Sean Haper and Lucas Ward are the cofounders of Kin Insurance which fixes home insurance through intuitive tech, affordable pricing, and world-class customer service. The company has raised so far over $60 million from investors such as 500 Startups, Omydiar Network, August Capital, Chicago Ventures and Commerce Ventures to name a few.
In this episode you will learn:
- The importance of embracing failure
- Why itâs easier to go bigger than thinking small
- Why financial services is such a great space for tech entrepreneurs
- The huge problem with enterprise sales startups

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About Sean Harper:
Sean Harper is the CEO and co-founder of Kin Insurance, an insurtech startup and licensed insurance carrier that leverages technology to simplify homeowners insurance.
Previously, Sean Harper founded FeeFighters, a payments company later bought by Groupon, and TSS-Radio, an e-commerce company that became an Inc. 500 fastest-growing business.
Before becoming an entrepreneur, Sean Harper was a consultant at the Boston Consulting Group and an investor at Longworth Venture Partners.
Sean Harper earned his AB and MBA at the University of Chicago.
About Lucas Ward:
Lucas Ward is the co-founder and CTO of Kin Insurance.
Previously, as CTO of Fundspire, Lucas Ward created a disruptive and innovative product in the financial industry from the ground up.
Lucas Wardâs efforts to define infrastructure in the Amazon AWS cloud and write batch jobs and Javascript code culminated in the successful acquisition of Fundspire.
During seven years of consulting for Accenture and ThoughtWorks, Lucas Ward helped large corporations in finance, insurance, aviation, pharmaceutical, telecommunications, and logistics; federal, state, and local governments; and various startups improve the way they use technology.
Lucas Wardâs areas of focus include open source, programming practices optimization, architecture design and maintenance, and agile methodologies.
Lucas Ward also co-led the creation of Spring Batch, the first and only open-source batch processing framework, which is part of the celebrated Spring portfolio.
Connect with Sean Harper:
Connect with Lucas Ward:
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FULL TRANSCRIPTION OF THE INTERVIEW:
Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have two co-founders, some very, very interesting profiles, very interesting track records, and backgrounds. Definitely, weâre going to be learning about markets that are heavily regulated. Weâre going to learn about home insurance, tech, building, and scaling companies, and you name it. So without further ado, Iâd like to welcome our guests today, Sean Harper and also Lucas Ward. Welcome to the show.
Sean Harper: Thank you. Thanks for having us.
Lucas Ward: Thanks for having us.
Alejandro: So why donât we do a little bit of walk through memory lane, guys, to get to know you. Why donât we start with Lucas? So, Lucas, I know that you were born and raised in rural Missouri. How was life there?
Lucas Ward: Not as exciting as it is in Chicago.
Alejandro: Why is that?
Lucas Ward: We had our one stoplight and a Burger King, so I guess if thatâs your definition of exciting. The biggest town over, youâve got to drive into. I graduated with 60 people in my high school. I probably switched middle schools and high schools seven times. I probably went to all of them in similar-sized towns. So I think in a lot of ways thatâs probably what drop me to computers and the internet in the first place was a connection with the wider world even if it was on dialup.
Alejandro: So why donât we talk about that for a bit, Lucas. Tell us about how you started to develop this love for computers.
Lucas Ward: I remember being bought a computer from Walmart. I donât even know what it was. It was very, very crappy. My parents have never been very good about computers, so somehow, I ended up figuring it out and was the one. I think almost all of that started from wanting to play games doing some troubleshooting as well, where you were trying to get the games playing, you couldnât figure it out. Back then, it was a DOS prompt, so you had to get everything in and type into a DOS prompt. So I was used to working outside of a Windowed environment for a long time. We didnât have a lot of money, so I started learning how to put computers together and build them because that was the cheapest way to do it. I got salvage parts, and I found people to give things away, so I learned how to build computers from there. Funny enough, I think the high school I graduated from, there was a class which was me fixing the schoolâs computers. I got an A. Yeah. Iâd just run around and fix computers in school. I told you the state of the schools I was at, so itâs still a good learning experience.
Alejandro: Very cool, and then you went and got your computer science degree from Missouri State University, and you went to Corporate America and open source. You started to develop that learning, that exposure to open source with Accenture. Tell us about this.
Lucas Ward: Yeah. It was definitely a big shock for me. Iâd never been on a plane before. Then I joined Accenture and started living in them. I got a great opportunity. Accenture, at the time, was working on a lot of big batch processing systems, so these things youâre processing millions if not billions of records at a time. They were rebuilding the frameworks. Nobody had ever built something like a batch processing framework, but Accenture built them internally. So I ended up getting pulled into that and creating a version. What we wanted was, at the time, Accenture was getting good luck from using these external frameworks. I think Struts is a good example in the Java world. That was creating a lot of continuity between client sites. So Accenture liked it because you could switch resources around, and they need a framework. They got to the point where they stopped viewing internal frameworks as some kind of competitive advantage and realized there was a cost. So they were pushing it, and I was at the forefront of pushing open source, which was all happening along with outsourcing in the early 2000s. I wrote the first version of that. I worked with the people at SpringSource, which later was bought by VMware. We put that version out. I was working with a lot of clients, probably 20 or 30. Everyoneâs from the state of Illinois, California, the City of New York, to Chase. I even worked in Europe, which was really fun for me in my early to mid-20s. It gave me a big, broad overview of a lot of these things before moving on.
Alejandro: So, obviously, you were doing a bit of corporate here. Iâm just wondering. What was that first exposure to startups because you did ThoughtWorks, Fundspire, and then Rippleshot. What was the first moment when you finally said, âOh, wow. Look at startups, what theyâre like. This is really cool.â
Lucas Ward: It was probably SpringSource if I think about it. The funny thing is, I hadnât thought about that before. But, yeah. The SpringSource was my first one. I remember going to their offices. It was in Southern England. There were eight people in the office. I think that was my first startup experience because everything else was very big corporate up until then.
Alejandro: Yeah. Sean, why donât we go through your background a bit here. Obviously, as well, a little bit geeky in terms of love for computers and all of this. You started programming quite early. How early?
Sean Harper: It was probably 11 or 12 when I first started to program. Part of it was I just wanted to make things, and part of it was my parents. I had an aunt who worked for a tech company and had made a lot of money off of it. My dad was like, âYou should do this. This is a great career.â Heâs pretty geeky, too. So they encouraged me. At the time, it was crazy. You couldnât look things up on the internet, so it made programming a lot harder because youâd have to go buy a book and look up how to do something. I got into that, and I really liked it. Iâve always liked making things, and the fastest way to make something cool is on the screen. That got me into the business stuff, too, because if youâre making something, the next thing you want to do is get people to use it. Then you have to figure out: how do I promote this? How do I figure out what it is that people want? How do I charge them money for it, and how does this all work? It was through programming that I got into business stuff.
Alejandro: Got it. And with your background and track record, you are what I would call in the positive and good sense a very dangerous entrepreneur. The reason why I say this is, Sean, is because youâve had experience in consulting. Youâve had experience also on the investment side on a venture capital firm, so not only are you able to really understand how to resolve problems and grab big problems and then break them into smaller problems, but now, youâre also able to identify patterns of what makes companies successful. So can you tell us about these two experiences and what you learned from them?
Sean Harper: Yeah. In my first business, I started as a side gig when I was working at a VC firm. From that, the biggest thing I learned was that you actually can start something out of nothing and have it turn into something. I had started this business with a friend, and we pivoted twice. It started with a product that nobody wanted, and we iterated our way into a profitable business. I think that taught me that itâs okay to take a leap. You donât need to be 100% sure about something. You can actually just get out there and start selling something and pivot off of that. It gave me a lot of confidence. Then my second business, when I started, it was a payment processing business. I had been running this e-commerce business, which was my first one, TSS-Radio. I started FeeFighters out of a frustration that there were not very good online payment options at the time. This was in 2005, I guess. PayPal was stagnant. Stripe didnât exist yet. Square didnât exist yet. So Iâd been struggling with these legacy payment guys. I knew from my time at BCG â this is the other cool thing about consulting is, you learn how things should work. Iâm sitting there looking at this like, âOh, my gosh. Big companies pay 2% for their payment processing. Why am I paying 5% as a smaller company?â It turns out there are a lot of reasons, but theyâre all ones that are easily surmountable if you have the right tech and the right business model. With FeeFighters, I learned two things. A good pattern for us as techy guys is to go after financial services because thereâs no physical thing. Everything at a bank, everything at an insurance company, everything at a stock brokerage is done online, on the computer. Youâre really just pushing data around, but youâre getting paid way more to push that data around than you are in most businesses. From that, I always wanted to do more financial services stuff. The other thing that I learned was that the problems that I had seen at the big companies when I was a consultant were really good hunting ground for starting into startup. Thatâs been true. A lot of investment thesis for Kin came out of work that I did at BCG working for a big insurance company.
Alejandro: You got FeeFighters acquired by Groupon, so this is a great opportunity to see the full cycle of a business. When you were there, perhaps doing the vesting and resting at Groupon, some people donât rest as much as others, but when you were doing the vesting and resting and reflecting on the journey, what was that big takeaway?
Sean Harper: You know, I didnât really rest and vest at Groupon because Groupon, when they bought us, was still a startup, too. They had just gone public, and they had all kinds of problems to solve there. As a problem-solver, I saw all these problems as opportunities. So I did a bunch of stuff that was outside of the business that they acquired at Groupon, especially automating the onboarding and unwriting of merchants to the Groupon platform. That was a cool experience because I got to know what itâs like to work at a real tech company. Everything that I had done before was VC is VC. Doing these little startups, you only know what you do, and you donât know what Best Practices are. But at Groupon, they had a lot of people who were from Amazon. They had a lot of people that were from other big tech companies. It was a good education for me. I learned like, what is a product manager at a big company actually do? It turns out there is a lot of stuff they do that is of value that I had never done before. So, I learned a lot.
Alejandro: Lucas, why donât you tell us about that day where you met Sean?
Lucas Ward: It was at a coffee shop that Sean worked out of almost exclusively at that point.
Sean Harper: I loved that coffee shop.
Lucas Ward: Yeah. It was also next door to this Middle Eastern restaurant, both of which have closed down now. I remember I was at an inflection point in my career, having done a couple of startups. I was thinking about where I want my future to go. I think itâs one of those things, I look back now, and came in as brutally honest like, âI donât know. Iâve taken some singles of doubles. I really just feel like I want to take a big swing.â I think that was a lot of the impetus for it. Sean was telling me about the thing he was involved with at the time, and I remember simply saying, âI think thatâs dumb.â What shows you to Seanâs both persistence and selling ability, he convinced me to join even though I immediately thought it was dumb. It turned out I was right.
Sean Harper: You were right.
Lucas Ward: But, heâs a convincing dude.
Alejandro: Got it. So then, Sean, tell us how you guys incubated the idea of Kin Insurance, and then what was that process of bringing it to life?
Sean Harper: Iâd been looking for something that fit this pattern of a financial product that hadnât been streamlined yet. Like I said earlier, if you look at whatâs really happening in your insurance company or bank, itâs basically software. They just arenât very good in software. Lucas and I were working on this turnaround gig and kicking a bunch of ideas around. I remember we would take walks and like, âHey, what about this? What about that?â Then weâd go and research. And it was fun. Around that time, I think we both bought our first houses. Because thatâs what you do when youâre in your mid-thirties, and I remember being so shocked by how anachronistic the house-buying process was. I said, âThereâs got to be something there? Why is it so archaic? All this paperwork, this negotiation, you have to do all this stuff, and itâs all managed on spreadsheets and emails. Itâs really inefficient. It shouldnât be this way.â We wanted to pick a piece of that off, and I was like, âWell, you know whatâs really surprisingly frustrating was just getting insurance for this house.â Like a lot of people, I was about to close on the mortgage, and the mortgage guy goes, âOh, yeah. You know you need insurance for this house.â I was like, âReally?â He was like, âYeah. You know the close on the mortgage, you need insurance.â I was like, âOkay, cool.â âSo, you should call your insurance agent.â I was like, âWhat? My what? Do you mean like GEICO? I guess I could call GEICO.â Who has an insurance agent anymore? Itâs not really a thing for people our age. So I did. I went to GEICOâs website, where I had my auto insurance, and I tried to buy home insurance by them. It was crazy and frustrating because they basically sent me offsite to some Liberty Mutual site where they asked me all these questions about a home that I didnât even live in yet. Iâm like, âYouâre asking me what kind of shingles are on the roof of this home. First of all, I donât know. Second of all, Iâm scared of heights, so Iâm not going to climb up there and look at it.â It was so frustrating. The one thing I actually did have a question about was whether this giant tree in my yard was covered, and there was no way to get an answer to that. So, I think that was when we started thinking about homeownerâs insurance. Weâre very deliberate and practical guys, so we laid out a plan of, âWhat are the things we need to prove to ourselves before we think this is a good enough business that we should invest our time in it?â The first thing was, we thought it might be possible to eliminate that whole question-asking signup thing and make you able to insure your home with one click. We thought that would be possible because if you search for your address online, you see all this data about your home. So the first iteration of that was us sitting around in a conference room trying out new APIs and saying, âIf you give me an address, can I piece this together that I know enough about you home to insure it? At the end of a few weeks, we were like, âYeah, there is a lot of data out there. This all kind of works.â The second question we had was, âWell, we donât want to build a bunch of software if we donât think we can get customers. So we built this really basic MVP, which is a bit of a wrapper around a retail insurance agency.
Alejandro: Got it, and both of you, in that sense, Sean, you both have engineering backgrounds. So Lucas, how did you guys divide and conquer? Then, also, how did you go about building a team?
Lucas Ward: I think in the early days, I was doing most of the coding. We did everything in Rails. Sean was doing, initially, product, tech. I remember in the first version you did that who ad-libs thing.
Sean Harper: Yeah.
Alejandro:
Lucas Ward: You were filling that out. So we divided it that way. That was, I think, the way we were used to working. Thatâs the way weâd been working previously. We were doing it that way. What I think Sean probably glossed over is we actually went out and bought a retail insurance agency. I need to go back to the singular thing you can think about as an entrepreneur is that there are a lot of these things that you can just do it. I think what hangs up a lot of people from starting businesses is pretty much that single thing like, âNo, you just go and do it.â So the starting point was that. We found one and were able to purchase it, and we were able to layer this on because one of the questions people ask is like, âAre we actually able to make this better without going too deep in?â I remember not long after doing that the quote time was what? Thirty minutes? After Larry and the tech, it went down to five minutes.
Sean Harper: Yeah. It took Lucas like two weeks to make the thing six times as efficient as it was before.
Lucas Ward: Yeah. That was just me and were still part-time, and I think thatâs naturally where things have progressed since there is, very quickly there was a lot of these external things because the thing about going into an industry like home insurance, which youâre sort of the first wave of innovation. There are all of these things that exist in many other spaces that help enable startups just donât exist. So there have been a lot of things externally that have had to be pieced together to even allow us to do the things we need to do to sell anything. I think thatâs how some of the beginnings of Sean and my working relationship to date started to form.
Alejandro: Itâs interesting what Sean was mentioning earlier when purchasing the house and dealing with an archaic process where you had to call your insurance broker. Obviously, that was probably the case because itâs very hard to innovate in markets that are heavily regulated. So the nature here is that not only are you guys dealing with the uncertainty of building a company from nothing, but then also with the uncertainty of making sure that you are compliant with the regulatory frameworks that you have in front of you. So, Sean, how did you go about reducing that steep learning curve as well on the compliance side?
Sean Harper: We decided to go out and do it. So we found out quickly that itâs very easy to get licensed to sell insurance, which is what the initial business model was. So Lucas and I went and got a license as insurance agents. We took a class and took a test, and itâs not hard. Then we had to figure out, âWhatâs the next step? We canât innovate the way that we want to do if weâre just wrapping somebody elseâs insurance product. Thereâs all this innovation that we want to do, and we want to run everything through our own core system. We knew from the start that we didnât want to be selling tech to insurance companies â
Lucas Ward: Absolutely.
Sean Harper: Itâs just that the adoption cycle that is, so what? The reason why that industry is so messed up right now is that it takes a big insurance company like a decade to shift their tech, and thatâs if theyâre dedicated to it. We didnât want to have to wait five years to have somebody buy our software.
Lucas Ward: I remember very distinctly, Sean and I had two rules when we were going forward for this business. Anything that we were doing had to get big, and we had to be able to do it fast. I think anything with a big enterprise sales cycle fails the second check every time.
Alejandro: Got it. To follow-up on that, Lucas, what ended up being the business model?
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Lucas Ward: With those in mind, we were looking at the insurance industry. The reason home insurance stood out is, one, itâs a very big market. Itâs 100 billion dollars and rising. The other thing about it is that itâs 94% sold through agents. So as entrepreneurs, when you see something that has a big manual process, you think, âWow. I could probably automate that.â The other interesting thing that I think shocked us from the very beginning and got us interested is that agents make up about 15-20% of the cost structure. Itâs not even like a [0:22:33] thing. They get that year-on-year.
Sean Harper: Yeah, but itâs actually worse than that because a homeownerâs insurance company, they spend 70% of their money paying out claims. Then the 30% is like a real cost structure. Of that 30%, between 15 and 20 is getting paid out to the agent. So itâs actually like half of the real cost structure. Itâs a huge part of it is getting paid to these tiny operations, like two or three-men operations and strip malls all over the country. There are more insurance agencies than there are fast food restaurants, which to me, is insane because I eat fast food once a day, not necessarily McDonaldâs, but like maybe Chipotle or something, and Iâve never, ever been inside of an insurance agency. And I think itâs true of most people. In fact, if you go stand outside of an insurance agency, you wonât see anyone going in and out. Theyâre all doing business over the phone and email anyway. So we wanted to rebuild the entire industry, like the whole stack. The natural thing that we gravitated to was, âHey, we want to start an insurance company.â So we looked into that, and we were like, âOh! This is really hard,â because â maybe getting a license as an insurance agent is really easy. Getting licensed as an insurance company can take years, and also, tens of millions of dollars, if not more just sitting there in the bank you canât spend, to make sure that you have the credit rating to get regulatory approval.
Alejandro: Yeah.
Sean Harper: So we found an intermediate point, and thatâs what we did next was, we became this thing called an MGA, which is a virtual insurance company where you run the whole operation, or at least most of the operations of the insurance company, but you borrow or rent a license from another company. Thatâs what we did for the next two years. It was a good business model because it was easy â not easy, but it was easier than starting an insurance company at the time.
Lucas Ward: A lot of these things, I think Sean and I were surprised because we came from regulated environments. Weâre really used to that, and some of the things, especially in payments, are extremely tightly regulated, and we expected insurance to be just as tight. Because itâs regulated at the state level, itâs very different. I think this is how we ended up focusing on finding the states with the good opportunities for us and working on them because if you want to be able to be in the entire U.S., you have 50 states, 50 different regulators to go through. Thatâs challenging.
Alejandro: Yeah, and to think as big as you guys were thinking, and are thinking, that requires some capital. So, Sean, how did you guys go about fundraising?
Sean Harper: We raised the first round, which was at the beginning. This was when we were just doing the first version of the software. That didnât take that much money. We wanted enough money to hire a couple of other guys to work on this with us. So we were able to go out and raise almost 800k from people we knew. It was other entrepreneurs, and it was people we had worked with before, and that was an easy round because they trusted us. We didnât know exactly what we were doing, but they knew we were smart guys who had a good track record, that weâre going after a big opportunity, and that was enough. A year later, we were just launching the first real version of the product, and that was the MGA version of the product. That was tougher because, for the first time, we had to raise money. Our friends didnât have enough money for that round. We were trying to raise 3 million dollars, and we had to ask strangers for money. Thatâs always a lot harder, especially because we hadnât launched this product yet. It was expensive to build it. We had to build all of this tech. We had to negotiate this complicated agreement with this other insurance company, and it was hard and expensive. But, fortunately, we brute-forced our way through it, and we found some investors who believed in it who were folks that our first investors had introduced us to. That was great. The value of our first group of our super-tight friendly investors added was not just their money, but it was also their connections. They helped us raise the next round. From there, itâs been a bit easier because when you have a business thatâs going and has metrics and if youâre growing and start showing the progress that you should, it makes things a bit easier. So the next round was our Series A, and that was much bigger. It was 12 million dollars. We raised it from a VC with a rally good reputation. That was actually an easy round. We had a bunch of term sheets. We got them quickly. Then it seems like we had one easy round, and then one hard round because shortly after there, we decided if we didnât like this whole insurance company thing. It was too inefficient. It was too slow. We hated having our fate rest in the hands of somebody else. That was very uncomfortable for us. Then we set out to raise a much larger round to actually fund the business. But also, to have that big pile of money, I talked about, to get our own insurance license. That was harder because the kind of investors weâd been raising from were these tech VCs. They were excited about the business, but what they were not excited about was having 35 billion dollars just sitting in the bank doing nothing for regulatory requirements. So we had to go out and meet a whole new type of investor. So we ultimately ended up raising that regulator capital, not from VCs, but from a reinsurance fund and from a life insurance company. We didnât know anyone in that space, so that round took a year to raise because it was folks that we didnât know. We had to network our way into the space and explain to them what we were doing.
Alejandro: When it takes that long, itâs a tough battle, as well as emotionally. This reminded me. Can you guys share perhaps, Lucas, and maybe Sean after, a moment that has been difficult, and perhaps it was like a breakdown, or it was a natural breakdown that led to a breakthrough?
Lucas Ward: I think the moment Seanâs talking about â I would say deciding to be a carrier was one of those chips-all-in moments. Thatâs the way that I describe it a lot because it was a bet we were making, and I think Sean and I have had two or three of those different inflection points where weâve said, âLetâs just do it.â We knew there was some risk involved, but we knew to do the vision that we wanted to do, that that was what was going to happen. I think that year, there was the least overlap between Sean and me. Like Sean described, that was really, really hard. Credit to Sean, because he did most of the work on it with a lot of other people on the team, where I was working internally because we had to all the sudden be a complete insurance company. We had to have all of our tech systems; all of our people had to be lined up such that it would be terrible for Sean to get the money we donât actually have a business that can actually operate as an insurance company. So we had zero overlap between the two of us. Luckily, Sean and I have always tended to be on the same page without having to talk too much about it, but that was a really, really trying, and defining year for us. Ultimately, we got there, and we got over it, but it was very challenging.
Alejandro: To follow-up on this, Sean, a moment that it felt like you guys were really turning the corner, and you felt you were onto something big.
Sean Harper: Yeah. One that Iâm thinking of is â this is like four months after we had launched the first MGA version of the product. We knew we were going to grow fast on a percentage basis in those first months. Then we just kept doubling every month, and it was like, âDid we just double again? Itâs crazy. Can we possibly do that again next month?â Sure enough, we did. We were growing so fast, and we were hiring like a new person every day, and it was like, âWow! Weâre really onto something. People really want what weâre selling.â That was exciting because Iâm always worried â am I building this for no reason? Is there not going to be a market there, especially with things like this that are pretty hard to build? That was exciting. That was cool.
Alejandro: Very cool. Lucas, how big is the operation today or the business. Perhaps you can tell us about the number of employees or whatever you think would paint the picture of Kin for the folks that are listening.
Lucas Ward: Weâre into the hundreds of employees now. We have a decent-sized dev team. Maybe weâre all together. Because weâre a direct-carrier, we actually have an ops organization, which was interesting for us. Iâve had some people that were on the phone with customers, but I donât think for this size, we have a lot of those people and have our own call center at scale, which is interesting and pretty cool, especially being able to walk by and hear them talking to customers. Sean and I both, at times, will sit over there and listen to those things. I think now we actually have a lot of the pieces. We have insurance people working here, which I think is an interesting thing that weâve done.
Sean Harper: Like actuaries.
Lucas Ward: Actuaries. Sometimes, I think itâs like, âWeâre an actual insurance company. We have all the things.â
Sean Harper: Appliance claims.
Lucas Ward: Yeah. All across the board. There are definitely times when youâre having done this from literally just Sean and me in a coffee shop. To hear, youâre in your office, youâre looking around, and youâre like, âOh! There are hundreds of people here.â
Alejandro: Thatâs amazing. Sean, when you have hundreds of people, you need to make sure that you guys are embracing culture at the same time because when youâre growing fast, itâs very easy for things to fall apart when it comes to culture. People are everything because, with no people, thereâs nothing. There are no numbers. There are no results. Thereâs nothing. So, how do you guys go about culture, Sean?
Sean Harper: Weâre working on it. Itâs actually more of a Lucas question than a Sean question.
Alejandro: All right. Go head, Lucas.
Lucas Ward: I think itâs as we build up people. I think the one thing is that you have to think about culture because if you donât, one will develop, and it will probably wonât be a good one. So one of the things Sean and I did earlier, where I think Sean was more involved with culture, was â we always had the joke that we had four company values. One of them was, run through laws, and really, that was a bias for action because we had seen this before where people werenât doing a thing because they were afraid they might do the wrong thing. Weâd say basically, âAsk forgiveness, not permission.â The second one was, be chilled. I think anybody whoâs done at least one startup will tell you how much itâs like â there are a lot of things going on, and people are going to make mistakes, and youâre going to have things thrown at you. Everybody just needs to be cool, because if you donât, and you get really angry, itâs not good. Also, I think Sean and I have always had this cultural thing about we shouldnât be doing anything that you canât do for a long time. I think Iâve described it to some people recently to a group of college students. That doing a startup is like a marathon like being chased by a tiger thatâs on fire. Itâs very tempting, and I know Iâve fallen in this in the past. Itâs like, âOh, weâve got to get this next fundraising thing, or weâre just going to kill ourselves.â The thing is that to get that new fundraising thing, youâre expected to take that money, do a bunch of things. You really have to just keep yourself at whatever level you can maintain. The other two values that we had, which we forgot, which is the third value that if something is not providing value anymore, donât keep it around. One of the challenges, when youâre growing a business, is that you have to become a new company roughly at every fundraise. Now, weâre building a Series B company before building Series A, and those are very different things. Some of the people you hire are different, and some of the concerns are different. So just because we do it this way or have done it this way doesnât mean we should continue to do it that way.
Alejandro: Not only do you become a new company, you also become a new executive. You canât lead a company the same way when you are at a seed stage than when you are probably at a Series B or a Series C. So how do you transform yourself, and youâre able to keep up with the growth of the business, as well, Sean?
Sean Harper: One big thing that weâve done thatâs helped is we want the person who has the most information to make the decision. So we always push decisions down to the lowest level because the reality is, there is nothing, there is not a single thing â maybe there are a couple, but there arenât very many things at Kin that I know more about or Lucas knows more about than somebody else. Thereâs always an expert of something. So I think a lot of founders stumble when they get to a certain size, and they canât be involved in every decision. We donât want to be that way. I donât want to be the [0:36:48], and I donât want people to wonder like, âOh, what would Sean think?â Iâd rather have them look at the data, make a decision, and if they need help, then weâre there to help them. Our job as leaders is more one of unblocking people and making sure that we have the right people working on the right things than getting involved in the day-to-day. Iâve found that to be helpful as we scale. Itâs only becoming more and more helpful. And also, the employees really like it because it gives them autonomy, and they donât need to worry about somebody micromanaging them by looking over their shoulders.
Alejandro: Yeah.
Lucas Ward: Also, Sean and I hate managing. We havenât had a lot of the troubles of the delegation versus management thing because weâve always just hated managing. So weâre always looking to hand something like that off and to focus on the bigger thing.
Sean Harper: You could have had a nice virtual cycle there where if you hire people that can handle their own business, then you donât need to manage them. And if youâre not micromanaging them, then you attract that kind of people that want to just get things done and not have somebody â
Alejandro: So, basically, hiring leaders rather than followers.
Sean Harper: Thatâs a really good way to put it. Yeah, I think so.
Alejandro: Love it. So one question that I typically ask the folks that come on the show is, knowing what you guys know now â the ride with Kin is incredible and what you guys have been able to accomplish and all of these different milestones that you have achieved. Now, looking back in time, and weâll start with Lucas. And Sean, you can go ahead with your thoughts on this. Lucas, if you had the opportunity to have a chat with your younger self, what would be that one piece of business advice that you would give yourself before launching a business and why?
Lucas Ward: Well, thatâs a really interesting question. Itâs funny. I think where my brain first goes, and you think about things is, one of the things that Iâve learned the most is probably how not to get hung up in the past. You think about some of the things. You think about if you were to tell your younger self something. Iâve thought about this before. How would I explain this thing to my younger self? I think knowing my younger self, I know he flat-out wouldnât have listened.
[Laughter]
Lucas Ward: So, you think about it, and you think about this, how important the experience is. If thereâs anything that I guess Iâve learned is how important failing is. Youâve just got to go and do the thing, youâve got to fail, and youâve got to be okay with failure. You have to say like, âI failed at this, but Iâm not a failure.â You have to be able to control your emotions enough to not get so hung up at that, that you can look objectively at the failure and be able to improve from it. Because if youâre so worried about whether youâre going to fail or not or whether this is going to work, youâre going to end up not doing anything.
Alejandro: Thatâs very, very powerful, Lucas. So, Sean, what would you say?
Sean Harper: I think I would tell my younger self to go beg and go faster. It always seems easier for me to do the practical, small thing. But the problem is, when youâre doing that, you donât have the grand vision, and youâre not trying to do something thatâs transformative. Itâs actually harder to attract resources. Itâs harder to attract money to that. Itâs harder to attract people to that. Itâs harder to attract attention and press. So I wish I had started going after bigger things earlier in life because in some ways, going after the bigger thing is actually easier. Itâs so much easier to get resources for it, and itâs sure a lot more fun.
Alejandro: Got it. Guys, for the folks that are listening, what is the best way for them to reach out and say hi. Maybe thereâs a customer or a website, or maybe you guys want to share your social media handles. Weâll start with you, Sean.
Sean Harper: Weâre on Twitter at @kinsured. You can always hit us up on the website, which is kin.com.
Alejandro: Great, and do you guys have any other social media? Do you guys use any of that stuff?
Lucas Ward: We have them. I remember a time when I had the time to use them. That hasnât been for a while.
[Laughter]
Alejandro: All right. So probably better to just avoid that, then, for the folks that are listening. I want to say, guys, that it has been a pleasure to have you both, and thank you so, so much for being on the DealMakers show, Lucas and Sean.
Lucas Ward: Thank you. Thank you for having us.
Sean Harper: Thank you.
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