Marc Weiss exited Management One, stepped away, and then returned with a fundamentally different perspective on leadership. In this episode, he shares what distance and experience taught him about governance, accountability, and the founder habits that quietly limit enterprise value. The conversation centers on what he is doing differently the second time and how returning changed the way he builds and leads.
What you’ll get from this session:
- What changes in a founder after experiencing an exit
- The leadership habits that do not scale, even if they once worked
- How structured accountability reshapes strategic thinking
- What Marc is doing differently now compared to his first chapter
Why it matters:
- Many founders underestimate how much they are the constraint
- Exit experience sharpens judgment about governance and discipline
- Returning leaders must evolve or risk recreating old bottlenecks
- Second chapters often reveal what truly drives enterprise value
TRANSCRIPT
Greg Alexander: Hey everybody, this is Greg Alexander. You’re listening to the Pro Serv Podcast, brought to you by Collective 54. If you’re new to this show, we are dedicated to founders of boutique professional services firms. So, if you’re in the business of expertise, you market, sell, and deliver expertise for a living, this is for you. We aim to do three things in this show. Help you make more money, make scaling easier, and make exit… make an exit achievable. And this week, we’re gonna talk about the Boomerang founder. What is the Boomerang founder? This is a founder. Who has sold his firm. And after some time, Returns to the firm. For a variety of different reasons. This is not a topic we have covered before. But in my preparation for my interview of this week’s guest. I have learned that this is happening more than we realize. So I wanted to unpack it with a real example. And my goal in doing that is to share with others who have sold their firm, or are thinking about selling their firm. How this might happen to them, and if it does happen to them. how to turn it into a positive and not a negative. So that’s what I’m gonna try to do today. And joining me is a longtime member of Collective 54, who is a recent Boomerang founder. His name is Mark Weiss. And, I’m going to interview Mark and hear a little bit about his story, but Mark, for those that either don’t know you or it’s been a while, would you please reintroduce yourself to the community?
Marc Weiss: Well, hi everybody. My name is Marc Weiss. I owned a company called Management One. I sold it in October of 2022 to a… and I think I did a podcast on this, too, on… to a search firm. And that’s a group of investors that fund a person to be a CEO and run the business. And that’s who I sold it to. And then, Management One provides inventory planning to independent specialty retailers across North America. We have a few clients in some other countries as well. ideal customer profile or, you know, mom-and-pop businesses that do a million to $3 million, but we do have clients that are, you know, pro sports teams and most of the major college bookstores, so we do, you know, I’d say from a half a million to 100 million in revenue per client.
Greg Alexander: Okay. So, Mark, in October of 2022, After running your firm for 35 years. At the ripe old age of 70 years old, You sell it. And you are rewarded for your life’s work, and you make enough money… That you and your wife ride off into the sunset. This was very typical. grandparents’ European vacations. In fact, if I remember correctly, you were actually looking at buying a house in Tuscany.
Marc Weiss: Yep. So… How old is it there?
Greg Alexander: Yeah, and then… 2 or 3 years passes, and you come back to the firm. So, before I get into my questions, we just need to hear How that happened.
Marc Weiss: Oh, I kind of stayed connected with the company. I mean, I was doing work for them. I was getting a lot of blowback about things that weren’t going well, so it wasn’t a surprise. One of the board members had reached out to me six months prior to ask me what I thought of how things were going, and I gave them my assessment then, so it wasn’t a complete surprise. And so, I mean, I kind of knew something was happening.
Greg Alexander: Yep. Now… as I mentioned, you were 70 years old when you sold your firm, you’re wealthy, you have your health, and you and your wife are enjoying life, okay? What was it about retirement? that… Didn’t take with you. And how did that lead you to wanting to get back into the world of being an entrepreneur?
Marc Weiss: Yeah, so I think the beautiful thing about retiring is I realized that I couldn’t. You know, that my mind, you know, they always ask that question, what keeps you up in the middle of the night? And for me, it was just… Ideas, you know, constantly, thinking about things that, you know, when you’re running the business, you know, there’s… you have limitations on what you can get accomplished. And once you’ve sold the business, all the things that you dreamed that you wanted to do are right in front of you to do, and they don’t go away once you sell the business, right? They actually become more front and center. So I played around with a couple different ideas. I actually worked hard to build this idea of inventory finance for retailers. I actually did a lot of research on it. Learned a lot about it, and actually found a good partner for it. And then, actually, I was on a vacation in Spain when my partner called and said, interest rates are going up, we think it’s too risky, we don’t want to do it, and I was heartbroken. So then I started to think about some other things I wanted to build, so I started to build something called a peer-to-peer network. And benchmarking, and I always felt there was this opportunity to take what Collective 54 does for B2B businesses and provide that same… a similar format for retailers, so I started to work on building that out.
Greg Alexander: Now.
Marc Weiss: I guess the answer to the question is, you just… I could… I knew in my heart that I couldn’t… not do something. I needed to contribute. I needed to be in the game. I continued to speak around the country. I actually took on a gig to do benchmarking for a pretty big trade association. We did that. And so, I don’t know, I just was getting back into it, so it was just… You know? Yeah. Hard to look up.
Greg Alexander: So, you know, you worked all this time, you retired, retirement wasn’t what you wanted to be. It helped you learn who you were, which is you’re an entrepreneur. You want to be in the game around young people, working on ideas, you know, having a sense of purpose. So, when I was in your shoes, and I sold my firm, people told me that was gonna happen to me. And I told them they were crazy, because I had been doing it for 25 years, not 35 years, but I was really tired. And I needed to, you know, enjoy myself and not work as hard. But the same thing happened to me. I spent 2 years off, and then I went right back into business and started a new firm. When I tell this story, and when people listen to your podcast. To me or you 20 years ago, they say the same thing, you’re crazy. You’re telling me I can’t retire? Watch me. So what didn’t we know, then, that we now know, that we can share with listeners? So that they don’t have to go through this mistake that you and I went through.
Marc Weiss: Yeah, that’s a great question. I sometimes think you almost have to go through it to learn it yourself, right? But if you’re the kind of person that just has endless ideas, but you’ve learned to be successful because you’ve learned to focus, I mean, that’s what it, you know, what do entrepreneurs do who are super successful? They’re able to harness all that energy and all those ideas, and they’re able to focus and make it work, and I think that’s one of the things
Marc Weiss: That I love about Collective 54. I’ve got 3 members of my team now who we just joined Collective 54 and went through the onboarding process because they need focus. So, I think that, you know, to learn that lesson is just be honest with yourself, right? Take some time off to learn who you are and what you want to be, to what you, you know, how you think about things. But..retiring, like, I’m older than, you know, I’m like 73 now, and all of my friends are retired. They play pickleball, and they travel, and they do all kinds of fun things. They all think I’m nuts, but they weren’t entrepreneurs, right? I mean, they didn’t have their own business. They were doctors, lawyers, or… they had enough of all that. They weren’t builders. And if you’re a builder, and you see yourself as a builder, I guarantee you. I’m gonna be… I think, Greg, will you be 99% sure you will not retire. I also got to be friends with somebody that I work with in a non-profit who’s 82, and he… we went to lunch after I retired, and he said, don’t ever quit working. It’ll be the worst thing in the world for you, because that’s not what you’re built to do, you’re built to build. And it was true.
Greg Alexander: Yeah. You know, in preparation for this interview, I was… I was fascinated by your story, because we have gotten to know each other, and, you know, and I was… following you and your personal pursuits, and was so happy that you were so happy. And when I… when you came back, my first instinct was, oh no, like, something must have went wrong, like, what happened? And then I had a conversation with you, and it was just the opposite. Like, this was a really good thing, not a bad thing. It made you happy, not sad. So I started reading on this subject, and I read a whole bunch of things, and I learned an interesting stat. And that is, sellers regret. defined as people who sell their businesses and regret selling them. It’s 50%.
Marc Weiss: Wow.
Greg Alexander: and the small business. Did you have regrets selling the business?
Marc Weiss: No. No, I don’t think I had any regret. I actually wanted the business. I… I left the business thinking that I wasn’t… that somebody younger, better, with passion would be able to scale it better than I could. And I found out that I know how to scale things, but I… at the time, I really wanted to let go, and maybe build… and if I wanted to get back to work, start another business. I mean, I had the financial wherewithal to to retire and live the life I wanted to live, and yet if I wanted to invest money and build another business, I had that opportunity, too. So, I think I was happy that I’d had no regrets. I was glad that all the work that I had put in, I really got a, you know, it was a good… it was a good sale for me. So, and I didn’t have, like some other people who sell their businesses, you know, it’s on earnouts, and I didn’t have that, so I was in a really good position. So I had no regrets about the business. Did I miss it? Did I miss the people? Yeah, but, you know, I don’t feel like I had any regrets. Okay. I knew that I wanted to do something else pretty quick. I knew when I took… I took our family to Costa Rica, and I knew after being in Costa Rica for 2 weeks doing nothing that, I was gonna… I was… I was antsy already. It didn’t take long.
Greg Alexander: Now, you’ve been married a long time.
Marc Weiss: Yeah.
Greg Alexander: Are you… 49 years, which, congratulations. When you told your wife That you were going back to work. Was she happy that you were gonna get out of the house and do something, or was she upset with you that you were going back to work?
Marc Weiss: She just said, as long as I don’t have to go back to work with you, do whatever.
Greg Alexander: That’s a good answer.
Marc Weiss: And she also, we’ve got, you know, we’ve got 5 grandkids that are between the ages of 5 and 13, and she… I wanted to move to Italy for at least half the year, and then travel around the other parts, and she was willing to do that. I mean, we both loved… we both love Europe, but when she… when we… when I put it… when I wrote the realtor and said, I’m going back to work, I don’t… I can’t move, she was happy.
Greg Alexander: Yeah, okay. Alright, so in my research on the Boomerang CEO, I learned that there were 3 types. I’m gonna go through those 3 types, I want you to give me your opinion of each, and I want you to tell me which one best applies to your situation.
Marc Weiss: Okay.
Greg Alexander: So the first type is called the Rescue Mission. And the definition of the rescue mission is that, and this is the most common reason for boomerang CEOs, and it’s that the new owners, particularly institutional investors, which was the case in your world, struggle to manage the company’s culture. And that leads to declining revenue and declining profits. And then they ask the founder to step back in to save it. Is that what happened in your business?
Marc Weiss: Yes.
Greg Alexander: Okay, so what happened? I mean, as professionally as you can. Why didn’t it work when your business was in the hands of somebody else?
Marc Weiss: Yeah, so, it’s really painful because, one of the key investors who, you know, so our business was sold two investors, plus it was some debt, and, the debt holder said to the new CEO, this is one of the most operationally efficient and, and, businesses we’ve ever bought, so don’t screw it up. Those weren’t his words, he used the four-letter word. But for the nature of the podcast, I won’t use it. And I think he destroyed… the culture was destroyed, and the vision, the strategy was just… nuts. It was, they lost, revenue dropped, well, what happened was, when he left things alone, the business actually continued to grow. We were growing at, almost 30% per year, so in the first year and a half, the business really grew. When he started to implement his own strategy, it dropped by 40%. And he continued to spend, and continued to, you know, chase shiny objects, and try to deflect and do other things, and the more he worked hard to try to fix it, the worse it got, because he really didn’t he didn’t put a strategy in place that made any sense, and also hired the wrong people. So, if you don’t have the right people, you know, a lot of you are EOS companies, right person, right, you know, seat. wrong person, right seat, right person, wrong seat, wrong person, wrong seat. When that happens, the whole thing goes to hell in a handbasket. Yeah. And none of the teams were talking to each other anymore, and people were just protecting themselves, and it was… it was awful. So the first six months were just really about putting a tourniquet on it.
Greg Alexander: Yep. So the lesson for members that are listening to this is that if you sell your business. And you care about your employees and your clients that are going to continue to do business with the firm long after you’re gone. You gotta make sure that the person that’s taking over the business doesn’t make this mistake. Unfortunately, it’s hardwired into human DNA that the new CEO feels the need to put his or her fingerprints all over the business, sometimes making change just for change’s sake. They don’t want to just steward the existing business, they want to change it somehow. And when they change it, they often screw it up, and that sounds like that’s what happened here.
Marc Weiss: Yeah, I mean, I think it was just a general screw-up, and sold the board a bunch of math that didn’t even make any sense. So, I mean, he made it sound good. I would say that, When you… go in and deconstruct what’s working. You know, it’s one thing to build on what’s working and make it better, which is what I was hoping for. It’s another thing to deconstruct it and try to rebuild it differently without any pragmatic solutions to make that happen, or logic, in my mind, behind it. So when you think you have the right person. So, we have an annual meeting every year where we bring all of our affiliates and a lot of our partners in. I brought this person out just to have them be vetted. This was in April of 2022. We didn’t close till October. My lawyers told me I was out of my mind. You don’t have a deal, don’t bring somebody in. There’s too much at risk. If the word gets out that you’re gonna sell and it falls through. you know, you’re gonna have a cleanup mess. The cleanup mess I had was much worse, but the point is, is that even though I tried to vet him. And by the way, he sold himself beautifully. I mean, people liked him, they… you know, I thought I was making a great decision, offered to stay on and help. I was told that the transition plan we put together was an excellent transition plan, but in spite of all that. that, you know, when they start thinking on… when they don’t… I don’t know, maybe, Greg, sometimes I think Builders build a business and have a vision for what they want, and you take it as far as you can, but that doesn’t mean your vision isn’t even greater than what you initially thought. So when somebody else comes in and that vision doesn’t match what you’re doing, all kinds of bad things happen.
Greg Alexander: Dude.
Greg Alexander: Okay, the second type of boomerang CEO situation is called the arbitrage play. And this is where founders often buy back their companies for significantly less than they sold them for. So, for example, a founder might sell for $20 million and buy it back 2 years later for $6 million after the buyer fails to scale it. That could be very lucrative. Did you pull off the arbitrage play?
Marc Weiss: No, in spite of your, you’re really pushing me to do it, it just didn’t… it didn’t… it wasn’t who I am, so I… I guess I could have pushed for it, it might have been financially better. I didn’t do this it wasn’t a money play, right?
Greg Alexander: Yeah.
Marc Weiss: I’ve got a pretty good package that I’m putting together for myself, but it wasn’t about the money, it was about, you know. you know, saving the business. I spent 35 years, 40 years really building. And then the people part of it, and then, obviously, I had a vision for what we could do with it. So, with AI today, what we’re doing today… there were actually some things that were going on within the company that were really gems. I just had to find them, and once I found them, we’re just polishing them and making them great. So I was not the arbitrage guy.
Greg Alexander: Alright, let’s go to the…
Marc Weiss: By the way, if I was 20 years younger, maybe I would have been, but it wasn’t about the money for me at this point.
Greg Alexander: Yep.
Greg Alexander: Okay, let’s talk about the third and final Classification of the Boomerang founder. Loss of identity, and this is defined as… Many founders realized post-sale that their personal identity was more tied to the business than they thought. If the buyer decides to divest the quote-unquote non-core asset, the original owner is often the first person that they call. So, did you have a loss of identity?
Marc Weiss: No, I think I was beyond that. I don’t think it was loss of identity, and I’ve really done a lot of soul-searching on this. I didn’t come back for the ego. As a matter of fact, I think I’m a way better leader and boss today than I was before. As a matter of fact, some of the people that are still there, that are still with the company, have mentioned that to me, so I don’t think it was about ego or identity. I felt like I felt very good about what I… did in my life. I think the identity is more tied up in being there to contribute and be a part of something. That’s what I miss. But I did need the validation that the business gave me to be who I am.
Greg Alexander: Okay. So, you mentioned that you were 73 years old. I hope you live to 173, but the chances of that are pretty small. So, what is the finish line for you now, now that you’re back?
Marc Weiss: So the finish line for me is, you know, we’ll have another liquidity event, so it’s putting things in place so when that happens, We have the right people in place internally to grow and lead the company and look for different buyers, who are… who have already started that, that path, that research, to find companies that keep other… keep the company because they have a great management team. So that would be my goal, is… is to do that and turn it over. Stay on as maybe an executive CEO or something like that. I’ve got another idea for another layer on the business. If our business plan works this year, I’ve got an idea for next year that’s big and bold. So if I’m successful, then I know I’ll get the funding to do that.
Greg Alexander: So my last question for you would be this. So eventually, you’re gonna hand it over to somebody.
Marc Weiss: Right.
Greg Alexander: Last time you handed it over to somebody, it didn’t work out so well.
Marc Weiss: Yeah, well, this is somebody that’s internal. I’m putting the team together to be able to do that.
Greg Alexander: You’re gonna do it internally?
Marc Weiss: Yes.
Greg Alexander: Yeah. There’s a lesson in that, and I’ve seen this over and over again. In professional services firms. Particularly boutiques, small firms. We are a collection of people. And therefore, usually, because of culture. Internal succession looks a lot better than external succession. So, if you can, listeners, when you’re getting ready to turn your baby over, try to hand it to somebody who is inside the firm. The odds of success there are much greater. Would you agree with that, Mark?
Marc Weiss: 100%. I mean, people who get your culture, who live it, who believe it, who, are champions of it, and, you know, hold you accountable to it, are the people you want to lead your company.
Greg Alexander: Yep.
Greg Alexander: All right, well, very good, so we’ll save the rest for the private member Q&A, but Let me be the first to say, welcome back.
Marc Weiss: Thanks so much, Greg. Thanks for having me. Anybody that has any questions, you know, about anything, feel free to reach out. I’m happy to talk to anybody.
Greg Alexander: All right, sounds great, so I’ll leave the audience with this. If you’re a member of Collective 54, and you’re curious to learn more about life post-exit, and how you may or may not be a Boomerang CEO, please look for the meeting invitation, and we’ll have a private member Q&A session with Mark. If you’re not a member, and after listening to this, you’d like to become one, go to Collective54.com, fill out an application, and we’ll get in contact with you. But until next time, I thank you for your attention today, and I wish you the best of luck as you try to grow, scale, and someday exit your firm.