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Michael and Samantha on Scaling a Business and Planning an Exit

Summary

Richard C. Wilson hosts Michael and Samantha, co-founders of a large ATM network, for a conversation about building a business, choosing partners and preparing for an exit. They describe how a wholesale model and a focus on serving both ATM owners and card holders helped shape the company. They also explain how they treated competitors as potential partners, set up deals so each side had a reason to participate and fixed recurring operational problems as the business grew. On the sale, Samantha discusses clarifying the outcome they wanted, building relationships with potential buyers before going to market and keeping more than one buyer engaged. Michael describes how savings and passive income gave them room to negotiate. The discussion also covers relationship-based networking, understanding what the other party needs and their shift toward investing, including lending for cash flow. Founders planning a sale, investors, capital raisers and family offices can use these lessons to assess business growth, buyer relationships and exit readiness.

Key Moments

A strong exit starts well before a buyer makes an offer. In my experience, founders and family offices get better decisions when they understand the other party, define the outcome they want and build trust over time. In this Family Office Club fireside chat, Michael and Samantha describe how they built an ATM network, sold the business and shifted their attention toward investing.

Their story offers practical lessons for founders growing a company, investors evaluating opportunities and family offices building relationships with operating businesses. The conversation touches on distribution, partnerships, operating discipline, buyer conversations and the personal financial preparation that can give an owner room to negotiate.

Build a Model That Gives Each Party a Reason to Participate

Samantha describes looking for a wholesale approach in an industry where many operators focused on retail sales. The idea was to make the economics clear for the business, the ATM owner and the card holder. That structure helped make the service worthwhile across the chain. For a founder, the lesson is to examine how value reaches the end user, not only how the company collects revenue.

Michael also emphasizes serving customers. His framing is straightforward: when a business consistently serves its client and that client's customer, it can earn goodwill and future opportunities. Family offices assessing a private company can look at whether its model creates durable value for customers, or whether it depends on a narrow transaction that is difficult to repeat.

The founders also viewed competitors as potential partners. They worked with others in the sector, including through a buying group, to improve their position when negotiating with suppliers. That approach takes a clear view of shared interests. In a family office portfolio, a company may find room to grow by building partnerships across its industry instead of trying to control every part of the value chain.

Make Operations Easier as the Company Grows

Samantha explains that she paid attention to recurring problems and tried to fix what caused them. Resolving a single complaint may help one customer. Removing the process that creates the complaint can make the business easier to run for everyone. Founders can use that habit to improve service and avoid adding volume to a process that already frustrates customers or staff.

For investors, this is a useful operating question during diligence: does management look for the source of repeated problems? A company can grow while carrying avoidable friction. Family offices evaluating an operating business can ask how the company handles customer feedback, which processes break down repeatedly and who owns the work of improving them. Those conversations can reveal how management thinks about growth beyond the headline numbers.

Michael's advice to a founder who feels growth is slow is to find someone with relevant experience who can help the company move faster. The cost of support needs to be considered alongside the opportunities that may be missed when the company waits too long to add the right people. For a family office backing a founder, this points to the value of practical operating relationships alongside capital.

Plan the Exit Around the Outcome You Want

Samantha describes revisiting the sale question over time: whether to sell the whole business, sell part of it or continue operating. She suggests beginning with the result the owners want. The right buyer and structure depend on that goal. A founder seeking a clean transition may value certainty and a straightforward handoff differently from an owner who wants to remain involved.

She also explains how she approached potential buyers. Relationships existed before the formal sale process, and she contacted more than one interested party when they were ready. Keeping multiple buyers engaged helped preserve options and maintain momentum through negotiations. Richard's framing is that founders can plant those relationship seeds early, while investors can build familiarity with companies long before an owner decides to sell.

Michael says savings and passive income helped the couple feel less dependent on the sale proceeds. That financial preparation gave them more room in the negotiation. For founders, the personal balance sheet and the company exit are connected. For family offices, understanding an owner's priorities can make a conversation more productive than focusing only on price. When transaction terms include legal or tax questions, talk with your attorney or CPA.

Build Relationships Before You Need Capital

The discussion applies the same principle to fundraising and investing. Michael describes learning what someone is seeking before bringing an opportunity to them. Samantha warns against pushing a pitch at people without first understanding who they are or what they want. For founders raising capital, a relevant, well-timed conversation starts with listening and knowing what the potential investor values.

That approach also helps family offices source opportunities. A strong relationship can clarify an investor's strategy, liquidity needs and preferred role before a deal is presented. It takes time, but it reduces mismatched pitches and gives both sides a better basis for a future conversation. To learn more about building relationships with other family offices, start with the practices that make trust possible.

Michael mentions a focus on lending and cash-flowing assets as part of their investment activity. The broader point for investors is to understand the job an investment is meant to do within a portfolio. Founders can apply the same discipline to an exit: know what the other party needs, know what you need and shape the conversation accordingly. Family offices can also review how to conduct due diligence and how family offices source direct deals as they build a repeatable process. Richard's central framing is simple: good business relationships begin with clear outcomes and a sound understanding of the people across the table.

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Full Transcript

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0:02 We have Michael and Samantha with me here. Um, they spent over 28 years building one of the top five largest ATM networks. Um, they're both founders, entrepreneurs, probably much like yourself. Um, they grew it up to an 8 figure um, valuation, had their exit last year, went through the negotiation of that exit, the the process of deciding should we sell, should we not sell, etc. Um, and now they're focused on investing their own wealth, reducing tax liabilities where possible, helping others achieve financial independence, and exploring how to do both passive investing while using their entrepreneurial driven brains just like a lot of us here in the room. So, I think a lot of you are going to connect with the comments they share here today. And, uh, would either of you like to add something for a introduction on who you are?

0:50 You did a pretty good job there, Richard. I definitely want to thank you. um in and even thinking about what we did with our uh ATM company, I think about what you've done here with Family Office Club and it's about getting the best of the best together and finding ways to work together and that's what we did. I I think that was a big key for us as I've seen it for you as well. Sure. Great. And Michael, I think she covered it. Uh we just like to partner with people that are doing a great job in their specific uh niche and uh see if we can help uh grow that by putting a little gas on it. Sure. And I know it wasn't uh one of the planned questions, but I remember when we went uh golfing last year um in 97 degree nice weather in Scottsdale for 4 hours. Um you mentioned Samantha that one of the things that helped you guys grow faster is thinking differently about the ATM business. I think you structured your acquisition of deals differently or you thought about it more of a wholesale and mass distribution model if I remember right. Can you comment on that and just how that played into your success? Yeah, you you have to remember we started in the ATM industry when it started. So as soon as it it didn't have to be bankowned. So we actually watched the entire bell curve of the industry. But when we first started, uh, everybody was really doing retail sales, even for people that wanted to own their own

2:07 portfolio of ATM machines. So, we were looking for a wholesale environment for ourselves, and figured somebody else was probably looking for the same thing. And I really came up with um I Mike and I were talking about do we is this something we want to do? It was our side hustle. Uh, and I said, "Look, if we can come up with a program where we're not cons consistently renegotiating somebody else's portion, like they always know what they're going to make and it's a win-winwin. Win for us, win for the client, and win for the client's client. That's a company I or an industry I could get behind." And I said, "If we can do that, I'm in. If if we can't do that, I'm out." And we always stayed true to that. Got it. Okay. Great. Thank you. And um so Michael, what made the difference in your mind being able to scale to eight figures while many people in that business maybe failed to scale to seven figures? What what would you say was a difference maker? Uh I think uh the difference maker for me was it was a brand new industry and we wanted to serve everybody as many people as we can. So the more people we served and we I let me back up a second. If we serve our client, which is the ATM owner, and then serve the card holder, we will get served later. And I think in that business, continuing to serve

3:23 others actually helped us grow a lot faster where there are so many people that were always looking to be served rather than serving. Right. Right. Um, and Samantha, what else would you say you guys did besides thinking about it differently from a wholesale perspective, etc. that that got you to the eight figures? Oh, the actual purchase. Yeah. Or like like what what led to you being able to scale to that level? uh which was different. Maybe I I think we looked at um what other people might have considered our competitors in the industry. We looked at them as potential partners. Uh so there were really ways, hey, why don't we all combine together and we kind of created a buying group and then we could go to somebody else and negotiate harder and then it was everybody won and we just always figured there was enough of the pie to go around. uh if you try to keep it all to yourself and think of it as you know you're the only one that this is going to serve or this is the only way to do it or this is the way it's always been done which there was no road map for us so maybe that that helped um but if you really think about the pie is big the world is abundant there's plenty for everybody just find ways to work together that work well with the right partners then it it works awesome yeah Brenton from Walt Construction was just saying they look for cogp deals and um tomorrow we have a exponential investor panel which is the heads of other

4:39 investor clubs at our investor club event. It's the exact same thinking that we see that in some of the most successful people we've ever met. They think differently about how to get mass distribution, how to do partnerships and not see people as competitors, you know, like a scarcity mindset. So, that's great. Um, and then Samantha, for the exit, I know you led a lot of the negotiation and helped structure it. What did you learn the hard way? what was amazing and you would do it the exact same again if you had to go through it again because I'm sure there's some people here in the room that are trying to figure out like we heard on the last panel should I exit now should I wait till interest rates go down a little bit more uh etc what what would you learn during the exit um one of them is you need to know your own outcome like what is it you're looking for what like I I every few years we would think like oh do we want to sell do we want to sell part do we want to sell all um and really it cames down to like what's the outcome you're looking for uh and how can you do it? I I keep joking that I want to write a book uh negotiate like a girl um because the ATM industry is full of men. And so ultimately when it came down to it, I will tell you what I really did that changed the price is um we you know kind of talked about selling over the years.

5:52 I'd reached out to some people in the industry. It was just sort of a soft float and then eventually we said like okay now we're ready to sell. So, I walked up to one one potential buyer and I said, "Hey, look, I know we've kind of talked about it in the past. We're ready. We want to sell and I want to give you first look." And the guy was like, "Thank you. That's totally awesome. I really appreciate it." That went a long way to, you know, creating a good relationship. And then I walked over to the other guy and said the same thing. Right. Right. And it took a while for everybody to kind come to the table. So, I was like, "Hey, how's that going? Where we at with that?" and you know eventually oh well here and they're floating out low numbers and I was like yeah well you kind of waited so you know between then and now you know I've I've floated it out to a couple other people and then I kept them both in play and that was the huge strategy you know if you have one buyer you really don't have one uh maybe people would lie and say they had one if they didn't that's not a game I wanted to play I feel like that's bad karma um but keeping them both in play and knowing how to sell my company to each one of them when the outcome for each of them was different if they purchased me.

7:01 There's a lot of different insights there. So, one is to plant seeds early. So, by the time you actually do want to sell, they already know you, trust you, hopefully like you, maybe have even started some light due diligence on who you are and seen you at some events and you can follow up with them when you're in town. Um, but then also, you know, if you go to someone first, use that and tell them, hey, we're coming to you first. And when you go to the next person, say, you're one of the first two people we're coming to out of 50 that we could have. Uh, and I guess play those cards. And you know, when you're an investor acquiring something, you want to be the only one at the table. When you're selling something, you want an auction and get maximum price is generally right. So, Michael, I've heard a saying that um all all of my wealthy friends sold too early. You know, basically like the only way you get wealthy is have some sort of exit and you could always hold on to something longer. So, for you, what made you confident that it was the time to sell? We had um operated the business for over 25 years. We had had 401ks. We had cash benefit plan. We had a ton of money in savings. So we could actually retire just based on the money that we had put away over the years. So we figured at that point in time when we were going to sell whatever we sold for would be icing on the cake. So for me it actually I I sort of didn't want to sell at the time but it actually ended up being the exact right time to sell. But I think what made it easier for me to swallow is we had already put enough money away in investment in investments and the investments were creating enough passive

8:18 income to cover our lifestyle. So we didn't have to worry about what the company company actually sold for. So that I think that even helped in the negotiations is we just really didn't care. Right. Well, and can I add to that? Um we because we saw the entire bell curve of the industry. It had actually gone through mergers and acquisitions about three times. It was on really its fourth round. There were like three huge ATM companies, several midsize. We were at the top of the midsize and all these little guys which most of them were our clients. And I was like, if we miss this next round of M&A, we might not have a buyer. And now is the time to go because now we're we're selling to our strengths. So I played, you know, if we were the sixth largest, I played number four and five against each other and let them battle it out. Sure. Yeah, it makes sense. Um, Michael and Samantha have both spoken at a couple of our mastermind events, which we host about a dozen times a year. And at one of them, Michael, I remember you saying that one of your strategies is that when you think of someone who might be a good JV partner or to work with them, you say, you know, "Hey, Sarah, I thought about you. Here's a little personalized video you record on your iPhone while walking. Shoot it over to them. It's just like a 1 to two minute video." And that works super well for engaging people that maybe haven't talked to for a while. Um, any other strategies like that? Because I know both of you network a lot, have a

9:34 powerful network. Any other tips for networking with other family offices? I think creating the relationship and going deep with that person. So then you actually know who they are, what they're looking for, what their investment strategy is. So then I know what to bring to them when I have an investment and I'm looking to raise capital. So many times you will be in a room like this and everybody's shoving their deal at you. I call it being pitch slapped. And if that didn't happen 20 times last night, it happened 30. And nobody even knew what my name was. So, and I'm wondering and I'm wondering why they feel they can't raise capital. I know why they can't raise the capital, but they don't want to listen to why it what works works. And I think getting to know somebody, we have a room here of like two or 30 hundred people. And if I meet five people and we get to go deep, that's five people that are in on my bench that when I need something, I can reach out and they may or may not come alongside me because we actually had a real conversation. Right. Right. Yeah. I think everyone's been pitch slapped a few times when I went to any any event.

10:34 And it that's the opposite of what I recommended during my opening statement today. And I know one thing that Samantha and Michael both really good at most events I see them up front being attentive, paying attention, making eye contact with the speaker, maybe asking a smart question, and there's some of the more successful people in the whole room. And um that stands out to me just after hosting the events over the years. But um Samantha, what do you think is about your your mindset, mental models that led to you being successful in the business? Maybe how you think about challenges, problems, about growth, um etc. Um yeah, we always tried to set up, we always we just called it the win-win-win strategy. So everybody in the chain has to win. So and everybody's motivated by something. So learning how to properly motivate somebody and set it up. So if you negotiate so hard with a vendor that they don't make anything when you call them they will not pick up the phone. So like that that's not a good strategy.

11:29 Everybody needs something out of the deal and we're all business people trying to you know employ people and make things work. So that was a big one. Uh another one is I employed the PETA principle uh the pain in the ass principle and that is if something was a total pain uh Mike might actually fix the immediate problem. And then I was like what created the problem? How do I fix the thing that created the problem to begin with? And when we sold, so we ended up selling to a company almost our size. Uh so they effectively doubled. They had uh 75 people on staff and we had four. I mean, so by taking the PETA principle, you're like one little microscopic thing changing that it's not really going to change anything. Well, you know, over x amount of years and x amount of uh processes, it really does change things dramatically. So don't overlook the small things and think that they don't matter. If you have a broken ship and you pour gas on it with a bunch of clients, now you have a bunch of clients on a broken ship and you don't want that. So fixing it along the way was definitely key. And that is really the whole constant never-ending uh improvement principle that we used with everything. It was like how could we do it better? This sucks. If it sucks for us, it sucks for somebody else. What can we do to fix it? I mean, there are

12:46 things that are complete industry standards now that like came out of my head, you know, and you're just like, "This is such a pain. How can I got not, you know, not do that?" And like calling people and saying, "Hey, do you have the same problem? What can we do about it? What do how do you handle it?" And that created a lot of our efficiencies as well. Awesome. Yeah, that's really interesting. I mean, four employees versus 75. I mean, any founder can relate to the difference that would make, right? There's a saying that uh Joe Polish taught me that um instead of the squeaky wheel gets the oil, maybe the squeaky wheel gets replaced and then there's no longer that squeaky wheel in your system. Right. Especially with AI. Yeah. Exactly. Um so, Michael, if somebody's growing right now and they're in the audience and they're making progress, but you know, they're they're moving slowly. They feel like they're not they're not growing enough and it's going to take them forever to meet their goals, what would you encourage them to do or coach them to do as a entrepreneur that's had an exit? I' I'd coach them to find somebody that's been there, done that, that that can go faster and help them scale better because it's not what it costs to bring that person in. It's the lost opportunity cost for not getting there faster because you may miss the boat and miss some of the the upside that you can actually create by actually putting the right people in the right seats at the right time. Got it.

13:56 And then um quick question for both of you and I'll get to my final question is just um being in this environment after having an exit. I know you like real estate for part of where your energy is going. Uh any two to three upcoming midterm trends that you're just tracking real closely and you're not sure about your play in that area yet, but is a little subniche that you're excited about and keeping an eye on? So, it it's been set up here a number of times today to be the lender and we've been lending money in the uh Arizona uh area for the last year and a half and we're raising a fund around that right now to get more money out on the streets cuz at the end of the day um people got into the mult in my space they got into the multif family they got into some of the triple net and some of the uh cap rates have compressed uh distributions have gone down so now they're looking for cash flow I actually did a talk about it a year ago uh at another event who instead of who moved my cheese, it's who moved my capital and where did the capital go? The capital went to cash flowing assets. So me being a cash guy raising capital, I had to figure out how to get my investors into cash flowing assets. Got it. Okay. And then for each of you, maybe starting with Samantha, what's a um a big insight we could leave the audience with today that'd be really powerful for investors to hear or somebody on the the founder capital raising side?

15:12 Um, well, I think when it comes down to an exit, it goes back to knowing your outcome. So, a lot of people ask, you know, like, did we sell to a PE firm? No, we sold within the industry because I wanted to be done. Uh, and so getting out was the goal. And so, keeping your eye on that. People will try to move you off your marker. Uh, the last part was make sure you get paid. So, there are a lot of people that will you'll sell your company or you're supposed to stay on as a consultant and then they fire you or you don't get the next payment. So work it out so that you're getting paid. Right? The last comment is so important because nowadays with PE agreements being so complex, someone might say, "Oh, we'll give you 11x, not 7xida, but half of that return is in stock in this third party company that you may be held hostage to when they get recapped or it may never happen." And it wasn't really 11x. You actually would have been much better off selling to someone in the industry and then um planting those seeds really early like you said. Um, if you're an investor, you should be planting seeds with CEOs like Samantha and Michael were five, 10 years before they want to exit. So, they're comfortable with you as the buyer and they come to you first because you're a strategic buyer. Um, and then they'll trust your expertise and you'll get a deal at a better valuation because they trust you, not the private equity firm with a army of lawyers and a 300page legal agreement, my experience. Uh, Michael, any last insights from you? Um,

16:30 understand what the person sitting across from the table from you actually needs. Like you could actually sell an investment for tax purposes. You can sell an investment for cash flow. You can sell an investment for upside equity, but if you don't understand what the person on this other side of the table needs from you, they're not actually going to listen to what you have to say. Uh, and that goes back to like last night. Everybody's got a great deal. Everybody's trying to get somebody's money. And I'm not even looking for a deal. But clearly I had that look, the sign on my forehead, pitch me your deal. and that's not what was going on. It'd be much nicer to get to know you, figure out who you are, what you're looking for, and then we can have another conversation later because then you'll know what I want and I know what you want. Maybe we each have something each other each other needs. Right. Right. Figure out exactly what the other person wants. I know that Samzel had a famous story in his book called Am I Being Too Subtle where he was trying to buy a whole block of real estate and one lady was holding out as 85year-old who would not sell her house.

17:27 Nobody could get it done. And Sam said, "I'm going to go there in my Harley, get it done myself." He went there, knocked on the door, had a cup of tea, and the lady said, "Well, my dog is buried in the backyard. That's why I won't sell." So, they exumed the dog, bought her a new house, moved the dog, buried her they buried it in the new backyard, and got the deal done just by listening, getting to know her, and having a cup of tea versus just making offers that were higher and higher. So, um, it's related to that comment. Yeah. Awesome. Well, if anyone wants to connect with Michael and Samantha, I think you're going to be here the rest of the evening and during the cocktail hours. Um, after this, we're rolling forward with some more content. So Charlie's going to welcome up the next speaker, but let's give him up round of applause. Thank you. Thank