Tony Holland grew up watching Orioles games on his 13-inch television, and his favorite memory as a fan is attending his first game at Memorial Stadium when he was 6 or 7 years old.

Now, nearly 50 years later, Holland has become a minority owner of the ballclub.

Holland, 55 of Westminster, is CEO of Maryland-based Global Premiere Benefits and Managing Partner at Integrity.com. In an interview with The Baltimore Sun, Holland discussed his background, Orioles fandom and excitement about joining the ownership group.

(Editor’s note: Questions and answers have been edited for brevity and clarity.)

Q: What was it like growing up as an Orioles fan?

A: I grew up in a town called Brunswick. It was a railroad town in the 70s, and we used to watch the Orioles on an old black and white TV, a 13-inch TV with the rabbit ears. We always loved the Orioles. My favorite players back in the day, obviously Cal Ripken, Jim Palmer, Eddie Murray, Earl Weaver. I can still remember my first game. I might have been 6 or 7 years old at Memorial Stadium, and the tickets were like $2.50 back then to go see a game. I was honored and privileged to be able to experience that as a kid and watch the World Series in 1983 when we beat the Phillies. It was great to see that. Still disappointed in the 1979 Series when we lost to the Pittsburgh Pirates. That was my heartbreak moment as a kid, watching us lose. We should have won that one.

What are some of your favorite memories as an Orioles fan?

That first game at Memorial Stadium back when I was a kid. Of course, watching the World Series in 1983 was a great moment. I used to remember Earl Weaver when he’d get mad at the umpire, he would scrape the dirt on home plate, it was always exciting to see that. It was always electrifying when he got upset, so it was kind of nice to see that. And also when Cal Ripken broke the record, that was a nice experience. That was probably one of the highlights in Baltimore, besides the Ravens winning the Super Bowl and us winning the World Series. That was probably one of the biggest moments because I was there at that game, witnessing history being made.

Aside from baseball, what was your childhood like growing up in Brunswick?

I grew up in a single-parent household. I didn’t know my father, and it was tough as a kid dealing with that. My mom worked multiple jobs. Went to Brunswick Elementary all the way through high school, graduated in 1988. I went on to Johns Hopkins University on a scholarship. I was a pretty good football player. Not good at baseball, but I was good at football and track. I ran track and played football at Johns Hopkins and thought I was going to go into medicine. I studied medicine as pre-med and also engineering and decided that wasn’t for me. I was actually waiting tables at Liberatore’s. I was on my own, trying to make ends meet, actually briefly lived out of my van. I was a guy waiting tables living out of an old 1982 Dodge conversion van band. It was a bright fire engine red, had a flame on the side, a little teardrop in the back and shag carpet. I lived out of it for a little bit while I was waiting tables at Liberatore’s and I got into the insurance business on a whim from the bartender that was there. He said, ‘Why don’t you give insurance a shot?’ and the rest is history.

What position did you play in football at Johns Hopkins?

I was recruited to be a defensive back because of my size. I was about 5-8, 5-9. I played linebacker in high school and fullback, but I played pretty much wherever the coach wanted me. I played linebacker. One game I had to play nose guard because our nose guard went down. I’m going against guys who were 6-4, 6-5 and 280-plus. I had to step in and try to be an immovable object. It was a very good experience. I wouldn’t trade it for anything else.

Once you got into the insurance industry, how did your career progress from there?

It was a tough moment. It was 1994 when I was like, ‘I got to get something together, I got to figure this out.’ I had a Hopkins degree. I just knew I had to do something bigger and better in my life. I studied the guy Tony Robbins. I read every one of his books. I love to read. I read every one of his books. I went to a seminar, and it totally turned my life around. I started changing the way I thought about life and things. I just realized my predicament because of my upbringing and some of the adversities I had to overcome as a kid. I was always a pretty good student, but I just didn’t understand how success works. I used to remember when I was a kid, mom would drive us down to Rockville, where she worked at Hewlett Packard, and we’d go through Potomac, and I’d see all these mega mansions. I was like, ‘What do these people do to have that?’ I just always wanted to figure it out. What’s the secret to success? I got into insurance, got really, really good at sales. Started with a company called American Income Life out of Towson. I worked for a guy named Scott Alexander, and he taught me the business and taught me how to grow a company. I built multiple insurance companies. I started my own company called Holland Insurance Group in July of 2000 and then I started another company in October of 2010. At one time, I was the largest distribution partner in the country for Cigna healthcare for their Medicare. Then in December 2021, I sold both my agencies to Integrity, and I became managing partner of Integrity. We’re the largest insurance tech company in the world.

How excited are you to join the Orioles as a minority owner?

I’ve always wanted to own a sports franchise. I love sports, and when this came about, it was a dream come true. Being part of the ownership group, especially the minority owners and the principal owner, they’re just amazing people. It was a team I’ve loved my whole life. It’s a dream come true. It’s also a way to give back to the community. Baltimore has been so great to me — from starting companies and building my life and building my business empire. It was kind of a nice way to give back to the community that’s given me so much. I’ve also invested heavily in the community of sports for football, youth football, also baseball. I’ve done a lot of work there, not only investing in those teams, the youth programs in the community — especially in Carroll County — but I actually coached a lot of the teams. Those are some of my proud moments, giving back to the community in that regard. Playing sports as a kid helped develop me into the man I am today. It was one of my great joys to give back in that regard.

How excited are you about the future of the Orioles organization?

I’m very excited. I think the fans are going to be excited as well. I think people can sense the excitement. It’s a good vibe. There’s so many great people involved in this organization, from the leadership all the way down. So I’m really excited about the Baltimore Orioles and looking forward to a championship. We need one. We’re due.

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