Ep. 9 Business Success Without Sacrificing Family with Mac Lackey
In this episode of the Legacy Branding Podcast, host Laura Beauparlant sits down with serial entrepreneur Mac Lackey, who has started, scaled, and sold six successful businesses.
Mac shares his journey of building ventures that attracted industry giants, and the lessons he learned from his impressive exits. As the founder of ExitDNA, Mac now mentors entrepreneurs on how to prepare their businesses for sale, emphasizing the importance of proactive planning and brand equity in driving valuation.
He also reflects on balancing personal priorities—like being present for his family—with entrepreneurial success and discusses how owning a 115-year-old Spanish soccer club ties into his vision of legacy.
Tune in to hear actionable advice on creating a sellable business, maintaining balance in your life, and leaving a meaningful impact.
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Mac Lackey is an American entrepreneur who has started, scaled, and sold six companies.
Mac and his companies have been featured on CNN, The Wall Street Journal, Fast Company, Business North Carolina, USA Today and The New York Times.
Notable ventures include KYCK (acquired by NBC Sports), Mountain Khakis (acquired by Remington), and InternetSoccer Network (acquired by a division of News Corp/Sky).
He additionally served as a member of the Board of Directors for Lending Tree (NASDAQ: TREE) for over six years and is an angel investor in over 50 companies.
Mac is currently focused on mentoring entrepreneurs via his proprietary platform, ExitDNA. Mac is also the proud owner of the 115-year-old Spanish soccer team, Algeciras CF.
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00:13 Welcome to the Legacy Branding Podcast
00:50 Introducing Mac Lackey: Serial Entrepreneur
01:41 Lessons from Six Exits
02:51 The Importance of Early Exit Preparation
03:56 Regrets and Reflections on Timing
06:27 The First Business and Unexpected Offers
09:13 The Existential Crisis Post-Exit
16:59 Balancing Business Success and Family Life
19:31 A Father's Commitment and Entrepreneurial Journey
20:12 Balancing Family and Business Success
20:59 Empowering Teams and Creating Boundaries
23:07 The Value of Designing a Sellable Business
24:32 Introduction to Exit DNA
24:54 The Birth of Exit DNA
30:51 The Importance of Brand and Intellectual Property
35:44 Defining Legacy and Personal Reflections
38:43 Connecting with Mac Lackey and Conclusion
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Mac Lackey: I was in my mid to late twenties, and I had an eight-figure exit. So I went from literally peanut butter and jelly sandwiches every night to checking off almost every financial goal and dream I had ever had.
Laura Beauparlant: Welcome to the Legacy Branding Podcast. I'm your host, Laura Beauparlant, here to guide you through the journey of selling your business, creating value, and building a personal brand that leaves a lasting impact. On the show, we'll explore real-life founder stories, expert insights, and actionable strategies to help you navigate the transition, avoid post-sale crises, and create your impact-driven legacy brand. Whether you're thinking of selling, building to sell, or already on the other side, this podcast is your go-to resource for making your next evolution your best one yet. Let's dive in. Today, I’m super excited to welcome Mac Lackey to the Legacy Branding Podcast. Mac is a serial entrepreneur who has started, scaled, and sold six successful businesses. His experience has been spotlighted in the Wall Street Journal, Fast Company, the New York Times, and many more. Beyond building and selling businesses, he’s served on the board of directors for LendingTree and invested in over 50 companies. Currently, Mac channels his experience into mentoring entrepreneurs through Exit DNA, where he helps founders create value and plan successful exits. He's also the proud owner of Algeciras CF, a 115-year-old Spanish soccer team. Welcome, Mac.
Mac Lackey: Thank you so much. Yeah, excited to be here.
Laura Beauparlant: Isn’t it interesting to hear back your bio when somebody reads it to you?
Mac Lackey: It sounds exhausting. Yeah.
Laura Beauparlant: And impressive. So now you’ve had six exits. That’s a lot—probably a lot more than the average person. What would be the most important lesson that you learned when it comes to building a business and having exit value in mind?
Mac Lackey: Yeah, it’s a really good question. Yeah, I feel very thankful I had six exits because I certainly made a lot of mistakes along the way. My first exit—really my first two—were amazing and life-changing in a lot of ways. I had two eight-figure exits in my twenties, so I got a very early start, but I also left millions of dollars on the table not knowing what I was doing. With the benefit of hindsight, I can look back and realize all the simple things I could have done or should have done that would really change those outcomes. Statistically speaking, only about 20 percent of entrepreneurs even trying to exit kind of get through the exit door. So, I guess one of the biggest things I would say is I learned the hard way and early that preparing for an exit, being proactive about it, and really optimizing your business so that it can be sold—that alone really changes the dynamic. Entrepreneurs typically wait until they need or want to sell. There's lots of reasons for that—it could be, they need the money, someone gets sick, they’re burned out, or they think the opportunity is great. Then they say, "Now I want to exit, and I’d like to do it in the next six months or 12 months." Although that can happen, it almost guarantees that you’re not going to be able to take advantage of so many things that you could have done. There are little changes in your business that compound into value over time. So, long answer to your question, but I’d say the biggest thing is to start early, prepare early, and to me that means at least two to three years before you’d like to close a deal. And we can talk about why that timing matters too, but that’s probably the minimum to really maximize value.
Laura Beauparlant: And I guess you’ve sold these six businesses. Would you say that you’ve had any regrets in selling any of those businesses, or are you happy with—like, you sold them, you’ve moved on—is there anything you would do differently?
Mac Lackey: Yeah, there are a lot of things that I, you know, probably would do differently if I could rewind all the way back. I don’t have a lot of regrets in terms of selling them. I think in every case it was the right decision to sell. I probably have a little bit of a bias towards selling early. You know, I think if I look back very critically and say, was the timing right? Some of my businesses I sold early, and maybe another year or two of building could have yielded a bigger exit, but I also know that I’m a big believer in mitigating risk. Despite the fact that most people would say, "Oh, he’s a crazy entrepreneur that spent his life building these high-growth companies," I am constantly thinking about optimizing for timing. When you get to my age, there used to be a saying that a "Black Swan" event could just change your business overnight. I feel like I had a Black Swan event every other year of my working life, whether it was the dot-com bubble burst, financial crisis, real estate crisis, global pandemic, recession—you’re eventually like, "Huh? I just don’t know what the future holds." So I made the decision again and again—when I got to a number that made sense to me, I would exit. So, I probably would think about some of those things, but I have the benefit of hindsight now. It’s easy to look at someone like me and say, "Oh, he’s a flipper, he builds companies just to sell them." That really isn’t the case. Interestingly, almost every one of my companies, I started either to solve a problem that I saw in the world or something I was super passionate about. A lot of those companies I would have happily run for 20 years. I loved what we were doing. I love what we were building, but I was very opportunistic when the right offer or opportunity came along to take chips off the table or to put our company in the hands of someone or a group that could really take it to the next level and create a legacy or something else that we cared about. So, yeah, I’m fortunate to have the benefit of hindsight and I probably would do a few things differently, but overall, very happy that I sold as many times as I did and most of those feel like, you know, good decisions.
Laura Beauparlant: Would you say that you started each of those businesses with the plan to sell it?
Mac Lackey: I would say after the first one, that was the only one. Where, and to step back for a moment, I went from playing soccer my whole life—focused on playing soccer, that’s really all I cared about growing up and through college. And I played briefly professionally after. So I went from playing soccer to what am I going to do next with my life. I started my first business in the first quarter of 1995. We launched an internet company right after Netscape launched the commercial web browser. We were very early in what people now call web one. But that was a garage startup. It was a true struggle. I just didn’t have any money. My wife was working multiple jobs so we could pay our bills to try to get this business going. There was not a thought in the world about ever selling a business. We were working hard, just got to the point where we were starting to make a little bit of money after years of struggle. Because the space was so early and we really convicted, all the smart people around me, even my mentors were saying, "Oh, the internet’s a fad. Nobody’s going to use credit cards." Despite what we were hearing, we were so convicted that the internet was going to change everything. We just wanted to be all in. And so literally up until the moment that we started getting offers on the business—we were just heads down thinking about building and every dollar we made, we tried to hire someone, a new engineer, someone really smart. It really surprised us when we started getting offers because that wasn’t the plan. We sold into a roll-up. They bought 20-something companies, put them together, and took it public. And, again, I was in my mid to late twenties and I had an eight-figure exit. So I went from literally peanut butter and jelly sandwiches every night to checking off almost every financial goal and dream I had ever had. In that moment, it was such an eye-opener that if you work hard and you can create that much value in a short period of time, it should be intentional. That was my shift. For my next business, I decided to build something I was super passionate about, but from day one, the first eight-page presentation we did, one of the slides was: who is going to want to buy this business? It was just part of the DNA that we had from that point on: We don’t want to be forced to sell it; we don’t want to have to sell it. But we always want the option where someone’s going to offer us a lot of money and give us the chance to say yes or no. That was our thinking. So it shifted after that first one. Thereafter, every business, it was always on my mind.
Laura Beauparlant: I love that. I talk with a lot of entrepreneurs who have sold or who are thinking of selling. I talk about this existential crisis that often happens when people sell their businesses because their identity is so wrapped up in the business. Who are they if they are not the founder of this business? What will they do next? It’s really because they’re so deeply invested and emotionally tied to the business that it feels like an extension of them. And it’s like you’ve cut off a limb. And so by being intentional right from the get-go and thinking the plan is to sell this, it doesn’t mean you’re not putting your heart and soul into the business. I think it helps you stay a little bit less deeply intertwined and embedded with the business so that when you do sell, your whole identity is not being sold with it or being cut off from that business.
Mac Lackey: I could not agree more. One of the interesting things now that I’ve shifted primarily from building and selling my own companies to advising and mentoring other entrepreneurs on the journey is one of the biggest predictors of whether a deal will actually happen or close or not is if the founder or primary entrepreneur knows what they’re going to do next. If they don’t have some clarity and confidence on what post-exit life looks like and hopefully be excited about it, there’s a little bit of a tendency to even self-sabotage. Yeah, the identity is so tied to it. What are people going to think? Who is Mac without this business? And I think a lot of entrepreneurs struggle with it. So we talk a lot about that, which is, let’s get clear on what post-exit life looks like. Do you go with the buyer or not? What does that look like? What do you want your role and participation to be? What’s the transition plan? What’s the legacy? Working through some of that, which is almost like personal psychology, is critical. I’ve witnessed a lot, even business partners of mine who’ve struggled more than I think I have post-exit because I was already almost always excited about the next thing. I was going to start, already had an idea—I was already slowly getting it going before we had sold a business. There are two types of entrepreneurs: one big category, where the business is my baby, it is my identity, I’ve poured everything into it. And then there’s the other category, which I think I’m more closely aligned with, which is I just love starting things, building things, and impacting the world. In order to do that, I’ve always had five things I’d like to start and three people I’m excited to work with, so it’s never been so tied to just one business. Even though I’ve loved the business, I’ve never been afraid to let it go or put it in someone else’s hands.
Laura Beauparlant: Yeah, and I think that’s why we’ve really focused so heavily on working with founders who are thinking about exiting. While we can help with positioning the brand to exit and cleaning it up, to me, it’s actually working with the founder on their personal brand and separating them from it. Because even when we start working together, they start sharing things, and I’m like, "That’s the business. That’s not you." And finding a way so that there’s going to be overlap—they will work together, but they should be going in tandem, not so deeply intertwined, especially if you’re exiting. I’ve seen that is really an area that is so needed because it’s not often thought about until after they’ve sold. And then we talk with people and they’re like, "I wish I met you years ago before the existential crisis after selling."
Mac Lackey: Very true. Very true. Yeah. If there has been a long duration, if someone’s been running a business for a long time and they found themselves in the typical entrepreneurial grind, which I’m a big fan of getting out of, but if they’re working 40-plus hour weeks or, God forbid, 80-plus hour weeks, the other thing is people imagine, "I’ll make a lot of money. I will take a break. I will play golf. I will go lay on the beach." Honestly, that literally never lasts for more than about a week. I’ve told myself the same things. I literally was closing the deal for my second company and walked from the attorney’s office to a mall to buy a pair of running shoes. And I was like, "All right, tomorrow the whole new plan starts. I’m going to do all these things." After a couple of days, my entrepreneurial mind would just not allow me to stop. I just wanted to keep building things. I had no pressure. I had no financial need to do it. It was just like, "I’m excited. I don’t want to sit around. I don’t want to play golf. I don’t like golf." It’s funny. I try to tell a lot of entrepreneurs on the journey, "You’re going to look and think and feel a lot like you do today, post-exit." Don’t assume that a drink with an umbrella in Fiji is a long-term plan. It might be a great celebration for a week, but you need to have purpose and legacy and all those things on your mind just like you do today, post-exit. There might be another vehicle you use to deliver that; it may not be the same business, but you still need to be thinking the same.
Laura Beauparlant: Yeah. To me, what that does is it means because you don’t necessarily need the money, you can do anything, which can be scary because then you’re like, "But what is that?" Because there isn’t that pressure. The beauty is that you can do anything. Entrepreneurs are wired to create impact and to work and do amazing things. So it’s figuring out what that next thing is, and it’s a lot easier if you already have a bit of a plan before you’ve exited.
Mac Lackey: Yeah, no, you’re exactly right. I think the overall message I think you and I are both very convicted around is just, being proactive, asking yourself, asking people around you, your mentors, advisors—just doing the work in advance is really smart. You almost always identify things that you need to work through, whether it’s a personal process or identifying things, which I see literally every day of my life, that are risks you can mitigate that may hurt your deal, may affect your ability to leave. That’s the other thing. A lot of people sell thinking, "I’m done with this chapter." Sometimes people are burned out or they’re really, truly wanting to move on, and they can’t because their business is so reliant on them. I always tell entrepreneurs, "No one wants to buy a business where the founder or the key entrepreneur is in the critical path—every decision and key call and how the business works and key meetings." The more you extract yourself from that, your personal freedom goes up, which again, I think is really important and valuable in life. But the other is you’re building a more valuable business. So you have the option when someone comes in to buy it to say, "You know what? You don’t need me. I can prove to you the business runs by itself. It’s automated. It has amazing talent. We have great SOPs." Or, if you want to continue with that business, it’s much easier to argue your role as more a consultant, an advisor, a board member—not a five-year employment agreement to help a transition.
Laura Beauparlant: Yeah, and that’s not what people want, but if you’re too intertwined with the business, then ultimately you will need to go with the business when it’s sold for a period of time. Most entrepreneurs don’t like to be employees or make terrible employees.
Mac Lackey: Very true. I’m not employable.
Laura Beauparlant: No, I know. My husband and I have that conversation all the time. Like, we are not employable. Something that I find really fascinating about you, Mac, is, you know, I think there’s this story, there's this narrative that you can't have it all—that you can’t run these wildly successful businesses and make a lot of money and have family time, family life, happy marriage, etc. You have found a formula to have both. I think that’s such a beautiful message because it is something that you hear all the time. It’s like, well, you can’t have money and love, and if you have one, you can’t have the other. You’re happily married. You’ve spent lots of time with your kids as they were growing up. Yet you also built and sold six businesses. Can you just talk a little bit about what that took?
Mac Lackey: Yeah, actually, I really appreciate you asking. A lot of times I try to be actionable in having these conversations because I want to arm entrepreneurs with exit preparation and thinking. One of the most important things in the world to me is what you just said. The very short backstory is I sold my second company in July of 2000. Again, I hadn’t turned 30 years old yet. I’d had a lot of "success" on paper. My first daughter was due to be born in August of 2000. And candidly, I went into a depression. The reason for that depression is a lot of what we’ve already been talking about, which is so much of my identity was not tied to a specific business. But I was all over the media. I had been quite successful at an early age and everyone was in my ear talking about these internet kids that are changing the world and building amazing businesses and flying all over the world, and that’s who I thought I was. Yet I was about to have a little girl, and all I could think about was, I want to be the kind of dad who coaches the soccer team, is at every school play, carves the pumpkins on Halloween, and is home for dinner every night at five o’clock. That was how I was looking at the future. I got depressed because everyone around me kept saying, "You’re really fortunate, Mac. You’ve made some money. So you could just take a sabbatical and enjoy time with