Brian Dukes: Turning Experience Into Exit Wisdom for Founders

Intro: Broadcasting live from the Business RadioX studios in Houston, Texas. It’s time for Houston Business Radio. Now, here’s your host.

Trisha Stetzel: Hello, Houston. Trisha Stetzel here bringing you another episode of Houston Business Radio. I’m really excited about today’s guest and the topic. Today’s guest is Brian Dukes, managing partner at Exitwise and M&A advisory platform, helping business owners prepare and successfully navigate the sale for their companies. Brian’s journey started in Big Five consulting, followed by his MBA at the University of Michigan, and instead of taking the corporate route, he joined a Ford Motor Company joint venture and then co-founded a digital marketing agency that became an industry leader in automotive technology. After building and selling that business, he discovered his passion for helping other founders through the exit process. Today, Brian and the Exit Whys team are reshaping how entrepreneurs think about exits, removing the stigma, focusing on readiness, and teaching owners how to build companies that are ready for whatever comes next. Brian, welcome to the show.

Brian Dukes: Thank you so much.

Trisha Stetzel: I’m really excited about our conversation today because I think we both have this passion around this topic. But before we get there, tell us a little bit more about Brian.

Brian Dukes: Is it a natural reaction to always feel a little bit embarrassed when you hear your own intro? Yes.

Trisha Stetzel: And I do that on purpose because we don’t take the time to do it for ourselves. So I did it for you. It is my gift.

Brian Dukes: Well, I appreciate it and you know it. It is my story. It’s a summation of a 20 or 30 or so year professional career. And I’m super passionate and appreciative and excited about what I’ve done. But, you know, to put it into. And full sentences like that, it’s always, always nice to hear. So thank you. Um, you know, it summarized, uh, pretty, pretty well, a lot of the ways that my, uh, my. Professional wins have blown. I mean, really? Yeah. In summary, I didn’t know anything about entrepreneurship when I was growing up. My growing up in metro Detroit, uh, my dad worked at Ford Motor Company for 30 years. My mom was a school teacher, then turned nurse. And, you know, the traditional path of professional, uh, kind of professional life, you know, set forth in front of me. And it really wasn’t until after grad school that I, just by luck, uh, fell into a joint venture. I was 15th employee, uh, a joint venture, uh, really started to cut my teeth on. Wow. If I make a decision, it actually matters. Something actually happens or doesn’t happen. Um, and it really, uh, got me excited about, you know, being part of a small team and being part of this crazy ride that I now understand to be, um. Entrepreneurship, uh, three years after that made the official jump and, uh, was a co-founder of an automotive marketing technology company, uh, Enterprise Data, we launched in 2008.

Brian Dukes: Uh, our first client was soon to be bankrupt. Chrysler, uh, many, many horrific, difficult, challenging, ridiculous stories that came out of those next couple of years. But ultimately, we made it to the other side. Um, ran M&A through that process, saw, um, you know, saw the positives and negatives of M&A throughout. And then I personally exited in 22, reconnected with an old friend who was also, uh, an aspiring entrepreneur. And, you know, we really connected to this idea of M&A, helping business owners understand and successfully get through an exit is is just a, It’s an underserved market. I like to say that it’s really cool to help a business owner sell $1 billion business, but there’s just not enough people focused on helping the everyday entrepreneur in lower middle market and SMB to find the exits they deserve. And so, you know, that’s really you know, it’s a little bit of my journey, a little bit of my why. But I feel really passionate and love working with business owners and thinking about their futures and really helping them get on a path of what that what that future might look like.

Trisha Stetzel: Yeah, I love that. So can we talk just for a minute about what makes Exitwise a little different from all of the other businesses that are out there doing?

Brian Dukes: Yeah, yeah, I appreciate you asking that because we can all look very similar. If you go to 100 different M&A advisory firm websites, many of them look very, very, uh, like they were designed by the same by the same web site house. Um, really a couple things. The first, uh, which I’ve, I’ve touched on a little bit, is this idea of everybody that’s part of this business. We are, are and have been operators that have built and sold our own businesses. Uh, we know not just what it takes to build a business and what it takes to exit a business. We we understand the trials and tribulations that are inherent with entrepreneurship. And as much as we’re led to believe that, you know, you can build a business, $1 billion business in six weeks with AI, uh, by yourself, uh, for for the rest of the 99.999% of the world. Um, we have a lot of horror stories and bumps and bruises. And I think, um, you know, where we come from is a place of, of empathy and understanding that this is a difficult road and that as founders, uh, as owners, as CEOs, uh, your time is constrained and you have a lot of, uh, a lot of responsibilities and a lot of things to worry about. And exiting isn’t always, um, you know, top on your list.

Brian Dukes: And so we we really beyond being a functional M&A advisors and bankers, you know we are there to be a coach a mentor having actually done it ourselves and provided maybe a little bit different insight and guidance than, than the typical investment banker. The second, um, is, is in our preparation or support of the preparation process. Uh, we’re big believers. You’ve heard me say it before in some of our conversations. Um, I think exiting a business, there’s a bit of a stigma around it. And, uh, part of that is, as CEOs, we’ve always kind of known the answer. We’ve we’ve known what we’re building. People come to us whenever they have a question, and we’re used to knowing what to do. And, uh, when it comes to, to, to selling a business, oftentimes we’re not lucky enough to, to do it multiple times. And so we don’t know who to go to. We don’t know who to trust. We, uh, we have built something so important to us and to our team and to our families that we, we, we struggle to to lean into somebody that can assist us in selling. So what that means is you put it in a closet and you hope that it just works out someday down the road. And then somebody knocks on your door one day and says, hey, you have something interesting and a value.

Brian Dukes: I’d like to buy it. And it’s like chaos reigns. And and that is ultimately why you see such a high failure rate in M&A. So getting back to your question, our big beliefs, uh, is, is working with businesses earlier in the process, understanding value, understanding how buyers would look at your business, really making it. You know, another CEO responsibility is thinking about your future exit. And that could be, you know, ten weeks from now, it could be ten years from now. It’s really thinking about it in a way that’s, uh, exiting my business is part of my responsible as an owner, and I need to start preparing. And so we just spent a lot of time early doing certified valuation work, helping organize financials in a way that a buyer could potentially understand. Um, you know, I said it already, the idea that we give you the view of the buyer and we we help you practice answering some of those questions, um, and thinking through the questions that you’re going to get from potential buyers to start preparing for that when you, you know, when you have time for it versus the stress of I have to respond in the next ten minutes and I don’t know the answer. Yeah.

Trisha Stetzel: All right. I want to tackle the idea of doing the hard things. So people who are listening have done a lot of that right. As entrepreneurs, we do. We tackle a lot of doing the hard things and we learn our lessons. We, you know, fall down on our knees, we get up and we go do it again. And then we fall off a bicycle and, you know, it’s perpetual. Um, so they’ve already done a whole lot of hard things. You’ve done them. I’ve done them as an entrepreneur, and thinking about this exit process sounds really hard too. So can you take me through just your thoughts on doing the hard things? You know, whether it’s personal or professional and what really makes us tick as humans?

Brian Dukes: Mm. Boy, I can take that in a lot of different directions. I’m a firm believer, just generally in doing hard things. Uh, we we, I think we’re trained at an early age that we have some mythical retirement. Or maybe we sell a business, you know, for a real amount of money early in our careers. And we sit on a beach and play golf or sail or fish or whatever we want to do. And, uh, I like to do many of those things. Uh, and I love being with family and friends, uh, and leaning into that part of my life. With that said, uh, for most humans, um, we need we need to accomplish tasks. We need to take on challenges, we need to do hard things. And I often say as I mentor, um, even, you know, junior resources, it could be like rewiring your bathroom, uh, putting up wallpaper. Um, you know, it could be building a business. You know, it can be really anything. Learning a new language. Um, it’s. I’m a big believer that a life without challenges is one that ultimately I don’t think is particularly fulfilling. So that’s just a personal belief. I don’t know that it’s a hot take in any sense, but I just I talk to enough business owners that go through a process.

Brian Dukes: They get to the other side, and then they’re somehow disappointed because they haven’t they haven’t built a plan for that future. Um, they realize too late that, um, it isn’t going to be fulfilling to travel around the globe 20 times. Um, you know, the first time was really, really fun. But after a while, you know, you just you just kind of, you know, you need to accomplish something different. And so I think doing hard things is, is really, um, you know, is a core belief of mine. Um, I guess specific to, to building and selling businesses, uh, I think, uh, I don’t know that any M&A advisor investment banker would say that selling a business is easy. But as you look at the, uh, this the scope or the scale of that discomfort or that pain or the difficulty of selling a business, it does not have to be a root canal. Um, it does not have to be emergency surgery. The just like, you know, many, many other analogies in life of, you know, studying for a final exam. Of course, it’s going to be horrific when you have to stay up all night and cram.

Brian Dukes: And ultimately the pain of probably not doing as well as you as you want. Now. Now you think about selling a business. And if you’re trying to to cram. If you’re trying to prepare with no time, invariably mistakes will be made. Money will be left on the table, other opportunities will be lost. And you have, you know, I’ll speak from personal experience. I regret some some bad final exam scores. It’s completely different to regrets like, oh my gosh, I left $1 million on the table because I just wasn’t prepared. And that’s a that’s a different process. So the idea of hey, we’re all busy as business owners, big or small, your your day is filled with life and work. Uh, adding another task to your to do list can feel really, really hard. Like, I don’t want to deal with this today, but if you can find a way to take on small tasks, work with advisors or partners or experienced founders that have gone through it to take on small tasks each day, each week, when it comes time to get to the big day, it’s not going to be nearly as painful as as it otherwise would have.

Trisha Stetzel: I love that preparedness and plan. Okay, before we go there though. I know there are people who already want to reach out and have a conversation with you. What is the best way to connect?

Brian Dukes: Uh, our our website is xyz.com. Um, I’m most active on LinkedIn. Um, look me up there. Uh, I post a lot of educational content around building and exiting. And my email address. Brian b r I a n at xyz.com. That’s great. Thank you. Great.

Trisha Stetzel: Yeah, absolutely. And if you guys are looking for him on LinkedIn, it’s Brian Dukes. D u d u k e. All right. I want to dive into the part that we’re both even more passionate about than the first part of our conversation, which is readiness. I want to talk about readiness. What does it really mean? And why do so many business owners avoid thinking about it until it’s too late?

Brian Dukes: Um, yeah, I’ve kind of I’ve kind of talked about it, uh, or a couple examples already. But really, the my my my core belief is that a we’re too busy. I’ll get to tomorrow and b I don’t know who to talk to or to trust. And if you add I’m busy, I don’t have time for it today. And I also don’t know who who’s the expert that I trust enough to talk about something so personal. Uh, yeah. Inherently it’s just going to get delayed. And I think there’s just this, this stigma that exists that we have to keep it so private and so confidential, and we’re not allowed to talk to anybody. And oh my gosh, if my clients hear that, I’m thinking about selling. It’s the end of the world. And although I agree there’s certain aspects of that that need to be kept private, I, I believe and this isn’t me even being self-serving, I believe that more CEOs at any stage of any size businesses should be surrounding themselves with people that have been through it before that, um, maybe they’re even an M&A advisor or banker. Um, people that understand what that process is going to look like and feel like and talk openly with their teams and their employees. Um, I’ve seen firsthand the experience of despite begging CEOs to bring their team into the mix, uh, when they don’t. And then potential buyers start knocking on the door. There’s conversations that need to be had. People in suits start showing up in the boardroom. Everybody. I’m sure you’ve seen it before.

Brian Dukes: It’s like the whole office shuts down. Everybody wants to know what’s happening. The rumor mill starts spiraling out of control. And again, it it’s it’s not just the chaos of the sale. You have to keep running your business during the process. And the more distraction and chaos beneath the water’s level that’s happening, the more likely it is disappointment is going to occur through it. So again, a bit of a broken record. Readiness is is something that we’re super, super, super passionate about and understanding whether your business is worth $10, 10 million, 10 billion at any stage. Understanding, um, what is a buyer going to look at with your business, and how are they going to evaluate it? And what are the things that you could do to better, um, prepare your business for that, that future exit, uh, address things that buyers are not, um, are, not are going to question or want to dig into, um, and getting really comfortable with, um, with answering detailed questions about your business that, that you not only can tell them the answer, but you have backup documentation to prove. I was on a short aside, I was on a call yesterday with a client and we’re going through a six month project, um, of preparation prior to exit. And, you know, they were kind of validating, like, hey, you know, I’m just I’m not sure exactly, you know, what are some of the first steps or some of the things that we’re going to go through here? And he said, because I don’t like, I don’t um, I can’t really tell you how I, how I price you know, I have, you know, one of my biggest clients, they come to me and I’m like making it up on the fly.

Brian Dukes: Well, today it’s this price or yesterday it’s that price or I’m just negotiating on the fly. Like, how could you possibly Brian, document what that’s like. And I’m like, well, first you’ve just told the story of why we have to go through this process. Because if you told a potential buyer that you just make up the price on the fly like that, that’s a bad that’s a bad conversation. Your books, your financials tell that story and it’s okay. Like, don’t be embarrassed. You you may not know what that strategy is. You may not be able to quote what you’ve done for the last five years, but the books do. And if we can build a financial model that shows the history of that client, of that industry, of kind of your pricing strategy over time, and you can answer it confidently and then show the details in a financial model. Suddenly there’s no questions like, the buyer may not agree with that strategy. They may not like that strategy. They may see huge opportunity in that strategy of like, oh my gosh, you’re leaving so much money on the table here. Uh, but there’s no question of I don’t understand what I’m looking at, uh, because the moment they don’t understand what they’re looking at, that leads to ten other questions. And then we just get into this death spiral.

Trisha Stetzel: Okay.

Brian Dukes: Sorry a lot there.

Trisha Stetzel: No, I know I think this is fantastic. I love the conversation that we’re having so far. Um, and I think I hear what you’re saying is that everyone will exit their business. Everyone will exit their business.

Brian Dukes: We will all exit our business at one point in our lives. Yes.

Trisha Stetzel: Yeah. Okay. So, uh, as you were talking through that last scenario, I was thinking about owner dependance, and I think that that’s a really big topic when we’re talking about exit strategy or preparedness or readiness. Can we talk a little bit more about how important it is that a business not be dependent on one person?

Brian Dukes: Sure. Yeah. Uh, and the answer can be different depending on how big your, your, your business is. One of the, the struggles that a lot of smaller businesses face is okay, great. I don’t want this business to be dependent on me, but I can’t afford to go hire a massive team to support me. And and so of course, if you’re a bigger business and you’re still dependent on the CEO, you have a little bit more flexibility to go, uh, either enable your, your, uh, your team, your, your executive team or the trusted folks around you start enabling them to make more decisions, to be more involved in the process, to document those processes, to have a voice. Uh, it’s always the, you know, a good test to, you know, hey, can you go on vacation for two weeks and not pick up the phone? Um. What happens? Um, it’s a good test. Um, but for a larger business, um, I wouldn’t say it’s not as complicated, but there’s more flexibility because it’s easier for you to go add to the team or supplement your role. Um, just through pure scale. When you’re a smaller business, you can’t just go hire three people to, uh, to manage your day or to do many of the tasks because the financials may not support it. And so our best guidance there is start with documentation to the example I just gave. That’s a that’s a I wouldn’t say a small business, but it’s not a huge business. It is very owner dependent. And so you can hear it in my story. Right. He’s he’s worried that this asset is unsellable because everything’s in his head. Well the answer isn’t to go hire three people. The answer is let’s dig in and understand what this business is all about.

Brian Dukes: It’s not just about documenting process. It’s about documenting process, understanding the business. How do you win today? How do you win the week? How do you win the month? And then starting to to understand what the real answer is to some of these questions that for the owner they’re very vague. But as I said before, the books tell the story like you can you can create the picture of what this business actually is or what it does or how it operates. And once you have that picture, you can even at a small business, you can either outsource, find small, uh, you know, from a financial perspective, bookkeepers that can help keep you on task and take over more of the billing and invoicing. You can you can bring on interns or virtual assistants or even, you know, AI in certain instances to take over some of the basic tasks, uh, of what you’re doing day to day and then allow you to do owner things like focus on the big ticket items. I don’t think it needs to be this super complicated, uh, situation of like, well, I’m, you know, I’m only a $2 million a year business. There’s no way I could hire three people. So I’m just. There’s nothing I can do. Like, it just is what it is. Um, I’m never going to be able to figure this out. And it’s overwhelming because they know how many things they do. Well, if you go through a process of documenting, working with advisors and operators that have done it before, you’d be surprised at how much efficiency that you can gain by knowing, organizing, and then finding small ways to outsource or supplement your time without having to go hire a huge team.

Trisha Stetzel: Yeah, you don’t have to do it alone, even if you are alone, right? I, I love what you said earlier about having people who have done it before you in the room. And I talk a lot about, um, who’s in your room? You need to have people who are bigger, better, faster, stronger than you in your room, always helping you get where you want to go. So you guys, I don’t care if you’re not even thinking about exit planning. I want you to do something today that’s going to get you where you need to be to exit your business later. So what piece of advice would you give to those who are listening, who haven’t even been thinking about exit planning, but heard you say, Brian, everyone will exit their business one way or another. What can they do today to just take that next right step to prepare for the inevitable?

Brian Dukes: I think the, um, the easiest suggestion that I give to any CEO or business owner is go find 2 to 4 hours of time without your cell phone. A weekend, a morning and evening. Just go find a block of time and have a notebook and let the body and the mind calm down. Some people enjoy having a glass of wine as they kind of relax and try to be really thoughtful about if you could design your business, your business’s exit in the next 5 to 10 years, what would that perfect world look like? And it’s not just I want $100 million in my bank account that’s, you know, that’s great. Everybody wants a little bit of money. This is what do I want for my people? Like, how do I put that that person that has helped me push this business forward. What is their ideal situation like? What am I trying to accomplish for them? Do they want a bigger role? Do they want, um, equity? Do they want to be, you know, part of this team long term if I, you know, trying to help them have enough experience to go, you know, build their next company. Um, who’s the ideal buyer? Right. Is it, is it, uh, somebody local in your market? That is going to is going to take care of the asset that you’ve built or is it, you know, a strategic, maybe even competitor, like, what would that feel like to have that conversation or a really big, you know, private equity, get some negative stigma sometime. But the idea of more of a financial buyer, somebody that’s, um, you know, they’re not going to be as focused on your people.

Brian Dukes: They’re buying you for more of a financial win for themselves. But long story short, sitting down and really trying to be thoughtful of designing, like, what is what do I want out of that exit in the future? And how do I feel about that exit? And what do I want to do in my in my life? And it’s one of those things could be I just want to run this business until I, I can’t run this business any longer, and that’s okay. But it also, even if that’s the case, it helps you think about and be honest with yourself of like what you’re trying to accomplish with this asset that you’re building and the life that you’re trying to design and the lives that you’re impacting with the employees that you that you have. To me, one of the one of the the the only things that are worse than not doing anything is trying to do something in regards to exit planning, but not knowing what you want as the end game. Um, it’s like any other analogy in life, you know, if you, if you start running down a road and you don’t know where you’re going, like, you might as well not run. Um, it’s I think it’s so important kind of the theme of some of our, some of the things we’ve already talked about of like really being thoughtful of the life that you’re trying to build and what you want to accomplish, and understanding that the thing that you’ve built is probably going to impact others. I had a CEO who we had done a really nice job, I think planning for the exit, who had been really thoughtful of putting, uh, his employees in great position.

Brian Dukes: A lot of people, you know, they made some life changing money. Um, as part of the acquisition. And he called me a couple weeks later and he said, we didn’t talk about it around the dinner table a whole lot during the process. But I told my kids over dinner last night that we sold the business, and the kids started crying. Um, because they had grown up knowing my dad and mom, you know, are the owners of this thing. And now my my, my dad doesn’t have a job. He’s out of work, right? As children, they don’t understand the implications. And it really struck me that, like building a business is is, you know, a community effort and, you know, being really thoughtful of like, what this means to your employees, to yourself, to the, you know, who’s the ideal buyer? Even your kids, I think I think it’s a really important thing now, functionally, um, a bit self-serving. You know, we always start our relationships with clients saying, understanding what your business is worth going through evaluation process, organizing your financials, and just getting a really high level understanding of what it is that you’re building towards is really important. Um, that’s our starting point of where we where we begin with every client and we think it’s it’s a great place to start. But, you know, I just I’d really encourage people to be really, uh, try to quiet it down and really be thoughtful about what that future looks like.

Trisha Stetzel: Yeah, I love that. Something that I’ve seen through our entire conversation today is the care that you have for the people that you’re working with. And I really feel like another special thing that you’re bringing to your clients is this idea of building a relationship. And I see that and I think it’s very thoughtful. So, yeah, thank you for for doing that. Because oftentimes when people think about exit or M&A or those words come out of anyone’s mouth, it sounds cold, Right. It doesn’t sound like a relationship or some place where someone really cares, and I see that coming from you. So thank you for bringing that to our conversation today. So I happen to hear from a little mouse that if folks are listening and they want to engage in a first step with you, that you might give them a special deal. I’m just saying. Um, would that be the case, Brian?

Brian Dukes: Yes, please. Uh, thank you for mentioning that. Um, and yes, for anybody listening, uh, please email me, uh, Brian, Brian at xyz.com. Uh, in the in the subject to put Houston Business Radio and happy to give you 20% off, $1,000 off our valuation and exit readiness process. Uh, it’s a four week process in which we just help you better understand, um, your business, help you get a little bit organized, give you a view of what buyers are going to look at, and you get to spend a little bit of time with myself and my team. And, you know, we’d love to be helpful, so please reach out.

Trisha Stetzel: Love that. Thank you Brian for that. I really appreciate it. And thank you so much for your time today. This has been an amazing conversation and I can’t wait to have a follow up. I think we should do this again in a few months.

Brian Dukes: Anytime. Thank you. Trisha.

Trisha Stetzel: Yeah, absolutely. All right guys, that’s all the time we have for today. If you found value in this conversation that Brian and I had today, please share it with a fellow entrepreneur, veteran or Houston leader ready to grow. And as always, be sure to rate and review the show. It helps us reach more bold business minds just like yours and your business. Your leadership and your legacy are built one intentional step at a time. So stay inspired, stay focused, and keep building the business and the life you deserve.