He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure

Wayne Slavin (00:00:00) :
They didn't have to build anything new. We were building everything. We just needed their product to sell. Deca billion dollar insurance brands will be built by Sure, because of what we saw in auto insurance with that AV brand.

Pablo Srugo (00:00:17) :
Did you think it would take ten years plus when you first started this?

Wayne Slavin (00:00:20) :
Oh, no. No, no, no, no, no. It is absolutely a question of resilience and just keeping on going. I just happened to unknowingly choose an industry that a decade is equivalent to a year.

Previous Guests (00:00:37) :
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is product market fit.

Pablo Srugo (00:00:49) :
Do you think the product market fit show, has product market fit? Because if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders and it lets us get better guests, thank you. Wayne, welcome to the show, man. Excited to have you here. 

Wayne Slavin (00:01:06) :
Thanks so much for having me on.

Pablo Srugo (00:01:08) :
Dude, so today Sure, I was looking through the website. It's kind of like an embedded insurance platform. Helps other companies have their own insurance offerings, is that right?

Wayne Slavin (00:01:16) :
That's right. We function kind of in the credit card industry. Kind of like a Visa and MasterCard. They are not the brand that gives you the credit card, and they're not the folks you buy stuff from.

Pablo Srugo (00:01:28) :
They're just the ones that make the money, yeah.

Wayne Slavin (00:01:31) :
They do have a good business model, turns out and so, yeah. We're doing that to help people build insurance programs and we'll get into the why later.

Pablo Srugo (00:01:41) :
And so, and walk me through how it. Because it started pretty different. It started on a flight as far as we talked a few months ago. But that's kind of what I remember.

Wayne Slavin (00:01:48) :
Yeah, the origin story was for me working in kind of payments and e-commerce. Thinking that eventually insurance would be sold like every other product we buy. Because why wouldn't it obviously be sold like every other product online, and the kind of inspiration to get into insurance did come from one of two places I think you come up with good ideas. One is in the bathroom, you can guess where but the other place is on a plane flight. It happened to be a flight to Vegas for a conference and I saw people on the plane who were just freaked out during turbulence. And I said, hey, wait a second, planes are super safe. I wonder if we could sell them life insurance right before the plane took off, and it came from a payments, and e-commerce company. That I was the VP of product at and said, hey, I'm gonna go try to build a prototype. And literally the zero to one of that was, on a long weekend I wasn't feeling well. Engineer by background and put together a prototype, knew nothing about insurance. Less than nothing about insurance and just said, hey, I wonder if I could use my skills from over here to sell insurance to people before they got on a plane flight.

Pablo Srugo (00:03:03) :
What does that prototype look like?

Wayne Slavin (00:03:05) :
From the basics, right? Go register a domain. At that point, it was WordPress. Site, template, slap something together that was purely focused on a singular offer and the offer was buy. In essence, life insurance before your plane took off. Tested three different offers, right? That cornerstone of e-commerce, you got your good, better, best. But we didn't even know if it was going to be, you know, $50,000 of insurance or $5 million of insurance and put that entire enrollment flow together. And spent some money, didn't have a bunch of money at the time, but spent a few thousand dollars on Google ads.

Pablo Srugo (00:03:44) :
All during that weekend?

Wayne Slavin (00:03:45) :
All in that weekend and, put that together with some Google ads and Facebook ads. Tested some positive ads of like, hey, leave money to your family in case something happens in your flight. To testing some not some positive ads, imagery of plane crashes.

Pablo Srugo (00:04:05) :
Did you have an easy way to segment for somebody that was going to book a flight or it was just wherever the algorithm puts it?

Wayne Slavin (00:04:10) :
Trusting the guys at Meta, trusting the guys at Google to target those folks, but what was fascinating after this experiment, right? Where we A/B tested different amounts of insurance and the messaging in the ads was, we ended up with a sweet spot of three offerings. And the middle offering with basically a million dollars of insurance. And we converted from click on an ad to enter in all your information about your flight, like what's your flight number, where are you going, what day, what airline, all of that. Who are you going to leave as your beneficiary to this insurance policy. Leaving them a message, which we have some interesting stories about that. All the way through to pay and so two things became interesting, but also were the evidence that confirmed I needed to go do this. One, from clicking on an ad to going through that whole process. Which isn't actually that simple. We converted fifteen point nine, one percent of people. Jeff Bezos would be jealous. We need to go start this business and number two was it was raw prototype. There was no insurance, we didn't actually have a product yet.

Pablo Srugo (00:05:20) :
Yeah, that's what I was going to ask.

Wayne Slavin (00:05:21) :
It was kind of like, today we do a waitlist, right? That's the common thing that Dropbox popularized, right? Make a waitlist.

Pablo Srugo (00:05:28) :
What year was this, by the way?

Wayne Slavin (00:05:29) :
This was 2015, 2014.

Pablo Srugo (00:05:31) :
Okay.

Wayne Slavin (00:05:32) :
And so what we did was when you hit pay, gave you an error and it looked like it was a payment error. You entered your credit card wrong and what was fascinating is we saw people coming back. Going through that whole process seven times.

Pablo Srugo (00:05:48) :
Wow.

Wayne Slavin (00:05:48) :
To try and buy it. And we were like, okay, if people are going to go through this whole thing multiple times, to try and buy this product. They actually need it and so that started the journey to say, okay, how am I going to become educated on insurance?

Pablo Srugo (00:06:03) :
How did you price it? By the way, just for that test?

Wayne Slavin (00:06:05) :
I think it was $19.99 for basically a million dollars or $9.99. It was one of the 99s, and we had tested it from 99 cents to even way higher. But that was the sweet spot of offer that ended up with that conversion rate. So that was kind of the okay, from this is a crazy idea to wait there's something here to, oh, shoot now I actually have to go do it. Because I proved it to myself.

Pablo Srugo (00:06:32) :
How clear was the signal for you? Were you like literally next week, okay I'm out, I'm gonna go do this or did you take some time to kind of think it through?

Wayne Slavin (00:06:38) :
For me, at that point, it was clear. The fear was real, right? You know, before you take that big leap, there's some real fear.

Pablo Srugo (00:06:45) :
Was this your first startup or you've done one before?

Wayne Slavin (00:06:47) :
It wasn't. So my first startups were when I was way younger, but also had less on the line, right? So it was kind of like, of course, I'm just going to do a startup. I don't know anything else, I've never worked for anybody but took a detour in my career to go work for some bigger companies that were trying to build new products, and so this was the step back into it's all on you kind of moment. And so I did some diligence, skeptical validation by reaching out to some other entrepreneurs. And said, hey, I don't know anything about insurance but am I wasting my time trying to innovate in insurance? It turned out no but in hindsight, it's way slower than you would have expected.

Pablo Srugo (00:07:29) :
I'm curious, how much you did worry about it in the sense that. I mean, it's an innovative way to sell life insurance. Because you're at this kind of peak moment of fear. The duration is really short, so actually the risk is really low. But for the user's perspective, oh, $20 to get a million, everything around it kind of lines up that I feel it would be an easy sale and obviously the numbers seem to show that. But how much thinking did you do about the ultimate business opportunity? Because the danger would be like, okay, this is cool, but also so copyable. Once I prove it out, you know, who else is going to sell insurance like this? Maybe everybody, right? And so how much did you think about that?

Wayne Slavin (00:08:02) :
Yeah, there were some deliberate thoughts about a couple of things. One, I did come from a company that was basically aggregating at the time a supply of basically different vendors and different products into one app. And we did learn from that experience that you needed ample supply in order to get people to want to interact with it. So we knew we weren't going to stop with one type of insurance. We knew that there was going to be multiple. But you clearly called out a couple of the dynamics that made this type of insurance a place where we could get insurance companies to come on board a little easier, right? Because they understood the risk, they understood the product they were selling, they understood a bunch of things, and they kind of knew that it's not like they're selling twenty year policies to people that they've never seen and it's completely different. It was really just a different distribution of something they were selling already. Which turned out to be one of the big factors to get our first partners on board. But we thought, incorrectly, that we were going to do you know the next insurance product through a mobile app and aggregate all these different insurance types in one place, and that people would come to that. And that this was just our beachhead of a first product to show validation to show support from the market the big insurance companies, and we did achieve that. But what we got wrong and, or I got wrong is our DNA is more about building product and tech. Less about marketing and customer acquisition. And in hindsight, my why is much more about helping other people build things versus us building a brand. And so we did make some decisions knowing always we were not going to do a single product. We also knew how to build the tech to not support a single product and so as we grew. Adding other products didn't require re-platforming, but also later on proved to be the thing that was the aha moment around our slow aircraft carrier type pivot. Rather than a 180 snap pivot, which was, hey, we built the infrastructure to do this. Why are we wasting time and money building it around our brand? That's not our skill set, we should go and find out what is our actual product market fit. And that was all about building insurance programs for other people's brands, but using our tech.

Pablo Srugo (00:10:33) :
That weekend, I mean, you're saying we a lot. But was that just you that weekend that Biddle does? And then how did you? Once you decided to leave then, did you get co-founders on board or how did you set up the initial team?

Wayne Slavin (00:10:44) :
Yeah, the initial team was very much folks that I had worked with at prior companies. So there were five initial team members that joined on. It wasn't day one, it was actually like day 366. I had been working on it for an entire year.

Pablo Srugo (00:11:00) :
Oh, you did a year solo?

Wayne Slavin (00:11:02) :
A year solo.

Pablo Srugo (00:11:03) :
Wow, okay. Why'd you do it that way actually? That's different and interesting in its own.

Wayne Slavin (00:11:07) :
I don't know if I would recommend it. I don't know if everybody can do it and I think it was probably more just around my skill set. Engineering to product and really more focused on business product. And launching kind of let me straddle the different roles that were needed and had some support but knew what I needed to do. Knew that it was all about building that prototype, knew it was all about finding our first insurance carrier partner and honestly. Wouldn't want to ask anybody to leave their job and put their financials on the line until this thing was, at least on stable footing. And so, managed to raise our seed round. And we're actually coming up on our ten year anniversary of the first team joining as, let's call them founding employees. It's in about seventeen days and so there we are. And basically, yeah, the first five guys were folks I'd worked with previously, and some of them in two companies. And three out of those five are still at the company ten years later.

Pablo Srugo (00:12:08) :
Bit of a tangent, but did you think it would take ten years plus when you first started this?

Wayne Slavin (00:12:12) :
Oh, no, no, no, no, no, no. There's no way you would, you would sign up for ten years, but I know. I know lots of investors and lots of successful founders. That have come before me as like, they have their sayings. You know, you might need to get kicked in the groin a few times, and like it in order to do this or you have to like the taste of blood. You know, cause you're going to get punched in the face. Stuff like that, it is absolutely a question of resilience and just keeping on going. But what's been exciting about this is that every year. I like to say, the company kind of gets reinvented, but not in a product way. Gets reinvented and reinvigorated through the conviction and the proof that we see that this is working. But I'd say in other industries, the ten years could happen in twelve months. I just happened to unknowingly choose an industry that a decade is equivalent to a year in other industries.

Pablo Srugo (00:13:09) :
You know, I think besides all the crazy one to a hundred million charts that you see these days. It is more like, even of the successful businesses. Most of them took ten years plus to actually get there. Never mind what you see in the headlines and all this stuff. This is more of the standard than not. So back to the story, let's go through that one year. Because you're working alone. Does that mean you didn't have to raise or did you raise during that year at all?

Wayne Slavin (00:13:30) :
I only raised at the very end. The raise was the, let's call it the launch party, slash, we're going to bring people into this and so that year was basically me dwindling down savings. And I was living in San Francisco at the time, and unemployed. Effectively, right? I wasn't employed.

Pablo Srugo (00:13:48) :
What were your, like, your key things that you wanted to de-risk in that year.

Wayne Slavin (00:13:53) :
The things to de-risk were kind of twofold. One was Seed round and two was do we actually have a product that could be sold, right? Because really what did I need engineers for, to go get an insurance company to be our partner, right? And so you could have been building stuff, but were you building the right stuff? Was that actually a good use of time, and so it was very much like, hey, how can we do this as leanly as possible. To have enough material to show an insurance company that this is viable, this is built, we will actually launch it. But of course, we're not asking them for money to do that. We're just asking them to be a supplier and distribute their product. And so once I had that in hand, which there's a whole story about that.

Pablo Srugo (00:14:43) :
Tell me that story, because I mean landing that first insurance partner is huge and actually it's similar to what it might take to land any enterprise. You know, outside of just insurance I would assume.

Wayne Slavin (00:14:52) :
Yeah, you never know where your first partner will come from. But one thing I learned in that period of time trying to get smart about insurance was insurance in the US, very complicated. Every state is basically its own thing, it has its own regulations, its own stuff. But you go to other countries and other markets, they might not be as big. But they are one market and one regulator. And so I went actually to South Africa, which had a bunch of dynamics. One, I'm originally from South Africa. Shout out to Elon and Roloff, and all the other South African tech guys. But basically went there and you'd say, well, why? Well, one reason is because it's one market, one regulator. It's also in English, had massive cell phone population, digital banking, very cutting edge and went there. And camped myself out for seven weeks to try, and go, and lead insurance companies, and get a deal done. And quite literally did do that. Left San Francisco to go spend seven weeks there. Realized in that moment we were going to actually found this thing and this was going to happen. And decided I didn't want to build the company in San Francisco. My now wife moved us to Los Angeles while I was overseas, and I flew back to Los Angeles instead of San Francisco. And came back, and said, OK, we're going to go launch this in South Africa. Mobile app can work anywhere. Got to figure out how to accept rand instead of dollars. But that's, kind of irrelevant and that first insurance company in South Africa. Provided the validation to go to the U.S. and meet with that same insurance company in the U.S. And say, we're already doing it with your counterparts. Why don't we just do it here? And at that point, things were built. It was live in the app store. You could show it, you could try it, it was real and so we're just de-risking every decision for people along the way.

Pablo Srugo (00:16:54) :
What did you have, when you convinced this insurance company in South Africa? What did you have to show them and how did you even get in front of them as a solo person, no brand, no money raised, no really credibility. Let's say, in the InsurTech space?

Wayne Slavin (00:17:06) :
Clickable prototype and some mediocre sales skills at the time. I'd say, no but what I've heard. Honestly, about that time, is passion, right? People could see the passion. This is not just somebody who says, hey, we're gonna do it. It's like, this is deep understanding of e-commerce. What it's gonna take to actually build this. This is truly an engineer, not somebody who's got to go hire people to build it. It's like, this is gonna be real. But also, putting myself in their shoes of like we're not asking you to spend a million dollars on us building it for you, right? Again back to that whole thing of they didn't have to build anything new. We were building everything. We just needed their product to sell.

Pablo Srugo (00:17:55) :
They're just underwriting, right? They're the underwriters ultimately?

Wayne Slavin (00:17:58) :
Yeah, and so it was that understanding that we just needed those nuggets of validation to get incrementally further. And I don't think I appreciated how risk-averse insurance companies are to tech. But it was funny, because also in that year. You asked what was I doing during that year, right?  The initial inspiration on a flight was insurance for a flight. But during that period of time I spoke to dozens of people who were like, no, but you should sell pet insurance. No, you should sell this insurance. You should sell that insurance and as I kept analyzing the dynamics around, are those viable options? Are they better go to market options? The answer was no. So ironically, the first product we launched was the lightning in a bottle idea product.  Even though it turned out that that wasn't the product that we're known for and that we even sell a whole lot of today. It was the one that let us get to market and I have no doubt people have awesome ideas. But get that analysis wrong of how do you get this thing to market and nobody's ever done it before.

Pablo Srugo (00:19:11) :
You're ran, you raised money, you get these people on board. How did you set it up, so those people would join you when you were ready? Were you keeping them informed throughout getting them to see the opportunity?

Wayne Slavin (00:19:20) :
Exactly right, yeah. What was I working on, getting their feedback on prototypes, helping here and there with the design of an ad. You know, how do we do eighteen variants? Of course, you know, at that time I could work my way around Photoshop. But a guy whose job is to be a designer is going to do that way faster. I could do the coding, but somebody who's proficient guru is going to do it better and so I was getting help along the way from friends. But they hadn't left their jobs yet and they ended up joining when I felt like I wouldn't be letting them down.

Pablo Srugo (00:19:58) :
It's a bit of a favor when they're working on the side. I mean, I'm sure they're earning something but it's not. You know, it's certainly not material to them and yet it's actually helping them buy in. And they're probably going to reach a point if things are going the right way. Where it's like, all right, dude, when can I, you know.

Wayne Slavin (00:20:10) :
Yeah

Pablo Srugo (00:20:11) :
I just want to do this.

Wayne Slavin (00:20:11) :
Yeah, exactly and that is kind of what happened. And that wasn't intentional, but my commitment to those guys was, I'm not going to ask you to do something that's risky. I mean, obviously every startup comes with risk, but I'm not going to ask somebody to leave their job pre-funding, right? Where it's like, oh, don't worry about it, the money will be here in a month. No, the money's here. Let's get started, I think that trend has continued true for me to our clients. Which is I'm going to under-promise and over-deliver. And that was basically it, right? We got to get this to a point at which I feel comfortable looking at people's family and saying, hey, yeah, I didn't promise you something. And then it just didn't happen, and blame some externality. Like, it's real, we've got time to figure it out and in reality, we figured it out. It just wasn't exactly what we thought it was going to be.

Pablo Srugo (00:21:01) :
How much was the Seed round?

Wayne Slavin (00:21:02) :
I think we ended at $1.6M, yeah.

Pablo Srugo (00:21:06) :
You know, now you got the people, you got the money, tell me about the launch.

Wayne Slavin (00:21:10) :
Well, the launch was actually at that point kind of anticlimactic. Because we've kind of been doing it along the way. There was, you know, a fun moment I remember of the true launch. Which again, you had to go to South Africa to launch it. Of course, because that's where we had product to sell and at that point we were launching the App Store. Good reminder, always check if you're using production API keys or sandbox API keys in your production app and that did happen. So we launched and had our Stripe keys at the time flipped around. And so none of the transactions were working. And we fixed that, and away we went. And had to go figure out how to acquire customers.

Pablo Srugo (00:21:54) :
And what was the flow? You'd get them on an ad. Let's say Google Ad, and then download the app to sign up?

Wayne Slavin (00:21:58) :
Google Ad, we actually had in a very. Let's call it guerrilla style. We actually had people standing at airports, yeah.

Pablo Srugo (00:22:08) :
You might die today.

Wayne Slavin (00:22:10) :
Yeah, you laugh about it but no literally you got to get people at high intent, right? The whole point was the context of buying insurance and so the prior company that I was working with was all about contextual commerce, right.? Like hey, I'm here, what can I buy? And that company had won TechCrunch's most innovative company of the year 2013, it was called Topingo. There was a book written about us, and we were selling products on college campuses to college students. And we had created this unbelievable ecosystem. And so one of the things we realized was, we could acquire customers literally while they were standing in line to come in and download an app. Register for the app. Make their payment and transaction happen before the guy or gal standing in front of them in line did it in real life and so we kind of replicated that. We knew it worked. We knew that this was something brand new. Nobody had ever bought insurance before you got on a plane flight. But where are you going to find them? You're not going to find them at their hotel. You're going to find them in line at the airport, waiting for their bags to be checked.

Pablo Srugo (00:23:18) :
And what was it thinking of the mobile app, by the way? Versus just being like a website? Isn't that faster?

Wayne Slavin (00:23:22) :
Oh yes, that's a great question. We wanted location services on, so that you're doing a round trip. So you're going to fly somewhere and you're going to fly back. We wanted to be able to push them a notification to buy it again and so we had every airport in our backend system. Every airport had a polygon drawn around it for location. Turns out it's actually at the time, way harder to draw a polygon versus a circle radius around an airport. But we had built that capability previously and so when somebody arrived. We figured out the exact amount of time, I don't remember it offhand anymore. The optimal amount of time to wait, to send them the push notification, to get them to buy again, right? You don't want to hit them as they're getting out of the car, out of the cab, out of the Uber, and they're waiting in line trying to get their boarding pass out. And they see this notification, and they dismiss it. I want to say it was like twenty-two minutes after arrival, was the optimal time to push somebody a notification to do that. But yeah, that was that was fun times, man. But that was a short lived period of time to get a product to market.

Pablo Srugo (00:24:37) :
How well did that go? Your test in the weekend was like off the chart. So I assume this was proportionally much better.

Wayne Slavin (00:24:42) :
Yeah, I mean it certainly worked. It was a different market. Didn't have that same acquisition channel of Google and Facebook at the time.

Pablo Srugo (00:24:50) :
Why not?

Wayne Slavin (00:24:51) :
Different area, different demographic, different customer market, right? Versus the U.S., there were just some differences.

Pablo Srugo (00:24:57) :
How interesting.

Wayne Slavin (00:24:58) :
In customer behavior and targeting. That was the start and then that led us on the path that we're into today. Which is obviously a much bigger TAM, much more exciting, but you can never forget how you started.

Pablo Srugo (00:25:10) :
How long did you stick with that product for?

Wayne Slavin (00:25:13) :
Probably a year and a half. That was the focus.

Pablo Srugo (00:25:16) :
How big did you get in that year and a half?

Wayne Slavin (00:25:18) :
Yeah, it was tens of thousands of customers, had downloaded and we had repeat usage statistics, and all of that stuff. But the policies we're selling were dollars, right? It wasn't like tens of dollars.

Pablo Srugo (00:25:32) :
Yeah, and the split is what? If you sell a $20 policy, the insurer gets the bulk of it, I assume.

Wayne Slavin (00:25:37) :
You're getting a small percentage of that as true revenue.

Pablo Srugo (00:25:42) :
Was that the main problem then? With this product?

Wayne Slavin (00:25:44) :
No, I wouldn't say it was the main problem. You could go build a business around that. There are companies today that just do travel insurance, in essence a souped up version of this and they do quite well. But they're not sticky, right? There's no retention, it's a one time transaction, people don't need it. There's a subset of people that are going to think this is unnecessary. There's a subset of people that are like, eh, maybe if I'm flying somewhere, you know, on an airline I don't trust or a trip that's pretty remote. Maybe I'll buy that and then there's people that will buy it all the time.

Pablo Srugo (00:26:17) :
It's also, I would think, a race to the bottom, right? I mean, at the end of the day. If somebody sells me a million dollars for ten and somebody for twelve. Look, I'll take the ten all day. Why not?

Wayne Slavin (00:26:24) :
It's a total commodity, exactly. So not that exciting and so we today, at Sure. We do, you know, we make insurance really easy to buy. But we do it in the most complex types of insurance. Auto insurance, home insurance, business insurance, life insurance and so where we figured out. And really nailed our why, and our mission was we were really the best at the tech to facilitate the transactions. And that part was where we differentiated. And really started the journey going from a direct to consumer mobile app, to being the infrastructure and solution for building. Let's call it, enterprise-grade insurance programs for the Fortune 500 and that's what we do now.

Pablo Srugo (00:27:14) :
We have tens of thousands of people who have followed the show. Are you one of those people? You want to be part of the group. You want to be a part of those tens of thousands of followers. So hit the follow button. I always think there's kind of three paths, right? You put out a product, nobody buys it, you're like, okay, we've got to do something else. Put out a product, it's amazing, the business model's great. You're like, cool, this is a thing, I'm done. I'm done really thinking, right? Until it plateaus, or you're in this gray zone where some things are right but some things are wrong. Which sounds more or less where you were. Where people were buying it, but you knew it was a bit of a commodity. The dollars per sale were not that high. But how do you go from. First of all, where are you at, at this point? Did you raise an A? Or were you still in the Seed round? And second, what steps do you take until you end up, with the business model you have today?

Wayne Slavin (00:27:56) :
So post-seed, pre-A, we kind of realized that we were going to pivot to what today some people call embedded insurance. You could think of it just like embedded finance, however you want to view that.

Pablo Srugo (00:28:10) :
Is effectively selling insurance at the best possible time, is kind of how I think about it.

Wayne Slavin (00:28:15) :
Exactly, but through somewhere else where they've already acquired the customer, right? Because even on a small dollar thing. Small dollar things work really well if you have no CAC, right? If there's no cost to acquire that customer. Sell a dollar thing all day long, no problem but when you have to go acquire the customer and they're not repeat, and it's not recurring. Man, that is, that is hard.

Pablo Srugo (00:28:36) :
And it's in a sense no longer a commodity. Because you're not really competing with the other, since it's part of some flow and so it's kind of it becomes a check. Well, yeah, I'll buy it here and done.

Wayne Slavin (00:28:45) :
Exactly right, and so we had started to build that capability. Find our first partners in a different product entirely. So not in that type of insurance and frankly in renters insurance for people who are moving into an apartment.

Pablo Srugo (00:28:59) :
Who are you working with for this new model?

Wayne Slavin (00:29:02) :
Property management software platforms, places that you find an apartment online, stuff like that where you pay your rent, etc, and so we built. You know, all the APIs, different ways of integrating with us, to facilitate us and them integrating in a really easy way. And so we had started that. While continuing and maybe that's an unorthodox thing but while continuing to support the mobile app strategy. Before we just said, hey guys, you know, you're an Android developer. You're an iPhone developer we don't need that anymore. We're gonna completely shut that down. We're gonna go build a bunch of APIs and websites to do embedded insurance. I hadn't proven the embedded insurance thing yet. So we kind of kept the one thing going while validating the second thing and eventually just kind of slowly. A sunset the mobile app as the embedded insurance distribution ramped up and then that gave us the proof to say, OK, well, we can do it for ourselves, we can enable partners, we can sign partnership deals, that's a whole new motion, right? It sounds trivial to go from people in airports driving app downloads to signing enterprise contracts. But you have to be sure you can do that, and that is a skill in of itself. And so we added a few more distribution partners. Started to see the conversion work, the economics were far better, and eventually moved to just focus on that. And that led us to realizing from really customer feedback. That not only did brands, meaning these guys effectively were brands, right? They built a brand for rent payment. They built a brand for finding an apartment in San Francisco. They had the customers. They wanted to add insurance to improve their customer experience and their products. But also the insurance companies that we were using to support and underwrite these programs. They were like, well, wait, we need a platform like that too and so we started to actually sell software as a service license to our platform that we had built. To support ourselves and then now licensed to other people for them to build their own insurance programs. And effectively, that's what we do today, which is we are the software solution for the insurance companies. If they want to do it on one end.

Pablo Srugo (00:31:33) :
For embedded insurance or for any type of insurance? Like on their normal website?

Wayne Slavin (00:31:37) :
Any type of insurance that you want to transact via fully digitally. But what we're specialized in, a category of our own, is helping Fortune 500, Fortune 100, consumer and B2B brands embed insurance. So we've done that with some of the biggest brands in the world. Folks like Tesla, Toyota, Better.com, MasterCard into it. Really some of the biggest brands that they have millions if not billions of consumers and have never been able to figure out insurance. But insurance is really important to their customer and so effectively, we don't just operate like what I talked about in the intro. Like a Visa or a MasterCard, you know, the rails to connect those two. We are actually the full end to end. We're the front-end transaction layer inside of a brand, like a Toyota auto insurance and we are the back end software, and payment, and everything for the insurance company. And underwriter, to enable it. And, you know, today the hypothesis is pretty obvious. We can explain it, more simplistically than ever before and it's a pretty simple thing for people to get why this would be a thing. And it's, I draw to credit cards again. Not from the Visa MasterCard standpoint but from the growth of consumer credit cards. I'm sure you've got a handful of credit cards in your wallet and the interesting thing about that is that over the past twenty years. The big growth in credit cards for consumers has not been credit cards that are branded as Citibank or branded as Capital One. It's been in credit cards that have been branded as the Amazon Prime card, the Apple card, the Marriott card and the greatest card of all time. The Delta Amex card, and that has been where consumers have decided to put that card in their wallet. And even today, if you told somebody twenty years ago that the Delta Amex card would be one percent of the GDP of the US being spent on a airline credit card. They would have said, that's insane, it'll never happen but it turns out that that is exactly what happened and so if you look at how consumers have behaved with their credit cards. Where they have chosen to go for brand affinity, right? I'm a Costco shopper, so I want the Costco credit card. It makes sense that, that same thing would happen in insurance. I'm buying a Toyota. I'm going to get my insurance from Toyota, because I've made a choice to affiliate with that brand. Same thing is true if I go on Zillow or I go on Redfin, or I put my house on Airbnb, or I do my accounting through QuickBooks. You've made a much bigger choice than, hey, I'm going to get my insurance from company XYZ. So do you really care that Amex is behind the Delta card? Not really, you care that it's a Delta card, right? And so that's been shown in consumer behavior.

Pablo Srugo (00:34:43) :
It makes sense. I mean, you're taking what is effectively a commodity. You think about the credit card, everyone's going to give me the same amount of credit and they're going to give me the same interest rate. And the difference is, A, where is it easiest to buy? That's one of the big things and the other one is either actual or perceived value. Which is like, if I'm Delta, I'm going to tell you, you know, you get X more points and all this stuff. And if I'm already a Delta customer, that just means a lot more to me than the generic point five percent cash back or whatever points that some bank's going to give me. That I'm trying to translate into what that's going to mean for me. So it's like, maybe that is actually better value or maybe just perceived value, but it's also way easier to buy. Bit of a no brainer, same with embedded insurance. I think it's kind of the same thing. Like you said, if I'm in Toyota, I'm buying it, it's right there. Why am I going to go shop around at the dollar size relative to the bigger purchases in that big anyways? And they might actually be a better offering potentially, or at least I might think it is and so all that stuff leads you to just transact right there.

Wayne Slavin (00:35:34) :
Exactly, better integrated, right? You know, what's the true value of being able to earn status on United a little bit faster, right? Like the value, the cost to them of that is way less than, the perceived value to the consumer. So even if it's like, hey, I don't have to download the progressive mobile app. Because I already have the app from my car maker and I can just see my insurance in there. Even that convenience factor is huge, right? And that is just true across a lot of disruptive shifts is, it's just convenience ease and removing the friction for the consumer. It doesn't have to be fifty percent cheaper. It doesn't have to be two hundred percent better. Because to your point, it's like, well, if all credit cards are approximately the same interest rate and I'm getting approximately the same features in my credit card. Then how am I going to choose? Well, I'm just going to choose the one that's easiest because I already have a Delta account.

Pablo Srugo (00:36:37) :
By the way, just take you back to the story. When you decided to go down this renter's insurance piece. Can you just tell me about the first kind of key partner and then what did that launch look like relative to the direct consumer offering? How much better was it or in one sense was it better? Because ultimately that's what led you to go chase that.

Wayne Slavin (00:36:54) :
I'll tell you about the first, first, first launch that didn't go well. So our first partner was a company that is no longer around. It was a company called Onerent. They were doing some awesome stuff. They were in LA, we were in LA, we were super close to launching. They went out of business the week before we were supposed to launch and they were like our launch partner.

Pablo Srugo (00:37:15) :
That's brutal. Dude, that's just, by the way. One of the things that's with startups is everything's so hard and then on top of that. You have things that happen that you would never have imagined, is the thing that gets you tripped up. Like some macro in this case, like your partner going out of business. Are you serious? You're like, I've got so much done to get to this point and then this.

Wayne Slavin (00:37:32) :
Yeah, no, we had done everything. It was like everything was done and so that was just like a, oh my God, are you serious? That's really happening and this is obviously at a critical time. You've got, you know, as a startup that's been funded. This is, you've got a board, you've got a, you've been telling them that this is going to happen and then this externality goes on. And I've got hundreds of crazy externalities where you're like, there's no way that happened. And it happened even to us a few days ago. Where you're like, there's no way that happened. You worked on something for a year, and then it gets greenlit. And then three days after it's greenlit, the person on the other side takes a new job. And you're like, well, how can that be? And so those ones, I think give you character. Those are the ones that's the punch in the face stuff. That you just got to persevere through. There's no other way to deal with it.

Pablo Srugo (00:38:32) :
So what was the first good launch then that actually made you wanna go down that way?

Wayne Slavin (00:38:36) :
I don't know, because you remember your first. I don't remember who the first successful go live was. But we very quickly, after doing that first one, right? Where you're building the APIs, you've never done this before, you're getting the lawyers to drop this contract that you've never had before. Those ones take the longest and actually it's really important. You can't underappreciate having a, let's call it a cooperative, reasonable, practical partner that can help understand. They're the first that makes it a lot easier, but once you've got that framework in place. We rapidly went and acquired a bunch of other customers, and partners.

Pablo Srugo (00:39:19) :
How quickly did things ramp? How quickly did you get to a million in revenue? $10 million in revenue sort of thing?

Wayne Slavin (00:39:23) :
Pretty quickly to a million in revenue and the thing that was underappreciated about Renter's insurance is it was quite cyclical. It peaks in the summers and it's quite slow in the winters. And so those are some of the seasonality things you don't necessarily know about every market and every product. But it was quite big. So we got to a million faster than I expected.

Pablo Srugo (00:39:46) :
In a year sort of thing?

Wayne Slavin (00:39:48) :
Yeah, I think even, even faster than that in terms of ARR and then just continued. It never went hockey stick for that line of insurance. It's just continued to compound, year over year, continued to grow and even today, I think, this is the end of the month. Grew exactly on target for, a renter's insurance book of business. But the thing that actually went vertical line for us, was auto insurance. Obviously, bigger ticket item, right? You know, tens of dollars in renter's insurance, right? We went from single-digit dollars to double-digit dollars to triple-digit dollars and auto insurance. We had that validation with the biggest AV brand of them all. Where there was just, a stampede of demand for easy to buy auto insurance for that company and that was. I think the thing in my brain that crystallized, oh my God, this will not just kind of work, this will truly work. To the point at which we will build the next $10 Deca billion insurance brands will be built by Sure. Because of what we saw in auto insurance with that AV brand and basically everything I've done since then, 2019. Has been focused on how do we go get the world's biggest brands to build insurance programs with us. But in a way where every year I kind of talked about we reinvent ourselves. Every year we've gone from, hey, we're going to give you the software to do this and maybe we'll do a little other piece of it. To at this point in 2026, we literally can go to the world's biggest brand. You name it, I mean, I don't know what we could do with Jensen and Nvidia, but we'll figure out something to do with them. But, you know, an Amazon, an Apple, a Toyota, a Tesla, anybody. We can go to them and say, hey guys, we have every single piece to launch your own insurance business in one place. You do not need staff, you do not need software, you do not need balance sheet, you do not need a capital partner, you don't need anything. We are a one-stop shop to do that for you and we're the only guys who've done it for that size company. And so that has been an incremental thing over the past six years going from just software to software, and implementation to operations to balance sheet to underwriting literally every piece of it. And, so yeah well we function as the rails. Because nobody's ever done this before. This is not a situation where someone says hey we're going to switch from one type of manufacturing to 3D printing these parts, or we're going to have our own warehouse versus outsource the warehouse. Where they kind of know what to do. They've never sold insurance before. They don't know how to underwrite insurance. They can't go to their CFO and get a billion dollars out the gate. When they've sold precisely zero policies and have zero customers. That's just not how business works and so we've built this unique model. Where we can stand up an insurance brand for a Fortune 500. They market it effectively, that's like their thing. That's all they need to do. We make it work like the Visa MasterCard thing and we have all of the balance sheet. Capital partners to effectively take that risk and underwrite it. And everybody gets what they want. And so it's a pretty simple hypothesis back to that thing. Where we've seen the dynamics of consumers want to buy from the brands they trust. We also know that capital providers, right? Investors, not VCs, sovereign wealth funds, private equity, want insurance returns, they love insurance, right? Warren Buffett is the best example. It can't be that you don't want to be involved in insurance economics. If the Oracle built his empire on insurance and guys like Apollo want to own insurance income, and BlackRock, and KKR, and all these guys want to do it. So why wouldn't we go help people expand that market and launch new insurance brands. And that's been just a little bit of a leap of faith each and every time. Being like, all right, I guess we got to do it.

Pablo Srugo (00:44:31) :
By the way, last question before we do kind of our ending set of questions. So you've raised like $120 million or so, but the last time you raised it was 2021. What's made you decide not to raise in the last four years?

Wayne Slavin (00:44:40) :
I think, being financially responsible. So we ran it and have run Sure, I think, a little bit differently. I'd say more private equity-esque than venture-esque. So when we raised our Series C in 2021, we had every dollar of our Series B in the bank still and we were actually profitable, net income positive, not, you know, community adjusted EBITDA or some weird thing. We actually were profitable, and that was in 2021. And people were like, ew, what is profit? But it turned out that that was a good discipline to have. We have been investing, right? I talked about this journey of really taking over more of the supply chain, so to speak. We have been investing that $100 million diligently. So that we can be where we're at today and I've always just wanted to control our own destiny. And it's hard to control your own destiny when you're starved for oxygen, right? You don't tend to make the right long-term decisions. So I haven't needed to raise is the real answer. Even though I could certainly do more interesting things if you did raise but TBD, stand by for some cool stuff. 

Pablo Srugo (00:45:54) :
Perfect. Well, listen, we'll stop it there. Let me ask the last three questions you always end on. The first one is, when was the first time that you felt like you had true product market fit?

Wayne Slavin (00:46:03) :
End of August 2019, there was a tweet from the chief tweeter, and a program launched. And it was a rocket ship. Literal rocket ship of insurance, transactions, sales, and it just was like, oh my God. If you have the right brand and the right product, in the right place. This is going to be billion dollar business before we can imagine.

Pablo Srugo (00:46:29) :
It's interesting how there's different levels of PMF. Because you had little PMF in that first weekend, a bit more in South Africa, another one with renters and then there's the Elon Musk piece. Which was just been like completely different order of magnitude.

Wayne Slavin (00:46:42) :
Yeah and I don't think anybody can repeat that. So, your high highs should not define all the average of your days, but that was certainly like a, oh my God, this actually will work and we just kind of got to wait for the market to catch up. And so, not everybody can have that moment, but in spite of that. We've continued to incrementally go and some of the programs we run today. We no longer work with those guys, but some of the things we do today are even bigger and they didn't come out the gate that way. But it was unbelievable conviction confirmation.

Pablo Srugo (00:47:18) :
Was there a time in the journey where you actually thought things might not work? And maybe things would just crash and burn, and fail?

Wayne Slavin (00:47:26) :
Everyday at 4 a.m. when I'm awake in my, basically bed. Yeah, everyday, man. It's one of those perpetual things and I don't know if that's just my skeptical nature or, you know, paranoid nature. But I have to remind myself, our clients can't let us not succeed. Because their success is dependent on our success.

Pablo Srugo (00:47:49) :
I always thought once you became profitable, that anxiety kind of went away a little bit. Sounds like not the case.

Wayne Slavin (00:47:54) :
No, there's always something that you're worried about, right? Your team, your customers, you lose a champion at your customer, right? Things change, right? Even, you know, in every business there's other problems you wish you had, right? I'm sure for folks who have subscription businesses to consumers, they wish they had long-term enterprise contracts. I've got long-term enterprise contracts from few big companies and that gives you a different problem, right? Of you have few customers but they're really big and you wish you had more customers. So that if you lost one it doesn't hurt as much, right? Or a faster sales cycle, or whatever and so there is always something weighing on you. And, you know, maybe that's just how I keep myself focused.

Pablo Srugo (00:48:40) :
Final question, if you could have one piece of advice. That you'd give your younger self ten years ago and you're just turning this company out. What might that be?

Wayne Slavin (00:48:47) :
I would still start it, I would still say go do it, and I would say do the exercise of finding your why sooner. Which helped keep it really clear that the model we do today, is like so perfectly aligned with the things that keep me energized and have almost none of the dynamics that are draining to me. In terms of marketing and dealing with end consumers, and stuff like that. It's like I want to be working with and supporting other people's programs. So I would have just said, do that exercise. Shout out to Simon Sinek, right? Do that exercise sooner and we would have saved a bunch of time.

Pablo Srugo (00:49:33) :
Perfect. Well, Wayne, thanks so much for sharing your story, man. It's been great.

Wayne Slavin (00:49:36) :
Yeah, thanks so much. This was a lot of fun.

Pablo Srugo (00:49:38) :
Wow, what an episode. You're probably in awe. You're in absolute shock. You're like, that helped me so much. So guess what? Now it's your turn to help someone else. Share the episode in the WhatsApp group you have with founders. Share it on that Slack channel. Send it to your founder friends and help them out. Trust me, they will love