William Leonard Roberts, famously known as Rick Ross, has plenty to celebrate. The Mississippi-born, Miami-raised emcee slid onto the hip-hop scene in 2006, at age 30. In 2026, 20 years later, the rapper-turned-music-executive-turned-businessman is still sliding in the music industry but now touts a multimillion-dollar portfolio, representing his mixed bag of businesses. Rick Ross is still “Hustling.”
On Jan. 28, the “Teflon Don” turns 50 years old. In what appears to be a reflective moment, Ross posted on Instagram in the wee hours of the morning. Beneath a photograph of himself, he captioned: “On this day The Biggest Boss was born!!” and declared January 28th “National Hustlers holiday.”
“You look at 50 differently when you own the land you stand on. When I was 25, the dream was getting on. At 30, it was launching an empire. Now, at 50, the dream is infrastructure,” Ross told BLACK ENTERPRISE.
When asked what it feels like to be an accomplished businessman at this milestone, Ross shared that, “It feels like we just finished the framing, and now we’re finally ready to build the skyscraper. The first half of my life was about proving I could hustle; the next half is about proving I can scale. I’m not interested in being the best rapper in the room anymore; I’m interested in having the best portfolio in the hemisphere.”
To his credit, Ross has an expansive real estate portfolio in Georgia, Florida, and Texas. Ross’ investments are nothing to sneeze at. He’s penetrated the food & beverage industry as owner of 30 WingStop and Checkers locations. His spirits include Belaire Champagne, Deacon rum and Five Spirits vodka.
Ross ventured into the tech industry as an angel investor for Jetdoc, and then there are his health and beauty, luggage, and automotive products, to name a few. Ross’s endeavors and maturity beg the question of what’s next for the middle-aged mogul.
“What’s next is aggressive expansion. We mastered the franchise game with the restaurants, we mastered the branding game with the spirits,” Ross told BE.
“Now, I’m looking at acquisitions that shift the culture. I’m looking at fintech, mass-scale agriculture, and real estate development that changes city skylines. I want to own the supply chain, not just the product.
“The accomplishment I’m still chasing is bigger than music; it’s institutional wealth. I want to reach a level of business where my companies run efficiently. That’s the difference between being a boss and being a tycoon.”
Ross continued:
“A boss dictates the move; a tycoon built the board on which the game is played.
“We are not just counting money anymore; we are counting equity, we are counting acres, and we are counting the centuries our name is going to remain on these buildings. The marathon continues, but we are running in a different tax bracket now.”
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