Military veterans turned fintech leaders on the values needed to make it

November 11, 2022 5:19 PM

Commitment. Attention to detail. Trustworthiness.

U.S. Navy Veteran Rory Berry, the director of marketing at New-York based fintech firm Pontera honed these values over the course of nearly two decades in the military. They've also enabled him to prosper on a different battlefield: financial services.

Rory Berry, the director of marketing for Pontera

Provided by Rory Berry

The commitment to see every task through to the end. Attention to detail that ensures nothing is overlooked. Trustworthiness to keep both clients and fellow soldiers at ease when called upon to make decisions in high-pressure situations.

"There are so many overlaps, like the fact that everybody on a team needs to do their part. And a lot of it comes down to accountability, which is so important in the military, and it really is a cornerstone of financial services as well," Berry said. "Being accountable to what your mission or your mandate is. Being accountable to your teammates. Being accountable to your clients or your supported command.

Last but not least, he said, "you really have to have a level of unimpeachable trustworthiness and the confidence of those around you. Because in both situations, if you lose the confidence of those around you, you're done."

U.S. Army Veteran Patrick McKenna, the executive chairman and co-founder at Baltimore, Maryland-based online RIA Facet Wealth, also believes that serving his country prepared him for a career on Wall Street — and in ways that continue to surprise him today.

Patrick McKenna, executive chairman and co-founder of Facet Wealth

From the ability to adapt to difficult circumstances to an eagerness to work with people from all walks of life, McKenna said the military made him a better teammate, a better man and a better entrepreneur.

"I thought about this when I kind of first left, but my service didn't end when I took the uniform off. And I have a career where I can continue to be of service. That's why I think my military experience along with my Wall Street and M&A experience … they fit so well together in the RIA space," McKenna said. "Because I think if you have a fully transactional mindset it doesn't work well in either world or in entrepreneurship. Because you're not in a transactional business, particularly when you're in the asset and wealth management or CFP world. You're in a relationship business."

In honor of Veterans Day 2022, Financial Planning spoke to this pair of military veterans-turned-fintech-leaders about how lessons learned during their time in the service primed them for successful careers in financial services.

Serving beyond the service

Berry said a passion for military service is in his blood. He comes from a long line of veterans, and was excited for the opportunity to follow in their footsteps.

So after finishing high school, he entered a Navy ROTC program. That allowed him to pay for a college education at Stanford University, where he graduated with honors and a bachelor's degree in symbolic systems with a focus on neuroscience.

The young ensign followed college by reporting to the USS Germantown in San Diego, California. While there, he managed 18 sailors in the maintenance and operation of the auxiliary machinery equipment.

"I served aboard that ship for a few years, and then went into the reserves. A couple years later in 2011, I ended up getting mobilized and went back and did about the least Navy assignment you could. I would spend most of the time far from water in Kuwait, Iraq and Afghanistan, doing a logistics mission that the Navy was helping out with," Berry said. "I got pulled back as an individual augmentee and spent another year there. Then I came back and have been in the reserves ever since. I'm now at the rank of commander and I've been in for 19 years."

As Veterans Day 2022 rolls out, Berry reflects on his journey from ensign to commander and on the meaning, and weight, of being a veteran..

Berry — who notes that he's not the kind of person eager to tattoo his car with 20 "I'm a veteran" bumper stickers — would rather highlight the hard work done by others, and show thanks to those who have helped him along the way.

"A lot of people serve the country in a lot of different ways. I think that everybody's drawn to different callings, and I think we're reaching a good balance," he said. "There was almost an oversaturation of sort of hero worship in the post-911 era. And I think we've kind of corrected back to making sure that we're honoring all the teachers. And firefighters. And all the members of the community that make America such a great place."

He cited an analogue between the military uniform and the traditional suit and tie of the finance industry. "The more attention people are paying to details in one thing is usually a good indicator of how well they're paying attention to details elsewhere," he said. "In the military, it's 'you gotta shine your boots.' But it doesn't really matter that your boots are shining. It matters that you care enough about that detail, and that people know that you're paying attention to the small things. And you see that same thing with people in our industry wearing nice shoes or nice watches or things like that.

But the most important parallel between both worlds is trust.

"In the military, it's a level of trust over the protecting and taking of lives, which is a very serious matter. In the same regard in the financial services industry, it's the stewardship of somebody's entire retirement. Or their entire portfolio. It's not a minor matter," he said.

Regarding why he continues to be active in the reserves as the director of administration for Seventh Fleet's Future Plans Reserve Detachment, Berry said the satisfying nature of the mission is what keeps him hard at work.

"I hope that there's never a need. But I feel strongly that it's important that we're ready for the challenges that may come. And when there's not a primary mission to be served, what else can we do to help the community or help in other ways?" he said. "It's sort of my volunteer organization to an extent. It's knowing that I'm doing my part to make sure that we're ready for whatever challenges may face the nation. And it's maintaining a strong connection to the greater community far beyond myself."

This Veterans Day, Berry planned to touch base with those he has served alongside over the past 19 years.

"There's a big push in the veteran community to check on each other. And it's a good chance to actually reach out to people I served with and haven't talked to in a long time. It's the day to reach out to the brothers and sisters in arms that I've known in the past and make sure that they're doing well and see how life has treated them," he said. "I take the extra effort to reach out to friends from service. And then, you know, usually get a free coffee or something."

Small town kid turned entrepreneur

McKenna found the Army as a young man who was ready to take his next big step. Born and raised in Placerville, California, a small town in the foothills with a current population of around 10,000 people, he was readying himself to be the first person in his family to attend college when he enlisted.

McKenna said he always had a strong sense of service, even when he was in grade school.

"Instead of wanting to be student body president, I was Key Club president," he said. "And I loved a lot of things about the military, but I really was interested in the service side of it."

The son of a mother who worked as a mail carrier for more than 30 years, McKenna said he grew up having a very middle class experience — one supported by the hard work of his mom.

He wanted to make her, and everyone else who supported him, proud. So he dedicated himself to becoming the first one in his family to pursue higher education after graduating high school.

"I was looking at different ways to get there, and the service academy really felt like a good fit for me. But I'm an only child, and my mom said to me, 'you know. It'd be great if you can stay in California and stay closer to home,'" he said. "She and I started talking about (Army) ROTC, and when I looked into it, it actually seemed like such a great fit because I can fulfill that interest in military service and get a scholarship and go to college in California."

That decision led to a full ride ROTC scholarship that landed him at the University of Southern California, close enough for his mom to drop in but far enough to establish his own independence.

As an undergraduate, McKenna majored in accounting. He knew he wanted a skill that would allow him to always put food on the table, but also allow him to learn the language of business.

His time at USC ended with him as a distinguished military graduate, a designation bestowed upon the top-ranking ROTC students. McKenna met that honor with great excitement because it meant he was more likely to be selected for active duty.

With an interest in technology, he kept an extremely busy schedule over the next four years. He was a signal corps officer specializing in cyber command at Fort Gordon in Georgia. Then he went to airborne school to learn how to jump out of planes. Then he went to Alaska for warfare and survival training. Then he went to Korea to work in military intelligence as a signal corps officer handling technology operations for his intel group.

"From there, I went down to Panama. I went to language school to learn Spanish and eventually I ended up working for Gen. Barry McCaffrey who was the commander-in-chief of U.S. forces in South America. So I spent about a year and a half working on a four-star general staff as a very junior officer … an incredible experience," McKenna said. That experience would grow into him working at a Cuban refugee camp in the early '90s, helping Cubans trying to get to the United States.

"I ran this thing called the Family Support Center, which was one of the most heartfelt things I did in the military. It was reconnecting Cuban families from around the world with the Cubans who were escaping the tyranny of Castro's Cuba," he said."It was this wonderful connection of service and humanity and people trying to do the best with their lives. So my four years in the military were just amazing."

With so much pivoting and shifting responsibilities in just four years, McKenna relied on his military training to remain disciplined. He was handed responsibility beyond that of the average 20-something college graduate.

Now an Army lieutenant, McKenna followed his time in the service with graduate school at Georgetown University when he developed a strong interest in investment banking, and earned a formal entry to Wall Street by way of J.P Morgan.

The years that came after were just as action-packed as his four years in the Army, and included co-founding four businesses, two investment funds and one nonprofit.

"There were definitely a lot of things that I was probably inexperienced in. But that's another thing about military service. You're adaptive and you have a natural entrepreneurial orientation. And you'll just put the hours in to figure out how to achieve the goal," McKenna said. "And then another cool thing was there were other veterans in my class and a few others around the bank, and we had a way of just finding each other. The military network is really strong, and people are willing to help each other. So I was able to jump into a very high level Wall Street job with my military experience and a couple years of graduate school."

Today, as one of Facet's leaders, McKenna maintains his military values and is quick to put others first. He said he hinks back to making his mother proud and wanting to provide opportunities to other small town kids who want to make an impact.

Sowhen he thinks of the term "financial services," he focuses on the second word more than the first.

"My mom worked hard. It was a very good upbringing. But we certainly didn't have somebody who was on our side when we were thinking about financial decisions," McKenna said. "Everybody was a transaction. A mortgage. Or credit card. Or a bank loan. Everything's a transaction, not a relationship. And as I learned more I said, 'what would it take to get what I'm getting as a high net worth person and offer that in the same manner, but at the right cost, to a bigger market?' And honestly, that is the foundation of Facet."