David McFarland On Raising $75 Million To Simplify Small Business Insurance

David McFarland has raised tens of millions of dollars to improve the insurance industry, and in turn, empower brokers and their small business customers to survive and thrive. His venture, Coterie Insurance has attracted funding from top-tier investors like Weatherford Capital, Alpha Edison, Group 1001, and RPM Ventures.

In this episode, you will learn:

• Fundraising, and how it changes by round
• Hiring and growing your team
• The future of insurance for small businesses

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For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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About David McFarland:

David is the Founder and CEO of Coterie, a US-based insurtech focused on making risk transfer efficient for the small commercial P&C insurance space. Coterie uses industry-leading tech, deep insurance expertise, and product innovation to embed insurance into their partners’ existing products and workflows, leveraging data from multiple sources to turn small commercial accounts from an unprofitable obligation to a profitable opportunity. Coterie currently works with a variety of small business tools including accounting, payment processing, lending, and payroll companies, as well as agent and broker channels.

Immediately prior to founding Coterie, David was Chief Actuary and Head of Insurance Product & Pricing at Clearcover, a personal auto insurtech in Chicago. Before Clearcover, David worked in the insurance space with a variety of products in personal and commercial lines. David is a Fellow in the Casualty Actuarial Society and a Member of the American Academy of Actuaries.

We are thrilled that David recently announced the successful close of the company’s $50 million Series B round, led by Weatherford Capital and with participation from Frontier Venture Capital and previous investors, RPM Ventures, Intact Ventures, Group 1001, and Alpha Edison.

Connect with David McFarland:

• Crunchbase
• LinkedIn

Read the Full Transcript of the Interview Here:

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Alejandro: Alrighty hello everyone and welcome to the deal maker show. So super excited about the guest that we have today. We’re gonna be talking a lot about building scaling financing changing from 1 state to another. Things about fundraising that maybe were taking longer than expected I mean I think that we’re gonna be learning everything in between but I guess without further ado. Let’s welcome our guest today David Mcfarlane welcome to the show.

David McFarland: Thanks El Huntra good to be here.

Alejandro: So let’s do a little bit of a walkthrough memory lane David so originally from south of Florida but you did move quite a little bit especially when you were 15 so give us a walk through memory lane on how were your upbringings. So.

David McFarland: Yeah, yeah, I grew up down in Fort Lauderdale and had ah had a pretty great experience down there. It was it was interesting to grow up in a pretty diverse environment and then I subsequently moved to Columbus Georgia which was. Lacking in diversity. Let’s say. But even so it was it was a neat experience with there for high school and college I learned a lot ended up back in Boker Aton Florida and met my wife there and then we’ve we’ve been to a few places since then.

Alejandro: So nice. So when you were 15 You moved to Georgia as you were saying and I think that that’s the time where you really got present to the law for math. So how did that come about.

David McFarland: Yeah, yeah, I actually resisted that love for a little while but it but it kept kind of chasing me down so when I was when I was in high school I had a natural act for it and then I focused on. A lot of things I think everyone else focuses on when they’re in college you know, goofing around partying all that kind of stuff so really geared my studies more toward what I found mildly interesting like history and whatnot. But one day I reluctantly took a math class in formal logic actually and. I realized that I had ah ah just a huge passion for problem solving and I asked the teacher. What I had to do to do this every day for the rest of my life and he was like you either either become a mathematician or a lawyer and I did not want to go to law school I was ready to be done with schools I was like I’m I’m gonna be a mathematician. So the next day I went to the registrar in my junior year of of college and they basically said like look we do not recommend doing this, you are going to have to take 24 hours every single semester in order to to do this if you want to graduate in time I kept pushing. And they put me on the actuarial track so that I could graduate at least in some semblance of a reasonable amount of time I didn’t know what that word meant but I did it and the next semester you know I loaded up with like 24 hours much math classes and then ah someone. Girl in one of my math classes asked me if I was taking the actuarial exams and of course me being a young dumb easily s sued individual I said absolutely I am and then I that’s pretty much how I became an actuary.

Alejandro: Nice now in your case you know for the people that are listening what does being an actuary means what is that.

David McFarland: Yes, so Actuaries are usually found in the insurance phase and I’m making them sound like a exotic species which they are. They’re they’re They’re a little lot. We we collect calculators for some reason but.

Alejandro: Ah.

David McFarland: Essentially and we use quantitative analyses to quantify risk right? So we use all kinds of models and data to figure out how we can price risk how we can quantify and what I relate this to is Basically. Insurance or risk is is associated with like unwanted volatility right? And what we can do as actuates is we can quantify the impacts of that volatility and say if you don’t want that volatilityility anymore you can pay me to essentially transfer it and that transferring of the volatility of. And when things are balancing up and down to a study state is is what insurance is insurance is just a transfer of risk and you need someone who’s actually going to price that transfer of risk and Actuaries do that Particularly well.

Alejandro: So Thank you for that I’m sure that a lot of people are gonna be able to really now get an understanding for that. But in your case you know it was very interesting because you did a little of the corporate route and then from there you switched to the consulting Route. So How was that. Kind of like transition of events. You know, working out there. So.

David McFarland: Yeah,, That’s a great question So I started off at the National council on compensation insurance which is kind of one of the the top insurance entities in the workshop space and what they do is they collect all kinds of data From. All the insurance companies in like 40 of the 50 states and then they provide guidance on how to how to price things you have all kinds of stuff I had the task I don’t think anyone at the company wanted of legislative pricing and analysis which basically when legislature wanted to. Change something in that state regarding workers comp they would write it all up and send it to nccci and say how is this going to impact my state. It’s going to lower where comp costka increase. What? what’s gonna happen and so that would end up on my desk and I go through it find the changes then I. To Pull all kinds of data and figure out this is like a big hairy math problem of how this is actually going to impact that particular State. So There was really no template of how to do this Sometimes there was like there were these automatic changes which happened but generally it was a very. Kind of entrepreneurial problem right? like something that hadn’t been done before you had to be innovative to do it and I love that I Absolutely love doing that and I I was I kind of felt like a consultant as I did that and things that things went well at NCci and they you know they wanted to progress Beyond. What I was doing and when that came up when the opportunity to continue to to grow in the company came up I I was reluctant to do the other things. The kind of cog and the wheel corporate type things and so I I started searching for a job as a consultant. And found something that was a you know boutique firm where I could help out various insurance companies and do some innovative stuff and that’s when I shift it over to the consultancy side.

Alejandro: Now How do you land from the basically the consulting side of things to all of a sudden you go back to being recruited by a firm and then is like okay you know now we go into Startup World. So What was that. Process of entering startup land. What what did that look like so.

David McFarland: Yeah, so while I was doing consulting I got to have some great experiences and an insurance company reached out and was really interested in building out some cool stuff on the embedded insurance space specifically in the jewelry insurance space. And that that idea of doing something novel and insurance and building a team around it was was really alluring to me so I joined up with jewelers mutual to do that and we saw some amazing results just fantastic premium growth. Great expense ratios and we got to really change how insurance was done. By meeting people right in the shopping cart and doing some some really fascinating stuff there and through that experience while at jewel mutual I got connected to the Vc world and really was it was a smaller Vc group in the midwest as well as other corporate venturetra capital groups and. Through that I got connected to Kyle Makazucchi who’s the founder of clearcover and he reached out while he was considering the idea of buildinging up clearcover and we had some similar ideas on how insurance should be done and he asked me if I’d be interested. Helping start that via being their chief actuary and head of insurance product.

Alejandro: So Then how do you go from from that to actually starting your own thing I mean I’m sure that you know it was very interesting for you. You know you were you were in this case, you know for for clear Cover. You were recruited as the second employee. So I think that this at least gave you the opportunity to really see how a company gets started and how is built over the course of time I mean what do you think?? what kind of insight. Do you think that gave you to be at ease and to really know that they that that you had a clear grasp as to how you could do it.

David McFarland: It was immensely helpful and Kyle gets a lot of the the praise and that I told him from the beginning that I was interested in starting my own company with it and not only was he mean amenable to that idea.

Alejandro: Ah, your own.

David McFarland: He was supportive of my professional development while I was a clear cover. He went with him to to pitch went with him while I was responsible for the the reinsurance and the insurance side of things and and having that exposure to what the founders go through. And obviously it’s not 1 to one like I’m not getting the full experience right? That’s that’s that’s his baby. He’s he’s the one lose and sleep at night. All those types of things but still having that exposure gave me a lot more confidence to to go out and start you know. Calling people it built the network as well. So I had more confidence in in reaching out to vcs it. It helped a lot I was very thankful for it.

Alejandro: Now at what point do you realize? it’s time is your time.

David McFarland: That that’s a great question I have kind of an underlying philosophy with that and I don’t know if it’s right? So I don’t even call it philosophy. It’s like kind of an idea. Um, but I feel like like sometimes if you like. Try and get greedy and grasp things before the time’s right, like they they have a tendency to like fly away but simultaneously you can’t just expect things to fall into your lap. So. There’s this kind of a balance and it’s It’s tough to describe like when the right time is but sometimes you just know sometimes it’s like things are set up. You’re like no now is the time to to go out and do it um, but you I mean you’ve been there before you know like some things. It’s like if you get too hasty with it. It’s like it just goes away and it doesn’t happen. Ah, there was a time at clear cover of it. You know about a year and a half in where things just started aligning and it was almost like like it was going so well at clearcover that a part of me was like what why would you leave this really good thing like like. Going off like a rocket ship. You’re in a great position. It would be dumb right? A lot of people would say oh I’d be dumb to take such a risk and go start this other thing and this rising discomfort in me combined with all the things kind of lying up to where no starting this thing. It may be a good idea. Those 2 things working together where was like almost a reluctance and a nervousness and anxiety a fear to do it but also having the opportunity in front of you when those 2 things came together was like no I need to do this I need to overcome my fear and just just go and and do it regardless of the risk. And that maybe that’s when it’s time to ah to do it when the fear is there and the opportunity. Yeah.

Alejandro: I mean as they say with fear there’s growth right? So so good stuff now now in this case for you. It was a a pretty interesting moment in time too because you were a father already. You had 2 2 2 little ones and you had a third one on the way.

David McFarland: Yeah.

Alejandro: So I mean a lot of people would probably think that you’re going nuts for like leaving you know the the paycheck you know and and and going at it and taking the leap of faith. So so how how was that I guess conversation with your wife to really get a line.

David McFarland: Yeah, thankfully I think I have the world’s most supportive life. She’s she’s been super understanding of you know me taking her across the country and going from oneding to another. But yeah, we had. We had 2 kids at the time I four now and when. We were doing the transition from clear cover to cotery. We were pregnant with our third and specifically when we were moving from Chicago to Cincinnati she was in her third trimester with with the third child and. Thankfully that conversation went well. She’s always been one of these people she doesn’t complain. She she supports me she understood the risk. She’s a she’s got a masters degree in economics. She’s another quantitative person understands risk all that kind stuff. Ah, but you know if it wasn’t for her and. Support that I have the lack of anxiety that I have with her and just like her willingness to follow me I I would not be able to do what I do what I do I don’t I can’t imagine how people are able to take on the burdens associated with starting the company and like have a volatile home life. Fighting 2 fronts would be that’s stronger than I am that that’s really difficult.

Alejandro: Ah, ah, hundred percent now now for you and when you finally decided to go for it the fundraising I mean it. It. It took a little bit of ah of ah you know it was ups and downs in a little bit more. Challenging or I would say full of action that what you would have hoped and in fact, you signed the term sheet the day before your son. Your third son was born I mean that sound would say full of action action packed for sure. So so what happened there.

David McFarland: Yeah, yeah, so I with the fundraising environment things were going well I was in Chicago and I met some and potential investors and they were really in it. Loved what we were doing loved the idea of bringing speed simplicity and service to commercial insurance and specifically I you know I didn’t want to just build another broker. Ah you know brokers are fantastic and they bring a lot of value but we wanted to build something that would help the brokers and actually have control over the insurance products. So that we could empower the brokers and intermediaries to do something magical and the literally the week before like at my going away party at a friend’s house I had a conversation with one of them and they they basically said like look. We really think you should focus on just doing the brokerage thing. Don’t try and build your own products. You know that it’s. Too complicated regulatory issues and I said like no I’ve I’ve got to be consistent with the vision I don’t believe in a business like that and they basically said like oh good luck. You know we’re we’re not really interested and yeah telling telling your wife who’s ah yeah, and. And her third trimester with your with your third child that hey we we’re gonna go do this thing and we don’t have any support. Ah, thankfully she took it really? Well, we moved to Cincinnati I searched for another investor but thankfully we found it found a few and. Built the team on you know, like knowing nothing about yeah where the money would come from but thankfully we had people who are working for us even though it was just promises at that point that we’ve paid them and we ended up signing the term sheet on August Twentieth and my son was born August Twenty First that was that was a exciting experience. Maybe maybe a little too exciting.

Alejandro: Wow He oh my God full of excitement for sure now for the people that are listening to really get it. You know what’s say cuttery carter all about I mean what’s the business model there. How do you guys make money.

David McFarland: Yes, so what we do is we we act we’re an insurance manufacturer right? that that’s how we describe ourselves and we we bring speed simplicity and service to the commercial insurance space specifically focused on small commercial to small businesses and whatnot. And what we do is we do this in in two ways one we control the insurance product and 2 we control the tech product. So. In other words, we we are the ones who are building the insurance products and then on the tech product standpoint we’re. We’re creating things such that we can actually kind of magically integrate into the places where it’s most relevant to these in consumers. So we’re pretty much 100 % partnership focused. We don’t really do any d to c so we integrate with the small stuff that small businesses run on yeah quickbooks thrive homie stuff like that. Accounting firms merchant services stuff like that and we also work with the the brokers and the agents that they work with as well to make their job a lot easier so we enable them to bind policies with a minimal amount of information and that just it it helps open up. A market that was previously closed off because the time wasn’t worth the money and by enabling these partners to do more for these small businesses. It makes it so that small businesses can actually be covered and withstand you know catastrophic events and other things that may that may take those businesses out.

Alejandro: Now in the in this case I mean you’re alluding to it How Ah how are you able to really get the the team together especially at the beginning when you didn’t have the budget to be able to allocate to to new employees. How do you get them on board. How do you enroll them mean in what’s possible here.

David McFarland: Yeah I mean a lot of just having conversations with people in cold outreach quite honestly I came to Cincinnati didn’t really know anyone and I probably sent out like a thousand different Linkedin messages to people in the space who I thought had really relevant experience. And thankfully people in Ohio are really nice and willing to grab coffee and this helped me as ah as a leader figure out what people I wanted on my team and who I didn’t you know and you had to tell people like I think you’re great, but like you know this is not someone who I wanted to work with and thankfully we. We’ve always been guided by our 4 core values integrity intelligence passion humility right? We’re smart energetic people who do the right thing and we don’t brag about it and when having that in my mind of like who are the people where I’m going to ask to be on my team. Those core values really guided me and we were able to build just an amazing initial group of people to work on this and yeah I mean you have to you have to promise them like hey money will be there but really like your passion for what we’re doing even though it’s insurance has to overcome. Ah, your monetary desires right now and thankfully we found amazing people who were willing to go without pay for a little while in order to to work on this Ed I couldn’t be more thankful for that initial group.

Alejandro: And going back to the investments. How much capital have you guys raised today.

David McFarland: So now we’ve raised a little over 75,000,000 to date which is it’s comical when you think about where we’ve come and you know those those initial first 2 term sheets.

Alejandro: So how has it been the the experience and the jump from one financing cycle to the other one and the expectations that you also were encountering how has been that experience for you guys.

David McFarland: It’s been thankfully really positive I think we’ve we’ve had a similar experience as a lot of successful startups in the beginning. You’re kind of just figuring out how to how to how to get the the flywheel moving right? and so you’ll have like. You’ll build a lot in the beginning then you start getting sales and like it seemed everyone thinks it’s just like oh you get sales and it’s up into the right immediately that that that is very rarely the case. What often happens is like you have this long period. Maybe it’s long just for the bounders but this long period of like. Oh. It’s it’s not really do anything and then finally you know something works out. You get that big partnership or whatever you get a lot of traction and the fly wheel really start spinning and then who it goes up and to the right and we we experience the exact same thing and you know the funding rounds when. Ah, pre-flywheel right are a lot harder than post-flywheel and yeah it it was like series c series a yeah you’re talking to tons of people and trying to figure it out and series b we went out there with that same mindset of like let’s let’s call up all these people and. I mean it. It went a lot faster than ah than the previous rounds which which was greatly encouraging and a testament to what the team had done.

Alejandro: That’s how amazing now imagine you go to sleep tonight and you wake up in a world where the vision of qtery is fully realized what does that world look like.

David McFarland: I Mean this this succinct way to say it is Insurance is no longer a disparate process. It’s no longer. The separate thing that you do, but it’s integrated into what you’re doing right? simultaneously if you want to go and work with your broker get insurance. Broker literally is just putting the name of your business in and it has full recommendations. What’s done. He can just say yep, all these coverages look right? Click a button done Now. He’s making money off of that small business policy because he’s only spending a minute on it as opposed to days. And by the way that’s ah, that’s not very far off um and then like the other side of it is like it’s all tapped in to the underlying systems that these small businesses run on so they don’t have to do Audits. Of their business right? like everything’s already done and we can say hey we just realized that you bought a piece of machinery like let’s let’s make we’ve already added that to your policy just click here to confirm. Oh We realize that you’ve doubled your employee Count. Don’t Worry. We’ve adjusted your limits Accordingly. We see your revenues going through through. Ah, by the way this this pandemic happened and it’s shut down your restaurant. It’s okay, we we do everything based on revenue. So We recognize that that revenue is low So we’re going to adjust your policy premiums accordingly right? All of those things. That’s that that is literally what we’re bringing to the table.

Alejandro: Now in terms of where you’re at now and and perhaps to give a sense of the folks that are listening. You know in terms of traction anything that you can share in terms of maybe like number of employees or anything else.

David McFarland: Yeah, so we ah we have a little over 150 employees probably over 160 now we’re continuing to onboard both traditional and nontraditional partners seeing great traction there I think right now. In the in the nontraditional space so places where insurance is not the primary focus of accounting payroll Merchant Services we’re seeing that shift towards ecosystem place where they want to be everything to. Their customers. They want to be that that ecosystem that the small business play in and a big part of that, especially for small business is insurance and solving that problem. So we’re seeing a lot of really beneficial stuff in which we can embed in those ecosystems and provide value.

Alejandro: And I know that for you culturere at Cotery. The culture is something Important. So How have you thought about culture and really you know putting the critical fundamental pillars of that for now all these. Employees that that you’ve been boarded and and the more to come.

David McFarland: Yeah, the I mean the mission is to build and foster a world class team to bring speed simplicity and service to commercial insurance and so there are 2 combu to that right? There’s the build and Foster worldclass team and there’s the speed simplicity and service and when we build and Foster World Class Team. We we. We we say we hire and fire based on these things and the the core values are key. There. So when we hire someone 20% is actually based on their their skill right? like we have so we have a need and they have to have a superpower to meet that need the other. Things are the core values Integrity Intelligence passion humility like I said we’re smart energetic people who do the right thing and we don’t brag about it and it’s great to to hire on that but we also have to fire on it if people are. If people have a deficiency in skill like we can work on that with like a professional improvement plan. We we can. We can help get there if the core values are there if the core values are not there if they’re yeah, not having high integrity humility passion Intelligence. Ah, we’re not here to change people right? We’re not here to fix your integrity problem right? like you have to have that basis of the 4 core values if you want to be here at code read so usually in situations where there there is a lack of core values. We we cut timests we we. Fire those employees. Ah, and that’s hard. It’s hard to do that. But we are We are very focused on preserving our culture and it’s thankfully paid dividends.

Alejandro: And you’ve you’ve gone through different cycles I mean as you were alluding to I mean you’ve done seed series, a series B and I think that every financing cycle goes in parallel with that different cycle that the company is going through and and in many instances. Unfortunately you see. Employees that are not able to really grow at the same pace of the company and and you have to make hard decisions. So How do you typically go about that. So.

David McFarland: 1 of the first things I do with everyone the company but particularly my leaders is we have the conversation that the growth of this company the rate at which it grows may outpace your ability to keep up with it as a leader. And just to continue to be honest and provide candid feedback with your leaders about that that that foundation helps build trust and if you do see issues with your leader where they are struggling to keep up. Highlight what those problems are you know, like you said it’s different at each stage right? like some people in the beginning they are amazing leaders at like the the guerrilla warfare stage right? like you’re you’re running through the jungle dodgy bullets all that kind of stuff like they they can do that they can handle that crazy stress and lead people through that. But then they get to you know, post product market fit where they’re leading a team and have to implement process and it’s no longer about ideation. It’s just pure execution right? They’re like 1 just give me a gun I want to I want to go back and fight on the ground and ah that. You got to just be honest with like look you know this is not for you and we love what you’ve done but we think it’s either best if you you it’s you in my opinion, especially like it’s it’s best if we you move on and you have that conversation with them not as anything with tons of animosity but just being real with them and support them. Subsequent to it help them find another job help them realize their potential one. One of the things that we do along these lines is core coaching so direct reports or match shift with their manager and they have a time where they say what do you want to do. Beyond just codery beyond just the objectives and key results that you’re focused on in codery Where do you want to go with your life like I do want to be a cto. Do you want to start a company like how can we help you with that and that that not only helps build a great relationship between the manager and the director port. But it also enables these types of conversations. It helps us figure out like if this person isn’t a fit right? because we’re scaling too fast. You know what could we help them get into. 

Alejandro: You got it now imagine if I was to put you into a time machine and I bring you back in time and I bring you to that moment where you were thinking about taking the leap of faith from clear cover to start, you know cotery and and imagine you had the opportunity of having a chat with your younger self. And give it that younger David one piece of advice for launching a business. What would that be and why given what you know now.

David McFarland: It be the advice I think I give everyone which is focus on first order negative second order positive decision making I like do the hard things they will pay dividends long term don’t it may seem it. It may seem like a good idea sometimes like oh let’s let’s focus on this this short term positive thing right? but those things are usually long-term negative the best some of the best things in life are short term negative long-term positive right? saving money for retirement having kids goodness gracious that that is a.

Alejandro: So yeah, ah yeah, absolutely.

David McFarland: Is a long short-term negative but long-term positive. So yeah, till they like 4 it’s just like what am I doing and then they they slowly get better. Ah, but yeah, it’s the same in business like if you’re going to try and. Shortcut it and do all this stuff like to it’s not going to benefit you long term and a lot of people they see success stories like Elon Musk and Jeff Bezos and Warren Buffett they think like overnight they became billionaires no way. No wait I mean look at what. Paypal went through and Elon Musk when he was starting there. They went through terrible things right? Jeff Bezos has been working on Amazon for twenty plus years it was not an overnight success. Warren Buffett didn’t make his like like join the like really rich category until he was after 55 years old like people don’t think about that I mean Warren Buff it’s also like 90 so but it it’s ah it takes time to to build something and if you’re just trying to like get rich quick or you know shortcut it you’re doing yourself a disservice. Yeah, even if it does work.

Alejandro: Ah, yeah.

David McFarland: Like even if it does like hit that goal of all I’ve I’ve made it to millions or billions or whatever it is you you cheat yourself out of the personal growth that comes through the hardship.

Alejandro: Yeah, 100% David and I think that’s very profound. This is ultimately a ah marathon on entrepreneurship. So David for the people that are listening. What is the best way for them to reach out and say hi.

David McFarland: It’s right? Yeah, you can reach out at coderary. You can also code reinsurance dot com you can also connect me on Linkedin I’m usually a. Busy with with all my kids and and basketball and you know trying to make insurance better but those are probably the best men used to reach out.

Alejandro: Amazing. Well hey David thank you so much for being on the dealmaker show today you.

David McFarland: Thanks for having me all hantra.

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