Travis Winfield: Navy Senior Chief, Financial Literacy, and Building Wealth After Service
- Paul Pantani
- Dec 8
- 13 min read
How veterans and first responders create purpose, stability, and long-term success
In episode 225 of the Transition Drill Podcast, Travis Winfield’s story will resonate with military veterans, active-duty members, and first responders who’ve spent years serving others while trying to build stable futures for themselves and their families. His journey begins in Richmond, Virginia, and stretches across continents, commands, and decades of leadership in military law enforcement. What makes his experience meaningful isn’t just the uniform he wore; it’s the way he navigated transition, financial uncertainty, personal growth, and learning how to build life after service. Many men and women in uniform understand how trauma, financial stress, and identity shifts can affect their careers, relationships, and retirement planning. Travis learned those lessons firsthand and turned them into a mission to help others avoid the same challenges. His journey reminds us that purpose doesn’t disappear at retirement; it simply changes direction. If you’ve ever wondered how to prepare for a stronger transition or a healthier financial life, his story is worth exploring.
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Humble Beginnings, Early Responsibility, and a Path Not Planned
Travis Winfield’s story begins in Richmond, Virginia, where his family owned land, awarded to them by the King of England, long before the United States became a country. He grew up with history around him, but his daily life felt anything but historical or glamorous. His parents divorced when he was five, and he spent most of his childhood with his mother, learning early that life required responsibility and grit. For him, childhood never felt cushioned or easy. It felt practical, hands-on, and real.
Being raised primarily by a single mother meant money was tight and life required shared effort. Travis learned to work young. At fourteen, while many teenagers were still figuring out hobbies or after-school sports, he was working real jobs to help support everyday living. He continued that pace for years, holding seventeen different jobs between age fourteen and nineteen. Those jobs were not glamorous either. They were the kinds of jobs young people take because they need to survive and learn how to stand on their own. Travis learned firsthand that work ethic develops long before adulthood, and responsibility comes a lot sooner than anyone plans.
As a teenager, Travis describes himself as a rebel without a clue, making decisions the way many young people do when they don’t fully understand themselves or their direction yet. He didn’t have a clear plan for his future, and he didn’t come from a military background or a home that emphasized specific career paths. He simply worked, lived, grew up, and tried to figure it out along the way. His early experiences would later shape his empathy for young military veterans and first responders who transition into adulthood without clear pathways or financial structure.
During high school, everything changed when a new vocational pilot training program was introduced. Unlike traditional shop classes, this was a hands-on aviation training program designed to help students learn how to fly while still in school. Travis applied, got accepted as one of only twenty students, and discovered something he genuinely loved. He learned how to fly airplanes, and it gave him an ambition that he hadn’t felt before.
He dreamed of pursuing aviation. He earned acceptance to Averett University, one of the top civilian aviation programs in the country. The path seemed clear. He would become a pilot, build a career in aviation, and leave behind the uncertainty that shaped his early years. For a young man raised by a single mother, that dream represented more than a job. It represented stability, a meaningful profession, and a sense of belonging after so many years of working jobs without direction.
Reality, however, didn’t match his ambition. His parents made too much money for him to qualify for financial aid, but not enough to actually send him to college. It was a frustrating middle ground. Travis had a legitimate opportunity in front of him, but the one door he needed opened remained locked. There was no fallback plan, no family history of military service or scholarships to guide him, and no quality knowledge of the military academies before it was too late to start the acceptance process.
With limited options, Travis felt the pressure to build a path quickly. He was working, but not at anything that provided a future. To this point, he had not considered the military as an option. His decision to enlist was a necessity. He needed structure, income, and a chance to build a future.
In his senior year, a recruiter came to his high school, and Travis listened. His motivation wasn’t about patriotism or dreams of serving. He simply needed something concrete, predictable, and stable. He became the first person in his family to ever join the military, which became the beginning of a twenty-four-year career and eventually, a personal mission to help military veterans navigate life, retirement planning, trauma, and financial uncertainty.
Military Identity, Law Enforcement Calling, and Becoming a Leader
When Travis joined the Navy, he thought he knew what he was signing up for. He entered on a contract to become an aircrew Search and Rescue swimmer, the kind of sailor who jumps out of aircraft to pull people out of the water. It felt like the natural extension of his love of flying and his desire to do something physical and meaningful. That plan ended before it ever really started.
Right before he graduated from boot camp, the Navy reviewed his medical file and focused on a sinusitis diagnosis from years earlier. It was enough to disqualify him from the aircrew SAR pipeline. There was no appeal and no second chance. One day he was on track to jump out of helicopters. The next day he was told, “You can’t do that anymore, go find another job.”
The decision hit hard. He had already given up on aviation school and a civilian path he understood. Now the Navy was taking away the only version of his military future he’d imagined. The frustration turned into a bad attitude. He’ll tell you he carried a strong “FTN” mindset for a while, angry that what he’d been promised no longer matched reality.
Instead of sitting him down with a counselor and a thoughtful plan, the Navy handed him a sheet of paper with a list of available ratings. Each had a short paragraph description. That was it. He had thirty minutes to choose the job that would define his next several years. He picked Operations Specialist. The description mentioned work with aircraft control, and that kept a small link to the world he’d originally wanted. He went to “A” school for the rating, and graduated as the honor graduate, number one in his class. On paper, it looked like the perfect turnaround story. In reality, he hated the work.
As an Operations Specialist, he stared at radar screens for hours at a time. The job was important, but it didn’t fit him. He liked people, movement, and real interaction. Sitting in a dark space, watching a screen, felt like the exact opposite of the life he wanted. He did the job for about three and a half years, performing well but never feeling fulfilled. That changed the day he met the Chief Master-at-Arms on his ship.
The Chief was, in Travis’s words, the sheriff of the ship. He was responsible for law enforcement, discipline, and the kind of presence that sets the tone for everyone on board. Travis watched how he handled situations, how he carried himself, and how people responded to him. The work looked human, direct, and grounded in real responsibility. It wasn’t about staring at symbols on a radar; it was about dealing with real people and real problems.
The Chief became a mentor. Through him, Travis saw a part of the Navy that aligned with his natural strengths. He learned more about the Master-at-Arms (MA) rating and decided to submit a package to convert. Back then, converting was not automatic. It required a full board process and a detailed package that proved you were worth the investment. Travis went through that process and was approved in the mid–1990s. Once he became a MA, everything shifted.
The Navy sent him to law enforcement training at Lackland Air Force Base, at the time the Navy used the Air Force for initial training. That gave him the foundation of military police work. From there, he attended advanced schools run by the Army. He trained as a military police investigator at Fort McClellan and later attended protective service school at Fort Leonard Wood, and learning how to function as a dignitary bodyguard. Those schools gave him skills, but the fleet gave him wisdom.
Working as a MA, Travis saw the side of military service most civilians never think about. He dealt with sailors under stress, families under pressure, alcohol problems, money problems, and the kind of trauma and mental health struggles that show up behind closed doors. He understood quickly that when a service member made a bad decision, there was usually a story behind it. That perspective would later shape his desire to help military veterans and first responders with financial literacy and life after service.
Professionally, he began to grow into leadership. He understood that good law enforcement inside the military is not about throwing weight around; it is about protecting people, enforcing standards fairly, and leaving organizations better than you found them. One of the most important chapters in this stage of his life came when he was stationed overseas. He spent time in Greece, where he met the woman who would become his wife, she is from Sweden. That experience added a different kind of responsibility to his life. He wasn’t just a sailor or a cop anymore; he was a husband, and later a father, trying to balance mission, career, and family in foreign countries.
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Command-Level Leadership, Global Service, and Transition Awareness
As Travis continued serving as a MA, his responsibilities grew with experience. He worked security assignments in multiple locations, including Sicily and Norfolk. Command relied on him. His reputation and experience eventually led to a defining opportunity: he became the Command Senior Chief aboard the USS Freedom, a Littoral Combat Ship. The ship had a small crew, which created a leadership environment that felt very personal. Travis was no longer simply enforcing standards or managing investigations; he was shaping the health, culture, morale, and operational rhythm of the entire command. Every sailor mattered, and there was no place to hide from responsibility.
A senior enlisted leader is more than a rank or title; they become an advisor, counselor, advocate, and guardrail for those around them. Travis took that responsibility seriously. He helped sailors who struggled with financial instability, alcohol problems, relationship stress, and the emotional weight that often follows long separations from home. He understood that trauma, mental health, financial mistakes, and poor coping mechanisms are not signs of failure; they’re part of the human side of military service.
Living and working overseas had already taught Travis about sacrifice, culture, and adaptability. Now, as a Command Senior Chief, those lessons came into sharper focus. The Navy wasn’t only his job; it was his community, his family, and the structure that shaped his daily life. Success was measured not only by mission performance but by the wellbeing of the crew. The ship had to be ready, but the sailors needed stability, mentorship, and space to grow professionally and personally.
Leadership also made Travis think more seriously about transition. He began to understand that every military member eventually reaches a point when the uniform can no longer be the center of life. Whether someone serves four years or thirty years, transition is inevitable. Travis had served long enough to see how challenging that shift could be for people who didn’t prepare for life after service. Financial problems, marriage strain, identity confusion, and the loss of purpose could affect even the strongest professionals once they separated from the structure the military provides.
Travis knew his own career as a MA and Command Senior Chief was nearing its natural conclusion. He could have remained on active duty and advanced into higher leadership billets, but advancement no longer felt required. He’d reached a point in life where his identity wasn’t tied to continuing promotion. He didn’t need to chase another stripe to feel fulfilled. He cared about impact more than recognition.
After twenty-four years of service, Travis made the decision to retire from the Navy. It wasn’t necessarily by choice, it was a natural transition point. He’d served long enough to know that, even making E9, another tour would likely mean simply continuing the same work. He wanted to build a life after service that allowed him to be present with his family, develop civilian skills, and support new missions unrelated to his military rank. Retirement planning wasn’t about leaving the Navy behind; it was about building a sustainable second chapter.
At home, he understood something many veterans eventually learn. Military life gives structure, purpose, camaraderie, and a predictable identity. Civilian life requires rebuilding that structure from scratch. The Navy teaches service members how to protect the nation, but it doesn’t teach financial literacy, emotional reintegration, or the practical steps needed to thrive once the uniform comes off. That gap inspired Travis to start thinking about his responsibility to help others prepare better than he had.
Life After Service, Financial Literacy, and Military Operated Real Estate
Retiring from the Navy after twenty-four years gave Travis a sense of pride, but it also gave him a sudden amount of space to think about what came next. For most military veterans, the hardest part isn’t turning in equipment or leaving a command; it’s waking up and realizing the uniform no longer defines the rhythm of daily life. The routine, the chain of command, and the professional identity that shaped every decision have disappeared. Travis felt the same shift. He wasn’t anxious or unprepared, but he understood that life after service would require a different mindset and a renewed sense of purpose.
Travis gained strong leadership skills and tremendous experience in law enforcement, investigations, security, and command-level operations. He also had an instinct for entrepreneurship. He got his real estate license and was selling real estate before he retired, then after retirement, he built a real estate company with the same work ethic he developed as a teenager. He taught himself the business, learned how to manage transactions, and found enough success to eventually turn the company over to his son. That moment wasn’t just professional accomplishment; it represented legacy. Travis gave his son the opportunity to build his own career and financial future.
A major influence on Travis’s post-service mission came from one of his closest mentors, retired Green Beret Larry Broughton, who later became a highly successful entrepreneur. Larry taught Travis the principle of living life in thirds. The idea is simple but powerful: spend one-third of your time learning from people who have already achieved what you want, spend one-third of your time investing in family and peers who support you, and spend the final third mentoring those coming behind you. Travis embraced that philosophy and now applies it to his financial education work, his mentorship programs, and his real estate organization, Military Operated Real Estate (MORE). He believes veterans and first responders grow stronger when they learn from mentors, stay grounded with family, and help the next generation build security and confidence early in their transition.
Travis saw that military life trains people to protect, to serve, and to accomplish difficult missions, but it rarely teaches them how to build financial confidence or lasting security. Travis started sharing what he learned through online classes. He created Military Money MORE, an instructional course he taught every month. Students from across the veteran community attended, and word began to spread. One of those students was Russ Smith, who had served as the fifteenth Master Chief Petty Officer of the Navy. He joined one of Travis’s classes during COVID and listened to an hour-long session focused on financial fundamentals, savings habits, and the realities of building wealth after service. When the session ended, Russ admitted something that shocked him. He said he had spent thirty-seven years in uniform, mastered combat, and learned every requirement of leadership, but he never learned how to save or build true financial stability. Travis remembers Russ telling him that financial education should be taught during boot camp.
That moment reinforced what Travis already believed. Too many military members leave service with leadership, discipline, and experience, but without a realistic plan for their civilian future. Transition is more than a change of job title. For many veterans and first responders, it is a shift in identity, responsibility, private sector expectations, and financial pressure. The absence of financial literacy can create stress for families, reduce retirement options, and delay long-term security.
Those conversations helped Travis realize people needed something permanent. His past mentors encouraged him to write a book, and even though he didn’t love writing, he finally committed to the project. He dictated most of the chapters and then worked with editing support so his thoughts would come through clearly. The final product captured the message, mission, and lessons he had been teaching through Military Money MORE. Russ Smith even allowed Travis to include an entire chapter about his own financial struggles near the end of the book, reinforcing that even the Navy’s most senior enlisted leaders are not immune to financial blind spots.
The purpose behind his writing was not entertainment. It was education and empowerment. Travis kept seeing veterans with long careers step into civilian life without savings, without assets, and without a financial plan. Some retired after twenty years of military service with valuable leadership skills, but without a real roadmap for life in the private sector. A young infantryman can spend an entire career focused on tactical operations, weapons, and mission execution without ever learning how to build wealth, save responsibly, or invest in long-term security. For Travis, that gap represents a looming crisis. As more members of the post-9/11 generation retire, financial instability could grow into homelessness, stress, and long-term emergency support needs if financial literacy does not improve.
The book and the online classes were only part of the solution. Travis also turned to real estate. He recognized that home ownership, financial literacy, and long-term stability are closely tied together. He founded Military Operated Real Estate (MORE), a real estate training and mentorship institute exclusively for military-affiliated professionals. The requirement to participate is simple. You have to be a veteran, active-duty member, or a military dependent who has genuinely lived the lifestyle, including moves, deployments, relocations, and the rhythms that military families experience. Travis wanted people involved who understood what military families need, how they communicate, and how their finances operate.
MORE is not just a real estate brokerage or team. It is a SkillBridge-approved national real estate company. That means a transitioning service member can spend the last six months of their military service working full time for a MORE-approved team or brokerage, receiving full military pay and benefits, while going through structured training and hands-on experience in real estate. Travis believes this model prepares transitioning members for civilian careers before they separate, which can reduce financial stress and help people establish meaningful civilian skills while still receiving military income.
MORE is also the only real estate company in the country approved by the Department of Veterans Affairs. The foundation behind MORE is not only market success. It is the responsibility to train real estate agents who specialize in serving military families, veterans, and first responders with integrity, deeper education, and better protection. Travis wants MORE graduates to understand the complexity of VA loans, relocation pressures, retirement timelines, financial vulnerabilities, and the emotional weight that transition can carry. His mission is to create real estate professionals who can guide veterans and military families into stable home ownership with more confidence and fewer mistakes.
Travis views MORE, his financial education work, and his book as connected pieces of the same mission. Military veterans and first responders deserve more than a thank you for their service. They deserve education that protects their futures, strengthens their families, and gives them tools for life as civilians. Travis believes that financial literacy is not a luxury. It is a responsibility that can protect military families decades after retirement.
Closing Thoughts
Travis Winfield’s journey shows that military veterans and first responders can build meaningful futures long after their service ends. Transition isn’t only about finding a new job; it’s about developing financial confidence, emotional clarity, and a strong support system. Travis reminds us that retirement planning, mentorship, and personal responsibility can protect families and reduce stress before life after service begins. His mission is simple: help others avoid the financial struggles, trauma, and uncertainty he witnessed in uniform. When military members and first responders prepare early, they create smoother transitions, healthier relationships, and stronger communities built on experience and purpose.
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