Meek Mill's Journey From the Inmate List to the Forbes List

Meek Mill became a Hip-Hop Cash King, but he will need help to maintain that status.

Last week, Meek Mill made the Forbes Hip-Hop Cash Kings list with a smooth $15 million. He secured the bag for an upcoming docu-series with Amazon, rekindled his partnership with Puma, and shifted the narrative of his place in the culture. For a man who made $25 million in his career up to that point—and spent six of the past twelve months behind bars—it is quite the come up.

The Philadelphia rapper’s life has been perpetually instable. His career took off in 2011 with tremendous promise. He quickly became Rick Ross’ lieutenant at Maybach Music Group, got signed to Roc Nation, and had endorsement deals with SkullCandy and Puma. Unfortunately, recidivism plagued his livelihood—making it difficult to escape the prison pipeline. His albums titled Dreams and Nightmares (2012) and Wins & Losses (2017) reflect his bittersweet reality.

Since his release from prison in April however, it’s been more about dreams and wins. The $15 million will help pay for lingering legal fees (now totaling $30 million over the course of his life). This money will also help him pay back wealthy friends like Philadelphia 76ers owner Michael Rubin and Jay Z who helped cover those fees.

While Meek Mill’s resurgence is captivating, the work is not done. He’s still skating on thin ice. “I get off probation in 2023. If I was to loiter or get a traffic ticket, I could go to jail for years,” Meek recently said on The Tonight Show Starring Jimmy Fallon. He also needs more consistency. The 31-year-old rapper needs business opportunities that will support him long after his criminal justice story is told.

“[Meek Mill] will be richer in two months when he comes back than he was in his whole career.”
– Boosie Badazz

A profitable story

Soon after Meek Mill was sentenced in 2017 (originally for two to four years), the hip-hop community expressed its outrage. #FreeMeekMill was both a call for change and a cause for concern. Fans feared that Meek would follow in the footsteps of fellow Philly rappers Cassidy and Beanie Sigel. Those two rappers rose to popularity in the 2000s, but got jammed up at the worst possible times—stalling their momentum.

While Jay Z, Beyoncé, and other artists were “in the hood hollerin’ Free Meek,” Baton Rouge rapper Boosie Badazz (formerly known as Lil’ Boosie) wasn’t sweating it. Shortly after Meek’s sentencing, the “Wipe Me Down” rapper predicted that Meek will be just fine. Here’s what Boosie said to TMZ:

“He’ll probably do like 10 months over that…Even though it was some bullshit, [Meek Mill] gonna be back even stronger…He’s gonna miss a lot of money, but he gonna get that double back. He’ll be richer in two months when he comes back than he was his whole career, just like that.

…

When you get that hype about coming home, people wanna hear what he’s gotta talk about, what he went through. All that money he’s supposed to be losing, he’ll come and get that shit right back.”

Media outlets thought Boosie was wildin’, but the 35-year-old rapper spoke from experience. He served five years for drug and gun charges from 2009 to 2014. Upon his release, Boosie did a short series with VIBE about his “reincarnation” after prison. His first album post-incarceration is his highest-charting to date. He also started a partnership with LRG clothing brand, wrote a book, and will soon be in an independent movie. It’s not a coincidence that Boosie’s opportunities were similar to Meek’s.

In addition to Meek’s Puma and Amazon partnerships, he also signed a two-year residency deal with Drai’s Nightclub in Las Vegas. He’s also recently performed at Summer Jam and Philly’s Made In America Music Festival. Meek has been staying busy, which is good for business and his personal well-being. He still fears going back to prison every day, so his busy schedule can help keep his mind at ease.

But at some point down the road, the public interest in Meek’s saga will end. It’s difficult for any story—regardless of its merit—to maintain lasting coverage in today’s media landscape. It’s great that Meek is working closely with Rubin and New England Patriots owner Robert Kraft to reform the criminal justice system, but Meek still needs to set himself up for the future.

Generating support for the (surprise) album

Meek has already started promoting his next album. On Monday, he told the New York Post that it will be a surprise album (partially ruining the surprise, but whatever). On Tuesday, he tweeted that he “will be joining the hottest albums of the year convos soon.” When the album drops, Meek should execute a strong rollout plan. As Travis Scott proved with Astroworld, influential support can boost album sales.

The best person to help Meek’s album promotion is actually his former adversary, Drake. The Toronto rapper has profited off Meek’s back for several years now. Meek has been a foil to amplify Drake’s brand—from the “Back to Back” diss record three years ago, to Meek’s guest appearances at Drake’s concerts just three weeks ago. It’s time to return the favor. The least Drake can do is hop on a guest verse.

In 2019, Drake and Meek should consider dropping a joint mixtape or co-headlining a tour. They can time the release with Meek’s Amazon docu-series to build demand. Meek would finally get a piece of the bankable Drake machine that he inadvertently helped create.

Meek will also get a promo bump from the increasingly strong Puma machine. This summer, the company put out a teaser video for the rapper’s newly released EP Legends of Summer and hosted a pop-up shop at the Made In America Music Festival, where customers who purchased an item were eligible for a free download of Meek’s upcoming album.

Puma can continue the “free download” offer by tying it in with the sneaker sales of the company’s two newly signed NBA rookies—#1 pick DeAndre Ayton and #2 pick Marvin Bagley III. The company has officially stated that it wants to strengthen its basketball brand through culture and partnerships, so this would be fitting.

In February 2019, Puma should strongly consider hosting a hip-hop inspired event at NBA All-Star Weekend, similar to the adidas 747 Warehouse event. These events are a showcase for new apparel, a cash grab for concession sales, and a performance opportunity for artists. Kanye and Kid Cudi were headline performers at the adidas event in Los Angeles this year. Meek can do the same for Puma.

Deeper than rap

Meek’s prison reform work with Rubin and Kraft will naturally lead to motivational speaking offers. Those opportunities should be welcomed, but the real money move is for Rubin and Kraft to help Meek establish strong businesses.

There’s already an interest on both sides. “In a lot of ways, Meek reminded me of myself because he kept asking me business questions. He started asking me questions like crazy because that’s the way I’ve learned and grown,” Rubin said on The Tonight Show starring Jimmy Fallon.

Rubin made his riches selling e-commerce goods. He can help Meek jumpstart Bikelife Junkie, the dirt bike-inspired apparel brand that currently offers a few limited items on Meek’s website. Rubin can help Meek strengthen Bikelife’s go-to-market strategy and develop a plan to tap into a niche but likely lucrative dirt bike apparel market.

Kraft on the other hand, is involved in several industries including real estate. The Patriots owner could help Meek assess real estate development opportunities in Meek’s hometown of Philly, where the rapper’s own neighborhood is changing quickly.

Both e-commerce and real estate businesses allow Meek to earn money in Philly, hedging his income in case he ends up on house arrest again and can’t go on tour.

#FreeMeekMill is not over. True freedom comes when Robert Rimeek Williams is off probation and is no longer associated with ‘Inmate #ND8400’.

Five years from now—when Meek’s probation is over—he can finally put this nightmare behind him. When that day comes, Meek should celebrate harder than he ever has before. It will be hard to top his April release, when Rubin picked him up in a helicopter and brought him to the Sixers playoff game.

But knowing Meek Mill, the ultimate celebration will be riding his dirt bike and popping a wheelie in peace.

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