If you’re interested in sharing your opinion on any cultural, political or personal topic, create an account here and check out our how-to post to learn more.

As a youngster, I was always told that I could be anything I wanted to be. Nevertheless, coming from a family where education was of paramount importance, one could imagine that the esteemed careers of physicians, attorneys and engineers were always the direction you were typically pushed in. While the aforementioned career paths were certainly ones that I considered, I always naturally had a knack for entrepreneurship. From being a fifth grader facilitating raffles where tickets were 25 cents each, to being a teenager and selling Nike SB Dunks to adamant and overzealous “sneakerheads” at an aggressive 300% to 400% markup, it was quite obvious that entrepreneurship was the path for me. However, how does one go about pursuing a career as an entrepreneur?

At the age of 18, I enrolled in Binghamton University’s School of Management where I studied Business with a concentration in Marketing and Finance. I got my first hands-on experience as an entrepreneur when I became the self-appointed “resident barber” on campus, and later leveraged my love for music into a short-lived DJ career during my last two years of undergrad. College equipped me with a broad array of soft and hard skills (both inside and outside the classroom). Yet, I ended my tenure at Binghamton University without a full-time job offer. While friends and acquaintances threw a ton of negativity at me — “The economy is horrible so I doubt you will find a job.” “If you don’t have an offer at graduation, you will never get a job.” — I mustered up the strength to avoid letting the chatter phase me. Contrary to popular belief, you do not always have to have everything figured out. There are always suggested paths, but that does not mean if you deviate from the suggested path all hope is lost. As a spiritual person, I let my faith guide me in shattering the echoing voices of peril and applied for a role at JP Morgan Chase & Co., where I was later offered an analyst position and given my first taste of corporate America.

My time at JP Morgan was an amazing experience but I was unfulfilled, as the typical corporate career was of no interest to me. After a few years (going against the judgement of trusted colleagues and peers), I entered the human capital and recruitment industry. While there were “apprehensive supporters” (the people who wish you well but don’t necessarily understand your decisions), after learning about the rigorous, competitive and lucrative nature of the recruitment industry, I knew this was the ideal career path (for me), as it was reminiscent of the feeling one would get if one were to own his or her own business. During my first week, I made company history by making my first placement on my third day as a recruiter with the organization and became a top producer by the end of my first year.

With only two years of experience in the recruiting industry, I assumed a role as a director of recruiting, accounting and finance at Lloyd Staffing, where I was also a top producer and rebuilt their accounting and finance recruiting practice. During my tenure at Lloyd Staffing, I had my first experience on the “big screen” when I was asked to participate in Chris LaVoie’s Art of Recruiting documentary, where I was featured as one of the Top 20 recruiting and sales professionals in the world. While filming the documentary in Central London, I was introduced to illustrious members of the venture capital and technology industries. As a result, I forged a very strong relationship with the CEO of a Montreal-based venture capital incubator and firm. After a few years of correspondence and assisting with a few projects, I was eventually offered an opportunity to assist in building out their human capital portfolio, where I was responsible for identifying and vetting companies for potential incubation. It was at this moment when I began operating in an advisory capacity for CEOs.

When my tenure at Lloyd Staffing came to an end, I joined a former colleague in building a recruiting firm from scratch in the heart of NYC, just a stone’s throw away from Madison Square Garden. Again, I was faced with uncertainty, a new challenge and confused looks from friends and family. Nevertheless, I relied on faith to guide me. After two years, we grew organically (from just two hardworking recruiters) to being one of the most profitable recruiting firms in NYC with a headcount of 20 plus recruiters.

Shortly after the recruiting firm’s inception, I decided to get my feet wet with speaking engagements and spoke alongside Amol Sarva (co-founder of Virgin Mobile and Knotel) at one of New York City’s largest technology meetups, Harlem Tech Week. With one foot in recruitment and the other in venture capital, I eventually made my departure from the recruiting firm I helped build and took on a role as the Strategic Advisor to the CEO of VOMOS, an all-in-one on demand app for premium travel experiences. It’s a very difficult decision leaving an entity that you were so heavily involved in building, but it was time to take the next step in my career. At this point, the goal was to build out a portfolio of investments and my consulting/advisory business. Once again, facing looks of confusion from family and friends, I put my faith in God and his ability to guide me prior to moving forward with my new opportunity.

In my first few months with VOMOS, I recruited and hired the former Chief Operating Officer (COO) from Victoria Secret PINK who was a member of the original team of four that built the brand from $0 to $1B in revenue in five years, making it the fastest growing retail concept ever. Additionally, I assumed a role as the business manager to a well-known celebrity jet broker and entrepreneur, Kelvin “PJ Kev” Mensah.

In an attempt to diversify my interests across an additional industry, I acted as the initial angel investor in One Eight Consulting LLC, a celebrity styling concierge service being led by Sincere Armani (who is most widely known for her work as Nicki Minaj’s former stylist and as a former styling executive at Sean “Diddy” Combs’ Revolt TV).

During a trip to my parents’ “motherland” of Jamaica, my uncles and aunts offered me a role as a director on the board of my family’s tourist attraction Benta River Falls, located in the Westmoreland parish of Jamaica, just about 45 minutes from the island’s world-renowned Seven Mile Beach in Negril. The 28-acre tourist attraction boasts a mineral bath, lime exfoliants, a restaurant and bar, and some of the most beautiful fresh waterfalls in the Caribbean.

In more recent times, I have partnered with a serial entrepreneur from the Netherlands to spearhead the launch of a new and exciting concept in the United States – NakeFit. NakeFit (@nakefitusa) is an adhesive sole that protects the bottom of people’s feet and is revolutionizing the way athletes train, the way people enjoy spa days and also how the masses enjoy the outdoors (beaches, pools, amusement parks, etc.). We have made quite an impact in the United States since our launch in August 2019 and having some exciting initiatives planned for 2020.

I am currently involved with the daily operations of three companies, I act as the strategic advisor to four CEOs and run an executive coaching business. Much to the surprise of my colleagues, I am actually heavily involved in the music industry as well. For many years, I was always very discrete about my passion for music while I was in a professional setting because I wanted to avoid perpetuating any quintessential stereotypes. I’m sure you could imagine how many times I was told “everyone does music” and “you will never make it” as a youngster, but I couldn’t let anyone steal the joy I received from my favorite pastime, so I continued to create.

My fondest memories of music date as far back as 1997. When I was eight years old, I began playing the cello. Throughout high school, I was first stand and sectional leader (twice) for both the concert and chamber orchestras, eventually becoming a level five cellist. I leveraged my traditional classical training and love for hip hop, reggae, soft rock and R&B, into a part-time career in songwriting, A&R and executive production. I have been afforded the opportunity to work with legends like grammy-award winning Mikaelin “Blue” Bluespruce, grammy-award winning Caron Wheeler (who is most well known for her vocal and songwriting work with the hit single “Back To Life”) and multi-platinum super-producer K.E. On The Track (who is known for his production work with the hit single “Swag Surfin’”).

All in all, the most important takeaway that I have learned throughout life is that there is no definitive blueprint for success or accomplishing one’s goals. Furthermore, you have to allow your dreams to be bigger than your fears. If not, when exposed to naysayers you will easily lose confidence. Life has just as many setbacks as it has opportunities. Some people may take a more conventional approach toward life and have a well laid out plan – they deserve kudos for this. However, remaining malleable and adjusting accordingly to what life throws at you will open doors, as opposed to just pushing you through only one. While life is not a race, a culmination of faith, skill and perseverance is all that is needed to successfully make it to the finish line.

Aaron Wilson

Writing since October 2019 · 1 story contributed