Business Owners Tell All: Celebrating 10 Veterans Turned Successful Entrepreneurs

Olivia Garrison

“Veterans are a symbol of what makes our nation great, and we must never forget all they have done to ensure our freedom.” – Rodney Frelinghuysen

There’s nothing quite like the courage of a veteran.

The courage to leave their loved ones behind to be part of something bigger than us all. The courage to put themselves in harm’s way to keep our country safe. The courage to dedicate their lives to uphold the values of “liberty and justice for all”.

For thousands of veterans across the country, this same courage follows them into their next chapter after transitioning to the civilian world: Entrepreneurship.

In honor of Veterans Day, we’re celebrating 10 more military men and women, past and present, who are making major strides in the business world after following their own entrepreneurial aspirations.

 


 

veteran business owners

Jake Messier

CEO/Partner, HEARD Strategy & Storytelling
Service Branch: United States Marine Corps

What made you want to start your own business after serving in the military?
While being a manager, supervisor or even a CEO of a company that you don’t own gives you some of the same feelings of obligation to your employees, there is no greater sense of responsibility than owning your own business and knowing that your employees and their families are depending on you to be a consistent and thoughtful leader. After serving nearly 10 years in the Marine Corps, the closest I’ve felt to ‘being in the trenches’ is working extremely closely with my employees on nearly impossible tasks and being successful for our clients.

How did your experiences in the military influence your skillset as a business owner?
Besides the obvious like leadership skills and problem-solving, I would have to say that self-direction, determination and discipline are the greatest influences in building a business owner. When you’re starting out, there is rarely is a roadmap and trusting your gut to make solid decisions for your business, your team and your clients only comes with having done it before. Since that is a critical skillset in the military, I believe it’s the most important.

What advice would you give to someone transitioning from the services into a business environment?
Trust the mentors in your life — your parents, your teachers, your former military leaders. Not only can they give you invaluable personal life lessons, but a lot of the time, they can likely give you trusted advice when building your business. I still keep in touch with several military colleagues, instructors and teachers even though I’ve been out of the service longer than I was in. A lot of the time, those people know you the best and can offer deep counsel that an acquaintance really can’t.

 


 

veteran entrepreneurs

Steve Sherwood

President, Anytime Fitness
Service Branch: United States Army

What made you want to start your own business after serving in the military?
I wanted to take ultimate responsibility over my future. I made a decision and took action to realize my dreams of financial freedom. Being a multiple business owner allows flexibility over my day, I develop my own schedule, and if I want to acquire more assets and achieve greater diversification I can. My troops are my employees who help me get the job done, my customers are my troops as well and need to be listened to and cared for daily. It’s all the same – taking care of people. It all started as being a Commander in the Army.

How did your experiences in the military influence your skill set as a business owner?
The military is 100% correlated to my successes as a business owner. The Army taught me the importance of daily disciplines, healthy habits, and taking care of people. Doing the same set of daily things, positive habits (making my bed, writing in my journal, reading, saying a prayer of gratitude, meditating for 10 minutes to clear my mind, daily exercise) snowball over time into a happy and productive lifestyle. I can better listen to my employees and care for my customers because the Army taught me to put people first. I want to see others excel and live a happy life, and being a business owner enables me the flexibility to bring that mantra to fruition. I can be a coach, a mentor, a confidant, and a leader as a business owner. No one day is the same! I like that. Happiness is a byproduct of taking right action. I become happy by seeing others succeed.

What advice would you give to someone transitioning from the services into a business environment?
Take the plunge. Determine what your dreams truly are and make a 1, 5, and 10 year plan and list objectives to live your dreams. How badly do you want it? It is much easier to go work for someone else, I did for a while, but not nearly as fulfilling.

 


 

 

veteran business ownersChristopher H. Gerhart

Substance Abuse Counselor, christopherhgerhart.com
Service Branch: United States Army

What made you want to start your own business after serving in the military?
Initially, I was not sure about starting my own business. I worked for a number of years for other people, but I got tired of seeing them make the lion’s share of the money from my hard work. I was also in a grant-funded position working for a social service agency and the funding for my position got cut. Finding myself out of work, through no fault of my own, I used a couple months of unemployment, picked up a certification in my field and set up shop. Just today, I visited my old supervisor and told him how good it was for me that I lost my job.

How did your experiences in the military influence your skill set as a business owner?
I was an Army cook, on active duty, assigned to a mechanized infantry unit that stayed deployed or on alert for most of my four years. I learned that perseverance, despite adversity, often wins the day. I also learned to get away from the TITWWHADI (this is the way we have always done it) mentality.

What advice would you give to someone transitioning from the services into a business environment?
Use your GI Bill benefits wisely. Make sure that your education will improve your employability by increasing your value. If it does not, then it can be a very expensive entertainment. Also, don’t rely solely on your GI Bill funds. Most colleges and universities have merit-based and need-based financial aid awards that are not influenced by the GI Bill benefits. Find and use mentors, people who have tried and done, and tried and failed, to do what you are setting out to do. You can always find someone who will tell you what you can’t do. Ignore them. Find the ones that will see you through.


Rank is not always worn on the collar or sleeve in the business world. I own and operate my business frequently wearing blue jeans and a polo shirt. There are times when I dress up in a suit and tie; but, more frequently than not, I look pretty much casual Friday, even on Wednesdays and Tuesdays. Get involved with something that affords the camaraderie of service. I am part of a rifle marksmanship program and go the range regularly. Some successful veterans do things with service organizations (Habitat for Humanity, churches, schools, those sort of places). They are great places to meet movers and shakers in, and retired from, the business community.

 


 

veteran entrepreneurPamela J. Booker

CEO/Creator, Koils By Nature
Service Branch: United States Army

What made you want to start your own business after serving in the military?
After the military I worked for the Federal government for about nine years. I started my business to have the ability to provide others with an amazing opportunity. I wanted to recreate the family-like environment that was created for me as a 19-year old serving in the US Army.

How did your experiences in the military influence your skill set as a business owner?
Serving in the United States Army, help me become the leader I am today. The Army Core Values:

  • Duty. Fulfill your obligations
  • Respect
  • Selfless Service
  • Honor
  • Integrity
  • Personal Courage

There’s no other family on EARTH like your military family, they know the pains, struggles, and triumphs. I am a proud US Army Veteran.

What advice would you give to someone transitioning from the services into a business environment?
We are special people…for those who’ve served, the transition will be smooth because we are trained to adjust and adapt. My advice would be to be understanding, have patience, and shine!


 

veteran business ownerTom Spooner

Founder/Co-Owner, Warriors Heart
Service Branch: United States Army

What made you want to start your own business after serving in the military?   
I am one of the three Warriors Heart founders, which is the first and only private residential treatment program in the United States solely dedicated to warriors (military, veterans and first responders) struggling with chemical dependencies, PTSD, mild TBI and other co-occurring symptoms in Bandera,Texas (just outside San Antonio). We lose more Warriors in the “War at Home” than the battles overseas. This fact is not okay with me or my current teammates.We will not just sit by idly watching them walk into the darkness, alone.
 
After retiring from the US Army, I approached my personal struggles with chemical dependencies, Post-Traumatic Stress Disorder (PTSD) and mild Traumatic Brain Injury (TBI) with the same commitment to excellence that I did in my military career. I began speaking candidly about the cost of my military experiences, and the reality of the difficulties coping with them. Determined to help my warrior community cope with suicide and addiction as a result of their experiences in War, I dedicated my professional efforts to healing as a Warriors Heart Founder and Co-Owner.

How did your experiences in the military influence your skill set as a business owner?
My military career leadership experiences have made me a better business owner in many ways. My strengths are teamwork, and as a team leader. My military experience included time in the 82nd Airborne, as a Green Beret in the US Army’s 7th Special Forces Group and, ultimately, in the US Army’s 1st Special Forces Operational Detachment Delta as an Operator.

I experienced a lot during my 40 months of combat. All of my combat time was at the team level, in the stack, kicking in doors and more. I have only one regret,and that is that I wish I could have done more, for my team, my unit, my country and my family.

What advice would you give to someone transitioning from the services into a business environment?
My advice for veterans transitioning into a business environment is do something you love and surround yourself with a solid team. It’s best to work with like-minded people who understand the warrior community.

 


 

veteran entrepreneursScott Sines

Founder, Real Estate 911 Solutions
Service Branch: United States Navy

What made you want to start your own business after serving in the military?
After 20 years of a very rigorous schedule, I knew that if I wanted to stay home and be with our boys (ages 13 & 10) and really be that Dad influence, I needed to have a plan. A good plan. Working for myself just made sense.

How did your experiences in the military influence your skill set as a business owner?
The one thing the military is good for is making leaders. The training they provide is perfect to get you in the mindset for what’s to come. As you rank up in the military you see how important those skills are. Being able to take those lessons, some harder to learn than others, and apply them to something that is your own, makes owning your own business all the more satisfying. Also, having the discipline necessary to run your own business is crucial and the military definitely offers you that.

What advice would you give to someone transitioning from the services into a business environment?
Understand that it isn’t going to happen on it’s own. Starting your own business or joining forces with a civilian one is going to require a conscious effort on your part to be successful. The military guides you with clothing & courses, you know when an opportunity to rank up comes and you prepare. The business world doesn’t work like that. Opportunity to advance is a daily thing and being present and aware of your responsibilities and having the initiative to fulfill them is what will help you get to where you want to go faster. It’s not as easy as taking a test, you have to be proactive now and not be afraid to stand out.

 


 

veteran entrepreneursJosh Vandenbrink

Owner, Iron Mountain Designs
Service Branch: United States Air Force

What made you want to start your own business after serving in the military?
I always knew I wanted to work in fabrication. I grew up fabricating from the time I was six. Coming out of the military with no tangible skills and not finding a place that was doing what I wanted to be doing, I decided to create it myself.

My background was more traditional construction. It was our family business. Starting in third grade pushing a broom, I sort of hopped from trade to trade until I landed in finish carpentry. As for the steel side, it was a medium that I was drawn to, but I’ve actually only been doing it for 10 years.

How did your experiences in the military influence your skill set as a business owner?
I spent 14 years at the highest level of special operations. I served over 20 combat tours. And when the men I worked with asked about starting my business, I tell them it’s the hardest thing I’ve ever done.

I can honestly say that over the last two and a half years, I think I might have failed if it weren’t the support of my wife, Steph. Something that I share with fellow veterans for encouragement is that our shared experience made us durable. The ability to tolerate hard times is something that I have leveraged to my success. Even recently, I worked 72 straight hours on a jobsite taking 20 minute cat naps in my van so that we could hit a deadline. It’s the military that nurtured that durability.

What advice would you give to someone transitioning from the services into a business environment?
Your military service is over, but your commitment to your community is not. Find a way to plug in and contribute. Be honest with yourself as to whether starting a business truly suits you. Being a business owner isn’t for everybody and there is nothing wrong with that. Reference question two, that 72 hour shift was six weeks ago and I haven’t worked less than 12 hours
since the 4th of July and I don’t see it letting up anytime soon. To men and woman built for it, that statement doesn’t scare them away and I’m happy to share every lesson and mistake if it helps them succeed. Like everything in life, the greatest rewards are hard earned.

 


 

veteran business ownersBrandon Ensley

Franchisee, Firehouse Subs
Service Branch: United States Air Force

What made you want to start your own business after serving in the military?
I’ve always been interested in owning my own business. After serving the Air Force, I decided to pursue my ‘American Dream’ of making that happen. Firehouse Subs was extremely appealing to me because the company mirrors many of my core values and commitment to the community. Through our customer donations, the non-profit of Firehouse Subs restaurant, Firehouse Subs Public Safety Foundation, has already granted more than $29.5 million worth of equipment, training and educations to first responders, public safety organizations and veterans since 2005. As these are the principals of the brand, this is what enticed me into opening (now three) Firehouse Subs restaurants.

How did your experiences in the military influence your skill set as a business owner?
My experience in the military influenced my skill set as a business owner in many ways. During my time in the Air Force I gained valuable leadership training and the ability to get along and work with all types of people. Structure and organization was also a huge influence in helping start my business. The beginning of the Air Force motto is ‘Aim High’ — keeping that motto in mind at all times reminds me to perform at my personal best and inspire my employees to do so as well.

What advice would you give to someone transitioning from the services into a business environment?
The opportunities provided through local banks and veteran programs allow former military personnel like myself to hit the ground running once returning to a civilian lifestyle. The advice I would give to someone transitioning from military service into a business environment is to take advantage of the resources available to you to support your pursuit in reaching your entrepreneurial dreams.

 


 

veteran entrepreneurNolan Martin

Creator, BudgetChaos.com
Service Branch: United States Army

What made you want to start your own business after serving in the military?
I’m still serving in the military, but I wanted to build a website where I could continue helping my Soldiers from previous units. In my military career, I have helped several Soldiers with their finances but lose touch with them when I PCS (permanent change of station). I created BudgetChaos.com to be able to continuously provide guidance and help them reach their financial goals. When I launched BudgetChaos.com, I realized my audience has grown from Soldiers to many people across all generations.

How did your experiences in the military influence your skillset as a business owner?
My military experience has helped me in my business because I’m able to apply the lessons I have learned in my military career. I realized that many people who seek help with their personal finances like the disciplined approach to my Financial Targeting Process. This process is designed to be easy to follow and help anyone in their path to reaching their financial goals.

What advice would you give to someone transitioning from the services into a business environment?
The advice I would give to service members who are transitioning is to find something you are passionate about and know the path you need to take BEFORE you get out of the military. If you are planning on going to school, you should already be accepted into the school and know when your classes start BEFORE you get out. If you are getting another job, you need to already have a start date. Too many times do I see Soldiers get out of the military without a plan.

 


 

veteran owned businessJack Somers

President/Co-Founder, Relobase Inc.
Service Branch: United States Marine Corps

What made you want to start your own business after serving in the military?
I was compelled to test myself (again) after the military, and business ownership seemed like the right test. I knew if I leveraged my training and experiences from the military, I could overcome the ‘start-up odds’ and succeed.

How did your experiences in the military influence your skill set as a business owner?
It gave me incredible perspective of pain and stress. When things are challenging or stressful with my business, I’ll often say to myself as long as I’m not getting shot at I have no reason to stress. Suddenly my stressful situation is not so stressful.

What advice would you give to someone transitioning from the services into a business environment?
Enroll in online computer programming courses or take part-time computer science courses. You must learn about technology and accept it as the new language of business. Businesses across all sectors and spaces are advancing and relying on more substantial technology stacks and systems. Do not rely on other people to make tech-based decisions for you — become an expert.

 


 

We want to give the sincerest thank you to these veterans for sharing stories about their transitions into entrepreneurship, and another huge thank you to the men and women who have served or are currently serving our country.

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