Twenty summers after his seminal hit “Hustlin'” turned him into an overnight rap heavyweight, Rick Ross has transitioned from a hitmaker into something far rarer in music: an institution. Marking two decades since his debut album Port of Miami entered the Billboard 200 at number one, the Maybach Music Group founder sat down with Bernadette Giacomazzo for a candid Playboy 20 Questions feature.

Catching up in New York City shortly before the release of his 12th studio album, Set in Stone, Ross opened up about accountability, artificial intelligence, his creative studio rituals, bad contracts, and the exact legacy he intends to leave behind.

A Two-Decade Legacy of Chart Dominance and Empire Building

To understand Ross’s standing today, one must look at the foundation he has built over twenty years in the spotlight. Since Port of Miami took the country by storm in 2006, Ross has established one of the most consistent catalogs in modern hip-hop history, securing five #1 debuts on the Billboard 200 and accumulating nine career Grammy Award nominations—including nods for “Gold Roses” (feat. Drake), “Purple Lamborghini,” and “God Did.”

Beyond his solo output, Ross established Maybach Music Group (MMG), turning his brand into a launching pad for major stars like Meek Mill and Wale while releasing a string of culture-shifting projects. His entrepreneurial footprint quickly expanded beyond music, spanning high-profile brand partnerships like Luc Belaire Rosé and his annual car and bike show hosted at his sprawling 109-room Georgia estate, the Promise Land—formerly owned by boxing icon Evander Holyfield.

Redefining Power, Wealth and Respect

When asked about his landmark estate, Ross reflected on how his perspective on success has shifted over twenty years of continuous grinding. While early career milestones centered around tangible luxury, his definition of power today has stripped away the excess.

“Power is truly about happiness,” Ross told Bernadette Giacomazzo. “Power is truly about having time—time for yourself and time to spend where you want. Time is the one currency you cannot get back. What’s the use of having all the financial wealth but not having the time to enjoy it and share it with the ones who mean the most to you?”

Despite accumulating extreme wealth and commercial success, Ross emphasized that money continues to have strict limits when it comes to personal character and standing in the community.

“Money still can’t buy you respect. That’s something you have to earn,” Ross stated. “You could have a lot of money, and where you’re from, you might still be considered a piece of shit. That’s the truth. You have a lot of work to put in out here. You can’t buy respect.”

Total Accountability and Lessons from the Loss

When discussing what modern manhood means to him compared to when he first entered the music business, Ross boiled his answer down to a single principle: complete self-reliance.

“Total accountability. No excuses necessary. If it goes wrong, it’s your fault. If it goes right, that’s right,” Ross explained.

That emphasis on accountability extends directly to his advice for younger artists navigating the music industry. Reflecting on early business mistakes, including his initial record contract, Ross views those stumbling blocks as crucial building blocks rather than setbacks.

“Taking losses can come with some of the most valuable lessons you will ever learn,” Ross noted. “The first contract I signed, which really didn’t turn out well for me, became a blessing. I’m not a person who is going to complain. I’m going to work myself out of the situation and make sure I never put the people around me in that same predicament.”

Human Soul vs. Artificial Intelligence

Addressing the rise of artificial intelligence across hip-hop and the broader music industry, Ross drew a sharp distinction between technological imitation and human authenticity.

“Technology can duplicate the greats. That’s all it really is: artificial intelligence,” Ross remarked. “But can it accurately capture the soul of Rick Ross? No. Could it duplicate what I’ve already done? Of course it can. But every time I step in front of the microphone, I’m going to do something, believe it or not, in a way I’ve never done it before.”

When asked whether young artists who cannot afford a Rick Ross feature should turn to AI, the rap mogul shut down the idea, offering a direct hand to the next generation instead:

“I might not charge him. I work with artists all the time… To all the young hustlers who are really working hard, reach out to me. I’m willing to potentially collaborate with you. It’s most definitely not about money.”

Studio Rituals, Romance and the Ultimate Legacy

The Playboy feature also provided a behind-the-scenes look at Ross’s creative process and personal life. Before stepping into the booth, his studio ritual remains strictly consistent: “a chilled bottle of Luc Belaire Rosé and usually three or four joints of the finest flower that the streets have to offer.”

On a personal level, Ross spoke fondly of his relationship with model and real estate agent Jazzma Kendrick, citing her sense of humor as her most attractive quality and admitting to embracing simple, unpretentious moments:

“I never thought I would fall asleep holding hands with someone. Just that intimacy. Oh my God, I never imagined Rozay doing anything like that.”

Looking back at a career spanning two decades, Ross summed up his progression as moving from the “mud to marble” era to rapping from a “penthouse perspective.” Yet, when asked how he wants history to remember William Roberts II, his answer was stripped of grandiosity:

“An amazing hustler. I would be extremely cool with that because I never came into the game seeking radio spins… I always wanted to do it for the streets, for the culture, and for where I came from. And here we are, 20 summers later. Ricky Rozay couldn’t have fathomed that. Yet here we are.”