Veteran Entrepreneurship: Dr. Anthony Randall’s Mission-Driven Journey from Combat to Coaching
Veteran entrepreneurship is a growing force in today’s economy—driven by purpose, forged in discipline, and powered by the unique leadership experiences of those who’ve served. Among these trailblazers is Dr. Anthony Randall, a retired U.S. Army Lieutenant Colonel, West Point graduate, and founder of Vanguard XXI, a full-spectrum leadership development and executive coaching firm based in Columbus, Georgia.
In a recent episode of the VET S.O.S. Veteran Entrepreneur Spotlight, Dr. Randall sat down with host Shawn Welsh to share his deeply personal and professional story. From launching a paper route at 11 to leading troops in combat, and finally founding a thriving business, his path exemplifies the resilience, vision, and service mindset at the heart of veteran entrepreneurship.
Early Lessons in Leadership: A Paper Route and a Fire Extinguisher
Dr. Anthony RandallDr. Randall’s first brush with entrepreneurship came at a young age. At just 11 years old, he became the youngest paperboy in Denver, delivering the Rocky Mountain News. One morning, while completing his route, he was assaulted by a group of teenagers with a fire extinguisher. The attack left him tearful, shaken, and covered in foam. But when he returned home, his parents asked a simple question: “Did you finish your route?”
That moment became a defining lesson in perseverance, one that shaped his approach to leadership and entrepreneurship. “Adversity will come at you,” he says. “The question is: how will you respond?” This mindset would carry Dr. Randall through a distinguished military career and into the uncertain world of veteran entrepreneurship.
The Challenge of Military Transition
For Dr. Randall, the most difficult 12 months of his career weren’t in uniform—they came after he hung it up. His transition out of the Army, which took place from April 2020 to April 2021 during the COVID-19 pandemic, was filled with uncertainty, isolation, and pressure. Like many veterans, he faced the challenge of redefining his identity and finding purpose outside the military structure.
“Transition is not like deployment,” he says. “You don’t do it as a unit. It becomes a Choose-Your-Own-Adventure story.”
This personal challenge inspired Dr. Randall to launch Vanguard XXI, a company that merges character-based leadership development with certified executive coaching—a space where veterans, professionals, and organizations alike can grow together.
Veteran Entrepreneurship Begins with Self-Awareness
One of the pillars of Vanguard XXI’s success is its emphasis on knowing yourself first. Dr. Randall believes that veteran entrepreneurship requires more than just business acumen—it demands self-awareness, emotional intelligence, and moral clarity.
Vanguard XXI’s programs are built around three key questions:
Who are you?
Identity is central. Veterans often carry deep experiences that shape their values and decision-making. Vanguard helps them reconnect with those principles and understand their psychological and moral frameworks.How do you think?
Many transitioning veterans are told what to think in civilian spaces but aren’t taught how to think critically. Dr. Randall emphasizes logic, reasoning, and ethical decision-making as core leadership skills.How do you lead?
Leadership is more than a job title. Through emotional intelligence (EQ) assessments and practical coaching, Vanguard teaches veterans how to lead teams with empathy, resilience, and adaptability.
This structured approach helps veterans move from self-reflection to execution—essential for long-term success in entrepreneurship.
Bridging the Gap with the Entrepreneurial Operating System (EOS)
While many veterans excel in leadership and operations, they often face a steep learning curve when launching or growing a business. That’s where the Entrepreneurial Operating System (EOS) comes in—a method featured in Gino Wickman’s popular book Traction.
Vanguard XXI adopted EOS early on, using it to guide team meetings, structure quarterly goals, and scale operations. According to Dr. Randall, EOS is ideal for businesses with up to 250 employees and up to $200 million in revenue. It’s become a foundational system for managing growth in the world of veteran entrepreneurship.
“If you’re a veteran without an MBA, EOS gives you the structure to operate like a seasoned executive,” he explains. “It turns military leadership language into business success language.”
Accountability through Advisory Boards
Another game-changer for Dr. Randall was forming a board of advisors. Comprised of leaders he has known and trusted for over 20 years, this board offers guidance on financials, strategy, and long-term planning. They review Vanguard XXI’s balance sheets and P&L statements, helping keep the mission focused and the vision sharp.
For those venturing into veteran entrepreneurship, Dr. Randall strongly recommends surrounding yourself with a circle of trusted advisors. “It’s not about doing it all yourself. It’s about being coachable and willing to listen.”
Vanguard XXI: Where Coaching and Leadership Meet
Vanguard XXI isn’t just a business—it’s a movement. The company blends leadership development and professional coaching into a cohesive experience. Dr. Randall, a Professional Certified Coach (PCC) with the International Coaching Federation (ICF), explains that coaching is not the same as mentoring, counseling, or consulting. It’s a unique skillset—and one that can be taught and refined.
Vanguard XXI offers a full suite of ICF-accredited coaching courses, including:
Level 1 (61-80 hours) – Helps participants earn their ACC
Level 2 (65 hours) – Prepares students for their PCC
Level 3 (in development) – Aims at the elite MCC level
Corporate CCE courses (24 hours) – Ideal for businesses and organizations
Ethical Leadership and Women in Leadership courses – Specialized offerings
These courses are deeply experiential, attracting high-caliber individuals including NFL coaches, cyber warfare officers, and seasoned business consultants.
“We don’t kill you with PowerPoint,” Dr. Randall jokes. “We build communities. That’s where the magic happens.”
Veteran Entrepreneurship as a Force Multiplier
What sets veteran entrepreneurship apart is the ability to apply battlefield lessons to the boardroom. Veterans know how to build teams, overcome adversity, and adapt to changing conditions. Vanguard XXI is a living example of that mindset in action.
Dr. Randall and his team of 14 (including several West Point classmates and Ranger School peers) have created a business ecosystem built on trust, transformation, and high-performance coaching. They’re not just training coaches—they’re building future leaders equipped to elevate organizations from the inside out.
A Call to Action for Veteran Entrepreneurs
Dr. Randall’s message to aspiring veteran entrepreneurs is clear: You have what it takes. But you need to invest in personal development, embrace accountability, and find systems that help translate your military strengths into business impact.
Whether you're looking to start a coaching business, become a more effective leader, or simply find your post-service purpose, veteran entrepreneurship offers a pathway to build something meaningful—not just for yourself, but for your community.
“Finish the route,” Dr. Randall says. “No matter what comes at you.”
Get Involved with Vanguard XXI
Ready to take your next step in veteran entrepreneurship?
👉 Visit www.vanguardxxi.com
👉 Explore coaching courses, keynote speaking, and leadership development
👉 Connect on LinkedIn and Instagram
👉 Listen to the full episode on the VET S.O.S. Veteran Entrepreneur Spotlight
🎙️ This episode is sponsored by Spearpoint Solutions. Use code “VETSOS” to support the mission.
💬 Follow VET S.O.S. on YouTube, Spotify, and all major platforms to stay updated on veteran success stories.
