How You Know You're Supposed to Be an Entrepreneur (or at least how I knew)
Updated: Mar 29
When I was a kid, I sensed I was a little different than most. Sure, I enjoyed playing outside and playing pickup street hockey just as much as the next neighborhood kid but there was something I enjoyed more. Business. Whether it was running the rec basketball league snack bar or setting up the best lemonade stand in the whole town– I loved to be involved with business. I still remember this hot summer day and Paul the mailman pulled up to my stand. Visibly parched, he paid me $10 for ONE cup of lemonade and said, “keep the change kid”.
If I wasn’t selling lemonade in the dead heat of summer, I was going door to door, at 10 years old, and offering to wash my neighbors’ cars. Instead of spending the money I earned I put it in a brown paper bag and decided that I would save up enough money to buy a Corvette. I never did save enough to buy that car but subconsciously I was altering the framework of how I perceived the world.
I firmly believe my young entrepreneurial years led to a greater work ethic that I carried with me throughout my teenage years. Never a particularly studious teen, I was more focused on sports and working after school. I excelled in every job I held, until I got my first corporate job at age 19.
During my first two years of college, I interned at an “almost” Fortune 500 company in the Human Resources department. It was a fantastic experience that I thoroughly enjoyed. That is until I decided I would interview for a full time HR Coordinator position. I crushed the interviews and was eventually offered the role, with the contingency of continuing my education. I figured I could work through school and use the tuition reimbursement to pay for the rest of it.
Weeks into the job, though, I felt uneasy. I was an unproven 19-year-old kid thrust into the wild of corporate America. I hated the politics, the gossip, and my boss and I didn’t see eye to eye. The work was mundane and repetitive. I couldn’t have imagined doing this until retirement…so, I quit AND dropped out of school.
I left a secure job that I earned at 19, without completing a college education. Who does that?! Soon after I started my first business – a talent management and promotions company for local hip hop artists and models. Yes, you read that right. The Rhode Island country white boy was going to manage and promote rappers and make money doing it. It sounds ridiculous to me now, but I had always been a student of hip hop and I knew a lot of people that rapped, breakdanced, and modeled.
The first show I ever promoted happened in 2009 at The Black Rep in Providence, Rhode Island. I put out audition ads on Craigslist for the showcase. One rapper showed to the audition. Luckily, he was a super talented dude from Brockton, MA by the name of Eclipse. Along with Eclipse, we featured artists named J.P., Sapience, and Hard Hitta. All of whom had a following in their own right.
Once the lineup was set, I designed the flyers, got them printed and hit the streets. I spent days passing out flyers in Kennedy Plaza, in the club district, and around the many colleges in Providence. I think I sold 50 or so tickets in total.
The day of the showcase was here, my mom made appetizers for the “VIP” lounge, and I “hired” my 6’2’’ 275 lbs father and uncle to act as my bouncers. The show went off without a hitch and I knew I was never going back to corporate America.
Instinctually I think I always knew I’d work for myself. My venture in hip hop only lasted 2 years but for the next 10 years thereafter, I built businesses and tried my hand in many different ventures. My most successful being a mobile DJ business. Life was great, until COVID happened. I lost 100% of my income overnight.
I had never felt a depression so deep than when my business was ripped away from me. I no longer had a way to provide for my family. That’s when I said screw it. I’m done working for myself. I’m going back to the corporate world. So, I enrolled in college (again), finished my degree, and secured a position as Head of Marketing in the public safety industry.
At first, I loved the job. But just like my first go-around I quickly lost interest. Every day I drove 45 min one way to this job and every day felt like a dagger in my heart. Even though I had a great job title and made decent money, I felt unfulfilled. I made it 6 months before I quit that job and went back to build my businesses. Thankfully, business is now better than it was prior to COVID, and I have begun this new venture with 32One Media. I am an entrepreneur at heart, and I think I always have been.
My advice to you is this, life is too damn short to be stuck at a job you hate. If you are passionate about a business idea, pursue it. That burning desire to fervently pursue your dreams is how you know; you’re supposed to be an entrepreneur.