307 - Solocast 68 - ENHANCED VIDEO
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Corey Kupfer: [00:00:00] Hello, DealQuest community, Cory Kupfer here with another SoloCast. I want to talk about a topic that we've alluded to and mentioned a couple of times in recent episodes, but I want to delve into it because it's so important. It's one of these things that is not talked about nearly enough, right? I'm going to talk about this specifically in terms of deals and exits.
You know, but the conversation has been brought up in the entrepreneurial world generally a little more than it used to, and that is the conversation of depression, right? There's been some, especially after like some suicides of tech founders, things like that over the last number of years, there's been a little more discussion about mental health in, the entrepreneurial world generally.
Corey Kupfer: Right. And I'm glad to see that because, you know, anytime that that's, you know, I think it's taboo and, people are being adversely affected by it to the point of even committing suicide. It's something that we really have to bring out in the open. In a deals context, I want to talk about it in this aspect.
And that is that, one of the things that is not talked about a lot [00:01:00] is, post exit depression. And I want to talk about it in a range, and listen, I am not obviously a clinician, I'm not a, you know, a doctor, anything like that. So I'm not talking from that point of view, I'm talking from what I've seen in an entrepreneurial, point of view, and what I've seen some folks do to, Counteract or avoid this.
And, you know, when I say depression, it could be like serious clinical depression leading to some serious consequences, or it could just be, you know, like general everyday depression, malaise, like, questioning where's my purpose, that kind of stuff. And obviously, that one may be more common, but it's still difficult.
I mean, think about it. You know, one of the goals that a lot of entrepreneurs work for is to build this company and that, you know, maybe they, you know, for many of them, they've done it over at least several years. And for many, it's. decades, right? 10, 15 years, 20 years, maybe. And finally, they built this thing where they created enterprise value.
Maybe they've worked 80 hours a week or day and night, at least for a period of time. No matter how hard they've worked at it, it is their babies. A lot of times it becomes their identity. You know, it's a [00:02:00] huge, huge part of their lives in positive ways and challenging ways, all that kind of stuff. But they go through all the ups and downs and challenges and, you know, and there's no entrepreneur who hasn't had, you know, ups and downs and, you know, and things like that.
And then they finally get to the pinnacle of what most companies are looking for, right? Some of the companies, the pinnacle is IPO, but for most companies, you know, the pinnacle, if they are a company that is looking for an external exit. is acquisition, right? They sell the company.
Okay. And you know, they, and maybe let's even assume for this example that they get a huge amount of money, like life changing money. They don't have to ever work again. That kids, maybe the kids don't even have to work again. Right. So this, you know, like that issue is handled and I've, because I've seen this exact situation over and over and over again.
And you would think, right, you know, they've achieved the thing. They're going to be thrilled. They're gonna be happy. They're going to be free. They can go travel the world. They can, you know, they could play golf, they can be with their family, they can, you know, focus on other things in their life. Maybe they can [00:03:00] focus on their health if that was compromised, whatever, I mean, what could be bad?
Well, you know, the reality of the situation is that too many times I have seen people have that kind of successful exit and they're depressed or they feel empty or they're lost or they're, you know, they talk about having a lack of purpose, right? And there was so much was focused on this business that they ran.
It was so much a part of their lives, a part of who they were, a part of how it impacted everything they did, positive and negative, right? It's how they afforded to send their kids to college or live in a particular area or take the vacations they did. But it's also, you know, where they spent all their energy.
Help may be healthy or not, but, and whatever it was, you know, It's now gone, right? It's gone. So now what? And it's interesting. I think like on a very deep level, one way I would describe the question that comes up for people, [00:04:00] you know, for exited founders is, okay, who am I now, now that I'm not the founder and CEO, whatever you are, right, of X, Y, Z company.
And you know, that sort of, I want to highlight something I said earlier, that question comes out of the fact that for so many entrepreneurs. Their identity is so tied into their business that they've created just because it's taken so much of their time, effort, energy. And it's also, a reflection of them in many ways, right?
You know, that's one of the great things about the entrepreneurial journey is that you get to create something in your own vision values. You know, you don't have anybody else telling you what you can and can't do. Obviously you have constituents, you want to keep your clients, you have funders, you got that.
But the point is you don't have a traditional boss, right? The reason you started the company is to create something in the vision that you wanted to create. And if you're successful, you've done that at some level. So it is become sort of this part of you. It's part of your [00:05:00] identity. Well, now that's gone, right?
And I think at a very, very deep level, I mean, people may not express it this way, but I think maybe, you know, the ultimate question may come to down to who am I, if I am not founder, whatever of XYZ company. And that's a tough question for a lot of people to answer because they haven't, like, until you have the absence of something, it's hard to know what that's going to be like.
You know, this old metaphor about, fish in the water, you swim it, right? If you've been swimming in this ecosystem of your company, of this life in which your company, you know, and building your company has been a huge part of it, and that's the water you're swimming in, it's hard to understand what it will be like when you're out of that water until you're out of it.
Right. And you may have, you know, I mean, you may think, Oh, you know, it's going to be great. But I think more and more entrepreneurs, because they're seeing some of their fellow entrepreneurs who've been successful struggle after they [00:06:00] exit with life changing money, even that there's a start of a discussion in the entrepreneurial community, in the exiting, you know, entrepreneur community of people who look and exit and says, Hmm, maybe there's a little bit of a cautionary tale.
You know, maybe I need to think about this a little more because. I didn't even, like, it didn't even cross my mind, but now I see Joe or Sally exited and they're struggling, right? And listen, part of this is also the authenticity and honesty of being in circles where those exiting founders are really sharing that they're struggling, right, and not keeping up a good face.
That everything's great. Oh, yeah. Well, that's, you know, and I think that's also happening more. So I don't want to oversimplify this to, to just bring it down to the fact like, who am I? But I think that is the fundamental question. But it's also, you know, it sort of, comes out to, all right, you know, everything from what do I do with my time to, You know, and some people can listen I have a client, I don't know, it's got to be 15 years [00:07:00] ago now who exited and, he had built this business wherever.
And, you know, a lot of times when entrepreneurs exit, those of us in the space, they go, yeah, you know, they'll, yeah, we'll see how long that lasts, they'll, Take a month off or days on the joke is, you know, three days later, all of another business, or sometimes, you know, whatever, they'll travel the world for a year and then they get restless.
Right. And that personality and that drive and that thing that had them become an entrepreneur in the first place needs to go somewhere and they'll start another business. And sometimes people surprise you like this. That's where I was mentioning 15 plus years ago. We all, you know, those of us who were, the bankers, the, you know, finance people, us as lawyers.
We're all making those jokes, whatever. And you know what? He never started another company. It was fine. They took an RV. They spent a year in RV going around the country, which was a dream of theirs. Right. They built a, you know, a beautiful house on the beach, and you know, plays golf and the travels and they're very happy.
Right. There's some people that works. But for others, it doesn't. Right. And, and you know, [00:08:00] there's always a question of what's next, whether that is building another business, whether it is. Having some other interests, you know, many, many, folks who do well end up investing other companies because they don't want to run a company again.
They know how challenging that journey was and things like that. So they're like, you know, but they still want to be in the game. So they become investors. They have the money, they become investors at the some that works for some that becomes very dissatisfying because they don't have any control over things.
It's not the same kind of energy you get from building something on your own. But for some that works, right? So. You know, you got to figure out what's best for you, but. It comes up sort of in every aspect of your life. Like I said, what do I do with my time now? Somebody asked me, Oh, what do you do? What do you say?
Right. Oh, I exited my business. And inevitably people are going to ask you what's next. Right. Like you have no obligation to have an answer to that. You know, I joke with folks. I was talking to somebody earlier who was, It was, getting engaged that we were joking about [00:09:00] this, that, you know, society is so like, you're dating somebody for a while.
They're like, when are you getting engaged? You get engaged. You're like, when are you getting married? You get married. Like when are you having kids? It's like, yeah, your first kid, when do you have a second kid? Like, it's something about our society that always like, you know, wants to not only know, but there seems to be this societal pressure on what's next.
And it's, you know, there's some similarity in the entrepreneurial world, right? When you exit, somebody's gonna say, Oh yeah, what's next? What are you going to do? Right? And it's sort of like, I mean, some people are comfortable saying, Yep, don't know, figure it out, take some time, whatever. But even then, sometimes there is this thing about, it just strikes up a chord within themselves about, What is next for me?
Right? What am I going to do? And especially as some, You know, entrepreneurs are fortunate enough to exit at an earlier age and as we're living longer, right? I mean, sometimes people exit, you got 30, 40 years or more, you know, like there's a whole, it's not like you're exiting it, you know, at age 60 when people died at age 65, right?
It's a whole different analysis. [00:10:00] When you do that, it also, you know, changing your family dynamic, right? You've been out working all the time and now, you know, you're home, whatever. I mean, that could be great. Spend more time with the family. So that's, that causes tension, right? You know, everybody's in their routine.
Maybe your kids and your significant other, if you have one, you know, it disrupts their routine to have you around. Maybe, a lot of the people you associated with have not exited yet and they're still working. Okay. Well, now there's this connect because. You don't have stuff to talk about in terms of your company, their company, they're busy, you have time.
You know, there's so many of these things that come up. It's such a change. Once you exit a business and some people deal with change better than others, right. Even if it, you know, is generally a good thing. Sometimes the actual, all those factors and change and uncertainty, cause challenges for folks.
So let's talk a little bit about, you know, there's more and more people it's early, but just starting to talk about. how they are, first of all, that they are aware of this risk, because I [00:11:00] think for a long time people weren't, you know, it was happening to folks, but it wasn't, you know, it's not something that people would tend to just, you know, in terms of the, their willingness to be open that they're struggling.
And also it's a tough conversation to have, right? How many people are you going to be able to go to to say, oh yeah, I actually my company, I have 50 million in the bank. But 10 million or a hundred million, you know, whatever the number is, right. But let's say I got 50 million in the bank, but I'm struggling.
Like how many people are going to be empathetic to that? Now, obviously, hopefully you're good friends and fellow entrepreneurs and people who really get it would be, but still is, there's a, you know, it's easy to feel ungrateful, like, or was something wrong with you or, you know, who's going to want to hear that.
Right. So it's becoming fortunately a little more acceptable to have those conversations. And there's also like, I know some folks who've exited. Who, there are now masterminds or groups or, you know, folks that get together who all have exited because, you know, now you have similarly situated folks and it's easier to talk about this kind of stuff.
And there's a shared experience, [00:12:00] right? Because if somebody hasn't exited, they may have empathy for you, but they haven't been there, you know? So fortunately that's happening. And also because it's become a little more conscious because some more people are talking about it, it helps the entrepreneurs who have not yet exited try to figure out how to avoid that issue, right?
How to avoid. Finding yourself without purpose, how to avoid getting depressed, how to avoid, the struggles that may come with the changes, you know, within yourself or within the people, you know, family, friends, et cetera, who you interact with. And some of the things, I don't profess to be an expert on this.
I haven't personally exited, but. I've spoken to a lot of folks and I know some folks who've been through this and we've had these conversations. And in fact, I think I've mentioned, but it's one of the reasons why I have Damon Gersh kicking off, the, my, the EO, deal exchange conference that I'm running in, in, September 11th to the 14th, in Austin, Texas, because I want to bring this forward.
It's one of the things he's gonna be talking about. [00:13:00] on how he had an experience with folks that, with somebody specifically that he knew really well, who really struggled, and how that made him hesitant to exit, but then he did, and he's done it well. So what are some of the things that I've gathered from These folks that have done it successfully.
Well, again, the first point is awareness. Okay. If you are not aware that it's a potential problem, you're not going to anticipate and try to deal with it. The second thing is really sort of accepting that this is a real risk, right? You know, like you might be aware of it, but if you say, oh, that's not going to happen to me, well, you know, that might just be your ego talking.
And if you haven't really made plans for this, you may find that. Well, you didn't think it was going to happen to you, but it did. And I've heard stories of that, right? So what are the things that have helped folks who I've seen who've done it successfully? Well, one is, let's go to that core thing about who am I, right?
Really examining that, like, who am I as a person? Who am I as a human? outside of my company. Try to [00:14:00] understand that. What is important to you? What else drives you? Right? Is there a cause, a nonprofit, a, you know, a particular thing? Is there an industry? Maybe you don't want to run your company, but you're still passionate about your industry.
So it will drive you to consult or mentor or be on a board or be an investor in companies, you know, in, in or around your space. You might have restrictive covenants on working directly with a competitor, but maybe there's other things around your industry or once you get outside of your restrictive covenants.
You know, maybe you are still enthused about the industry. Maybe it, maybe, like I said, it's not a profit. Maybe it really is spending a lot of time with family, not because of by default, but that's really a drive and a purpose that you've been missing. And you're going to have that be your driver. Right.
And so the more you focus on your new purpose, or maybe it is, has been part of your purpose, but where you're going to double or triple down, because now you have space [00:15:00] on that other purpose outside your company, And the more that you can examine and answer the question of who am I without my company.
Now to some extent, again, I think there's an aspect of that you will never get until you're out of that water, but you can try to anticipate as much as you can. And I think you can get somewhere down the road. Of looking at that question in advance and then looking at how am I going to spend my time?
Right. Like not being in a position where no, what am I going to do? And you're bored or you're doing stuff that's not healthy, or you do it stuff. That's just to fill the time. Right. And a lot of that ties in, right. You know, if you clearly have a purpose and you're going to get excited about, you know, certain causes of nonprofits.
Okay. Well, you'll do that. Maybe you'll dedicate some time there. If you want to do one, right. Check. You know, if you want to spend more time with your. With your kids, then, well, okay, you're going to plan to, do that. But thinking about these things in advance, and not just, although I think it is important to think about where am I spending my time?
What is happening on an activity level? Making sure we're [00:16:00] also looking at that deeper inquiry about, The psychology about how am I going to feel? Who am I going to be? What is my purpose going to be? What am I excited about? Like, one of the ways that some people have put it is that you need to have something you're moving towards, right?
So when you have a, an exit, a lot of times the whole goal is that's what you were moving towards. You're moving towards that exit and coming out of that exit, maybe you're moving away from having to run the company day to day from the stress from. From all of that stuff from the things that distract you from this other stuff.
But if you don't really know what the other stuff is, because that's all you've done is run the company. Or the other stuff doesn't seem to have enough pull to pull you forward, right? To be that positive thing that you're moving towards. That's what people run into trouble. So if you're able to identify those things and be excited about and passionate about moving towards those, not just getting done with and selling your company and having that achievement, then, you know, [00:17:00] that helps.
The other thing is that, you know, I'm going to talk about celebration because. A lot of entrepreneurs are horrible at celebrating, any win, right? They just go on to the next. And that's the other thing. Even though I'm saying you need to have a vision and a purpose, something moving a positive too, it's also doesn't work well when you're sort of bringing the same energy and personality to that next thing without, you know, because you think selling your company is going to, you know, sort of get you free or have you be able to shift.
But you are who you are, right? And if you just keep bringing that same energy and issues and stress or whatever, then the next thing you're up to, then things aren't going to change. And if you want them, maybe you don't want, maybe you love that. That's fine. You just want to do it with something else.
That's great. That's the reason why some people start other businesses, even though they may not need the money, right? But if part of your thing about the exit is that you want something different, Then looking at your way of being and not just defaulting and bringing that way of being it's in a new thing Where [00:18:00] you might end up in the same frustrations or issues or challenges or not, you know Achieving the other things you want to achieve because you haven't shifted who you are So one of the ways you do that is to really take stock and look at that and see what you want to change.
The other way is to really make sure you sell, first of all, you should just celebrate, right? I mean, come on, you sold your company a lot of money. Beyond getting the money and, you know, smiling about that, like, do something. Like, take space, acknowledge it fully. And part of the celebration is just celebrating, is not just looking past and always, you know, being on to the next carrot.
But part of it is also taking a step back and completing that chapter, right? The celebration could be a close of that chapter and really acknowledging, you know, what you did there and how successful you were and that kind of stuff, right? And then be able to look at this new thing that I'm suggesting you be pulled towards as a, you know, as a new chapter that you're excited about, right?
And not by default, just dragging in all the old garbage from [00:19:00] before. And if you can do that, then it allows you to make some new choices from a cleaner place, as opposed to just doing the next thing the same way you did the last thing. And having it, you realize that maybe it wasn't the last thing that was the issue for you was the way of being around how you did that.
And I'm bringing that into the new thing. Right. So also I really encourage you to take a step back to, both celebrate and complete that chapter. And then from a new place, from that new way of being, from that new person you want to be, from that new purpose, that's driving you from that new vision for that thing, that's pulling you forward, right?
Create this, something new that you're excited about. And start to look and do that before you exit, right? Because after you exit, you know, too late, I mean, some of the stuff will develop further after you exit, you'll learn more about yourself in the absence of that business. And maybe, you know, you do want to take some time, you know, traveling the world or whatever it is, to sort of have a break and decompress and integrate that [00:20:00] experience.
But at some point you want to start looking forward and hopefully earlier on you. Would have an idea, you know, what it might be, and then you would crystallize it and solidify it and clarify it, you know, once you get out. So there's so much more to be said on this issue. Again, I don't profess to be the exit expert.
I'm mainly relaying, you know, what I've seen from the so many entrepreneurs I've seen exit. And who have been challenged or done it successfully. I hope this, you know, most other things sparks this to be a much more open conversation that, and that people share their experiences and that, you know, more resources and support is developed around this for folks.
And, you know, as listeners, as deal makers, as entrepreneurs, I think, you know, this community can understand. Something that other folks may not. I mean, obviously people outside may say, Oh, poor person, you know, exit it with 50 grand, 50 million in his bank account. Well, boy, he's struggling. And I get it, right.
Compared to somebody who's got, you know, is unemployed, who's got [00:21:00] three jobs or whatever, it's easy to judge but listen, we all have our own struggles and I don't care who you are. If you suddenly feel like you are without purpose, or you don't know who you are, you know, in terms of your identity, you know, that's tough, that's tough, no matter how much money you have in the bank.
And it's evidenced by the fact that people have had really bad circumstances, you know, despite having money in terms of their mental health issues, and things like that. So I'm really committed to having people avoid that, to having that ultimate exit deal, you know, be something that is not only celebrated as an end point, but is also a phenomenal launch point.
But something else great in your life and that you are successfully able to make that transition, do it positively, and then go on to whatever is next for you. Whatever that looks like. All right, folks. Have a great week. And look out for next week's episode with another great guest.
