Tom Rowland Podcast Episode 942 is my conversation with Jake Holehouse of HH Insurance about the thing every Florida homeowner and boat owner is worried about: insurance. After a brutal back-to-back hurricane season with Helene and Milton, Jake breaks down how building codes really perform, how flood coverage works and where it falls short, why so many boat owners are underinsured, and the specific gaps most people do not know are in their policies until they file a claim.
Listen now: Apple Podcasts · Spotify · Listen in the player · Press play in the audio player on this page.
Jake Holehouse is an insurance expert with HH Insurance who specializes in Florida home and boat insurance. In this episode he breaks down what the back-to-back 2024 hurricane season meant for Florida homeowners and boat owners, how building codes and flood coverage actually work, and the specific gaps most people do not realize are in their policies until it is too late.
Jake explains that Hurricanes Helene and Milton hit within thirteen days, with Helene impacting much of the Southeast. Despite the damage, he says the insurance industry is far better prepared today than it was in 2004 and 2005, which he calls a worse season for the industry. Newer construction held up dramatically better, and resilience is the word he keeps hearing from both Floridians and insurance carriers.
Yes. Jake says the data is clear: newer construction built to the current Florida building code takes far less damage and generates significantly fewer claims. I saw it myself after Irma in the Keys — newer homes kept their roofs while older homes next door lost theirs. He explains that fortification like newer roofs, hurricane shutters, and impact glass can make a house very survivable in a storm.
Jake walks through the National Flood Insurance Program, or NFIP, which underwrites most flood coverage even when a policy carries a brand name like a major carrier. The big catch is the coverage cap: the maximum you can get through the NFIP is $250,000, so a million-dollar home is badly underinsured for flood, which is a real problem for slab-on-grade homes that took on water this season.
Jake explains that boat owners frequently get pushed toward the cheapest policy to satisfy loan ratios, and that leaves dangerous gaps. The two he highlights are coverage for the Bahamas and nighttime navigation — neither is included in a base policy. He uses my own boat as the example: my old policy did not cover the Bahamas or nighttime navigation, and Jake and Landon fixed it fast by adding the right coverage.
Jake's advice is to fortify. Newer roofs, hurricane shutters, impact glass, and other improvements reduce the likelihood of claims, which is what drives rate pressure. Old tile roofs that are forty or fifty years old create the most pressure because carriers know claims are coming. Fortify the house and you might lose landscaping in a storm, but you keep the house.
Tom Rowland Podcast Episode 942 with Jake Holehouse of HH Insurance is available on Apple Podcasts, Spotify, YouTube, and iHeartRadio. Press play in the audio player on this page to hear the full conversation about home and boat insurance.
Every person I know who owns a house in Florida was saying the same thing after this hurricane season: I do not even know if I will be able to get insurance next year. People who do not work in the insurance world were genuinely scared, some saying you would have to pay cash for a house to own one here. That is exactly why I wanted to sit down with Jake. He actually knows how this works, and he fixed gaps in my own policy that I did not know existed. I came into this one with the same questions everybody else has.
Press play in the audio player on this page to hear the whole conversation.
Jake puts Helene and Milton in context — two very different storms thirteen days apart, hammering Florida and much of the Southeast. But his bigger point surprised me: as bad as it was, 2004 and 2005 were worse for the insurance industry, and carriers are far better prepared now. He explains why the industry plans for this kind of season annually and what that means for your rate next year. Listen to that part of the episode.
I saw this with my own eyes after Irma in the Keys: you would walk a street and every newer house kept its roof while the older house in between lost everything. Jake confirms the data backs it up — newer construction built to the current Florida code takes far less damage and files far fewer claims. He explains how fortification like impact glass and shutters changes the math on survivability. Press play to hear it.
This is the part most people get wrong. Jake explains that even a policy with a big carrier's name on it is usually underwritten by the National Flood Insurance Program, and the NFIP caps coverage at $250,000. For a million-dollar home, that is a massive gap, and it hit slab-on-grade homes especially hard this year. He breaks down the options for getting enough flood coverage. Listen to that section.
Jake says boat owners get pushed toward the cheapest policy to satisfy loan requirements, and that leaves real gaps. The two he flags are coverage for the Bahamas and for nighttime navigation — neither is in a base policy. My own old policy had both holes, and Jake and Landon fixed it fast. If you take a boat to the Bahamas or run at night, this is the section to hear. Press play in the audio player above.
Listen to the full conversation: Apple Podcasts · Spotify · or press play in the audio player on this page.
The day after talking to Jake, the word that stuck with me was resilience. The houses that survived were the ones built or fortified to do it. The boat policies that held up were the ones with the right coverage added. None of it is luck.
The other takeaway is to actually look at your policy before you need it. I thought I was covered until Jake showed me I was not. Whether it is flood limits on your home or Bahamas coverage on your boat, the time to find the gap is now, not after the storm.
Press play in the audio player on this page, or grab Episode 942 on Apple Podcasts or Spotify.
The Tom Rowland Podcast brings you long-form conversations with the most accomplished anglers, hunters, conservationists, and outdoor professionals in the game. Listen to every full-length Tom Rowland Podcast interview.
Jake Holehouse is an insurance expert with HH Insurance specializing in Florida home and boat insurance. He helps homeowners and boat owners understand how building codes, flood coverage through the National Flood Insurance Program, and policy fortification affect both their protection and their rates, and he is known for finding and closing the coverage gaps — like Bahamas and nighttime-navigation boat coverage — that most people never realize they have.
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