The Veteran Entrepreneur Journey: From Military Leadership to Purpose-Driven Business
The veteran entrepreneur journey is filled with twists, turns, and defining moments that test both personal resilience and professional adaptability. For many transitioning service members, the path to entrepreneurship offers a way to continue serving—this time by creating value in the civilian world. One such inspiring story belongs to Marine Corps veteran Jason West, whose entrepreneurial pursuit blends leadership, mission alignment, and purpose.
In a recent episode of the VET S.O.S. Veteran Entrepreneur Spotlight, host Maurice Murphy sits down with Jason to unpack his journey from Lieutenant Colonel to founder of Officers Eat Last, a consulting firm that champions servant leadership and business growth with integrity. What emerges is a candid and insightful discussion packed with lessons for any veteran navigating the complex road of post-military business ownership.
Starting the Veteran Entrepreneur Journey
Jason WestJason West’s veteran entrepreneur journey didn’t begin with a clear roadmap. Like many who’ve served, his career was multifaceted—spanning roles as an enlisted reservist, a bank employee, and finally, a commissioned Marine Corps officer. Initially planning only one tour of duty, Jason stayed on active duty for 10 years and later served in the reserves. But in 2006, he made the leap to the private sector, where new challenges awaited.
Reflecting on his transition, Jason identified three key lessons:
Be a student of the private sector. Veterans must immerse themselves in learning how business works—studying trends, mastering industry tools, and adapting their skills.
Be patient. Unlike the military’s structured timelines, business success takes time and often unfolds unpredictably.
Be nice. Military culture sometimes rewards intensity and authority, but in business, empathy, and collaboration matter more.
“Being nice is something I had to remind myself of. In the Marines, intensity can get things done. But in the civilian world, that doesn’t translate,” Jason shared.
These early realizations laid the groundwork for Jason’s evolving approach to leadership and entrepreneurship.
The Spark that Ignited a Business
Every veteran entrepreneur journey has a spark—and for Jason, it was a conversation with a contact in the defense contracting world. The individual suggested that if Jason could establish a service-disabled veteran-owned freight brokerage company, he would route at least $1 million worth of Department of Defense freight through the business each year.
That promise set things in motion.
“There was the spark. That was it. I was off to the races.”
Despite not knowing all the intricacies of the freight industry, Jason embraced the challenge. He built the company from the ground up and eventually secured freight contracts, though not to the extent initially promised. Still, the business generated enough cash flow to build something sustainable—and to fund his next venture.
This stage of his veteran entrepreneur journey exemplifies the essence of adaptability, hustle, and resourcefulness that so many veterans bring to the table.
Leading with Purpose
One of the defining features of Jason’s entrepreneurial mindset is a deep commitment to purpose. For him, success isn’t just about revenue—it’s about aligning all key stakeholders around a common mission.
“You can’t just tell your team that you’re trying to make as much money as possible. That doesn’t inspire people. Purpose does.”
In his businesses, Jason prioritized aligning clients, employees, and vendors with a larger cause. Whether supporting DOD logistics or scaling leadership potential within companies, Jason’s ventures have always centered on service and impact.
This approach ultimately led him to create Officers Eat Last, a firm rooted in the principle of servant leadership. The name, drawn from military culture, represents the ethos that leaders eat after their troops—a powerful metaphor for putting others first.
Lessons from the Hard Road
Jason is the first to admit that the veteran entrepreneur journey is not easy. One of his most frustrating experiences was the unmet promise of $1 million in contracts. Instead of wallowing in disappointment, he leaned on his military instincts to adapt and overcome.
“You have to shift fire. Sit in your sadness for a bit—but then keep moving. Get new clients. Push forward.”
Like many entrepreneurs, Jason learned that success in business is rarely linear. It’s full of setbacks, miscommunications, and broken deals. But it’s also full of small wins, long-term growth, and the satisfaction of building something meaningful.
He emphasizes that the emotional weight of entrepreneurship is real. Veterans are often well-prepared to handle the stress and ambiguity thanks to their training—but it’s still a difficult path.
“There’s no chain of command in business that forces someone to buy your product or work for you. Everything is voluntary, and that creates constant uncertainty.”
Finding Support Along the Way
A major success factor in any veteran entrepreneur journey is support—and Jason found his early network through the Knoxville Chamber of Commerce. While not a traditional veteran organization, it connected him with other veteran business owners and professionals eager to help.
“Veterans want to help veterans. Build relationships with those who are further down the road. They’ll teach you what you don’t yet know.”
Jason didn’t limit himself to any one program. He tapped into community networks, sought out peers, and built friendships with mentors who helped him grow as a business owner. For any aspiring veteran entrepreneur, he recommends finding local business organizations, veteran meetups, and digital communities to build that same support structure.
Building Officers Eat Last
After successfully exiting his freight brokerage business, Jason authored Leadership Development: A Blueprint for Building Your Leadership Foundation. This book, combined with his experience in business growth, led him to launch Officers Eat Last.
The firm helps business owners align their teams, scale effectively, and prepare for significant milestones such as acquisition or investment rounds. At its core, the company promotes a style of leadership focused on service, humility, and alignment.
“It’s not about being in charge. It’s about serving the mission—and those you lead.”
Jason’s firm stands out in the crowded consulting landscape because of its authenticity. Every lesson, tool, and framework offered is backed by experience—earned through years of service and entrepreneurial grit.
Advice for Fellow Veterans
Jason’s final advice for those considering entrepreneurship after military service is grounded in realism but steeped in encouragement:
Be ready to learn fast. Study the language and culture of the private sector.
Embrace uncertainty. The business world is unpredictable, but veterans are trained for ambiguity.
Find your people. Build a support network early.
Stay aligned with purpose. Purpose is your fuel during hard times.
Be patient with progress. Don’t expect quick wins; expect persistence.
Above all, Jason encourages fellow veterans to reflect on what they truly want and then build businesses that reflect those values.
Conclusion: A Purpose-Driven Path Forward
Jason West’s story is more than just a personal journey—it’s a roadmap for others navigating their own veteran entrepreneur journey. From handling broken promises to building purpose-led ventures, Jason’s path illustrates how veterans can thrive in the business world by leading with service, integrity, and mission focus.
If you're a veteran considering entrepreneurship, take heart in Jason’s journey. You already have the mindset and skills—now, it’s about applying them with strategy, purpose, and a willingness to grow.
To connect with Jason or learn more about his work, visit officerseatlast.com, explore his YouTube channel, or connect with him on LinkedIn.
