Robert “Bob” Stahl founded Stahl & Associates, in 1983. Fast forward to 2023, the company became part of Higginbotham, one of the nation’s largest independent insurance firms. At the time of the partnership, Stahl & Associates was the largest privately held insurance agency in Florida.
But numbers only tell part of the story. What really defines Stahl is the steady drive he learned from his parents, and the values he’s carried forward such as discipline, service and integrity. Now, more than 40 years in, with both of his children in leadership roles, Stahl has built more than just a business, he’s built a legacy.
See photos from the event here.
Read Stahl’s cover story here.
Bridgette Bello, chief executive officer and publisher of Tampa Bay Business and Wealth, interviewed Stahl in front of a live audience at CAN Community Health, in Tampa. This interview has been edited for length and clarity.
What has it been like being Mr. July 2025?
It’s been a really great experience. I’ve heard from a lot of people, some folks I hadn’t talked to in a long time and it’s really been touching, to be honest with you. So, thanks again for having me. I appreciate it.
When we were talking before the event tonight, you brought up one of the questions from the interview, “Do you remember a time you made a mistake.’” You said you had an answer now, what was the mistake?
[During the interview] I said I couldn’t remember making a big mistake, which is not true. Obviously, I made a lot of them, but I think the biggest mistake I ever made was not doing this interview seven years ago when you first wanted me to do it. [Laughter]
I’m going to bet Brittany, or your wife, told you to say that.
No, they didn’t. What else happened to me, tonight, was a young man came up to me, very successful insurance person, and he said, “Hey, you interviewed me 10 years ago.” And I’m like, yeah, I did. How did I miss this one?
So, there’s another [mistake] right there. But the answer I was going to give you was that we built a good business. We continued to build, and so forth, and I did take some risks along the way. I had to, to make some things happen. But sometimes I think I could have stuck it out there a little further. I could have gone for it a little bit more.
It was difficult for me because you get to a certain point, you get some accomplishments and you don’t want to lose that. When you come from nothing, you don’t want to go back to nothing. I think sometimes I was very conservative in my approach and, looking back, I think maybe I should have done that deal or another one. I turned down a lot more deals than I ever did. I did over 35 acquisitions in my time. Looking back, I probably could have pushed the envelope a little bit more.
It’s amazing the number of cover stories we’ve had say that when you know what it feels like to be hungry, you don’t ever want to feel like that again.
You read these stories about these guys that had everything and then had nothing, and they came back. I’m not one of those guys. I don’t want to be like that. I want to get there and stay there and keep going. That was the mindset.
Looking back, what were the key decisions, or values, that helped you turn this into a billion-dollar company?
Survival. I was very frustrated at that point in my life. I worked for an insurance company and part of my job was to develop independent brokers. I was in a perfect scenario to explore opportunities but I was anxious to make something happen.
I had a couple of deals fall through. One guy took my deposit, I had to sue him. Another guy just decided not to do the deal. So, I was really frustrated.
When I got to the agency I ended up buying, I wouldn’t have bought it today based on what I know now, it was in bad shape. There were a lot of problems. It was challenging, to say the least. A lot of late nights, seven days a week. But I always knew we were going to make it somehow, even though one thing after another would come up. Now, it’s a great experience to look back on. It wasn’t so much at the time.
When I was trying to create interesting questions for tonight, through research, I heard you won a court case for Suncoast Hospice. What was that about?
Suncoast Hospice was a client of ours. They were putting an addition onto a building. We insured their existing building, but someone else insured the new one. The new building burned down. All the insurance companies pointed fingers, nobody wanted to pay.
We went to court. I asked Mary Labyak, the founder, if I could testify. I explained how it all worked and that they didn’t do anything wrong, they paid their premiums and the court needed to find in their favor. It worked. They got the money. That started a long relationship with Suncoast Hospice. I learned so much from them about compassion and helping others.
Family is important to you. When your kids look back, what do you want them to say they learned from Dad?
A strong work ethic. Doing the right thing by people. We take care of people’s companies, lives and employees. It’s a huge responsibility. Integrity has always been key.
And personally?
That I was a really cool dude. I did a lot of great, fun things and made life enjoyable.
Speaking of fun things, I heard you hitchhiked through France.
That was three years ago. We were in Bordeaux, with friends, walked a long way into town, it was hot. We decided to hitchhike back. A guy in a tiny car picked us up. I had my shirt tied around my head. It was quite a sight.
You and Brittany both light up when talking about the difference you’ve made in your employees’ lives. What’s the impact of your culture?
A lot of those folks are here tonight, many 30+ years with us. We’re basically a family. That was part of our reason to merge with Higginbotham, so they could continue in a positive environment long after I’m gone. You build bonds with people you can rely on. It works and it’s special.
Last question, if this were your last public talk, what’s the one thing you’d want people to know about you?
That I was totally committed to my craft, my family and my employees, and that I always will be.
ABOUT ‘CEO CONNECT’
TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. M|A Family Capital Partners of Raymond James, Susan Terry Foundation, Spartan Contracting were presenting sponsors. The host sponsor was CAN Community Health. TBBW’s video partner is Empowering Creative.
The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.
Partnering with TBBW provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.
For information about event sponsorship opportunities, email Jason Baker at [email protected].
