This year marks Prestar’s 20th anniversary, and if I’m honest, writing that sentence still catches me off guard. Twenty years ago, I wasn’t picturing an insurance appraisal company serving condominium associations, HOAs, property managers, and insurance carriers across Florida and the Southeast. I was picturing a red table.
Where It Actually Started
In the summer of 2006, three of us sat down at that table in Saint Petersburg, Florida, and decided to build something together. I came out of the corporate training and learning & development world at JPMorgan Chase. One of my co-founders was a Florida Property Appraiser. The other had spent years running the commercial division at a rival insurance appraisal company. On paper, we were an odd combination. In practice, it worked, because none of us wanted to keep operating inside the rigid structures we’d come from.
We weren’t chasing a trend. We saw a real gap: condo associations, HOAs, and commercial property owners needed accurate, defensible replacement cost appraisals to secure and maintain adequate insurance coverage, and the industry serving them wasn’t especially interested in customer service. We thought we could do it differently.
The early days were exactly as hard as everyone warns you they’ll be. Long days, sleepless nights, three guys and their savings in a modest office, hoping the phone would ring. It finally did — one call from an insurance agent who needed an appraisal fast. We took it seriously, delivered, and that agent told other agents. That’s genuinely how this business grew in the beginning: not through advertising, but through insurance carriers and underwriters trusting that when Prestar’s name was on a report, the numbers were right.
What We Got Right Early, and Never Let Go Of
Here’s the part of this story I actually want to spend time on, because it matters more to me than the founding myth.
From the very beginning, we were obsessive about two things: building a company our employees genuinely wanted to work for, and delivering the kind of customer service this industry didn’t have. Not as a slogan — as an operating principle. We wanted people who called Prestar to reach a live person. We wanted our team to feel like their work mattered, because in an industry where a missed valuation can cost an association tens of thousands of dollars during a claim, it does matter.
What I didn’t fully appreciate at the time is how much discipline that commitment would require over the next two decades. Work norms have changed dramatically since 2006. Remote work, shifting expectations around flexibility, entirely new generations entering the workforce with different assumptions about what a job should give them back — the whole landscape moved. A lot of companies moved with it in ways that diluted what made them good in the first place. We didn’t. We stayed ingrained in that original model: take care of the people doing the work, and take care of the people we serve, and the rest tends to follow.
I won’t pretend that’s always been the easy path. It would have been simpler, at various points, to cut corners on staffing, on training, on response times, in the name of scaling faster. We didn’t do that. And twenty years in, I think that stubbornness is the actual reason Prestar is still here — not the founding story, not the red table, but the fact that we never let go of what the red table represented.
Two Decades of a Changing Industry
The insurance appraisal industry itself looks almost nothing like it did in 2006. Florida’s regulatory environment has tightened dramatically, especially since the Surfside condominium collapse reshaped how the state approaches condo and HOA compliance. Structural Integrity Reserve Studies, milestone inspections, and legislation like HB 913 have transformed what boards, property managers, and community association managers are legally required to have on file — and how often.
Insurance carriers and underwriters have become far less forgiving of outdated or inaccurate replacement cost valuations. Underinsurance isn’t a theoretical risk anymore; it’s a documented reason associations get hit with coinsurance penalties or non-renewals. Boards today are managing fiduciary responsibility under a level of scrutiny that simply didn’t exist when we started. Wind mitigation inspections, once an afterthought, are now central to how associations control premium costs in a hard Florida insurance market.
We’ve adapted to every one of those shifts, because we’ve had to. What hasn’t shifted is why associations, property managers, and agents keep calling us: they want optimal coverage, an accurate number, and someone who picks up the phone. Nearly 18,000 completed appraisals later, that hasn’t changed.
Twenty Years of Trust
I think about the people who’ve made this possible more than I think about the milestone itself. The employees who’ve stayed because the culture we built was real, not performative. The property managers and community association managers who’ve trusted us appraisal after appraisal, renewal after renewal. The insurance agents and carriers who’ve come to recognize Prestar’s name on a report and know exactly what that means. The HOA boards who’ve called us specifically because they wanted to do right by their communities and needed a partner who understood what that actually required.
Twenty years is a long time to stay committed to a simple idea: build a good place to work, and take exceptional care of the people who trust you with their property’s financial protection. We got that right at a red table in 2006, and it’s still the whole plan today.
Here’s to the next twenty.
— Jason Lintner, Founder & COO, Prestar Services
