Take Your Business To The Next Level | Coterie Insurance COO, Kevin Mackey (Podcast 243)

First and foremost, you should be looking to build your business for sustainability. If you build your business for sustainability, it will have value. If it has value, then really what you're talking about, whether it's an exit via IPO or a strategic merger or acquisition, it should be because you're on the offensive, because you know where you want to go and you're selecting the right fundraising source for your next round of growth. Now, certain businesses lend itself better to certain financing structures, whether it be, you know, we're going to franchise as our way of funding our scale versus, you know, go the IPO route. I think that it's important for your business to decide which one. Like for us at Coterie Franchising, of course, makes no sense. It's not even remotely part of our business model. So that only leaves a couple of different avenues that realistically outside of our own sustainable growth, that would get us to that next stage. So it's important for us to kind of know that about our company on the front end.

Our guest today is Coterie Insurance's coo, Kevin Mackey. Kevin leads the company's operations, including finance, accounting, legal scaling, people operations, security, tech services, and customer advocacy. After graduating with a degree in finance and accounting and working with a buy side equity researcher through the financial crisis era, Kevin tapped his entrepreneurial DNA as a founder and technology ecosystem builder in the Cincinnati area for the past decade. He founded his first company, Glue, in 2011 and worked for three years at Centrifuge, a private public partnership with an active network of venture capitalists, big corporations and tech startups. In between startup experiences, Kevin Ghosh wrote the Fearless Front Line, which is a book about organizational and leadership design. Kevin currently splits his time between Chicago and Cincinnati. And Kevin, looking forward to chatting with you today. Thanks for joining us.

Yeah, thanks, Gammon. Really appreciate it.

Yeah. So you've got a really interesting journey in terms of the kind of entrepreneurial side of things and working on the VC side of things as well. Why don't you kind of just walk us through some of your, maybe your bio and how you got here today and then we'll dive into some of the specifics with you. So how did you get into the kind of role that you're in and even in co founding and COO with Coterie?

Yeah, thanks. Thanks for asking. You went through a little bit of that in the intro, but it does really for me start as that buy side equity researcher. So I graduated from the University of Dayton, who has a pretty solid program. It's called the Davis center for Portfolio Management. So in college I was able to get access to, you know, Bloomberg terminals and things of that nature. And I really loved the analysis. I fell in love with, with analyzing businesses. And so that's really where I had started my career in the middle of the, or the beginning maybe of the Great Recession. So I graduated in December of 2007 with a degree of finance and accounting and got my first job in January of 2008. You know, three months later, March 17, 2008, we have bear Stearns collapse. And I'm reading all of this stuff and realizing, whoa, I don't know anything. And so from that perspective, I really began to teach myself how to learn. You know, I just graduated, of course it was undergrad, but you know, that was really the moment where I kind of realized, whoa, there's so much more to learn. And I just really fell in love with it. It was such a fertile time to learn things that were going on, certainly in finance, but also just business in general. And so for the next couple of years I really just immersed myself in the blogosphere, you know, the financial blogosphere. Whether it was Seeking Alpha or any of these other websites, it was just really getting started. And so I just, I really loved that and I really, really fell in love with that piece, but also realized I didn't want to go kind of into, you know, financial services. I wasn't going to be an investment banker or things of that nature. So I had the fortunate benefit of knowing a professor at Northern Kentucky University here in the Cincinnati area. And she and I ended up starting and founding the company Glue. And so it really kind of was a serendipitous opportunity in that I was young, I didn't have children at the time, could kind of, you know, take one of those swings. But of course didn't know anything. I can say in hindsight, didn't have any idea really what I was doing. But as a first time founder, you're kind of feeling your way through everything. So that was really, I would say, the foundation for a lot of the current beliefs that I have in terms of founding subsequent businesses and then of course founding coterie and really building our operations up from nothing, you know, to know more than over 100 employees all over the country and selling millions of dollars every month.

And in terms of. Thank you. In terms of scaling out these organizations as well and building multiple companies. Have you had exits with these companies as well? Have you built and sold or what's that kind of lifeline look like?

Yeah, no exits Currently, in fact, I would say kind of the opposite. I had to shut down glue. And in some respects, I know that certainly we're going to be going for a very healthy exit here with coterie. That's not the exact purpose of why we're building coterie. Nonetheless, we believe that that's going to be a good opportunity for us. But in some ways, I am actually glad to have learned what it is to wind down a business, not only logistically, but also just the emotion that goes into it. You know, you're. You're dealing with other people's money, you're dealing with, you know, the tail end of all that optimism that you have when you begin to start a company. So to me, I actually really value that I had that opportunity especially so young in my career, because I was able to really feel viscerally what it feels like to get it wrong. And then ultimately, for me, that's actually the foundation of what it takes to get it right.

That's super intriguing. We're going to go in there, I'm going to talk a little bit about that, the roller coaster of emotions and also the lessons to pass on. It was funny you mentioned Bear Stearns. My old roommate in college was the head of derivatives worldwide for Bear Stearns at the Cross, and he wrote the book called Bear Trap about the crash of bear stems and why it fell apart. It was funny in. In the book, he mentioned that Lehman Brothers was going to crash next. And I think the book Bear Trap came out about two weeks before Lehman Brothers crashed. I'm like, how did you know? He goes, dude, we all knew. Like, everybody in the industry knew it was a house of cards. But I think there's something interesting for you at your timeline of your career was to kind of be in high school during the crash of the NASDAQ, kind of 2000, 2001 crash, and then to leave your business or, you know, start your business kind of at the beginning of the global financial crisis. Do you find that that has kind of given you a foundation for a little bit more, I guess, realism and a little bit more cautiously opportunistic versus the irrational exuberance that we've seen?

I think that's possible. I certainly have looked at the stock market increases from 2012, I mean, into, you know, 2021, give or take. And, you know, I'm a technical analyst, so I love to read charts. And for me it's like, man, these charts are crazy. You know, how long can you go on the high end, you know, of your of your charts. And so I think that from that perspective, I guess I'd always taken the approach of like, well, there's just only so much energy that a certain market can take before that energy has to go into a different direction. So I think it definitely was a little bit of pragmatism in terms of just looking at what could happen. Full admission. Early in my career as a financial analyst, I was a bit of what you would call a doom and gloomor. I went through the phases of, oh, fiat currency, oh no, are we in deep trouble because of fiat currency and all these things? And of course, yes. I mean, there's elements of truth to a lot of those things. But I think what I saw through that 2008, 9, 10 time frame, at least for a decade or so, is that there was complete unwillingness for our government, at least. This is not a political statement. I just, I believe that it to be a true statement. There was no willingness to let the actual calamity occur. If you read Too Big to Fail and all the other Lehman Brothers stuff, you do realize that there was, there was a bit there that was outside of finance, perhaps. But I do think that, you know, the idea, I'm going to get a little bit into the finance stuff and then we'll take it back. But the idea of credit default swaps coming out of Lehman Brothers failure, I remember studying that and people were like, how is this even mathematically going to be possible? And yet at the same time it persisted. And in some cases, even with AIG and others, we made money on it. So I think that all of those learnings just helped me go to a place where it's like, what is the market? And those supporting the market, what are they willing to do and what can they do? And I think that we've again, not to get too far down that route, but we probably, we've used a lot, you know, you can only spend trillions of dollars a couple of times before you end up incurring, you know, other, other things. So I think that having seen that early in my career was extremely helpful in knowing that just because money comes in at certain times. Yeah, sorry, sorry for the long winded response, but it actually does show up in our business right now. And then I'll turn it back over to you. But the markets have fundamentally changed for fundraisers or especially venture backed businesses like ourselves over the past six to 12 months. And in particular we're in Insuretech or Insurtech as it would so be called. And there's A lot of insurance companies that have gone public and lost people a lot of money. And so again, earlier this year, we kind of went from a place where we've always been fortunate and had a solid balance sheet and been able to raise money, but that money is not a given. And I think that we didn't have to have a lot of conversations with our board for our management team and our founders to understand that. And I think that that's where, you know, some of that early career experience shows up in the current business.

Yeah, that makes a lot of sense. And I'm kind of with you on, I think the market and everything has changed. I mean, you got to be completely moronic to think it hasn't, considering all the signals that we're hearing from bigger companies. So does it give you any. Not concern, but how are you managing some of the employees? Are you talking to the employees about what they're seeing in the news and what they're reading? Like, are you? Because they're reading it too. How do you calm them and make them realize we're okay, we're solid, here's what we're planning on. And then how long do you think we've got with this whole. I know I'm asking the crazy question that none of us know, but how long do you think this is that we're going to have to ride out this period of time, kind of refresh a recession slash, possibly even stagflation?

Yeah, wonderful questions. I'll try to answer them in order in which you ask them, how are we talking about this with our team? It actually comes down to what I say internally as business acumen. That's probably not, of course, the most marketing friendly terminology, but for us, it's really, especially with our younger, or let's just say maybe less experienced professionals, we have to educate them. You can't understand what's happening and even the decisions that we're making as a business unless you understand what our business is and what those macroeconomic factors are. Otherwise, it's just going to be a series of decisions that you don't know. And then you're really relying on trust. Does the team trust that you know what you're doing and what you're talking about? And when you don't have an answer to that, people may fill in their own gaps. So for me, it really does start with not only just the normal communications, you know, team meetings and, you know, just what I would call good organizational hygiene. It actually is taking this lens of I'm educating, I am an educator of our team every single day. And I have to say this is my lens of this education. And just like you started off the question, we don't know what's going to happen but I have to tell you why we've made the decisions that we've made and ultimately what that is going to do for us in the case of our business. Fortunately for us, it is, we do have a strong balance sheet. We have been able to, you know, we, we did some, we went through a reduction of course, earlier in the year which actually put us in a position to raise more money and strengthen our balance sheet to get through this, whatever time frame it is. So that's the second part of the question. How long do we expect for this to last? The benefit of having gone through at least one of these quote unquote black swan events is that I remember thinking viscerally going to a mall in the Cincinnati area, it doesn't feel like a recession. And I remember thinking that because the recession hit different folks at different times. You know, when you have 30,000 people that lose their job overnight in New York City, that's going to impact certain people before it hits maybe a more midwestern town in the central part of the country. I believe that we, as an insuretech or a venture backed business, we have experienced some of the early, you know, this isn't a secret or super well documented. Most and a lot of tech companies are going through layoffs and going through cost reduction measures because we're actually getting finally back to a place where business economics and unit economics really matter. So for me, I appreciate that this whole thing, this whole thing being a cycle of, you know, economics going down, less money to be able to spend, people probably going through their own, whether it's personal defaults or business defaults, banks go through their cycle of having to close up lending. I mean that whole cycle can probably take truly about two years. But for us and our business, because we're servicing small business owners, we actually expect for financially, you know, we've kind of shored up our balance sheet to the point where we can operate successfully for the next couple of years. But we really want to hit that hard because we know that these are the times when small businesses start and we'll be able to hopefully get customers for a very long time if we're able to get them at the inception of their businesses. So we really do look at it as opportunistic.

I love that and I love that you guys were smart enough about actually shoring up the balance sheet as well and doing the reduction of force as well. And I love the fact you even talked about just educating the team and really making sure that they understand. I think too often companies are like, oh, they won't understand the balance sheet, they won't understand the P L. So we'll just ignore it. That's fucking stupid. Like, give it to them in the basics. Like it. You don't have to give them, you know, you can, you can teach them the basic understanding of the economics of our business, the basic understanding of our assets and liabilities and basic understanding of cash flow. So they go, oh, okay, I understand. And, and just even that basic understanding, maybe it doesn't even build enough of an education that they're going to be able to do much, but it certainly builds trust from them to you, that you care about them. And you've also probably discovered a bunch of the rumors that they're running around chatting about that are just grounded in the fact that no one cared enough to talk to them. So I think you're smart in doing it that way. You mentioned that you had worked on the, on the buy side and the VC space and doing a lot of the analysis and stuff. Have you learned anything from. Because a lot of our CEO alliance members and a lot of companies out there are looking to exit. Their organizations are looking to sell their companies. Did you learn anything on the buy side that if somebody wants to build a company for the best possible exit, what are the things that you saw in the analysis that make a company look better than not?

Yeah, wonderful question. I'm actually going to respond kind of for. For myself, visceral, and then I'll get into the analyst answer. I think that first and foremost, you should be looking to build your business for sustainability. If you build your business for sustainability, it will have value. If it has value, then really what you're talking about, whether it's an exit via IPO or a strategic merger or acquisition, it should be because you're on the offensive, because you know where you want to go and you're selecting the right fundraising source for your next round of growth. Now, certain businesses lend itself better to certain financing structures. Whether it be, you know, we're going to franchise as our way of funding our scale versus, you know, go to IPO route. I think that it's important for your business to decide which one. Like for us at Coterie franchising, of course, makes no sense. It's not even remotely part of our business model. So that only leaves a couple of different avenues that realistically, outside of our own sustainable growth, that would get us to that next stage. So it's important for us to kind of know that about our company on the front end. Now I'm going to go a little bit more into the analyst piece of this and I'm going to talk about my industry. And in particular, when I say my industry, I'm going to talk about insuretech, as it has been called, Insurance tech, being Lemonade Root, Metro Mile, Hippo. Those really are a lot of, you know, the four that kind of primarily went public in this realm between the 2020 time frame and currently. It's important to realize what they just went through because a lot of them on paper have made money and lost money for investors. And the reason, if you're in this industry, one of the reasons, I should say maybe the primary reason. But there's been a major focus, as I just said, in all businesses, but in particular in intratech, on unit economics. We have to actually demonstrate that we can write business profitably. And that's actually what had happened in what we'll refer to as InsurTech 1.0. No offense to anybody, but in the insurtechs that had grown in venture capital a couple of years before us and then went that IPO route, they went with the impetus of growth is the first thing that matters. And what the markets have told us over the past six to 12 months is that that was great, but you have to make money for that to sustain. We know that now. So going into whether it's an IPO or a merger and acquisition, we have. I was talking about the balance sheet, but now we also have the strategy and the direction to say we know what the answer key is. We also have time to be able to work that into our current processes. So as an operator, I look at it as we have. We have that golden ticket, the visibility into the future of how we need to operate now to get there. So that's how I kind of look at both of those things. It's not a given that we're writing small business insurance. We were very fortunate to have wonderful underwriters and very, very smart people that build the digitization of our underwriting. But at the end of the day, something goes wrong or you have a catastrophe that you were expecting and you can. You could be in a different circumstance. So really building that into our business, really before we go into massive scale, we think is part of that answer key. And it also means that maybe we actually have to give ourselves this is now an example, not an exact, but we might need to give ourselves 12 more months to IPO, because we know that in 12 more months, we'll have a renewal cycle under our belt. You know, this, this, this, and this. And again, knowing that is a strategic decision, not it's just a race to get to ipo.

Yeah, that makes sense. All right, so you rattled off three of your, you know, the other. Other businesses that are in kind of the insurtech space. Can you explain to us first off, what the insurtech space is, and then just tell us exactly what coterie does and who your typical clients are, and then we'll go into some more. Some more questions.

Yeah, yeah, maybe you should have done.

That, because, by the way, I'd never heard of any of those brands, so I would imagine a lot of our listeners don't. And for you it's like, of course we know them. Right? So, yeah, yeah.

Thank you for bringing me back because this is hopefully maybe the part of that education that we not only talk to our team about, but hopefully your audience. You know, insurance. Insurance is. It's kind of a funny industry to be in because, number one, I'm a new newcomer to insurance. You know, I've been the COO of an insurance company now for about five years, but before that, I was the consumer of insurance as a small business owner. And so that's an important piece of this because the way that small business insurance has typically been distributed is, as we would say in startup land, ripe for disruption. Why? It's because the way that insurance is underwritten historically has been, let's say, you're my agent, you give me something. It could be digital or a piece of paper, but nonetheless, you're giving me something. I'm giving it back to you, you're giving it back to someone else, they're giving it back to you, you're coming back to me. And you see, of course, you know, in that bifurcated way, how that can add up to be a lot of time, a lot of confusion and a lot of headache, yet at the same time, what industry or what buying experience as a consumer in the world can you have something that you don't know what you just purchased, you don't know why it costs, what it did, you don't really know how to use it, and yet you do it every single year, and you're required to do it. So in a lot of ways, the insuretech industry is taking all these old processes that required a lot of what I would Call fixed cost, AKA you're employing a lot of people to do a lot of stuff. And we're able to completely reverse that. So that's the idea of insurtech. Literally, you are taking the insurance industry and all the components and compliance requirements and everything associated with it, and you're digitizing all of it. And you're doing so in a particular industry for a particular market. So our market, and which is why I love starting this business, is small businesses. We are digitizing and attaching small business insurance to what we call places of relevance, AKA apps and marketplaces, where small businesses already are. So here's a use case for that. Intuit QuickBooks. And I do like to joke around, but it's not a joke. As a small business owner, I know that unless you're actively trying to commit fraud, you don't lie to your books. Like, you're only screwing yourself if you actually lie to your accounting books. So from an underwriting perspective, that's a goldmine of information. Because instead of the, well, I'm giving you this piece of paper and I'm guessing how much revenue, we just suck the information in and then use the algorithms to be able to take a process that could take at best hours and at usual days, weeks. And we're able to underwrite your business in two seconds, literally. Wow. My favorite story behind this. I'll share this with you and then turn it back over. So Intuit is one of our partners. And the first policy that we bound with Intuit, the person, the business owner contacted our customer service line. And we should really have this written down in like, S, somewhere in our office. But they had said, I wanted to know if the policy was bound because it was too easy. No one actually believed that it could be that simple. And all we're doing is not that easy. But we're meeting small businesses, data back to them.

It totally makes sense. I have a friend of mine in Australia who used to work on the bank side, analyzing businesses and deciding how much money to loan to them. So he literally took that software, flipped it upside down, and taught businesses how to build their P and L properly so that when they went to a bank, bunch would fund them. I'm like, fuck, it's genius.

That's.

That's all you've done, is you just figured out the most efficient model to get the information to fund it and bind it in a way that makes so much sense. I love. Okay, I get it. Love the model. You've gotten through a couple of rounds of funding, right? Now, how much have you raised.

In total? It's over 100 million. We just went through another round, so pardon me for not remembering the absolute dollar amount, but it's a shade over 100 million.

Okay, so you raised about 100 million. Pretty solid. Like pretty solid proof of concept. Pretty solid. Especially kidding. You're only at the hundred employees. How has that changed the organization and how are you keeping people focused? When money can change the organization, or at least their understanding that we now have money can change the organization.

Show up to work every day to figure out. It's not that easy. It probably is, especially as a national and remote organization. It is one of the things that we have to try and be as intentional as possible about. So I'll tell you a little bit about what we've kind of gone through and then really some lessons that I've learned that we hope to apply now and on an ongoing basis. So the first question of just how we kind of have with the scale when you. This is, this is not rocket science. You know, a lot of people have talked about how you grow from different stages and how it goes from everything being very personal to all of a sudden your job has shifted maybe dramatically. And the way that you have shown up to work and the people that you've shown up to work with has fundamentally changed. That can be extremely difficult for some of your early employees. And then you're really spending a lot of time trying to get your new employees, who you just recruited for the current moment to the same place of your old employees that have given everything for the company and to be where they are. So you have to really go from this place where you're scaling yourself, I call it get big while feeling small. We have to get big while still having this personal connection. The best way that I've found to do that is. This might sound hokey, but I think that it's the best way that I figured out is truly to lead by example. If I want to make sure that all the employees that I will never have time to have a one on one with, if I want them to have the same experience that my employees get, that I have to show up with the same energy, the same intention in every single one of my one on ones and every single one of my teams, that is, I believe, my responsibility. Because first two years of the company I was doing all of the work. And I'm not saying that to be haughty or like I did the world's best job. I like to actually recruit by saying, hey, I want you to take my C plus work and turn it into an A plus. But the fact was that I just had to do a whole bunch of C pluses to just get it up. And then that totally flipped for me. Where I went from the person that was doing so much to then recruiting the people that were replacing me, to then running an organization that really doesn't need me anymore. But that actually is kind of by design how actually we've tried our best to do that, you know, get big while feeling small, is make sure that there's still that personal approach, make sure that our culture still shines, make sure that I'm still always available. But it really is now my team members that should be front and center and are front and center really in most of the work. And that that really is how we've tried to do that evolution.

I love that. And it's super insightful on the kind of the team that got you here as well. So you talked about yourself kind of going through the kind of global financial crisis. I'm curious how you get your mindset through a recession or a crisis right now. Are there things that you do to kind of manage yourself through that, or are you just a classic entrepreneur that one day we think we're going to take over the world, the next day we think we're going to go bankrupt, that afternoon we think we're going to take over the world again? Is it just that as well?

Yeah. It's funny, as an entrepreneur, you kind of have to, like, take the emotional burden from six months from now and place it into the present moment. So, for instance, I felt a lot of anxiety, of course, the moment that I knew we were going to have to go through a reduction in force. And basically our operating plan coming into 2022 was going to be completely turned on its head. That's the moment that I got anxious. And it was while things were still going well publicly and in the economy and, you know, crypto hadn't crashed and all that stuff, layoffs hadn't been happening yet. But in my heart and strategically in my head, I knew what we were about to go through. So in some ways, I guess I've learned, and this is probably the entrepreneurial, you know, expectations management in me is that you or the entrepreneur or leaders will often face that emotional burden before the rest of the team. We have two choices. We can either face that with our support systems on our own time and mentally prepare for it, or we can do it in the moment. I would always prefer to do it in advance in a place where I can kind of let my mind go into a certain area. I actually spend a lot of time riding a bike and kind of thinking through these future scenarios where I'm literally burning off energy anyway and I'm able to take a little bit maybe of that negative energy, go through my own scenario planning that after years of experience, you can kind of start to predict how certain things might go. And really all that is an act of preparation. And I would just rather be mentally prepared for something because then I can emotionally handle it. If I'm not able to emotionally handle it, then I know that that has significant ripple effects out to the team. And so I guess I've built into my own preparation and work plan. How can I do that before it happens to anyone else so that when they're freaking out, I'm not.

So what do you do then specifically to help yourself mentally stay balanced with status?

Okay, yeah, first I guess I've done a lot of introspection, you know, years of therapy for many, any number of reasons as I would even encourage any entrepreneur to have yet to have an outlet. In my first entrepreneurial journey with glue, I didn't have that. And when you're going through these sorts of things, especially as an early stage entrepreneur, you're just, you just every day trying to get there, trying to do that thing that's going to make it work to the next stage. And then for me, that went away. You know, I was able to learn that there's life on the other side of your entrepreneurial experience. And for me that was really important because it meant that every decision that I made didn't need to be or feel so heavy. I just didn't want to feel that way again. And so again, that's why I really value the lesson of having to fail and wind down the business because it actually helps me emotionally now prepare for, I call it expectations management for kind of maintaining an even keel when things are great. It doesn't mean they're going to be great the next day, but it also doesn't mean that you're garbage trash. It just means that you have to kind of expect that in this journey there's going to be days, it's a wave, you know, there are certain days that are going to be great and wonderful and you should celebrate those. Absolutely. But it doesn't mean that there's a given that the next day is going to be the same.

Yeah, I agree with that. And I think it's interesting. Like it is the easy it's easy to be the smartest person in the room when the markets are going up for 13 years. It's. Yeah, it's hard to be this. It's hard to be the smartest person in the room when they capitulate, like. Right. And there is some. Some really good learning that comes out of that. So when, When. When you were raising cash, you've gone through a couple of different funding rounds. Anything that you've learned from that or that you could impost or impart to others about what to do well or what to do so that you can raise money or how to go through the emotions of being told no a million times as well.

Yeah, I'm going to give kind of a strategic, more mental answer, and then I'm actually going to give a tactical. It is still strategic, but it's something that's very tactical. The first thing is being really kind of keen on when to go from selling emotionally to selling financially. And there's a big difference between those two things often, and this is really being good at reading venture capitalists, is that they have to know or believe that they know what you're doing. You know, when. When you and I spoke about our business, hopefully you were able to kind of understand what that was with any two minutes or less. Yeah, that's really all that it takes. But if you were going to invest money in me, the very next questions will be, I want to see your balance sheet. And so, you know, it gets like, you have to be able to go from that emotional persuasion, like, right into, okay, and now here's the business case for it. And then also have those assets after the conversation to be able to send over so they know you're legit. So that leads to my next kind of strategy on fundraising.

Oh, yeah.

I'm going to. I'm going to say the strategy and also tell a story on how this mattered. So from the very first day or days of the company, I. Or we. I'll say we, because it is and was more than just myself. But we set up our file structure to be very easy for venture capitalists to do diligence on, meaning we saved every damn draft, every signed contract and label them as such. And the reason that that matters, and this is the story part, is because when especially you're in that early stage, you're fundraising. We started to raise our Series A in August of 2019, and we closed it on March 10th of 2020. Now, why that date matters is because seven days later, the world shut down with COVID if we had not had that money in the bank seven days later, there is no guarantee. And I was waiting for months. I knew the exact date that we were going to run out of cash. It was actually February 22, 2020. And so we had to take 100,000 load just to even get to that point. And so if. If we had waited, if there had been any delay, and that's where the delay could be, because your lawyers want to eat fees, there could be any number of reasons that. That your fundraising gets delayed. And if it gets delayed too late and in the wrong time frame, poop, your company's gone. So I would say being really intentional about how you set up your file structure to make sure that you've got essentially all of your signed documents, all of your financials, put it in a data room. That makes it super easy for the lawyers and the analysts to take a look at it. You're going to truncate the time that it takes to actually fundraise, and that can truly mean life or death for your business.

That's super interesting. There's a whole book on that as well.

You.

You wrote a book? Why did you write a book?

There was a time in life where I thought that I wanted to be an author. I love travel writing. I love travel. I love. There's a gentleman, a writer named Bill Bryson. Actually, he's my favorite travel writer. He. I just. I. I think he's brilliant in his ability to make you feel like you're right there, and I love that.

What's his book? A Walk in the woods or something?

Yeah, the Appalachian Trail one so good man. Yeah. The character development, the. The acts like. I mean, it's like you're. You're reading an encyclopedia while you're walking next to a guy who's having a trip, and it's like, wow. And so I. I wanted to adopt that style, but I wanted to adopt it in multiple spheres. And of course, being interested in business in general, it lent itself very well to me finding an individual. And of course, being a young person with nothing to lose. I told him when I read the draft of the book that he was writing, I told him something to the effect of, I think I can do it better. And that was the next nine months of my life is that I just wrote his book. His name is Ray Atia. The book called Fearless Frontline. It's pivotal in a lot of. So my thoughts. The focus of his business and his realm really was domestic manufacturing, where the focus is make sure that the frontline processes of your, your, your staff are so good and the feedback mechanisms are so good that you eliminate so much of the waste in your business. That is of course still applicable to this business. We are manufacturing insurance policies and insurance systems and underwriting basically. And so all of that stuff still applies and I'm extremely grateful to have had that opportunity. And it worked well.

I love it. I've always said, or I've heard the quote years ago that I like having a book written. I don't really like the process of writing it. I find it hard to. My sixth book comes out in January called the Second in Command and it's how to a Nice the Power of a CEO. Yeah, it comes out in January. It'll be, it'll probably be my biggest of all of the six that I've written so far. So I want to talk about your growth for a few minutes. You know, you've really gone through some great career transitions and growth. What are you focusing on today? Like you've got a company now with 100 billion that you've raised and you've got 100 plus employees now. And you know, we're in this strange time and you're in an exciting space going, you know, pre IPO as well. What are you focusing on in terms of your skill set as a leader?

Yeah, great question. First and foremost, it's actually continuing to let go of stuff that's probably not where you might thought that I was going to go. But my, my case in particular again, fortunately, because I had a financial background, I've never called myself our CFO because I've never wanted that title because I believe that there's people way better than me at that specific position. But for all intents and purposes, I've been our acting CFO since the beginning of the company. This is one of those moments where we're hiring someone where I can tell the right candidate and that individual you're going to be taking, you know, that this be this very solid but workable financial processes and systems that I built and I'm going to now hand it over to you to turn into an A plus. And so weirdly that's going to of course, you know, leave a lot of time for me, which is where I will most likely spend that time building back into the team. If I no longer have to occupy myself with a very functional and tactical position, then I'm going to go back into one of two areas. Long term strategy and setting up our organization to make sure that we can support it and then Building out the great team that we have. I would so much rather us take our existing group and just kick some ass than have to churn through a bunch of people. And I don't want to do all that bullshit. I really want to build a team that we have.

Dude, I'm doing my happy dance. I just launched a course recently called invest in your leaders. And it's all about growing the skill set of my team. And the more that I can grow the skills, like their coaching, delegation, time management project kind of identified these 12 core skills that managers need to be strong in. And the more that I grow their skills, the more I can get off my plate and delegate to them. I have a CEO recently said, why I can't give all these projects to my team, they don't have the skills to do it. I'm like, fuck, then grow them. Like grow their skills and delegate more. That seems to be the methodology to hear under as well, right? Delegate or grow people.

I think, I think you have to. But the reason that people are attracted to working at a startup is because whether they know it or not, they're going to get so much experience, so much vision into areas they don't know. But that actually is where I think that there's a very fertile ground to tap into. I know that we're kind of winding down, but this might be beneficial for your audience to hear. This is a program that we launched this year and it's. We just generically call it group leadership. Our group leadership program is between five and seven individuals and they all come from different place of the company. So this is not like individual, just siloed team basis. This is multiple people and it can even be multiple layers of title. But the sole focus is how do you want to get better as a professional. It's four weeks and in between each one of those weeks we have a specific homework assignment. I joke around about it because I don't want it to be too heavy, but it basically is taking it through a concept. Do take it through a concept, do take it through a concept, do graduate into now your formal role. And then we use our management teams, one on ones and their time to continue to kind of build into that. So we really just try to hypercharge in a very quick, you know, four weeks is an investment in time, but at the same time, like it's not finite. So it gives you a little bit of the basic skill sets. But then we continue to develop into you in that kind of, you know, get big while feeling small way.

I Love that. I think you're on the right track with all this stuff. All right, I want to go back, final question. I want to go back to the kind of the 21 or 22 year old Kevin Mackey. You know, it's 2007, you're just getting started in your career. What advice would you give yourself back then that you know to be true today, but you wish you'd known when you were just starting out? Yeah.

Be open to not knowing everything. You know, I kind of came into that 202007 or so timeframe probably with a false sense of confidence, which is a great thing for an entrepreneur. Like as a young entrepreneur, especially like you, you kind of have to be an idiot. And so like choose to, to, to get into it or let's say it differently because that's a little bit denigrating. You had to have probably maybe a false sense of confidence. Like you're an extreme sense of confidence in that. Yes, this is going to be tough. Yes. I don't know what the outcome is, but I'm still going to do it and I'm going to do it every day and I'm probably not going to do it very well. So that's where I would say be okay that you're not going to know everything, but be open to letting that come in and then really just kind of being introspective to say like what actually did matter and what didn't. Just get rid of the shit that doesn't matter and really focus on the things that matter to you and develop that into your own approach.

I Love that. Kevin McKay, thank you very much. The CEO for Coterie Insurance. Really appreciate the time sharing with us on the second planet. This is actually truly life changing stuff. You're facing fears, you're overcoming challenges and that's what appealed to me. My life got changed when I went through this program. When you lift off the ground and you're sitting in that seat by yourself and you're flying over, over whatever you want to fly over and seeing whatever you want to see, it just puts a new perspective on everything.