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Startup City: Veterans turned entrepreneurs

Michelle Waite



April Caldwell (in black at the table), CEO of fayVen, recognized the challenges that small businesses, artisans and others faced in finding and booking the right venue to sell (when she had a craft popcorn business). Photo provided.

Veterans Day was this past Friday, Nov. 11. My younger brother Neil was in the U.S. Air Force for his first six years after high school, including time in the Middle East during the early ’90s. As I was researching and writing this article, I realized that I never officially thanked him for his service. But, I will. I am truly grateful to Neil and all of the others who are called to serve our country both locally and abroad. 

This includes a couple of Tampa Bay-based founders who I serendipitously interviewed on the same day a few weeks back for this Startup City series. April Caldwell, CEO of fayVen, and her co-founder and husband Aaron served in the Air Force for 10 and 20 years, respectively. You’ll get to hear their story later. Jim Bourie was a Parachute Infantry Officer and Special Forces Commander for the Army and is now the CEO of Torchlight AI, a platform for providing predictive intelligence for emerging risk around the world.

After serving in the military, my brother Neil went on to get his undergrad and MBA degrees, and he is now a real estate associate broker in Minot, North Dakota. 

What all of them have in common at varying levels and within different industries is an entrepreneurial journey post-military. It makes total sense. Many of our veterans are still young and have a long career ahead of them. In addition, the U.S. armed forces provides countless opportunities for them to learn, solve complex problems and become better leaders – all leading indicators of a strong founder.

I believe that a strong startup community supports and leverages the inherent and learned strengths of all of our multifaceted entrepreneurs, including those who served in the military.

A great place for veterans starting businesses 

Interestingly, in 2022, the Tampa Bay area was ranked No. 2 on the list of top emerging cities and No. 12 overall for veteran entrepreneurs, in a study done by the PenFed Foundation. According to their press release, the study analyzed four main categories for each city, which included livability, economic growth, support for veterans, and ability to start a business. 

We have many examples in our own backyard of successful veterans turned entrepreneurs. Hugh Campbell is one such local success story. After nearly 15 years of service in the U.S. Army, Air National Guard and Air Force Reserve, he jumped over to the tech industry. Eventually, he became the President and CEO/Co-Founder at AC4S where he leads today. If you want to hear his full story and how he made the transition to tech entrepreneurship, check out this podcast from Florida Funders.

Besides inspirational stories like these, there are also plenty of resources for our local veterans to explore and thrive in their own entrepreneurship. These include:

  • Startup Training Resources to Inspire Veteran Entrepreneurship (STRIVE), a national program offered through Syracuse University that was launched at the Hillsborough Community College in recent years.
  • Action Zone whose services are designed to help Veterans, Active Duty, Reservists, Guards and military spouses and dependents build businesses.
  • Bunker Labs provides community, programs, and courses to help military veterans and military spouses start and grow successful businesses and startups.

All of these programs are designed to support our Tampa Bay-based veterans to start and run their own startups. 

A platform to help small businesses sell

April Caldwell and her husband Aaron know well the value of local resources for veterans building their own businesses. Both are deeply active in their community and the organizations listed above.

In 2019, the Caldwells moved to Tampa Bay from Austin, Texas where their entrepreneurial journey had begun running a small business selling gourmet popcorn at local venues. It was during this time and through personal experience that the idea for fayVen was born.

“We always kept running into the same issues,” explains April. “Either not finding the right demographic or crowd to sell our popcorn to, or paying a ton of money for an event that didn’t have any foot traffic or ROI.” They even tried to secure a physical retail space and got turned down for various reasons on three different occasions.

They began testing a new model that seemed to have traction. After approaching local breweries and other businesses, they would secure a space outside or within these locations and set up shop. They would sell out of product almost every time because “popcorn and beer go together well.” This was their “aha” moment.

 “We realized there were synergies like this that probably exist in other realms as well,” states April. In addition, they recognized that within the standard practice of booking a table for an event or other venue, it was extremely inefficient with a lot of redundancy in the application process for both the vendor and the venue.

fayVen is the online platform that creates the connections between vendors and venues to make booking easier and safer. The Caldwells’ mission is to provide mobile, home-based vendors and artisans the opportunity to sell their products and services in their communities and beyond. At the same time, the venue owners are able to generate additional revenue streams by leveraging their physical space for small businesses that are complementary to their own.

Still in its early phase, they have more than 15 events under their belts including a recent collaboration with Synapse and Hotel Haya in Ybor City to help support those impacted by Hurricane Ian in Southwest Florida. 

April has a special place in her heart for Florida. She was born in South Florida and raised in the northern part of the state. After living in California and Texas, she and her husband eventually landed back in Florida, specifically in Tampa Bay, in 2019 to be closer to family.

“It was time to come home for us,” states April. “Tampa Bay has been so welcoming and great as far as the ecosystem – so well connected. Every entrepreneurial community knows about the others and can connect you with somebody in those different communities. It has boosted our ability for finding the resources that we need.”

In fact, after graduating from the Tech Women Rising cohort of the Tampa Bay Wave in December 2021, they were able to better craft their pitch and win two separate competitions to help fund the venture. 

April is especially excited about the potential for St. Pete as they launch their business here. “St. Pete is the most ideal place to launch fayVen because of the artists and the artisans in the community,” she explains. fayVen will help them expand their reach beyond the local region in Florida and beyond. 

That’s a lot to be grateful for. Thank you to all veterans for your service. And, thank you to all of the leaders in the entrepreneurial ecosystem in Tampa Bay helping veteran-owned companies thrive. 

Startup City will continue to explore topics on what it takes to have a thriving startup ecosystem through stories and thoughts of local residents and startups. 

Michelle Waite is the VP of Marketing at Florida Funders, a locally-based venture capital firm and angel investor network who enables tech startups to thrive through monetary and business-intellectual capital. She has invested in, co-founded and worked for tech startups for the last 10 years. She counts herself lucky everyday to work for and alongside some pretty amazing entrepreneurs. You can follow her on Twitter or LinkedIn.

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