When Bob Stahl talks about his life and career, he doesn’t dwell much on milestones or accolades. “I never really thought about it that way,” he says. “I just woke up every day and went to work.”
Sounds simple enough, but maybe more nonchalant than you’d think, considering the size and scope of his business.
Stahl established Stahl & Associates in 1983. In 2023, Higginbotham, headquartered in Fort Worth, Texas, partnered with Stahl & Associates Insurance which, at the time, was the largest privately held agency in Florida. Today, Stahl & Associates, part of Higginbotham, all told is nearing $1 billion, in revenue.
But that simple, unwavering drive, instilled by his hardworking parents and sharpened by his own path, built one of the largest insurance firms in Florida. And more than 40 years later, with both of his children now in leadership roles, Stahl has shaped a multi-generational legacy grounded in ethics, discipline and service.
A REBEL WITHOUT A CAUSE, YET
Born in Pittsburgh and raised in a tight-knit, working-class family, Stahl was 13 years old when his father, a steelworker, took a job transfer to St. Petersburg. The move was prompted, in part, by his mother’s lifelong battle with kidney disease. Doctors suggested that the warmer climate of Florida would be beneficial to her health. The family arrived in 1965 and quickly planted roots.
Bob’s mother, a cultured and resilient woman who was adopted as a baby and spoke fluent German, instilled grace and high expectations in her children. His father, a World War II veteran, was charismatic and driven, as Stahl describes him. While he worked in corporate America, he envisioned a future with more freedom, and independence, for his son.
Stahl says, laughing. “He’d say, ‘Don’t be like me. Go out and do your own thing.’”
After growing up in St. Petersburg, Stahl attended Florida State University, majoring in marketing. He took one class on the topic of insurance and admits; he mostly slept through it.
With a gleam in his eye, Stahl confesses he was a bit of a rebel. After college, while still figuring out what he wanted to do with his life, he bought a van with a friend and headed out west. Long hair, past his shoulders, Vietnam-era restlessness in the air and no particular destination in mind.
“We went to Mexico, up the California coast, Colorado, Montana, Wyoming,” he says. “We hit all the national parks. Lived out of the van for a little while. It was a couple of months of freedom and figuring things out.”
Eventually, reality called. Stahl returned home, to St. Pete, took a job in insurance and began building a real foundation. That’s when Kathy came back into his life.
Kathy and Stahl met briefly, through mutual friends, during their Florida State days, but the relationship didn’t blossom until several years later. They have been married for 40 years.
Their early days together were entrenched in the beach town community they loved. “We used to hang out on the waterfront lot, next to where our house is now. That’s where all our friends would gather,” he says. “We’d have a few beers, watch the sunset. It was special to us.” So special, in fact, that after they married, they bought that exact lot and, years later, built their dream home on it. It’s where they still live today.
They raised their kids on St. Pete Beach and made their home a neighborhood headquarters for everything from soccer team dinners to prom night photo opportunities.
The family enjoys traveling. They love visiting their second home in Montana to ski. The Montana home, which was designed by Kathy, has been featured in Mountain Living Magazine. When they’re not exploring the mountains, they’re making memories of cuba diving and boating in the Bahamas.
The cozy, family-minded lifestyle is still present. On the afternoon of this TBBW interview, both children — and the grand dog — were gathered around the kitchen table, swapping memories and laughter. Even with rebuilding happening around them, the result of the storms that damaged so many homes across the Tampa Bay area in 2024, it is still home, and the kids still like to gather there.
BACK TO BUSINESS
When Stahl graduated, in the midst of a sluggish job market, he took what he could get. He took a position as a claims adjuster with Royal Insurance.
It wasn’t glamorous, but it taught him how to investigate, solve problems and work with both people and policies. “I thought I knew more about the cases than the attorneys,” he recalls. “But they were the ones making all the money. I figured, maybe I should go to law school.”
That plan didn’t pan out. After multiple rejections, he redirected his ambitions and, instead, pursued an MBA at night and later transitioned to a marketing role within Royal. And that’s where everything changed, he says. “I started realizing, these agencies were doing pretty well,” he says. “Maybe I should be doing this.”
He’d already launched a small side business with his father and saved up some money. In 1983, he purchased a small insurance agency, in Seminole, putting down $50,000 — some borrowed — and pouring his last $1,500 into a business checking account. “I didn’t have a penny to my name after that,” he says.
There was no salary for him in those early days, but he hustled. “If I could sell just a couple grand a month, I could make it work.”
LINES OF SUCCESSION
Over the next four decades, Stahl & Associates Insurance experienced significant growth thanks, in part, to Stahl’s combination of street smarts, financial discipline and an eye for smart acquisitions. He purchased more than 30 agencies over the years, not just to grow the client base, but to gain talent, relationships and market reach. At its height, Stahl & Associates was the largest privately held insurance agency in Florida.
But Stahl didn’t do it by cutting corners or over-promising. His business philosophy was borrowed from his martial arts training — he holds black belts in both Japanese karate and TaeKwonDo — which emphasized humility, discipline and preparation.
“It’s all about respect,” he says. “You’ve got to protect people. That’s a huge responsibility.”
That mentality shaped the way he mentored young salespeople and led his agency. He emphasized technical knowledge, not just quotas. “Don’t go out there and sell something you can’t back up,” he told his team. “We can’t afford to make mistakes.”
That standard also extended to his personal life. He coached his kids’ sports teams, showed up at every game and made their St. Pete Beach home the unofficial headquarters for school events and post-game pizza nights. “Our place became the focal point,” he recalls. “We had the lot next door, so we turned it into a ball field.”
Through it all, family stayed a priority and Stahl credits Kathy for always being his biggest supporter and cheerleader. He even credits her for helping land his first client at the Stahl agency.
Both of Bob’s children, Brittany and Robby, eventually joined the family business, though not by force. “I didn’t push them,” Stahl says. “They found their own way into it.”
Brittany, a former CNN associate producer with a master’s in journalism from New York University, initially joined “temporarily” to help with communications. She currently serves as managing partner and leads the benefits division, in addition to helping shape national training programs and initiatives for women in leadership for Higginbotham.
Robby, a former college baseball player, actor and model, in Los Angeles, came into the industry after working for a firm in California – performing very successfully. So, he and his dad thought, why not do it for the family business? Now, he’s Stahl’s top producer and a regional sales leader with Higginbotham.
The decision to join Higginbotham wasn’t made lightly, we are told. Stahl had long resisted acquisition offers, determined to remain independent. But as the industry evolved and larger national players began squeezing out regional firms, he saw the writing on the wall.
“I wanted to make sure Brittany and Robby could still compete,” he says. “I didn’t want to leave them something that was going to shrink.”
The deal was a strategic one. Stahl’s family became a significant shareholder in Higginbotham, which is nearing $1 billion in revenue in 2025. More importantly, the company’s employee ownership model aligned with Stahl’s values. “We’ve got 25-year-olds with stock in the company now,” Brittany says. “That changes lives.”
It also helps attract and retain top talent — a key priority in a post-pandemic insurance market rocked by climate risks, legislative changes and rising costs. Stahl is especially vocal about educating clients and policyholders, particularly about flood insurance and hurricane risk. “There’s a massive education gap,” he says. “People don’t know what they don’t know and, unfortunately, a lot of agents don’t either.”
A TRANSFORMATIVE EXPERIENCE
Changing lives is a common theme among the Stahls, with philanthropy being another cornerstone of their ethos. The Stahl family supports more than two dozen nonprofits, with Johns Hopkins All Children’s Hospital as a primary focus. They also champion Family Reach, a Boston-based organization that pays essential bills for families whose children are undergoing cancer treatment. And for years, Stahl was the lead sponsor of the Suncoast Hospice annual gala.
It’s truly a challenge to get him to talk about just how much he gives back, not one to brag.
But, as often is the case, when it comes to his children, he’s more than happy to brag, just a little.
“I guess I am proud,” he says, pausing. “I’m fortunate. I’ve got two kids who are better than me and I get to work with them every day. What more could I want?”
–Photos by Evan Smith
Three Philosophies That Shaped Bob Stahl’s Leadership
- Respect is everything.
“It’s all about respect,” Stahl says.
2. You can’t afford to fake it.
“Don’t go out there and sell something you can’t back up,” he often told young producers. He emphasizes technical knowledge over empty salesmanship.
3. There’s no substitute for hustle.
“When the bell rings, you come out swinging,” he says. “Every day, you’ve got to try to take a step forward because you never know when your biggest opportunity will come.”
