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A
When you got to the top of the mountain, you sold your business, you rang the bell, you achieved this thing you set out to do that you thought was going to fill you up, fill all the holes. It doesn't fill the holes.
B
Hello, everyone. My name is Rob Dube, and I am here with. What's your name again? Gina Wickman. Gina Wickman. Gino Wickman. How you doing?
A
Great. How are you, my friend?
B
I'm good. So our producer Rob came up with a great topic for today. I think it makes a lot of sense for where a lot of businesses are these days, where a lot of driven people's minds are. So we call it beyond the Exit. What happens to you when you sell or exit your business? And so what happened was Rob and I were on a call with the Exit Planning Institute, and they shared with us that a large number of entrepreneurs and business owners are entering into a time where they will be at an age where they will have to sell or exit their company. And this is going to happen in record numbers. So it creates an interesting time for driven people to really reflect. So, you know, exiting a business isn't all it seems on the surface, you know, meaning there's a financial piece to it, and a lot of people, I think, think about that aspect to it. But you and I have experienced that part firsthand. And there's more to it, though. There's like an emotional part to it that things are coming up, like identity, your purpose, and what comes after all this. Like, you been running a company day to day for years, and now it's not there. And I hear all too often, you know, golf gets boring pretty quick if you're a golfer, which I'm not. But I also want to talk, Gino, just to get your wheels turning, about these driven leaders who've been alongside the founder, building and running the business with that person each and every day, just grinding it out. And their lives are deeply impacted by this as well. So this is more than just a business event. And if you do it consciously, it's a real chance for you to shine in a whole new way. So what's coming up for you, Gino?
A
Hmm, Lots of stuff. First of all, golf never gets boring, so shame on you. I'm gonna bounce around a little bit, but I hope it'll set a little bit of stage or prompt some thoughts for you, because you and I have both sold businesses, so we're speaking from experience on this. And, you know, the first thing that always comes to mind whenever I think of a business owner Selling their business or I'm talking to somebody about it. It's the depression that I see almost every single time a business owner sells their business. And what's happened is they have sold their identity, and so their identity has been ripped from them. And they do go into a deep depression. And I've seen it now more times than I can count. And so knowing that, I think is like the first step, because I am fortunate enough to have had experienced it so many times with clients, I was able to head it off at the past for me, and that's the point here, is you can head the depression off. And the way that you do that is you sell. Well, in other words, you know what's going to happen after the sale. You decide one of two things. Are you going to stay involved in the business or are you going to move on? That's really vital. You have to decide if you're going to stay in that business. You know, are you employable, Are you ready to work for somebody? Because that's the reality of what's going to be. Or do you want to move on and ride off into the sunset? I chose to move on and ride off into the sunset. I did not want to have any involvement in that business, and I didn't the day after sale. So those are very important things because if you're going to move on, you've got to put all the right pieces in place, the team in place, so that you can move on. Most owners are stuck in their business because they have no one else to replace them. And so they're. If they sell, they're stuck being in the business for 1, 2, 3, 5 years on contracts that they don't enjoy, want or love. So I'll start there, see what that prompts for you. And then I'll just kind of work down my list here with some.
B
Two things are coming up for me. First, you know I didn't sell. Well, I don't believe so I want to share that experience. I was 32 years old. We got a nice offer, my business partner and I, and so we went down the road. We ended up selling it, but we agreed to work for them for three years. I didn't give enough thought to the idea that I am unemployable. I thought I could work through this. I get along with people, et cetera. But it was a public company, huge company, and I was like a fish out of water. It made no sense. I knew right away. I was like, this is a disaster. And I knew I had three Years ahead of me of this. So that was painful. The other thing was it was like, okay, once I realized that, then it was like, well, now what am I going to do when this three years is up? How am I going to make a living? I mean, I didn't make enough money to retire. So what's going to happen here now? And so no forethought there and then, you know, as far as like celebrating, I always had this idea. Joel, my business partner, you know, we would sell, we'd have this big celebration. So what we ended up doing is the day we closed, we signed the paper because there was no electronic documents back then. And we went to a restaurant to celebrate. Joel was sick and we were sitting there and it was raining, it was freezing out. And we were both just like. It was so anti climactic I can't even tell you. It was like, I don't know, it was perfect for us. So, you know, I wanted to share that because I didn't feel like I gave enough thought to it. And this is the part I really want to hear from you on is the team. What about the impact on the team? We put. We took virtually no consideration into that. We thought they'll still have their jobs. That was important to us and hopefully some opportunity to grow with this larger company. But how would this impact them emotionally? Totally did not think about that. And when we shared with them the news, they were not happy. So what comes up for you?
A
Yeah, so I'm gonn hit a couple things before we get to the team because you prompted a few other thoughts that I want to make sure are clear. First of all, I did a full riff episode on Selling well. Okay. And so I want to be careful not to repeat a lot of that. So please go back and listen to that episode. Very robust. And it gets into specifically what I did and some of the things we'll touch on. And then the other thing I always recommend is a book called Finish Big by Bo Burlingham that is just a great how to manual and how to finish big when selling your business. But with that I just want to hit on a couple things there. You know, just make sure you know your purpose after the sale. And again, that purpose might be something else outside of the business. You're going to move on right into the sunset or stay within the business. Know why you're selling, make sure that that is crystal clear. And then, you know, you called this beyond the exit. I didn't know where you were going to go. I never do with these Episodes. But, you know, I want to make sure that we're also addressing when I talk about the depression. The depression is the identity loss. That's not the other thing that happens, that when you got to the top of the mountain, you sold your business, you rang the bell, you achieved this thing you set out to do that you thought was going to fill you up, fill all the holes. It doesn't fill the holes. So you're, you're typically, if you're the typical business owner, you are going to feel empty. It's not going to be the satisfaction that you thought because there's more going on inside of you. So when I said depression, that's the depression of losing your identity. This, what I'm talking about now is the emptiness of getting to the top of the mountain and realizing that did not. You've been climbing this mountain for 5, 10, 20 years, and you realize that it doesn't fill this void you've been trying to fill as you've climbed that mountain. With all that said, I'll now move into leaders. And one of the things I share every time I talk about selling is I took an approach that most don't. So most experts, advisors, will tell you to never do this. I didn't care, and I did it. And so the day I decided to sell, I told everyone in my company. So I told you told them eight months before the business sold. So as I started the process, I stood in front of all of our people. At the time, there were probably, I think 150. And, you know, I said, I decided to sell the company. I gave the eight reasons why. And so I was very thoughtful. And that's what I'm urging is that you be thoughtful. Now you have to be the judge and jury as to how healthy your organization is. We had a very healthy organization. I am a very open and honest person. We are very comfortable with conflict. And so I was comfortable ripping that band aid off. Because for me, it is less painful to me to deal with all the employee issues and team issues around it leading up to the closing than surprising them like you did with your employees, Rob. And dealing with the hurt of that. I feel the pain of that after the sale is a lot less painful than the pain of just dealing with all of that. And now you're talking about leaders. That was everyone in the company, all people, including all of our EOS implementers. When you talk about your leaders, I think the beauty of them knowing as well is you can have great conversations about who wants to stick around. Yes, you run a risk of them running for the hills. But again, this is, you have to decide how healthy of an organization you built, how passionate they are about your cause. You know, all of my leadership team was very passionate about the cause. They all stayed and there was great opportunity for them. And so I hope that you will, you know, create a great opportunity for them, whatever that means. Because everybody's needs are different. And so there's some thoughts that come in.
B
I love that. And for the founder, owner, visionary, and for the driven people alongside that person, those on the leadership team, I also think that spending some time going inside is a really important part of this process. You know, your ego has been driving you for a long time, whether it's your titles or control or achievement, whatever it is, recognition, all those things. And if you have some Runway and you can start going a little bit more inside you, you'll get clearer answers. Now first, the easy thing to do that isn't too, too deep is to think in 10 year time frames. Discipline, number one, be really clear about what it looks like in 10 years from now and you can create a 10 year thinking vision if you want to do that. Could be a sentence or, you know, a story, whatever you want to do. We teach that in the book Shine. So you can find out all about that, about how to do that. Once you're clear about that and you start shedding, because we talk about shedding on these episodes all the time. This is what it's all about, shedding your shit. You realize that all those things that you've been working for all these years, those things aren't you, there's something deeper on there. And then you begin to live from your true self. And when you live from your true self, the rest falls into place with more ease. So take this as an opportunity if you do have time and even if you don't, but if you do, to really spend some time going inside and maybe starting with your 10 year thinking vision. Anything coming up for you, Gene?
A
Yeah, a couple thoughts. And again, I shared this in that episode, so I'm going to give the high level on this. But what I urge you to do is what I did. And that is, you know, the first thing I did very early on was listed the 8 reasons why I'm selling.
B
I love that.
A
Yeah. And so that's what I was able to tell those 150 people the day I decided. You know, again, it was within a month of deciding, but I was able to articulate why and then gave them an opportunity to ask questions about why that one, why Number seven, why. And so it was great conversations to come up with your reasons to do a checkup on yourself and your soul, that this is the right thing to do. Because some of you shouldn't sell, most of you should. Eventually you're going to transition your business. It just might be too early. And I urge a five year timeline when you're gonna sell your business. It's a little conservative. Most people do it in less. But for what that's worth, the second thing is to find the right buyer. So I was fanatical about making sure I found the right buyer. So same thing, a bullet point list of what I deem to be the right buyer. And that just kept me honest. As we went through the process of going from 100 interested parties down to 20, down to 10, down to the final five, it just really helped me kind of stay honest with myself. So there's some thoughts that come to mind.
B
And I just, I keep thinking about the leadership team and, you know, say you're a driven person on a leadership team right now and you have no clue. You're the operations head of operations and you just, you're not sure, you know, you know better than I. I want to say talk to the founder, ask them what their intentions are for the future. Do we ever see ourselves selling this thing? Is that appropriate?
A
I mean, I, I don't, I don't think it, I don't think a head of operations has ever asked me that question. So I can't speak from experience. Head of sales, head of marketing, head of ops, head of finance. None of them have ever asked, hey, how do I talk to my owner about that? So I, I can't speak from experience.
B
Yeah.
A
So I'd have to make something up. All I can tell you is the flip side of that, you know, yeah. If you're an owner, be open and honest with your people. And, and very frankly, I intend. I never intended to sell. So somebody just approached us, made an offer that got my attention, that got me thinking. But as soon as I started thinking that way, I let them know that. And again, one month before that, if they asked, my answer would have been, I have no intention of selling. So things change. But I was just always very open and honest with them.
B
Well, my hope, and every culture is different, but my hope is that you all can create a culture, whether you're on a leadership team or whether you're leading the team as the owner, as the visionary, where you're transparent at all times, you're clear, open and honest with each other. Because then what you can do is potentially work together on what the right thing is and find a good space for everybody. Because you know, an exit can create uncertainty for people. It can create fear. You know, it could for if you're on the leadership team, you know, it could have some resentment. If the founder is going to have a big exit and you're might going to have a small piece of it to no piece of it, you might feel that way. So, you know, I encourage you to think about the different emotions that might come up for you and also transfer it to what types of new opportunities might come to the forefront for you through the sale or outside of the sale. Get clear with your 10 year thinking. I said that a little bit earlier. And get really clear about your true self. I think that'll be very useful for you. As I mentioned before. Anything else for you?
A
Well, just a shameless plug for EOS worldwide because what we find is some of our best EOS implementers are EOS clients who sold their business and are looking for their next passion and want to help other entrepreneurs do what they did. And so I would suggest consider becoming an EOS implementer if that's right for you. Just because they're some of our best EOS implementers, I can't not take advantage of that opportunity.
B
No worries. You always have the best in your heart for people.
A
I appreciate that.
B
Okay, Gino, any last words?
A
None from me, my brother.
B
All right, well, thanks as always for joining us and we look forward to seeing you next time. In the meantime, stay focused and much love.
A
Thank you for listening in today. We truly appreciate you taking the time to spend with us and please tune in for the next episode. Until then, we wish you all the best in freeing your true self. Stay focused and much love.
Hosts: Gino Wickman & Rob Dube
Release Date: January 28, 2026
This episode delves into the often unexpected emotional, psychological, and cultural effects of selling or exiting your business. Drawing from personal experience and client stories, Gino and Rob explore why financial windfalls don’t necessarily fill the void, the importance of proactive planning, how to care for your leadership team and employees, and how moments of transition can serve as powerful opportunities for personal growth.
“They have sold their identity, and so their identity has been ripped from them. And they do go into a deep depression. And I’ve seen it now more times than I can count.” —Gino Wickman [02:27]
“I always had this idea ... we’d have this big celebration. ... It was so anti-climactic, I can’t even tell you.” —Rob Dube [04:33]
“You sold your business, you rang the bell, you achieved this thing ... It doesn’t fill the holes.” —Gino Wickman [00:00 and 06:33]
“You decide one of two things. Are you going to stay involved in the business or are you going to move on? ... You have to decide if you’re going to stay in that business. ... Or do you want to move on and ride off into the sunset?” —Gino Wickman [02:27]
“The first thing I did very early on was listed the 8 reasons why I’m selling.” —Gino Wickman [12:16]
“Most experts, advisors, will tell you to never do this. I didn’t care, and I did it... I stood in front of all of our people ... and said, I decided to sell the company. I gave the eight reasons why.” —Gino Wickman [08:00]
“We took virtually no consideration into that. ...When we shared with them the news, they were not happy.” —Rob Dube [04:33]
“An exit can create uncertainty for people. It can create fear. ... You know, if you’re on the leadership team ... you might feel... the founder’s going to have a big exit and you’re going to have a small piece of it to no piece of it...” —Rob Dube [14:42]
“Your ego has been driving you for a long time, whether it’s titles, control, or achievement ... But you realize that all those things ... aren’t you; there’s something deeper.” —Rob Dube [10:34]
“Some of our best EOS implementers are EOS clients who sold their business and are looking for their next passion and want to help other entrepreneurs do what they did.” —Gino Wickman [15:49]
On Selling for the “Wrong” Reasons:
"You climbed this mountain for 5, 10, 20 years, and you realize that it doesn’t fill this void…” —Gino Wickman [06:33]
On Team Transparency:
“As soon as I started thinking that way, I let them know that.” —Gino Wickman [14:11]
On Self-Reflection:
“Take this as an opportunity ... to really spend some time going inside and maybe starting with your 10-year thinking vision.” —Rob Dube [10:34]
On Emotional Fallout:
“I knew right away. I was like, this is a disaster.” —Rob Dube, on working for the acquirer [04:33]