Ep. 243 – Coterie Insurance COO, Kevin Mackey

Our guest today is Coterie Insurance’s COO, Kevin Mackey.

Kevin Mackey 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 as 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 Cintrifuse, a public/private partnership with an active network of venture capitalists, big corporations, and tech startups. In between startup experiences, Kevin ghost wrote, “The Fearless Front Line”, which is a book about organizational and leadership design.

Kevin currently splits his time between Chicago and Cincinnati.


In This Conversation We Discuss:

  • What benchmarks make a business with a high sale value
  • What the insurtech industry is and how it affects the insurance industry
  • How to keep the confidence of your employees during difficult times in business
  • How Kevin self-manages through a recession/crisis
  • Best strategies when it comes to fundraising



Connect with Kevin Mackey: LinkedIn

Coterie Insurance – https://coterieinsurance.com

Connect with Cameron: Website | LinkedIn

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Our guest is Coterie Insurance‘s COO, Kevin Mackey. He 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, he taps 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 several years at Cintrifuse, a private-public partnership with an active network of venture capitalists, big corporations, and tech startups. In between startup experiences, Kevin ghost-wrote the Fearless Front Line, which is a book about organizational and leadership design. He splits his time between Chicago and Cincinnati. Kevin, I’m looking forward to chatting with you. Thanks for joining us. 

Thanks. I appreciate it.

You have had an interesting journey in terms of the entrepreneurial side of things and working on the VC side of things. Why don’t you walk us through some of your bios and how you got here, and we will dive into some of the specifics with you? How did you get into the role that you are in and even in co-founding and COO with Coterie? 

It does start as that buy-side equity researcher. I graduated from the University of Dayton, which has a pretty solid program. It’s called the Davis Center for Portfolio Management. In college, I was able to get access to Bloomberg terminals. I fell in love with analyzing businesses. That’s where I started my career at the beginning of the Great Recession. I graduated in December 2007 with a degree in Finance and Accounting. I got my first job in January 2008. A few months later, on March 17th, 2008, Bear Stearns collapsed. I’m reading all this stuff and realizing, “I don’t know anything.”

From that perspective, I began to teach myself how to learn. I graduated undergrad, but that was the moment when I realized there was so much more to learn, and I fell in love with it. It was such a fertile time to learn things that were going on in finance and business in general. For the next couple of years, I immersed myself in the financial blogosphere, whether it was seeking Alpha or any of these other websites. It was getting started. I fell in love with that piece, but I also realized I didn’t want to go into financial services. I wasn’t going to be an investment banker.

I had the fortunate benefit of knowing a professor at Northern Kentucky University here in the Cincinnati area. She and I ended up starting and founding the company Glue. It was a serendipitous opportunity. I was young. I didn’t have children at the time. I could take one of those swings, but I didn’t know anything.

In hindsight, I didn’t have any idea what I was doing, but as a first-time founder, you are feeling your way through everything. That was the foundation for a lot of the beliefs I have in terms of founding subsequent businesses, founding Coterie, building our operations up from nothing to more than over 100 employees all over the country, and selling millions of dollars every month.

In terms of scaling out these organizations and building multiple companies, have you had exits with these companies? Have you built and sold? What does that lifeline look like?

There are no exits. I would say the opposite. I had to shut down Glue. In some respects, I know that we are going to be going for a healthy exit here with Coterie. That’s not the exact purpose of why we are building Coterie, but we believe that’s going to be a good opportunity for us. In some ways, I’m glad to have learned what it is to wind down a business not only logistically but also the emotion that goes into it. You are dealing with other people’s money and the tail end of all that optimism that you have when you begin to start a company. I value that I had that opportunity, especially since I’m young in my career. I was able to feel visceral what it feels like to get it wrong. That’s the foundation for what it takes to get it right.

That’s intriguing. We are going to go in there. We are going to talk a little bit about the rollercoaster of emotions and also the lessons to pass on. It’s funny you mentioned Bear Stearns. My old roommate in college was the Head of Derivatives Worldwide for Bear Stearns at the crash. He wrote the book called Bear-Trap. It is about the crash of Bear Stearns and why it fell apart. 

In the book, he mentioned that Lehman Brothers was going to crash next. The book Bear-Trap came out about two weeks before Lehman Brothers crashed. I’m like, “How did you know?” He goes, “We all knew. Everybody in the industry knew it was a house of cards.” Something interesting for you at the timeline of your career was to be in high school during the crash of the Nasdaq 2000 and 2001 crash and start your business at the beginning of the global financial crisis. Do you find that has given you a foundation for a little bit more realism and a little bit more cautiously opportunistic versus the irrational exuberance we have seen? 

That’s possible. I have looked at the stock market increases from 2012 to 2021, give or take. I’m a technical analyst. I love to read charts. For me, these charts are crazy. How long can you go on the high end of your charts? From that perspective, I’d always taken the approach that there is only so much energy that a certain market can take before that energy has to go in a different direction. It was a little bit of pragmatism in terms of looking at what could happen in full admission.

Early in my career as a financial analyst, I was a bit of what you would call a doom and gloomer. I went through the phases of fiat currency. Are we in deep trouble because of fiat currency? There are elements of truth to a lot of those things. What I saw through that 2008, 2009, and 2010 timeframe, at least for a decade or so, is that there was complete unwillingness for our government. This is not a political statement. 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 realize that there was a bit there. That was outside of finance. I’m going to get a little bit into the financing stuff, and we will take it back, but the idea of credit default swaps coming out of Lehman Brothers failure, I remember studying that. People were like, “How is this even mathematically going to be possible? And at the same time, it persisted.” In some cases, even with AIG and others, we made money on it.

All of those learnings helped me go to a place where it’s like, “What is the market? For those supporting the market, what are they willing to do? What can they do?” Not to get far down that route, but we have used it a lot. You can only spend trillions of dollars a couple of times before you end up incurring other things. Having seen that early in my career was helpful in knowing that because money comes in at certain times, it doesn’t mean it’s always going to be there.

Sorry for the long-winded response, but it does show up in our business now, and I will turn it back over to you. The markets have fundamentally changed for fundraisers, and especially venture-backed businesses like ourselves, over the past several months. In particular, we are in insurtech. There are a lot of insurtech companies that have gone public and lost people a lot of money.

In early 2022, we went from a place where we have always been fortunate and had a solid balance sheet and been able to raise money, but that money is not a given. We didn’t have to have a lot of conversations with our board for our management team and our founders to understand that. That’s where some of that early career experience shows up in the current business.

I’m with you on the market, and everything has changed. You got to be completely moronic to think it hasn’t, considering all the signals we are hearing from bigger companies. How are you managing some of the employees? Are you talking to the employees about what they are seeing in the news and what they are reading? They are reading it too. How do you calm them and make them realize, “We are okay and solid, and here’s what we are planning on?” I’m asking a crazy question that none of us know. How long do you think this is that we are going to have to ride out this period of recession/inflation?

How are we talking about this with our team? It comes down to what I say internally as business acumen. That’s probably not the most marketing-friendly terminology, but for us, especially with our less experienced professionals, we have to educate them. You can’t understand what’s happening and even the decisions we are making as a business unless you understand what our business is and what those macroeconomic factors are. Otherwise, it’s going to be a series of decisions you don’t know, and you are relying on trust.

SIC 243| Coterie Insurance

Coterie Insurance: You can’t understand what’s happening and the decisions that we’re making as a business. Unless you understand what our business is and what those macroeconomic factors are.


Does the team trust that you know what you are doing and what you are talking about? When you don’t have an answer to that, people may fill in their gaps. It does start with good organizational hygiene. It is taking this lens of I’m educating. I’m an educator of our team every single day. I have to say this is my lens of this education.

You started off the question. We don’t know what’s going to happen, but I have to tell you why we have made the decisions we have made and what that is going to do for us. In the case of our business, fortunately, we do have a strong balance sheet. We have been to a reduction in the year, which put us in a position to raise more money and strengthen our balance sheet to get through this whatever timeframe. That’s the second part of the question. How long do we expect this to last?

The benefit of having gone through at least one of these “black swan events” is I remember thinking viscerally of going to a mall in the Cincinnati area. It doesn’t feel like a recession. I remember thinking that because the recession hit different folks at different times. When you have 30,000 people that lose their jobs 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.

This isn’t a secret, and it’s even well-documented. Most tech companies are going through layoffs and cost reduction measures because we are finally getting back to a place where business and unit economics matter. I appreciate this whole thing being a cycle of economics going down, less money to be able to spend, and people probably going through their personal or business defaults. Banks go through their cycle of having to close up lending.

That whole cycle can probably take about two years. For us and our business, because we are servicing small business owners. Financially, we have shored up our balance sheet to the point where we can operate successfully for the next couple of years. We want to hit that hard because we know that these are the times when small businesses start. We will be able to hopefully get customers for a long time if we are able to get them at the inception of their businesses. We do look at it as opportunistic.

I love that you guys were smart enough about shoring up the balance sheet and doing the reduction of force. I love the fact you even talked about educating the team and making sure they understand. Too often, companies are like, “They won’t understand the balance sheet and P&L. We will ignore it.” That’s stupid. Give it to them in the basics. You can teach them a basic understanding of the economics of our business, assets and liabilities, and cashflow. They go, “Okay, I understand.” 

Even that basic understanding doesn’t build enough of an education, they are going to be able to do much, but it certainly builds trust from them that you care about them. You have dispelled a bunch of the rumors they are running around and chatting about that are grounded in the fact that no one cared enough to talk to them. You are smart in doing it that way. 

You mentioned that you had worked on the buy side in the VC space and did a lot of the analysis. A lot of our members and companies out there are looking to exit their organizations and sell their companies. Did you learn anything on the buy side that if it’s somebody wants to build a company for the best possible exit, what are the things you saw in the analysis that make a company look better than not? 

I’m going to respond for myself, and I will get into the analyst’s answer. 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, what you are talking about, whether it’s an exit, IPO, strategic merger, or acquisition, it should be because you are on the offensive. You know where you want to go. You are selecting the right fundraising source for your next round of growth.

Certain businesses lend themselves better to certain financing structures, whether they will be like, “We are going to franchise as our way of funding our scale versus going the IPO route.” It’s important for your business to decide which one. For us at Coterie, franchising makes no sense. It’s not even remotely part of our business model. That only leaves a couple of different avenues that are realistically outside of the sustainable growth that would get us to that next stage.

It’s important for us to know that about our company on the front end. I’m going to go a little bit more into the analyst piece of this. I’m going to talk about my industry. In particular, when I say my industry, I’m going to talk about insurtech, as it has been called. Insurtech, being Lemonade, Root, Metromile, and Hippo. Those are the four that primarily went public in this realm between the 2020 timeframe.

It’s important to realize what they went through because a lot of them, on paper, have made money and lost money for investors. If you are in this industry, particularly in insurtech, on unit economics. We have to demonstrate that we can write business profitably. That’s what happened in what we will refer to as Insurtech 1.0. No offense to anybody, but with the insurtechs that had grown in venture capital a couple of years before us and went that IPO route, they went with the impetus of growth is the first thing that matters.

What the markets have told us over the past several months is that it was great, but you have to make money for that to sustain. We know that now. Going into whether it’s an IPO, a merger, or an acquisition, 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 processes. As an operator, we have that golden ticket and the visibility into the future of how we need to operate now to get there.

That’s how I look at both of those things. It’s not a given that we are writing small business insurance. We are fortunate to have wonderful underwriters and smart people who build the digitization of our underwriting. At the end of the day, if something goes wrong or you have a catastrophe you are expecting, you can be in a different circumstance.

Building that into our business before we go into a massive scale is part of that answer key. It also means that maybe we have to give ourselves. This is now an example. We might need to give ourselves several more months to IPO because we know that, in several more months, we will have a renewal cycle under our belt. Knowing that is a strategic decision, not a race to get to IPO.

You rattled off other businesses that are in the insurtech space. Can you explain to us what the insurtech space is? Tell us what Coterie does and who your typical clients are, and we will go into some more questions. I’d never heard of any of those brands. I would imagine a lot of our readers don’t. For you, it’s like, “We know them.”

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. Insurance is a funny industry to be in because I’m a new newcomer to insurance. I have been the COO of an insurance company for several years. Before that, I was a consumer of insurance as a small business owner.

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, right for disruption. Let’s say you are my agent. You give me something. It could be digital or a piece of paper, but you are giving me something, and I’m giving it back to you. You are giving it back to someone else. They are giving it back to you. You are coming back to me. You see, in a bifurcated way, how that can add up to be a lot of time, confusion, and headaches. 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 purchased, you don’t know why it costs what it did, you don’t know how to use it, and yet you do it every single year, and you are required to do it.

In a lot of ways, the insurtech industry is taking all these old processes that require a lot of what I would call fixed costs, AKA you are employing a lot of people to do a lot of stuff, and we are able to completely reverse that. That’s the idea of insurtech. You are taking the insurance industry and all the components, compliance requirements, and everything associated with it. You are digitizing all of it. You are doing in a particular industry for a particular market. Our market, 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.

SIC 243| Coterie Insurance

Coterie Insurance: That’s the idea of InsureTech. 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.


Here’s a use case for that. Intuit QuickBooks. I do like to joke around, but it’s not a joke. As a small business owner, I know that unless you are actively trying to commit fraud, you don’t lie to your books. You are only screwing yourself if you lie to your accounting books. From an underwriting perspective, that’s a gold mine of information because instead of I’m giving you this piece of paper and guessing how much revenue, we suck the information in and use the algorithms to take a process that could take, at best, hours, days, or weeks. We are able to underwrite your business in two seconds.

My favorite story behind this, and I will share this with you and turn it back over. Intuit is one of our partners. For the first policy that we bound with Intuit, the person, the business owner, contacts our customer service line, and we should have this written down and etched somewhere in our office. They had said, “I wanted to know if the policy was bound because it was easy.” No one believed that it could be that simple, and all we are doing is not that easy, but we are mirroring these small businesses’ data back to them.

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. He took that software, flipped it upside down, and taught businesses how to build their P&L properly. When they went to a bank, the banks would fund them. I’m like, “It’s genius.” That’s all you have done is figure out the most efficient model to get the information to fund and bind it in a way that makes so much sense. I get it. I love the model. You have gone through a couple of rounds of funding. How much have you raised? 

In total, it’s over $100 million. We went through another round. Pardon me for not remembering the absolute dollar amount, but it’s a little shade over $100 million.

You raised about $100 million. It’s a solid proof of concept, especially since you are only at 100 employees. How has that changed the organization? 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? 

It’s something a lot of people reading this show up to work every day to figure out. It’s not that easy, especially as a national and remote organization. It’s one of the things we have to try and be as intentional as possible about. I will tell you a little bit about what we have gone through and some lessons I have learned that we hope to apply now on an ongoing basis.

The first question is, how can we handle the scale? This is not rocket science. A lot of people talk about how you grow from different and how it goes from everything being personal to all of a sudden your job has shifted maybe dramatically, and the way and the people that you have shown up to work with has fundamentally changed.

That can be extremely difficult for some of your early employees. You are spending a lot of time trying to get your new employees who have you recruited for the current moment to the same place as your old employees who have given everything for the company and to be what they are. You have to go from this place where you are scaling yourself. I call it getting big while feeling small. We have to get big while still having this personal connection. This might sound hokey, but the best way I have figured out is truly to lead by example.

If I want to make sure that all the employees I will never have time to have a one-on-one with and want them to have the same experience that my employees get, I have to show up with the same energy and intention in every single one of my one-on-ones and team meetings. That is my responsibility because, for the first few years of the company, I was doing all of the work. I’m not saying that to be haughty or like I did the world’s best job. I like to recruit by saying, “I want you to take my C-plus work and turn it into an A-plus.” I had to do a whole bunch of C-pluses to get it up.

That flipped for me where I went from the person doing so much to recruiting the people replacing me to running an organization that doesn’t need me anymore. That is, by design, how we have tried our best they won’t feel small is to make sure there’s still that personal approach, our culture still shines, and I’m still always available, but now my team members should be front and center. Our front and center in most of the work is how we have tried to do that evolution.

SIC 243| Coterie Insurance

Coterie Insurance: How actually we’ve tried our best to get the big wall feeling small is to make sure that there’s still that personal approach. Make sure that our culture still shines, and make sure that we’re still always available.


You talked about yourself going through the global financial crisis. I’m curious how you get your mindset through a recession or a crisis now. Are there things that you do to manage yourself through that? Are you a classic entrepreneur who one day thinks we are going to take over the world, the next day thinks we are going to go bankrupt, and that afternoon, thinks we are going to take over the world again? Is it that as well? 

As an entrepreneur, you have to take the emotional burden from several months from now and place it into the present moment. For instance, I felt a lot of anxiety the moment I knew we were going to have to go through a reduction in force and 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 in the economy, crypto hadn’t crashed, and layoffs hadn’t been happening yet. In my heart and strategically in my head, I knew what we were about to go through.

In some ways, I have learned, and this is the entrepreneurial expectations management in me, that you, the entrepreneur or leaders, will often face that emotional burden before the rest of the team. We have two choices. We can 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 let my mind go into a certain area.

I spend a lot of time riding a bike and thinking through these future scenarios where I’m burning off energy anyway. I’m able to take a little bit of that negative energy and go through my scenario planning. After years of experience, you can start to predict how certain things might go. All that is an act of preparation. I would rather be mentally prepared for something because I can emotionally handle it. If I’m not able to handle it emotionally, I know that has significant ripple effects on the team. I have built into my own preparation and work plan. How can I do that before it happens to anyone else? When they are freaking out, I’m not.

What do you do specifically to help yourself mentally stay balanced? 

I have done a lot of introspection and years of therapy for a number of reasons. I would encourage any entrepreneur to have yet to have an outlet. In my first entrepreneurial journey with Glue, I didn’t have that. When you are going through these sorts of things, especially as an early-stage entrepreneur, you are every day trying to get there and do that thing that’s going to make it work to the next stage. For me, that went away. I was able to learn that there’s life on the other side of your entrepreneurial experience.

That was important because it meant that every decision I made didn’t need to be or feel heavy. I didn’t want to feel that way again. That’s why I value the lesson of having to fail and wind down the business because it helped me emotionally prepare for expectations management. When things are great, it doesn’t mean they are going to be great the next day, but it also doesn’t mean that you are garbage trash. It means you have to expect that in this journey. It’s a wave. There are certain days that are going to be great, and you should celebrate those. It doesn’t mean there’s a given that the next day is going to be the same.

It’s easy to be the smartest person in the room when the markets are going up for several years. It’s hard to be the smartest person in the room when they capitulate like crap. There is some good learning that comes out of that. When you were raising cash, you’d gone through a couple of different funding rounds. Anything you have learned from that, or could you impart to others about what to do well or what to do so that you can raise money or go through the emotions of being told no a million times? 

I’m going to give a strategic mental answer. It’s still strategic, but it’s something tactical. The first thing is being keen on when to go from selling emotionally to selling financially. There’s a big difference between those two things. This is being good at reading venture capitalists. They have to know or believe they know what you are doing.

When you and I spoke about our business, hopefully, you were able to understand what that was within two minutes or less. That’s all that it takes. If you were going to invest money in me, the next question would be, I want to see your balance sheet. You have to be able to go from that emotional persuasion into like, “Here’s the business case for it.” Have those assets after the conversation to send over so they know you are legit. That leads to my next strategy for fundraising.

I’m going to say the strategy and tell a story on how this mattered. From the first day or days at the company, we set up our file structure to be easy for venture capitalists to do diligence on. We saved every draft, signed contract, and labeled them as such. The reason that matters and this is the story part, is because, especially since you are in that early stage, we started to raise our Series A in August of 2019. We closed it on March 10, 2020.

Why that date matters is because several days later, the world shut down with COVID. If we did not have that money in the bank several days later, there’s no guarantee. I was waiting for months. I knew the exact date that we were going to run out of cash. It was February 22nd, 2020. We even got a $100,000 loan to get to that point.

If we had waited and there had been any delay, and that’s where the delay could be because your lawyers want to get fees, there could be any number of reasons that your fundraising gets delayed. If it gets delayed late and in the wrong timeframe, your company is gone. Being intentional about how you set up your file structure to make sure you have all of your signed documents and all of your financials to put in a data room that makes it easy for the lawyers and analysts to take a look at it. You are going to truncate the time that it takes to fundraise. That can mean life or death for your business.

There’s a whole book on that. You wrote a book. Why did you write a book? 

There was a time in my life when I thought I wanted to be an author. I love travel writing. There’s a gentleman, a writer named Bill Bryson. He’s my favorite travel writer. He’s brilliant in his ability to make you feel like you are right there.

What’s his book, A Walk in the Woods

Yes, and The Appalachian Trail. It’s like you are reading an encyclopedia while you are walking next to a guy who’s having a trip. I wanted to adopt that style, but I wanted to adopt it in multiple spheres. Being interested in business lent itself well to me finding an individual and being a young person with nothing to lose. 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.

For the next several months of my life, I ghost-wrote Ray Attiyah. The book is called Fearless Front Line. It’s pivotal. The focus of his business and realm was domestic manufacturing, where the focus was to make sure that the frontline processes of your staff were good. The feedback mechanisms are good that you eliminate so much of the waste in your business. That is still applicable to this business. We are manufacturing insurance policies, insurance systems, and underwriting. All of that stuff still applies. I’m extremely grateful to have had that opportunity, and it worked out well.

SIC 243| Coterie Insurance

Coterie Insurance: Make sure that the frontline processes of your staff are so good, and the feedback mechanisms are so good that you eliminate so much of the waste in your business.


I heard a quote years ago. It was like, “I like having a book written. I don’t like the process of writing it.” My sixth book comes out in January 2023. It is called The Second in Command. It’s how to unleash the Power of a COO. It will probably be the biggest of all of the six I have written. I want to talk about your growth. You have gone through some great career transitions and growth. What are you focusing on now? You have got a company now with $100 million that you have raised, and you have got 100 plus employees now. We are in this strange time and exciting space going pre-IPO. What are you focusing on in terms of your skillset as a leader? 

It’s continuing to let go of stuff. That’s not where you might think I was going to go. I had a financial background. I have never called myself our CFO. I have never wanted that title because I believe that there are people way better than me at that specific position. For all intents and purposes, I have been our acting CFO since the beginning of the company. This is one of those moments where we are hiring someone where I can tell the right candidate. That individual is going to be taking these solid but workable financial processes and systems I have built. I’m going to hand it over to you to turn it into an A-plus.

Weirdly, that’s going to 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 functional and tactical position, I’m going to go back into one of two areas. Long-term strategy and setting up our organization to make sure we can support it and build out the great team we have. I would rather us take our existing group and kick some ass than have to churn through a bunch of people. I don’t want to do all that BS. I want to build the team we have.

I’m doing my happy dance. I launched a course called Invest in Your Leaders. It’s all about growing the skillset of my team, their coaching, delegation, and time management, and identifying these twelve core skills that managers need to be strong in. The more I grow their skills, the more I can get off my plate and delegate to them. I had a CEO say, “I can’t give all these projects to my team. They don’t have the skills to do it.” I’m like, “Grow their skills and delegate more.” That seems to be the methodology that you are under. It is to delegate more and grow people. 

You have to, but the reason that people are attracted to working at a startup is because, whether they know it or not, they are going to get so much experience and vision into areas they don’t know. That is where there’s a fertile ground to tap into. There is a program that we launched in 2022. We generically call it group leadership.

Our group leadership program is between 5 and 7 individuals. They all come from different places in the company. This is not like an individual siloed team basis. This is multiple people. It can even be multiple layers of title, but the sole focus is how you want to get better as a professional. It’s four weeks. 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 heavy.

It is taking it through a concept, do. Graduate into your former role. We use our management teams’ one-on-ones and their time to continue to build into that. We try to hypercharge. Four weeks is an investment in time, but at the same time, it’s not finite. It gives you a little bit of the basic skillsets that we can continue to develop into and get big wall feeling small way.

Final question. I want to go back to the 21 or 22-year-old Kevin Mackey. It’s 2007. You are getting started in your career. What advice would you give yourself back then that you know to be true now but you wish you’d known when you were starting? 

Be open to not knowing everything. I came into that 2007 timeframe with a false sense of confidence, which is a great thing for an entrepreneur. As a young entrepreneur, you have to be an idiot. Choose to get into it differently because that’s a little bit denigrating. You have to have a false sense of confidence or an extreme sense of confidence. You are like, “This is going to be tough. 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. I’m not going to do it well.” Be okay that you are not going to know everything but be open to letting that come in and being introspective to say what did matter and what didn’t. Get rid of the crap that doesn’t matter, and focus on the things that matter to you and develop that into your approach.

Kevin Mackey, thank you very much, the COO for Coterie Insurance. I appreciate the time you spent sharing with us on the show.

Thanks so much.

I appreciate it.

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