From Veteran Struggles to Success: Transforming Challenges Into Opportunity
“My journey has been anything but ordinary,” shares United States Air Force Veteran and entrepreneur Robert Woodin.
And in the landscape of American small business, success stories often emerge from the most unexpected places. Bob’s path proves resilience, determination, and support can turn life’s obstacles into remarkable achievements.
In a constantly moving, unstable household, Bob’s early life was defined by uncertainty. As a young teenager, he had already made the difficult decision to become self-sufficient.
“At 15, I made a decision, that no 15-year-old should have to make, that would change the course of my life,” he reflects. “I moved out of my chaotic trailer park life and into another older friend’s from the same trailer park.”
Bob says it wasn’t easy, and he began working three part-time jobs while completing high school. Yet this early experience of survival and hustle would become the bedrock of his future triumphs.
“I never had the opportunity to join sports or enjoy the typical high school experiences,” he says, “but the friends I made in that little trailer park during this time are still part of my life today.”
Bob’s entry into the Indiana Air National Guard in 1986 marked a pivotal turning point. For the first time, he was introduced to structure, discipline, and the possibility of a more stable future. Over the next three decades, he would rise through the ranks of the Air Force, ultimately becoming a Chief Master Sergeant — a position held by only the top 1% of enlisted personnel.
“Although I rarely use that title now,” he says, “it represents how far I had come — from a person with nothing to someone recognized as a leader in the Air Force.”
Bob emphasizes how during this time he also married the love of his life, Lisa.
A Foundation Built on Overcoming
Though he had significant military accomplishments, Bob faced substantial personal challenges. Multiple deployments and the intense stress of military life led to severe post-traumatic stress disorder (PTSD). After retirement, he found himself struggling to find direction and feeling lost behind what he describes as a mask of perceived strength.
“Despite my success in the Air Force, I found myself lost and unable to move forward after retiring. I had spent so many years hiding behind the mask of ‘I’m fine’ that I couldn’t see a way out.”
The Power of Support
Moments of change for Bob came through two important support systems: the Veteran Administration’s Vocational Rehabilitation and Education (VR&E) program and the Florida SBDC at the University of West Florida. These organizations didn’t just offer resources; Bob explains how they provided a road to reinvention.
Bob became the first veteran nationwide to complete the VR&E “Self-Employment” track. He describes how the Florida SBDC was key in carving out this route as well as transforming his knowledge and dreams into a fully operational company: Veteran Architectural Design and Drone Services.
“It opened new doors for me,” he says. “I was given the opportunity to learn new skills and pursue a career that aligned with my passions. I was trained to become an Architectural Designer and FAA 107 Drone Pilot. This journey didn’t end with education alone. The Florida Small Business Development Center provided invaluable mentorship, especially from Kevin Oster, who played a critical role in helping me turn my education and passion into a viable business. With Kevin’s support, I developed a business plan and launched my veteran-owned business.”
Building Business With Community
“As I move forward into 2025 with Lisa, that same love of my life I married 36 years ago, I’m focused on channeling the success I achieved in the military into my entrepreneurial ventures,” Bob states. “Starting a business today presents its own set of challenges, particularly for veterans who are coping with PTSD, anxiety, and depression. On top of that, navigating the fast-paced world of social media and digital marketing can feel overwhelming. While social media is a crucial tool for growing a business, breaking through the noise and reaching an audience is tough, especially when you’re just starting out.
“Here’s what I’ve learned: success doesn’t come without help. The programs like VR&E and the mentors at places like the SBDC have been instrumental in getting me to where I am today. But the journey doesn’t end with having the right tools and skills — it’s about support.”
To thank and support veteran entrepreneurs like Bob: engage with their content, share their stories, and recognize the unique value they bring to our business landscape. For example, learn more about VAD-DS via their YouTube channel and reach out to connect with the business!
