in making sense of a world that was relatively static, simple, and slow-changing,” but with the downside of encouraging environments in which “people, ideas, and things have fixed, single meanings.” Streams (social media, music streaming, blogs, and messaging), on the other hand, are an “open, non-hierarchical flow of real-time information from multiple overlapping networks.”

In describing The Life of Pablo as “a living, breathing, changing, creative expression,” West was really forecasting the paradigm shift away from containers and into streams. He was seeing around corners, which is one of the most important skills an entrepreneur can have.