Maurice Thomas

How my 15-year side hustle became my lifelong dream

Maurice ThomasContributed by Maurice Thomas, an EO South Florida member who is one of the Champions of the new EO OneWorld initiative, a membership platform affiliated with EO’s New York chapter which believes that a diverse EO is a stronger EO. EO OneWorld will add value to EO by attracting more EO members from the Black, Hispanic/Latino(a)(x), Asian and LGBTQIA+ entrepreneurial communities. Maurice is also the founder and president of Thomas Services, Inc. a solutions-based, logistics and supply chain service company.

Are entrepreneurs born or made? As I examine my path to entrepreneurship, I suspect it’s a little of both, or at least it is in my case. Here’s the story of how I came to run my own company.

Back in the early 1990s, I was a married father of two very young children working as an investment banker in a small, boutique firm. Our firm’s owner and CEO was a very experienced businessman—a true entrepreneur in every sense of the word. Having previously worked in some of the largest companies in the world and earned an MBA from a prestigious university, I had no idea what I signed up for, but it didn’t take me long to realize that working there was the best professional decision of my life. We were small and very entrepreneurial in our approach. I was required to learn very quickly, and I was given increased responsibilities no sooner than I showed the capacity to handle them. 

My first entrepreneurial opportunity

One day in early 1993, I was having lunch with one of our clients, who also was a true entrepreneur. He began to describe his latest business acquisition and—suddenly!— the conversation morphed into a discussion around the opportunity for me to start a business designed to service HIS new business. A few months later, I was the owner of a modest, three-employee operation. And so, my entrepreneurial journey began.

This new business wasn’t of a scale sufficient to support my “lavish” lifestyle (i.e., pay my mortgage and feed my family).  It was just a profitable side-hustle, and it remained that way for years while I continued to work full-time as an investment banker. 

I often found myself fantasizing about winning new contracts, scaling the operation, and turning my little side hustle into a full-time business enterprise. However, for years, this remained as just a dream. It was apparent to me that, for my “fantasy” to become reality, I would have to quit my job and jump in with both feet, something I couldn’t afford to do with a young family to support.

Taking the plunge  

Fifteen years later, as a divorced dad of two teenagers, I found a window of opportunity.  I analyzed my financial circumstances and calculated how much time I would have to “make some hay” before my personal finances would come crashing down around me. Shortly after completing this exercise, I quit my job and devoted my full-time effort to growing my now 15-year-old side hustle.

An unexpected challenge

Three months into my new life as an entrepreneur, we lost our single largest of only three business contracts—and the amount of time I had to “make hay” shrank by 50 percent. Suddenly, I faced the most difficult of decisions:  I could return to the world of working for someone else or continue the challenge of making something significant happen in a very short period.

Doubling down

I decided to roll the dice, take out a second mortgage on my home and go for broke. Many nights, after a day of working hard but not moving the needle, I questioned whether I was doing the right thing. I kept coming back to the same answer: YES!

The payoff

A few months later, while on a business development call and literally “stalking” a business prospect, I stumbled onto an opportunity that changed the trajectory of my little company. 

I relentlessly pursued the deal, and less than a year later, I was running a 55-employee operation in a niche sector of the gaming technology services space.  We built a first-class service team and an impressive operational infrastructure, all based on a vision and a core philosophy that continues to be my guiding light in all matters business and personal.

Another roadblock

Nine years after that meteoric rise, our client lost a major contract—the very same contract upon which we had built our entire business operation.  Because of market forces far beyond our control, we were forced to institute a massive layoff.  Once again, I faced a significant change in my business life.  


This time, I found myself very close to retirement age and able to call it quits.  However, because I discovered that I have a true passion for entrepreneurship coupled with a strong self-belief, I decided that I was not ready to throw in the towel.  So, now, in addition to designing a strategy to resuscitate my 28-year-old company that I started from scratch, I’m also considering “acquisition entrepreneurship” and currently evaluating the prospect of buying and building another, existing company. 

And so, the journey continues. Along the way, I’ve learned valuable lessons that may benefit others wondering whether they’re ready to take the plunge into entrepreneurship.

4 Entrepreneurial lessons learned

  1. Expect the unexpected. Things will likely get more difficult before they get easier.  Be prepared to respond to unanticipated challenges that you will inevitably face.
  2. Self-belief is absolutely critical.  You must believe that nothing and no one else is more worthy of the “gamble” than YOU.
  3. See yourself for who you truly are.  Be critically honest with yourself. Conduct a personal SWOT analysis (strengths, weaknesses, opportunities, threats) and take the results to heart.
  4. The benefits are well worth the risks. Entrepreneurship is a unique and incredibly satisfying path toward personal growth, leadership development, personal financial gain, and many other worthwhile life achievements.

Categories: Entrepreneurial Journey general Inspirational members


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