DJ Envy’s scandal shows the darker side of rap hustle

The rap game is built on hustle. Sometimes that hustle is just hard work and sweat equity, but the industry’s emphasis on making money at any cost can sometimes make it a target for shadier operators. The latest main character caught up in questionable financial endeavors is The Breakfast Club’s DJ Envy, who has been the subject of countless jokes on Twitter and Joe Budden podcast episodes since last month’s arrest of one of his associates. On October 18th, the New Jersey district of the U.S. Attorney’s Office announced that it had charged real estate investor and influencer Cesar Pina with “committing a multimillion-dollar Ponzi-like investment fraud scheme.”

In their breakdown of the case, the attorney’s office explains that Pina “partnered with a celebrity disc jockey and radio personality to conduct real estate seminars around the country. Through these seminars, self-promotional efforts, and other marketing strategies, Pina developed a significant social media following.” Pina courted money from investors, which he claimed would be used for “the alleged purchase, remodel, and sale of specific real estate projects in New Jersey,” promising a generous and fast rate of return. But instead of paying investors their money back, the government claims, Pina essentially robbed Peter to pay Paul: at some point, he started using the investment money to his own ends and had to recruit new investors in order to pay the old ones back, initiating a vicious cycle.

DJ Envy isn’t named directly in that statement, but people in the know deduced fairly quickly that the “celebrity disc jockey and radio personality” mentioned in that press release was The Breakfast Club co-host. Pina has made many appearances on the Power 105 morning show over the years, and his associations with Envy were readily publicized. Pina has been fairly public about the case since his arrest and he’s made it clear that Envy wasn't the one doing the actual defrauding. Envy hasn’t been charged in the case, and alleges he lost money in Pina’s scheme too, but it’s evident that the two had some kind of partnership based on how often Envy used his platform to advertise Pina’s ventures. And it's this platforming of Pina that's at the center of a lawsuit launched against DJ Envy by at least nine individuals who claim that Pina's Breakfast Club appearances gave him credibility.

Even though the true nature of Envy and Pina’s professional relationship is unclear, it’s safe to say it’s an embarrassment for the DJ and his employers. Most of Pina’s Breakfast Club appearances have been scrubbed since the story blew up, but you can still stream a June 2022 episode. It features an interview with Pina alongside his wife and business partner “Jenni Tips;” the couple was on the show to promote a seminar with DJ Envy at the Javits Center in New York, which Pina’s website touted as a “life-changing experience where they share their knowledge and industry secrets,” including “crypto, NFT, and real estate in the metaverse.” (Like Envy, Jenni Tipps has not been charged with a crime).

Around 24 minutes in, the preponderance of shady real estate schemes comes up, and the couple is fairly insistent that everything in their operation is above board — Jenni Tips at one point says bluntly “We’re doing everything on the up and up.” But as they describe their so-called real estate investment “community,” it sounds like your classic Ponzi scheme, billed as a subscription service that offers an education in real estate in addition to the possibility of profit: “You have to pay to play.”

Towards the end of the interview, Envy asks listeners to sign up for Pina’s service Flip2DAO — touted as “the world’s first ever real estate platform powered by Web3 technology” — with the possibility of a giveaway for a “3-family home” valued at half-a-million dollars, with the implication that the winner would rent out the property and become part of the cycle of property themselves. DJ Envy can try to claim that he was exploited too, but the platform of The Breakfast Club clearly helped lure people into Pina’s scheme. In his appearances with Pina, Envy heavily promotes their seminars together not just as financial education, but as a way to “uplift the community,” implying altruistic intentions that could easily create a false sense of security for potential investors. That framing is in many ways what makes a scheme like this so insidious: it’s not just about the money that’s stolen, but how it exploits a genuine desire to help communities of color that face real barriers to the finance industry.

Real estate has long been a source of material security for celebrities of all stripes: the moment you get money and someone to manage it, they will usually take that money and invest it into more stable assets, just in case your records stop selling or Hollywood stops calling. “I really like to buy property,” Kendrick Lamar once said in an interview — he rents out multiple properties, including a Bel Air mansion and a multi-story Brooklyn apartment. More than almost any other sector of the music industry, hip-hop is unrepentantly a commercial business, and rappers are often touted as much for their investment portfolios as their actual recording work.

Prior to his death, Nipsey Hussle was pouring millions of dollars into redevelopments in the Crenshaw neighborhood of Los Angeles. Young Dolph reportedly owned over 100 properties in his hometown of Memphis, and purchased a foreclosed house every year for his children on their birthdays. Rappers like T.I. have side hustles upon side hustles, as he uses his real estate portfolio to sell himself as an Oprah-esque financial expert. Juicy J, Dr. Dre, Kodak Black, and of course Jay-Z: the list of rappers-turned-investors is endless, and that’s without even getting into the many artists who have gotten swept up by the hustle of Silicon Valley. Last year, Nas, Lil Baby, Gunna, and Baby Keem were part of a $60 million financing round for Everyrealm, a “metaverse real estate company.” Of course, we also can’t forget the would-be banana republic of Akon City in Senegal, which one of Akon’s former business partners alleges is a Ponzi scheme.

These deals are usually above the board, but the deeply ingrained capitalist mentality of the rap industry encourages a get-rich-quick mindset that can lead to DJ Envy-type situations. So often, the price of playing the game is being played by people other than yourself, which is basically what happened with DJ Envy and Cesar Pina: whether or not Envy was actually financially involved in the scheme, he was used by Pina for his clout and the platform provided by The Breakfast Club. He’s not the only celebrity Pina used either — the disgraced investor regularly touted his relationship with 50 Cent, who at one point was in talks to produce a reality show about Pina and Envy’s property-flipping business, a la Vanilla Ice or Rev Run. Look at Jenni Tips’ Instagram and you’ll see countless photos of her with stars like Drake and Snoop Dogg, using their image to legitimize her own. In addition to the rap game, Jenni Tips has also used her connections with reality television to reach potential targets; she’s a close associate of Real Housewife Teresa Giudice, who served several years in prison for wire fraud.

When rap is perceived as a business more than an artform, it can inevitably attract scammers who see it as their own potential payday, from fake concert promoters to investors looking to prey upon the newly rich. These kinds of schemes don’t only rob people of their money, but they reinforce structural racism in the financial sector; there are very real material barriers for racial minorities in business, which people like Pina allege to exploit, presenting themselves as a friendlier alternative to a white banker with fond memories of the redlining days. At the end of the day, there’s only a few degrees of difference between these kinds of grifters and label executives who have seen rap music as an easy payday, or even establishment figures like Birdman or Diddy with long histories of chaining artists to exploitative deals. While artist-executives like Jay-Z might see wealth creation as a means to personal independence, the path to achieve it can either make you into a monster or lead you into the den of one. The rap industry might sell itself as a way out, with personalities like DJ Envy slinging investment advice like mixtapes, but it too often reifies the rat race of capitalism that treats people like products.

Rap Column is a column about rap music by Vivian Medithi and Nadine Smith for The FADER.