Episode 8: Navigating Transitions: Insights on Seller's Remorse with Paul Cronin

About the Episode:

The "Now What?" of Selling: Dealing with Seller’s Remorse

Selling your business is supposed to be the victory lap, right? You put in the years, survived the "messy middle," and finally crossed the finish line. But for a lot of us, once the ink dries on that contract, a weird thing happens. Instead of popping champagne, we find ourselves staring at the wall, wondering why we feel so... off.

I was recently talking with Paul Cronin, a guy who’s been through the corporate meat grinder and come out the other side about this very thing. We call it "seller's remorse," but it's really about something much deeper than money. It's about losing your place in the world.

The Moment the Music Stops

Paul shared a story that hit home. He was climbing that corporate ladder, doing the "important" travel, and hitting the numbers, but his life was falling apart at the seams. It took an ultimatum from his wife for him to realize he wasn't actually in control of his life; his title was.

Have you ever had that epiphany? That moment where you realize you’re successful on paper but totally ineffective at being you?

Who Are You Without the Title?

This is where it gets uncomfortable. We spent thirty years being "The Boss" or "The Founder." Then, overnight, you’re just a guy or gal at the coffee shop with a lot of free time.

Paul described it as becoming a "non-person" almost instantly. I’ve felt that too. If I’m not the "business guy" anymore, what am I? Most of the folks you’ll deal with during a sale the brokers, the bankers, they only care about the EBITDA and the payout. They don’t tell you that your identity is often the hidden cost of the transaction.

Finding the "Why" Behind the Exit

Paul has a killer question he asks people who are thinking about hanging it up: "When you think about selling your business, can you tell me what you're really trying to accomplish?"

It’s a simple question, but man, it’s hard to answer. Are you running away from the stress, or are you running toward something that actually matters?

Purpose vs. Meaning

One thing we chewed on is the difference between purpose and meaning.

Purpose is usually about what you do your activities and your goals.

Meaning is about who you do it with your connections and your community.

When you sell, you don't just lose a job; you lose a community. If you don't have a plan to replace those connections, you’re going to end up in a world of hurt, no matter how big the check was.

What’s Your Next Act?

Reinvention isn't some midlife crisis cliché; for those of us in the third act of life, it's a flat-out necessity. We have "way less life going forward" than we have behind us, so why spend it feeling like a ghost?

If you’re sitting there thinking about an exit, or if you’ve already sold and feel like you’re drifting, I’d love to hear from you. Are you clear on what you’re trying to accomplish next, or are you just hoping the "remorse" part skips over you?

Transcription:
Introduction (Josh) Welcome to the Long Strange Trip. I'm Josh. the host of the show.   We're going to dig into six areas together, finding real work-life integration. Instead of that brutal 9 to 5 5 split too many business owners to live with.   We're going to approach retirement as an actual reinvention. Rather than just stopping work.   and we're facing death honestly, and avoiding PTSD around it.   We're also building resilience, when life throws us curve balls.   We're sharing wisdom across generations.  And finally, we're understanding the patterns that show up in all our transitions.  I'm  not coming at this as an expert I'm a fellow traveler figuring this stuff out in real time.  Especially now as I navigate my own dual cancer diagnosis at 73.  Welcome to the Long Strange Trip. I'm glad you're here. Josh Patrick (00:01.026) Hey, how are you today? This is Josh Patrick and we're with Paul Cronin from Touchstone Advisors. And you are at the Long Strange Trip podcast where we talk about a variety of topics. But today we're going to talk about transitions and we're going to talk about sellers remorse because Paul as a business advisor has sold lots of businesses and he's gone through tons of transitions himself. as well as watching and experiencing Sellers Remorse along the way. Sellers Remorse, by the way, is part of our project when we're talking about retirement reinvention and going through tons of transitions is our subset of transitions. So let's bring Paul on and we'll start the conversation. Hey, Paul, how are you today? Paul Cronin (00:50.61) Great, Josh, how are you? Josh Patrick (00:52.266) I'm doing well. Thank you so much for joining me today. So you've been through a bunch of transitions yourself. So let's talk about a couple of them and you can get to choose which one you'd like to start with. Paul Cronin (01:00.54) Yes. Paul Cronin (01:06.056) Sure, I'll actually go back to my corporate days. So I joined a company right out of college. And, um, what I guess kind of just climbed the ladder, right? You know, every year I got a little raise and a bonus and over time I got promotions and, um, I got to a certain point where I was traveling quite extensively, probably three, four days a week, you know, 45 weeks a year. And I was a sales management role and our company was growing very rapidly and it was all going what I thought swimmingly well. And I had two young children at home. And we went, my wife and I went out to dinner one night and she kind of gave me an ultimatum. And she said, I can't keep doing this. I've got a full-time job. This is too much. Like you got to figure this out. Right. Or, you know, bad things are going to happen. I actually spent the weekend in bed. It's true story. I was so traumatized, but it was the epiphany I needed. Right? Clearly, you know, it's not the kind of life I wanted. And I sort of marched into my boss's office the next week and I'm like, Hey, this is what's happening. We got to fix this. And he's like, don't quit. We'll fix this. and we did. but that was really step one and step two, it was the, I, the idea that I needed to really get control of my life and working at the corporation was never going to allow that to happen. we were in a process of an exit anyway, the company, and I had decided that that really wasn't the path for me. So I started my first venture out there raising money. were build a data analytics engine. and I had that similar sort of experience in different ways. They're from, I didn't have to sleep. I didn't sleep in bed all weekend ever again. I love, or in a depressed state, let's put it that way. Josh Patrick (03:06.286) I'm Yeah. So that transition was kind of forced by your wife. I correct in that? Paul Cronin (03:15.836) That's correct. Josh Patrick (03:17.934) And in our sort of model transitions, which may or may not be the right one to use, is that you go through anticipation, which you had none of because you were kind of blindsided. Then you have ending, which was sort of abrupt in the fact that you had to find a way to end. And then you go into what we call passage or the messy middle. So talk about that part of the transition that you went through with that job. Paul Cronin (03:48.861) Yeah, so was great. So obviously didn't quit right away. And I was able to sort of work out hiring somebody to take on some of the work I had been doing remotely. was actually flying to another facility to oversee a team of inside sales folks. So I hired somebody to take on that role. that cut like 50 % of my travel overnight, which was great. And then sort of the step down from there was I started to see that I needed to, that wasn't enough. were, there were other, you know, I still wasn't happy, so to speak. Right. And there were other things I wanted to accomplish and being a relatively young man at that time, I think I was around 40. Um, I had this sort of entrepreneurial itch. Um, but at the same time, um, I really loved the people I work with. Right. And that was hard. to sort of say goodbye to some of these people. And I wasn't sort of leaving the company right away, but certainly towards the end, that was really hard. I mean, leaving the people and the customers were fine. The new venture that I was sort of putting together at that time would have worked with many of those same customers, either retail store owners, but not selling their product, supplying a data analytics service for helping them. So, but the people I work with day to day, people I've known for a couple of decades, I wasn't going to be working with them anymore. You know, I wasn't going to the office anymore. So I had another, if you will, identity crisis from that side. you're going to laugh, but I can remember one day I'm like sitting in my little office here in my house. And at that point I was used to sort of like You get up in the morning, you do your thing, you work out your exercise, you get in the car, and you go to the office, right? Like, this is it. This is my safe place. Or if I was going flying somewhere, I'd go to the airport. And I wasn't doing that. So I would make up these excuses to like, I'm going to stop by the office to talk to so-and-so about something. There was no reason. I could have picked up the phone. But I needed to go to the office. And I did that a few times. Paul Cronin (06:13.432) and the people were very nice and it was very small company but they were like, can we just do this by phone next time? And I was sort of like, okay, got it. Josh Patrick (06:21.358) you Josh Patrick (06:27.022) It's amazing when you leave an organization or a career or an industry how you become a non-person almost overnight. Can you talk a little bit about that? Paul Cronin (06:40.476) Yeah, that is so true. There's a story I'll share. I'll step away from myself for a moment. A gentleman, I was listening to him and he built a very successful software company, like sold it for, I think, eight digits. And he sold it to one of those 10 digit companies, right? And he said, he had this one coffee shop he liked to go to because he lived near where he worked. He said, one day it occurred to me that number one, I wasn't sending somebody to the coffee shop for my coffee. And instead I was there. And so he said, I went from in my mind, I went from CEO to seventh in line at the coffee shop. The whole room, of course, roared, right? And it's so true. Josh Patrick (07:37.262) Yeah, I mean, once you sell your business, and this is a big thing for business owners, and we talk about a lot. I've written about it probably too much is that if I'm no longer a business owner, who am I? Paul Cronin (07:50.842) It's huge. It really is. Josh Patrick (07:51.993) You know, that's in and too many people in your business, Paul's in the &A business. He helps people buy and sell businesses, mostly sell, I think. And most brokers or investment bankers or whatever level you want to talk about, they want to get a deal done so they can get paid. And they know what's going to come for their their Paul Cronin (08:16.092) Bink up. Josh Patrick (08:21.73) a business owner seller because they've been through it a zillion times before, but they never talk about it with the seller. And I think that's malpractice, frankly. Paul Cronin (08:36.712) It is. And I get where we, we, I are coming from. Most people who do M &A, whether you're a broker or a guy in Goldman Sachs and guys like me who are kind of in the middle market, as it's called, we make 95 % to 99 % of our money at the closing table. That's motivation. You don't want friction, as I call it. Josh Patrick (08:59.074) Yeah. Yeah. Yes. Paul Cronin (09:03.75)
You don't want anyone or anything to interrupt, create friction between that payday. Because hey, I got a house. I got a mortgage too, right? And if you're younger, like you're raising kids, you get kids in college, right? There's a lot more on the line. I'm kind of in the fourth quarter of my career. So not the end, fourth quarter. Still going. I have to remind people of that. There you go. There you go.

Josh Patrick (09:13.698)
Yeah.

Josh Patrick (09:26.83)
I'm past the end of my career, so.

Paul Cronin (09:33.533)
But at any rate, so, but the I and other people still complain like when all of a sudden owners, business owners, our clients, the sellers throw up what we feel are like smoke screens and what's the problem? What's going on here? Why is this thing slowing down? Why are they going to change their mind? And again, it's friction, right? Between us and the closing table and

I know what's going on. It's like, okay, right. We need to have a conversation here. And what I say to people is a question I learned from one of the most brilliant consultants I've ever met, named Paul Lindberg. I asked this simple question with a hard, complicated answer. It says, when you think about selling your business, can you tell me what you're really trying to accomplish?

Josh Patrick (10:31.202)
That's a question.

Paul Cronin (10:33.384)
And what I've learned from that is someone will give you some response like, I'll fund my retirement. said, okay. Well, if you could fund your retirement by selling your business, what would that mean to you? And they have to come up with something else, right? Cause they just said, and they'll might say, well, if I can find my retirement, I can take the trip to Italy. promised my wife 30 years ago.

Or I can finally donate money to my alma mater or fill in the blank. Right. And then when they sit, when they tell you that, or they tell me that I say, wow, that's, that's great. And if you could donate money to your alma mater, what would that mean to you? And you repeat this process with people. And I have this little joke.

Josh Patrick (11:30.722)
Yeah, it is.

Paul Cronin (11:32.604)
They all end up in the same place. World peace.

Josh Patrick (11:34.767)
Which is. Oh, OK. Well, that's sort of, you know, sort of like, you know, when people are, you know, have a certain amount of fear in their life. Tony Robbins calls fear false evidence appearing real. And for the most part, I happen to agree with Tony on that. But but the truth is all the stuff that you were describing are financial issues.

And here's where where I think that business sales fall on their head. And it's why guys like you hate guys like me involved in deals back when I was doing this was I would be probing the seller for the soft reasons they were selling their business, which in my experience are much more important and much more dangerous. So they don't get it right than the financial reasons. Finances are the finances of the finances.

I mean, the business owner knows essentially how much money they're going to get out of the deal way before they even think about bringing in an investment banker because they thought about this constant.

What they haven't thought about constantly, which is where our investigation lies with the law and strange trip, which is entire retirement reinvention, which is who are you and what are you going to be for the next 35, 40 years of your life? And, my belief is, and I've seen this happen a bunch of times and you know, and a people would tell me they don't know why they do. I think.

is I'll get, I would be taking a client through the process of their business. We start talking about the letter of intent and then out of the blue, the owner calls me up and says, you know, I'm not sure about this deal.

Josh Patrick (13:30.176)
And it's got nothing to do with the money. It's got nothing to do with the terms. It's got to do with who they are and what they're going to be. And their buddies who sold their business who continually and constantly complain to them about how bored they are. And they say to themselves, gee, I don't want that happen to me. So do you have a solution for that? I don't, I don't, by the way.

Paul Cronin (13:54.215)
Yeah, it's a fabulous question and it's a hard, complicated answer. So the short answer is people who own businesses, really most of us, all of us, we have to work to support ourselves, right? But we also work to find some sense of purpose in our life.

Josh Patrick (14:17.741)
Yes.

Paul Cronin (14:25.082)
And so how do you replace that sense of purpose? And purpose to me is a combination of what you do and who you're connected to. Like, who do you do that, whatever that is with? All If you think of my story there about like, I had to go to my old office, I didn't work there anymore to like ask a question. No, I didn't. All right. I missed that human connection. Right. So that's part of it.

Josh Patrick (14:48.845)
Yep.

Paul Cronin (14:55.75)
But then there's purpose, and then there's meaning in life. And they're not the same thing, in my opinion. Purpose is more of this outward expression, connection. It's activities. I did a whole blog series on LinkedIn about this, all these different activities, how a framework for purposeful living. But meaning, meaning, I believe, can really only be derived from

Josh Patrick (15:02.005)
No, but not at

Paul Cronin (15:25.542)
The actions you take and the response from others, my life has meaning because of how I'm interacting with, loving other people.

Josh Patrick (15:44.258)
Mm-hmm.

Paul Cronin (15:44.745)
I mean, the movie, it's a wonderful life, right? Just watch it again, which I had, you know, every Christmas had watched in a while. And yes, it's Frank Capra and it's Hollywood and it's all that. But you know what? There's a lot of what it's all about right there.

Josh Patrick (15:50.923)
Okay.

Josh Patrick (15:59.567)
Yes. So here's been my experience is that business owners tend to spend 95 % of their efforts on their business and 5 % of the rest of the life. You know, that vacation to Italy could have easily been accomplished if we expanded that to 10 % for the rest of my life or maybe 15%. And if you've been in business for 30 years and you can't find a way to take 15 % of your life away,

and go on that trip to Italy with your spouse, there's something seriously wrong with your business. And you need to start looking at that. The challenge comes in, and this is something that, you know, we're not going to really talk about today, but it's something I struggle with, which I call the 95-5 owner, which is 95 % of their business and 5 % of their family. And you can get away with that.

Paul Cronin (16:33.842)
Exactly right.

Josh Patrick (16:54.638)
maybe in your 40s and 50s and 60s, but you really shouldn't be getting away with it in your 30s. Because that's when your kids are young and your kids need you around. You need to find a way. And I'm not going to get into that today because frankly, I did a terrible job and I don't know how to do it, but you need somehow to get to 20, 25 % family and 75 % business.

And some people say you need more, but I would say the minimum is 20-25%.

Paul Cronin (17:23.559)
Bye.

Paul Cronin (17:28.806)
I think there's a lot of truth in that, Josh. There really is. It reminds me of this story I heard. So Harvard Business School Professor Colin Christensen, I wrote a number of books. He was a devout Christian. But he and his team, they only worked Monday to Friday. The story was he would lock the office up for the weekend.

And then his boss would say, well, gee, you know, I really need you to come in on Saturday. We've got to do this and that. And he's like, I work 10, 12 hours a week, Monday to Friday. My people do the same thing. He said, know, but what do you need done? He goes, well, I x, y, And he said, well, you know, this Saturday isn't a good one. Maybe we can, I'll squeeze something in next week. So then his boss said,

Well, how about Sunday? And so Colin replied the following, least in the interview, was, well, boss, I can't do that because Saturday is my time for my family. And Sunday is my time for God. And that was the end. Said he never had to have that conversation with his boss again.

Josh Patrick (18:27.415)
Ha

Josh Patrick (18:51.182)
At least his boss was reasonable about that. Some bosses aren't. So going back to, you know, selling a business and the challenge that comes in there, this was the challenge for me. Every time I've gotten out of a business, I've gotten out of several now over my lifetime, my social circle from that business falls away faster than you can possibly believe. I got out of my wealth management business a year ago.

It's almost exactly a year ago, last January. And over the last year, I have had zero phone calls, zero questions from old clients, zero anything from anybody from that industry. Now, if I had not been working on this new project I've got, which came out of the blue, it actually didn't came out of a lunch with a friend of mine, but that's a different story.

And I would be a pretty lonely guy right now. And the challenge that I have, and I think the challenge that a lot of business owners have is your entire social circle is designed around your business. All your friendships are suppliers, coworkers, vendors, know, professional people. Go out to dinner with these folks, have lunch meetings. You think you've got this great relationship. And of course, it's going to last past me selling my business.

I hate to give you the bad news. It's not.

Josh Patrick (20:30.168)
So.

Paul Cronin (20:30.278)
No, it's so true. Yeah, so true.

Josh Patrick (20:32.91)
So the question I have, how do you help people get past that? Because whether it's conscious or subconscious, and I think most of the time it's subconscious, owners get cold feet when they get close to selling the business because they look over the ledge and they just don't like what's sitting there. How do you help them find something they would like that would be sitting there?

Paul Cronin (20:58.12)
Yeah, one of the things, so I'll start the conversation at the early part of the conversations about whether or not they should sell their business. And I have this little exercise and I'm happy to share it with you after the program. And it's a little simple worksheet, all right? Across the top has a question. It is, what can I accomplish by selling my business? Personal goals, business goals, financial goals. I'll give a few examples, all right?

And I asked them to really dig into this. Try to have three in each. I said, the reason you need three in each is nobody gets nine. OK? You'll get some combination of those. But if you don't list them down, and if all you think about is the number, you're going to disappoint them. So that's one thing, to start the process up front. But on the other is to share this frame of purposeful living. And again, I can show you that.

Josh Patrick (21:33.037)
I'm

Paul Cronin (21:54.453)
...the graphic or what looks like, but imagine a pie with 10 slices. And each of the slices represents a portion of your life or a set of activities: physical health, intellectual health, spiritual health, right, activities with family, activities with your spouse or life partner, figuring out where you're going to live, figuring out...

Other income-producing work, how are you going to volunteer? Are you going to donate money? Particularly if you're going to sell a business for tens of millions of dollars, you are going to be hit up by everybody who you don't know yet for money. Right. But then your answer, your question, is how do I create new social connections in my life? And it is — it requires thinking about social connections differently.

Josh Patrick (22:27.529)
You are.

Josh Patrick (22:37.134)
That's the big one.

Paul Cronin (22:44.984)
And one of the questions is outside of work, this is the exercise I have people go through. Outside of work, all right, how do we interact with other people? Outside of work, what do people think of me? So when you do that outside of work, you start connecting to the people that you interact with — that barista at the coffee shop, okay? The pastor at your house of worship, okay?

Josh Patrick (22:50.381)
Yes.

Paul Cronin (23:15.568)
I don't know, the clerk at the corner store. There are some people you interact with — your bartender, if that's your flavor, all right?

And learn and observe and try to understand what those people think of you, what they appreciate you for. Obviously your family, your friends, right? And it's through those people that you'll start to see your importance in some way. And then you can think about activities that can increase that importance. When you do that, you start to create, I know that people think of the social network as, you know, this online stuff,

but we all have some kind of social network. For business owners, it tends to be, as you say, related to their job or their industry or their work. But even if you're not a business owner, a lot of people still do that. Absolutely.

Josh Patrick (24:07.054)
Even senior executives in companies who work 60, 70 hours a week, they have no time for outside activities, really. You know, maybe they'll play some tennis, maybe they'll get a few days of skiing in, maybe they'll, you know, play a little bit of adult hockey or, know, whatever they can come up with. But frankly, the sad thing about that also is

Those relationships go away immediately as soon as you can't play the game anymore. You know, I used to be a very, very avid tennis player. I haven't talked to one of my last. Not sure there’s one ex-tennis buddy I had I have a regular relationship with outside of tennis. One. I used to play with 15 or 20 people on a rotating basis. Same thing with skiing.

Paul Cronin (24:59.506)
Well, here's the thing. If you like to read books, there are book clubs. Right? There you go. Well, I'm going to send you this exercise. You motivated me. You'll like it.

Josh Patrick (25:04.3)
Yeah, there are. And frankly, I need to join one or three.

Josh Patrick (25:11.99)
Yeah, it's it's it's really — I mean the truth is one of the things that's sad for me is I have a large social network. None of them are in Vermont.

That's not true. I think three or four people are in Vermont. But the truth is almost none of them are Vermont. So it's almost impossible for me to have a real relationship. Zoom relationships really don't count.

Paul Cronin (25:39.464)
They're okay. They're better than nothing.

Josh Patrick (25:41.154)
They're nice. They're nice to start with. It's better than nothing, that's for sure. But the truth is...

Men especially appear to me — and this is an appearance and I'm not sure it's completely true — they have a much larger problem with remorse in leaving a career than women do. Women tend to have much larger outside local social networks than men.

Paul Cronin (26:07.612)
I agree.

Paul Cronin (26:14.776)
and deeper networks and deeper relationships in my observation.

Josh Patrick (26:16.148)
and deeper in there. My wife is — I mean, look at my wife's, you know, social network in Vermont. And it's pretty darn big. I look at my sister, my sister's a raging extrovert. I'm a raging introvert. But she's got — I call her the mayor of Burlington because she knows everybody. Anytime I go out, there's someone there she knows. You know, I've been going to the airport now for years, I think three or four times out of 40 years, probably hundreds of flights.

Have I ever seen anybody I know?

Paul Cronin (26:48.808)
Well, you know, part of this exercise that I've been talking about on LinkedIn, this process really, is you can build your social connections — your social network, your social connections — through other activities. So if you were to choose to say, okay, I'm going to volunteer, I don't know, make up, the recycling committee in my community, whatever, okay? You volunteer, the other people all volunteers, it might be some paid person, whatever,

who organizes things and make sure there's coffee. But you but rather like work, right? You would say, Hey, you know, you hungry, you want to get a sandwich? And it's just simple things like that. And then it's like, Oh, you, you like to hike too? I love to hike. Where have you hiked before, whatever it might be, you, oh, you read that book. And, and particularly for men, our relationships...

Josh Patrick (27:31.043)
Yeah.

Josh Patrick (27:39.298)
Yeah. It could be one. Yeah.

Paul Cronin (27:47.257)
...are what I call activity driven. They're action — like I'm doing something, I'm playing a particular sport or I'm going to a game or whatever it may be. And so there's this sort of, if you think of boys, right, we go around, we bump into each other. And I raised daughters, and they happen to be athletes, so they bumped into other girls, but then I also observed their relationships. They had nothing to do with an activity.

Josh Patrick (27:51.182)
AR.

Josh Patrick (27:55.459)
Yeah.

Josh Patrick (28:16.728)
Right. Yeah. It's an interesting thing. And I'm sure it's something that we will be revisiting here many, many, many times because it's a hugely big deal. You know, we think that retirement reinvention should be something that's easy to do. The truth is, it's really hard and it can be really painful.

Paul Cronin (28:17.104)
It was just being, being together.

Josh Patrick (28:43.604)
and really lonely, especially if you're in passage and you haven't done any preparation for what's coming down the pike.

Paul Cronin (28:51.528)
Agreed. Agreed.

Josh Patrick (28:52.984)
So, at any rate, Paul, we are out of time, believe it or not. Well, as always, I told you it would. So, if somebody wanted to find you, how would they go about doing so?

Paul Cronin (28:58.48)
It flew by, Josh, as always.

Paul Cronin (29:07.196)
Reach out to me on LinkedIn — Paul F. Cronin is the easy way. I'm the only Paul F. Cronin on LinkedIn to my knowledge. And the other is if you want to send me an email, send me an email at [email protected].

Josh Patrick (29:22.574)
Cool. And if you've enjoyed this podcast episode and you think you would be a good guest for the Long Strange Trip podcast, just send me an email. Really easy. Just send it to [email protected]. That's the number two and “solution” is singular. So it's [email protected].

If you think that you'd be a good guest and you're a little bit scared, we'll set up a time for us to talk and we'll see if it really is that scary — because frankly, I don't think it is, but OK.

So thanks a lot for stopping by and taking a listen or a watch today. I really appreciate it. I hope to see you back here really soon.

This is Josh Patrick. We're with Paul Cronin and you're at the Long Strange Trip podcast.

Outro:
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