225: Selling for 10x by Building What Customers Have to Buy with Will Caldwell

You don’t need to create demand if demand is mandated.

That’s the insight Will Caldwell used to build and sell his company.

Will discovered that inside the mortgage industry, banks are legally required to buy flood certificates on every loan. So, he started Snap — a platform that makes it faster and cheaper for banks to do exactly that.

Then he partnered with Intercontinental Exchange, the $95 billion company that owns the New York Stock Exchange, plugged into their existing infrastructure, scaled quickly, and eventually sold 51% of the company for 10x.

In this episode, we break down how to build within regulated industries, tap into existing demand, and scale without chasing customers.

Mic Drop Moments

• “Fat cats don’t hunt.” – Will Caldwell

• “Find an entry point where you can help them either lower their costs on something they absolutely have to do.” – Will Caldwell
  

• “Spend more and more time with customers, making sure they’ll actually pay you.” – William Caldwell

• 00:00 Small Teams Beat Large Companies
• 01:32 Why “Fat Cats Don’t Hunt”
• 02:35 Starting His First Tech Company
• 05:59 Knowing When to Shut Down a Business
• 06:29 Turning a $100 Compliance Headache Into a Startup
• 09:21 Finding Opportunity in Regulated Industries
• 17:41 AI Underwriting
• 22:20 Scaling via Strategic Partnerships
• 25:53 Selling 45 Banks in One Month
• 34:07 Selling to  Intercontinental Exchange for 10x
• 35:19 Why He Sold Only 51% of the Company
• 38:44 Don’t Build the Tech Until You Have THIS
• 42:40 What Post-Exit Life is Like
• 43:50 What Will is Investing In Right Now
• 45:27 Advice for Entrepreneurs Starting Today
• 45:57 Books That Have Shaped His Thinking

Brad Weimert: Kite surfer, snowboarder, property technology founder multiple times, most recently, you sold your company to a billion-dollar company. Will Caldwell, welcome to Beyond a Million.

William Caldwell: Thanks for having me, Brad. Excited to be here.

Brad Weimert: So, let me start with this. A massive kiteboard jump or closing your eight-figure deal, what produces more adrenaline for you?

William Caldwell: Oh, man. Yeah, different stages of life, but there’s nothing like a huge kiteboarding jump during like a hurricane. It really gets you buzzing.

Brad Weimert: During a hurricane? Is that actually a real time you go out on a kiteboard?

William Caldwell: Yeah. I grew up in South Florida. So, you watch the news, and you see the kite surfers and the news anchors are saying how nuts those people were out there during the storms. That was me.

Brad Weimert: Wow. That sounds crazy. So, you had a relatively small team. With 30 people, you outpaced quite a few much larger companies, billion-dollar companies that were in the same space. What do you think the biggest advantages of having a small team when you’re competing against a giant?

William Caldwell: You’re at Nimble. You can ship product faster. We play in a sandbox that is primarily owned by private equity. And so, what we’ve observed in our world is once that happens, a lot of the top talent leaves, and the incentive for the people that are innovating there are gone. So, you just have kind of a carte blanche if you’re hungry to go out, innovate them. And I always find that in this scenario, fat cats don’t hunt.

Brad Weimert: So, another piece that I think is interesting, I want to back out to your story arc here, but I think this will bring us there. You have largely been in a technology company, in technology-based industries, but you purport to not be a technical founder. How do you think about building software as somebody that isn’t a technical person?

William Caldwell: I think about winning on the edges. I think in our world, we’re in vertical SaaS. So, it is just how does it fit within the market? How is the margin profile? What is the competitive landscape? And how do we get a wedge into the market? And just that was how I kind of jumped in. I wanted to be primarily in a space that was an established P&L item. And that’s just where I got started, kind of jumping into how I got here today.

Brad Weimert: All right. Well, let’s back out then. So, the first thing that you launched into that I was aware of was Dizzle, which was a mobile referral app that helped real estate agents do their business. Give me an idea of, well, actually, so give me an idea of what that app was and tell me about the arc there, because everything I saw was kind of you got to a point where you felt like you plateaued, and then you stepped away from that. Before we talk about that transition, what was the app? What was the ambition from the beginning there?

William Caldwell: I was in college, and it was around 2012. The App Store was really coming online, and it was just exciting time. I was out in California, and people were building apps, and I just wanted to be a technology entrepreneur. It just seemed fun. I was kite surfing, and there was guys that were all technology entrepreneurs, and I was like, “I want to be just like them.” So, I didn’t really care what I was doing, and I was an accounting major, and that wasn’t it for me. But my mom was a real estate agent, and so we started building what we called like the Liz Caldwell app. And one of the features in that app that she wanted was if I move to say she’s in Fort Lauderdale, I want to know Liz’s recommended referral like service providers.

So, roofer, handyman, home inspector, things that you need, but the realtors, since they do so much business with these service providers, the service providers want to make the realtors happy, and so, usually get a higher level of service. And so, that was a really valuable list. And realtors would give it to their clients. “You’re in a new city. Here’s all my people. Call them. Tell them Liz referred you.” And so, we put that in the Liz app. It was a white-label app, and realtors could give it to their clients. And it was successful, but it just wasn’t taking off. And so, that’s kind of how I got into the game.

And what we learned was those service providers will pay a fortune to get in front of real estate agents. And we started charging advertising on our platform, and some of these vendors were paying us like outsized amounts of money. And I was just like, “That’s incredible. Need to be in that business.” Because on the digital business, we were selling agent by agent. It was like trench warfare. Churn was high. It was not a hill I wanted to die on.

Brad Weimert: So, you were selling directly to agents or reselling to brokerages?

William Caldwell: I was selling to both, but it was just tough. They didn’t spend a lot on technology. They didn’t value it. It was a tough business.

Brad Weimert: Yeah. Well, I think the reason I wanted to hit on that briefly because Snap is the big chapter, and I think you’ve got a whole bunch of different interesting narratives to go down with the experience with Snap, but one of them is just the decision to get into it. So, you started with Dizzle, and you’re targeting agents, and it sounds like some brokerages, which as you pointed out, you’re doing one sale at a time, and you also have high churn in that space. And your client is the agent, right? And that’s who you’re trying to get to pay for everything. You moved into Snap.

So, actually, before the transition, how did you decide to sunset a business? I mean, the reality I think for most entrepreneurs, not all, but most entrepreneurs, once they have enough sunk costs into something, they’re just driving that lane and trying to figure out how to make that thing work. And they sort of are blind to the possibility of just closing it and moving on to the next thing. So, how did you come to that choice? Was there a key moment that led you there? What was the emotional process like for that?

William Caldwell: Yeah. The business was really tough. Like, I was about 18 months in. I had raised about $400,000, too. So, I had investor money, and it was just like, but it just wasn’t something I wanted to do, or it wasn’t going to take us to the promised land. And the aha moment was when these vendors that were advertising on our platform, we called them, and one of them said, “Why do you want to talk to us? All we do is sell a hundred-dollar piece of paper.” And I was like, that was a light bulb moment. Paper doesn’t cost $100. This product is required on every home sale in California. Realtors like loved our product. And so, the light bulb went on like, “Hey, let’s just basically give Dizzle away and make money on all these required products.”

And so, we sunset Dizzle, rolled the investors into the new company, recapitalized the business, so no bad blood. And that turned out to be a really smart decision later on. But I never burned a bridge, and that was really important to me when we shut that business down. So, everyone was cool.

Brad Weimert: Yeah, I love that. In general, I definitely know founders that take money kill the company unapologetically, and say, “Hey, you knew what you were getting into,” which I think is some asshole sh*t. Legally okay, I suppose, but bad blood indeed.

William Caldwell: I never lost anyone money, and I’m pretty proud of that, so.

Brad Weimert: So, Snap was born from a compliance headache that all lenders have to deal with. Explain what a flood certificate is and why they’re mandated, because nobody knows what the f*ck that is unless they’re in mortgages in general.

William Caldwell: Well, before the flood certificate, we started out with what was called a Natural Hazard Disclosure Report, and it’s think CARFAX for your house, but it’s required on every home sale in California. It basically tells you the fire, flood, earthquake risk associated with that property. What we did was aggregate all that data ourselves. So, we had no middleman from data aggregation to distribution, and we were very intentional about that from day one. So, we’re kind of a data business with the distribution arm.

Brad Weimert: And this was originally one of the vendors for Dizzle?

William Caldwell: Yes. This was California-specific, very niche cottage industry. But just, “Hey, $100 paper doesn’t cost $100,” so we got the cost of these reports down to pretty low, under $10.

Brad Weimert: So, I think first and foremost, compliance-related things sound boring as sh*t.

William Caldwell: They are.

Brad Weimert: Second, I think most entrepreneurs when they see a compliance industry and when they see, hey, there’s this regulated thing that’s mandated by anybody, by X, Y, Z, in this case, mortgages, and the powers that be behind mortgages, Fannie, Freddie, I would imagine, I would think immediately most entrepreneurs would dismiss that space because they would think it’s too complicated, too much, too many established players in the business, and they don’t want to deal with it. What gave you the confidence to dive headfirst into that market and say, “Hey, this is what I want to actually tackle”?

William Caldwell: Well, I knew when I looked at the hazard business in California, I knew our competition really well because they were advertising with us, and I just was convinced they were not that sophisticated in terms of technology. Again, it was that fat cats don’t hunt mentality. They’re regulated their way into a market-leading position. And the industry wants modern technology, like people are willing to pay for that, and then switch off their legacy provider.

Brad Weimert: Do you think that’s true of most industries that are focused around regulation?

William Caldwell: Absolutely. There’s a recurring theme,

Brad Weimert: So, if you’re an entrepreneur that’s looking for a vertical to dive into or looking for a space to play in, how do you think people should learn about a regulated industry to see if it’s worth tackling?

William Caldwell: Find an entry point where you can help them either lower their costs on something they absolutely have to do, is just a fantastic way to break in. Because once you’re in and people like you and trust you, it’s so much easier to sell them a bigger ticket item or the next thing up the food chain. It’s just a lot of these regulated industries are very relationship-driven, belly to belly, so people got to like you. You need to get that momentum going. And you do that by just start with something small.

Brad Weimert: How do you think about distribution from there? And give me an example of something small.

William Caldwell: Well, like the flood cert, it was required on every loan. It sells for $6 to $15 a loan, but required on every single loan, refi, and HELOC in the United States. So, they have to do it. They’re doing it already, and they’re open to like saving some money on it and automating it. And so, it wasn’t automated at the time. We were running it through legacy infrastructure. And make legacy infrastructure easy was like a huge learning point.

Brad Weimert: So, back out on that and give me some of the specifics for this because I think when people hear some of these things, we’re talking about kind of the high-level components, but where does the rubber meet the road on this? So, you look at legacy infrastructure, and I think what I’m hearing, but I want to get to kind of names and who’s doing this and how you got into it. But when I hear legacy infrastructure, I’m thinking mortgage companies use some kind of software, and within that software, in order to do a mortgage, you have to get a flood certificate, and somebody is providing that certificate and is tied into that software. And so, you somehow weaseled your way into that software. That’s kind of what I heard.

William Caldwell: That’s what we did.

Brad Weimert: So, that’s what you did. So, like, give me the path to doing that because not only does it seem daunting, but it also is an unclear path for people. Like, if I want to become integrated to Oracle or Salesforce, and Salesforce has a marketplace that’s a little different, but be a preferred provider, there’s lots of competition in that space. Or like you said, it’s a belly-to-belly handshake proposition. And I would also think with something like a flood certificate, they already have a thousand providers, and it’s only a $6 play. So, who cares? So, how do you get into that relationship, and how do you make it work?

William Caldwell: Look, you’re not wrong. It is a daunting task, I think, to get into any of these mega infrastructure companies. The story was I got introduced to the head of partnerships with what is called Ellie Mae Encompass, which is now an ICE company, in San Diego. But we were lucky in the sense that the advantage we saw was the legacy players, they’re all trying to migrate and go to the cloud, get off desktop, like get to more modern technical infrastructure. But what that means is they have to then pull all their partners, who are also legacy companies, to the cloud with them. And so, we were at the right time, like timing is everything still. They were really struggling to get new providers or companies to come to the cloud.

And so, at the time that we got introduced, we were the first company to be on their new cloud partner connection, like partner network. And so, that was the door to get in. Otherwise, yeah, it would’ve taken two years to get through the door, but we kind of got like expedited when we got that intro to the partner person at Encompass. And then that’s kind of how we got our foot in.

Brad Weimert: I’m going to get back to that in a second, but what was the, ultimately on exit, how many of these massive platforms did you have that you had tied to? Or was it all driven through one platform?

William Caldwell: It was just driven through Encompass. They have about a 60% market share.

Brad Weimert: Jesus.

William Caldwell: Yeah.

Brad Weimert: Well, who is building the next platform that disrupts that?

William Caldwell: The people are going after it. It’s just banks are slow, and once they like die on the hill of like, “This is who we’re going to originate mortgages with,” to switch a mortgage platform, that is like you might get fired if the things go, you will get fired if things go sideways. So, it’s people’s job. It’s a mission-critical decision. And so, they’re very entrenched in the space.

Brad Weimert: Yeah. That makes complete sense on that front. So, you said something that I think is super relevant to today, which is right time, right place, as legacy players wanted to go from the desktop to the cloud. In April of 2026, we are in the very beginning of people wanting to go from decision-based frameworks to AI. And so, we’ve got a huge window here, and everything’s moving tremendously fast. But I think it’s a big takeaway for entrepreneurs that are looking at the regulated space to say, “Is there somebody doing this that’s leveraging the current technology to make it more logical?” And right now, that would be agentic frameworks.

William Caldwell: In regulated spaces, it’s tough. I would say we’re probably five years out, just because, again, it comes back to that point, like the compliance person or the head of mortgage or whatever at that bank is not going to just let some LLM inside the curtain and lose their job. And so, we’re seeing a very conservative approach from the regulated markets to this. They’ll have internal clouds. But again, I think the frame you have like a couple-year window to like learn the space from an agentic’s point of view, where we’re seeing efficiency gains is more on product development, like within the space, not putting like PII through these LLMs, but more so helping us get product to market way faster in terms of like if you’re going to enter these spaces today.

Brad Weimert: And because I like to spell out every acronym, PII is?

William Caldwell: Personally identifiable information.

Brad Weimert: Right. It’s all the private stuff that you’re not supposed to expose to other people.

William Caldwell: Correct.

Brad Weimert: Yeah. Look, I think that that’s awesome, and my experience is the same as you probably know. I have a little bit of experience in the banking space, and I couldn’t agree with you more. Also, one of the areas that we’re seeing AI and agentic be incredibly, incredibly powerful for our products, and we’re just barely seeing other people do it in the space, but it’s underwriting. And so, when you look at the capacity to go out and find information about people today, it used to be contingent on having the right API and pulling the right data quickly, as quickly as you could, and then ultimately having a human review it. And now you can have an agentic flow that goes out and pulls everything that you want all at the same time and then have another agent scrub it and score it.

And, yes, you still have somebody at the end of the chain that’s a human that has to sign off on that and take risk on it, but it is the beginning of this era where it has to be adopted by people. It’s just the economics alone, if you get it to work right, the economics alone are so radically different than having a human sit and scrub through something for six hours, right? Or in the case of a mortgage, two f*cking weeks. I don’t know. I don’t know what they’re doing for two weeks, but.

William Caldwell: That’s interesting, you say that. Obviously, I have a front row seat to AI underwriting and seeing how it’s being used. One, I think there’s going to be a lot of job loss in the space, and people are terrified of the AI underwriters because it means their jobs, one. But I do see that component of underwriting becoming super commoditized too, where it just is like, kind of like a cloud level layer. They’re all relatively like what the LLMs today between Chat, Gemini, and then Claude, like, they all have their different flavors, but you’re going to see underwriting and financial services become kind of just like a commoditized product at some point in the future, is where I think it’s heading.

Brad Weimert: That’s interesting. So, my take for a long time before, well before we found ourselves in this era of AI, has been that there are better ways to build associations that are correlated to somebody’s likelihood to default and set another way for people that don’t know what the f*ck we’re talking about. You can predict somebody’s behavior by things that they do in their day-to-day life that most people wouldn’t think through, right, wouldn’t realize. And so, like my hypothesis has been the connections that you have in your social network, who you’re friends with on Facebook, whose posts you comment on, what stories you read, what you click on, et cetera, et cetera, stuff that is in the public footprint out there probably has a correlation to your likelihood to not pay your mortgage payment in some capacity.

And the question is, what data points are we not looking at right now that can drive that outcome? And that’s like in my immediate underwriting world, I’m thinking about that stuff. But that principle applies to tons of other things. And I think for most entrepreneurs, it applies to the buying cycle. What are the buying signals for somebody that you wouldn’t otherwise expect, and how can you potentially target them? So, how can you target a potential customer in a different way? And I think that there are some parallel there.

William Caldwell: Yeah. I mean, it’s interesting because, I mean, the mortgage industry is notorious for getting in a lot of lawsuits around aggressive tactics. It’s going after consumers. I’m not that familiar with like the lead gen space, kind of find the buying signals on that side of the house. Although I do think a lot of those buying signal, like there’s going to be more regulation around this. This is going to be invasion of privacy. There’s going to be something coming down. It’s just going to get too creepy. It already is kind of creepy. And kind of that’s where we’re at right now.

Brad Weimert: Yeah. Well, I agree with you. It’s certainly going to happen. The question is when. And I think that for most entrepreneurs, the idea of how do I find more clients and what’s a more creative way to do it, rest assured, all the major ad platforms are already doing all the creepy sh*t and will continue to do it to try to serve you a more and more relevant audience. And we, as consumers, will feel that as we get targeted more and more specifically for things that we talk about in our private rooms. So, let’s talk about distribution for you for a minute, because originally, you’re selling an app, and ultimately, you sold through an API.

William Caldwell: Yeah.

Brad Weimert: And fundamentally, when I think about, like, I think this is an opportunity for entrepreneurs to think about their distribution model for their business or their customer acquisition model, right? How are they getting their product out there, and how are they finding clients? And functionally, you found one giant strategic partner to sell your products through, right? How do you hire for that? So, when you shift your business model from, “Hey, we’re targeting independent agents,” to, “We’ve got a strategic partner, and we’re building out the API for it,” what does the makeup of the team change to when you’re doing that? And how do you think about the roles that you need?

William Caldwell: You honestly don’t need any more salespeople. So, you get rid of that. And then you just are solely focused on product and engineering and customer support. In our case, because we got paired up with like the gorilla, the biggest player, like the minute they started selling it, it was just they sold more clients in the first month than we sold in two and a half years. So, we hitched our wagon to that horse, and that was it for us.

Brad Weimert: Were you prepared for that increase in volume? Did it matter?

William Caldwell: It didn’t matter. We can run every loan in the United States if we wanted to today with no…

Brad Weimert: So, fully automated.

William Caldwell: With like no more people. Probably, it was just these sales. These tech companies, they just get so sales heavy because the customer acquisition cost in these regulated industries is astronomical.  You go broke before, like the product’s great, but it’s just so expensive to acquire customers.

Brad Weimert: And so, the solution to that was the giant strategic partner integration.

William Caldwell: In any type of regulated space, you almost– I wouldn’t even attempt this space without some type of strategic partnership from the onset.

Brad Weimert: Love it. Do you think that people need to build the product ahead of time? Do you think you can go forge the partnership and build the product for the partner?

William Caldwell: No, because I think, we built this. When I got into the flood space, like I already had the hazard business running in California. We were cash flowing. It was doing fine. But I called a few lenders and I was like, hey, if I’m going to build a flood cert, what are you paying today? They’re like 12 bucks. If I do it for six, will you buy? And before we even built anything, I confirmed we had customers and they were our first customer. And so, that was kind of how we broke in.

Brad Weimert: Crazy. So, you just undercut the market.

William Caldwell: Yes.

Brad Weimert: That sounds so simple.

William Caldwell: We were just, it was the right product, right time, crazy margins. And I looked at it as the wedge. It was like once we had the customer lot and we’re doing it now, it’s a lot easier to sell more stuff.

Brad Weimert: All right, so if Congress repealed disclosure requirements tomorrow, how would you adjust your plan? Or would you just call it quits?

William Caldwell: I’m glad I sold.

Brad Weimert: Well, let’s talk about that. So, walk us through the first contact from ICE and let’s clarify what ICE is. Let the internet go crazy about us talking about the benefits of ICE.

William Caldwell: Yeah, it’s not the immigration ICE. It’s called Intercontinental Exchange. They’re about a $95 billion market cap company. They own the New York Stock Exchange. Have you ever heard of Ice Brent Crude, that is their oil futures contract. I think they traded about 400 million contracts last month. So, they’re doing just fine. They love volatility, big volatility guys. and then they also own mortgage technology, which is about 2.2 billion in revenue a year.

Brad Weimert: Got it. So, little fella. Did they reach out to you? How did that come to be? And did you deliberately build the company to sell? Or was this interaction a surprise?

William Caldwell: I built this company to sell. What I liked about it was, it was an easy company to sell because it was a modern platform that big companies weren’t going to redo themselves. And they already had market share, so it was like you could sell it two ways. You want to get into the flood space. You want to sell it as like a market airplay. It was just a very viable asset. And I knew that from day one. So, that’s kind of my thought process going into it, how we got here, like the origin of it. And I had investors I wanted to, like, start a company, sell it, get return, like make them a lot of money, and then go do the next thing, kind of. That was my mantra.

Brad Weimert: And how did you connect with ICE?

William Caldwell: It was a good story. I had almost sold the company in 2022, I believe. But then when mortgage rates go up 400%, people don’t buy real estate technology. And that was a hard lesson because it was just like, I was a week away from closing. I was getting married and it fell apart at the last minute. And so, that was just…

Brad Weimert: With ICE?

William Caldwell: No, with another company in the space, a title company, that they had, again, very head-to-head competitor. But then what happened was like about a month later, I go to a conference and just try to like lick my wounds. It was going to be life changing money, but I had to like kind of get back in and start driving again. And I get in the taxi with a guy from what was Black Knight, but now ICE. And I pitched him on what we’re doing and I’m going to build in the next gen flood product. And I didn’t think much of it. I think he thought I was nuts because he is like, there’s already very well-established flood companies. You are, what are you doing? Why are you different? Anyways, we had a relationship and then about six months later, go by. He calls me and he’s like, hey, I want you to meet the president of the data business here at ICE? We want to learn more. I didn’t think much of it.

And it was, I pitch him on what we’re doing. We’re starting to get some traction now in the flood space. We landed a few big clients. Like things are starting to go in the right direction. So, we had momentum, the integration, like the legacy infrastructure was working great, like we were definitely on the right path up into the right– in a rate environment too, where housing volumes were at historic lows. Like, it’s been really rough.

So, about a month after that interaction, they call me back. They’re like, “Hey, we want to make you the exclusive flood provider for ICE.” And I’m like, “Holy sh*t.” So, I’m like, if this works, this is my ticket. Like, this will be my off– like this will work. I don’t think we or them understood how successful it would actually be though, because resale partnerships generally don’t work. They’re tough to execute on, to get everyone aligned, incentives. Like just motivation from the sales team, I’ve done them before and none of them ever worked.

But we put about a year of effort into prepping for that. I said yes, let’s do it. We then launched in, I think it was 2024 in March 1st. And then within the first month, I think we closed 45 banks. And so, to sell a bank, generally, your sales cycle’s like a year, and we did 45 of them in the first month. And so, I was just like, this is, I’m in. And then we did it again the next month.

Brad Weimert: And that was based on the credibility of being tied to ICE?

William Caldwell: Yeah, because it was an easy, like, again, I think, like we both didn’t understand how much the market did not like the incumbent providers because they were not innovating. They were price gouging, and it was just like something new and fresh that worked really well. And it was just like a great sale for the sales team. And when you have salespeople put up a lot of points, they’ll go to war, they’ll die for you.

Brad Weimert: Yeah, I mean now I’ve got, now you spark curiosity around the sales of this. So, we started by saying, “Hey, when you’re growing something that’s driven by API, you can get rid of your sales.” So, how did that bridge work? And when you talk about having salespeople and getting banks on board, what are the dynamics there, both who you had, why you were soliciting the banks, and what the commission structure was?

William Caldwell: So, the play was ICE has a few hundred salespeople that service their market share, which is significant. And so, they’re just always– they do a great job, like, of they have a very well-run organization, like the best I’ve ever, like, I don’t have much experience, but it’s incredible the way they are able to execute at scale.

Certainly, I would say like a difference between a billion-dollar company and a hundred-billion-dollar company, like it’s very apparent, like the structure, how this place works, and I’ve really enjoyed that. And so, once they got us in like where we were able to be, one, plug into Salesforce, added as a SKU and just into their whole like flywheel. It was just an easy sale for the sales team at ICE to then just add it on and on the renewals just as an add-on, like it was just– and because you already contracted with these banks and you’re through compliance, that is a major competitive advantage for people selling regulated spaces because vendor management kills deals, like it’s just time. It takes forever. But if you don’t have to deal with that, people still, like, it’s just a lot easier.

Brad Weimert: Interesting. So, God, that’s a huge moat, right? So, ICE, basically what I heard, I think was first and foremost, not your salespeople. So, when you said, “Hey, I don’t need sales,” you’re a tech company and you’re providing an API that gets this flood cert and a few other products ultimately. You tie to ICE who has a mortgage product that banks can use, that’s already passed all compliance regulation considerations for the bank. So, everybody says, “Hey, this is a product we don’t have to vet any further. And in some cases, we’re already using. All you need to do is turn on the API for this new flood cert product that is half the price of the previous one.”

William Caldwell: Yes.

Brad Weimert: Sick. And so, if anybody wanted to come in and disrupt that, they’d either have to fight the relationship and get the relationship with ICE or your other legacy platform and/or replace the ICE mortgage platform or the legacy platform in that tie into the bank.

William Caldwell: Correct.

Brad Weimert: Crazy. Yeah, that seems like a bitch to get into. So, this all happens. What’s the timeline from starting the company to ICE reaching out? And what’s the timeline from ICE reaching out to sale?

William Caldwell: So, within 60 days of us launching, I got the call and I was like, oh, well, you got to remember, I was like, PTSD from a sale following through. So, I was just hyper-skeptical by the way. My frame of mind was like, I like this. I’m really excited about our vision. We want to continue to execute. but it’s ICE, they got a big balance sheet, like, you got to be smart here. And I like the people and I was having a baby too, so just like I was going through some life things. And I needed some more stability in our lives. Like we were living in Wyoming. My wife wasn’t too fired up on living in Wyoming. And the opportunity presented itself to kind of potentially go to Atlanta where ICE is headquartered, work there, and kind of learn more, but from the day we sold that call, we closed October 25th of that year, but we had our baby October 21st, so it was just like one wild hell of a week.

Brad Weimert: Jesus. So, I know you’ve got some NDAs in terms of terms, but I do know that you sold 51%. Why was that the number at this point? So, when I hear sale to massive company, first and foremost, the one option or I think the big desire for lots of entrepreneurs is like, I’m f*cking out. Let me sell the company and be done. And then the other is sort of like the second bite of the apple play and try to grow something even bigger. And usually, that’s a private equity consideration. Why was it 51%? Why did you not want to sell the whole thing or sell less? What did that look like?

William Caldwell: I love what I do. Retirement’s like, not even in the cards. So, even at 51%, it was still like life-changing money. We got over 10 times revenue for the company. We bootstrapped it, only raised a million dollars, so it was just like a huge win for everyone. But I believe in what we’re doing. Like, I will die on this hill. Like, I see the opportunity. They do about 4 million loans a year originated on the ICE platform. To me, I look at that.

Anything times 4 million is a good number, and there’s a lot of products that we can continue to build that just need to be reinvented with AI and just like what you can do with that, that opportunity is massive. It’s in the billions of dollars in incremental revenue to ICE.

Brad Weimert: So, you wanted to keep doing it is the answer on the 51%?

William Caldwell: Yeah, that was it.

Brad Weimert: That for me, I immediately think the downside to that is now I have to work for this massive company, and now I’m an employee of the company. You sell, you get life-changing money, you have a baby? What is going to work like the next Monday? And what are the next six months look like for you?

William Caldwell: The most common question I get asked here is what’s next? So, we’re launching a new product and I’m really excited about that, but they’re already like, what’s next after that? And so, it’s just like the culture here is just, it fits my personality and it’s like a good fit for what I like to do and I just want to keep going. It’s founded by an entrepreneur that he’s still running, Jeffrey Sprecher. And so, that permeates from the top down.

Brad Weimert: So, you like it?

William Caldwell: I like it.

Brad Weimert: I would say count yourself lucky on that front, man. Well, let me actually ask you, did you know? Did you have a thought that it would be that way when you sold to them? I mean, most entrepreneurs that I know when they sell and they get stuck in earnout in some capacity, more often than not, they’re miserable. Did you think about that leading up to the sale and transition?

William Caldwell: No.

Brad Weimert: Did you just get lucky?

William Caldwell: Maybe lucky, but I think what I’ve learned being in a huge company is like sales cures all. And so, if you’re selling, you kind of people just want you to keep selling and get out of your way.

Brad Weimert: What is something that an entrepreneur should be aware of if they’re selling into a massive company?

William Caldwell: Deal economics is important for your earnout, making sure that is, one, you’re going to get paid again, I think. I know with some private equity deals and in our last time, we were going to sell, like there was no shot at getting paid again. So, making sure you structure a deal in which you can get paid again, and you’re happy with that. And then, culturally, the people, like, is it someone, are these people that you’re going to see every day, like, is that going to be a fit?

Brad Weimert: What is the weirdest question that they asked you when they were doing due diligence? What’s the weirdest question that ICE asked you when they were doing due diligence about your company?

William Caldwell: Well, one, that thing that came up was just like, we had some like old code that ended up on the dark web during diligence and I was like, oh, man, this is going to kill the deal. And so, that was like, one, heart wrenching because I was like, “No,” but it was just like, it was a nothing burger at the end. But that was a one out of the left field.

Brad Weimert: What was the code?

William Caldwell: Like our old code, like a code base that like, didn’t even run. I don’t know how it got up there. It was like our code base from like years ago. So, it was just strange.

Brad Weimert: That is weird. What was it being used for? Why did anybody care about it on the dark web?

William Caldwell: I don’t think anyone did. Someone was just trying to make like a hundred dollars or whatever. And so, when ICE bought it and it was just like kind of out there.

Brad Weimert: Okay, so you go through the transaction. I’ve asked you this a couple different ways, but actually, I want to get to kind of post exit and day-to-day life now. But before we go into that chapter, I’ve asked you this a couple different ways, but if you lost Snap today and you wanted to launch a property technology company, what would you do differently? How would you approach that today?

William Caldwell: Before I built, wrote a single line of code, I would lock in a distribution channel like, or else I wouldn’t even do it.

Brad Weimert: And what would that look like for you? When you say lock in a distribution channel, I have a good image of that from talking to you here, but what would that look like and what path would an entrepreneur take if they were going down that road?

William Caldwell: Like, a very strategic approach, I would do it, again, is like approach strategic customers that have scale, get them to invest early on, basically, guarantee that like first bite of revenue that you get the cash flow going. And you can do that in any industry, but anyone that has scale, a reputation that can help you, get out of the gates. It just saves a lot of headache from day one.

Brad Weimert: Yeah, I think that the, particularly today, as software is getting easier to execute for non-technical people. The initiative that most entrepreneurs are going to go down is to build product. And I think that it feels productive and sometimes it’s scary to go sell when you don’t have a product. But your advice is to spend the time laying the foundation, talking to the people, kicking the tires, seeing if you can get a distribution channel or a strategic partner that will actually buy the product before you bother building it.

William Caldwell: Yes, that’s what you have to do in this day and age.

Brad Weimert: Okay, what is life like after you’ve made life-changing money? How has your risk-reward, your decision making, et cetera changed?

William Caldwell: With a baby, I mean, to be honest, life’s gotten a lot more comfortable. The financial security is there. You can take more risks. I’ve started investing quite a bit. It’s been a lot of fun. I’ve enjoyed it. But it just allowed me to just like even more double down on what I’m doing here at Snap without worrying about payroll or just like things that you deal with when you’re bootstrapping a company and it’s just like, you’re just in scrappy mode. We’re able to invest more in product and that’s been just a lot more fun. Like, I’ve really enjoyed that piece.

Brad Weimert: Yeah. I personally very much have had that experience where, once I got to the point of not worrying about money at all and I had to get way past that line, but once I did, my desire to take bigger swings increased.

William Caldwell: 100%.

Brad Weimert: What are you investing in?

William Caldwell: I mean, we did that oil and gas deal together.

Brad Weimert: Ah, yeah, that’s true.

William Caldwell: It’s actually looking to be– that might be a pretty good one with the oil prices today.

Brad Weimert: Yeah. Well, for the moment.

William Caldwell: Yeah, for the moment. I invested in a bank recently. They’re starting a bank only because the guy I know who’s going like put his life savings in and I was like, I have to be a part of this because I like you and I think you’re going to be successful. So, I was like bet on the person. Private equity, stocks, bonds, buying land and flipping it, that’s been fun. So, like, land that costs like a hundred grand and selling it for like 150. So, that’s been a little fun side gig. So, just a little bit of everything.

Brad Weimert: Do you feel like you have a strategic, this is like, what people do with their money once they exit is endlessly interesting to me, and I think there are a million different approaches. Do you feel like you have a strategic approach for investment or do you feel like you’re sort of just exploring and playing?

William Caldwell: Right now, I’m just exploring and playing, so it’s, I mean, I’ve done well with real estate, so I don’t have to worry too much about where I’m living. So, it’s just like fun for me now. So, that’s been– I don’t know, it’s been interesting. Once you have a house, I don’t know, I feel comfortable. My wife’s happy. She didn’t have to work anymore. So, it’s been nice for our family.

Brad Weimert: Awesome. What advice do you have for a 25-year-old entrepreneur starting out today?

William Caldwell: I can’t emphasize enough. Spend more and more time with customers, making sure they’ll actually pay you. Like, I think that is, like, they’ll say they’ll sign up, but making sure they’ll actually pay. And if you can even get to do a vest, like that’s even better because then, they’re financially committed. But nail down that customer profile and make sure there’s more than a few customers that’ll actually buy what you’re building.

Brad Weimert: What books, podcasts, or other things have shaped your thinking most in the last year?

William Caldwell: I mean, the one that was really influential that got us to where I was here today was Thiel’s Zero to One. The idea of doing the dirty work, like, why that was instrumental to me, it was like actually aggregating the data, owning the infrastructure, and like all the way through distribution was just like a very profound piece of advice. And that’s why I think we were successful ultimately.

Brad Weimert: Love it. Well, Caldwell, where can people find you if they want to find out more about you?

William Caldwell: I am on LinkedIn. That’s where I spend most of my time. So, we’ll put that in the description.

Brad Weimert: Yeah, we’ll put it in the show notes, man. I love it, dude. Always good getting time in. Looking forward to our next snowboard session. And hopefully, we’ll make some money with oil.

William Caldwell: Yeah. Thanks, Brad. Thanks for having me.

Brad Weimert: Thanks, Will. See you.