Sean “Diddy” Combs is one of hip-hop’s most serial entrepreneurs. His business track record stretches 30 years with successes in completely-different industries — music (Bad Boys Records), clothing (Sean John), spirits (Ciroc and DeLeon), media (Revolt), among many other ventures. To take a closer look at Combs’ empire, I brought on Tarik Brooks, who is the president of Combs Enterprises.

Many chalk up Diddy’s entrepreneurial success to his influence and brand alone. While Tarik doesn’t deny Diddy’s star power, he also argues that line of thinking understates Diddy’s business acumen — his ability to spot trends, attract talent, raise capital, and so forth.

Not only that, but the broadness of Combs Enterprise is a unique competitive advantage. Diddy’s different businesses across sectors give them unique data points that can drive decision-making. The group announced a new foray into cannabis in late 2022. However, they won’t enter the space completely void of knowledge. Using insights from Revolt or Ciroc, they can glean how customers think about cannabis already.

Tarik and I dove deep into Diddy’s sprawling business empire this episode — the “why” not the “how” behind Puff’s success. Here’s what you can expect to hear:

0:53 Combs Enterprises’ focus in 2023
1:48 Synergies between Diddy’s different businesses
4:30 Using Revolt Summit as a testing ground
6:36 Origins of the “Ciroc playbook”
9:18 How much strategic overlap is there between Ciroc and DeLeon marketing?
15:42 Entering the cannabis space
22:17 Regulatory challenges in the cannabis industry
26:32 Why Diddy is not just another celebrity entrepreneur
32:22 How Combs Enterprises invests in startups
35:32 Did Diddy really back Elon Musk’s purchase of Twitter?
37:33 No rush to sell Bad Boy Records catalog
42:56 Sean John comeback
46:41 Diddy’s attempt to buy the Carolina Panthers in 2018

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