“See y’all don’t understand us, you know . . . Ruff Ryders is a family!” 

That’s the call to order you hear in the intro of the hip-hop song “Scenario 2000.” It’s a standout  from rapper Eve’s debut album, Let There Be Eve…Ruff Ryders’ First Lady, one of the first hits to emerge from the Ruff Ryders brand, cofounded by sibling trio Joaquin “Waah” Dean, Darin “Dee” Dean and Chivon Dean. 

Since 1988, Ruff Ryders has thrived off of being familial. The evergreen stance resurfaced during a recent Instagram Live conversation between CEO and cofounder Waah Dean and For(bes) The Culture member and hip-hop artist Chill Moody. 

“Ruff Ryders is not a collection of artists,” Waah told Moody and the #CultureTalks audience earlier this month. “Ruff Ryders is family first. To even be considered a Ruff Ryder, we have to consider you family!”

Family businesses don’t exactly have the best track record. Some 70% fail or are sold before the next generation takes over. By the third generation, only 10% remain privately held.

Those numbers—combined with the fact that Black-owned companies have historically had fewer employees and receive much less funding than non-Black business owners—aren’t the most encouraging statistics. Fortunately, the Dean siblings behind the Ruff Ryders empire are proof that lucrative family businesses can exist and thrive. 

Some 32 years and 27 platinum and gold records later, the world is finally able to get a behind-the-scenes look at the bond that built this multi-million dollar empire. The business has evolved to encompass music, film (Dee and Waah launched Ruff Ryders Films in 2014), lifestyle (Ruff Ryders Lifestyles and Ruff Ryders Motorcycle Club) and philanthropic arms (the trio launched the Ruff Ryders 2 The Rescue Foundation in 2020).  

Now the family is setting its sights on television with the release of the five-part documentary series Ruff Ryders Chronicles, airing on BET August 12. The three siblings are executive producers on the project. 

There’s certainly a rich history to be told. After a stint in prison for armed robbery in the early ’80s, Waah Dean was determined to pull his family off the streets. In 1988, he formed Ruff Ryders and recruited his siblings, Dee and Chivon, as founding partners. The trio was separated during their adolescent years, and Waah was determined to get to know them again. 

“Dee was a little reluctant at first as the allure of the streets had him focused elsewhere,” Waah says. “So I went to Atlanta with Chivon to build the foundation. The  goal was always for this to be something for the three of us because this has always been about family.” 

A three-person team can’t sustain a multifaceted business on its own, so they’ve recruited other members. But even the most established professionals need to learn the Ruff Ryder ropes: “Anytime [our label partners] would send someone to us, we would put one of our family members with them so they could learn what they’re doing,” says Waah. “They may be the experts but we want our people to be the new experts and the best way you become that is by watching and learning. You have to embrace family to work with us or you’ll be too left out to be successful.”

As ubiquitous as the music genre may be now, in the late ’80s—when Ruff Ryders first emerged—hip-hop was associated with poverty, crime and, most notably, the crack epidemic. As a result, leaders in the nascent business were often ostracized. Working with family was a source of solace. 

No Limit Records founder Percy “Master P” Miller, who rose to fame around the same time as the Dean trio, founded his company on the same familial basis as Ruff Ryders. His five-part No Limit Chronicles docuseries, also produced by BET, concludes right ahead of the premiere of the Ruff Ryders series. Both are part of BET’s ode to spotlight “family, hustle and legacy.” 

“Family is everything to me,” Master P told For(bes) The Culture founder Rashaad Lambert, echoing Waah’s sentiment. “We come from generations of poor people and the only way to break that generational curse is with a firm hand of education. In my family, we don’t pray for money, we pray for wisdom.”

Newer generations of music executives have woken up to the value of running a family business. Griselda Records is just one example. The music label was founded in 2014 by rappers and brothers Westside Gunn and Conway the Machine. The two, along with fellow rapper and cousin Benny the Butcher and in-house producer Daringer, form the core of the Griselda Records roster.

Ruff Ryders’ original “first lady,” Eve, would eventually leave music to pursue her acting career, snagging the hit TV show Eve along the way. She still very proudly claims the Ruff Ryders name, and continues to receive support from the brand.

“We raise our artists and they grow up in the industry to go on and do bigger and better things,” Waah says. “We never wanted to hold anybody back. When one wins we all win.”

For(bes) The Culture is Forbes’ recently launched hub for Black and brown professionals.