Within the late 90s and early 2000s, hip hop entrepreneur Damon Dash was on prime of the world. On the time, Damon Sprint was the CEO of the most well liked rap label in music, Roc-A-Fella Data. Roc-A-Fella oversaw a roster of artists together with Jay-Z, Kanye West, Memphis Bleek, Beanie Sigel, DJ Clue, and Juelz Santana.
Damon Sprint was additionally the CEO of the wildly profitable Rocawear clothes line, which was reportedly producing annual revenues of $350 – $450 million. As if this wasn’t sufficient, Sprint was testing the waters in Hollywood by govt producing the critically acclaimed 2004 Kevin Bacon movie “The Woodsman”.
Maybe most significantly, with out Sprint, the world would probably by no means have heard the title Jay-Z in any respect. With the above resume, you’d need to assume that at present Damon Sprint have to be value lots of of hundreds of thousands of {dollars} and is presiding over a dynasty that rivals the empires of fellow rap moguls Diddy and Dr. Dre, proper? Sadly, that’s not the case. In recent times, Damon Sprint has reportedly been broke, has owed hundreds of thousands of {dollars} to the IRS, and has had a number of properties seized by means of foreclosures. How did this occur? That is the story of how Damon Sprint launched Jay-Z’s profession and Roc-A-Fella Data, then blew by means of his fortune and watched his empire crumble.
Sprint Meets Jay-Z
After getting expelled from three totally different excessive faculties, Damon Sprint fell into a nasty crowd and started promoting medicine. Dealing earned him loads of money, nevertheless it got here with a value. Damon give up the drug sport after seeing too many pals find yourself useless.
Damon rapidly found that he was a born promoter. He and a gaggle of pals launched a mini enterprise, throwing events and selling golf equipment. One night time, he introduced that the primary 100 women in line at a membership opening would get free bottles of Moet Chandon champagne. A line across the block shaped hours earlier than the doorways even opened, and whereas Damon really misplaced cash on the promotion, he solidified his repute as the most well liked promoter in New York.
Subsequent, Damon determined he might be simply as profitable selling musical acts as he was selling golf equipment. By way of his cousin’s stepfather, Damon landed his first administration shopper, a rap group known as Future Sound. Not lengthy after, Sprint had organized for Future Sound to signal a take care of Atlantic Data beneath an govt named Rodolfo Franklin. Along with being a document govt, Franklin moonlighted as a DJ beneath the title “DJ Clark Kent”. It was Rodolfo who, in 1994, first alerted Sprint to an bold former drug vendor from Brooklyn who was seeking to launch a rap profession. That rapper’s title was Sean Carter, quickly to be often called…
Jay-Z
Jay-Z was not like anybody else in rap on the time. He was the quickest rapper Damon had ever heard, and he did not write something down; as an alternative, he recited each rhyme straight from reminiscence. Moreover, like hottest artists of the day, like DMX, Snoop Dogg, Notorious B.I.G., and Tupac, Jay-Z did not rap about homicide and crime. Jay-Z’s lyrics tended to focus primarily on dwelling a lavish Playboy life-style stuffed with women, cash, boats, automobiles, and champagne. Bling Bling!
Roc-A-Fella Data Is Born
On the time, Jay-Z was a little bit of an underdog within the music trade. He had tried and failed for years to safe his personal document deal however was rejected for being too outdated or not showing arduous sufficient. Jay did not match the mildew of fellow typical Brooklyn rappers who wore gold enamel and sang solely about dealing medicine and killing folks.
So that they determined to go impartial.
The 2 co-founded Roc-A-Fella Data. The title was a play on oil tycoon John D. Rockefeller, who died with an inflation-adjusted internet value of $340 billion. The title was additionally a nod to a well-known Brooklyn drug vendor named Rocafella, whom Jay-Z idolized as a younger hustler. [FYI: That “Rocafella” is the one who died of AIDS and is immortalized in the NAS song “Ether”: “Rocafella died of AIDS, that was the end of his chapter And that’s the guy y’all chose to name your company after?”].
Damon wished Jay to movie a music video as quick as attainable, however Roc-A-Fella Data had no cash. To lift money, Damon sought an funding from a well-connected road hustler named Kareem “Biggs” Burke. Damon took 100% of Burke’s $16,000 funding and poured it into producing a music video for Jay’s track “In My Lifetime,” which was partly filmed on the Caribbean island of St. Thomas. Burke additionally organized for Jay and Damon to have entry to a rich native kingpin’s mansion and pace boat, which might be seen all through the video:
Jay-Z “In My Lifetime”:
The gamble paid off, and shortly Roc-A-Fella’s solely artist was getting courted by all the main document firms.
Nevertheless, not one of the main labels would conform to one in all Damon’s outrageous calls for. Damon Sprint demanded that Roc-A-Fella preserve possession of Jay-Z’s grasp recordings.
Proudly owning the grasp would develop into a superb monetary choice as Jay-Z’s again catalogue nonetheless sells hundreds of thousands of models, even virtually 20 years later. Just one document firm was prepared to acquiesce to such insane calls for, a little-known label known as Freeze Data. As destiny would have it, shortly after signing Jay-Z, Freeze Data was bought for scraps to Russell Simmons and Lyor Cohen’s Def Jam Data.
Roc-A-Fella Data Rises To The High
Russell Simmons and Lyor Cohen’s management, mixed with Roc-A-Fella’s sheer expertise and hustle, helped Jay-Z’s debut album “Cheap Doubt” promote over 1.5 million copies in its first yr. A yr later, Jay’s album “In My Lifetime, Vol. 1” would promote one other 1.5 million copies. By 1998, Jay’s album “Onerous Knock Life” would promote a whopping 12 million copies world large making Roc-A-Fella a very powerful label at Def Jam. The following 54-city “Onerous Knock Life” music tour generated $20 million in income.
Concurrently, Damon and Jay had launched a clothes line known as “Rocawear” and a model of vodka known as “Armadale Vodka”. Rocawear and Armadale’s gross sales exploded each time the merchandise appeared in one in all Jay’s movies. By 2000, Rocawear’s gross sales generated income of $50 million per yr.
Mark Mainz/Getty Pictures
The Downfall Of Damon Sprint
Between 2002 and 2004, Damon Sprint went on a tear, beginning firms, signing new artists, and usually dwelling the lifetime of an excellent profitable hip hop mogul. He had amassed a military of mega-talented future stars like Kanye West, Cam’ron, and Beanie Sigel.
Roc-A-Fella had survived the 9/11 assaults (which occurred the identical day Jay’s album “The Blueprint” debuted), Jay-Z’s arrest on assault expenses, and the tragic dying of Sprint’s girlfriend Aaliyah. Rocawear expanded to 5 totally different clothes and shoe strains and was bringing in $350 – $450 million per yr in annual gross sales. Damon was even producing motion pictures just like the critically acclaimed Kevin Bacon movie “The Woodsman”.
Fittingly, Sprint lived a really opulent life that reportedly included butlers, non-public cooks, bodyguards, a mansion in Beverly Hills, a Tribeca loft, a $35,000 monthly London condominium, and a $400,000 Maybach. Sprint was additionally well-known for under carrying his footwear, socks, denims, and shirts as soon as earlier than tossing them away. Sadly, all was not properly with the one one who mattered most, Damon’s most gifted artist and enterprise accomplice, Jay-Z.
Jay had more and more grown uninterested in Damon’s ever-growing ego and paranoia. The workers at Roc-A-Fella, Def Jam, and Rocawear have been scared of Damon’s endless mood tantrums over the smallest of points. He fired dozens of gifted executives and burned bridges left and proper.
For his half, Damon started to resent Jay’s growing distance from their firm and new alliance with Def Jam honcho Lyor Cohen. Rumors flew all through 2002 and 2004 that Damon and Jay have been breaking apart and not talking. Tensions got here to a head after Jay-Z and Kareem Burke refused to permit Damon to spend $3 million on a single print advert marketing campaign for Armadale Vodka that includes Kevin Bacon and Naomi Campbell. From that time on, Jay and Damon have been not on talking phrases. Damon was additionally being excluded from many high-profile conferences at Def Jam relating to his personal artists. The writing was on the wall.
(Photograph by Lester Cohen/Getty Pictures)
The Breakup
On December 24, 2004, Jay-Z requested his outdated pal Damon Sprint to fulfill him at an Italian restaurant in Manhattan known as Da Silvano. Previous to this assembly, the three Roc-A-Fella founders had already agreed to promote their label to Def Jam for $10 million, however Sprint was shocked by one other piece of the deal that he didn’t see coming. Every accomplice would take dwelling $3 million, however solely Jay can be promoted to be the President of Def Jam. Even worse, Jay refused to permit Sprint to maintain the “Roc-A-Fella” title. The ultimate blow occurred when all of Roc-A-Fella’s artists have been supplied the choice to stick with Jay at Def Jam or go along with Damon to a brand new label of his personal. Most artists, together with future celebrity Kanye West, selected to stick with Jay.
The few artists who went with Sprint to his new label noticed their albums bomb on the charts, and the brand new document label enterprise rapidly imploded. However, Damon and Jay have been nonetheless linked by way of Rocawear. They every nonetheless owned 25% of the corporate. After the Kevin Bacon/Naomi Campbell fiasco, Sprint was invited to a gathering at an upscale lodge room in New York. When he requested why they have been assembly at a lodge room as an alternative of the Rocawear workplaces, the companions replied, “so nobody will hear you scream”. By the top of the assembly, Sprint was expelled from the corporate with a $22 million buyout that reportedly solely resulted in $7 million in money acquired by Sprint.
Foreclosures
Between 2004 and 2009, Damon launched and shuttered a string of failed ventures. His new document firm, Roc La Familia, folded, as did clothes line The Damon Sprint Assortment. Sprint’s spouse filed for divorce, and he was sued for $15 million over an alleged rape.
At his all-time peak, Damon Sprint’s internet value was $50 million.
Shockingly, by April 2009, Damon Sprint was flat broke.
In his divorce proceedings, Sprint revealed to a decide that he really owed $2 million in again taxes and was within the midst of foreclosures on two New York Metropolis residences. He was additionally being sued by a number of NYC legislation companies and varied different collectors for lack of fee. His Chevy Tahoe had been repossessed after he couldn’t sustain with the $700 month-to-month funds.
Sprint was compelled to vacate his $9 million Tribeca, New York dwelling, which was later bought in foreclosures for $5.5 million.
In November 2019, Damon was arrested after he didn’t pay greater than $400,000 in youngster help owed to 2 ladies. The majority of the debt, roughly $370,000, was owed to ex-wife Rachel Roy.
In the meantime, Jay-Z would go on to promote Rocawear to Iconix Model Group for $219 million. Jay additionally bought hundreds of thousands extra albums for Def Jam and, in 2008, signed a brand new $150 million document take care of Dwell Nation.
Immediately, Jay-Z is a billionaire enterprise mogul. His internet value presently stands at $2.5 billion. Damon Sprint remains to be attempting to hustle his manner again to the highest, however solely time will inform if he can attain the identical heights.
2025 Chapter
In September 2025, Damon Sprint filed for Chapter 7 chapter in Florida, declaring greater than $25 million in money owed in opposition to simply $4,350 in private property. In line with court docket filings, the majority of the debt comes from almost $19 million in unpaid federal and state taxes, in addition to over $650,000 in youngster and spousal help arrears owed to a number of ladies, together with his ex-wife Rachel Roy. Sprint additionally listed greater than $5 million in lawsuit judgments, most notably almost $4.8 million awarded to filmmaker Josh Webber after a collection of disputes over the movie “Expensive Frank.” Further money owed embody smaller judgments to photographer Monique Bunn, creator Edwyna Brooks, and lawyer Christopher Brown. With no home, automotive, or regular revenue, the chapter submitting marks the fruits of 20 years of economic decline for a person who as soon as sat atop the hip-hop world.
