The Ryan Hanley Show - RHS 125 - Kevin Abramson on How Cover Whale is Making a Splash in the Insurance Industry

Episode Date: November 18, 2021

Became a Master of the Close: https://masteroftheclose.comIn this episode of The Ryan Hanley Show, Kevin Abramson, President at Cover Whale joins the show to discuss why the insurance industry is ripe for innovation and how Cover Whale plans to attack these opportunities. Cover Whale is currently providing insurance truckers by breaching the gap between insurance and technology.This is a tremendous conversation, don't miss it...Episode Highlights: Kevin discusses his firm, Cover Whale, and the work they accomplish. (4:28) Kevin provides his thoughts on what it takes to be a great leader and how to take charge of your own destiny. (10:45) Kevin shares some challenges that he encountered that he did not expect. (16:04) Kevin agrees that having that human aspect in a tech business is not very easy. (20:19) Kevin explains what he means by digesting data faster. (24:10) Kevin elaborates on how he manages to catch and spot bad behaviors in an app. (27:22) Kevin states that failure is part of being a start-up company. (32:35) Kevin shares his vision and plans for the future for his company. (38:01) Kevin talks about giving value to the insurance industry and making a difference. (48:14) Kevin shares the importance of having accurate and reliable metrics in a business. (53:38) Key Quotes “I would say, you know, we've got a lot of tech people at our company, but at my core, I'm an insurance person that really loves tech. And it's not the other way around.” - Kevin Abramson “It's been an industry where data has been prevalent, heavy, you know, lots of data, massive amounts of data. I think the difference-maker is being able to digest that data, but also to digest it faster, in real-time.” - Kevin Abramson “I think, if we look at where we'll be two years from now, one of the core tenants in our business and our mission of the company is, we will continue to take risks.” - Kevin Abramson Resources Mentioned: Kevin Abramson LinkedIn Cover Whale Reach out to Ryan Hanley Learn more about your ad choices. Visit megaphone.fm/adchoices

In a crude laboratory in the basement of his home. Hello 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 there's a there there. They 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 insurtech-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, Coterie Insurance, C-O-T-E-R-I-E Insurance, C-O-T-E-R-I-E Insurance, C-O-T-E-R-I-E Insurance, Coterie Insurance. Go check them out. Get appointed if you're right in small business. Absolutely tremendous company.

Take a look. I want to give another big shout out to our friends over at Donna for Agents, Aries Analytics. Donna is doing tremendous work helping pull together data, making it manageable, making it easier to understand, and then ultimately, and 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, understand 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. Aries Analytics is the parent company.

You know, Ron and Agarog 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 gonna 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 gotta love the zoom you know yeah exactly how are you i'm good dude oh i appreciate you uh i appreciate you coming on the show yeah now looking forward to it yeah excited excited for the little chat yeah so um so let's uh let's get right into it man like um you know i feel like a lot of people

uh people who are in kind of the i 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, or maybe have 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 what is Cover Whale? 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, Cover Whale is a tech company. We are focused on changing the landscape of insurance.

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 insured 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 you're, you're in the friend zone as far as, uh, this, this disposition goes, but you know, what was the moment when you said like, this is not being done right. Um, 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 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, 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 company. This is the right space. This is the right everything. And it just felt like now's the time. And I think from a Coverwell standpoint, I think Dan Abrahamson, founder, CEO, did a really good job 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 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 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 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, 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 uh 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 uh 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. Um, you know, and the, and the thing that I have grown, I've always had an appreciation for, but now actually being an entrepreneur, um, you know, i've grown even deeper uh 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 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, someone who like a couple of big contracts go away and things fall apart, or if the tech doesn't work, 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 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. And 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. Whether it's finance, whether it's tech, whether it's data, telematic, 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 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. 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, that's why I do reiterate to people.

It's like, look, this is startups aren't for everyone. 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. You know, now then I went to a kind of a boutique reinsurance broker with Tiger Risk. And I saw like, you know, how it works at different organizations, at different sides.

I think, to your point, though, it's the stress level when you are really early stages is 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, 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. 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, we're not about hype. We're not about talk. We're about results. You know, made a decision to bootstrap this from the early days. 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 we wanted to test.

We stressed the system. You know, 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. 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 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, it 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, to continue to push forward despite 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, Wu 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, 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 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. 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. It's going to take really strong, long-term, sustainable relationships.

And 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 I think we realized that, look, you're not going to be successful if you do that. You know, maybe you're going to hit 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 know, like what you're doing. You've got to be honest with them.

You've got to be transparent with them. You can't overpromise. 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'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. Yeah.

You know, that's it. It's like, you know, tech on its own. 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. I think that's really important. So we call it, I completely agree with you and everything you just said, we call it human optimized. It was one of the core, core things, core aspects of our business is that 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 evaluations based on spreadsheet tech numbers and not on the fact that to retain insurance business, you need humans involved. I have not seen a case, and I'm 16 years in, all of which were spent in the brokerage side, 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 40s 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. The humans make it very difficult and never losing sight of that, I think, is a big part of 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, vendor, 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 the human optimized piece is. But the human part 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 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 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 because they're just harder to do. Yeah, no, I mean, I agree 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, 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 Whale 2.0 is going. I know where 3.0 is.

But I think articulating that and making sure that everyone, you know, no matter what their role is in the organization, truly understands that. But yeah, I mean, to your point, I mean, that's something that's something we've got to work on and I think externally as well. Why start with small fleet commercial auto? 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, you know, needed technology

from the standpoint of, you know, look, small fleet, owner-operated 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. 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. And I think that adds to maybe number three, it's complexity, right? Commercial trucking insurance line, it's complex.

It's not an easy line of business. People have gotten it wrong for many decades. And I think that's what makes it attractive. And I guess I would just add maybe the fourth kind of item, it's expensive. Insurance can be pretty high. These insurers are paying at times 15,000, 20,000 a truck. From that, 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 we've got to find a group of insureds 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 I think we are attempting to diversify the charges based on better behavioral models, real-time data, and the technology. One of the things that you said early on about what is Cover Whale, what is it? One of the words you used was digesting data faster. I think I'm interested in that. One, what does faster mean in real terms? What does that actually look like? And why does digesting the data faster, like how does that improve the process or

add value to the process? Yeah, you know, 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. But I think the difference maker is being able to digest that data, 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, if you think about kind of the, you know, the,

I guess, traditional insurance model, there's a lack of innovation. You know, innovation is not a core tenant of large insurance companies. It's almost frowned upon, you know, 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. And I think that's the key. How do we identify those kind of claims before they take place? And how do we rectify those? And I think that's where digesting the data 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, 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. Other drivers should be paying probably twenty seven dollars. Unlikely it'll 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 catch bad behavior in the act? Because 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, we've heard similar language before. Progressive has been trying to stick dongles in cars for 25 years now and nothing has really changed. So how does that start to manifest in a way that actually does produce real results? Because like root can't turn a profit, Metro mile can't turn a profit, you know, all these usage based, you know, kind of, kind of methodologies haven't seemed to bear fruit yet. Is there a different way? Like 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 real great, on a Ryan Hanley show exclusive, I'm okay with that. No, I'm just

kidding. You'll mark this down. I'll take 20 seconds. 2021. But yeah, I mean, it is, it's trying to leverage every piece of data you can get your hands on. 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 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 got to coach so you 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 a price for that risk. So, you know, I think that's, what's fun about this. It's, there's no right answer. 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 been built. But we're not, you know, we're not kind of resting on our laurels. I mean, this is, 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 just, you know, talking 30,000 foot level, 10,000 foot level, 1,000 foot level. 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 I don't know. I mean, I think that's what, once again, that's what makes it exciting. I mean, that's where being at a startup is fun. You got to enjoy the journey of a startup. It's a grind. But I think from that standpoint, it's like, look, 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. Yeah. 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. We had David McFarlane from Coterion. I've had Dax Craig from Pi Insurance on the show. And 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 like you, whatever, 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 to growth 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 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, we have to continue to support and appreciate. And it's why I love having, you know, people from the insure tech 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 change that you've made gets understood and disseminated and the industry as a whole grows and continues to prosper and all that good stuff. Like it's just so important that we understand these concepts and we support companies and people are aware. It's why, you know, I love getting people, helping people become aware of companies like yours. 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. And in 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, 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 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. Share the show, subscribe if you're not subscribed. And I'd love for you to leave a comment about the show because I read all the comments or if you're on Apple or Spotify, leave a rating review of this show. I love you for listening to this show and I hope you enjoy it listening as much as I do creating the show for you. All right, I'm out of here. Peace. Let's get back to the episode. Yeah. I mean, I think from our perspective, we're obviously clearly two years in, we've got thousands of policies. We've got a lot of premium

on the books for where we are. But I think 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've 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. 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 gonna 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. You know, but let's not do it at the risk of like screwing up a relationship. You know, let's experiment, 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, no matter what our size is, that 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 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 an mga 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 Yeah, no, great, great question. Yeah, so from a perspective of, you know, at Coverwell right now, we are kind of an MGA model. 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. But obviously, plans and other relationships outside of just that little niche, I would say. But operating an MGA model, we partner with retailers and wholesalers. It is a traditional kind of approach from that standpoint, but offer a chance to allow our distribution partners to get an instantaneous quote or declination within seconds of keying in a pretty painless, I'd like to say, application process. And trying to identify based on the risk characteristics of the insured, does one of our carrier partners have the appetite for that risk? And at 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 traditional, I'd say, in the sense that, you know, MGA model working with traditional retailers and wholesalers, but not traditional from the sense of we haven't just partnered with one carrier. We haven't just partnered with one carrier who has a single kind of appetite. 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. It'll fit your body. 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 we do, you know, Rogue just for everyone listening, Rogue, you know, we're, we're a partner with Cover Whale and 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. Uh, 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 I see what you guys are doing as 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 honestly believe that. I think, I think the way that you're approaching it 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, 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 look in the future, or just maybe at a high level, some of 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. 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 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 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. 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. 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. 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 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. But I think we're also right now, it's at the core, let's get this nailed. And let's do this right. And from there, we'll be able to grow into these other lines pretty easily, I would say.

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

into that. And, you know, we've kind of come out of the little swell that we had from expanding a little too rapidly. 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, going back to making mistakes. I have, I've made that mistake. You know, I feel you on that. Well, so, I mean, give me a little bit more of like the rogue rift story, right? So, you know, we've chatted before. 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. It was great to kind of hear 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. You know, it's once again, I mean, it's just, it sounds like your approach is just, you're attacking this 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, Bold Penguin and TrustedChoice.com. And, 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 I've seen both

sides of that. And that's how I got to the human optimized piece first. I just said, 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 could 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 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 look at a company like Vouch that writes startups, right? Well, now they got to expand because surprisingly, you can't be profitable just writing simple startups. 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, on 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 biggest lawyer in this city and you don't know any of that stuff. So treat everybody like their account actually matters.

And that way and then and then do the hard work of streamlining that process. I mean, there's RT Connector, there's Pathpoint, there's, you know, Amwinds is coming out with a thing. Like there's you guys for trucking. There are digital solutions popping up all over the place to solve these harder to place risks and make the process easier. And 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 yeah, no, I mean, it's exciting. I can hear the passion, which is great. Yeah. Plus, I want to shove it down the throat of every MBA dick who's done a regression analysis in 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, insurtech 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 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 ensure 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, 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 insurtech haven of Troy, New York. So like coming out of this, you know, there's just so much insurtech happening here. No, I'm kidding. I just, I don't know, man. I think what we 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 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 will not leave.

Yeah. I mean, I think you touched on something there and just that last comment, right. Of, 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 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 in insurance for you to bring sexy back. Fair enough. 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, maybe the sexiness of insurance, maybe the sexiest it'll get. But that's where, you know, I think we have done a disservice, right? We have done a disservice of not, you know, broadcasting and making brand awareness of what insurance is and what it means 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 yeah 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. 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. Like, 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. 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. But I really do think like that's why, you know, to your point, this isn't just because you studied it, you know, wrote a thesis in some MBA school. 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? 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 100%. the radar, I think that's why it is such a great opportunity. Yeah. I dude, I I'm with you. I'm with you a hundred percent. You know, I was thinking about, I was thinking about the audit process for general liability policies the other day, right? You, 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 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 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 got to 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 an, there is 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 they're paying for insurance and what their risk actually is. 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 is terrible. I mean, and 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.'s just like like i mean put a hand grenade in it all like right 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 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? 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. You know, and like, look, I mean, to the, you know, to some of the names you mentioned, I mean, do they know who Coverwell is today? Probably not. I'd say 99.9% chance they definitely don't know. 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. Yeah.

And we'll get a good portion of it wrong along the way, but we're okay with that. 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 root, I don't want to bash like, you know, some of the competitors, these insure techs, but they went about it all wrong. I mean, like, look, you cannot just burn carriers. You can't burn reinsurers. 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'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.

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. I wish you guys nothing but success, man. I think that you're going about it the right way. It's exciting to watch companies like yours do new things. And man, I hope there's a day that some of those big companies wake up and they're a little nervous. That makes me feel good. Everyone should be a little nervous every day. And I'm rooting for you, man. Where can people learn more if someone is doing trucking 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, CoverWheel.com, you know, website, very kind of simple, you know, can reach out to any of our management team. We've got, you know, great team that's growing. You know, I think with contractors, we're close to 100 people right now. I mean, the team just continues to multiply. So yeah, I welcome it. Welcome, you know, look forward to working more with you guys and your team. It's a 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 it yeah appreciate the time yeah no glad to be on and

yeah i wish you guys the best luck as well thanks buddy be good all right man sounds good Close twice as many deals by this time next week. Sound impossible? It's not. With the one-call-close system, you'll stop chasing leads and start closing deals in one call. This is the exact method we used to close 1,200 clients in under three years during the pandemic. No fluff, no endless follow-ups, just results fast. Based in behavioral psychology and battle-tested, the one-call closed system eliminates excuses and gets the prospect saying yes more than you ever thought possible. If you're ready to stop losing opportunities and start winning, visit masteroftheclosed.com.

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