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bad boy for life

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Hey! It’s been a busy week with all the catalog sales and startup rounds closing before the end of Q2. Logic, The Spinners, and Kool & The Gang have all been in recent deals. WAVs AI, Snafu Records, and Jaxsta have also raised recent rounds. I bet we’ll see a few more tomorrow.

​This week’s episode of Trapital is our breakdown of Bad Boy Entertainment. It’s the next podcast in our case study series. I’m joined by Zack O’Malley Greenburg, who wrote 3 Kings and shared several stories from his work for that book.

Ironically, we talked about Diddy this week since he cut ties with Diageo, the parent company of Diddy’s spirits brands, Ciroc and DeLeon. It will be fascinating to see how it plays out.​

Ready to take a trip back to the 90s and revisit what set Bad Boy apart? Let’s dive in.

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the bad boy - motown comparisons

Puff Daddy’s Bad Boy Entertainment and Berry Gordy’s Motown Records have been compared countless times, but let’s dig into that.

Motown created a new genre. Gordy convinced the industry gatekeepers that music made by Black artists wasn’t just for Black people. There was a formula, and it worked.

Bad Boy also had a distinct sound, but several 1990s record labels did too. Death Row Records did the same with G-funk. So did Cash Money, No Limit, LaFace, and So So Def. They all had in-house production teams that turned soul samples into modern anthems.

The real tie between Motown and Bad Boy is the ability to maximize derivative work.

When Marvin Gaye’s “Ain’t No Mountain High Enough” became a hit in 1967, then ran it back three years later with Diana Ross’ version, and it became an even bigger hit. The Jackson 5 did several successful Motown covers. Motown would even have the same artist do two different versions, like Martha and the Vandellas’ two versions of “Jimmy Mack.” The list goes on.

Bad Boy did the same with remixes. It’s debatable whether Bad Boy actually invented the remix, but the hits delivered. When Puff was at Uptown Records, he turned Mary J. Blige’s “Real Love” remix into a completely different song featuring The Notorious B.I.G. Years later, Craig Mack’s “Flava in Ya Ear” remix was the song that closed the deal for Bad Boy and its 50-50 deal with Clive Davis’ Arista Records.

Bad Boy had a similar approach with its “Part 1” and “Part 2” of songs like Busta Rhymes’ “Pass The Courvosier” or Diddy’s “I Need a Girl.” That formula had Berry Gordy’s name written all over it.

If Gordy and Combs built Motown and Bad Boy today, they would be all over AI music. There would be an AI artist named “Marvin GAI” with its own spin on “What’s Going On.” Bad Boy would have created an AI artist named “MAIse” to replicate the real Ma$e. It was all inevitable.

​You can listen to the episode here or read below for more highlights.

building something bigger than yourself

Here’s an excerpt from Puff’s 1997 interview with The Los Angeles Times:

This move became a blessing and a curse.

The blessing is that Bad Boy reached greater heights in the immediate years after Biggie’s death. Biggie’s Life After Death—released 16 years after Biggie’s death— went diamond. Puff Daddy & the Family’s No Way Out went 7x platinum. And Ma$e’s Harlem World went 4x platinum. Puff was on top of the world in 1997.

By summer of 1999, Bad Boy had sold more records in that fiscal year than Madonna’s Maverick (during her “Ray of Light” era) and more than Def Jam when DMX and Jay Z were on top.

But as Puff’s star rose, the rest of the Bad Boy roster took a backseat. Faith Evans and 112 wanted off the label and had rumored financial disputes. Mase has been at odds with Puff for years over financial disputes. Other artists like Shyne, G. Dep, and Loon had legal troubles. By 2002, the only Bad Boy artist with platinum success was Puff himself. Despite a few bright moments, like Diddy’s Press Play, Danity Kane, and “I’m Coming Home,” the label couldn’t recapture that 90s glory.

In hindsight, Bad Boy’s journey was inevitable. Puff has always been a brilliant marketer. His biggest skill is marketing his own lifestyle. He did it with artists like Jodeci (at Uptown), 112, and Mase. They were modeled as extensions of Puff. He did it with female artists like Faith Evans, Total, and Cassie (who eventually became his long-term partner). And he did it with products like Ciroc and Sean John.

That mentality can scale consumer products, but it’s hard to scale creative talent with the same longevity. Puff did it well with his own artistic brand, down to the frequent name changes, TV shows, and guest features. But without another Bad Boy leader as his peer, who isn’t “all in the video” and can think beyond the flagship artist, there are only so many resources to go around to develop an entire roster.

It reminds me of my conversation with Dreamville’s CEO Ib Hamad. I asked him how the label separates its brand from J. Cole. It’s hard as hell to do, especially today, but it helps that Ib isn’t also trying to build his own artistic career.

It’s no different than a startup with a technical co-founder and a front-person as the other co-founder. Doing both isn’t impossible, but it’s not easy.

a “what if?” for Bad Boy and Roc-a-Fella

The first single that The LOX released on Bad Boy was “If You Think I’m Jiggy.” Please take a minute and listen to this track.

It’s a decent song but not the right fit for Jadakiss, Styles P, and Sheek Louch. It was an attempt to fit The LOX into that Bad Boy brand. This is why Kanye West said, “I feel like Bad Boy street team, I couldn’t work The LOX.”

The LOX eventually left Bad Boy. Jadakiss and Styles P dropped successful solo albums, and it all made more sense. This is what these emcees should have been on the whole time.

On the podcast, Zack brought up a great point.

He said that there should have been a record label trade: Bad Boy should have traded The LOX to Roc-a-Fella in exchange for The Diplomats. Songs like Cam’Ron’s “Oh Boy!” and “Hey Ma,” or Juelz Santana “Oh Yes” made a lot more sense with Bad Boy’s swagger. Meanwhile The LOX had more in common with the grittier, State Property, Hard Knock Life vibes that Roc-a-Fella had at the time.

The music business doesn’t work like that, but what if it did? Who says no to that trade?

It would have added a whole new element to the LOX vs Dipset Verzuz battle.

Those are just a few topics we dive into in the episode. We also discussed:

• lessons learned from Uptown Records’ Andre Harrell
• the impact of east coast vs west coast beef on Bad Boy
• the money made and the deals signed

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money moves

• ​global music market will be worth $151.4B in 2030 according to Goldman Sachs report
• the big business of family touring entertainment​
• why music streaming can’t agree on a payout model​
• ​an interview with Marc Andreessen about AI and how you can change the world

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coming soon from Trapital

Podcast: Is hip-hop really in decline? The media is running wild this narrative, but we wanted to dig into this a bit more. I’m joined by Neil Shah from The Wall Street Journal. Drops next week!