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3 Key Entrepreneurial Lessons I Learned While Working for P. Diddy and Bad Boy Entertainment Here's what I learned after becoming a "bad boy" and working for P. Diddy — and how I've applied these lessons to my own personal development and entrepreneurial journey.

By Justin Vandehey

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

The only thing I love more than sports is music, more specifically the art and science of music production and the business of music and entertainment. In fact, in the process of completing my University degree in business, I enrolled in community college courses to learn the basics of audio engineering and music production. I wanted to be a music mogul. I wanted to be P. Diddy.

So, one afternoon while browsing the music catalogue of the Notorious B.I.G., I stumbled upon the careers page for Atlantic Records and Bad Boy Entertainment. There was a newly posted opportunity: Join Bad Boy and Atlantic Records international marketing team.

I knew my odds of getting the gig were low, but I said screw it, "what would Puff do?"

One week after submitting my application, I heard back from a recruiter who said the hiring manager liked my content samples as a beat writer for a Fantasy Football website. He also needed help building out his fantasy football roster. I got the job.

That next day, I notified the registrar that I was taking a leave of absence after my Spring Semester and dropping out to move to New York to become a music mogul.

This is what I learned in the process of working for P. Diddy and Bad Boy Entertainment — and how I've applied these insights to my own personal development and journey as a professional and entrepreneur.

Related: From Paper Boy to Music Mogul: Entrepreneurship Lessons From Sean 'Diddy' Combs

Land and expand

Before joining the label, I had a very limited view into all of the alternative revenue streams that existed outside of the music catalogue. I assumed the majority of artists made their fortunes from their work in the studio. However, it became clearer to me that the music was the catalyst for building a brand that transcended Billboard charts.

Obviously, the music had to be incredible; However, Diddy was one of the first to extend the value of his brand into other categories that have made him a billionaire, such as fashion, media and alcohol. He was able to build thriving businesses that were connected to his brand persona. What's more, he invested time and energy into businesses he understood. The intersection of those two forces had compounding effects.

I now apply this model to every new opportunity I evaluate or take on. I know that I have experience in enterprise SaaS sales with a passion for company building at the earliest stages. It's what led me to start my podcast, it informs which companies I invest in and advise, and it'll ultimately help influence which company I build next.

Whether you're a music icon or a business-to-business SaaS founder, once you've mastered your craft and established a brand persona and reputation in your space, diversify your channels of impact by expanding into connected categories in the domains that you know well.

Related: Lessons on Innovation and Evolution From 3 Top Hip-Hop Artists

The muffins matter

During the release of Making the Band's solo artist Donnie Klang's album, "Like a Rolling Stone," I met P. Diddy for the first time. Diddy hosted a release party in Atlantic Record CEO Craig Kallman's office, and I was there to represent International Marketing.

Diddy sat in the middle of a room as the entire album played from start to finish on the giant tower speakers. He listened to every track, barely able to keep himself from dancing out of the chair. At the same time, he critiqued every track and every lyric, while he surveyed the room to see the impact that the music and the environment were having on his audience.

Twenty minutes in, he pointed to the sky and asked to stop the music. He looked over in my direction and asked one of his assistants, "Who's the guy by the breakfast table?" I introduced myself, to which he replied, "Breakfast is the most important meal of the day. This room needs some #$#% muffins." Following the breakfast incident, later that day, I remember seeing a copy of a press release with Diddy's approval on it for the album to ensure that the quality was up to his standards. His attention to the details and involvement in so many of the seemingly smaller decisions are what stuck with me.

As entrepreneurs, we are often faced with the question of how to "run the business" without being "run by the business," as well as when to delegate or take ownership in order to scale. Personally, I struggled with this when we were attempting to scale our sales efforts at my company, Disco, and ultimately realized that I needed to be more heavily involved in the direct selling effort to ensure that our brand, positioning and message were on point with the story we were selling.

If you're hosting a party, make sure the party is awesome before you decide to leave the room. If you want the party to remain awesome, the details matter. Even the muffins.

Related: When Should a CEO Get Involved in Day-to-Day Details?

Keep reinventing yourself

Sean Combs has taken on many identities in his lifetime — Puff Daddy, P. Diddy, Diddy, and most recently, LOVE — all showcase the evolution, growth and maturation of a music icon, entrepreneur and father. Similarly, the music industry itself has undergone several evolutions and identity shifts. Retail sales were disrupted by digital distribution, which was enhanced through the improving infrastructure of the web and streaming.

Watching this play out in real time taught me that we're all a work in progress and that it's important to continue to evaluate our position to stay relevant but also true to ourselves.

After a year and a half in New York in an unpaid internship, bartending in NJ, cleaning up vomit to make ends meet and eventually losing everything I owned in an apartment break-in, I decided it was time to reinvent myself. To my parents' delight, I returned to college to finish my degree.

To be clear, my return to school wasn't just driven by the barrage of pastry requests I was getting at the label. After seeing what was happening in the business of music and the disruption occurring to their business model, I knew I needed to get closer to the source of where those services were being built. I felt like I could build relationships with a network of entrepreneurs working on the business I cared about.

Two months later, I interviewed for a job at Intuit. And to this day, I haven't eaten another muffin.

Here are a few points to summarize what I learned from working for P. Diddy and my experience as a "music mogul."

  • Land and expand: Once you've nailed your craft or created your niche, experiment with channels to extend your impact in connected categories that you know well.

  • The muffins matter: Great founders don't "run the business," but they do sweat the details.

  • Keep reinventing yourself: Don't be afraid to experiment and revisit your purpose or explore an alternative path that might help you get to the place you aspire to be.

Justin Vandehey

Entrepreneur Leadership Network® Contributor

Cofounder of Disco. Producer of the Bridge podcast

Justin Vandehey was the cofounder of Disco, the first company built on Slack & Microsoft Teams. In 2021, Disco was acquired by Culture Amp. He currently leads partnerships and business development for Culture Amp. He is an advisor for the Alchemist Accelerator & invests in early stage B2B startups.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

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