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Conversations with Stephen Sherman

Today we’d like to introduce you to Stephen Sherman.

Hi Stephen, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
During the Covid-19 Pandemic, I noticed the Heads and Tails had gone up for sale. Living in Beach Park, I had visited this specialty store many times for Florida Gator gear. My medical device distribution business came to screeching halt and all of the sudden found extra time on my hands. I reached out to my business partner of 20+ years and told him I was interested in buying the business. His initial reaction was, “Are you F’ing nuts? You want to buy a brick and mortar store in the middle of the largest pandemic in a century with no sporting events occurring?” My response was emphatically, “YES!” I couldn’t see this gem of a store go out of business when it is the only independent sports apparel and gift store left in the area. Fast forward a few months and we indeed did purchase Heads and Tails! Three families became the third ownership group for the store that originated in 1992. We are all graduates of Florida, Florida State, and USF and have a great passion for our alma maters. In addition, Champa Bay has had one heck of a year! Tom Brady, Rob Gronkowski, Super Bowl LV, Stanley Cup Champions and a birth the World Series. The Bucs, the Lightning and the Rays are on fire! We are excited to see what the future holds for Heads and Tails!

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Covid-19 has been our biggest struggle. Without mass attendance to sporting events, people are not spending their time and money investing in apparel and gifts to support their teams. Many people are still not comfortable shopping in retail locations. Having not worked in retail prior to purchasing the store, we are learning a lot along the way.

Thanks – so what else should our readers know about your work and what you’re currently focused on?
We are entrepreneurs, through and through. We are risk takers that like to have a good time along the way. In my medical device distribution business, we look at trends in the market and try to capitalize upon them while providing products and services that enhance patient care. Heads and Tails is just the same. We strive to provide the best, unique products that are available in sports apparel and gifts. We are trying to provide our customers with an experience each and every time they walk through our doors. Sports bring people together and unify a community no matter your gender, race, creed, or sexual orientation and we love that!

Any advice for finding a mentor or networking in general?
I have many mentors in my life including my grandfather, father, business partner and others in my professional network. I learned at a very young age from the most influential three men in my life listed above that you do whatever it takes to get a job done. These men taught me that you should never be too proud to do any job that needs to be done in your organization. Never become too big for your britches and treat everyone with respect. You never know who you might come in contact with. From a networking perspective that is the best lesson. You are always just a few people away from the person you need to take you to the next step in your career or business.

Contact Info:

  • Email:
  • Website:
  • Instagram: the_heads_and_tails
  • Facebook: @HeadsandTailsTampa

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