Kin Insurance Provides Financial Service and Insurance for Those Who Own Homes

The Demotech Difference (TDD): It’s great to speak with you today. Please describe your firm’s background, areas of focus, and how your firm distinguishes itself from the competition.

Sean Harper (SH): Kin Insurance, founded in 2016, is a technology company that provides financial services, including insurance, to people who own homes. We have improved homeowners insurance in two ways.

First, we provide the digital, direct experience preferred by the majority (more than 70 percent) of customers. They prefer having a direct line of communication with us, not intermediated by a middleman. This shows up in our very positive customer reviews (4.9 stars on Trustpilot, 4.8 on Google).

Second, we are able to provide insurance in areas that are overlooked or avoided by other insurers. We do this by replacing the manual data collection that has historically been done by insurance agents. With our technology, we generate a much more accurate and comprehensive understanding of the physical traits of each building. Since our pricing and underwriting is based on this more accurate and more objective input data, we are able to get reinsurance capacity to deploy in difficult markets and really figure out which are the safest homes in a risky area and give those customers a better deal than they would get elsewhere.

Kin serves more than half the total United States addressable market, which is about $200 billion in aggregate, specializing in high-risk areas like California, Florida, and Texas. The reciprocal exchanges that we manage have more than $600M of direct written premium in 2025.

Now that we have reached some level of scale in homeowners insurance, we are beginning to sell other insurance and financial products to our customers. People who own homes are demographically the best customers for many other products, which creates a big opportunity for us to offer more solutions that meet the needs of our customers.

TDD: What is your background, education and experience?

SH: I am an entrepreneur several times over, focusing on the technology and financial services sectors. I founded and was the CEO of FeeFighters, a digital payments company that was acquired by Groupon, and I also co-founded TSS-Radio, a physical products ecommerce company. Prior to my entrepreneurial pursuits, I worked Longworth Venture Partners and the Boston Consulting Group, and I achieved a BA and MBA from the University of Chicago.

TDD: Was there a single event or thought that led you to the formation of Kin?

SH: I had some success with my prior business, FeeFighters. We re-wrote the payments APIs, which were very antiquated at the time and used new data sources to underwrite our small business customers.

I was trying to figure out my next business. As I started doing my research, I remembered a consulting case that I had done at the very beginning of my career, where I was helping a P&C company with distribution.

In that case I learned a few things: First, the branch networks are way too dense; you have roughly five times as many P&C agencies as you have bank branches, even though customers need to visit a bank branch a lot more often than an insurance office.

Second, the lack of a unified experience between physical branches, the website, and mobile interfaces is a big problem for customers, who have been trained to expect a more consistent and streamlined experience by other financial service providers.

Third, in addition to generating sales, agents are relied upon to provide a lot of really detailed information about the house. For example, they are expected to ascertain what kind of pipes are in the home or what type of shingles are on the roof. They aren’t good at that. They are good at selling policies, which is actually in conflict with the goal of collecting accurate underwriting data.

Finally, there are a ton of smart people at insurance companies, and nearly all of them identify their biggest problem as the very out-of-date core processing systems, which are often several generations behind the tech curve at this point.

It seemed to me that I could follow a similar pattern to what worked for me in payments and apply it to homeowners insurance. We would build the technology from scratch to enable greater efficiency and profitability, and develop algorithms to better understand the detailed physical traits of each home, enabling more accurate pricing and underwriting.

TDD: What was your impetus to use the funding model that you selected?

SH: When you’re reinventing an industry, it requires a lot of technology and a lot of money. The venture capital ecosystem has a lot of success funding the re-invention of major industries, including financial industries like banking and payments. Our largest investor is QED, the VC fund founded by Nigel Morris, the founder of the giant credit card company, Capital One.

We also raised private credit to fund the balance sheets of the reciprocal exchanges. That arrangement worked because the private credit investors had interest coverage from the recurring management fees, as well as an asset to lend against — the surplus notes that the reciprocal exchanges issued us in return for their initial funding.
TDD: What underpins the success of Kin?

SH: It comes down to data-driven decision-making and unit economics — always knowing the return on every single dollar and investing accordingly. It’s also about a willingness to follow that data to make decisions that are counter to industry norms. For example, we stayed Direct-to-Consumer when many of the newer companies started around the same time pivoted away and started selling through the traditional channel. We have conviction in that decision because we know the data says 70 percent or more of consumers would prefer to shop directly.

TDD: The introduction of additional services, products and events has enhanced the role of KIN. Have they also changed its trajectory or mission? Please discuss the impact on both.

SH: Our goal is to make homeownership more pleasurable and more affordable. Owning a home is such a big part of our social fabric, yet there really isn’t a financial services business solely focused on people who own homes. That’s a shame, because home ownership right now is more expensive and riskier than ever due to ever increasing extreme weather, higher interest rates, higher materials, labor costs, etc.

Now that we have reached a reasonable level of scale — approaching 250,000 customers with our first product, homeowners insurance — it’s time to start looking at what other products those customers need and start providing those as well.

TDD: What trends or strategies will impact the global insurance industry over the next several years? How have you prepared internally for these changes?

SH: Insurance tends to not adapt quickly to technological shifts. The industry was missing or very late to the last few big ones — web, mobile, cloud and machine learning.

That happened for two reasons. First, barriers to entry are very high in insurance, which reduces the competitive intensity relative to many other industries. This means you can afford to miss a big tech shift and still make money. Second, the disconnect between the distribution and the manufacturing of the product makes real innovation very difficult, as you need to persuade hundreds of thousands of distributors to come along for the ride, which isn’t easy.

There’s no getting around the high barriers to entry in the industry, and we just had to slog our way through them. It took us a year to get regulatory approval for our first reciprocal exchange.

What we could do differently was build the company in a way where we can take advantage of major technology shifts. We are vertically integrated, including our distribution. There is a reason why the cutting-edge cars are being built by Tesla and BYD and not General Motors. It’s very hard to move fast when you need or want to if you depend on a lot of external parties. With every change, you need to convince a lot of other parties to change the way they do things: the software providers, the data suppliers, the agents — all of that takes a lot of time. As a vertically integrated company, if we want to do something we just decide, and then it happens.

TDD: Do you believe that these trends and strategies will impact the United States insurance market to a greater or lesser extent than foreign markets?

SH: It’s a toss-up. The United States is where most of the cutting-edge technology is happening. That doesn’t happen in Europe. It doesn’t happen in Japan. It doesn’t happen in the developing world. China is starting to catch up with us in certain areas.

One reason for that is that our culture is one of iteration, innovation, and risk taking — it’s the best in the world. The other is that we are a large market, so you can justify a very large R&D spend because, if successful, you will generate a lot of revenue selling into the largest GDP market in the world.

Insurance is a somewhat special case because, more than any other product, there is not a national unified market; each state acts much more independently. That fragmentation works against the pace of innovation. Overall, I think the U.S. will still innovate the fastest, but not by as much as in other industries.

TDD: How do you stay ahead of your competitors?

SH: We have a big advantage in that we are one of only a few companies in the industry that have both scale and a fresh architecture. We deployed more than $50M of organically generated capital into innovation in 2025 and we were still EBITDA positive. It’s hard for a startup to compete with that level of investment.

Meanwhile, our legacy competitors are huge companies and are deploying a lot more, but their systems are riddled with deferred maintenance and are built on infrastructure that’s several decades old. They spend most of their money just to keep things running. Our dollars stretch a lot further than theirs — they might spend 10 times more, but not realize the same impact. Even to these large companies, that’s a lot of money.

I strongly believe that the independent agent model dampens innovation, because the agents would logically want every carrier to be basically the same so they can present a list of directly comparable options to the customer. However, if you sell through agents currently, and have a very good business, it’s not actually smart to rock that boat. The last thing you want to do is anger the agents because they can easily take their book of business elsewhere.

TDD: Tell us about your philosophy when it comes to service to your clients. What do you see as the most vital area(s) to focus on to provide the best possible customer experience?

SH: Letting the customer self-service when they want to and having really excellent live support when they need it is super important and something the rest of the industry doesn’t do very well.

TDD: Looking back, can you identify sentinel events that shaped your personal learning curve?

SH: One of the most significant sentinel events that shaped my personal learning curve was my first job out of college at BCG management consulting. I was dropped into major corporations that, from the outside, appeared highly intelligent and impenetrable. However, I quickly learned there were a ton of problems. Multi-million-dollar organizations were relying on teams of 20-somethings to solve their problems.

So many people look at complicated industries dominated by big companies and assume their work must be too hard — that they couldn’t possibly compete. That’s simply not true, and consulting was what made me realize it.

Another major event was learning to program. It’s the closest to magic that you can get. You can write a “spell” and it becomes a real thing. Creating things over and over again with coding gave me the confidence that I could just figure out how to build other things too.

TDD: Working in an industry that is constantly evolving, what measures do you take to ensure that you are at the forefront of emerging topics and developments?

SH: The biggest advantage we have as a startup is that our people are naturally entrepreneurial and hungry to learn. They proactively educate themselves and bring new ideas and technologies to the table that we can quickly evaluate and, often, implement.

Beyond that proactive culture, we specifically hire individuals who are both knowledgeable and obsessive about their fields. We have all these niche experts on staff, and we are constantly learning from them. Our VP of Claims, for example, has taught me so much about claims. We are constantly learning from those around us, and it makes us smarter as a whole.

TDD: What would you say is the ethos behind your firm? Is there a certain culture that defines your company and how do you ensure that these values are maintained across all areas of your company?

SH: The ethos of Kin really comes down to having curiosity and a low ego. These traits help us discover new things.

Our culture is defined by our “Blank Sheet” approach, which is maintained by repeatedly asking “what if?” The idea behind that blank sheet comes directly from the Buddhist concept of Beginner’s Mind: assume you know nothing and start from scratch.

TDD: What makes your company unique? What separates you from your competitors and marks you as the best option for potential clients?

SH: Delivering an incredible customer experience, using plain language, and ensuring every client can connect directly to a human is core to Kin. We deliberately go into markets that traditional carriers often avoid, providing a high-quality product to customers who typically have the fewest choices.

TDD: How do you define “success?”

SH: If I make people’s lives better, that’s success.

TDD: What are the traits and skills of people who are likely to be successful at Kin?

SH: You should be highly entrepreneurial, driven, and good at making fact-based decisions and never ego-driven or territorial.

TDD: What advice would you give to someone who wants to try to do what you have done?

SH: You need to be prepared to fail and pivot off that failure. Most of the things you try don’t work, but we’re in a game of asymmetric returns. Think of everything as small experiments. Scale the things that work. Kill the things that don’t.

TDD: What was the most important thing you learned in school? In business? In life?

SH: School: Being able to read is the only thing that matters, because then you can teach yourself anything.

Business: You really need to be unafraid to ask the dumb questions. A lot of people fail because they repeat what they’ve heard and accept “what is” without ever essentially asking “what if?” Successful people understand at the absolute, most basic level how things work and are ready to re-engineer them.

Life: It’s ultimately a lot more satisfying to invest in other people than it is to invest in yourself.

TDD: Is there one more goal — personal or professional — that you would like to accomplish?

SH: See my kids grow up to be successful and happy.

TDD: What is the best advice you ever received? Who gave it to you and what were the circumstances?

SH: I was a Goldman Sachs intern in college, and I was walking in the city to a meeting with the managing director. At the time, I was really afraid of looking dumb. We were going somewhere and the guy went charging off in one direction and I just walked along with him even though I thought we were going the wrong way. It turns out we were going in the wrong direction.

He looked at me and asked, “Did you know we were going the wrong way?” I said, “Well, I thought so …”

His response: “You may not have confidence, but you need to think it, just do it. Have confidence in yourself. The world is never going to tell you to be confident, you just need to do it.”

TDD: How did you get involved in the insurance industry? What attracted you to it? What keeps you here?

SH: My early career in consulting (and the problems I uncovered) brought me to the insurance industry. I find the industry fascinating and intellectually interesting. It keeps me learning every day.

TDD: Would you share your thoughts on why young professionals should consider the insurance industry for their careers?

SH: Because it’s important; one of the most important industries out there. You can do something meaningful that helps the whole world evolve. In insurance, you get to do something important that gives you purpose and meaning.

TDD: What is your most cherished professional accomplishment?

SH: I love seeing people who have been involved in my endeavors launch their own things. I am incredibly proud that we’ve created so many growth opportunities for people, including lots of senior leaders. A perfect example is Holly Rousseau, our chief of staff, who originally started with us as a sales agent. Since then, she’s had eight other roles on six different teams. I have another direct report who has been at Kin since the early days and will soon be leaving to build his own startup. I’m very proud.

TDD: Tell us about a setback that turned out to be an opportunity in disguise?

SH: In early days, before Kin had the reciprocal exchanges, we offered insurance in partnership with an existing insurer. Things got a bit rocky at one point, which was very stressful, and prompted us to create our first reciprocal exchange, which ended up being very positive for us.

TDD: How did your company create a following?

SH: Our customer experience. We use technology to do the basics very well.

TDD: What must an insurer be doing today to remain relevant five years from now?

SH: I think the reality is very little. This is an industry where you can be very complacent for a long time and be fine.

TDD: Can a company have “bad” profits?

SH: Yes, if you’re getting your profits by deceiving people or manipulating the market, that fundamentally breaks the system and those would be “bad profits.” Capitalism is supposed to work for people. It’s also a problem when a company becomes a monopoly or has too much market power; it’s great for their profits, but it’s not good for consumers.

TDD: If no one would ever find out about your accomplishments and success, would you lead differently?

SH: I don’t think so. The reality is that when you are doing something challenging like what we’re doing, there isn’t much external validation. And sometimes, more people want to see you fail than succeed. You only get credit well after the fact. You have to be doing it for intrinsic reasons or it’s not worth it.

TDD: Who was the most interesting person you ever interacted with? Why?
SH: When I was in college, I had Steve Levitt, “Freakonomics” author, as a professor. His level of curiosity was off the charts. He wanted to know everything about everything and was quick to get into analysis and details. I really admired that curiosity. He was also an excellent and engaging professor.

TDD: A lightning round of personal questions. There are no wrong answers!
Favorite movie?

SH: “Star Wars.”

TDD: Best book you ever read?

SH: “Atlas Shrugged.”

TDD: Favorite snack?

SH: Steak.

TDD: Favorite meal?

SH: Barbacoa tostadas.

TDD: Hobbies?

SH: Fixing my sailboat.

TDD: Where is your hometown?

SH: Shorewood, Wisconsin.

TDD: Dog or cat person?

SH: Bulldogs.

TDD: If you could live anywhere in the world, where would it be and why?

SH: Chicago. It’s the best big city in the world.

TDD: If you could have any superpower, what would you choose?

SH: Time travel.