“Veteran entrepreneur” is more than just a buzzword—it represents a growing movement of service members taking control of their post-military lives and transforming their leadership, discipline, and resourcefulness into thriving businesses. One of the most passionate advocates for this movement is Reginald “Reggie” Thompson, a retired Sergeant Major and the Director of the Georgia Veterans Business Outreach Center (VBOC).
In this special episode of the VET S.O.S. Veteran Entrepreneur Spotlight, we reconnect with Reggie—who once served as the host’s instructor during a Boots to Business course—and dive deep into his mission to empower every aspiring veteran entrepreneur he meets.
A Smooth Transition Built on Observation
Reggie ThompsonUnlike many veterans who face unexpected challenges when leaving military service, Reggie’s transition was strategic. After serving for 32 years, he had time to observe others go through the process before him. He paid close attention to what worked and what didn’t, and he credits much of his smooth shift to civilian life to strong mentors and calculated planning.
His advice for today’s service members? Start early. Watch those ahead of you. Ask questions. Seek out mentorship. The earlier you begin preparing, the better your chances of becoming a successful entrepreneur.
The Entrepreneurial Spirit Was Always There
Long before he donned a uniform, Reggie had the heart of an entrepreneur. Growing up in Cleveland, Ohio, he and his brother ran their own hustle—delivering papers, mowing lawns, shoveling snow, and even selling candy at school after unplugging the vending machines.
“I didn’t even realize I was an entrepreneur back then,” he recalls. “But if you’re going to be a entrepreneur, you’ve got to know how to hustle.”
This early entrepreneurial mindset, combined with the leadership and resilience honed during his military career, would later shape his approach to veteran-focused business training and mentorship.
What Is the Veterans Business Outreach Center (VBOC)?
As a veteran entrepreneur, having access to the right resources is critical—and that’s where VBOC comes in. The Veterans Business Outreach Center is a program funded by the Small Business Administration (SBA) to help veterans, National Guard and Reserve members, and military spouses explore and pursue business ownership.
There are 31 VBOCs across the U.S. and abroad, covering even overseas military communities like Korea and Germany. Reggie describes the VBOC as the “eHarmony of the SBA”—not because it provides funding or writes business plans, but because it connects veteran entrepreneurs with the right support at the right time.
Whether it’s finding a government contracting partner, accessing local Chamber of Commerce programs, or getting legal help, the VBOC serves as a hub for veteran entrepreneur resources.
And the best part? It’s all free.
“You’ve already paid for it with your service,” Reggie reminds us. “So everything we offer is free 99.”
Boots to Business: The Launchpad for Veteran Entrepreneurs
One of the first programs Reggie recommends to every aspiring veteran entrepreneur is Boots to Business, a foundational course offered by the SBA and taught on military installations worldwide.
As a longtime instructor of the course, Reggie brings not just knowledge but passion and authenticity to the classroom. In fact, the host of the episode praises Reggie’s teaching style, recalling how his personal entrepreneurial experiences added depth and relevance to the training.
For veterans serious about launching a business, Boots to Business lays the groundwork. From there, Reggie encourages students to continue with courses like Revenue Readiness and take advantage of mentorship and counseling through their local VBOC.
Why Veteran Entrepreneurs Don’t Ask for Help
Despite the resources available, many veteran entrepreneurs spin their wheels unnecessarily. Reggie attributes this to either lack of awareness or pride.
“We talk about resources all the time, but even I catch myself doing too much or nothing at all,” the host admits.
Reggie agrees, noting that when people don’t know what to do, they either freeze or get overwhelmed by doing everything at once. That’s where the VBOC plays a critical role: saving veterans time, money, energy, and stress by pointing them in the right direction.
“If you come to me, I got you,” he says. “And even if you don’t, as long as you get help—that’s all that matters.”
No Competition, Just Collaboration
A unique aspect of the VBOC is its commitment to non-competition. Reggie emphasizes that their mission isn’t to compete with other programs—it’s to connect.
“There’s no ego here,” he says. “If you can do it on your own, great. But if you need help, we’re here.”
This collaborative mindset is crucial for the success of the veteran entrepreneur community. VBOCs work alongside organizations like SCORE, APEX Accelerators, SBA lenders, local SBDCs, and colleges to provide a robust support network for veterans at every stage of their business journey.
A Clear Roadmap for Veteran Entrepreneurs
So what does the path to success look like for today’s transitioning service member who wants to become a veteran entrepreneur?
Here’s Reggie’s simple roadmap:
Start with Boots to Business – This intro course will help you determine if entrepreneurship is right for you.
Take the Revenue Readiness Course – For veterans who want to sharpen their business skills and prepare for financial success.
Connect with Your Local VBOC – They’ll guide you through everything from registering a business to finding funding.
Leverage Free Resources – SCORE, SBA, and other partners offer workshops, mentorship, and tools at little to no cost.
Only Pay for What’s Necessary – Save your money for things like legal representation or intellectual property—use free resources for everything else.
Final Advice: Passion Drives Purpose
Reggie closes the conversation with a message that every veteran entrepreneur needs to hear:
“Do something you’re passionate about. If you enjoy what you do, it doesn’t feel like work—and the money will follow.”
Passion is what fuels long-term success. Whether you're launching a podcast, a product line, or a local service business, the key is to build something you love and surround yourself with people who support your mission.
Reggie also expresses gratitude to the podcast team for their professionalism, consistency, and dedication to supporting veterans. He recognizes their passion, and it reflects the same energy he brings to his teaching and outreach.
Final Thoughts: Don’t Go It Alone
If you’re a veteran entrepreneur or thinking about becoming one, know this—you’re not alone. There are free, trustworthy resources available to help you take the next step, no matter where you are in the process.
🔗 Find your local VBOC: https://www.sba.gov
🔗 Georgia VBOC: https://gavectr.org
🎓 Boots to Business Info: Available through your local TAP program or VBOC
And most importantly—don’t wait until you’re stuck. Reach out. Ask for help. Someone like Reggie Thompson might just be ready to guide you to your next big win.
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