Kevin Abramson on How Cover Whale is Making a Splash in the Insurance Industry

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From all of us at Believe, have a Merry Christmas, everyone, and a Happy Holiday! In a crude laboratory in the basement of his home. Well, everyone, and welcome back to the show. Today, we have an absolutely tremendous, tremendous episode for you with Kevin Abramson, the president of Cover Whale. Cover Whale is doing some really innovative things right now in the commercial auto space.

But as you'll hear from Kevin, they have plans to expand outside of commercial auto. I think Cover Whale is one of those companies that we're going to hear more from. I think it's early days for them, although they're already doing tremendous things. So I certainly don't want to downplay the success they've already had, and they have. But it feels to me like those are there, they've got a lot of good people in place, and it seems like one of those kind of more insure tech oriented companies that is going to be a player as we move into the future here over the next five to ten years.

And that's exciting because I think more fresh blood, more fresh ideas just makes the whole marketplace more dynamic, and it pushes legacy players to innovate because, you know, we love our legacy companies. But, you know, we need them to innovate too, and companies like Cover Whale and others push them to do so. This is an awesome episode. You're going to love this. Kevin's a good guy and was excited.

We've been trying to hook up for a while, and glad we finally did. With that said, I want to give a big shout out to today's sponsor, and that is Codery Insurance, another insure tech oriented company in our space doing absolutely tremendous things, hitting the small business world. We write a ton of GL and PL with them. They're a big partner for us and a big part of our future at Rogue Risk. And if you're writing small business and you want someone who's going to help you get it done fast, easy to work with, easy for your clients to work with, Codery Insurance, C-O-T-E-R-I-E Insurance, C-O-T-E-R-I-E Insurance, Codery Insurance.

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Donna is doing tremendous work helping pull together data, making it manageable, making it easier to understand, and then ultimately, and then this is where the value add, pulling in third-party data to make the data you have inside your agency more valuable. And what does that actually mean? It means understanding where there's cross-sell, up-sell opportunities, getting a feel for where potential clients may be starting to look to leave and being able to address those issues through their sentiment score. Donna is doing very big things, and whether Donna is right for you today or not, I think it is worth going and getting the demo, understanding what they're up to so that when you are ready to make a move into a tool like Donna, you know what it's all about. You know how it's going to help you, and you're ready to make that move.

Google Donna for Agents. Donna, go to Donna for Agents. Check out the tool. Arius Analytics is the parent company. You know, Ron and Agarag and the Anurag and the whole team over there just doing absolutely tremendous things, and very happy to have Donna as a sponsor because we use Donna here at Rogue, so that's cool.

All right, guys, let's get on to Kevin Abramson. You're going to love this episode. Here we go. Hi, how are you? Good, man.

What's going on? Sorry about the connection. Yeah, I don't know. Got to love the Zoom, you know? Yeah, exactly.

How are you? I'm good, dude. I appreciate you coming on the show. Yeah, no, looking forward to it. Yeah, excited.

Excited for the little chat. Yeah, so let's get right into it, man. Like, you know, I feel like a lot of people, people who are in kind of the, I don't want to, I hate the word insure tech necessarily, but like that are looking into, you know, new companies that are coming up, doing interesting things. Maybe you've heard of what you guys are doing, but I'm sure there's a lot of listeners in the show that just aren't even aware of what you guys are up to, what you're doing. So maybe we just start with, start with the basics.

Like, give us the rundown on, you know, what is Coverwell? What problem are you guys trying to solve? I love it. That's a softball of a question. So I like to start with something I could probably talk for an hour about.

Yeah, I mean, at the core, I mean, Coverwell is a tech company. Like, we are focused on changing the landscape of insurance. You know, broad kind of sweeping statement there, but it's pretty plain and simple. You know, when I say insurance, I don't just mean like a sub-segment of it. You know, focused on small fleet right now, but much bigger ambitions.

So, and those don't just stop at commercial auto. I think it's the entire industry as a whole. You know, we are bringing a proprietary tech-enabled platform that really, I think, at the core, leverages, and I'd say more importantly, digests massive amounts of real-time data to, you know, hopefully more accurately price risk. And, you know, I think in the end, for any insure tech or a traditional player, it's about pricing risk. And who can do it better?

Who can do it faster? Who can do it more accurately? You know, I think, and you know, you've been in this business. I mean, there's a lot of data out there, but, you know, who can digest it in a way that really makes sense? And, you know, quite frankly, I think the industry and maybe the traditional players have proven an unwillingness to think outside the box, to innovate when it comes to pricing risk.

And that's where a tech company like ours comes in. So, you know, I think focused on small fleet right now, but it really, it's all about data, it's technology. And it's just the changing way of the approach of how we are kind of looking at the business. What was the, you know, where did you get this from? Like, I mean, I obviously wholeheartedly agree with you.

You've come on a friendly, you're in the friend zone as far as this disposition goes. But, you know, what was the moment when you said, like, this is not being done right. And, you know, I want to be part of making this change, you know, taking on this opportunity. Like, when did that hit you? Was there a specific moment?

Was it just being part of the industry and seeing things or, you know, what was kind of the impetus to go, we're going to change this cover, you know, cover whale is going to be the thing. This is how we're going to do it. Yeah. I mean, it's another great question. And look, I guess I would say, you know, we've got a lot of tech people at our company, you know, but at my core, I'm an insurance person that really loves tech.

And it's not the way other way around. You know, I've spent time at various corners of the industry, whether it's on the underwriting side as a broker, you know, my former kind of role at Tiger Risk, you know, I came across all insured tech, was heavily involved in that aspect of the business. I got to see what people were doing. And I had the purview to really kind of understand, you know, who maybe had the right kind of recipe. I met the folks at cover whale, they were a client of mine before joining.

So I really got to know the inner workings of what the platform was, you know, how I think the team was going about their approach. And, you know, I think there was just so much opportunity that just, you know, told me, I just, I want to be a part of this. So I think it was a case of, yeah, I mean, this isn't easy. Like, you know, nobody has figured it out. But, you know, it's about taking a calculated risk to just say, yeah, this is the right time, this is the right company, this is the right space, this is the right everything.

And it just felt like, like now's the time. And, you know, I think from a cover whale standpoint, it's, you know, I think Dan Abrahamson, kind of founder, CEO, did a really good job kind of laying out the vision, building that proprietary tech platform to really attack the industry. And, you know, it's just focused on attracting really talented people. And that's what kind of gets me excited. It's, it's fun to be at a place where you're building.

It's fun to be at a place where you're attacking, you know, kind of the traditional players. You know, but it's not easy, right? I mean, it's just, it's not easy. And I think, you know, I've said it to the team on, you know, a consistent basis. And I say it to myself probably every day on a daily basis.

Startups aren't for everyone. You know, it's hard. And, you know, I think kind of, you've got to be ready for it. You know, you've got to mentally, I think, be prepared for it. It's not necessary for everyone.

And, you know, for me personally, it was just, I'd been in the industry a couple, a couple decades. And, you know, this is a challenge that I just saw, like, you know, I want to go after it. So that was like a personal kind of view. That's awesome. I can reiterate your statement that a startup is not for everybody.

The emotional rollercoaster that you have to deal with on a day-to-day basis. You know, and the thing that I have grown, I've always had an appreciation for, but now actually being an entrepreneur, you know, I've grown even deeper, I guess, appreciation for is that I feel like it's easy to snipe. And we've all done it. I've done it at people who are trying to do something, right? It's easy to see what, you know, from the outside and question different decisions.

But when the buck stops with you, when the decisions you make, I think a lot of people, most people are used to the fact that if I make a mistake, the worst thing that happens is like, maybe I get fired. Maybe that's like the absolute worst thing that can happen, right? But in most cases, if I make a mistake, my boss will figure it out and I'll get yelled at or I'll get taken off the project, but someone will straighten it out and everything will be okay. Man, but when you're at the top in leadership, not just the very tippy top, but when you're in the leadership layer of, in particular, a non-established startup, you know, someone who like a couple of big contracts go away and things fall apart, or if the tech doesn't work, you know, there's no, there is a level of consistent and underlying stress in every decision that most people I feel like who haven't lived that just can't relate to. They just don't understand what that is.

And when you're able to execute, despite that, even if I don't agree with your decisions, I've grown a tremendous amount of respect because it is not easy. I couldn't agree more. I mean, I, you know, I'd like to relate it. You know, I talk about this with my wife. I mean, I feel like, you know, I am playing like a real life chess match.

Yeah. You know, where I'm constantly making calculated decisions where you're trying to connect the dots. You're trying to absorb and digest every kind of piece of data from your people, but everything's connected. It's whether it's finance, whether it's tech, whether it's data, telematics, underwriting, and then you've got to, in the position you are, you're trying to lead this organization to get it to the next level and the next level after that. And it's trying to connect the dots as quickly as possible and, you know, absorb it.

But yeah, I mean, you got to take risks. It's, it's going, you're going to be making those decisions, um, with imperfect data in front of you. And that's the stress. I mean, there is, you know, we've got a lot of people who have bought into what we're trying to build here, but they've given up pretty cushy jobs. They've kind of taken a shot at kind of like, they want to get on the rocket ship.

Um, and I think that's great. That's the type of people we want, but, you know, I don't take that lightly, you know, and I think to your point, it's, you know, and that's why I do reiterate to people, it's like, look, this is startups aren't for everyone. Um, you know, I couldn't agree more with you of the comment. You know, I think it's at different life cycles. I've worked at large organizations.

I mean, I started my career, you know, one of the largest kind of reinsurance companies. I went to a big three reinsurance broker. Um, you know, now, and then I went to a kind of a boutique reinsurance broker with Tiger Risk. And I've saw like, you know, how it works at different organizations at different size. And, you know, I think to your point though, it's the stress level when you are really early stages.

Um, it's just that much higher. There's that much more at risk. Each decision matters the most. Um, which also is quite frankly, I think what makes it so rewarding, you know, I know I'm going to get a lot wrong. There's probably more days that I make wrong decisions than the days where I make right decisions.

Um, but as long as you got the North star in front of you and you know where you want to get to, and you know, I think that's the key, you know, it's, it's clear though. I mean, I think my team would say it and my wife would surely support it, but I mean, I screw a lot of stuff up. Um, you know, there's no question. And I think as a management team, we're probably, you know, we're, you know, we fix one thing, we break two things, but I think that's what's important. You know, I think that the path that we've taken at cover whale, um, we're not about hype.

We're not about talk. We're about results. Um, you know, made a decision to bootstrap this from the early days. Um, you know, but we didn't go raise money like most insure techs do based on a theory. You know, we had hypotheses that we tested.

We had theories that like, you know, we wanted to test. We stressed the system. You know, we, we broke a lot of stuff. We had to get on bended knees to say, I'm sorry to our partners. We screwed it up.

Give us a second chance. Um, but that will lay the foundation for us to, you know, take cover well, where we're trying to get to. Plus no one's going to remember any of that shit. Like that's the, that's the thing that, well, no. And, and, and I, and it's true.

Like, you know, what is amazing, what is absolutely amazing to me is, um, when you read, you can, you can read the, every once in a while, you see these stories come up of really successful companies and like bad decisions they made, right? Like this product that didn't go anywhere, this logo change that they didn't like immediately reversed on a year later. And you're like, you know, if this article was never written, I wouldn't even remember that that happened. You know, because all, I think it takes so much, we'll use the word guts to be politically correct, I guess, uh, to continue to push forward despite of mistakes. And, and I think that's ultimately what people respect and appreciate and admire is that they kept going, they kept pushing and you get to a certain place and people kind of forget.

Any misstep or most of the missteps that it took to get to that place, because what they care about is you now have a product that works for them, that makes their life easier or better or whatever. And it's just not, I think it's just not easy to get to that point. So to me, I look, you know, in the moment, obviously you sometimes have a hard time, like, you know, woo sighing and getting back to that, you know, a little, that Zen moment, but you get, if you can just remove yourself, even for a few minutes or a day, oftentimes it's like, okay, that's behind us. Next, next problem. Let's go solve the next one.

Okay. You know, you know, keep, keep moving forward. So my question for you is, you know, I'm, I'm interested, like what was one of those things, like what, what was something that even if it's anecdotal, like you, you had hypothesis, you move forward, you know, and you solved it. Like what was one of those big first challenges that maybe, maybe you didn't see coming and you did overcome. Like what was one of those first things for you?

Yeah. You know, I would say probably one of the realizations that I think we've had and the, the epiphany, you know, kind of the, I don't know, like the moment that it really struck me, um, was we are a tech company, like, that's what we are at our core. We're a tech company. Um, but there is a human aspect to this business. This is a relationship business and you can't lose sight of that.

Um, you know, whether it's your partners, whether it's your carrier partners, whether it's your brokers, your agencies, your reinsurers, I mean, this is, you know, to be, to do what we're trying to accomplish, um, you know, it's going to take really strong, long-term sustainable relationships. And I think, you know, I'm not saying that I ever kind of discounted that, but there was a side of me maybe that I put more of the chips and all my chips on the tech side. And, you know, I think we realized that, look, look, you're not going to be successful if you do that, you know, maybe you're going to hit the, the double or the triple. I mean, but that's not what we're going for. I mean, we're going for like, you know, bottom of the ninth grand slam walk off game seven.

Like, and you need, you need people, you need people that buy into you, you know, like what you're doing. You've got to be honest with them. You got to be transparent with them. You got to, you can't over promise. Um, but I think what I, you know, what I really love about this industry and the relationships that I've been able to build over my time in it is, you know, being honest is okay.

Like, you know, there there's forgiving, you know, people out there, they just want to like, kind of know like what you're trying to achieve and they'll support you in it. And I think, you know, that was a little bit of, you know, getting back to the North star that I mentioned, you know, that's it. It's like, you know, tech on its own. Um, I think you're going to struggle, but you know, being like a, you know, tech, tech, tech with knowing that relationships matter and the people side of this business matter. Um, I think that's really important.

So we call it, I completely agree with you in everything you just said. We call it human optimized. It was one of the core, core things, core aspects of our business is that, um, I feel like when I look at the landscape that we're competing against in the digital brokerage business is they've all lost sight of the humans, at least most of my competitors, right? They're all operating off of valuations based on spreadsheet tech numbers and not on the fact that to retain insurance business, you need humans involved. Does, I don't, I have not seen a case and I've spent, I'm 16 years in all of which were spent in the, in the digital, in the brokerage side and the, in the agency side.

I haven't seen a use case yet where someone could present me with numbers where you can retain beyond the forties, uh, without humans involved. And that makes it incredibly more difficult because humans are the hardest part of the business, right? Like the tech, if it were just tech, it would actually be really easy. Um, the humans make it very difficult and, uh, never losing, never losing sight of that. I think.

Is a big part of how you have, how you find success. It doesn't mean, you know, I think there are many aspects of what we do day to day, both on the carrier, uh, vendor, uh, uh, brokerage side where we need to remove humans for some of these processes that the humans don't actually add value in certain aspects of it. I mean, that's really what the optimized part of, of the human optimized pieces, but the human part is still has to be there. If there's not a phone number that I can call to yell at somebody or, or I can't drive to your office and, and yell at you, you know what I mean? Like if I don't feel comfortable in that, I'm not going to stick around.

And, um, it's, it's really interesting. I just, you know, it, it, these are the lessons and some of the core concepts that I feel like are so, um, they're almost like the baseline, but they also present a major opportunity because so many of the, of our peers in the industry have, have forgotten them or chosen to, to ignore them, um, because they're just harder to do. Yeah, no, I mean, I agree more with everything you just said there. I think the, the human aspect is, it's not easy, right? So to your point, um, you know, like, yeah, the tech side is like, it's something where, you know, it's unemotional, it's factual.

You can kind of, you can kind of run with it, but you know, I think even just from an internal standpoint, it's understanding that, you know, trying to build a culture is hard. Right. And, and making sure that, you know, I think people on the team understand where we're trying to get to, um, I, you know, I think that's something that we've struggled with. I haven't done a good job of that. Got to continue to get better at it because I think in my mind, it's so clear.

It is so I can see it. I know what we're going for. Like I know where cover well 2.0 is going. I know where 3.0 is. Um, but I think articulating that and making sure that everyone, you know, no matter what their role is in the organization truly understands that.

Um, but yeah, I mean, to your point, I mean, that's, that's something, you know, got to work on and I think externally as well. Why start with small fleet commercial auto? It, you know, in a way, no brainer from the sense of, and sometimes maybe it's a little bit better to be lucky than smart, but you know, it is an area that just needed technology. Um, you know, needed technology from the standpoint of, you know, look, small fleet owner operator demand, number one, commercial trucking insurance is in high demand. That's a trend that's not expected to reduce anytime soon, right?

Number two, I think this insurance that we are selling, you know, it's a need to have, it's not a like to have, you know, this is required. It is a key component of a trucker's livelihood, right? This is their second highest cost side, you know, behind fuel. Um, and I think that adds to maybe number three, it's complexity, right? Commercial trucking insurance line, it's, it's complex.

It's not an easy line of business. Um, people have gotten it wrong for many decades. And I think that's what makes it attractive, you know? Um, and I guess I would just add maybe the fourth, you know, kind of item, it's expensive. You know, this is insurance can be pretty high.

These insurers are paying at times 15,000, 20,000 a truck. Um, you know, from that standpoint, I think that there is a commitment from the insured. There is a willingness to do whatever is humanly possible to lower that cost. How do they do it? How do they get safer?

How do they make sure that based on their behavioral driving, they can reduce the cost? And I think that was kind of the key there, you know, where it's, we've got to find a group of insured that actually buy into the mission that we have, which is we want to lower the cost of insurance, especially for the good drivers. I mean, that's it. Many of them are overpaying, you know, the good drivers are quite frankly, they're paying based on the averages for the bad and the really bad. And, you know, I think we are attempting to diversify the charges based on better behavioral models, real-time data, and the technology.

Um, you, one of the things that you said early on about, um, you know, what, what is cover whale? What is it? Uh, one of the use, one of the words you used was digesting data faster. Um, I'm, I think I'm interested in that. What, what is one, what does faster mean?

Like in real terms, like what does that actually look like and why does, uh, digesting the data faster? Like how does that improve the process or, or add value to the process? Yeah. You know, I, I think from a standpoint of like, look, you know, data and insurance is not, you know, nothing new, right? It's been an industry where data has been prevalent, heavy, you know, amounts, lots of data, massive amounts of data.

Um, but I think the difference maker is, is being able to digest that data. Um, but also to your point is digest it faster, right? Real-time. How do we take that data and how do we make real-time decisions based on that? Right.

So it's not just, you know, if you think about kind of the, you know, the, I guess, traditional insurance model, um, there's a lack of innovation that, you know, innovation is not a core tenant of large insurance companies. It's almost frowned upon, you know, and, and data in that sense, it's like lack of technologies, lack of collection, the use of data suboptimal, you know, actuarial models are based on historical kind of easy data correlations that infer the likelihood of a claim taking place rather than live data that's predicting on a real-time basis of what events could be happening soon, as well as catching bad behavior in the act, you know? And I think that's, that's the key, you know, how do we identify those kinds of claims before they take place and how do we rectify those? And I think that's where digesting the data, um, quicker is important. I mean, that's the game changer.

That's, that's where we're going to be able to define, you know, whether we won or lost in this race. And, you know, we are, our mission is, is that look, you know, based on the traditional models, risk modeling is based on a portfolio approach where the averages pay, you know, the bad, the good, and the ugly and the good pay for the ugly rather than what it should be, where you attempt to diversify the charges based on better behavioral kind of model where it's the individual, you know, some drivers out there should probably be paying a half a million dollars for their insurance because they're that bad. They're that risky. Um, other drivers should be paying probably $27 unlikely to ever get that low, but I think that's where it's the digestion of that data to essentially lower the cost and make it as affordable as possible and pass that cost savings on to the insured because you can do it in a very tech efficient manner to reduce the expense ratio, which we all agree in this industry is just way too high. Now, is that telematics or how do you, how do you catch bad behavior in the act?

Cause I, I, I think everybody philosophically would agree with you. I think that as insurance, I think anyone who's sold insurance for any period of time in our space would say, you know, we've heard similar language before, you know, progress has been trying to stick dongles in cars for 25 years now and nothing has really changed. So how do you, how do you start to, how does that start to manifest in a way that, that actually does produce real results? It's because like root can't turn a profit, Metro mile can't turn a profit, you know, all these, um, usage based, you know, kind of, kind of methodologies haven't seemed to bear fruit yet. Is there a different way?

Like, well, how are you attacking that problem? Yeah, no, I mean, it's a great question and you know, I'm not to say I'm going to punt on this one, but you know, probably not going to sit here and just give up the secret sauce. I would say, yeah. Telematics. I mean, if you want to give up the secret sauce on a rogue, on a Ryan Hanley show exclusive, I'm okay with that.

No, I'm just kidding. You know, mark this down. 2021. Um, but yeah, I mean, it is, it's trying to leverage every piece of data you can get your hands on, um, real time telematics, real time, you know, kind of just every aspect of data. I think that's the key and, but then you got to do something with it.

Like that's, I think the big difference, you know, you've got to identify what the risky behaviors are. Then you've got to coach. You've got to reach out to these drivers before the risky behavior leads to an accident. Um, and I think that, that loop of how do you shorten that loop of collecting the data historical as well as kind of real time. And then, you know, try to figure out that your algorithm really is a better predictor of that risk.

And from there, then you got to price for that risk. So, you know, I think that's, what's fun about this. It's, there's no right answer. Um, you know, I just, I got a lot of confidence in the people we have. I've got a lot of confidence in the mousetrap that's built.

Um, but we're not, you know, we're not kind of resting on our laurels. I mean, this is, uh, you know, I was up in our New York office, you know, for the last three days and it was a lot of, you know, standing in front of a whiteboard and, you know, putting a marker on paper and, and just, you know, talking 30,000 foot level, 10,000 foot level, 1,000 foot level. Um, you know, we're not just, I think we don't have our blinders on. We are constantly trying to improve what we are doing here, what we're building. And yeah, I don't know.

I mean, I think that's what, you know, once again, that's what makes it exciting. I mean, that's where being at a startup is fun. Yeah. You know, you got to enjoy that. You got to enjoy the journey of a startup.

Um, it's a grind, but I think from that standpoint, it's like, look, if you ask, if I was to give you the open and honest, you know, kind of response right now and gave you the secret stuff, I can guarantee if you asked me that question six months from now, it'd be a completely different response. You know, it is every day trying to push for more and more and get better. I think that's the competitive advantage in my opinion that the startups have. Um, we had David McFarlane from, uh, Coderion. I've had, uh, Dax Craig from, uh, pie insurance on the show.

And, you know, I think that, I think what a lot of you guys share, um, is this ability unlike the large traditionals who, who, you know, I give a hard time to. But have done, have done a lot of really good work for a lot of long, for a very long time. Right. And they still present the bedrock of our industry for sure. And, and, um, and I just, I always like to have respect for, for where we've been.

That being said, when I, when I talk to guys like you, people, you know, like you, whatever, um, you know, founders, leaders, people who are, who are really trying to make the decisions. You can turn on a dime. You can test things. You can spin off little test cases and test algorithms and, and data sets and try things that, you know, as you said, you know, it is both their strength and their weakness, you know, for a traditional carrier change can, can really, when you think about how large some of these carriers are, a travelers, a nationwide, a Hartford, a Liberty, like, like when you think about how large they are, really all change can do is hurt them. Right.

Because even, even a good change will be such an incremental will be so incremental to growth for the most part, you know, unless it's some revolutionary thing, it'll be so incremental that the risk isn't worth the reward where for you finding that, you know, little piece of the algorithm that you can tweak or that one data point can have such a, a, a, a, a large impact in your business and its trajectory and the change that, um, it's worth it to you to have all these different tests going. And I think that's why, um, while we always need to have respect for where we came from in the history of our, of our, of our space, because I think that's a big part of success. Um, we have to continue to support and appreciate, and it's why I love having, uh, you know, people from the insure tech and, and kind of change makers on the show, because it just, this is how we get to the next level. Like we need you to be successful so that everyone over time lagging and you have your success and all that and find your spot and build your market share. But over time, we eventually the, the, the change that you've made gets, gets understood and disseminated and the industry as a whole grows and continues to prosper and, and all that good stuff.

Like it's just so important. It's that we understand these concepts and we support companies and, and people are aware. It's why, you know, I, I love getting people, helping people become aware of companies like yours. It's, it's an important part of our space. What's up guys.

Sorry to take you away from the episode, but as you know, we do not run ads on this show in an exchange for that. I need your help. If you're loving this episode, if you enjoy this podcast, whether you're watching on YouTube or you're listening on your favorite podcast platform, I would love for you to subscribe, share, comment. If you're on YouTube, leave a rating review. If you're on Spotify or Apple iTunes, et cetera, this helps the show grow.

It helps me bring more guests in. We have a tremendous lineup of people coming in, uh, men and women who've done incredible things, sharing their stories around peak performance, leadership, growth, sales, the things that are going to help you, uh, grow as a person and grow your business. But they all check out comments, ratings, reviews. They check out all this information before they come on. So as I reach out to more and more people and want to bring them in and share their stories with you, I need your help.

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All right. I'm out of here. Peace. Let's get back to the episode. Yeah.

You know, I mean, I think from, you know, from our perspective, right. You know, we're obviously clearly, you know, two years in, um, you know, we've got thousands of policies. We've got a lot of premium on the books for where we are, but, you know, I think, you know, if we look at where we'll be two years from now, you know, one of the core tenants in our business and our mission of the company is we will continue to take risks. I mean, and that is, I think something different that, you know, the larger players can't do right. To your point, the risk reward, it's just not there.

I think for us, I mean, you know, no matter what size we get, we will, failure is okay. Like you just got to identify failure very quickly and then rectify, change course. Like, and if you can't do that, you know, then to your point, I mean, yeah, it's just, it's not worth it. And I think that's the key of like, you know, where we're starting. Um, you know, I think that's one of the keys that we try to tell people, you know, when they're kind of joining the company, it's like, look, we're going to, we're going to mess some things up.

Failure is okay though. Like, let's have our eyes wide open. Let's identify that failure quickly. And then let's change course, you know, let's experiment, um, you know, but let's not do it at the risk of like screwing up a relationship, you know? And I think that's, you know, the key thing from, from our perspective of, you know, being a startup, it's, it is, it allows you, it affords you, you know, you're expected to kind of take that risk, but I'd like to think, you know, years from now, um, no matter what our size is, you know, we'll still have that.

That'll still be in our DNA because it's just, I just don't think you can continue to push the organization where you're trying to get to that next level or the six levels above if you're not doing that. Yeah, I agree. So, uh, to give people just some more context, you sell through brokers, right? Through agents. Um, and like, is it, are, do you have your own paper?

Are you at MGA? Are you, are you going that route? Are you wholesaler? Like what, uh, just maybe give some people just some more kind of more tactical context to what you guys have going on. Yeah, no, great, great question.

Um, yeah. So from a perspective of, you know, at Coverwell right now, we are kind of an MGA model. Um, but I think different than most MGAs, we have, you know, multiple carrier partners. So right now we have, you know, eight carrier partners that support in the vision of what we're doing. We're focused on the commercial auto space.

I'd say mainly on the small fleet and mid fleet size of trucking. Um, but, you know, obviously plans and other kind of, you know, relationships outside of just that little niche, I would say. Um, but operating an MGA model, we, we partner with retailers and wholesalers. You know, it is a traditional kind of approach from that standpoint. Um, but offer, you know, a chance to allow our, you know, distribution partners to get an instantaneous quote or declination within seconds of keying in.

You know, a pretty painless, I'd like to say, you know, application process. Um, and, you know, trying to identify based on the risk characteristics of the insured, you know, does one of our carrier partners have the appetite for that risk? And at that case, you know, kind of match the risk with the carrier appetite. So it is a, it's traditional, I'd say in the sense that, you know, MGA model working with traditional retailers and wholesalers, um, but not traditional from the sense of we haven't just partnered with one carrier. Um, we haven't just partnered with one carrier who has a single kind of appetite.

Um, it is really trying to be a distributor of risk and match those, you know, be add value add on both sides, value add to our carrier partners. Like you want this particular risk, we can get it for you. We'll find it. Um, it'll fit your buy, you know, we'll find what can fit your box. And I think same thing on the, on the retail and wholesaler side.

So, you know, I would say traditional, but not traditional, if that makes sense. Yeah, no, that, that does. And, and, you know, in, I'm not that I need to be transparent about this, but, uh, we do, you know, rogue just for everyone listening, rogue, you know, we're, we're a partner with cover whale and, um, we, we, we're, we're testing. We'll say, uh, you know, we are testing the waters on truck. We get a lot of inbound trucking opportunities and we are testing on whether or not we want to build a trucking division and really go all the way in.

Um, and it's a big commitment if you do, um, it is not my personal expertise, but, um, we have potentially some people in house who have kind of wanted to take it on and make it theirs. And, um, I see what you guys are doing as a, a, a major, major component of that. Like, I just, I couldn't, I couldn't imagine trying to take on trucking and not be partnered with what you're doing. Like I just, to be honest, and I don't mean that because you're on the show, I, I honestly believe that. Um, I think, I think the way that you're approaching it, um, is tremendous.

That being said, that, that excites me when you say you're not going to start, stop with small fleet trucking, because what that tells me is you're going to start to approach other markets and attack other markets. And if you do it with the same methodology, that can be really interesting. Is it the, you know, where, you know, do you have the ability to share maybe where some of the places you might be trying to go or, or look in the future, or just maybe at a high level, some of the philosophical beliefs on, on where things are going and where you're looking? Yeah. I mean, I think, you know, the easy answer to that is I think, and, you know, it's taking what we've learned in kind of that small fleet space and deploying it elsewhere.

Um, wheels business across the board is the easy kind of low hanging fruit of, you know, outside of just kind of that small fleet trucking. But, you know, I think what we've kind of learned over the last two years and what we've, you know, continue to learn every day, um, that will lead us to what the next line of business is. There's no question that this, you know, what we do, it might not be perfect for every single line of business out there. You know, we're never going to likely get into, you know, fortune 1000, DNO, um, you know, it's not going to be a fit, but there is, you know, we are constantly kicking around what that next move is. Um, you know, I think we also, we want to make sure that like, look, we got to get, you know, where we're focused on right now.

We got to nail this. And, you know, we got to make sure, have confidence that we have nailed it before you move on and you bite more of the apple. Right. I think that's as a startup, you know, that's the other, you know, kind of the decision-making process, right? There's so many different places you can focus.

There's so many different like things you could do, um, to test, to experiment, but you got to get your core business nailed really, really tight, take all the lessons you learned. Um, and then, you know, really kind of try to find where do I now deploy all those lessons we learned and where do we now kind of do it even better in the next line? So, you know, I would say to be honest with you, um, yeah, we've got, uh, you know, we've got a handful of areas that we're really kind of focused on researching, testing. Um, but I think we're also right now it's at the core. Let's, let's get this nailed and let's do this right.

And, you know, from there it'll, we'll be able to grow into these other lines pretty easily. I think that's a, a really good point. And it's actually, um, an early mistake that, that I made, um, we were primarily focused on workers comp and doing a very good job growing rapidly with comp and then, um, started to, started to expand a little too much into other lines, uh, as, as lead-ins, right? Obviously we write, you know, full spectrum property casualty, but, um, on the commercial side, we don't do a whole lot of personal, but, um, you know, as a lead-in, you know, lead-in as being that source where you think comp first, and then we cross hold into other lines that was working very well, uh, continues to do good, but we probably could have pressed that button 10 more times and gone even deeper into that. And, um, you know, we're, we've kind of come out of the little swell that we had from, from expanding a little too rapidly.

Um, so, so I guess things will work out in the end, but that's definitely when I look back at say like spring of 2021, you know, making that move outside of comp, as you just said, and, and, and, and starting to expand into other lines first, like cyber first and like cyber first, in my opinion is really, really difficult sale. It's a, it's a really tough place to go cyber first, cyber second cross sell. It can almost be like a no brainer, but cyber first is very difficult. And, uh, we kind of learned that lesson by taking it right on the nose. And, um, it's just, it's just interesting.

You know what I mean? Now, now I can agree with you wholeheartedly, you know, but I, but I've made that mistake talking and going back to making mistakes. I have, I've made that mistake. You know, I, I feel you on that. Well, so, I mean, give me a little bit more of like the rogue risk story.

Right. So I, uh, you know, we've chatted before, um, you know, I kind of know, I'd say surface level, did a little homework, kind of listened to some of your podcasts, which I love. Um, it was great to kind of hear, um, some of the folks that you had on and yeah, I don't know, give me a little bit more about like what you guys are trying to achieve. Yeah. Um, you know, it's once again, I mean, it's just, it sounds like your approach is just, you're attacking us from a completely different mindset, which I think we love.

I mean, that's exactly the type of partners we want, but yeah, give me a little bit more. Yeah. So, um, my, I came at this from, you know, previous 14 years of being both a chief marketing officer for two different insure techs, both penguin and trusted choice.com and, uh, and then eight years as a broker. So, you know, I've, I've hawked home and autos across kitchen tables and I've sat in the 42nd floor of just about every major carrier in the country. And, you know, heard CEOs tell me they can't wait to get rid of agents.

So, um, you know, I, I've seen both sides of that. And what I, that's how I got to the human optimized piece. First, I just said, when I, I'm going to build a digital brokerage, which removes the non-value touch points so that the humans can spend more time on the real problems that drive retention and relationship. One 10 minute call where someone on your team solves somebody's problem could create a 10 year customer. And they can never talk to a human ever again in those next nine years.

But if you can give them 10 minutes of your attention and solve that problem in the moment, they'll just assume that you're always there forever and never leave. So, you know, I think that's a lost concept in the digital brokerage world. That being said, the second thing that I wrote down was no customer left behind. So when I look at the marketplace, everybody's going after the easy stuff. It's easy, easy, easy consultants, office risks.

You know, you look at a company like vouch that writes startups, right? Well, now they got to expand because surprisingly, you can't get, can't be profitable just writing simple startups. You know, you write, you look at all these companies and they're fighting over the same easy market. And what I said is we're going to do the easy stuff easy, just like everybody else. That's the baseline, but we're going to do the hard stuff easy too.

And that's hard, but I don't give a shit because that's how we're going to differentiate ourselves. Because I don't believe a small business owner should get shitty service or get ignored because they have to go ENS or their premiums are quote unquote, too small, or you can't get an online quote bind rate. So, so what? I have to have a human touch that quote. Do I, is that a best case scenario in the most pro in the largest profit margin?

No, but you don't know whose niece that is or nephew that is, or whose uncle owns. Um, is the, the biggest lawyer in, you know, this city and you don't know any of that stuff. So treat everybody like their account actually effing matters and that way. And then, and then do the hard work of streamlining that process. I mean, there's RT connector, there's path point, there's, you know, Amwinds is coming out with a thing.

Like there are, there's you guys for trucking. There's, there are digital solutions popping up all over the place to solve these harder to place risks and make the process easier. And, um, our goal is to be the universal connector for those people. So we plug into channel partners and we help them monetize 90 to 95 plus percent of their B2B customers where all of our competition is somewhere in the 35 to 55% range. I love it.

No, it sounds great. I mean, it's exciting. I mean, you guys have made a lot of progress in a short time and, um, yeah, no, I mean, it's exciting. I can hear the passion, which is great. Yeah.

Plus I, plus I want to shove it down the throat of every MBA dick who's done a regression analysis and some freaking MBA class, and then wants to come in the insurance industry and tell us brokers that we don't know what we're doing, right? Like 2015, 2016, put a chip on my shoulder when, you know, everybody who'd ever, oh, insure tech seems like an opportunity. I'm going to come in and tell all you guys that the last 440 years of your, of your, your industry's history is crap and that we're going to do it better. Well, yeah, sure. Sure.

Shit. We need innovation. Absolutely. Absolutely. We need innovation.

No doubt without, you know, there's no questioning that, but I, I, I have a problem with people who do not, who come into our space. I love people who come into our space who want to change things, but I don't like when they do it with disrespect for how we got here, because if you don't insure something properly, you ruin someone's life, right? This isn't like, you know, Hey, the, the new, the new iPhone widget that I built doesn't work and I can't text message my buddies with gifts for three hours. It's like, if you don't insure someone's home, right? Their home is gone.

It doesn't magically reappear. So we have to have respect for how we got here. That being said, we need to change. I think things can be done better. And those are the people that I love supporting and talking to and learning from.

And, um, you know, I would be, I would be, uh, it would be intellectually dishonest of me not to say that I do have a chip on my shoulder and I can't wait to be on stage with one of these a-holes and just shove it down their throat. I love it. I love it. So, um, yeah. Plus I'm from the insure tech haven of Troy, New York.

So like coming out of this, you know, there's just so much insure tech happening here. Uh, no, I'm kidding. I just, uh, I don't know, man. I think, I think what we do is really interesting. I think that, um, I think that the lack of sexiness of insurance is what makes it interesting because if you can find ways to make it cool, engaging, fun, get smart people, passionate about this, man, the opportunity is as, as you've said, right.

The people that you've hired and that you work with and the opportunity is endless. It's absolutely endless. And, um, you know, that's why I've stayed here as long as I have. And we'll not leave. Yeah.

I mean, I think you touched on something there and just that last comment, right. Um, you know, I think insurance is, you know, it's viewed by many as just, it's boring. I mean, my wife jokes about it all the time. I think it's, it's easy to just take shots at insurance, but. You know, insurance.

I mean, I think in a way it's, there's a value proposition that is necessary. Right. And I think from the standpoint of, if we can change the way we approach insurance, I think we can, I'm not saying we can put sexy back in insurance, but you know. Well, sexy would have had to be an insurance for you to bring. Yeah.

That's right. Fair enough. Fair enough. Um, but I think there's no question. I mean, it can be fun.

It can be dynamic. It can be interesting. I mean, there's problems that need to be solved. It can be analytical. It can be thought provoking.

And I think that is what, you know, that's, I guess, maybe the sexiness of insurance, maybe a sexy little guest, but that's where, you know, I think we have done a disservice, right? We, we have done a disservice of not, um, you know, broadcasting and making brand awareness of what insurance is and what it means and, and why, you know, young people should be, you know, flocking to this industry. You know, it's, the joke is, it's just a bunch of, you know, C plus students. Right. And, you know, that's not the, that is so far from the truth, right?

You know, it's the people that are successful in this business are the ones with grit, the ones that are like hungry, the ones that are going to keep digging and keep going and keep going. And, you know, I think that's what I think is going to, you know, it makes, you know, it gives you an opportunity to differentiate yourself personally, your company that you work for. Um, you know, but you know, to your point, like, look, we have to do it differently. The old model is archaic. It's silly.

Like, how do you price a risk based on retrospective data and then not touch it for 365 days? Like, that's crazy. Yeah. Like it, it, it's just, you know, you cannot pinpoint down to pennies, like what the right price of that risk is. And I think that's where it's trying to now, to your point, it's like, look, you know, tech was needed, you know, to create the efficiencies, to leverage the data, to digest the data.

Um, and that's, you know, like, you know, the word insure tech is used a lot, right? It's thrown around way too much disruption thrown around a lot. Um, but I really do think like, that's, that's why, you know, to your point, this isn't just because you studied it, you know, wrote a thesis and, you know, some MBA school, um, you know, it's really about like, look, understanding what's been done in the past and how do we improve the process? Yeah. How do we tweak this process?

Um, but yeah, I think that there's just, because we've kind of flown under the radar, I think that's why it is such a great opportunity. Yeah. I, dude, I'm with you. I'm with you a hundred percent. You know, I was thinking about, uh, I was thinking about the audit process for general liability policies the other day, right?

You, uh, you know, on day one, you say, how much revenue do you have and how much payroll you have? Okay. Here's your price. Then you don't think about it again until a year later and you go, Hey, was your revenue this much in your payroll this much? Okay.

You know what I mean? Like, here's, here's your new premium. Yeah. And I, you know, I think about that and I'm like, I could understand when we had to hard mail documents back and forth or fax documents back and forth, like that's as fast as it got that you would think about, you would think about it in those type of, you know, annual terms, but you know, it's just, I feel like there's, there's gotta be a bet. The audit process is such a pain in the ass.

It is a, it's a, it's a transfer point or a, or a, or a, a move point for so many, for so many insureds that audit process and just filling out the forms and they're giving you crap. And then they want to, they got a bill they want to charge you and you got to pay it in 30 days. And it's, you know, and it's gotta be a lump sum and, and they're like, ah, this is terrible. These guys are awful. I'm moving to this carrier over here.

And then it's the same over there. And like, there's gotta be a better way to manage, you know, manage one, whether payroll and revenue for a GL policy are simply the best ways to, to, to price a risk. And two, that annual audit process of those two numbers and like the, just hate that every insured has for that. Like there's gotta be a way to make that better. I'm not the guy to figure that out, but I can, I'm listening to you and I'm going, what you guys are doing that people like you who are thinking about the business, the way that understand actuarial models better than I do.

Like there's a, there's a, there's an, there's a point that could be, that could be easily. I wouldn't say honestly easily. There is a point that could be, and could, has the potential to drastically change the way that we real-time price, how someone, you know, what, what they're paying for insurance and what their risk actually is and, and, and ultimately give them a better experience. Like have them not hate doing business with an insurance company because they're so nervous about, well, geez, if I accurately report my revenue this year, I'm going to have to pay an extra $3,000 in a lump sum. So they lie and then they price in the lie.

And now we're all playing this big game where we're all kind of lying to each other. And, you know, it's just, ah, it just, it's terrible. Well, I mean, and you're, you're going, I know you're going through a fundraising round right now and, you know, you're, you're putting together budgets and you're putting together models and you're projecting it out three years, five years. And it's just like, like, I mean, put a hand grenade in it all, like, I mean, of all that stuff, you know, and to your point of like trying to identify like what the right metric is, the price off of, um, and is it an accurate metric, right? You know, and are we, have we set ourselves up to fail based on what you exactly just kind of said?

It's like, okay, now people are incentivized to not give you accurate data, which, you know, makes it even that much harder. We, you know, pricing on an individual risk basis is hard enough itself, right? And how do we understand the behavioral analytics of that individual insured, but now let alone, how do we make sure we're getting the right data, right? Cause you're making, you know, million dollar bets, millions of dollar bets, um, on oftentimes imperfect data. And I think that is, I mean, that's kind of the side of the business where you just kind of scratch your head and people look at it and say like, oh my gosh, like, this is crazy.

Like, this is what these guys are doing, you know? Yeah. So I don't know. I mean, you know, I do think, I think we, you know, we as an industry, I think we can figure this out. I think we're getting better.

I think even the big, the big boys and girls, you know, they're, they're aware that it, you know, I think, as you said earlier though, it's just hard. It's hard to change for them. It's hard to take those risks. Um, you know, and like, look, I mean, to the, you know, to some of the names you mentioned, I mean, do they know who cover well is today? Probably not.

I'd say 99.9% chance. They definitely don't know. Um, I think at some point they're going to know, and it's going to be pretty soon, you know? And I think that's what does make it fun of where like, look, coming at it from a different angle, you know, that's what allows us to really, you know, take these big shots and we'll, we'll, we'll get, we'll get a good portion of it wrong along the way, but we're okay with that. Um, you know, as long as we know, like, look, our carrier partners, like they are long-term sustainable relationships in this business.

I said it early on. I mean, that's the key. You cannot, you know, the roots, I don't want to bash like that, you know, some of the competitors, these insure techs, but they, they went about it all wrong. I mean, like, look, you cannot just burn carriers. You can't burn re-insurers.

Um, you know, and I think that's like, you know, kind of where our approach has been is like, look, let's build a long-term sustainable company, but like the rocket ship is going like, we are not like putting this in second gear. Yeah. So, you know, I think as quick as possible, but also recognize like we, we've got to be, you know, we've got to be realistic in the sense of we need partners to get us to that next level. And, and that man is why I think you guys are going to be successful is because you are walking that line between having respect for the industry and what you're doing and how it works with the absolute positive need to innovate and try new things and test things and break things and fix things. And, uh, I, um, I wish you guys nothing but success, man.

I'm, uh, I think, I think that you're going about it the right way. It's exciting to, to watch companies like yours do new things. And, uh, man, I, I hope there's a day that some of those, those big companies wake up and they're a little nervous. I, I, that makes, that makes me feel good. Everyone's, everyone should be a little nervous every day.

And, uh, and, and, and I'm rooting for you, man. Where, uh, where can people learn more if, if, if someone is, is doing trucking and, and, and small fleet and wants to learn more about you, where can they go? Where can they connect with you? Yeah. I mean, you know, coverwell.com, you know, website, very kind of simple, um, you know, can reach out to any of our management team.

Um, we've got, you know, great team that's growing, you know, I think with contractors, we're close to a hundred people right now. I mean, the team just continues to multiply. Um, so yeah, I welcome it. Welcome, you know, look forward to working more with you guys and your team. It's a growing team.

And, you know, I don't know, just excited, excited to kind of, you know, I'm on now a different side of the industry. I'm getting to meet folks like you, you know, I was a layer removed in my kind of former life. And this is what's fun. It's really kind of chatting with folks like yourself, understanding how you're attacking the business and, you know, and some of your peers, it's like, how do we kind of collectively figure this out to, you know, I don't know, change the industry. Yeah.

So I appreciate the time. Yeah. No, glad to be on. And yeah, I wish you guys the best luck as well. Thanks, buddy.

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