Veteran Entrepreneurship: Reflections from UConn’s EBV Alumni Weekend

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  Event Program with Featured Speaker Jose Samayoa

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  Jose Samayoa presenting during EBV Alumni Weekend

This past weekend, I had the opportunity to serve as the featured speaker at UConn’s Entrepreneurship Bootcamp for Veterans (EBV) Alumni Weekend.

The room was filled with veterans who had already served something bigger than themselves, transitioned into a completely different chapter of life, and then made the decision to build something of their own.

That is a group I have a tremendous amount of respect for.

The Entrepreneurship Bootcamp for Veterans, or EBV, is designed to support veterans through the realities of entrepreneurship and small business ownership. UConn has participated in the program since 2009, providing practical training, mentorship, resources, and a community that continues well beyond the initial program.

I’ve been fortunate to get closer to that community over the last couple of years.

In 2025, I participated in UConn’s EBV Alumni Event as a speaker and pitch competition judge. Earlier this year, I joined CCEI for an episode of its Timely Topics podcast to talk about entrepreneurship, leadership, and the journey behind Eels. I also had the chance to spend time with members of the 2026 EBV cohort, listening to their business pitches, asking questions, and providing feedback as they prepared to present their businesses.

This weekend was the next chapter, and I was asked to be the featured speaker for Alumni Weekend.

When I thought about what I wanted to say, I knew I didn’t want to stand in front of a room of entrepreneurs and make entrepreneurship sound prettier than it is.

It’s hard. Really hard.

There are great days. There are also stretches where very little seems to happen. There are decisions you make without knowing whether they are right. There are emails that never get answered, opportunities that disappear, expenses that continue whether business is coming in or not, and plenty of moments where you question what you are doing.

That was the conversation I wanted to have.

I also shared my own professional journey, not because I believe it offers some perfect blueprint, but because it certainly wasn’t a straight line.

My career started in the United States Navy. From there came inside sales, outside sales, project management, general management, senior corporate leadership, and eventually serving as Chief Operating Officer of a Connecticut law firm.

Then came Eels Professional Development.

Looking back, I see that journey much more as a lattice than a ladder. Each experience gave me something I would use later. The Navy gave me one foundation. Corporate leadership added another. Small business operations added another. Entrepreneurship has forced me to use all of it.

That experience also shapes the way I approach executive coaching today.

Leadership and entrepreneurship have something important in common: you are regularly asked to make decisions without having every answer.

During the keynote, I asked the EBV alumni to participate in two activities. The first looked backward: What advice would you give the next wave of veteran entrepreneurs The second looked forward: In ten years, my business or company will be...

I loved putting those two questions together.

One asks you to take everything you have learned, including the mistakes, and use it to help the person coming behind you. The other forces you to think about where you are still going.

There is something very veteran about both: serve the person next to you. Stay focused on the mission. Keep moving.

My professional journey started in the Navy. Today, I am an entrepreneur, founder, and executive coach building something of my own here in Connecticut.

I certainly do not have every answer about where the journey goes from here. I think that may have been the point of the entire presentation. You don’t need every answer to keep moving forward.

Thank you to UConn, the Connecticut Center for Entrepreneurship and Innovation, the EBV team, and everyone who participated in Alumni Weekend. I appreciated the opportunity to tell my story, but I appreciated even more being surrounded by so many veterans still writing theirs. Interested in learning more about how we support businesses and entrepreneurs? Learn more about our business and executive coaches in Connecticut and beyond here.