Why Veterans looking for their next career should consider finance

November 3, 2021 Tarah Wolking
From serving the country to serving clients, see what three Schwab Financial Consultants had to say about their career transitions from the military.

Many Veterans find themselves searching for their next career move after leaving the military. Whether they served a few years or retired after decades, the decision on what to do next is big.  

And it can be a challenge to find something you’re passionate about that also aligns with the skills you’ve developed. 

As the demand for financial advice continues to grow, so do the career opportunities, making this industry a noticeable option for job seekers. 

We spoke with three Schwab Financial Consultants, each with their own unique military backgrounds, to learn what brought them to this profession and how past experiences impact the way they serve their clients.      

Veterans turned financial planners

It may not seem like a natural progression to go from flying helicopters to financial planning. But that’s exactly what Mike Leupold, Schwab Financial Consultant and retired United States Navy Pilot did. 

Mike said as his retirement was approaching, he began doing some soul searching for what to do next and realized the answer was finance.  

“I’ve had a passion for investing my whole life. As a teenager I was self-taught and enjoyed doing my own research and learning how to invest,” said Mike. “When I was retiring from the military, I really didn’t want to go into defense contracting or be a government service worker. I wanted a change of pace.” 

Barry O’Shea, VP Financial Consultant at Schwab and past United States Army Captain, took a hybrid approach to the profession. 

Growing up in a family with deep military roots, Barry always knew joining the armed services was part of his plan. 

“I received a four-year ROTC scholarship to the University of Colorado Boulder,” said Barry. “I majored in Finance and Accounting and gained professional experience by working three bank internships during that time.”

Charlie Stover, VP Financial Consultant at Schwab and former infantry and Special Operations Officer for the United States Army paved a slightly different path. After his time serving, Charlie worked in manufacturing management for a few years before transitioning to financial services. 

Charlie shared there were many aspects of the profession that appealed to him. 

“Being able to limit travel and spend more time at home with family is an invaluable perk to the job,” said Charlie. “I also love the technical acumen, planning, and helping people. So being in a career that brings all of that together is what drew me in.” 

Making the career transition

Starting over in an industry like financial services which requires certifications, licenses and learning rules and regulations can be a lot to take on. 

“I had to start at the ground level, get all my credentials and work my way up,” said Mike. “But I knew in the long run it was the finish line I wanted to get to—to serve all those folks.” 

And once you have your credentials, you’ll need clients. 

“Building a book of business from zero was a huge challenge,” shared Charlie. However, as you begin working with clients and making connections, it can become a very rewarding profession. 

Mike says he enjoys that it’s not a cookie cutter career with redundant tasks; it’s about problem solving and helping clients with their individual goals. 

“If I get off the phone and my client is in a better position than before I called them, that’s a success,” said Mike. “And each time you connect, you’ll start building up trust and will be able to relieve some of the anxiety that can come with financial planning by answering client questions like: Will I have enough for the future?” 

Special qualities from a military background 

There are aspects of the job a person needs to be successful that aren’t easily taught.   

For example, Mike says being in the military can help you develop entrepreneurial skills.   

“We certainly focus on teamwork, but we’re also able and expected to work independently, to self-motivate. The military will often give you a task that you have to go off on your own to do, or in a small group, and motivate people and then report back. We’re goals oriented and we want to get the job done and be trusted to do so.” 

According to Charlie, servant leadership and the ability to plan are keys to success. 

“If you want to successfully lead, you have to care for and take care of your people and most often that comes in the form of understanding and addressing their needs and acquiring the resources they need to make good decisions. And you have to be a planner in both professions. If you don’t plan, confusion and chaos ensue.” 

Working with Veterans and active-duty clients 

Mike, Barry and Charlie work with a variety of clients, but they all agree it can be easier to connect with Veterans and their families due to their shared backgrounds. 

Barry says it’s an honor to talk to veterans and their families about how he can help them with their financial goals and challenges. 

“My background serving in the Army in the U.S. and in Europe has allowed me to find some common ground with military folks when I ask about their careers and learn where they have lived and were stationed,” says Barry. 

“I think they appreciate someone asking about their specialties while they served,” added Barry. “When I share my background as an Army helicopter pilot in Stuttgart West Germany, it shows a potential common bond of military service.” 

Charlie emphasized the importance of acknowledging their service and sacrifice. “Even if not in combat, just the amount of relocation and family separation is something that most people do not come close to experiencing. And you have to genuinely care—they can smell a phony a mile away.” 

Lastly, Mike says it’s all about trust. 

“Whether it’s been 20+ years with retirement like me or someone that did two or three years, we can always connect with that commonality. You have to have that first—that trust—before you can move into any of the business discussion when it comes to financial planning.” 

Mike added on, “I still think my background and experiences allow me to connect with non-military clients as well. It might just take us a little bit longer to find instead of that instant connection.” 


About Mike, Barry and Charlie 

Mike Leupold, Financial Consultant, Schwab

I graduated from the Naval Academy in 1989 and served 24.5 years as a Navy Pilot, retiring in late 2013. I then joined USAA in 2014 which was acquired by Charles Schwab in May of 2020.

(Left: My 1989 U.S. Naval Academy (USNA) graduation picture, Top Right: Standing in front of an MIG aircraft at Al Asad Airbase, Iraq, Lower Right: My family and I at my retirement ceremony in June 2013)

Barry O’Shea, VP Financial Consultant, Schwab 

I was born in Wurzburg US Army Hospital, West Germany, received a 4 year Army ROTC scholarship to Univ of Colorado Boulder. I served 4 years in Stuttgart, West Germany (1986-89) with 4-159 Aviation Battalion as Flight Operations Officer, also 2-135 Aviation Battalion at Buckley Air Nat Guard Base, Denver COLO  1992-94, separated rank was a Captain with 7yrs+ service in total (no pension). 

I also have many family members who served: 

  • My maternal grandfather, Walter Warnock, US Navy enlisted in WW I, Bayonne, NJ and NYC area 1917-1918. 
  • My father, William O’Shea, retired US Army Lt Colonel with 20 years of service, Military Police LT in Wurzburg, West Germany with 3rd Infantry Division HQ 1960-62, then US Army Reserves in Kearny NJ (Civil Affairs).
  • My father-in-law, Conrad Sletta, was in the US Army Air Corps in WW II stationed in Dakar, Senegal, Africa 1945-46. 
  • My wife’s uncle, Lester Sletta, was in the Army in WW II, trained at Camp Carson, Colorado Springs and Camp Hale, Leadville, CO-joined the 2nd Infantry Division in Brittany, France in July 1944 and later was wounded/ taken as a POW in Battle of the Bulge, Krinkelt, Belgium Dec 18, 1944. Luckily survived POW camp in Northern Germany and later moved to Colo Springs after WW II. 
  • My brother, Brian O’Shea-served in the 2nd Infantry Division in South Korea, 1990. 

(Garmisch, West Germany, 1988, I’m in the middle with my pilot & crew chief) 

Charlie Stover, VP Financial Consultant, Schwab 

I’m a USMA Grad, and served 7.5 years infantry and Special Operations Officer in the US Army. 

My father also served: 20 yr US Air Force veteran and 17 years as a Civil servant for US Marine Corps.   

(My Dad and I at graduation week. This is the only uniformed picture we got to take together.)