Insurance, Development Risk & The Hidden Economics Of Real Estate With Lisa Holt – RFP 90 Transcript
Lisa Holt (00:00): What I’ve always found very funny about our industry is that because it’s one of the oldest industries in the world, we’ve had hundreds of years of bad processes and antiquated systems just adding on to what we do. So you have this Jenga tower of room for disruption.
Gordon Lamphere (00:29): Hi, I’m Gordon Lamphere, and welcome to The Real Finds Podcast, where we have real conversations with key entrepreneurs, activists, and researchers who are shaping the real estate industry and, as a result, our world. On today’s podcast, we have Lisa Holt from Ivy Risk. She gives us deep insight into the world of real estate development insurance. Today we discuss tips and tricks for lowering your insurance costs, the growth of AI in the insurance industry, and what developers need to watch out for going into 2027. If you’re a real estate developer or investor, today’s podcast is well worth a listen. So, why real estate? Why insurance?
Why Insurance, and Why Real Estate
Lisa Holt (01:15): I didn’t know the why for insurance when I started out in it, and I found the why for real estate afterward. But in short, insurance has fit my character profile so well. It’s just a playground for curiosity. There’s no end to what you can do in insurance. Pick any industry. That’s what I tell my kids, and what I tell people who might be looking at a career change or starting out in their careers: insurance lets you pick and choose the areas you find most interesting.
For me, I naturally gravitated toward real estate and development. The idea of something with so much longevity, really creating the world we live in from a development perspective, and the responsibility that comes with it, I think is incredible. On top of that, I get to see what it takes, the tenacity and resilience, to make things happen in the real estate world. Just closing on a deal, a transaction, an acquisition, a development could be a decade-plus in the making. I find it incredible that you’re working with people who have that long-term vision.
A Brokerage Built Only for Owners and Developers
Gordon Lamphere (02:35): Your niche is somewhat unique in the insurance world. Insurance is a pretty broad industry. I have friends doing maritime insurance who are worried about the Strait of Hormuz right now, and friends who insure agriculture and all sorts of other things. What is your niche in the insurance business, and how do you help folks in the real estate world?
Lisa Holt (03:07): You brought that up because insurance is such a big world. I’ve used this analogy a few times, and I’m still perfecting it, but think of a Christmas tree. The star on top is insurance. As you move down, you have commercial, personal lines, health and wellness, and benefits. Keep going down, and I’ll veer into the commercial space, which is where I play. There are different industry classes and different product lines. Where I’m specific, and specializing, is real estate development.
What’s unique about it is that when I started my brokerage, I made a decision, and I remember putting so much thought into it. I felt it was a very important, critical decision and a differentiator to say, “We’re not going to do any other type of risk.” I don’t know any other brokerage that does what we do, in the sense that we only write commercial real estate owners and developers. We have certain minimums, based on either the construction value of the development or the portfolio value. But overall, that’s the decision I made, because I think it requires a certain dedication and exclusivity to this type of risk to be the best, and that was something I didn’t want to stop until we achieved.
Gordon Lamphere (04:31): What makes development risk unique versus any other kind of commercial real estate risk?
Lisa Holt (04:39): What I love about development risk is that you’re selling something that isn’t there. You’re selling an idea, and there are so many factors. If I bring an actual, permanent building to a carrier, I can say, “Go see it for yourself. Go touch the walls.” There are appraisals, and there’s a lot I can provide. With a development risk, I’m selling a promise that it’s going to get done.
Take a condo development. I usually love to get my developers to purchase escrow deposit bonds, which let them use buyer deposits toward the cost of construction. In that sense, it’s a credit risk. The carriers want to make sure these developments get done, or else they’re really losing out. That product line is a lot safer and has a lower loss history, but when there is a loss, it’s catastrophic.
Then on the builder’s risk side, which is your property, there are so many variables that people don’t think about. I once had a very large project where we essentially had to draw a halo around the property, because equipment and product being stored off site was within a thousand feet of the location but not actually on the location being insured. Those are all the dynamics that matter in getting underwriters to understand what they’re looking at, telling the story in a way that minimizes their concerns, and representing your clients in the best light.
Where Insurance Rates Are Headed
Gordon Lamphere (06:24): One thing my clients have been talking to me about a tremendous amount over the last five years is insurance rates. I know a lot of our listeners have the same gripe: “My insurance is skyrocketing, and it’s compressing my ROI.” What are you seeing in terms of insurance rate trajectories as we get into 2026 and look ahead to 2027?
Lisa Holt (06:58): Insurance rates have been a spectacular topic over the last five years, and not for the right reasons. I’m in my twelfth year in this industry. I started during a very soft property market, and liability was following, so it was very easy to jump right in and compete, and I learned in that environment. Then the markets started to turn, and all of a sudden I had to take all that experience and get creative. That’s what really separates the more sophisticated brokers from the ones checking boxes or just filling out paperwork. So it was a perfect progression for my learning style.
What I’ve learned about the past 50 years or so is that it really does tend to follow market conditions. It’s a supply-and-demand product. You can’t determine exactly what it will look like, but you can follow certain trends, and it’s cyclical. These last five years were the first time that I’ve seen, and I think anyone alive in this business has seen, such a drastic shift in such a short, compressed time frame. That’s what’s been crazy.
As I was thinking about our podcast leading up to today, I had a little chuckle to myself that the insurance market almost feels like it has followed our political landscape. Everything’s kind of crazy right now. It’s interesting to watch the insurance market do things that haven’t happened in the past. And, who knows about correlation versus causation, but there is a connection to where climate change has taken us. Take convective storms, for example.
Lisa Holt (09:12): Their cost was about 30% lower ten years ago, and now there’s a new normal for the average cost of convective storms. That’s something we didn’t even discuss ten years ago. Wildfire used to account for 1% of total global losses, and now it accounts for 7%. There are so many shifts and changes, and people don’t realize it has to do with the entire global landscape, not just what’s happening in their backyard. I understand that causes a lot of pain, because people say, “I get the increase, but it has nothing to do with me or my risk,” and that can be incredibly frustrating. That’s where insurance buyers need to take control of their program, so they’re not reactive to the markets but proactive, and they stay in the driver’s seat.
Asset Classes and What Underwriters Look For
Gordon Lamphere (10:11): One of the few things we can control is what risks we take on. What risk profiles are you seeing across asset classes? Are there asset classes that haven’t seen spikes, or where things are leveling off faster? And are there asset classes, for developers or owners, that our listeners should be particularly concerned about?
Lisa Holt (10:44): It’s funny. I recently heard someone give a brief intro on insurance, and one comment was that with general liability, they’re really concerned about foot traffic, so try not to buy retail properties. I felt that was such a simplistic version of what’s really happening. I would never say to stay away from certain asset classes, because there are so many other things that go into it.
But from an insurance perspective, if I had my pick, multifamily has had the most challenges. It’s been hit the hardest, unfortunately, especially on the development side. That’s the nature of that risk: you have a lot of different tenants, a lot of foot traffic, and the liability can be pretty great. Overall, carriers and underwriters look at tenant profile, occupancy type, and construction type.
If I had to name the single most important part of your role as an insurance buyer, it’s to select a broker you trust, and then be very transparent and provide as much information as possible. It’s up to that broker to analyze and digest the information in the way that’s most palatable for the carrier and underwriter, and to understand what they’ll be looking for and what’s important in what the client is providing. I’ve come across too many situations where clients don’t understand what’s needed or why. Once you add that education piece and explain why you’re asking for what you need, it changes the entire process.
Data, Modeling, and Lender Requirements
Gordon Lamphere (12:40): How are brokers, and as a result underwriters, underwriting today? There’s more data than ever. What are they generally looking for, and how has the process changed for a user, developer, or owner who has worked with insurance in the past? It seems like there are a lot of additional requirements and things being looked at on the insurance side, even compared to ten years ago.
Lisa Holt (13:17): Absolutely. Data and analytics have become a major part of what we do. I strongly believe that if you have the right broker involved at the very beginning of whatever process, whether it’s a development or due diligence on a potential acquisition, there’s so much value we can provide with the data and analytics we have available.
Typically, when you go to get a policy or a quote, the carrier has its own modeling, and that’s notoriously a black box. We don’t get to see it. They just spit some information back to us, and case closed. So we’re taking that power back as brokers. I’ve formed partnerships with much larger national and global agencies as well, because the data is key. We’re coming in early, including on the lender requirement side, to help educate lenders about what they’re looking for and asking for, and help shape what those requirements should look like so everyone is protected.
It’s also been interesting on the carrier side. When you provide this information, it changes what we used to see as a historical look at insurance. We’d say, “We’ve had X hurricanes and this many catastrophic losses over the years, so going forward, one plus one equals two.” Now there are forecasting models that let you run so many different scenarios and identify critical points at specific locations. Say you have a large portfolio. We can do a very specific dive that says, “If you make these capital improvements at your locations in these zip codes, and you do some water mitigation in the residential units at this location, these are the returns we could be looking at.” Or, “These are the requirements we can discuss with the lenders about minimizing, lowering, or doing away with entirely.” It’s a very strategic process that
Lisa Holt (15:39): can be so involved that it really makes you feel like, “Okay, now I’m actually paying for something that makes sense.” You’re so educated about what it looks like and why you’re spending the dollars you’re spending that it becomes a much less frustrating process. What I like to say is, sometimes pleasant.
Getting the Most From Risk Improvements
Gordon Lamphere (16:06): It’d be wonderful to have improving a property be a pleasant process, but it definitely costs money, and a lot of people listening want to make changes and get the most bang for their buck. Where do you see the biggest gains for people who want to improve a property to limit risk and reduce liability?
Lisa Holt (16:43): I think the first thing is the mindset about what the process will look like. It’s a long-term play. Nothing is going to happen from one renewal to the next. Depending on where your current insurance program is, there are a lot of programs I take over that I’m able to drastically improve, whether through premium savings or enhanced coverage, terms, and conditions. But if you’re already in a good place, it might be more difficult to improve, unless you’re changing the entire structure of the program or taking on more risk.
So we usually start with: what’s your risk appetite? At my house, I have a huge tolerance for risk, and my husband likes to buy as much insurance as possible. There are different buyers out there, so first you understand what they’re looking for and what they’re comfortable with. Then, how much do they want to understand about the process? I like to give small, medium, and large versions. Some clients want to dive in and know every aspect, and some say, “I’m going to put this in your hands. I need the highlights to make the best business decisions internally.”
If you decide to do it right, you’ll find the results, and you get to pick between savings and enhanced coverage. On one account I’m working on right now, I can produce a ton of savings, but they also have a lot of exposed buildings and locations without coverage. So we’ll analyze that and give them options that let them say, “I’m going to enhance coverage right now.” My recommendation at this moment, because of where the property market is, is to buy more, because that is going to change. Property rates have come down so quickly and so drastically that this is the time to do it. Then, when the market starts to shift again, which it will, you have things you can let go of. You can say to your carrier,
Lisa Holt (19:05): “Okay, fine. I’ll give you a certain limit here, or I’ll raise this deductible there.” Those are things you want to keep in your pocket and be ready with. So again, it’s a long-term outlook: “I’m going to dedicate myself to this risk management program, look at it in roughly five-year cycles, and give it the attention it deserves, so nothing falls through the cracks and I’m not caught by surprise,” which, unfortunately, is what’s happening to the majority of buyers right now.
Why Property Rates Are Falling Now
Gordon Lamphere (19:38): It’s interesting to hear you mention rates coming down. For the last five or even ten years, all I’ve heard from our users is that rates are going up, up, up, and in some cases it’s borderline panic. Where are you seeing rates come down, and why?
Lisa Holt (20:01): That’s a great distinction. Each product line does its own thing. Carriers have different risk appetites and pick different areas to focus on. It’s like gambling. I love this analogy because I like blackjack. You might be a poker player. I might have a lot of wins one night and you might not do so well, and then the next day the luck turns. It can be the same over a policy term. If you’re AIG and I’m Chubb, and I love residential and I’m the leading player in personal lines, while you’re doing a lot in the environmental space and finding traction there, neither of us is right or wrong. But depending on how those areas perform, we might not end up in the same place at the end of the year.
So it’s important to look at your risk management program as a whole. When people say, “My insurance is going up,” I want to ask, “Which parts? Where?” Auto has been difficult since I’ve been in the business. That’s a trend that hasn’t given any relief. Then there’s geography. I live in South Florida. In the Midwest, you haven’t had as many natural catastrophes, but as I mentioned, convective storms have increased. So risks change, and they’re specific to geography and asset class.
Property is usually the driver for a lot of insurance buyers, and I suspect that’s what you’ve been hearing so much about. We had a lot of softening through 2019. Then it started to harden, and from probably 2021
Lisa Holt (22:24): to 2023, it was a bloodbath. People had to go back and renegotiate contracts, because buying the insurance they were required to carry would literally have put them out of business. I’ve heard stories from 30 or 40 years ago where people couldn’t even find coverage, let alone at a higher cost, so there have been worse times. But when clients get 100% or 200% increases on their property alone, that can destroy a business very quickly.
We went from that to steep decreases. We’re probably still looking at double-digit decreases going into 2026. What I love to explain about insurance is that the flow of capital really dictates, in many ways, how strong the property insurance market is. Money is coming in from all sides of capital investment, and what’s grown over the last few years is insurance-linked securities. Those are financial instruments that let insurance companies transfer risk to capital market investors. They’ll offer a cat bond, and you can buy it, and they can be very specific.
These hedge funds get to diversify their risk. They can say, “I’m going to bet that South Florida,” and we’re back to gambling, “won’t have any hurricanes for the next 12 months.” The returns on those cat bonds can be very high. Because that type of investment has become so big, it’s added a lot of capital to the reinsurance marketplace, which flows down to the guaranteed cost carriers most people buy from, and the savings keep trickling down. It’s for reasons people aren’t really thinking about. When you step back and look at the whole world insurance encompasses, and how it’s layered into the fabric of everything we do, you start thinking from a place of curiosity: “That stinks that my premiums went up by that much, but it’s pretty cool to think about why.”
Captives and Alternative Risk
Gordon Lamphere (24:22): Speaking of bets, are there solid bets we can make as developers, users, or investors, creative ways to structure things and limit risk on our end?
Lisa Holt (24:48): In the same way you identified that different product lines see different pricing pressures, it’s the same with the type of risk or the type of buyer. You might have a smaller-market insurance buyer with a smaller general liability or property policy, maybe without a big portfolio. In those cases, you’re placed in a limited set of options, so again it comes back to finding a broker you really trust.
But with larger, middle- to large-market real estate owners, investors, and developers, the options are endless. The creativity and innovation out there keep growing. We’re looking at alternative risk. That’s my favorite space. It’s about how we can deploy capital with an alternative risk financing strategy, where we say, “We’re going to put money into this and watch it grow. We’ll manage our safety and risk management programs so we don’t have a lot of losses,” because there are ways you can take control of that too, “and the money comes back to us.”
What I’m describing is essentially a captive. That’s when companies have the scale or capital to say, “I don’t need you, Mr. or Mrs. Insurance Company. I’m going to form my own and take on the risk. I’ve had excellent losses for the past five-plus years, and I feel comfortable that this is a gamble I’m ready to take on myself.” When that happens, the success stories are incredible. I have clients who get annual dividend checks of six figures plus, and it’s always really exciting.
Gordon Lamphere (26:55): What kind of client fits the profile for that kind of structure?
Lisa Holt (27:06): You want someone who’s dedicated to their risk management program. Implementing something like this can be more tedious on the front end. They need to be liquid or have access to capital. They can put up letters of credit, because if you think about it, you’re building a bank that essentially insures your insurance company. There are options to get reinsurance as a backstop for severity-type claims, versus frequency.
Essentially, you want enough premium spend. We have a saying in the captive world: if you’ve seen one captive, you’ve seen one captive, because they can be structured so differently. At the larger scale, you’ll have a single-parent captive. But there are options for smaller companies, like group captives, where you combine your risk with other members. That way you spread out the cost of implementing the captive, and you’re really just joining one that already exists. So it’s not only for people with a lot of insurance spend. But if I had to throw out one number, we usually like to start at around two and a half to three million in total cost of risk. That sounds like a lot, but it takes into account everything spent on insurance, whether it’s a deductible or a claim they had to pay out. It really encompasses everything, because a captive lets you manage so many areas that the guaranteed cost policy we usually buy does not.
Geography: The Riskiest Places to Insure
Gordon Lamphere (28:56): A lot of the risk discussion now centers on geography. We’ve touched on climate change and hurricane risk. Are there geographic and asset class arbitrages you’re seeing, with the insurance industry viewing certain regions as more or less risky? What would you say is the riskiest area in the United States right now, and maybe we could discuss the least risky as well?
Lisa Holt (29:44): I’m probably sitting in the riskiest one from an insurance perspective. Florida is surrounded by three bodies of water. We stick right out into the Atlantic, and there’s a lot of flat land, so hurricanes and windstorms are very prevalent. Anyone buying insurance in Florida, especially South Florida, automatically pays at least twenty-five percent more. That’s just a done deal, and that’s in terms of auto. Carriers are very aware of the differences in geography. The auto rates we have to pay down here, both commercial and personal, are astronomical, and if you drive on our roads, you’ll immediately understand why. You don’t need to explain that one.
What Real Estate Isn’t Talking About
Gordon Lamphere (30:43): My brother has lived in Miami for a very long time, and I remember him telling me not to use your turn signal too early. In the Midwest, that’s not something we ever worry about. One thing we do worry about on the podcast is what we might be missing. We try to speak to the men and women in the arena to get in-depth knowledge outside our immediate realm. What’s one topic regarding insurance that the real estate industry isn’t talking about enough? I think real estate in general is missing a lot when it comes to insurance.
Lisa Holt (31:46): Yes. That might also have something to do with the fact that, well, we’re actually very unpopular at the moment and have been, but before this recent cycle, we weren’t even thought of. So the real estate industry has a lot to catch up on. If I had to pick just a few things your listeners could take away from someone who does this every day, there’s so much they can do from the very beginning.
One thing I’ve noticed: when you want to make capital improvements or develop something, what do you do? You bid the work. That’s the nature of the process. But that’s not the case in insurance. So the number one thing is to pick the right broker and say, “This is the person I want handling my risk management program.” Then, as I mentioned, give as much information as possible. That will only help your case, assuming you have the right broker who knows what to do with it.
If you’re active in acquiring or selling properties, keep in mind that we look at the program holistically. If you have different construction types or buildings of different ages, newer properties can often help offset some of the older buildings and less favorable risks. It really varies, but it’s something to keep in mind right off the bat. And if you’re touring properties and see that one is dilapidated with a lot of room for improvement, you can automatically tell yourself, “Insurance isn’t going to be pretty on this.” That’s a pretty easy connection to make, and it’s important for people to make it as they look at opportunities and ask whether they make sense for their business.
AI and the Future of Insurance
Gordon Lamphere (34:06): We’ve been on tours recently of a number of portfolios where people are reevaluating their management or looking to sell. At one of them, they were ranting about how high their insurance rates were, and I’m driving around thinking, “I know why your insurance rates are so high. It’s because you’re poorly managing your properties.” There are plenty of things like that you can easily tell. On our end, things are moving toward a more hands-on management style to reduce things like insurance rates, and the world is so data driven. Where do you see insurance going ten years down the road, and how can the end user react to it?
Lisa Holt (35:11): It’s such a loaded question, because my immediate response is that I’m terrified. But then I sit back and think, no, it’s really just the unknown. We’re going back to the AI conversation, and AI is an ongoing topic for a reason. What I’ve always found very funny about our industry is that because it’s one of the oldest industries in the world, we’ve had hundreds of years of bad processes and antiquated systems just adding on to what we do. So you have this Jenga tower of room for disruption. I’m very excited about that. But when you’re in an industry where, everywhere you turn, there’s somewhere you can make drastic improvements and changes,
Lisa Holt (36:10): it makes you worry. I can’t say it’ll be in the next 10 years, but I think the way we do things is going to become obsolete. I don’t know how we can continue with the antiquated processes we use now. Even today, when we hang up, I’ll go back to a manual spreadsheet analyzing a risk, and I know there are systems out there that can already do what I need. It’s just a matter of how long it takes them to become user friendly, where that takes us, and what impact it has on our roles as insurance brokers and on insurance carriers.
I just finished a demo of an AI system coming out of Lloyd’s Lab in London. For insurance carriers, it can analyze and connect all of their different policy language, so they can say, “We’re seeing a series of losses in this specific geography, asset class, or type of loss. Let’s analyze where we have that exposure in our policy language and figure out how to close that gap.” When I hear something like that, one part of my brain thinks, great, carriers can get tighter on their requirements, which means they can manage risk better, which hopefully means better rates and savings. But it also tells me that if they can identify every area that exposes them, then it’s the buyers who are being closed out of the opportunity to recover on a loss.
Gordon Lamphere (37:58): I think it goes to this, and it’s something we see consistently now. We have two members of our team who use Claude and ChatGPT every day, and we’re developing all sorts of new algorithms and programs. Maybe sixty percent is managing properties, and the other forty percent is improving how we evaluate properties on a variety of factors. But what I think people underestimate, in the world Elon Musk and Peter Thiel often describe with AI, is that it assumes you have all the data. I still think there will be huge gaps. AI isn’t God. So you’ll see gaps in the market, and there will always be arbitrage for somebody who walks the site and fully understands the ins and outs of a property. But I think margins will get a lot tighter, particularly for the consumer, based on everybody we’ve been talking to.
Lisa Holt (39:08): I just heard a statistic on that note, and it goes hand in hand with what you’re saying. There are these systems and tools that can now be deployed that create savings, but there are also people who no longer have jobs because of them. So it’ll be interesting to see where that goes.
The Final Four
Gordon Lamphere (39:31): It will be really interesting. One thing we find particularly interesting is that we have a number of younger listeners on the podcast. What advice would you give a young Lisa just starting out in the industry, if you could sit down with her for one minute?
Lisa Holt (39:54): I love this question. Of course, I thought through so many critical pieces of information I could give young Lisa, or any young person out there. The number one thing I keep going back to is that the majority of people don’t know sh*t. They don’t know sh*t about sh*t. Am I allowed to say that?
Gordon Lamphere (40:19): Yes, yes.
Lisa Holt: It’s incredible. I’ve lived my life with such high expectations of myself that it almost created a loop of thinking that maybe other people know something I don’t. Ninety-eight percent of the time they don’t, but they’ll speak as if they do. I found that very interesting. So my number one thing is: don’t let that affect your own thinking. However strongly, or with however much conviction, someone says something shouldn’t influence how you interpret it. It’s about the words, understanding what’s really being said, and having the confidence that, as a younger person, you’re just as smart as the veteran with thirty years in the industry. The only thing you’re lacking is experience, which is going to come. There’s so much value in the younger generations coming in, and I love to see what they’re going to do with this and what we can learn, because it’s a two-way street.
Gordon Lamphere (41:30): You’ve got to have faith and trust yourself. One thing we do trust is that you hopefully have someone we should reach out to. We find that the men and women in the arena truly know the best voices to talk to in the industry, and one of the whole reasons for the podcast is to get connected with those folks. So who’s the next person we should have on the podcast?
Lisa Holt (41:59): I gave this a lot of thought as well. I don’t know if she does podcasts, but when I talk about alternative risk and captives, one of the largest captive managers in the world was built by a woman who is nearing retirement, and she’s an amazing woman. Her name is Jennifer Gallagher. It’s incredible what she’s done and where she’s taken this area of the industry. I’d love to reach out to her and see if she’d be interested. The more I can communicate to insurance buyers that there’s another way to do it, where it’s not just a sunk cost and you’re actually leveraging your risk as an asset, the better. It’s a game changer. Jenny Gallagher has been with Artex, and she’s been incredible. And for any woman in insurance: the first female insurance broker didn’t come along until 1973. It’s pretty cool to see how far it’s come.
Gordon Lamphere (43:18): Wild. We would love the connection to Jenny. Our last question today: if somebody wants to connect with you, what’s the best way to get in contact?
Lisa Holt (43:35): The easiest way is my Instagram, @IvyRiskOfficial, my website, ivyrisk.com, that’s I-V-Y-R-I-S-K, or my email, [email protected].
Gordon Lamphere (43:52): Lisa, thank you so much for hopping on the podcast today, and we’ll have to have you on in the future.
Lisa Holt (43:56): I’d love that. Thank you so much, Gordon.
Gordon Lamphere (43:59): Thanks again to Lisa. We appreciate her insights. If you enjoyed the podcast, please give us a like, a five-star rating, and a review. Your comments, interactions, and subscriptions truly matter and help us continue to bring on quality guests. You can find us on YouTube, Spotify, or wherever you get your podcasts. I’m Gordon Lamphere with The Real Finds Podcast. Thank you for listening.
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