Tony Holland became a minority owner of the Orioles last year, surpassing his childhood dreams. Holland grew up in a single-parent household in Brunswick, Maryland, and is now CEO of his own company. Photo Courtesy of Tony Holland

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The railroad tracks still run through Brunswick, Maryland.

For generations, they carried freight through the Frederick County town, but for a young Tony Holland they also marked the edge of the world he knew.

Brunswick in the 1970s, when he was growing up, was a blue-collar community where people worked hard, neighbors knew each other, and life was measured less by ambition than by reliability. It was a good place to be a kid, Holland said, but it was also a place where the horizon could feel close.

“It was a small worldview,” he recalled.

His mother, raising him and his younger brother on her own, quietly expanded her sons’ world with trips to Washington, D.C. Holland remembers looking at the office buildings, museums and professionals hurrying along sidewalks and asking himself a question that would shape much of his life: “What do these people do that makes them successful?”

He didn’t know it then, but he wasn’t really asking about money. He was asking how people build meaningful lives.

Today, Holland is chief executive of Global Premier Benefits, a leader in the Medicare insurance industry. He’s also a managing partner at insurance company Integrity Marketing Group as well as a member of the Baltimore Orioles ownership group.

Becoming part-owner of the Orioles last year was, for the lifelong Marylander, a full-circle moment.

“I remember watching the Baltimore Orioles back in the 1970s on a black-and-white television, with the kind of antenna you had to adjust and put aluminum foil on to get good reception,” he recalled. “I saw my first game as a devoted six-year-old fan at Memorial Stadium. The tickets were $2.50.”

Difficult upbringing

Growing up in a single-parent household wasn’t always easy. Unsure about his biracial identity and later living with an abusive stepfather, Holland found some escape in sports and television.

Money was tight, but he discovered a knack for entrepreneurship at a young age, selling cans and even breaking a sales record for selling jewelry for the Glee Club.

At Johns Hopkins on an academic scholarship, Holland’s curiosity led him first toward medicine. There was just one obstacle: “I had a phobia of blood,” he said with a laugh.

Medicine was out.

Like many young people in the 1980s, Holland was captivated by the excitement surrounding Wall Street. After graduation, he was recruited by a New York firm. The reality was less glamorous.

“I learned the hard way that being a stockbroker may just mean being broke,” he said.

Defeated, he moved back to Maryland. At 23, he felt he had failed. “I had a top degree, but I was lost.”

Back in Baltimore, for a time he lived out of a van — a red van with shag carpeting, an eight track and, yes, a little black-and-white TV. He ran a painting business, bartended and waited tables at Liberatore’s. Some days he survived on scraps left behind in the restaurant because there wasn’t enough money for dinner.

“I was going to do whatever it took. I always had two, three jobs, just like my mom did when she raised us. My mom never took welfare, never took a check, never got child support.”

Looking back, he tells the story without embarrassment. Failure, he believes, can teach you. It also prepared him for the moment that changed everything.

Opportunity didn’t arrive through a corporate recruiter or a wealthy investor. A bartender heard Holland’s story and mentioned an opening at an insurance company in Towson.

“One encounter, one introduction can change your life,” Holland said.

He took the job.

More than three decades later, he is still building on that decision.

Helping older adults

Insurance, particularly Medicare, isn’t an industry most people dream about entering. Holland understands that. Yet he discovered that helping older adults navigate one of the most complicated transitions of their lives required far more than technical knowledge; it required trust.

Every client had a different story. A recent retiree was uncertain about healthcare. A widow tried to make sense of unfamiliar choices. A couple wondered whether they had saved enough. Listening to them became as important as advising.

Over time, Holland built a business, but he also built a philosophy. Success, he came to believe, isn’t simply about achievement; it’s about service.

“The best way to help yourself is to help others. I call it the ripple effect, circles of service extending forever outward,” he said.

Today, Holland’s businesses work with thousands of agents and brokers in 32 states as Medicare navigators.

“Everyone has a special gift, and everyone wants to belong to something special. A leader creates an environment to make those dreams possible. Don’t be a boss; be a leader.”

That conviction extends well beyond the office. As a football coach in Carroll County, Holland learns how to listen, teach and inspire young players, no matter their ability. The effort has resulted in 13 championships.

Never forgetting how one person helped him when he was a struggling 20-something, Holland also mentors entrepreneurs: “Connecting people is the main business of my life,” he said.

He gives back in other ways, investing in local communities, youth sports programs and philanthropic causes such as the Kennedy Krieger Institute’s holiday programs for children.

His optimism is unmistakable. So is his realism. Like many of us over 50, he knows what it feels like to fail, and he knows what it feels like to rebuild. Perhaps that’s why he speaks less about avoiding adversity than about responding to it.

“You can’t always control circumstances,” he said. “You can control your attitude.”

Finding a lost father

Years after establishing himself professionally, another unexpected turn reshaped Holland’s life.

For most of his life, Holland never knew his biological father.

Then a DNA test through Ancestry connected him to the man whose identity had remained a mystery for decades.

“We spent 14 months getting to know each other before he passed away. It turns out he was searching for me as well,” Holland said. “It was a huge blessing to spend time with him after 46 years. I also gained three half-sisters who continue to be part of my family as well.”

Their reunion answered questions Holland had carried since childhood and also made him grateful for the family he had built with his wife, Kathy, and their three children.

Holland speaks often about fatherhood, mentoring and legacy, perhaps because he understands the power of both their absence and presence.

No plans to slow down

Today, Holland’s interests continue to evolve. While many people his age are planning retirement, he is studying artificial intelligence (he owns three AI companies), exploring private equity (he owns two firms), thinking about community development and always asking where he can make the greatest difference.

What matters most to him is the chance to leave people better than he found them. Holland has learned to use his knack for self-promotion to advocate for communities in need. After all, Holland knows the measure of a life is not how many doors open, but what you do after you walk through them — and how many others you help.

“All you can do is all you can do,” he said. “And all you can do is enough.”

As a devout Catholic, he leans on his faith. As a businessman, he knows that corporate success and community service can work together to change lives. “People want to change if you just give them the chance. And a little push forward,” he said.

For Holland, success goes beyond accolades and acquisitions. He is laser-focused on creating opportunities — for employees, for clients, for young people he mentors, and for the state he still proudly calls home.

“I’ve always believed that where you come from matters,” Holland said. “Maryland gave me a lot and no matter where I am or when I am, Maryland is my heart.”

Correction: The print version of this article stated that Holland’s biological father was a biologist. In fact, he worked in the hospitality industry. In addition, the original article did not clarify that Holland does more than study AI and explore private equity; as this version states, he owns three AI companies and two private equity firms.