Purpose, Community, and Health After You Sell Your Business (Nate Collins)

In this masterclass episode of the Creative Genius Podcast, Gail Doby dives deep into the complex world of exit planning with former business operator turned wealth manager, Nate Collins. Nate shares his multi-layered financial background and details his experience taking over a struggling, 150-year-old theatrical licensing firm in 2011, engineering a major operational turnaround, and successfully selling it to the largest privately owned music licensing company in the world in 2019.

Despite achieving an extraordinary wealth-creating event, Nate candidly shares his struggle with post-exit depression—a phenomenon backed by a PricewaterhouseCoopers study revealing that 75% of business owners profoundly regret selling their companies within a year. He explains how an unexpected injury led him to author a comprehensive exit-planning workbook designed to guide owners through the personal, business, and financial “legs of the stool” during a two-to-five-year exit runway.

In this episode, you’ll hear about:

• The Emotional Toll of Selling: Why 80% of businesses that go to market fail to sell, and why the emotional friction triggers heavy overreactions for unprepared owners.
• Investing in the Right Advisors: The critical difference between standard accounting and a specialized M&A team (transaction accountants, M&A attorneys, and specialized wealth managers).
• The Liminal Period: Understanding the psychological phase between identity shifts, marked by feelings of confusion, uncertainty, and worthlessness.
• Prosperity vs. Well-Being: Nate’s personal shift from chasing personal prosperity to discovering that fulfillment only comes from structural personal well-being.
• Defining True Purpose: Why purpose is directly tied to being relevant to the lives of other people and serving something bigger than yourself.

If you’re listening on your favorite podcast platform, view the full show notes here: https://thepearlcollective.com/s15e4-shownotes

Episode Transcript

Note: Transcript is created automatically and may contain errors.

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GAIL DOBY
Well, Nate, I’m so glad to have you here today. You have had the most interesting career from trading distressed debt on Wall Street to managing commercial real estate at private equity firms, turning around a theatrical licensing company. And I think you have a few more little tidbits you want to share with me too, so why don’t you go ahead and add to that?

NATE COLLINS
Thanks, Gail. I’m so excited to be on this podcast. thank you for giving me the opportunity to speak to your audience. yes, so I have had a very circuitous career. It seems a little bit disjointed. However, at the end of the day, it has always done it has always been financially related. It has always been about investing money. And the two other ones that you mentioned.

is after I sold that licensing company, that theatrical licensing company that you discussed, and we’ll discuss that later, I then went on to work at a hedge fund and now I work in wealth management. So yes, you know, always in the financial field. But you may say, wait a second, theatrical licensing, how is that finance? That that sounds like theater. Well, ultimately the real business was entering into

agreements with the rights holders, the intellectual property rights holders, and entering an agreement to be a licensing agent on their behalf. And the way that it worked was very similar to real estate investment. We’d pay the the the rights holder up front a large amount of money and then once we had that that the rights to license that property similar to the right to our

If you own a busin if you own a a building, you lease it out. In this case, we licensed the property out for a specific amount of time and we try to maximize our return on investment by optimizing those licenses.

GAIL DOBY
Interesting. Well, you’ve also been a business owner, then that was before you were an a a financial advisor to them. And so how did that help you, eventually selling that theatrical licensing company?

NATE COLLINS
Yes. So I that was such a wonderful such a wonderful chapter in said circuitous career that I’ve had. And I really loved running a business. I really enjoyed operating a business. The the licensing company I took it over in two thousand eleven. It was almost gosh, two hundred and fifty years old. I’m sorry, a hundred and fifty years old. Not older than this country.

A hundred and fifty years old. and when I when I took it over in two thousand eleven, it was a real turnaround story. It had just been poorly managed for decades, but with some some exceptional luck and a great team, we were able to turn it around and become one of the most dynamic companies in the industry. And we ended up selling it in two thousand nineteen for a a

just more than we had ever expected. And it was it was a lot of fun. Obviously, like any business, I I had a lot of sleepless nights. So that experience though, how does it help me now? You know, I walked in those shoes. I walked in the shoes of a business owner from from having those sleepless nights, being concerned about employees

Being concerned about whether you’re making the right investments in the company. Sometimes thinking that maybe you went you were a little too out too much out over your skis and and being concerned and looking out for threats and looking out for opportunities. And then having the the opportunity to sell the business to a strategic buyer, the largest.

privately owned music licensing company in the world ended up buying our company. So it was a tremendous experience, full of ups and downs. And when I work with business owners now, I have that that sympathy of actually having been there. I can I can relate to their their

NATE COLLINS
their concerns because I know their challenges. I also know their opportunities. I know where business owners typically are not focused and spending enough time. And I know where they can do more to optimize the values of their business or the the value of their personal wealth. And it really is enjoyable because it’s my purpose. My purpose is to support

business owners through all parts of their journey, their business journey from inception to exit. And it makes me feel it makes me feel really good to have that purpose. It makes me feel needed. It makes it me feel like I matter to people. And so, you know, my best days are any day I get to talk to my clients or a prospective client talking about their business, helping them

solve problems, helping them create strategies that that achieve their goals.

GAIL DOBY
You know, it’s really interesting. and and we’re going to dive into exit planning and thinking about how to prepare your business for sale. And as we start doing that, I’m approaching that because I’m thinking about that myself. And I know that a lot of our listeners are in the same boat. They’re thinking about what is that future and how long does it take to prepare your business for sale.

So I’m definitely gonna go off the questions that I sent you and we’re gonna maybe go off on a tangent and talk about some things that are related to preparing for what is a very big moment in almost any owner’s life when they’ve worked for years building their business, and then it’s time to really think about that future. So talk to me a little bit about how you approach going through that process with somebody.

Preparing them for this.

NATE COLLINS
Sure, absolutely. Well, first, let me just share a little story. Earlier this year, in February, I slipped on some ice, fell down some steps, broke some bones in my back, got a concussion. and I couldn’t move for a couple weeks. Well, I when I say I couldn’t move, I meant I was I was laid up in bed for a couple of weeks. fortunately it was just some fractures and I didn’t need surgery or anything. But the one thing I could do was type.

So I actually wrote the I wrote a book on exit planning. Actually it’s more of a workbook and it guides a business owner through basically all the important steps to consider when when you are planning to eventually exit your business. And this workbook is set up to to guide somebody through anywhere from say two years to five years.

lead runway before the exit. ideally the more time the better, of course. And the key to having a successful exit, there are there are a number of keys, I guess, really. but let’s just start with the first one is really identifying three goals. Your personal goals, your business goals,

And your financial goals. You know, when I say personal goals, what are you trying to accomplish out of selling your business? Why are you selling your business? Is it because you want more time with family? Is it because you’re just tired of the grind of doing the business? Really understanding that. And then thinking about are there other things to do? Are there other ways to solve those problems?

Look, selling a business is really hard. Eighty percent of businesses that go to market fail to sell. So, and I hope that everybody here, everybody who’s listening, has an opportunity to sell their business someday because it’s an extraordinary experience and it leads to some great opportunities when you have that sort of wealth creating event. However, it is hard. So why are you selling your business? Right? But

NATE COLLINS
on from the personal side. And what are you what are you planning to do afterwards? And we can get into that later also. That’s a that’s a whole nother can of worms. from the business side, understand the goals. What do you want your who do you want to be the successor of your business? Who do you want to be the new custodian of this thing that you built, this child that you raised almost? obviously I can’t really compare

a business to a child. nothing’s quite like that. But the amount of energy that a business owner puts into their business is substantial. And a lot of business owners would say, Yes, actually my business is like my third child, or my second wife, or you know, something yeah. So something like not exactly, but it’s it’s just they feel very passionate about it is I guess what I’m saying. And

So who do you want to run that and what do you what do you see how do you see your team transitioning with that business and what’s important to you in that that legacy of this business that you built? Is it is it important that you get the highest amount of money for the sale? or is it important that the business continues

And the name of the business continues and the team of the business continues. So we talked about personal, your personal goals, your business goals, and your financial goals. What is it that you’re looking to do, accomplish on a financial level when you are selling your business? Why are you selling your business? Are or how much do you need to accomplish the goals of your next chapter? Whether that next chapter is

Is it starting a new business or retiring or something else? so you need to consider all three of those elements, the three legs of the stool, personal, business, financial, when you’re thinking about selling a business.

GAIL DOBY
it’s it’s complicated and I’ve actually had six of my clients go through exits and it has been a very interesting situation. I have one going through an exit right now and she’s she’s going I there’s a lot to it and I I really can’t divulge any of that here but it it has been an interesting process and as you go through this process and watch from the outside as an advisor to that client

And you’re coaching them about their business and helping them really build it and get it to where it is a saleable business. that’s a whole different thing than the process of going through a sale. And the sale is definitely one of the most challenging things I’ve experienced with my clients going through that whole process. And one of the things I find so fascinating is how emotional that process is from

so many aspects from how it affects your team to how it affects you as the owner of the business to how it affects the buyer of the business. how would you recommend that people prepare themselves for that piece?

NATE COLLINS
Yeah, you know, I found that when I was going through my sale, I was poorly prepared and because I was poorly prepared from that for that transaction, I ended up really overreacting to a lot of things and being highly triggered. It was a very emotional and tense process and that that lasts for, you know, anywhere from three to nine months. And so having that problem.

Preparation is important, and the best way to do that is by working with advisors who have been there because when you are selling a business, it’s probably most typically the first business that you’ve ever sold, and you probably are not gonna sell another one, and typically the person that you’re selling to.

has bought businesses before. So they’ve already they already know how that game is played and they typically have good very good advisors who are advising them and know how to maximize or optimize the the their own value of the purchase. So the best thing you can do is be well prepared by investing in your team of advisors.

And I call it investing in your team of advisors because the value that you get out of that investment will h will very likely be much more than the the investment that you made. Whether it is having a good MA advisor who can help create an auction process and drive up the interest in your business, help you market it.

to having a good MA attorney who can protect you on the other who can protect you from liability after you sell your business and can actually have very efficient negotiations with the the buyer’s attorney on the on the sale document to perhaps you have a you’re doing a qualit a quality of earnings with a transaction accountant.

NATE COLLINS
which can turn out to be extremely valuable, then on the personal side, you want to have tax strategies. Invest in those tax strategies. That’s that was the big mistake I made. I didn’t have any financial plan, any tax strategies going into my business or going into the transaction, going into selling my business. And I ended up spending millions of dollars in taxes I could have had I could have avoided had I been properly prepared.

And so invest in your team, invest early in your team, and you will reap the rewards, not only financially, but also just emotionally, because they will be able they will be there to support you and they will they will help you understand what is normal and how to approach the buyer when things may not be going the way that you expect.

GAIL DOBY
Mm-hmm. Well, and I I would have to say just watching from the outside on these other transactions, it there was so much stuff that I I had not experienced before going through this with my clients. And i it was it was great because I learned a lot and when I get ready to exit my business somewhere down the road, then I’ll have a lot more data points about what to do and how to prepare better. But

I I I love that you did this book and it’s unfortunate that you had to be laid up in bed to actually do the book, but tell me a little bit about it, what’s in there and some of the things that that you’d recommend that people pay cl very close attention to.

NATE COLLINS
gosh. So the book is really a culmination of the the my personal experiences and the lessons that I’ve learned working with dozens of entrepreneurs and executives as they have sold their business or their businesses. And I do a quarterly business exit planning workshop which kind of goes over those lessons and

I break it down into what I call the five the five elements of a successful exit. And the five elements we’ve kind of touched on on one of them or two of them already. First is you know invest in your team of advisors. Make sure that you have a f a complete team of advisors. As I said, I was just missing one

GAIL DOBY
Hmm.

NATE COLLINS
or two advisors. In fact, I actually had those advisors, but I didn’t have the right advisors. I didn’t have I had a financial advisor and I had a a tax accountant, but I didn’t have the right f type of financial advisor. Or and I didn’t really do a good job of talking to my tax accountant about the transaction before it happened. So that was on me. but so invest in your advisors, prepare

for your next chapter, your your for the your post exit life. And I’m gonna I’m on I wanna come back to that in a second after I finish the these five. So advisors, post exit life, align your personal financial plan with your business plan.

Thoroughly investigate the all the different types of buyers out there. So many times we think we know who’s gonna buy our business or who we wanna sell it to. But it’s a good idea to fully understand the pros and cons of selling to each type of buyer. And the the most important thing is understanding that what you want out of a transaction determines who you sell your business to.

Not the other way around, not somebody coming and giving you an offer determining what you want out of that transaction. So ahead of time, think about your goals. It goes back to all your it always goes back to your goals. And then finally is optimizing the value of your of your business. And there are a number of ways to increase the attractiveness of your business to a buyer. and obviously one of them

NATE COLLINS
is by working with an MA advisor and and going through an auction process, but just internally, making sure that the business is not dependent upon you, the the business owner or the CEO of the company, making sure that you have I guess policies and procedures documented so that somebody else can step into your company and run the company. Making sure that your your

account your books, your financial books and your legal, I guess all your all your important legal documents are complete and standardized. And there are a a number of other ones too. And all of those have an impact on on driving up the multiple of your of your business, the multiple of EBITDA that somebody’s willing to pay.

For your business. And so now I want to take a second to go back to really why is thinking about your post-exit life so important to a sale? Why is that an essential element? And I do a lot of public speaking about this in particular. There is a there was a study in South Africa that followed CEOs.

And found that after the these CEOs left their businesses, whether they were retiring or they were selling their businesses, these CEOs went into the this period which researchers call the liminal period, which is between I think that means between phases. And this period was marked by feelings of worthlessness, confusion, uncertainty, depression, regret.

There is a study done by Price Waterhouse Coopers that found that seventy-five percent of business owners who sell their businesses profoundly regret the transaction just twelve months later. Wow. So right, and this is supposed to be a a seminal period, you know, an event, a life defining event for people that they should have great fond memories of, yet they regret it.

GAIL DOBY
Ooh.

NATE COLLINS
And I was one of those people. A year after selling my business, or within a year, I regretted selling my business. And why is that? Well, I didn’t properly prepare for the next chapter.

And so I I spent probably three or four years suffering from depression. I wouldn’t say it was clinical, but just I was not me. You know, I went I I I remember a f I went and saw a friend and the friend said, you know, Nate, you you sound like you have postpartum depression. And I did. I really you know. Yeah. Right. And and it’s not just business owners that go through this, it’s anybody who has a

a significant change in their lives. Mothers, right, you know. or say you retire. or say you move, you probably have this this you may have this these feelings of you may be going through a liminal period as you reestablish your your new life, your new routines. But I was I was really suffering and it really impacted

my identity because I always thought of myself as a very optimistic and energetic and I guess reliable person and and

These feelings were were changing who I was. And and not only did my friends notice that, my family noticed that, my my two children noticed that, and that was not the ident the identity that I wanted. That’s not the the legacy that I wanted them to remember me by. So, you know, I I I looked around, you know, it’s funny, when I before I was settling my business, I really wanted for me, my goal was

NATE COLLINS
personal prosperity. I wanted when I sold my business, I was like, I want to make a lot of money because I grew up without money. I grew up in the woods, in in the cat skills, without electricity in a in a cabin. So, you know, finally having some level of wealth was very important to me. And so afterwards, because I was not happy, I wasn’t fulfilled, I thought, well maybe I just w was not wealthy enough. Maybe that was the big problem.

And so I went and worked worked at the hedge fund that I told you about. And I still just I still didn’t feel fulfilled. And I went and had lunch with my my my business coach and he recognized that I was going through the liminal period and he said, Nate, listen

I’m gonna share with you my framework for personal well being, post exit personal well being. And he said it’s three things. It is purpose, community, and health.

Find your purpose, build your community, prioritize health. Now, health, right, Maslow’s hierarchy of needs is like basic, right? That’s need to you cannot you cannot have any well-being without personal health. And so that’s mental and physical, and and there’s a lot that goes into health, especially mental health. And one of the things that goes into mental health is feeling secure about your finances.

And I hadn’t done that, right? I told you I I didn’t have a financial plan. So, and I just didn’t know what not I didn’t know what having money in the bank meant. All I knew what having a paycheck meant. And that’s what happens to a lot of people who sell their businesses. It’s or retire. They say, Well, you know, I I I don’t really know what this means to have a lot of money in the bank in the bank, but I know what it means to be able to pay my bills with my

NATE COLLINS
With my paycheck. so I had to sort that out. But then community. A lot of a lot of entrepreneurs, executives, a lot of people who’ve been in a business for a long time, their community are the people who are in the business or the the in that commun or in that industry. And I’ll tell you, when you sell your business, if you sell it on a Monday, Tuesday, nobody’s nobody’s calling you. you know.

Maybe maybe you get some calls to say, hey, congratulations, but in general, a lot of those relationships, they just they they dissipate very quickly. And and so who is your new community after you sell your business? And then the third thing is is purpose. And purpose, a lot of people say, Well, go find your purpose, but I don’t think that’s actually

I think you need to define it more and the way that I think about their purpose is purpose having a a sense of purpose comes when you feel like you are relevant to the lives of other people. When when the fact that you are in existence helps other people achieve whatever it is that they are trying to achieve.

when you’re doing something that is bigger, you are there for something bigger than yourself. And, you know, that’s why you can’t just, you know, sell your business and then go play golf all the time, or sell your business and go sit on the beach, whatever it is. you have to you have to do something that helps improve the lives of other people. Now that could be, your purpose could be a non it could be charitable.

You know, you don’t need to get paid for it. Or you could be doing something that provides an income for you. it could be working with people who don’t have any means and need financial support or need other things to to actually just basic things to live, or it could be just people who need knowledge and information. could need be people who need just support.

NATE COLLINS
They need somebody to talk to. And and it could be less direct. It could be helping to improve the environment because that, or helping work in work in your local community because that helps improve the lives of other. Whatever it is, you will find purpose when you are doing something that benefits the lives of other other people’s lives. And I finally found that.

After talking to my business coach, I realized that my I had been I had the wrong goals in life. My goal had been personal prosperity. And it’s no wonder that hadn’t led to personal fulfillment because it doesn’t. It was actually personal well-being that leads to fulfillment. When I finally created new goals that supported my ment my mental health, my

my community or building my community and finding my purpose, that’s when that’s when I was able to come out of the liminal period. That’s when I found personal fulfillment. And that’s what brought me here to doing what I do today. As I said before, it’s my purpose. I love it. I love talking about it all the time. I love sharing my story. I mean if it can just help one person

transition into their next chapter more easily without having to go through what I went through. It’s completely worth it.

GAIL DOBY
Mm-hmm. That’s so great. Well, I it’s so important to have this conversation early, as you said, and two to five years out from the time you’re planning to exit. And it’s a fascinating process for each person to go through. And I I think about this because my husband’s been retired for eight years and he’s a happy clam. He is the happiest guy.

And his purpose though is to take care of me. So it actually has worked out quite well for me because I am just one of those people that’s very driven by my purpose too and what I’m doing. So this has been a really interesting conversation and it has given me a lot of things to think about for myself as well. So I greatly appreciate you being here today.

NATE COLLINS
Gail, what is your purpose?

GAIL DOBY
My purpose is really to help other people build a business and a life that are meshed together that they love and have the freedom that they want to have in their lives, whether it be financial freedom or time freedom or both, they re they can have that. And to me that if I can help them do that, then that is I’ve achieved my goal with them.

NATE COLLINS
Mm. That’s great. And you know, I think the key words were the first words that you said. My purpose is to help dot dot dot. Help or you know, my purpose is to help other people. And I think when you can say that, that’s or when you can say I help other people, that’s when you know you found your purpose.

GAIL DOBY
Mm-hmm. Yeah, I it’s something that late in life I decided to start this business. I was 52 when I started it and much older now. And it’s been thank you. I wish it were true. But honestly, I think it’s been one of the most challenging and interesting and fun things that I’ve learned is that every day I get to learn, every day I get to help these people grow.

and expand and not just themselves but their whole team and just helping companies understand what they need to do internally in their their companies to be ready to sell or be ready for all those other future things that they’re looking for, it has to be very intentionally done and it takes a lot of work.

NATE COLLINS
Yeah. Yeah. That must feel it must feel great to to have a one of your clients go through and have a successful exit.

GAIL DOBY
Yes, and I hope every one of them has exactly what they want out of it. So well, thank you so much for your time and for coming t today, Nate. And please tell us the name of your book so that we can have everybody go buy that if they’re getting ready to act.

NATE COLLINS
Well, it’s still a working title, so I don’t know what it is. but I I expect that I’ll be giving away more books than I will actually be selling. And what I would like to do is invite everybody just to send me an email if they’re interested in learning more. my email is Nate.collins at remondjames.com. You can also find me very easily on LinkedIn at NateCollins.com.

Raymond James. and I invite everybody to join my ex business exit planning workshop. I do it on a quarterly basis.

GAIL DOBY
Great. That is so great to hear. We’ll make sure and put that in the show notes. So thank you so much for being here today.

NATE COLLINS
Thanks so much, Gail. It was a pleasure.

GAIL DOBY
Same here.