Aug. 12, 2025
EP 11 | What Happens After You Sign the Papers?
Why do so many business sales collapse at the last minute? It’s not the money, it’s the emotions. In this episode, “Seller Whisperer” Denise Logan, both a therapist and attorney, shares the hidden psychological traps that quietly kill deals. From fear-driven reactions like fight, flight, or freeze to the identity crisis that follows a sale, she reveals why selling a business is one of the most emotionally charged transitions an entrepreneur will ever face. Packed with powerful stories, practi...
Why do so many business sales collapse at the last minute? It’s not the money, it’s the emotions.
In this episode, “Seller Whisperer” Denise Logan, both a therapist and attorney, shares the hidden psychological traps that quietly kill deals. From fear-driven reactions like fight, flight, or freeze to the identity crisis that follows a sale, she reveals why selling a business is one of the most emotionally charged transitions an entrepreneur will ever face.
Packed with powerful stories, practical insights, and her unforgettable “marbles in a jar” metaphor, Denise shows how addressing the human side of the deal can save it from falling apart.
Press play to uncover the emotional blind spots that could make or break your business exit.
00:00 - The High Stakes World of M&A
09:15 - Meet the Seller Whisperer
14:48 - What Work Provides Beyond Money
25:35 - Fear Responses in Business Transactions
36:40 - Attachment Theory and Business Exits
50:30 - Finding Identity After the Sale
01:06:08 - The Marbles in the Jar Story
WEBVTT
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In the world of business, not all deals are what they seem.
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Fortunes rise, empires crumble, all with the stroke of a pen Mergers, acquisitions, hostile takeovers.
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Welcome to Mergers, she Wrote, where we examine strategies and stories behind the biggest deals in business, because in M&A, the real risks are the ones you don't take.
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Welcome back to Merger, she Wrote.
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On today's episode, we are going to talk about probably the most difficult aspect of selling a business, which is emotionally getting on board with letting go of something that you've worked all your life to build.
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I'm Paloma Goggins, your host and owner of Nocturne Illegal, and I am pleased to tell you that I have Denise Logan today as my guest.
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Denise, thank you so much for being on today.
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I'm so glad to be with you, paloma, so I want to just jump right in in that you are the self-proclaimed seller whisperer.
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Tell us more about what that means.
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I might give you a little background about how it came to be.
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Does that make sense?
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Yes, that's totally fine.
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So in my early life I was a therapist and then I was a lawyer, and right now you're wondering why I didn't use those good therapy skills to keep myself from becoming a lawyer.
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One of the things that I saw was that business transactions were unraveling for all the reasons that were not what was being said.
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Business owners would ask for more money or focus on a transactional element, and I realized that's not what's going on Under the surface.
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They're afraid to leave.
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So I built my law practice.
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When we reached 50 lawyers and 300 support staff, I exited my own practice, and so I was them in many ways.
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I took off, got rid of my, my house and bought a motor home that could be a whole conversation of another episode.
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I thought I was going to travel for six months and it turned into almost five years.
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It's incredible.
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And so for the last 16 years, I've worked one-on-one with business owners and their advisors to navigate the emotional arc of letting go of their business.
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Do you pull from your personal experience about letting go, or was it for you when you sold your law practice?
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Was it time for you when you got to that sale?
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Because I know that for some sellers, especially coming from the legal side, right they're just ready.
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And so when you advise your clients about letting go, do you pull from some of your own experiences as well?
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For sure my own and the experiences that I've had with clients.
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So it's interesting because you kind of had a question tied in there was I ready?
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The truth is that I was ready long before I actually let go, so I knew I was done practicing long and had actually engaged some consultants to help me figure out how to exit, and they were completely focused on the transaction.
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So several of them said things like you're just burned out, like why don't you buy a sailboat or go on a vacation?
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And if you really double down and you just do the next five years, you could have something so much bigger.
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And that felt like a horror to me.
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I think one of the things that I see in transactions a lot is that the professionals are giving great professional advice, but it's almost as if they've forgotten there's a person involved in the process.
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So when the time came for me to exit my business, I was ready, but I probably wasn't ready.
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So an example is after I left, I remember being on my patio having tea, reading a magazine and thinking, ah, this is what I've been after.
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And then I started thinking about a client and part of me was like, oh, I should call.
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Oh wait, that's not mine anymore, and the emotional part that came up for me was oh, I got what I wanted.
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Oh, no, I got what I wanted.
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Was that what I wanted?
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I think I got what I wanted.
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What I see for business owners is that's often what they are facing, but the people around them, like the people who are around me at that time, would say things like but I thought you wanted to sell and the answer is yes and I think this idea of wanting to sell but not necessarily knowing what it looks like beyond the sale, or this ideology of what it looks like beyond the sale, or this ideology of what it's going to look like.
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And then you get there and it's boring.
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Or maybe it's not boring, maybe it's the relaxation you've wanted, but you're still, like you said, attached to the ownership of that business.
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For sure, when working with and I want to wrap this conversation into your book, because I read the book and I thoroughly enjoyed it oh, you're so sweet thanks.
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When you're working with clients who are in the process of of exiting or even succession planning, you know, are there themes that you see that recur among those clients that you have to work through?
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Or is every person's journey so unique that it's almost like solving a unique puzzle every time?
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Let's start with the basics.
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We will all leave our businesses one day, voluntarily or involuntarily, so true.
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Businesses one day, voluntarily or involuntarily, so true.
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And often, when I first meet an owner, they will say, well, if I leave my business?
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And I would say, oh honey, that word is when, not if, because we will all leave our businesses.
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I think one of the things that I often see is that owners think they will know when that it will just occur to them.
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While we have a transaction that's going on in the sale of a business, there is also a transition that is happening for our owners.
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In no other part of our life do we go through transition alone.
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If you think about it, when the last child leaves home, what do we call it?
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Empty nesting.
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Empty nesting and we have a phrase for it and we all know what it is, so that when you drop that child off at college and you come home and you're setting the dinner table and you have four plates when you should actually only have three plates, and it feels emotional four plates when you should actually only have three plates and it feels emotional.
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No one is shaming you, no one is saying but I thought that's what you wanted.
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Yes, of course you wanted that kid out of your house by then.
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And that's a transition.
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Even if we look at something basic like that, we are going through it with other people.
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So typically, when our children leave home, we go through it with the other parents of our children's friends or our family knows what that is and we recognize it.
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For our business owner, this transition is the single greatest emotional transition that they are going through in their adult professional life, and they're often going through it alone, and some of that is because the professionals around them rightfully so are focused on the transaction.
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So the attorney is focused on her part, and the CPA is focused on her part, and the investment banker is focused on his part, and everyone is focused on what makes sense.
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Can I give you the story of an owner that might put that into context?
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Of course, so we often think about it in terms of older owners, but younger owners face a lot of this too.
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So we had a younger owner who was exiting his business.
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He was 36 years old.
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He was set to earn $16 million on the other side of the sale.
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That's a pretty good chunk for that point in his life and he suddenly realized who am I going to hang out with?
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All my buddies have jobs.
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Unfortunately, we had a low EQ investment banker in that transaction who said dude, you can buy friends.
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I was like, oh no, that was in your outside voice where we could hear it.
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Our owner was struggling with a loss of something.
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So often the professionals are focused on the economics of what the owner is getting.
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So one of the questions I like to ask owners early on in the process is what does work provide for you other than money and financial security?
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Because guess what?
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You're not exiting your business unless you're getting money and financial security so we can check that's for sure happening.
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And financial security, so we can check that's for sure happening.
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And I'll ask them to list 15 unique things that they are getting from work other than money and financial security.
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Typically, when I ask that question, they will say well, like what, what else is there?
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And so want to play a game.
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Paloma Sure.
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This will be fun and for you, for your listeners, think about this as we go through it.
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Okay, what else do you get from your work other than money and financial security?
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What one thing pops in your head?
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Well, I think we have a lot in common um from a background standpoint in that, and I don't know if I've shared this yet on the podcast, but I originally wanted to be a psychologist.
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More specifically, I wanted to be a professor of psychology with a private practice on the side.
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Wow, that was like the vision.
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Um, I went in college.
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I went to a lab to fulfill sort of the requirements prior to applying for the PhD program and determined that I despised the laboratory aspects of psychology.
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I really liked the therapy version of it and I didn't have anyone in my family that was in that realm.
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So no one said well, paloma, you should just go get a PsyD, or you know, an MS, you know, just go and get something that you can do therapy and not the research side of psychology and so I pivoted to law school.
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One of the things that I love about working with business owners, and specifically in the merger and acquisition space, is that I help people work through their problems when it comes to negotiating and getting them comfortable with the terms of the deal, and so it's very it's not quite the uh, sit down on the couch and have a conversation about your relationships and work through it, but it's still a version of that, and so for me, besides money and stability in terms of what work provides me, I think, is a lot of a sense of fulfillment when I help people kind of demystify the legal world.
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For sure, and some of the things that I often hear from owners are structure.
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Right Work provides structure to our day to our week to our year.
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It also provides a place to go Right.
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During COVID, weren't we all desperate to get out of our houses and PS?
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our spouses were desperate for us to get out of the house too.
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So it's a place to go.
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It's also things like intellectual stimulation.
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It's friendship for lots of our owners, their business, their employees, their customers, sometimes even their competitors, are their friends.
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Then we start getting into some of the deeper things that are harder for us to acknowledge.
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That work provides for us, like power At work, I say I want something done.
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It generally happens Not so much in my house.
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The people who live in my house don't always think that they should do what I want.
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Or often, as business owners, we are the wisdom keepers.
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We are the ones that people turn to to ask the questions.
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It's also things like we can be the thrill of the kill, the thrill of the chase.
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I get to close that deal, I close that new acquisition, whatever those things are that our owners are getting, and they're unique to people.
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But there is some structure to it.
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Those things don't go away just because we get a big sack of cash, and so often the people around us are focused on the sack of cash, rightfully so.
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We need to make the transaction happen For our owners.
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Often, as they are getting close to the end, is when they realize oh, who are my friends?
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I don't have any Saturday friends, or who's going to pay attention to me, who's going to follow my direction?
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I'll give you an example of a client that I worked with.
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We were very close to the end of the transaction and some crazy started stirring up and I said to the deal team oh, that's not from him, that's from home At work.
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He was a bully, and no judgment about that.
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It's not how I like to work in my business, but he was often engaged in litigation with former employees or vendors and I think his wife suddenly realized the bully is going to be at home, and so the chaos that started showing up in the transaction was actually because of things right, our partners are involved in this transaction.
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It's affecting them as well.
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So once I sorted out what was happening, I got him involved in a boxing program, which, for him, was for his physical fitness and his social needs, because that was going to be a big change.
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But it also gave him a place to get a need met.
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It isn't a need that we all need, but it was something he definitely needed.
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He needed to have a place where he was going to get to pound on people and while at work he wasn't physically pounding on them.
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He needed to have that release.
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Once we got that taken care of, all the chaos at home settled down because mama realized oh, the bully's got a place to go.
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So often what I see is that because the professionals in the transaction are only talking about transaction, when something comes up for an owner that is actually an emotional need, they will frame it as a financial need.
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So another example $85 million transaction.
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Eight weeks before closing the seller suddenly announced he would not take a penny less than nine times EBITDA, which is great, except his deal was at 6.2.
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So we had a pretty big delta and he stopped talking to everyone.
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The investment banker called me and said I think my seller went crazy.
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I'm like, yeah, sounds like it.
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Let's see if we can figure out what scared him and what hidey hole he went into.
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So his original plan was to sell the business, buy a sailboat, sail around the globe.
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You can get a pretty good boat for $85 million.
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So it probably was not really about the money, right?
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And then I learned that two weeks before he asked for this financial unicorn, his wife had said I'm not doing that.
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I do not want to be stuck on a boat with you far away from my grandkids Hell, no, this ain't happening.
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Can we agree?
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He's not coming back to tell the deal team the deal is off because his wife won't let him do what he wants to do.
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Instead, he asked for something that he knew he couldn't get, so that the deal would fall apart and it would not reflect on him.
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So once I figured out what was happening there, we created a solution where he would buy the sailboat and sail and every six weeks his wife would take one grandchild fly to where he was.
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They would do two weeks on land building memories with the grandchild.
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Then she would fly home and he would sail on Boom.
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Our deal was back on track, closed on time at its original asking price, because it was never about what it looked like, it was about Interesting.
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I'm sure you see that in your own practice.
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Definitely.
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But to your point, I think there are times when none of the team is equipped to handle, when someone has panicked and hit the I quit button.
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And you know, to your point, I don't think every seller is sophisticated enough about their own emotional intelligence to recognize when they're self-sabotaging or when it is really about something that matters to them.
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And I try, you know, and I think that your book and the conversations we've had has opened my eyes to ways that I could maybe rely a little bit more on some of the base knowledge I have from going through my undergrad degree and just living life, yeah, Even just in living life, when we pull away from the transaction and we just come back to what might be happening for this person.
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I talk about something that is about dealing with the context rather than the content.
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Can I get a little of that?
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You know the argument that you have with your spouse about why you didn't put the mustard on the right shelf in the refrigerator, or whatever your variation is.
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Right now.
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Your listeners are probably like oh yeah, I know what that argument is.
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Can we all agree?
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It's not about the mustard, ever, ever.
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But we continue to argue about the mustard and then the underlying issue doesn't get solved.
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So in many ways, that's exactly what's going on for our owners.
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Something comes up and we start dealing with what they've, almost like the red herring that they have drawn across the trail.
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And it's not about that.
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It's about pausing the content.
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So instead of continuing to talk about, let's say, the negotiation that's happening, to be able to be self-aware on our own part and on behalf of our client, to recognize, oh, she just got scared, let's pause for a minute, deal with what happened, what frightened our client.
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Then, once we address what that is, we can come back to what we're trying to negotiate, but often, I think what happens is sometimes the professionals either aren't equipped with it what to do in that instance or they're just intent on plowing forward anyway.
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That's what we see, we will hear in this industry that time kills all deals, which is so wrong.
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What kills deals is unprocessed emotion so often.
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Do you know the children's game Chutes and Ladders?
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Yes, so I grew up in Canada where it's called Snakes and Ladders.
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I don't know who thought that was a better way to call that game.
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It seems scarier to hit a snake than a slide.
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So we might stay with the American version of it.
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So, if you think about it, you spin the dial or roll the dice and you move your little marker, and you might move it three or four marks and then you hit a ladder and you're thinking, woo-hoo, I'm going to win this game.
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And then two rolls later you hit a shoot and zoom, you're back down on the board.
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If you think about, emotionally, what's happening for a child when they're playing that game, they are discouraged, they're disappointed and if we don't address that disappointment and discouragement, they will flip the board.
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For our owner, the exact same thing is happening.
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So we know, as deal professionals, that, like they're saying, every deal dies, seven deaths.
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Right, there is this.
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We know it's up and down For our owner this is the one and only time that they are going through this.
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So it is incumbent upon us as professionals just like we would with a child playing this game to help them to realize what's happening, to emotionally resettle so that they can take the next step Instead.
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I think often and I'm just going to point the finger at investment bankers for the moment because of how they are compensated, often they only get paid if the deal closes.
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So imagine what's happening emotionally for the investment banker when it looks like the deal is about to fall apart.
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Their fear is up and driving what happens so often.
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When I'm involved in a transaction I'll say to the banker don't shove your client, shove me, you can shove me.
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Let's get all that anger out, the fear that you're worried.
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Your commission is just about to evaporate.
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Let's deal with that, Because if we don't, what happens is the investment banker then starts shoving the owner.
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And we all know when someone's shoving me, I don't like it, I'm going to shove back or I'm going to leave the game.
00:22:12.868 --> 00:22:27.980
That's why when I hear someone say time kills all deals, I'm like, oh, that's the most scared person in the room right now, because they're the person who's afraid if I don't make this happen, it's all going to fall apart.
00:22:29.223 --> 00:23:09.061
I want to go back to something you had said earlier about you know being both having worked in deals like seeing kind of different sides of the coin right and, and being um on the law side, um, you know being kind of the I always call it like the uh, the technician of the the documents right, and so, to your point, when fear becomes all-encompassing, um and it doesn't necessarily break the deal down, but it becomes this wall through which clients cannot they become frozen right.
00:23:10.744 --> 00:23:23.830
One of the things that I see frequently in my practice and perhaps it's the way that I communicate with my clients is they will try and abdicate decision-making to me, and I'm sure you've had that situation even in your position.
00:23:24.272 --> 00:23:31.520
But it's so hard because I understand wholeheartedly where they're coming from in that you know you're the expert, paloma.
00:23:31.520 --> 00:23:38.125
Go ahead, you tell us what's the right move, what gives us the least amount of liability, how do you think it's best to protect us?
00:23:38.125 --> 00:23:54.028
And I always have to bring them back down and say I'm going to tell you the pros and cons, but at the end of the day, you have to be the one that makes the decision no different than probably the decisions that you're bringing your clients to ultimately make on their own fruition.
00:23:54.028 --> 00:24:11.087
But it's a very challenging conversation to have because a lot of times when those clients decide they want to abdicate the decision-making to me and I refuse, they feel that they are not getting the advice or counsel that they signed up for.
00:24:11.087 --> 00:24:21.063
And it's interesting because I always have to remind them a good lawyer isn't going to make decisions for you and they're not going to tell you right from wrong.
00:24:21.063 --> 00:24:26.076
They're going to just give you an educational overview, right?
00:24:26.218 --> 00:24:32.652
of everything and allow you to make a very thoughtful decision about what's best for you personally.
00:24:32.692 --> 00:24:34.762
We can't know what someone else's risk.
00:24:34.823 --> 00:24:36.045
Tolerance is no no.
00:24:36.286 --> 00:24:42.827
But I also watch something that happens in a lot of transactions, since we're both trained as lawyers.
00:24:42.827 --> 00:24:52.689
I call it the parade of horribles that we're going to lay out and this could happen, and this could happen, and this could happen and this could happen, and our client is terrified from that.
00:24:52.689 --> 00:25:00.599
Often that parade of horribles that I watch lawyers do in a transaction is because the lawyer is so afraid.
00:25:00.599 --> 00:25:10.046
If I don't point out every single thing and protect you on all of these fronts when something goes wrong, you'll blame me.
00:25:10.046 --> 00:25:40.357
So in those instances and, as you might imagine, I'm sure you've been in transactions like this where the lawyers are fighting about stuff that isn't actually what our clients are fighting about, we're busy protecting our client and taking on a role that isn't actually what it's meant to be, and so in some of those instances I might work with an attorney to help them figure out what are you afraid of right now and how do we address that.
00:25:40.357 --> 00:25:42.403
Sometimes it's as simple as having.
00:25:42.403 --> 00:25:51.593
I had this happen in a situation and where I had the attorneys recognize I'm afraid you're going to blame me if I didn't capture everything.
00:25:51.593 --> 00:25:55.560
And what if we just have that conversation with our client?
00:25:55.560 --> 00:26:01.559
Typically our clients are like well, I know you can't know everything that could go right or wrong.
00:26:01.559 --> 00:26:08.698
What I often see is that an attorney might not want to have that conversation with their client because they want to look invincible.
00:26:08.698 --> 00:26:13.301
They want to be in the place of I can see all the things and I can protect you.
00:26:13.301 --> 00:26:27.604
What I see in a lot of situations is that it's just about coming back to the humanity of what is going on in the room, and being vulnerable is a misused word.
00:26:27.604 --> 00:26:35.019
I think a lot in our society that it's not about emotionally dumping, it's about really being present with what's going on.
00:26:35.019 --> 00:26:43.883
Can I talk a little bit about fear and how it shows up, kind of the neuropsychobiology of what is going on in our bodies.
00:26:43.883 --> 00:26:49.817
So I use my hand as a descriptor for it.
00:26:49.817 --> 00:26:52.461
So fear shows up.
00:26:52.461 --> 00:26:55.530
You know, let's talk about what goes on in our body.
00:26:55.530 --> 00:27:02.442
Inside our brain is a part called the amygdala and the amygdala is the fear sensor.
00:27:02.442 --> 00:27:15.336
It's the oldest part of our brain, also called the lizard brain, and so the lizard is always scanning the environment looking for danger, which is what we were just talking about.
00:27:15.336 --> 00:27:26.375
But it's a helpful part, but it's also kind of a stupid part because it can't always tell real danger from perceived danger, which is what we're talking about.
00:27:26.375 --> 00:27:29.338
And so the amygdala, do this with me.
00:27:29.338 --> 00:27:34.376
Take your hand, wrap your thumb across your palm and bring your fingers over the front.
00:27:34.376 --> 00:27:40.718
We've made kind of a visual representation of our brain, so the amygdala is safely tucked in.
00:27:40.718 --> 00:27:45.435
This part over the front of your fingers is called the prefrontal cortex.
00:27:45.435 --> 00:27:48.042
It's the thinking part of our brain.
00:27:48.042 --> 00:27:50.108
So play along at home.
00:27:50.108 --> 00:27:56.884
If you're watching Now, paloma, when you move your thumb inside the fist, what do you notice?
00:27:58.450 --> 00:28:02.057
It's restricted, right, it doesn't really move.
00:28:02.057 --> 00:28:17.480
Now, if you move your thumb more aggressively, which is what's happening when the amygdala is getting triggered if it moves aggressively enough, you will flip your lid, which we see happening in our transactions.
00:28:17.480 --> 00:28:28.019
We see it just happening in our life that you're talking to someone and all of a sudden you're like what just happened Literally, the amygdala has flipped our lid.
00:28:28.019 --> 00:28:38.625
And so all day long in our daily lives, all of us are walking around in variations of fully tucked in to fully wigged out.
00:28:38.625 --> 00:28:44.701
You know, driving over here, I certainly had an opportunity to flip my lid if I chose to.
00:28:44.701 --> 00:28:45.623
It's not?
00:28:45.663 --> 00:28:46.344
hard in Phoenix.
00:28:46.744 --> 00:28:50.732
And we just see that in transactions over and over.
00:28:50.732 --> 00:28:58.374
And you know you can't make any progress if you're talking to someone who I call it all lizard all the time.
00:28:58.374 --> 00:29:04.631
Right, if the lizard has taken over, we have no prefrontal cortex online, we have no brain power.
00:29:04.631 --> 00:29:11.064
The only way to bring the prefrontal cortex back online is to calm our bodies.
00:29:11.064 --> 00:29:20.675
So this is why I'm talking about pausing the content so that we can deal with what happened under the surface and a lot of that.
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