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Transcript

Ben Markland: [00:00:00] Hey everyone, thanks for joining us for another episode of the Insurance Leadership Podcast. My guest today is Dylan DiMarchi, and he is the co-founder and CEO of Eventual. And this is a company that they have a product called Premium Lock we're gonna talk about a little bit today. Little different than our normal guests, so Dylan is more on the property casualty side. He deals with home insurance. I think it's very interesting. It's a new company. He is a Yale graduate. I read a little bit about you, Dylan. I know you're a sailor, and I think it's gonna be very interesting to see how you kinda took the winds and the weather and translated that into what eventually becomes a business of insuring houses. So I think that's very interesting. I will note he's also, prior to this, was an investment professional at Blackstone and did a lot of real estate commercial real estate investing. So I think there's a lot he can kinda bring to the table on the [00:01:00] leadership side. And Dylan, we just wanna chat with you a little bit about your company and what you're doing. Start off tell me a little bit about sailing and how that kinda got you to where you are right now.

Dylan DiMarchi: Yeah. First, Ben, thanks so much for having me. Really excited to be here and share to all of your listeners and viewers the craziness that's been going on in the American home insurance market. It has been a hectic ride over the last five years, and super excited about Premium Lock and Eventual what we're building here. But yeah, sailing, I could talk all day about sailing, so don't get me too tempted. But yeah, sailing's this kinda niche, awesome sport. I grew up in Hawaii. If you're gonna grow up there, you're either going to be a surfer or a sailor, and I chose the latter. I like it as a sport 'cause you don't have to do too much work. You sit there, the sail moves the boat, and trim the sheets and steer a little bit

Ben Markland: I've done it once and it wasn't as easy as you make it sound. I was not doing the right ropes and the whole tipping over thing was really.

Dylan DiMarchi: It's definitely like a kinda not much cardiovascular output, but definitely kinda fine-tuned- motor skill, keeping the boat balanced and predicting things. But, as I have seen in Hawaii growing up [00:02:00] there, and then, spending my life on the East Coast and now opening up our office in Los Angeles here recently, I've definitely seen the relationship between how weather events and loss events that are driven by that weather impact the price of home insurance and home insurance dynamics. Out here in Los Angeles we had tragic, huge severity wildfires in early 2025. And, I think you can start to see how over the long term, some of these changing wind patterns and temperatures and other sorts of things, wind hail convective storms definitely are impacting homeowners across America through this kinda niche corner of their life, which is the price of American home insurance has gone up dramatically really since COVID over the last five or six years.

Ben Markland: So we're here in Mississippi, and Mississippi, our devil is hail, and I've experienced it myself, so I had a hail claim. There was a storm, I believe it was probably about five years ago. The challenge for an insurance company is when hail hits, it's not one house, it's every single house that got you there. And of course, it [00:03:00] wasn't immediate, but two years later, the rates just absolutely skyrocketed. And you really have no choice because every insurance carrier that owned a roof in this area is affected the same. So you can't really go jump around and say, "I'm gonna shop this," because they all experience the same loss.

And-

Dylan DiMarchi: Exactly.

Ben Markland: I think that you can probably speak to that, 'cause that is what I understand it's a little bit of what you're doing, is trying to take some of that uncertainty out of the pricing, right?

Dylan DiMarchi: Yeah, Ben, that's exactly right. Whether it's wind, hail, hurricane wildfire, theft, winter freeze, all of those are driving the cost of home insurance to increase. There's no free lunch, so when you have hail damage, you and all of your neighbors- probably are having some conversations with roofers who are like, "Oh, you're gonna get a free roof. Your carrier's gonna give this away for free." And because there is no free lunch, ultimately that sort of activity that we've seen where there's been like, a ton of hail-driven roofing claims over the last few years, that has driven the price of [00:04:00] insurance to grow. And so stepping back, I observed that as a commercial real estate investor at Blackstone, which primarily owns, Sunbelt rental housing, and we saw the price of insurance do the exact same thing. Summer of '22, summer of '23, we just saw premiums, go up dramatically, not just in our portfolio, but in all housing. And I as an insurance outsider at that point in my life, stepped back and asked myself, "Why are we as homeowners, to focus on the personal lines, facing these rate hikes every year when we commit to our homes for not one year, but for eight years, pre-COVID, and now 10 or 12 years post-COVID? Really a long-term commitment to our assets." America has these amazing, magical fixed rate long-term mortgages. 15-year, 30-year fixed rate mortgages where you know exactly what it's going to cost to run and own that home from a debt perspective, and yet we're waking up every single year with these seemingly kind of random rate hikes where your neighbors [00:05:00] maybe had a big claim. Now the carrier thinks that the probability of, hail damage in your geography is high, and so your rate goes up, your coverage A goes up, and you wake up, as most Americans have, paying 50% to 100% more for home insurance today than they did in, 2019 or 2020. And so what we at Eventual have built to tackle that unpredictability, that uncertainty over the long term is we said, "Wouldn't it be nice to have a long-term home insurance policy?" So rather than a one-year policy, what if we knew or got closer to knowing what it would cost to insure my home for the next three years? And so while that's totally not a new idea, Cincinnati's had this in commercial, Erie has this in personal lines auto with a rate lock product. Japan looking outside the U.S. Has had multi-year dwelling fire, I think, for most of Japan's history. We said, "Let's add a supplement to empower independent agents to keep selling the admitted lines standard home insurance [00:06:00] policies, with their Safecos and the Travelers, those carriers that they and their customers know and trust, but let's add a supplement that gets that one-year policy to be a little bit more predictable for the long term," and that's exactly what we've built.

Ben Markland: So how? I'm curious, how does it work? So they're still buying the primary insurance through the Travelers or the Safeco, whatever. When and if and when they experience a rate hike is PolicyLock picking up the difference? Is that how that works or?

Dylan DiMarchi: Yep. So independent agents continue to sell home insurance as usual. The homeowner keeps paying for their home insurance as usual. Most of us have loans on our homes, so we pay for insurance through escrow. Premium lock then is sold by the agent to the homeowner. There's a little bit of an extra monthly or annual fee, and then we set this payout threshold. And so if at any point that customer's premiums exceed this threshold or get too expensive, we reimburse the customer directly for any of that overage. And so if the premiums get too expensive, we take a loss, and we reimburse the customer. And so just like that, our average customer is paying us [00:07:00] 18 bucks a month, so it's quite affordable. And now they get predictability and peace of mind that they know exactly how much their insurance will cost over the next three years, and they don't have to wake up stressed at renewal and call their agent and re-shop and do all this kind of effort. They just get that peace of mind for the long term.

Ben Markland: I think it's a very unique product. I think there's obviously a need for it. How are you guys underwriting this? Is this something, is it geographical? Are you looking at, weather patterns? I know that's what you spoke a little bit to the winds in Hawaii and whatnot, but I'm thinking back to the last big wildfire event in California, and don't get me wrong, some of this is coming through the news mill and the social media, but, my understanding was there were tens of thousands of homeowner policies canceled by insurance carriers prior to that because whatever data they had put them to such a high risk and I think there was something due to rerouting of water resources off of the Hollywood Hills, and policies were canceled. [00:08:00] And what do you know? It, a few months later the whole place is on fire. And that makes me look, it's like, man, these insurance companies, just like we do on the health and life side, they're using big data to their advantage to make decisions on what they're gonna insure or what the price of it's gonna be. And we almost joke about it, but look, if your homeowners is canceling your policy, you might wanna get out of that house sometime soon 'cause something's coming, right? So I guess I'm curious, long story short, what data are you looking at to kinda price this thing and be able to not get killed if a whole area's rates go through the roof? Obviously, you guys picking up the difference. There's a risk that's gonna land on you for that, right?

Dylan DiMarchi: Definitely have a lot of comments about California specifically. California is a unique beast as any of your listeners who may sell home insurance or be, home insureds. As they may know, California definitely has faced much more than its fair share of regulatory and pricing dynamics that we can get to in a minute. But in the meantime, yeah, our [00:09:00] approach at Eventual to to creating Premium Lock is that our job is to predict where carriers are going to set the price of insurance at a specific address for the next three years. That is a really hard job. There are many inputs that we consider. Of course, the data sources on which we rely to underwrite this are of the utmost importance. So first when we were starting the business, we relied pretty heavily on some historical data at the property level that comprised, tens of millions of US homes over, more than a decade of historical, seeing pretty good property-level metrics of, location price of insurance, rate online versus, coverage A growth what sorts of risk retention that customer's holding, when these policies start and end, and, who is the insurer. Over time, we've transitioned into being buyers of pretty much all the data that can help make our product as affordable as possible for homeowners while still giving us the right to be very accurate and predict this price growth correctly. And so rate filings are a big one. Rather than looking historically, you can look at rate filings to [00:10:00] see where, overwhelmingly carriers are reporting that not for three years they're gonna set prices, but, in the near term, maybe you'll get the first renewal or so. So that's super helpful. We then put a lot of those data, as well as a bunch of other data sources happens to be a machine learning approach. We have a physics PhD, we have someone with kind of an options background to help figure out exactly these predictions. And so by order of importance inflation overall is a massive driver. The labor and the sticks and the bricks of rebuilding your home goes up over time, as it tends to, much faster than just broad kinda CPI, just broad inflation that tends to mean that carriers just recommend and force you to buy more insurance, which makes your insurance more expensive. So inflation is by far the big driver. Rates, interest rates. What is the cost of capital? If you're a reinsurance company, what do you need to pay your investors? If you're an insurance company, what do your investors expect as a return? That tends to follow inflation pretty quickly. Summer of 2022, we saw the war in Ukraine happen, and then we saw a boat get stuck [00:11:00] in a canal, and then we saw the price of energy go up, and then all of a sudden you wake up and the price of insurance has skyrocketed, only a few months thereafter. Frankly, today we're seeing a lot of similar sort of dynamics with wars that are happening right now. And so there's a lot of uncertainty about how the price of energy can impact the price of insurance, which was a real surprise to me, having been an insurance outsid-outsider a long time ago.

We also look, of course, at weather events. Carrier profitability is a huge driver. So unprofitable carriers tend to have pressure from their boards and their shareholders to raise prices to become profitable. Those that are printing cash, which we've started to see a lot of homeowner carriers and auto carriers really having real profitability over the last couple quarters, they tend to face more competitive dynamics. Maybe they are not able to have so much pricing power. And then, longer term weather dynamics of, A, we're tending to see this geography has a lot of frequency or, unexpected severity of claims. Those are all related. And then to circle back to the start of this question California specifically, [00:12:00] regulations are a huge driver of a difference between where we think prices should go and maybe where prices end up. And so, the media tend to talk about Florida and California in a similar vein, but they could not be, more different insurance experiences. Today, Florida, the price of home insurance is actually barely growing. It's growing about 4% annually today as of February of 2026 so just last month. And that's because Florida was a super early mover. Even before COVID, they were starting to really grow the price of insurance very quickly. California, on the other hand, has faced similar claims pressures where carriers are really eager to raise prices because they're not selling profitable insurance. And yet, due to a lot of regulatory dynamics in the state that are complicated, the carriers have been unable to make their insurance as expensive as it should be for them to have, reasonable unit economics there. And so regulations are a huge blocker, and that leads into why insurance may be unavailable to you. At Eventual, [00:13:00] we focus deeply on insurance unaffordability, the price of insurance and the price going up, which is super closely related to insurance unavailability, which is just not getting it. But ultimately, unavailability, there should always be a reasonable price of insurance, whether you're paying 50 cents for insurance as you are in California, or 130 cents for insurance as you are in, Louisiana and some other high-risk states. And so as prices of insurance grow in California, we're hopeful because that will lead to greater insurance availability, and at least you can get insurance and get a mortgage and, transact a home as you would hope so. It's painful for consumers, for sure, to face these big rate hikes, but ultimately, having expensive insurance is better than not having any insurance at all.

Ben Markland: That's right. Do you think the insurance carriers have a focus? 'Cause it sounds like what you're saying is they're not even-- in some places they're not even making money. So the focus of them being more competitive or lowering rates or relieving any pressure from the homeowner, it's not even on their [00:14:00] radar. Which is good for you because, that's what your product is addressing, obviously. But do you see there being any pressure or any outlier in the home insurance world that's gonna bring some of this down? Or you think it's status quo and we're just gonna keep on going up.

Dylan DiMarchi: Yeah. Generally, our expectation-- This is our job at Eventual- is to have views of where insurance prices are growing. Today, insurance prices are growing, eleven or twelve percent nationally across the US for admitted lines home insurance. Our view is that, through twenty twenty-six they'll go down to kinda very low double-digit percent. So it will still grow very quickly, three to four times faster than inflation. And then in twenty twenty-seven, we hope to see prices growing kind of the high single-digit percent year over year. There is hope, but our view is not that growth is going to totally reverse and that prices will net come down across the country. Generally what the carriers are thinking about is it's a pretty hard life as a carrier. You are selling what is a pretty [00:15:00] regulated form that's pretty homogenous, pretty perfectly competitive across all of your competitors. It's a very similar piece of paper, and you are competing for market share. And so your customers, your homeowners, generally, other than, when you have a really good brand, that you spend your billions of dollars on TV ads talking about your Emus and your Jakes and your Flows and all, all these other people. Aside from branding power, you tend to just compete on price. And so you tend to wake up, as you see in Florida, with a dozen new carriers seeing the prices are really high, coming in, trying to gain market share, lower price, and then, those carriers may have very hard years in subsequent years when they wake up and realize that, oh, there is a correct price for insurance, and maybe by pricing too low you got it wrong. So ultimately, it's those competitive dynamics that, that run the world of home insurance. And so as a result of that- over the long term, home insurance is not a hugely profitable line of business. You can walk away with single digit cents of margin. But ultimately, there's a lot of competition and you're selling a similar product. And that dynamic is what makes our business possible, [00:16:00] is that competitive dynamics mean that the price of insurance should always remain pretty competitive and relatively low margin. But I will add that, today, especially some of these public carriers where you get really good data on what's happening, they've had real pricing power for the last few years, and so they're really starting to print cash. Some of them are really proactively dividending that back to the policyholders so that they're not gonna get extra regulated and see prices start to be forced down. They're proactively doing that. So lots of complicated dynamics happening behind the scenes there.

Ben Markland: Yeah. I think there's two ways to keep money in your pocket. You charge more or you pay out less, right? And I think the dark spot over property and casualty carriers is when it comes time and you don't get paid, right? Or you don't get paid what you need and, or, a claim, they fight you on a claim. And actually, I'll use Mississippi as another example. I have some friends that are agents and this is just whispers, but they said they've heard rumors of a roof potentially becoming a rider as a separate charge from your insurance. And I [00:17:00] get it. It makes sense if the data points to that, hey, the roof is the most common thing replaced, and we can't just put that in the bucket with everything else. But that's the kind of thing that I think ultimately rubs the consumer the wrong way is, "Look, hey, I've paid these prices. I haven't complained about it, and my house flooded, and now I gotta argue with you for six months to get it fixed." So-

Dylan DiMarchi: Yeah ... super painful. Definitely, if you are a carrier and your sole job is to be there to pay out under a kinda long, complicated contract, you should probably pay out. Of course, these, these carriers are generally, businesses that have been running for a long time. And so they know how people try to get maybe claims when they shouldn't, and roofing is really at the core of the problem. There, some other companies in our space that are working specifically on these roofing issues because roofers are just. Turns out they're very good salespeople, and when they think you can get a roof that's covered by a third party they tend to go after that pretty aggressively. So roofing and litigation are certainly, some of the most important drivers of what's caused this in your geography at least, which [00:18:00] impacts potentially the price of insurance in places as far away as Hawaii and California and maybe Maine, so- it's all pretty related.

Ben Markland: Dylan, I, I appreciate all that. Let's pivot a little bit. So this is the Insurance Leadership Podcast, and I wanna touch on you a little bit as a leader. So you have founded a company. You are running a sales team, right? I know you mentioned you've probably got sales guys running around behind you in your building there.

Dylan DiMarchi: Yeah. That's right.

Ben Markland: Tell me a little bit about how your experience has been as a leader and, do you know, the, starting of this company to getting it to where you are today.

Dylan DiMarchi: Yeah. It's a lot of fun. Again I started my career working what in my view is one of the best first jobs you can have. Really hard, long days learning a ton at Blackstone, becoming doing your 10,000 hours becoming deeply proficient in a very small vertical of the world, which was real estate. I try to bring the parts of that experience that I liked into this new role for the team, and also try to, manage some of the parts of that role that were maybe a little bit suboptimal. And number one is just trying to find greatness [00:19:00] in everyone we hire. So I think I've learned a lot through how to interview and how to find greatness. References tend to be not that useful because, the, the candidate is bringing those contacts to you. And obviously, most of us are able to find one or two people who speak really highly. It's mostly about getting that candidate in front of the team and getting feedback and really putting them through real-life scenarios of how would you perform in this job and just actually doing some work together before you decide if it's a fit or not.

Overall, I think how we've structured the team is it is a super small team today. I think we're really proud of how lean we are for the number of agents and the number of customers we have. And, we've customers in more than half the US in 33 states today. And the product's available in all 50 states. So really it's just about incentivizing people as well to want to be hungry and to grow the business while growing, their role in the business as well. So ultimately, everyone in our business has ownership of the company. We've raised venture dollars from some great venture investors, and so ultimately I think you put a lot of that together and you [00:20:00] tend to build something that feels like as much of a rocket ship as kind of a new product or a new risk transfer business should be.

Ben Markland: It's fantastic. Now is your sales team going directly to the consumer, or are you guys trying to work through the Allstate agent and the Travelers. How do you get Premium Lock to the consumer?

Dylan DiMarchi: Yeah, that is the secret sauce in insurance, is how to distribute at, economics that make sense for everybody. Today, we distribute exclusively through independent insurance agents, retail agents across the US. We've got mom-and-pop agencies with, Gmails that do a great job, all the way up to some of the largest regional and national agencies that are distributing this across point of sale with new sales professionals as well as, some of their customer service reps, their account managers. I think what we have observed is that in the kinda 20-teens, you saw this huge push for direct-to-consumer, D2C distribution. I think that was the promised land for a lot of kinda InsurTech 1.0, and ultimately you see after some of these companies have gone [00:21:00] public and you start to really get detail about their operations, that the cost of finding homeowners who are excited to learn about insurance or even, a supplement like ours that's even more niche it's really expensive to get homeowners to care about that directly. There's so many dollars and companies fighting for those homeowners' eyeballs. You've got lenders with, huge margins that can spend a lot of money acquiring customers. You've got point of sale of actual home, realtors and real estate agents and others. And so ultimately, it's quite hard to win the customer directly, and all those incumbents before us have proved that. We invested pretty little energy into feeling out if homeowners wanted this directly. It seems like agents, throughout time have had, independent agents especially, have had kind of that 40, 50% market share and have been really sticky, mostly 'cause they do a great job. It is a hard job out there getting your producers to hit the phone, go get those customers, go build that referral network. And so we lean on our agents really heavily to distribute this product. Ultimately, it's a pretty thin piece of economics. Our average customer's paying us 18 bucks a month. So there's-- it's less about us [00:22:00] incentivizing our agents by paying them directly. We're not retiring any agents. I'll point that out. What we are doing though, is winning some real kinda second order, super helpful impacts for these agencies. Just like with the carriers, agencies need to do battle and to compete and to win that homeowner customer. And a lot of these agencies are selling a similar form, similar H03 or 5 with, similar five or 10 carriers with whom they're appointed. And so for them, the golden promised land is differentiating and having something that is truly different than the 500 or 1,000 other agents that are selling in their town or their city or their state. And so we use our position as a relatively new company and a relatively new product, in agents in the thousands, not in the hundreds of thousands, selling this to say, "You can differentiate, you can advertise through your agency a three-year price guarantee for home insurance." And that naturally kinda piques the interest of the homeowner because-

Ben Markland: Absolutely.

Dylan DiMarchi: A, they probably haven't seen an ad for that yet, and B, they start to picture what, man, if they had this [00:23:00] three years ago what could their life have looked like? They probably would've been saving a lot of money. And so we find that Premium Lock is not a big commission product, but it helps those agencies differentiate and grow their core business of selling more home insurance. And then of course, at the same time, it's a multi-year product. And you tend to see those agencies not only winning new customers, but then retaining those customers for longer because it's three years of term. And so agencies are also spending all this money to acquire customers. It's a real shame when those customers churn After a carrier raises rates, 10 or 20%. And so this is a way to keep those customers happy and seeing agents as innovators and allies that are more aligned 'cause they get a payout when prices go up, rather than agents as kind of the creators of more expensive insurance that are in the way of, cheap home insurance. And so we've been really surprised at the upside at how this small product helps those agents grow their core business.

Ben Markland: Yeah. No, I think it's great, and I really think there's an immediate parallel to a lot of what we're doing here. The benefits broker that we deal [00:24:00] with, everyone's chasing the medical commission and the medical plan for an employer, but, if they need dental, vision, life, disability, and all the other stuff, you're right, you're not gonna retire off of that, commission. But, it makes you stickier. It makes you be able to say yes more to your customer. You're allowed to, deliver on the other things they need or things they didn't even think they needed, right? So I think obviously there's a parallel and working through those brokers is the same way we work. We talked about data for on the underwriting side, but you're right. Data on the lead gen side people know what they got, and they charge a lot for it, a whole lot. A- and Google knows, and Facebook knows.. And you're gonna spend some coin, and you gotta have a pretty high conversion rate to make all that make sense. But just like you, we work with independent agents all over the country, and we've got people that we send $4 commission checks to, and we've got people we send, $15,000 commission checks to. So to me, in our business, that is still the main [00:25:00] channel for distribution, is working through these guys that have been doing it for so long. They've got the relationships. Just like you working with an independent agent in town that probably knows the real estate agents. They might be the real estate agent too. You never know. But, you've got your claws in a little bit more with them. So anyway-

Dylan DiMarchi: Differentiation is the name of the game. That's the key. And whatever you can get to win the attention of that customer, not only to just win the sale, but to actually be different and to be better, that is the secret sauce. And, there are very few products on Earth that are both good for the customer, that they want, and that are helpful for the agent. And so we're super excited to have kinda woken up in a position where we're building kind of one of those few products in the world of home insurance.

Ben Markland: Yeah. All right. Thanks, Dylan, again, for sharing your perspective from, as I mentioned, the other side of the fence with property and casualty insurance, something we don't talk a whole lot about, but I think there's a lot of interest, and we probably have a lot of audience members that it's relevant to as well. For our audience, thanks again for listening.

And remember, simple solutions, real results, that's [00:26:00] great leadership.