We can’t tell the story of hip-hop without mentioning Diddy and the record label he started. Bad Boy took off in 1993 after Puff was fired from Uptown Records. He brought TheNotorious B.I.G. with him from Uptown Record, and signed a 50-50 deal with Clive Davis’s Arista Records, and it was off to the races.Bad Boy survived the tragic fallout of the East Coast vs. West Coast rivalry, and reached even bigger heights after Biggie’s death. Puff began to rise as a solo artist, but did the rest of the artists suffer as a result?Friend of the pod, Zack O’Malley Greenburg, joins me on this episode to cover 30 years of Bad Boy Entertainment. Here’s what we hit on:0:35 Sean Combs come-up story5:16 Diddy breaks in with Uptown Records8:22 Starting Bad Boy Records14:11 What sets Diddy apart21:04 How Diddy controlled the narrative23:58 Bad Boy’s formula for success 29:00 East Coast vs. West Coast rivalry30:39 Bad Boy’s historic 1997-98 run45:42 Bad Boy curse?48:44 Diddy’s reputation compared to Cash Money54:50 Best signing? 55:19 Best business move?57:19 Best dark horse move?1:00:19 Missed opportunity?1:08:52 Possibility of biopic?Listen: Apple Podcasts | Spotify | SoundCloud | Stitcher | Overcast | Amazon | Google Podcasts | Pocket Casts | RSSHost: Dan Runcie, @RuncieDan, trapital.coGuests: Zack O’Malley Greenburg, @zogblogThis episode is sponsored by DICE. Learn more about why artists, venues, and promoters love to partner with DICE for their ticketing needs. Visit dice.fmEnjoy this podcast? Rate and review the podcast here! ratethispodcast.com/trapitalTrapital is home for the business of music, media and culture. Learn more by reading Trapital’s free memo.TRANSCRIPT[00:00:00] Zack Greenburg: Diddy's ability to sort of walk the line and step back, you know, I think that's what ultimately kept Bad Boy in the position that, you know, that stayed and kept him in the position that he continued to be in.[00:00:09] Dan Runcie Outro Audio: Hey, welcome to the Trapital Podcast. I'm your host and the founder of Trapital, Dan Runcie. This podcast is your place to gain insights from the executives in music, media, entertainment, and more who are taking hip hop culture to the next level.[00:00:35] Dan Runcie Guest Intro: Today's episode is another case study style breakdown, and this time we chose to dive deep on the one, the only Bad Boy Entertainment when it comes to branding and when it comes to marketing. I don't know if there's another record label that has as identifiable as a sound of vibe as bad Boy, you knew what that vibe was.Puff said it himself, they take hits from the eighties, but do it sound so crazy? And that was the formula, and it worked time and time again. What Puff did was smart, it was a modern approach to how Berry Gordy approached the record business with Motown. But then he put his own spin on it, interning with Andre Harrell at Uptown Records, learning from him and then putting his own spin on it even more, making it relevant for the 90s and truly becoming the icon that was synonymous with shiny suits with that Bad Boy flavor.And so much of the success of one of the best MCs ever, the Notorious BIG, some of the most iconic R&B groups at the time, and singers such as Faith Evans, 112 and many more. And plenty of artists that unfortunately also had plenty of challenges and issues when it came to payment, drama, legal disputes and more.And we dive into all of that. I'm joined again by Zack O'Malley Greenburg. He wrote a book called Three Kings, where he dived deep into Diddy, as well as Dr. Dre and Jay-Z in this book, so he's well-versed and shared a bunch of great stories in this one. So let's dive in, really excited for this one. Hope you enjoy it.[00:02:06] Dan Runcie: We are back to talk about the wondrous world that Sean Combs built himself Bad Boy entertainment and joined by the one and only Zach Greenburg. Welcome back[00:02:15] Zack Greenburg: Oh, thanks for having me, Dan.[00:02:17] Dan Runcie: Bad Boy is so fascinating