The Most Underrated Hip-Hop Business Moves

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Chamillionaire (via Shutterstock)

by Dan Runcie

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Last week I asked an open question on both Twitter and LinkedIn, “What’s the most underrated business move by a hip-hop artist?” The responses have been great. I have covered a number of great deals already in Trapital, but here are a few popular ones mentioned that I’ve never written about before:

LL Cool J advertising Fubu in a Gap commercial

In 1997, Gap paid for a Fubu commercial thanks to LL Cool J. The rapper wore a Fubu hat, and in his rap said “for us, by us, on the low.”

Fubu founder Daymond John said that after the commercial aired, he ran out of product. Customers were going to the Gap to try and buy Fubu! Gap found out what LL had done 3 weeks later, but Gap sales still grew 300% afterward. Everybody won.

LL Cool J (via Shutterstock)

Ice Cube starting the Big 3 basketball league

Cube knew that recently retired NBA athletes still had big fanbases and could still play the game despite no longer making a 15-player NBA roster. And he knew the 3×3 concept was great for people who didn’t want to run up and down a court anymore.

The BIG 3 was launched in 2017 and hasn’t looked back. Starting a sports league is hard as hell. Most leagues fail, and BIG 3 has had its questionable moments, but it’s continued to stay on top. I can’t speak to its profitability or run rate, but the lights are still on, and that says something.

Queen Latifah’s expansion into multimedia

Queen Latifah has been ahead of her time on almost everything. She was one of the first hip-hop artists to push for women’s rights and empowerment. She launched Living Single—the original sitcom about twenty-somethings in New York navigate adulthood! She was the first rapper to perform at the Super Bowl. The list goes on.

Her presence in TV and film paved the way for folks like Cube, LL Cool J, Ice-T, and other hip-hop figures who have become a presence in multimedia.

Queen Latifah (via Shutterstock)

Chamillionaire’s career as an investor

I haven’t covered Chamillionaire much in Trapital, which is crazy. He was a former Entrepreneur-In-Residence at Upfront Ventures and made early ties with founding partner Mark Suster. As an investor, he has had several notable exits, including Maker’s Studio (acquired by Disney), Ring (Amazon), Cruise (GM), and Lyft (IPO).

Chamilionaire has also gotten E-40, Big Boi, and Trey Songz to invest in more startups.

Chamillionaire (via Shutterstock)

E-40’s wine business

Earl Stephens Wine Selections launched in 2013 and has shown no signs of slowing down. In April 2021, he signed a nationwide distribution deal to get his product in 41 different states. E-40 is also an active investor who has backed Clubhouse and other tech companies.

E-40 (via Shutterstock)

People shared a bunch of great ones, so you if you have time, check out the threads on LinkedIn and Twitter. Other ones mentioned that I didn’t include were because I’ve covered before:

Frank Ocean’s Endless-Blonde release

Nipsey Hussle’s $100 mixtape

Nas’s investments at QueensBridge Venture Partners

50 Cent – Vitamin Water

Dan Runcie

Dan Runcie

Founder of Trapital

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