211: How a “Boring” Business Sold for 2x Market Value with Will Duke

Physical security is a brutally competitive, commoditized industry. Most companies look the same, act the same, and sell for the same.

Will Duke did things differently. And when it came time to sell, buyers lined up.

He didn’t just exit the core business. Along the way, Will built an internal software platform to manage and track thousands of security devices for customers. That platform eventually became its own SaaS company, and both businesses were sold as part of the same exit, at roughly double market value.

In this episode, we break down how he differentiated in a crowded market, what actually mattered during the sale, and his repeatable process for investing smartly after an exit.

If you want to understand what actually drives valuation, and why buyers were willing to pay a premium for Will’s business, this episode is definitely worth your time.

Mic Drop Moments

• “If you sit down and ask clients, ‘Where are you now, and where are you trying to go?’ and you help them get there, I mean, that’s worked in the past, it works today, it’ll work until the end of time. Those are timeless principles.” – Will Duke

• 00:45 Building a Business Over 20 Years
• 03:00 Selling Outcomes, Not Security Hardware
• 08:19 Using Data to Differentiate
• 14:00 The SaaS Tool that Became a Competitive Advantage
• 21:45 Video Surveillance for Small Business Owners
• 26:20 Advice for Entrepreneurs Exiting a Business
• 31:02 Exiting Two Companies at the Same Time
• 33:46 How to Use AI Before Talking to Attorneys
• 35:39 Maximizing Exit Value Through Culture & Core Values
• 43:07 Learning How to Invest Post-Exit
• 46:12 A Repeatable System for Vetting Investments

Brad Weimert: Will Duke, welcome to the show.

Will Duke: Thanks, man. Glad to be here.

Brad Weimert: So, you had a business that you built for 20 years. What experience do you think you get from building a business that long that serial entrepreneurs don’t, who are kind of jumping from thing to thing, selling and moving on?

Will Duke: I think about a company in stages of like, so I have a 7-year-old daughter, right? And so, how she was at one versus two, now seven, it’s a different chapter. In the beginning, you go from how do we stay in business. You’re doing everything. And then, as you grow the company, you have to develop teams and people. And then there’s just different problems, bigger problems. But from a serial entrepreneur, if you’re in and out of companies, you never get a full chance to develop people. So, we had probably five or six people that were with us for 15 or 16 years. We’re talking about relationships before we turn the mic on, and those are important relationships to me, but I don’t know if that answers your question or not.

Brad Weimert: Yeah, I think so. I mean, I think the relationship-building part of it is a big part of it but the other thing that I think of is, if you’re moving through things in two to four years, or two to five years, and then selling and moving on, and I guess it probably depends on scale, but it’s very likely that you’ve figured out how to navigate around a problem instead of direct, right? So, it’s possible that you ran the sale and you just didn’t learn the full lesson from these obstacles. And I think when you’re in it for a really long time, maybe you have more depth in the understanding. I don’t know. I’ve been in something for 15 years, also. So, I don’t really know the other side of the coin.

Will Duke: Well, I definitely say for like the first 10 years, we pretty much just bought ourselves a job. Like, we were learning how to do business. At that point, we hadn’t really gotten in any groups before Vistage or Strategic Coach. We didn’t know how to put a rhythm or a vision, or a roadmap. We were just selling stuff and installing stuff. And they were like, “Well, if we’re going to do this, let’s make money.” And so, the second 10 years, it was like, how do we build a company that I actually can build wealth for myself and my business partner, and then also, how can our people succeed along the way?

Brad Weimert: So, you kind of just answered this then, but I want some nuance to it. Yesterday you told me, “It’s been three years since the exit, and now I’m itching to do something again.”

Will Duke: I am. Yeah.

Brad Weimert: How did you keep yourself engaged for 20 years in the same company? And you said, basically, the beginning, you were just sort of learning, stumbling through it, and in the next 10 years, you were trying to build something and make money. What was engaging to you through that process, and what helped kind of get from one level to the next?

Will Duke: You know, good question. So, I think it’s learning and evolving. Creativity is a big part of entrepreneurship. How do we approach the market differently? We were, in our world, considered a VAR, value-added reseller, like we sold electronic security. So, we sold and installed stuff that our competitors also sold and installed at basically the same price. So, the only thing we could change is the experience, and I would attribute probably the last six years of our existence, I was in Strategic Coach, let’s see, five and a half years. That group really helped me elevate my thinking and how to deliver our product in a different way that got not only our team involved, but the customers involved. It really changed my perspective massively. And really all really good ways.

Brad Weimert: Tell me about that process. What did you do to get the customers involved, and what does that mean?

Will Duke: So, we really took an approach, even more so, like the last four years of creating like collaboration workshops. We build out five-year road maps. We’d have people come into our office. It could be C-suite to individual contributor. We put them all in the same room together, and we had asked them, “What are you guys trying to achieve? Where are you trying to go?” And we’d help them kind of paint a five-year roadmap. And our competitors never did that. They were just trying to sell stuff. We were actually trying to help them.

Brad Weimert: So, to that end, when I hear that, and I think that there are some parallels with selling payment processing functionally. But when I hear that, I think, what customer wants to come in and talk to you about their roadmap for digital security? I mean, was that the starting point? Is that why you hadn’t done it before? Like, how do you reconcile that?

Will Duke: So, I think it’s just like anything, right? You’re just like, “I think this is a good idea. Let’s try it.” And I would always tell our team, “We don’t get to skip down the hallways unless our clients are skipping down the hallways first.” And so, we did it. Our very first client, our largest client, H-E-B grocery store here in Texas, they came in. We worked with them. They loved it, which was a little bit of a risk, because I’m like, “Man, if they hate it…” I mean, maybe it wasn’t that big of a risk, but if they hate it, it’s just kind of like, “Oh, okay, it was a decent idea,” but they loved it. And I think they loved it, because nobody ever asked them those questions before, and we had large commercial clients, and pretty much all of them loved it.

Brad Weimert: So, let me get some details on that, because I think one of the challenges for certainly new entrepreneurs, but even established entrepreneurs, is sort of taking a concept that somebody else has applied in their business, and trying to map it onto your own. And when you look at the large strategic concepts, that becomes very difficult, murky area in actual execution, where you think, “Okay, that’s a great idea, but how would I apply that to me?” So, I think a little background on what the company was selling, specifically digital security, what that means, and then what that process looked like would be helpful for people to map on.

Will Duke: So, we sold and installed. If you go into any large institution that has thousands of people going through it so school districts, universities, grocery stores, but it was video surveillance, access control, the hardware, the software, the cable, all the components, connecting it all together, plugging into the switch, and then bringing it online. And the process was basically, you know, I took elements of my time at Vistage, my time at Strategic Coach. We also used EOS by Gino Wickman. I took elements of all three of those programs and said, “How could we package this in a manner that our clients could possibly resonate with?” And it really came down to as long as we make it all about our clients and helping them achieve their goals, the premise was they might buy more from us.

And so, I think the product is almost irrelevant in this case. It’s how do you make it all about your client, and then how do you involve your team along the way? Because I didn’t want to be the one pushing this thing. It was my idea, but it had to be a team approach. Otherwise, I would die. It would need so much energy. So, the approach is really, where are people now, where do they want to go, and what’s keeping them from achieving those goals? Like, just basic goal setting 101. And if you sit down and ask clients, “Where are you now, and where are you trying to go?” and you help them get there, I mean, that’s worked in the past, it works today, it’ll work until the end of time, in my opinion. I think those are timeless principles.

Brad Weimert: So, I’m thinking, and I want to double-click a little further, because at a glance, and I think this is true of almost all businesses, you look at just the top level, what’s the product or service being delivered, right? And so, to me, let’s say I own a hotel, and I’ve got 40 cameras, or I’ve got a few hotels, and I’ve got 400 cameras, and I’m thinking, what do I want? I want to be able to see things all across the property, and I want to be able to have access control so that certain people can get into certain doors. That’s it, and I don’t want it to be a pain in the ass. So, how do you take that fundamental deliverable and expand that into sort of the client vision, and the client being engaged and creating more of an emotional connection to the problem and the outcome?

Will Duke: It’s a good question. So, historically, physical security has been a reactive thing. Something bad happens. You go to the tapes, pull it up, bring in the authorities. And so, I’m sure we’ll touch on AI, but we started using AI probably back in 2016-2017. The top-tier manufacturers would put it in their product. And so, what it allowed us to do is how we look for predictive behaviors on the front end before they happen, so more of a proactive manner. And we were able to also use the products towards process improvement. If you can see a field of view of how people are behaving, and you can see how they act, you can start to predict their behavior. And so, we would go down those paths in different areas, process improvement.

In one specific case, one of our customers was throwing away millions of dollars of the corrugated boxes instead of putting them in the recycle bin, and it was like a $10 million savings just by capturing that on video and altering the behavior of all their locations. And so, you start to pick up on stuff like that. And then you have to be careful too, because you can get too far outside your wheelhouse while you’re trying to, like, solve things that you’re not qualified for. So, there’s that shiny object syndrome where you have to be careful. But it was interesting. It’s like how could we think about security process improvement in a different way? And it always involved the customer.

And then it was a co-creation collaboration where you come together and say, like, we would do 90-day, six-month sprints. That’s probably not the right word for it, but projects where we would test, we would always have stuff in our lab. We would test it at our office. And so, that would be one of the things that we come in during one of the quarterly sessions that we would, “Here’s our findings,” and they would jump up and down, or they would go, “Nah, that’s okay.” But if they jumped up and down, I mean, it was a multi-million dollar opportunity for us.

Brad Weimert: I think one of the takeaways for people, in general, is how can you look at the behavior and the data that comes from your core product or service, and extrapolate that into other valuable things for the client? And that’s going to be obviously different across the board, but I love the idea of sort of watching the tape and seeing where process improvement could happen, right? What patterns exist elsewhere? And in our world, in the payments world, we’re looking at transaction data and user behavior on the website, refunds, disputes, recurring billing patterns, et cetera, et cetera. All of that gives us a tremendous amount of information per client and for the user base as well. But a completely different use case than yours, but the fundamentals, I think, are look at the data.

Okay. So, one of the things that I think is interesting, at least from the outside, looking at your experience in that company, we’ve got two things, but one is you switched roles a few times, and I don’t know if that was like sort of semantics inside the company because you were working with your partner to grow it, but you started as a VP, and then moved to President, then moved to CEO. Were those changes really deliberate? At what stages did they happen? Were they correlated to revenue? Were they jumps in direction? Tell me about the progress through the company’s evolution that way.

Will Duke: So, early on, I was the front of the house leader. I like to be in front of customers, driving the revenue. And so, that was probably the first half of our company. And then as we started to progress and we built out our software company, with our I like to call it an entrepreneurial seizure, which we put millions of dollars into that product. My partner, Joseph, started to run the software company, and then I started to run our integration company. And it was just a natural progression to go from President to CEO. Didn’t really read too much into titles. I would always tell our people, I only care about my title in two scenarios: if we’re trying to win business, it helps us, because if the CEO shows up to a meeting, it means something. And then if a customer is really pissed off, I’ll hop on the phone and own it. So, that’s the only two times I really cared about my title: to win business or to calm down an upset customer.

Brad Weimert: Yeah, that makes sense. So, you mentioned the software company, SiteOwl, and so I think the natural progression of most businesses is you continue to try to look for how to make the processes more streamlined. And in today’s world, you’re kind of looking at what off-the-shelf stuff exists. And right now, you can start to play with AI to build your own stuff, but realistically, the complexity of what is involved for enterprise-level solutions, good luck trying to vibe code that sh*t. You can probably vibe code some little apps right now, but you’re still looking at big software development undertaking. And by the way, I think that’s all in the future.

But back out a few years, you hit a point where you decided you wanted to spin up an entire software company, own P&L, own process, to the extent that you said you split with your partner and he ran one, you ran this one. I mean, you were still together, but tell me about the journey with SiteOwl, and more specifically, how did you decide that this was a worthwhile distraction versus a shiny object.

Will Duke: So, really, the fundamental premise of what we’re trying to solve was, how do we keep track of all of our sh*t? We had customers with thousands, sometimes hundreds of thousands of devices, and there was literally, Brad, there was nothing on the market. The Monday.com, the Asana, they’re all project management software, right? And we needed something specific to if a tech rolls into a building and the camera’s down, where? Sometimes you walk into a site location could have a thousand cameras. Where’s the visual representation of where it’s down? You can label it, yeah.

Brad Weimert: So, just for your techs. Forget about the client themselves in terms of tracking it. For your techs, when you wanted to support it, you didn’t have an easy way to diagnose and see.

Will Duke: We did, and then none of our manufacturers built it. They had semblances of different types of things. You could import a PDF floor plan, but it just wasn’t enough. And so, we went down the path. We kept track of all of our stuff in Excel back in the day.

Brad Weimert: Good God.

Will Duke: Yeah. And so, it got to be too much. And so, we went down the path. We built it out. The first three or four versions of it were just absolute sh*t. And then I give Joseph a ton of credit, because he went all in. We built the product with developers all over the world. It probably won fourth the costs of what it would have cost us had we used all US developers. We had developers in Russia, Germany. We had everywhere, but really all the credit to him. And instead of taking ownership distributions, we just funnel the money on over to the software. And just like other entrepreneurs, you have no idea if it’s going to be successful or not, but it became big enough until we said, “Hey, this is something that we think could be a viable product that others might want.” And it turned out to be true, very true.

Brad Weimert: Did you build it with that in mind from the beginning, or sort of stumble upon that eventually?

Will Duke: It was built out initially as our potential competitive advantage, and it just felt bigger than that. It just felt bigger than another division of our company, a completely different segment, although related. Software as a Service is completely different than an integration company, as you know, but it did not start out that way. It started off as, like, how do we keep track of our sh*t?

Brad Weimert: So, I think that that path is, I mean, I think I hear a lot of founder stories that are scratching their own itch, and it evolved into a product. We have a full-time development team in-house, and everything that we build, I think about how do we make sure that this is something that could be a white labeled product, meaning I could sell it to other people for them to use it for their own purposes. But if you don’t do that from the beginning, retooling it to do that can be kind of a b*tch. Did you hit a point where you were like, “Oh sh*t, we want to take this to market, to sell it to other people,” then you’re like, “We have to redo a bunch of stuff in order to do that,” or was it sort of tool effective from the beginning?

Will Duke: So, I’d say it’s fairly tooled effectively. The number one thing was making sure that the software didn’t go down. So, if you get a customer’s devices up and live like it has to work. It can’t maybe sometimes work. But that initially, I know, early on, we switched over to I think it was Amazon as our back-end AWS. But early on, we dropped a couple of times. And I mean, really, God bless our people, because our technicians were the guinea pigs, right? They would go out, sometimes the software would drop offline, you know? They would go out and map out a customer site, and then all the devices would drop off, and they would come back to the office and want to wring our necks. But all credit goes to our people.

Brad Weimert: Okay. So, looking back on this now, SiteOwl, what was the biggest value proposition of it? Was it that it increased the margins in your own business, the valuation of your own business, or was it the value of it as a standalone company, and what you made off of it?

Will Duke: So, I definitely think it helped 3Sixty separate from the competitors, because we could show, I mean, the fundamental premise was, how do we reduce friction? How do we give customers the data they need immediately? If something drops offline, how can they tell us immediately, and we get it back up? So, the fundamental premise is, how do we reduce the friction? So, from a value standpoint, when we presented our value proposition, we could say, “This is how we track our projects on the front end, this is how we monitor projects during the process, and this is how we’ll monitor stuff after the project.” And by the way, we will have very specific device history of anything that’s ever been installed by us. Regardless if a technician is with us, we will have the data.

And so, every time that device is touched, we’ll know it, and so will you. And really, the big thing too in our industry, one of the bad habits of our industry was the integrator like to keep all the data close. So, basically, the customer is a prisoner, and that always used to piss me off. It’s the customer’s data. They paid for it, and more times than not, even the larger customers never knew when it was installed, how old it was, because these are all technology products that need to be refreshed every three to five years. But then moving over from a value proposition, the true value was SiteOwl being stood up as a separate company, going down its own path, and then 3Sixty with a very close parallel path, if that answers your question.

Brad Weimert: It does. So, a lot of value in both there. Well, I want to talk about kind of the process of selling, also. But before I do, I have to scratch my own itch, because you’re talking about it from the sort of security industry perspective, right? You use the term integrator, which is, in this case, the company that comes out and integrates all the security sh*t into a business. From my perspective, from small business guy’s perspective, I just like dope security systems because they’re fun, and I can spy on people, and set up a different way. I can monitor the activity in the building. And, for me, I’m a real estate guy, so I’ve got a whole bunch of properties and a whole bunch of cameras all over the place, but I have a very light version of what you’re talking about.

Give people an idea for the small business owners out there, and maybe you have opinions on this, maybe you don’t, the systems that make sense to use when you need 5 to 50 cameras, versus your enterprise clients, which you might need 1,000 cameras.

Will Duke: I mean, one of the great things about technology is how affordable the stuff is now. I mean, I’ve got stuff on my home that 10 years ago would have been $150,000. So, from a small business owner’s perspective, most of everything’s up in the cloud now. You can literally plug a camera into a switch and then see it on your phone. Very high resolution, super clear, color by day, black and white by night, it can flip over to IR mode, and a lot of cameras out there are colored by night too, but black and white is actually better at night. But from a perspective of cost, I mean, you can have something for $5,000 to $10,000 pretty quick. That’s just like really high-quality stuff.

Brad Weimert: What are a couple of brands that you trust today in the end of 2025 from that perspective?

Will Duke: There’s a brand called Dahua. Even like the big boys in our industry, there’s a camera brand called Axis, and they make all different tiers of products, but those are the top two off my head. All the other stuff that we would sell was super high-end, enterprise-level stuff that every day small business owner probably wouldn’t relate to. It wouldn’t make sense economically.

Brad Weimert: Sure. Yeah. So, we’ll dig into AI in a bit here. And privacy inevitably comes up when you talk about AI. From a security perspective, when you’re putting cameras all over the place, I have general concerns with using sort of the off-the-shelf Google products, and having them control the camera feed, et cetera. We use UniFi in a bunch of places, which has local storage, and then it pushes from your server to your phone, so nobody else is accessing the data. How do you feel about the privacy concerns with video streaming on-premise for people?

Will Duke: Yeah, privacy is a big deal. I can tell you, the only products that we ever sold, we would have our engineers vet all the encryption. This is where it gets a little bit over my head technically, but there’s like three or four levels of encryption.

Brad Weimert: Me too.

Will Duke: Yeah, three or four levels of encryption, and especially, like our larger clients, it would have to have the top tier of encryption in order to be able to put it on their site. But, yeah, from a security perspective, it’s definitely an issue, especially in this day and age, where everything is going up to the cloud. It’s like, where’s the cloud? Where is it? And oftentimes, they would want to go see the data centers. So, we would go. I’d fly clients. And our really large clients had their own data centers and very large IT departments that even we weren’t allowed to go in certain rooms. But, yeah, security is a big deal now, big deal. Was it like three years ago where Sony got shut down for like a week? The Sony movie studios in California was shut down for a week because of a breach. Like, that seems just crazy.

Brad Weimert: It does. And I think what’s interesting to me about the whole privacy and security concerns are for every story that you hear like that, there are who knows how many where you didn’t hear about it, and nobody knows, right? Somebody gets access, and there’s just a leak, right? Somebody just has access to it. And in today’s world, too, once you have that, if that stuff gets sucked into an AI engine that’s processing it all, it’s gone, like it’s proliferated immediately and used immediately a billion ways. Yeah, that stuff’s terrifying to me. Okay. So, talk to me about exit. So, did you prep for exit? When I think about the different paths that I see entrepreneurs go, I think that the ones that are bootstrapped usually stumble into sale if they do it at all.

And then the ones that are funded that don’t fail, which is a huge portion of them, are guided through the exit process, right? And they have sort of a board that’s looking at all the terms, and they’re very familiar with it, right? The investors that took money in the first place, the whole thing is teed up for exit. So, they’re grooming the company to be ready for exit. I’m guessing that you fall somewhere in the first camp on this, and sort of figured out exit as you went. But did you premeditate the exit, or was it presented to you and you went from there?

Will Duke: No, it’s a good question. So, we were probably somewhere in the middle of that. It was the summer of 2021. COVID was really hard. Like, that was such a hard year for us because we’re a project-based business, right? And so, a lot of our projects stopped. We’ve been doing it at the time for 18 years. And so, summer 2021, we partnered up with a broker just to see what’s out there. And, man, it took off like fast. And it was shocking because you always think your company’s worth something, right? As entrepreneurs, we think our companies are worth a lot more than they actually are.

Brad Weimert: Usually.

Will Duke: And to get that validation, we got– so definitely, like I think about, this is a Jim Collins’ term Who Luck, right? So, we found some key people that specialized in M&A in our space. And so, he put the right people in front of us. Turned out, timing is so important in exits. God, it’s important. But money was hot in 2021. Money was really hot. Consolidation, private equity, big deal. And so, summer, let’s say late June, early July of ’21, and just rapid fire all the way up to, we had five LOIs from different companies that wanted to buy us, which we didn’t even know if that was a big deal or not. Turns out after the fact, five LOIs is like incredible, but we had no idea what we were doing from that perspective. They would use all these terms of hold back and earn out and cash free, debt free, and I’m literally writing down these terms on these meetings going, I don’t know what that means. I’m not sure what that means either. And so, we’re learning on the fly.

All these big boys have M&A teams, that’s all they do. So, it’s me and my business partner learning on the fly, negotiating against really sophisticated finance people. And it was such an outer body experience. Like it was so hard, man. It was so hard.

Brad Weimert: What advice do you have for entrepreneurs that are walking into that process?

Will Duke: Number one, communicate with your family. Daddy’s going to be a little bit in outer space for the next few months. It doesn’t mean he doesn’t love you. But, Brad, it’s literally like you’re basically starting another company. It’s a whole process while you’re continuing to run your company because if the deal falls apart at the end, you still have to have something to continue to run. That’s the first one. Breathe, drink, water, focus on the North Star, which is the goal is get the deal closed. Those are a few.

And also, it is really important to me, Brad, too, is like, I’ve got at this point, a 19-year history with my business partner. His wife and my wife are friends. We’ve traveled all over the place together and my vision was at the end of this transaction, his family and my family will be on the beach playing together, no matter what. And that really helped because there were some stressful times of we didn’t always agree on everything there towards the end. And it was tough, but the North Star was, we talked about relationships. They matter. They matter way more than money. Way more than money.

Brad Weimert: And I think that’s such a valuable thing for people to think about as they set goals because if you aren’t clear in your absolute must and your absolute must nots, it’s very easy to drive towards a goal to the detriment of something that’s very important to you. And if you don’t have that qualifier going into it, you’re likely to do that. So, the idea of having the North Star being and the vision being not just exit, but after exit, I’m going to be sitting on the beach with our families enjoying it, likely was the key decision that allowed you to preserve the relationship through the process.

Well, I want to talk about that because you had kind of an interesting exit because you sold two companies independently at the same time, from what I heard two times the going value of these companies. And there was some sort of odd equity split with you and your partner through that process. Can you give an idea of, just tell me how that flesh of the details for what I just said and then we’ll talk about some of the levers?

Will Duke: Yeah. So, we sold our integration company to a private equity firm that owned a door hardware company. So, if you think door hardware, old musty industry, they wanted to be able to offer integration, newer technology stuff to all their customers. And so, they started an integration division and they started acquiring security integrators. And so, one of us had to stay on board to continue running the company. And the only thing that was going to work was I had to sell my interest in the software company back to my old business partner. Otherwise, it would’ve been a massive conflict of interest. And turns out about nine months after the sale, the CEO said, had I not done that, they wouldn’t have bought us.

Brad Weimert: Where does the conflict of interest come in?

Will Duke: So, the conflict of interest is we’ve sold integration company to the private equity group. They want us to continue to grow in partnership with other 75 branches. It’s a billion-dollar company. What happens if something goes sideways on SiteOwl and Will needs to jump over back into his SiteOwl company, and now he’s not helping 3Sixty grow? And so, that came up a couple times with a few people that gave us LOIs and I just decided to sell my interest back. And so, the bizarre part was I was selling with my business partner and then also against him simultaneously. It was super weird.

Brad Weimert: What do you mean by that?

Will Duke: Well, so I was negotiating directly with Joseph for what we deemed to be the value of SiteOwl at that time. So, I…

Brad Weimert: Because you were selling your shares in it to them.

Will Duke: Right. And then, but we were also selling 3Sixty, which we both wanted max value for. And then the only way I wanted to do it is if they both closed on the same day, which I don’t know why I came up with that now that I think about it. It just made sense back then. I don’t even know if that makes sense now, but I just knew once I had sold everything, I no longer would have any say so. So, it was like I wanted to get all the stuff. And we had six attorneys working on this thing simultaneously. It was exhausting.

Brad Weimert: Good God. One is too many.

Will Duke: Six. After like the fifth month, I’m like, oh, why do I think the world’s about to end? Oh, I’ve been talking to attorneys for six months, only covering worst-case scenarios.

Brad Weimert: Well, how would that change today? The number of attorneys, knowing that, I mean, today, like I look at just the last year for me and how much more dependent I am, how much I send to ChatGPT or Grok versus an attorney. And my first stop is upload that sh*t into the LLM and ask it to audit it because it can go through an audit and it makes mistakes, but so does my attorney and it’s a lot cheaper and faster to use the robot. Do you think you still would’ve had six if you were doing the acquisition today? How would the landscape change for you today if you were to sell relative to attorneys and usage of AI?

Will Duke: So, I think what would change today is any new company I start will be built from the beginning to sell, whereas we never really had any intention of selling. It was just kind of something we were looking into. It turned out to be the right time. The numbers kept going higher and higher and higher. I was like, oh, my God. But I think I would at least do a lot of preliminary stuff with ChatGPT, Grok, whatever, just to get a basic understanding, so you don’t waste a lot of time. I think sometimes you waste a lot of time with attorneys where they’re trying to give you the basics. And so, I’d say like from a foundational level, I would always start with help me understand what this document is, what I’m reading. Show me all the areas that I could really get caught off guard and then come into a meeting with the attorney prepped and ready with questions versus burning five hours of foundational discussions.

Brad Weimert: Yeah, super helpful. What do you think the biggest levers were in increasing the value? So, you sold at 2x what the market going rate was. What were the two or three levers that allowed it to be 2x?

Will Duke: So, we could clearly articulate how we were different. We could clearly articulate how we were running our company. We could clearly articulate how we actually did culture in our company and why it mattered and how it impacted our really low turnover rate. I’ll never forget the time, we had probably three different groups. They wanted to come to our office. It was always after hours because you can’t have a bunch of people in suits walking through your office. We’re a blue-collar company, right.

And they came into our office and they looked like tourists because, in our office, we had pictures of people. We went all in on culture, core values, but it was pictures of people all over our walls. And they were like, what are you guys doing here? What’s going on here? Can we take these pictures? Like, what is this wall of books? I’m like, we’re having fun. We’re here to have fun, right? And so, we take our business very seriously, but doesn’t mean we have to take ourselves seriously. So, it was really a premise of how could we have fun and do business at the same time. And it turned out we didn’t build it like that because we thought it would help us sell, but it turned out that when people came in, like Brad, if you walked into our office, you’re not in the industry, you wouldn’t even know what we did. There weren’t security cameras hanging all over the place. It wasn’t this technical thing. It was people first, equipment second.

And so, I think because we could clearly articulate it, we used EOS to run our company, so we had a clear rhythm of forecast, look ahead. We could articulate our numbers. Our financials were like super clean. For all of you out there that are looking to sell your company, you will not get max value unless your financials are extremely clean. And I’m talking like three years back, minimum. So, those are a few things.

Brad Weimert: Culture, process, unique identifier, and being able to very clearly articulate those. I like those because I can remember CPU. Yeah, that’s great man. I think that culture and values are something that most entrepreneurs think they’re supposed to do, and then they hang something on the wall and point to it. As a friend of mine has said, when did you learn in the journey that culture and values were actually an amplifier and driver and not something to point at on the wall?

Will Duke: Oh, probably, 10 years in, we came up with an acronym, SOLID. And just like you just said with the CPU, we put it in a word so we could remember it. And it was, I could tell you to this day, everybody in our company, I could stop them in the hallway, they could say it, serve others, outstanding attitude, learn and grow, incredible initiative, and dream big. Like those are our five core values. And I would use them everywhere, every day. Somebody would come in and we would be talking about somebody. I’d say, well, which core value are they showing? Which one’s lacking? And our all-hands meetings, we’d give away challenge coins that we stole from the military. And so, somebody would get up and nominate another person based on the core value. We had it everywhere.

And then we took each letter and put each letter up on the wall of like, what’s an example of serve others? What’s an example of learn and grow? The learn and grow wall was books. All the books that we read as a company. We did a dream big wall, which we put everybody’s goals in writing one-year, three-year, and five-year on the wall. And that was when I came up with that idea, people were like, you’re going to do what? You’re going to do what? And so, I taught people how to write their goals and they freaking loved it. And so, that was not built out to help us sell, but it turned out it was something that helped us sell for max value. But what it did was it made our company all about our people. It’s like, if we want to get everything that we want, how do we make sure that our team gets what they want? And it was always about, because I know culture gets so overused, it was almost like, how do we do culture in this company? And I could just tell you, like all the things we did, and that could be a separate podcast, but it mattered. It mattered that people were growing, that people felt like they were seen and heard. They were not just an object. So, that’s some of the things I think about culture.

Brad Weimert: I love that. Also, when I think about goals and I think about sort of the framework and you said something very similar. The framework of if you can help people get what they want, it can help you get what you want functionally. And in some roles, to me that makes a ton of sense. And I think like in sales, for example, in a very commission-oriented environment, it’s like, yeah, if you have a personal goal, let me help you make more money here because that will contribute towards your personal goal. In other roles, I have a harder time mentally connecting somebody’s personal life goal to the company goal. How do you think about those things and where does that come in on a daily basis when you’re managing customer service, tech support, administrative people, et cetera, where they’ve got these external personal goals and it’s on the wall in the company, but it probably doesn’t align directly with the company goal?

Will Duke: I’ve thought about this a lot over the years, Brad, and it’s really, if you communicate with people on their frequency, you’re much more likely to connect. It’s really understanding on a deep level, like what motivates people. And it turns out making more money is not always the biggest motivator. It’s almost always that for salespeople, but for different roles, it’s, I want certainty in my role, I want to know what’s expected of me, I want to be acknowledged when I do a good job. And understanding how each person’s brain and heart work at different levels, different vibration levels. And if you run a company with intention where you’re trying to seek that out, you’ll find it, if you care.

If you care about running a great company, because there’s so much mediocrity in the world right now, it’s just gross, but it takes a lot of energy and you cannot rush greatness. You can’t. It takes time and patience and heart, love, love above all, life philosophy of expecting people will do the right thing. If given an opportunity in an environment, like 9 times out of 10 people are going to do the right thing. And for the 1 out of 10, you learn and you move on.

Brad Weimert: So, let’s talk about the next chapter. So, you sell and I think that the notion of you sail off into the Caribbean sunset for most entrepreneurs is not real. And as we started, you mentioned yesterday that you haven’t been doing a business for three years and now you’re itching to do something, but you have been doing quite a few things. And a lot of people immediately when they sell, freak out and either get depressed or they’re like, what do I do with the money? How do I deploy it right away? And one of the things you did is you joined Justin Donald who’s great friend of mine, long-time friend, his Lifestyle Investor group.

And we were in Austin together, all in a room a few weeks ago. And one of the things he said was, most people join the group and they’re looking for the deal flow and they’re looking for how do I learn how to get the best investments and leverage the group to invest in the best things. And Will came in the group and he did no investing for the first year. He had no deals that he was a part of. What were you doing? And how did your journey into investment start post exit?

Will Duke: So, for 20 years, head down, both eyeballs in both of our businesses, I didn’t really know a lot about investing. But what I did know was I wasn’t just going to wire over millions of dollars to my legacy financial advisor so they can give me these 30-year projections of what my money could look like. That seemed boring, that seemed old, but I also didn’t understand private alternate investments, so that felt really scary. So, the way I fill the gap is through education. And I think about groups. Justin and I happen to have a couple mutual friends, both actually in Strategic Coach, ironically.

And I was just asking, in fact, Kary Oberbrunner did his audiobook. I was hitting golf balls on the range and I was listening to the book and I was like, that’s my friend Kary interviewing Justin. Like, wait a minute. And so, I was like, what’s the deal with this group? And so, the first year was, again, back to the terms, you talk about every three-letter acronym out there from SPV to like, I mean, just like every time somebody would say these terms, I’m like, I don’t even know this language. And so, I was like, I have to understand what I’m doing before I start zinging money all over the place. And so, that’s what I did.

I was also still inside 3Sixty, so I wasn’t super active in the group, but I had to understand the terms. I had to understand like, what’s a diversified portfolio for my family? What does that even mean? What are the different sectors out there in the market? Like sectors, like what? What do you mean sectors? So, I had to understand that. And like I’m just the kind of guy, like I have to know what I’m doing. And it took me 20 years to earn this money. I’m not going to just spew it off. I can hop on a plane and go to Vegas if I want to light money on fire.

Brad Weimert: Right, right. If you want to put it all on black. Well, quite honestly, you started by saying you didn’t want to give it to your legacy advisor, which is putting it on black. You didn’t want to throw it into some alternative investment because you felt like that was putting it on black, also might have been. And a year later, so you go through learning and what people in the group know you for now is, at least one of many things and kind of the reputation that I got from you is putting this ridiculous deal vetting engine in place on the backend to really, really, thoroughly vet the things you get into. Tell me about how you approach any investment you get into now, and what the steps are to see if it’s a worthwhile deal?

Will Duke: So, actually, I was talking to Ryan Casey the other day about this in our board meeting. And onboarding an investment is very similar to onboarding a new employee, onboarding a new customer. There’s things that happen beforehand. There’s things that happen at the beginning, during, and after. And every investment’s got a life cycle. And so, I have to understand what the company does, how they make money at its very core, at like a really fifth grade level. You deliver this, you get paid for that, and walk me through that.

And then all the nuances of timing, right? Because investment is about timing is I put my money in here, it comes out this way in this format. And what are the ways in which it might not come out? And tell me all the ways in which things can go off the rails. And really, I was actually working on it this morning, Brad, because from the retreat, I pulled six or seven new questions that I added into it. And it was really a function of, in the beginning, I wasn’t quite sure which questions to ask. And then I spent probably 5 to 10 hours going back and forth with ChatGPT on here’s my questions back and forth, back and forth. What are we missing? What are we missing? Okay, why is this question important? All right, get rid of this one.

And it was a function of the questions are all extremely direct. I’m not looking for a buddy. Every dollar I send out has to come back more than a dollar. Otherwise, what was the point? And coming into the fourth year in the group now, I now have money coming back out of some investments that I have to go back and redeploy. And so, it’s interesting to have that lens now of I’ve got two calls today of investments I’m looking at and they’re going to get the spreadsheet, which is…

Brad Weimert: Well, so let me frame this a little and let’s talk about the spreadsheet. So, for anybody that’s like, I don’t know what the f*ck you’re talking about, investments, auditing, questions that you ask people. So, you’ve got a whole litany of different things you can invest your money in. But let’s say, it goes anything from somebody tells you that they’re going to build out a fourplex and they need money to do it, to I have an oil and gas fund, to I have a solar company that I want you to invest in, to hey, I’ve got an opportunity to buy into X AI, to whatever, you name it. And you can invest in any category and there are companies out there that will facilitate that. And usually, it’s somebody that’s running the investment and then raising money to do it. So, any of these things come across your plate, your first step is to send them a big ass spreadsheet of questions. That’s my basic understanding.

So, tell me just what are some of the things that you’re checking for on that? And you said they’re going to get the spreadsheet and that’s what you’re referencing. So, what are a few of the questions and some of the basics that you’re trying to audit when you are looking into an investment?

Will Duke: So, the first section is like all about the sponsor and the team.

Brad Weimert: Meaning the company that is running the investment, so the GP of the investment.

Will Duke: Yeah. And so, it gets to a point now where if we just use something very basic, like multifamily, right, the real estate investment, how many years have you and your team been doing this? One year, three years, 25 years, where you’re doing something else last year, and so everything is around probability and risks. I think in terms of like qualitative and quantitative is when I look at deals too, is like, you’re going to be in a relationship with these people for three, five, seven years. Will you enjoy that? That’s the qualitative part.

You can usually get that off the presentation. How much time did they spend on this presentation? Are these slides? There’s a typo in the slide. There’s a typo in the last three slides. Like, that kind of stuff drives me nuts, especially the days. Then it’s like company and entity structure, financial transparency. I got this from Bo, three years of audited financials. He won’t invest in a deal, Bo with DLP, one of our real estate groups that we invest in, three months of audited financials.

And then it’s down to the deal. Tell me specifics about the deal. I put my money in, and once the capital calls, when does the money start coming out? How are you calculating NAV, net asset value? If your NAV goes down, do my distributions go down? Like, all these things that I’ve kind of learned over the past three and a half years that have actually happened are now baked back in there, goes down to reporting and communication. I will not invest in anything if they don’t send out at least a quarterly report of what’s going on. You have to tell me what’s going on. Otherwise, I’m not interested.

And then it’s the worst-case scenarios, compliance stuff. But it’s like 67 questions. It’s interesting too, because they’re really good sponsors. We’ll be like, wow, these are great questions. Let us get on these and we’ll get right back to you. The other ones are like, take three, four, or five days and like, immediately done, I’m out. So, how long they take to get back to me, and then how detailed they are with the questions or with their responses? Or are they annoyed? Are they irritated that I’m asking all these questions? If they are, that’s like a major red flag.

But more times than not, I’ll send this beforehand. I’ll get it back and then I’ll pick out the four or five things and that’s the agenda for our meeting. But it’s evolved over time. I don’t know if I would’ve been– when I first started, I don’t know if I’ve been bold enough to ask these questions because they’re super direct. But once you wire the money, you’re kind of done. Like, they don’t want your opinion. You’re not going to their board meetings. You’re not going to sit in a strategy meeting. So, like, you know, and above all, this gets oversaid a lot, but it can’t be ignored, the sponsor over everything.

If the sponsor’s a good human, how will they react when things aren’t going well? And then the investment, second, because I’ve got a lot of money with one sponsor and three or four different investments. And so, that top section of the sponsor, I would just pull out and be like, all right, has anything materially changed in your company executives in or out? Okay, cool. Now, let’s talk about the investment.

Brad Weimert: Yeah, I think the parallels here are, you hear people say, bet on the jockey, not the horse. Bet on the entrepreneur, not the business. First and foremost, it is who is running the show, right? And do you have confidence in them? I love that. Well, Will, I want to learn from your investment strategy and I want to see your spreadsheet.

Will Duke: I’ll send it to you, for sure.

Brad Weimert: That’d be amazing. Yeah. Where can people find out more about you if you want them to find out more about you?

Will Duke: Oh, I’m on LinkedIn.

Brad Weimert: Beautiful. Will Duke, I appreciate you carving out time.

Will Duke: You got it, buddy.