Denise Logan

Selling a business is more than a financial transaction. It is also a major emotional transition. Denise Logan, author of The Seller’s Journey, joins Craig Castelli to explain why owners sometimes delay, derail, or walk away from strong deals. They discuss fear responses, identity after ownership, family dynamics, separation anxiety, and the hidden emotions that can shape M&A outcomes. Denise also shares how advisors can recognize these signals, ask better questions, and help business owners prepare for life after the sale.

  • Chapters Include:

    Meet Denise Logan

    Transaction vs. Transition

    Denise’s Exit Story

    Spotting Seller Hesitation

    Life After Work

    The Sailboat Deal

    Fear and the Brain

    Five Fear Responses

    Content vs. Context

    Triggering M&A Language

    When Denise Steps In

    One More Year

LISTEN TO THE CLOSE

Exploring the Art & Science of dealmaking

Welcome to The Close M&A Podcast with Caber Hill Advisors, where we bring you exclusive insights from M&A experts, business owners, and industry leaders navigating the complexities of buying and selling businesses. Hosted by Craig Castelli, this podcast demystifies the dealmaking process, shares success stories, and offers invaluable lessons for business owners and investors.

Craig Castelli headshot

MEET YOUR HOST

Craig Castelli, Founder & CEO of Caber Hill Advisors, is a trusted M&A expert with decades of experience advising business owners through successful transitions. Alongside a rotating roster of advisors, entrepreneurs, and investors, Craig brings engaging conversations that illuminate the world of middle-market M&A.

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ABOUT THE EPISODE
Denise Logan

Selling a business is more than a financial transaction. It is also a major emotional transition. Denise Logan, author of The Seller’s Journey, joins Craig Castelli to explain why owners sometimes delay, derail, or walk away from strong deals. They discuss fear responses, identity after ownership, family dynamics, separation anxiety, and the hidden emotions that can shape M&A outcomes. Denise also shares how advisors can recognize these signals, ask better questions, and help business owners prepare for life after the sale.

  • Chapters Include:

    Meet Denise Logan

    Transaction vs. Transition

    Denise’s Exit Story

    Spotting Seller Hesitation

    Life After Work

    The Sailboat Deal

    Fear and the Brain

    Five Fear Responses

    Content vs. Context

    Triggering M&A Language

    When Denise Steps In

    One More Year

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LISTEN TO THE CLOSE

ABOUT THE PODCAST

Exploring the Art & Science of dealmaking

Welcome to The Close M&A Podcast with Caber Hill Advisors, where we bring you exclusive insights from M&A experts, business owners, and industry leaders navigating the complexities of buying and selling businesses. Hosted by Craig Castelli, this podcast demystifies the dealmaking process, shares success stories, and offers invaluable lessons for business owners and investors.

ABOUT THE HOST
Craig Castelli headshot

MEET YOUR HOST

Craig Castelli, Founder & CEO of Caber Hill Advisors, is a trusted M&A expert with decades of experience advising business owners through successful transitions. Alongside a rotating roster of advisors, entrepreneurs, and investors, Craig brings engaging conversations that illuminate the world of middle-market M&A.

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Craig Castelli:
Welcome to Close M&A Podcast with Caber Hill Advisors. I’m your host, Craig Castelli. Today we’re going to tackle a slightly different, more human side of M&A. My guest is the seller whisperer, Denise Logan. Denise is a sought-after speaker. She’s a bestselling author of the book, The Seller’s Journey. And she has a very unique background combining time as an attorney, a mental health professional, and a business owner that gives her a very unique skill set and has enabled her to help close over $3 billion worth of transactions. Although Denise, I should probably call them transitions, not transactions, right?

Denise Logan:
I love that. Good point. Good point.

Craig Castelli:
So tell us, I guess, about that distinction itself to kick things off. You are working directly with business owners to help them tackle some of the hidden challenges, at least hidden to us traditional advisors, because these deals really are about a lot more than just the deal. So set the table there.

Denise Logan:
I love that. So Craig, I feel like there are two different things going on when an owner is selling their business. There is the transaction, the actual sale process, and then there is the transition, the emotional change that is happening for an owner. For most owners, as you know, they will only go through the process once. And that transaction is where everyone’s attention is focused, but this is the single largest transition in an owner’s professional life. And likewise, they only go through it once.

Craig Castelli:
Yeah. And I think your stat is that more than 70% will not follow through with the sale. Is that true?

Denise Logan:
It is so crazy. There are lots of reasons why business owners come to the market. So sometimes they’re just testing things. They want to see what might someone pay for my business? Sometimes someone else is nudging them. So a spouse who says, “Aren’t you ready to retire? I think you’re ready.” Or a child, an adult child who wants to acquire the business. But sometimes it’s the worst things like there is a death and the business is on the market or an owner gets old and sick and suddenly they’re in the market. I think about all the different aspects of what brings an owner to the market. And for an owner who has prepared for this process, you know this fully well in your own process, for an owner who has prepared for their exit, they are so much more likely to have a successful and happy transition. For those who wait too long or are forced into a process not by their choice, the result is often very tumultuous. And you and I know this, we will all leave our work at some time, voluntarily or involuntarily. And I’m just enough of a person who likes to know how things are going to go that I would rather have my transition on my own terms instead of by a market condition or a change in my business.

Craig Castelli:
Yeah, you and me both, and you have done something that I haven’t done personally, which is you sold your own business. How much did that experience or perhaps what followed that experience shape where you are today?

Denise Logan:
Oh, every bit of it. So in my early life, I was a therapist and then I became an attorney. And right now your listeners are thinking, “Why didn’t she use that good therapy skill to keep herself from becoming a lawyer?” And so I built a law firm, and when we reached 50 lawyers and 300 support staff, I exited my practice. And I did a super ugly, choppy exit because truthfully, I waited too long. I was at the point where I would’ve given my business away to be free of it. And so when that time came, a couple of things happened. So I was excited about it, but I was also sad. All of those things were going on. And can I tell you a fun little story?

Craig Castelli:
Please do.

Denise Logan:
So this was back in 1999, so when we still had file cabinets and desks and people came to work. And so the firm that acquired us sent all of their trucks to collect the file cabinets and the desks and the computers and all the things. And so as the last truck was turning out of the driveway, I just wanted to see it. So I leaned in toward the window and I smacked my head right on the glass. And the tears were pouring down my face. And then I thought, I don’t think I hit my head that hard. And I realized, oh wait, these tears are about something else. I am watching an entire chapter of my life turn the corner. And a few days later, I was out on the patio at home reading a magazine, drinking iced tea, having just a perfectly relaxing day. And I thought, oh, I got what I wanted. Oh no, I think I got what I wanted. Was that what I wanted? Did I get what I wanted? And the people around me did not understand that emotional turmoil. Yes, I had gotten exactly what I wanted. And yet later I started to question, was it what I wanted? Did I get all of those things? And I think for many owners, we are so focused on that exit. We put our lives on hold or have a projection about when I get there, life will be like X. And when we arrive, it is like that and it’s different. And so it absolutely informed the work I’m doing now. After I exited my practice, I got rid of my house and bought a motor home and I took off for what I thought would be six months and turned into almost five years where I traveled all over North and Central America. And that’s a conversation probably for a beverage. But when I came off the road, I joined a friend’s business who was preparing for sale. Over the next 10 years, we tried to take that business to the market three times. This will give you nightmares, Craig. Three times we went to the market and the owner pulled out at the last minute because he couldn’t see what his life would be like on the other side of the sale of his business. So I left and did a research study about why business owners get stuck. Why are they like me? I waited so long, I would’ve given it away. Or why are they like him where they go too early and can’t pull the trigger? And that has informed the last 17 years of the work that I’ve done coming alongside owners and their advisors to navigate that emotional arc of letting go.

Craig Castelli:
So you said that this is predictable, and I can see from your vantage point, having worked with so many sellers at this point on the heels of your own personal experiences, how you can see the tells that certain owners may have. I’ve been doing this my entire career and it still sometimes catches me off guard. So what is the investment banker or the attorney who’s advising these business owners but focused on the deal to do? How do we spot some of these signs before it’s too late and we have a deal blowing up around us?

Denise Logan:
Yeah. So let’s start. One of the early questions that an owner is often asked by a professional advisor is what’s your plan after you sell the business? And can we agree that golf, travel, and grandkids is not a plan? That’s a little bit of a plan, but it’s probably not enough to sustain them. So one of the first questions that I will ask an owner is what does work provide for you other than money and financial security? Because you’re not selling your business unless you are getting money and financial security. And so let me just say that question again. What does work provide for you other than money and financial security? Because those things are not going away just because you get a big sack of cash. So what things do you get from work, Craig, other than money and financial security?

Craig Castelli:
I get a challenge every day, numerous challenges every day. It’s a sense of identity. It’s a sense of purpose in building a firm. I mean, it’s a lot to think of all of a sudden not returning to the next day.

Denise Logan:
Yeah. And I’ll tell you some of the ones that I hear, and I ask owners to come up with 15 distinct answers. And right now you might be thinking that’s a lot. But it’s things like structure.
Work provides structure to our day, to our week, to our year. It’s a place to go. During COVID, we were all desperate to get out of our houses. And PS, our spouses were desperate for us to get out of their houses too. It provides friendship, intellectual stimulation, the thrill of the chase or the thrill of the kill when it’s a sales-related piece, but it also provides things we don’t talk about. Things like power. Because I don’t know about you, but at work when I say I want something done, it generally happens. The people who live in my house do not necessarily think that it has the same weight. We also get things like at work, we are the keeper of wisdom. We’re the place that people come to ask for. So what I often say to an advisor and to an owner is let’s identify what those things are that you’re getting from work.
And then let’s look at where else can you begin getting those needs met before you leave your business so it doesn’t feel like a black hole when you’ve left. So for example, for a lot of our owners, their employees and their customers, even their competitors are their friends. And I will often hear from an owner because they will tell me things they might not tell you. Things like, “I don’t have any friends. Who am I going to hang out with when I leave my business?” And so we begin working on that. I know the question that you asked was what can you watch for? I think being able to ask these deeper questions of them at the beginning, it does scare them a little bit. They go, “I don’t have an answer to that.” But it’s better to know that upfront than to be four weeks from the closing and suddenly this starts churning up. You and I know, I call it, we used to call it the Sunday scaries when we were in college. Now what it is for an owner, as they get close to the end, these things are starting to come up. But when everyone in the process is talking to them only about the transaction and money, the emotional pieces that come up will often be framed in transaction or money, even though they’re not about them. Should I tell you a story about that?

Craig Castelli:
I’m sorry to interrupt. Yeah. If you make this list of 15, is there a goal to achieve one-to-one replacement for all 15 items? Or is there just some higher level of consciousness and perspective that can give an owner peace that yes, they’re leaving this chapter behind, but they can still have some value in their lives?

Denise Logan:
Yeah, it’s to sort out, and it will not be one-to-one. The truth is that there will be no other part of our life like work that will meet all of those needs the same. But we often hear owners told, “After you sell your business, join a board or join a charitable organization.” That’s great if you know what need it’s going to be met. But if you are joining the board of a charitable organization to get your power need met, that might not happen. Or your grandkids may not want to spend all that time with you. So we’re not looking for one-to-one, but it’s the awareness of what are those things that if we don’t have an opportunity to acknowledge them, they will reveal themselves at another time. So an example of that is a deal that I worked on several years ago. And by the way, don’t get hung up, listeners, don’t get hung up on the deal size or the industry. The emotional arc that an owner is going through is exactly the same. Doesn’t matter the size or deal. But this was an $85 million manufacturing company. Eight weeks before closing, the seller suddenly announced he would not take a penny less than nine times EBITDA, which would be great, except his deal was at 6.2 times EBITDA. So I had a little bit of a delta and he stopped talking to everyone. So the investment banker introduced me and said, “I think my seller went crazy.” I was like, “Yeah, it sounds like it. Let’s see if we can figure out what scared him and what hidey-hole he went into.” So his original plan was to sell the business, buy a sailboat, and sail around the globe. You can get a pretty good boat for 85 million bucks, so this is probably not actually about money. And then I learned that two weeks before he asked for this financial unicorn, his wife had said, “I’m not doing that. I do not want to be stuck on a boat with you far away from my grandkids. We’re not doing that.” Can we agree, Craig, there is no way he’s coming back to the deal team to say the deal is off because my wife won’t let me do what I want to do.”

Craig Castelli:
Zero chance.

Denise Logan:
Instead, he asked for something that he knew he couldn’t get so that when the deal fell apart, it would be about you, not about him. So once I sorted out what was happening, I did one-on-one work with husband and wife separately, and then created a solution where he would buy the sailboat and sail. And every six weeks she would take one grandchild, fly to where he was. They would do two weeks on land, building memories with the grandchild. Then she would fly home, he would sail on, and our deal was back on track, closed on time at its original asking price, because it was never about the money. It was about something else that he didn’t feel secure in saying. And sometimes people will say to me, why didn’t his wife speak up earlier? To which my answer is, have you been married longer than five minutes?
Because if you’ve been married longer than five minutes, you know you don’t say no to every jacked up idea that your spouse comes up with. And they were struggling with what we call relational grief, what they thought their life would be like when they sold the business and what their life was actually like.

Craig Castelli:
Yeah. It’s amazing to me that, not that those issues happen behind the scenes or in relationships, but that there’s never a discussion with the advisors. This is what I want to do. This is what’s holding me back. This need to put on heirs or keep things confidential when all it does is enable all of us to do a better job for that client.

Denise Logan:
Right. So if we think about what’s happening, change triggers fear. And fear shows up for us in many different ways. So want to do a little brain science?

Craig Castelli:
Let’s do it.

Denise Logan:
About how fear shows up? So there are two parts of our brain. One is called the amygdala. It’s the fear sensor of our brain. It’s the oldest part of our brain, often called the lizard brain. And it is designed to keep us safe. But it’s a little bit of a dumb part of our brain because it is always scanning the environment, looking for danger. The challenge with the amygdala is it can’t always tell the difference between real danger and perceived danger. So if when you were a young boy, you were attacked or threatened by a big black bear, your amygdala would spot a big black dog and tell you to run. The other part of our brain is called the prefrontal cortex. It’s the thinking part of our brain. So do this with me, Craig. Take your hand, bring your thumb across the palm, and wrap your fingers over the top. We’ve created a visual representation of our brain. The amygdala is the thumb. It’s safely tucked in. And our thinking brain, the prefrontal cortex, is wrapped around the front. Now move your thumb around a little bit in there. What do you notice?

Craig Castelli:
There’s not very many places for it to go.

Denise Logan:
Not much movement. But if you move your thumb more aggressively, you could literally flip your lid. So the amygdala gets hyperactivated and it will pop our thinking brain offline. So think about how many things are happening for an owner in a transaction that are kicking up fear.

Craig Castelli:
Sure.

Denise Logan:
It’s kicking up things like we’ll just say due diligence is happening. And you’re going to ask all kinds of questions or the buyers’ reps are going to ask all of these questions. The owner is used to being the person who knows everything about their company. They can answer any question, but I guarantee you are going to ask questions that they don’t know the answer to. And that’s going to trip up a whole internal dialogue. Oh my gosh, are you going to think I’m stupid? Are you going to find I did something wrong? Oh, no, oh no. And imagine our poor little amygdala is like kicking our thinking brain off. Most owners as a protective mechanism will shut down those kinds of conversations or they will pull back and give you a front. Because what’s happening for our fear center and for that part of our brain is it feels like danger. It feels like an existential threat.

Craig Castelli:
It’s like actual fight or flight kicking in.

Denise Logan:
Yes. Oh, you’re like my straight man here today. Okay. So fear shows up in one of five ways.
Fight, flight, freeze, fawn, F-A-W-N, like the baby deer, and submit. So fight, flight, freeze, fawn, submit. We will use all five of these at different ways, but typically we have a pattern that we go through. So you know what fight looks like, right? Put up your dukes. We’re going to argue, argue, argue. Then we have flight. Flight is when the owner is trying to get away. So they may ghost you. They stop taking your calls or they just check out of the conversation. Freeze in a professional setting often looks like overthinking, over-processing. We’re going to spin it around and around. Fawn looks like people pleasing. That’s where they will say things like, “Yep, yep, I’ll get you those documents.” And then they never do. What’s happening inside is our brain is saying, “I will say whatever I need to so you don’t hurt me.” And then the last one, submit. If you have a teenager in your house, you definitely know submit because it looks like this. Fine. Whatever.

Craig Castelli:
How do you know that I experience that weekly?

Denise Logan:
And what we see is we each have a pattern. So my pattern is freeze, fawn, flight. If things get a little janky in a process or in my own personal life, what’s going to happen is I’m going to freeze. Then I’m going to start over-promising. Really? Please, please. And if I can, I’m going to get away. If I can recognize that pattern, and this is the piece for advisors as well as for owners, if we can recognize our own pattern, we can stop it before we escape from the process. So do you know what your pattern is, hearing it?

Craig Castelli:
I don’t. I don’t. Of all the personality testing I’ve done about communication styles and things like that, I’ve never gone through an exercise like this.

Denise Logan:
The interesting part is I’ll often say to men, so think about the conflict that you have with your spouse. You don’t need to talk about it here on the podcast, but think about that.

Craig Castelli:
Thank you.

Denise Logan:
And I’ll say to them, “So if there’s conflict with your spouse, what does she first do?” And often they will say, “Fight.” If fight doesn’t work, what does she do next? Fight harder. But often what’s happening is our pattern is tripping someone else’s pattern. The reason I do this very early with owners and advisors is because when an owner starts to get scared, so let’s say they start pulling back. I’m betting that your fear is going to get tripped up as well because you’re like, “Don’t go. Don’t go.” And we might chase them, which for an owner that is fleeing, that will actually make them run harder and further away. So a lot of what we’re doing in the process is noticing what’s happening. What I will say to an advisor is two things are going on in the transaction all the time. We have content. So what we’re talking about, there’s a change in the deal terms, the valuation came back. And then there is the context, what’s going on emotionally under the surface. If we are attuned enough to our client, we can notice, oh, they’re starting to pull away or they’re starting to fight. We can pause the content. So we stop talking about the contract and we address what just happened? Something just scared that person. And it’s especially important when fight is front and center. Because often we think, why are you being a jerk? Why are you acting like that? If we’re able to pull back enough to say, “Oh, what just scared that person?” That’s a very different emotional reaction. And then we can address what’s actually happening under the surface so we can get back to the top, back to our content. I always say, “Do you know the argument you have with your spouse about why you didn’t put the mustard back on the right shelf in the refrigerator?” Can we agree that it’s never about the mustard? It is always about something else. But we often keep arguing about the mustard, and that argument continues to surface up instead of addressing what’s really under there, which is, “Honey, let’s pause about the mustard and let her say what’s true,” which is when you don’t put the mustard back on the shelf where it belongs, it makes me think you don’t listen to me. And when I think you don’t listen to me, I worry that you might leave me. Whoa, that’s a way different conversation than why are you so dumb you don’t know where to put the mustard back? And then we can address that emotion that is going on under the surface and diffuse the conflict. So a lot of what I’m doing in the transaction is understanding what is that that’s going on underneath? Because otherwise an owner will reject a perfectly good offer and they will make it about something that no matter how hard you try to fix that issue, it’s never fixing. That tells us that emotion is in the way. Because they’re smart people. They’ve built great businesses. If they are not doing the next thing that makes sense, emotion is in the way. And that’s where I live.

Craig Castelli:
Yeah. So are you suggesting that each time we onboard a new client, part of that initial meeting should involve a discussion about how they fight with their spouses?

Denise Logan:
Yes. And it’d be an interesting piece, especially if their spouse is in the room, what that means.

Craig Castelli:
Right. Yeah. We’ll have to record that one.

Denise Logan:
I think a lot of times knowing about our own pattern is more than half of the battle because we are contributing to some of the drama that happens in a transaction. You think about some of the language we use in the industry. We talk about things like low-hanging fruit. And in an owner’s mind, what they hear is, “Why am I so dumb? If it’s low-hanging fruit and it’s easy to harvest, why didn’t I do that? Oh no, now I feel ashamed. Shame is going to trip off fear.” They might pull their deal off the market so that they’re going to ostensibly harvest that low-hanging fruit. You and I both know that if they could have done that, they would have done that. And so canceling their deal or pulling it off the market to do that next thing isn’t likely to happen. And in that moment we know, oh, that person felt shame. Can we change a couple of things? Number one, we don’t use triggering language like that. We learn about those things. In the industry, we will call it a tombstone. When someone sells their deal, we post a tombstone. For Pete’s sake, this is their baby. They have entrusted their baby.

Craig Castelli:
You know, you bring up an interesting point with the jargon we use too, because we talk about owners taking offense to somebody calling their baby ugly. And we then cast them as somebody who is overly sensitive and can’t take criticism. And I think you’re going to tell me that once again, there’s a lot more going on underneath the surface than we may see as somebody who just took offense to a sharp or critical question.

Denise Logan:
Right. And just think about your own children. If someone actually said, “Wow, your kid is so ugly,” wouldn’t the hair on the back of your neck get up? And certainly your wife’s going to get all mama bear about it in that moment.

Craig Castelli:
To say the least.

Denise Logan:
And so sometimes even as owners, yes, we may have to deliver news to them that is difficult. Can we think about the way you would deliver that information in a caring way as opposed to a, “I just need to get this out. I need to tell you that your baby is ugly.” Even that internal language that we use around how we think about delivering the message is going to change how an owner receives it. And we think about things like, okay, all of us here in the conversation have sold a house at some point. And you’re under contract and you think, woo, this is great. And then the home inspection comes in and the owner says, “You need to fix the roof.” All right, I’ll fix the roof, but I don’t like it. And then they don’t like the way that tree root is kicking up one of the pavers on the sidewalk, so you fix it. But then they want the thermostat moved two inches to the left and you’re like, “I will burn this house down instead of doing that.” It’s not about the thermostat. It is about the inability to reregulate between each part of change in the transaction. And as professionals, we know, we even say every deal dies seven deaths. There’s a lot of language about it. For an owner, the metaphor that I would use is the children’s game Chutes and Ladders. So I grew up in Canada where they call it Snakes and Ladders, and I’m not really sure who thought snakes in a children’s game was a good plan, but we all get it. You’ve got your little marker, you spin the dial or roll the dice, and you hit the first ladder. And you’re moving up the board thinking, “Woo-hoo, I’m going to win this game.” And two rolls later, you’ve got to chute. It brings you back down the board. If we are able to help an owner emotionally reregulate each time this up and down happens, they will be able to make it all the way through the process. If, however, we leave them with a, “Oh my gosh, that just happened,” they’re going to be like a child and flip the board. And they’re going to leave. And so over and over, I will hear advisors sometimes say, “My client’s acting like a child.” For sure. Because the fear response triggers a very young part of us, an existential, “Am I going to survive this moment?” And so sometimes slowing down the process a little bit can make all the difference in whether or not we get to the end. And that usually scares advisors when I say slow down, because there is a myth in the industry that time kills all deals. And of course, long extended gaps of time do. But what I’m talking about sometimes is an hour or two or three days where we need to help someone get back online so that we’re not running all lizard all the time in the deal, but we’re able to get the thinking brain back online.

Craig Castelli:
So who usually brings you into deals and does the person who makes that call or their role tell you anything about what’s going on and what you need to come in and fix?

Denise Logan:
I come in a couple of different times in a transaction, and you know this in your own life, there’s where we come in and where we should come in, and those are often unrelated. When I come in early, I’m simply part of the process and I’m working with the owner, with their family, with the deal team. Sometimes I come in because we’re in the middle of the process and the owner stopped talking to someone or it’s blown up. That’s a more nuanced introduction. If I come in early, the introduction is selling your business is a tumultuous process. Everyone’s going to be focused on the transaction. Let’s make sure there’s someone who’s focused on the transition. If we’re in the middle of a deal and things are ratty, that’s a more nuanced introduction because no one wants to feel like they were naughty and just got sent to the guidance counselor’s office. Or sometimes I come in very late, maybe even after the deal has happened, and the owner is struggling with the time of either their earnout or they’re in depression after they have exited their business because they weren’t fully ready for it and they feel like they are lost. One of the things that happens, and you may have heard it, where an owner will start to fight with you with your fee at the very end of the transaction. They’ll do it with the lawyers, they’ll deal with the bankers. What’s actually happening is a form of separation anxiety. So for the owner, they have had intense connection with you for months and months. And the closer they get to the end, the more they realize, “Hey, Craig’s not going to be calling me. We’re not going golfing anymore.” And they start to feel, excuse me, they start to feel alone, the loneliness of leaving their business. And I don’t know how old your kids are. Do you have any that are off to college yet?

Craig Castelli:
No, they’re middle schoolers, so I got some time.

Denise Logan:
Okay. So you’ve got some time, but for those who are listening, there’s this thing that happens. It’s called spoiling the nest. It’s a psychological process of separating. So as our kids reach high school and then they graduate, in that summer before they go away to college, they’re little jerks. Oh my gosh, when it comes time to take them to college, they’re like, “I’m not coming home for Thanksgiving.” And as you’re pushing them out of the car, you’re like, “Good, don’t come home for Thanksgiving.” And what is happening is they are attempting the separation in a place of anger instead of connection because it’s easier. So near the end of a transaction, when an owner starts fighting about their fee with their lawyer or their banker, I’m often in that, “Oh, you know what? They’re going to miss you. They’re going to miss you and they don’t know how to say that. And so instead, they’re shoving you away.” And the way to do that in many ways is around fees. When we address that early on in the process, we can avoid that happening later. And we make it safe for the owner to say things like, “Yes, this has been tough and I’m going to miss you.” And as professionals, we also then don’t just drop them. We come to the end of a deal, the deal is over, and you’re onto the next deal. For the owner, they are not having any contact with anyone anymore or dramatically reduced. And so when we do a slower off-ramp, and often I’m that person who’s slower off-ramps with them so that they land safely on the other side of their transaction into a transition where their life is good.

Craig Castelli:
That’s really interesting because I always viewed it as one last act of exerting their power. This is the final thing they can control before they’ve given up control of quote unquote everything.

Denise Logan:
Yeah. In most instances, that is a pushaway because they’re realizing not only am I separating from you, but I’m also separating from my business. And I might not be able to push against the buyer or against anyone else, but there’s an interesting place of safety to push against you. That makes sense. It doesn’t feel like that in the moment for sure. Absolutely not. It does not feel like safety or like I’m going to miss you. It feels like, why are you being a jerk? Again, we come back to the fear. What they’re doing is pushing. That’s an anger form and anger is actually driven by fear.

Craig Castelli:
So I want to ask you about one more concept I had in my notes here, which I think I know what this refers to, but I want to hear you describe one more year syndrome.

Denise Logan:
Oh my gosh. I call it oh my syndrome because it stands for one more year. Oh my. And often what is happening when an owner says, “You know what? I just need one more year,” or they’ll say, “Three more years.” What they’re signaling there is there is an emotional piece that I don’t know how to tackle yet. And I might not even know it’s emotional, but there’s something, some friction here. And if I kick it out one more year, maybe it will have resolved itself by then. That thing I don’t know how to tackle will have solved itself. So maybe I’ll have friends in one year. Maybe I’ll know how to let go in one more year. So when I hear one more year, or even sometimes it’ll be three years, but when I hear that signaling, it tells me there’s something emotionally that this person doesn’t know how to tackle. And therefore they’re kicking it down the road in hopes that it resolves. A lot of the things that are going on under the surface in a transaction are things that are just unpredictable. I was involved in a transaction in Denver very close to the end. Some chaos started churning up in the deal. And I said to the deal team, “Oh yeah, this is not his. This is coming from home.” Because at work, he’s a bully. He is always involved in conflict with someone. And mama just realized the bully is going to be home full-time with her, and she is scrambling behind the scenes to try to unravel this so he’s not home. So I did some individual work with her, but then I got him involved in a boxing program, ostensibly for his physical fitness and his social needs, which were definitely true. But there was an unarticulated need that was getting met by him by being a bully. That was not going away no matter how much money he got. And once he locked onto that boxing program, all of her chaos settled down, the deal closed smoothly, and the transition of the business was much more gentle than it would otherwise have been because he had a place to bully. And that was not a need that he was able to identify. That was a need that I could see was happening. And not everyone wants to acknowledge all the things they’re getting from work. Do I think being a bully is an acceptable need to get met at work? Not for me, but if it’s happening, we need to figure out how do we address those things so a person lands safely on the other side of their process?

Craig Castelli:
Sure. Well, I think you answered the question of when we should call you. I think it should be anytime a business owner tells us, “Call me in a year. I need one more year and then I’ll be ready.”

Denise Logan:
Right? What is really happening there? And it’s funny, when people hear what I do, they often will say, “I wish I knew you three months ago,” and they will tell me about a deal that unraveled. And I always say, “Well, there’s good news and there’s bad news.” The good news is you know me now. The bad news is you’re going to want to know me again.

Craig Castelli:
I love that. I love that. Well, Denise, this has been a ton of fun. I could talk to you all day, but we have to end at some point. So for those listening who want to get in touch with you, read your book, learn more, where should they go?

Denise Logan:
Thanks. My website is deniselogan.com. The book is called The Seller’s Journey, and it’s a business fable. It’s the story of an owner one year after he exits his business. He goes on a trip across Glacier National Park with his banker, his lawyer, his wealth manager, and the buyer who bought his company. Right now you might be thinking it’s a murder mystery, but it’s actually designed to help owners see how important it is to choose the right team so that they land safely on the other side. It’s been my pleasure to be with you, Craig. Thanks for having me.

Craig Castelli:
The pleasure is mine. Thanks for joining, and thanks all of you for watching us on The Close.