From 9-Figure Deals to Daily Fulfillment: Investment Banker Rand Selig’s Blueprint to Thriving in the Second Half of Life Before It’s Too Late (#463)

Send us a text Unlock Proven Strategies for a Lucrative Business Exit—Subscribe to The Deep Wealth Podcast Today Have Questions About Growing Profits And Maximizing Your Business Exit? Submit Them Here, and We'll Answer Them on the Podcast! “ Trust that everything will work out and smile.” - Rand Selig Exclusive Insights from This Week's Episodes Rand Selig—investment banker, author, and founder of Selig Capital Group—has spent decades guiding entrepreneurs through the most important transiti...
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“ Trust that everything will work out and smile.” - Rand Selig
Exclusive Insights from This Week's Episodes
Rand Selig—investment banker, author, and founder of Selig Capital Group—has spent decades guiding entrepreneurs through the most important transitions of their lives. In this episode, he reveals why thriving is about much more than valuation, and how to align your personal and professional life before it’s too late.
00:04 Thriving is about the average over time, not daily highs and lows
00:06 The link between personal fulfillment and business success
00:09 How to spot personal blind spots before they damage your business
00:13 Leadership vs. management—why they’re not the same
00:19 The power of reciprocity and collaboration in business relationships
00:28 Knowing when it’s time to close a chapter and start a new one
00:32 Don’t retire—rewire: redefining identity after exit
00:37 The silent crisis most entrepreneurs never discuss
00:40 The most challenging chapter Rand wrote in Thriving
00:45 The central role of relationships in lasting success
Click here for full show notes, transcript, and resources:
https://podcast.deepwealth.com/463
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463 Rand Selig
Jeffrey Feldberg: [00:00:00] What happens when someone who spent over three decades walking alongside business owners for some of the most important decisions of their lives begins asking deeper questions about purpose, legacy, and what truly matters?
Meet Rand Seig.
As the founder of the Selig Capital Group Rand, has built a career working with privately held middle market companies.
Often sitting at the same side of the table. As founders and owners. His approach is personal, not transactional. Long before the numbers. He starts by understanding what matters most to the client, and he carries that clarity through every stage of the journey until the deal is done.
What sets Rand apart isn't just expertise. It's his ability to see both the business and the person behind it. He knows that selling a company is never just about the valuation. It's about identity, relationships, timing, and trust.
This is a rare conversation that looks beyond spreadsheets to explore the emotional human side [00:01:00] of a business transition. Whether you're thinking about the future of your company or simply wondering what's next, Rand brings the wisdom and calm of someone who's helped others find clarity and peace with the biggest decisions of their careers.
And before we hop into the podcast, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. We have William, a graduate of Deep Both Mastery, and he says, I didn't have the time for Deep Both Mastery, but I made the time and I'm glad I did.
What I learned goes far beyond any other executive program or coach I've ever experienced. Or how about Bruce? Bruce says, before Deep Wealth Mastery, the challenge I had with most business programs, coaches, or blogs was that they were one dimensional. Through Deep Wealth Mastery, I'm part of a richer community of other successful business owners.
The idea shared forever changed the trajectory of the business and best of all, the experience was fun. And we'll round things out with Stacey.
Stacey said, I wish I had access to the Deep Wealth Mastery before my liquidity event, as it would have been extremely [00:02:00] helpful. Deep Wealth Mastery exceeded my expectations in terms of content and quality.
And you know what, my Deep Wealth Nation, why they're saying this is because Deep Wealth Mastery, it's the only system based on a nine figure deal. That was my deal. And as you know, I said no to a seven figure offer, and I created a system that we now call Deep Wealth Mastery that helped myself and my business partners, welcome from a different buyer, a different offer, a nine figure exit.
So if you're interested in growing your profits, preparing for a future liquidity event, if that's two years away or 20 years away, and you want to optimize your post exit life, Deep Wealth Mastery is for you. Please email success at deepwealth. com. Again, that's success, S U C C E S S, at deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as Scale for Ultimate Sale. That's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders just like you who are looking to create market disruptions.
And they want to lock in their financial freedom and have success and [00:03:00] fulfillment.
That's the 90 day Deep Wealth Mastery Program. It has your name on it. All you need to do is take the next step. Send an email to success at deepwealth. com.
Deep Wealth Nation welcome to another episode of the Deep Wealth Podcast. Well, you know me and my rhetorical questions. Yes, I have yet another rhetorical question to kick things off in Deep Wealth Nation. Simple question, are you thriving? And I know for most entrepreneurs when I speak with them more times, sadly more times than not, usually it's, well, no, I've got this, I've got that.
And we do a bit of a deep dive into why that's the case it doesn't have to be that way. Well, that is our focus in the House of Deep Wealth. We have a very special guest. And for those that have been in the Deep Wealth community for a while now, this is no Stranger to you. So Rand, welcome back to the Deep Wealth Podcast.
An absolute pleasure to have you with us. And let me ask you this. There's so much that's been going on since we last spoke for the existing members, for the new members of the Deep Wealth Nation. Why don't you bring us up to speed? What's your story behind the story?
Rand Selig: The story behind the story. Yeah. [00:04:00] Yeah. life is what we make of it. These are little things we hear. We know this. And I continue to work on making my life good. Every day is a different adventure. Some days are great, some days are less good. And the happy news for you, Jeffrey and your listeners, is that thriving is not about the weather.
It's not about today. It's about the average over time. So if on the average over time you feel really good, you're feeling like you're thriving you're doing well, and all the different dimensions of your life, well then. I'm happy and that's what I'm working on. I'm working on that. It's a daily thing, but it's not, I'm working on it.
That, that sounds like it's pressure. It sounds like I'm struggling with it. No, it's just I'm clear that's what I wanna do and I know how to get there and I know how to stay there. It. I just push into that and when I find myself saying, Hey, today isn't the greatest day, I ask myself, why not?
What's going [00:05:00] on? That, brought me from my typical kind of nine out of a 10 scale to my low seven. I can journal, I can sort that out and I go yep. This is so obvious. This is what didn't happen, or this is what did happen. Just remind myself of what makes it all work for me.
Jeffrey Feldberg: While you're talking about that, we're gonna talk a whole lot more about that Depa Nation. Go to the show notes. And in the show notes. By the way, everything we're talking about today will be there, but what also is gonna be there, Rand has written a whole number of books but a particular book one of my uh, favorites, we're gonna be talking a little bit about that today or a lot about that today, is thriving.
How to create a healthier, happier, and more prosperous life. And hey, who doesn't want that? You're talking about our health as our first wealth and being happy and prosperous. We're gonna get there, but let's go back so we can move forward. And Rand, you've been doing this now for a whole number of decades where you've been helping leaders, you've been making a difference.
And [00:06:00] I'm curious because there are always patterns. The human condition, we do some of the similar things over and over again, sometimes for better, sometimes for not. Are there patterns that you're seeing day in, day out with entrepreneurs, founders, business owners, where it's on the one hand they're doing this and it's holding them back, or on the other hand, yeah, they're doing this and this is when they feel most alive.
What would you share with us? I.
Rand Selig: Well, I think the aliveness comes when you're aligned. You're in alignment with your values. You're in line with your skillsets. You're honest with yourself. doesn't feel good when you're sort of saying, oh I'm gonna do this. And then you really say to yourself, secretly, I don't like doing it.
Or, Hey, I'm gonna jump on this and it's gonna be great. And they think, well, I'm not very good at that. So it's gonna be a flop. You gotta come at this with humility. You gotta say, Hey, here's the stuff I'm good at. Here's the stuff I'd like to do. Here's what I'm, energizes me because it, it's centered on what I believe in, what my [00:07:00] values are and all the other stuff.
Stay away from that. Or assign it to somebody else on your team gives you great power and keeps you away from those messy potholes that are have glue and stickiness in them, hard to get out of sometimes. Humility, honesty, and then just being authentic. that's what it's all about.
And what happens when you're doing that is you get a lot of energy and you start feeling good. And that, that radiates out. All my clients when I started talking about what their objectives were and they wanna know more about me and how I would work with them, and I just brought me to the table, I could just see them relaxing and lightening up and saying, I can't wait to start. That's a great thing. You want a client to say that.
Jeffrey Feldberg: absolutely. And so let me ask you this. I'm gonna share on the business side of things some of the things that we do here at Deep Wealth, but I wanna take it back to the personal, because for me, I've always. Found in my own experience data 0.01, [00:08:00] but it seems to be holding true and is consistent for others as well.
That regardless of what's going on in the business side, everything always goes back to the personal side. So if we get it right on the personal side, that is going to flow through one way or another into the business. The opposite can be said as well. It's also true if we miss it. On the personal side, things aren't quite working.
I'm not happy. I'm having some challenges that's also going to show up in the business. So on the business side, one of the things that we do is step one big picture. This is in our 90 day Mastery program where we're talking about how do we grow profits today and down the road we exit for financial freedom and independence on our time and our schedule.
And in step one, big picture, we look for what some people call blind spots. We call them inflection points. And in the business world, it's something that's going on in the background. It's very small. It's not really. Big and front page right now, but left unchecked, it'll either put me outta business, it'll have my competition catapult me, or have my profits, my growth, the ability to create a market [00:09:00] disruption just go out the window.
So let's take that concept now onto the personal side, and when it comes to thriving for those blind spots, for those inflection points, what would be some questions or some introspective insights that I can be doing as a leader to look within so I can find those personal blind spots or inflection points, put them front and center, talk about them, correct them, and then take that with me to the business.
Rand Selig: Well, there's no substitute to just knowing yourself. You gotta know your story. You gotta know what led you to this point in time. You gotta know what it is your aspirations are. why are you in business? What are you trying to accomplish? So if you're an established entrepreneur, you, they're, you're sitting at a certain place and you say, what's next for me?
And how am I gonna get there? If you're pretty new to the story, you're kind of saying is this one gonna be working out? maybe it's your first go round. am I [00:10:00] missing? How am I gonna do this and do it well? How am I gonna get to this place where I'm happy with it and I'll call it successful?
Knowing yourself, it's about knowing yourself. And again, that takes honesty. You can't just say, okay, great. The reason why I got a B and a C was because a teacher was bad. You can't point the finger at somebody else, you gotta say, okay, here's what I contributed to either the good stuff or what I contribute to the bad stuff.
So you come to the table, your table, you've made the table. Now you're, putting some silverware and some plates and some glasses on it. And you're saying, okay, we're gonna have a feast. we're gonna, I'm gonna cook up a meal and we're gonna enjoy it all. So knowing yourself is and the mistakes, this is such an important thing.
What mistakes have you've made where you have to calibrate? Are you really strong in management kinds of tasks? Are you good at delegating? Are you good at organizing the work that needs to [00:11:00] be done? Are you good at motivating? As opposed to, are you good at leadership? They're very different skill sets.
Leadership has a lot to do with having a vision and being and articulating that vision, repeating it, and inviting people in so they can add more paint and more color and more definition to what you were describing. So you gotta say, which am I of very few people very few people are good at both. For, in my case, I am a really good leader.
A really good leader. And that started way back in high school. But I had to work hard to become a. A good solid manager. 'cause managing has a lot to do with people. And I could see a picture that's the vision side. And in high school, I was the yearbook editor in chief. And boy did we had a home run that, in fact, people all these decades later saying that yearbook was fantastic.
I just pull it out when I'm trying to remember somebody's [00:12:00] last name. There it is. There's, and I remember how incredible those four years in high school were, and thank you so much. And so the vision of what we created with that yearbook stands today and I'm very pleased with that. But the management of the process was rough.
I was very aggressive. I would say at times verbally abusive even, my section editors I'm dreading going in to deliver my pages to for inserts in the yearbook because I'm afraid that Rand's gonna, yell at me about something.
that's not a way to motivate people. And I got that feedback. It was very painful. And I committed to work, on that issue, becoming a much better manager which I did. And I have become, I'm still a better leader. And so these are the kinds of things that you get just have to know.
And when you know that about yourself, then you can steer your ship. You can avoid things that [00:13:00] you just don't wanna do, and you can aim to things and embrace and bring in more opportunities to do the things that you are good at and you like doing.
Jeffrey Feldberg: As you're talking about that, I wanna reflect on an earlier conversation and Debolt Nation. Go to the show notes. The links are all there for an incredible conversation that ran you and I had. In fact, it was so good. Afterwards, we were talking, we said we should really do this again. And lo and behold, here we are with that.
One of the things that we scratch the surface on, but I wanna revisit it, we were talking about the difference of least. Leadership and management because so many people, they use the two words interchangeably. It couldn't be further from the truth of leadership versus management and the impact that has, particularly in an entrepreneurial company.
So let's double click on that and revisit that one more time and perhaps take it from a different angle. So Rand, given what you've done from the boardroom, from the investment banking, from the deal making to now the coaching to being an author, a [00:14:00] thought leader as you look back so you can look forward, leadership management, my goodness.
What would you want Deep Wealth Nation to know of one, the difference between the two and then how to really extract the best leadership out of us.
Rand Selig: Yeah. There's, I think a whole chapter in my book called Leadership and Management. I encourage your listeners to grab a copy of the book. Read that there's included in that chapter are a series of things that I've pulled out from, collecting articles and following people that are, I think really helpful about how to go through creating culture.
What is the process that you need to undertake as you're building your company? The issue of role and style, whichever you're in whether you're the, in the leadership category or you're in the the management category. I refer to Six Habits of Extraordinary Bosses by Jeffrey James.
Oh my gosh [00:15:00] so good. I talk about the Eight Core Beliefs of Extraordinary Bosses, also by Jeffrey James, and then. 10 thoughts about leadership by John Gordon. These are things that we don't have time to go into any real details here on this podcast, but they're in the book and there's web links that people can go to, to just embrace those things.
I pull them out because after all this reading, lots and dozens of books on management and leadership, and running my own firm for more than three decades and working with hundreds of companies. I gotta tell you, these are really good. To answer your other question. This is all about, in some cases reciprocal relationships. This is where life is good, and `where your effectiveness just expands when there's some kind of reciprocity, if it's all a one way flow, whether it's coming to you or going back from you to the other person, there's not a lot of hold [00:16:00] on that, there's not enough power in that.
So reciprocity is a big component. I think it's very important to think win-win throughout this, again, regardless of whether you're in leadership or management thing. And communication becomes absolutely central. You gotta, seek to understand before you try to explain, that wherever you're coming from, if you skip that step you're just gonna roll over people.
'cause they're eager to share and they'll be shut down some incredible percent. Something like, well over 40% of people leave their jobs is because they don't feel seen, they don't feel appreciated, opinion's not valued. Those are all avoidable things. You got just two words? Thank you. Thank you.
We'll accomplish so much. And you know what you're, what we're all trying to do is create synergies. This is the magic when. People have a degree in mathematics. So one-on one [00:17:00] can be a lot more than two, can be three, but I like to say one-on-one can be 11. Hold, I hope, hold up my two index fingers.
It's, I borrowed that from Gandhi. But these are really good elements to this whole arena of life in the organizational world, in the corporate world for nonprofit world. And let me add one more thing to this. Relationships. Relationships. A lot of people are thinking their job is to sell and by.
By thinking of that in that way, they can become overly aggressive and really not be listening very much, especially the feedback or resistance points. So what you need to do is shift that to think about being of service and being of service. Might be providing your product or services.
Absolutely. But you come from a very different place. And part of this is what leads to [00:18:00] is a little two by two matrix, which I think is very revealing. And on the two columns are your outcomes, are they low or are they high? And then on the two rows, it's what's the relationship?
Is it a low quality relationship or is it a high quality relationship? So let's go to the bottom of the barrel. The relationships are low and the outcome is low. What should you do? You should avoid that. If the outcome is low, but the relationship is high, then what you wanna do is accommodate if the relationship is low, but the outcome is high, that leads to competition.
Lemme just say that again because that's so important. People are very confused about what is the whole competitive space. Relationship is low, but the desired outcome especially, is high. That's when you're competing. So the gold standard here is where your relationship is high and the outcome is high, [00:19:00] and that's when you're collaborating. The whole communication cycle is completely different. It goes back to listen first, to understand and then to be understood. So relationships with others is a, just an enormous part of being in the business world in a successful way. And I think I've sort of skipped over, I did talk a little bit about this issue of what is it that is the difference between leadership and management?
So put your hat on. Either it's the hat you wear or the hat you see someone else wearing, or the hat you'd like to wear, the leadership hat. So what are you doing? You're setting direction. You're creating and articulating the vision, you are fostering culture.
And how are you doing that? Because you're encouraging, brainstorming. It's, you don't have all the answers and you don't put on the airs. If you do, you are inviting other people to [00:20:00] participate in that vision and making it better. You initiate action. You're the initiator. This is why leader is such a power.
We talk about people being leaders instead of saying they're managers, when in fact that, a lot of things that are happening is in the carrying out the operating level. That's the management side, but the initiating of action. And that takes persistence. A lot of leaders are seen to be tenacious and sometimes may be obstinate or bullheaded.
I can say wow, wow, that guy's a fantastic leader. Or She's great, but wow. Tough. She's so persistent with this. They have the ability to motivate. Wow. Think about a situation you're in where there was no motivation, where you weren't motivated, where the people around you weren't motivated.
Wow. That's, you can't get the rocket to get to the moon if there's no motivation.
Jeffrey Feldberg: I love what you're sharing with us and putting out there, and what I particularly [00:21:00] admire about this ran so many, I'm not gonna name names, there's just so many out there, particularly with social media today. They're spewing out this stuff and it's theory. It's not from the trenches, it is not tried and true.
You're coming at it from a completely different perspective because you've been there as the saying goes, been there, done that. You check that box. And so let me ask you, I wanna take you back. To your days as an investment banker. And when you and I spoke for the first time, we were covering what I'm gonna say would be some of the more fundamental kinds of things.
And we spoke about the book of course, and what was in all of that. And by the way, deep mention, again, go to the show notes. I'm talking about episode 4, 4 2, where Rand and I did a deep dive on the book, what his backstory is, how he got to where he is today. But now I wanna go even deeper with that. And here's what I have been thinking about between now and when we last spoke and today.
And here's the question for you. When you look back at the time you're an investment banker and ran, maybe you don't [00:22:00] wanna look back when you're an investment banker, but when you do, my goodness, you were just hitting it outta the park with what you're doing. You were creating success not just for your clients, but ultimately for yourself.
What I'm curious about though is. What part of you had to die? What part of you had to die in order for something new to be born? And where I'm coming from, that is in your journey for where you are today. You are opening chapters, you are closing chapters. And I know for me, myself, that's where I failed the most, where I should have closed the chapter.
But I kept it open because I was too scared. I was afraid to close that chapter. I was afraid for that part of me to die within, so a new part of Jeffrey could be born and to take that to the world. So from someone who's done that number of times, what was it like for you? What could you share with us?
Rand Selig: Well, it's a fantastic question. And I imagine that over some period of time, everybody faces that in one way or another. I faced it in my company in a number of [00:23:00] ways I had to pivot. For example, I thought initially, even though I was very focused in what the services are that my company would be providing to company owners and often founders I thought that I could dive into all kinds of industries.
Part of that's fun for me 'cause I, like to learn. And so taking on something new, but that was a stretch. And after a fairly short period of time, I realized, wow, I gotta be upfront and honest with somebody. Somebody's coming to me and says, oh, you know, you're being recommended to me by our law firm.
Or some other of your clients said get ahold of brand. You're gonna love it. I would say to them, your company, from what I know and what the information you sent me, is doing some terrific work. The issue is for me to really understand and be of the value I want to be to you, I have to learn a lot.
I've got a steep learning curve because I can't do the job I do just sort of with little soundbites. I gotta [00:24:00] really understand what it is you're doing and what's gonna take it to the next level so I can find the right buyer for you that somebody who's gonna have synergy with your company and bring, the next step to you.
Not just with capital, not just with extra bench strength, but in sort of the, the r and d side. Possibly not in every case, but in many cases. I would say I cannot charge you for my education. I'm not the right guy for you. I, and I'm sorry. I'm sorry that's the case.
'cause this would be fun, but let me find somebody else that could, I think, do a good job for you. And people appreciate that honesty. And in some cases people would say, I'm sorry that we won't work together, but if I find somebody else that I think would be a good fit for you, I'm gonna send 'em your way.
And I said, thank you. Absolutely. that would be most appreciated. So that was kind of a, not a pivot maybe as much as a, a clearer focus on what it is that I could be providing. So I didn't get [00:25:00] myself into trouble. Struggling paddling ferociously trying to learn and honor a timeline that I'd set up for a client.
So that's one thing. I think being realistic because when I set up my company, this is after a dozen years on Wall Street, I said it's gonna be based on some principles. I thought very hard about that. And I chatted with a few people I thought of as a good advisor said, here's what I'm thinking of doing, and here's the principles I'm gonna base this on.
What do you think? I talked to my wife about it and they looked to me and said, I wish everybody was thinking about designing a company around principles. Wow. And I did. And that was a marvelous thing. I didn't have to look back about the basic core principles. It's like having clients that I could communicate well with, that would be honest and open with me and tell me the truth.
The bad news as well is of course the good news. I needed to hear that to, for me to do the job I needed to do. [00:26:00] So I set up a set of key core principles, one of which was that I wanted to have space in my life to be doing more than running my company. I wanted to live and work in the same town, the beautiful town of Mill Valley.
I wanted to, and if people said, well, I don't know if I wanna work with somebody who doesn't have a San Francisco Financial Street address, I'd say good. If that's what they're looking for. I don't want have them as a client. I'm about quality. I'm about substance, not how sweet my uh, view is out the window looking at the Golden Gate Bridge or some fancy conference room.
And another thing is I decided that it would be okay to have maybe a maximum of five clients at a time. And there were lots of years. The first maybe decade or two, I had a full slate. I. And, I had to really hunker down and get that done because I wanted to spend time with my [00:27:00] family.
My kids were little, I wanted to read books to them when, they were very little and put them to bed at night. I wanted to have dinner with them if I wasn't traveling and so on. So limiting myself, saying no to clients saying, look, I'd love to work with you, but can you wait 90 days?
And they would say, for this, for you, yes, we will. In some cases they said no. I said, I understand, but I'm not gonna add on more work 'cause that deprives my other clients of my attention and doesn't do a good job for you either. So that's a discipline and integrity and a lot of integrity about that.
Jeffrey Feldberg: And so it sounds as though it was you being honest with yourself first and foremost.
Rand Selig: Yeah.
Jeffrey Feldberg: And what I'm wondering, how did you know within, okay, I'm speaking as you, okay. Rand, we've done this investment banking thing, it's been a terrific ride. It's time to move on where there's some telltale signs. Was it a conversation, an inner dialogue that you were [00:28:00] having lately?
Was it how you were feeling, what was going on where perhaps you just woke up one day and said, okay, you know what? Not gonna happen tomorrow or the next day? Let me start preparing though, because the days of investment banking are going to be coming to a close.
Rand Selig: had that conversation for, oh, gosh five, seven years. And I had a rationalization and a justification. I like what I'm doing and I'm very good at it. My company was named the best sustainable investment banking firm in San Francisco Bay Area last year, and it's been nominated again for this year.
And that's a fantastic thing. And it, it came about by uh, being very focused and honoring our word about what we're gonna deliver and what we can deliver and what we're not gonna deliver. And I thought to myself, I don't wanna ever retire.
In fact, I think that's a terrible word I'm gonna rewire at some point. But I like doing this and I was, I had seen so many clients who couldn't wait for me to sell their company so they could [00:29:00] retire. And then I, because we had built such a great trusting relationship, we'd stay in touch.
They'd call me periodically say, Hey how are you doing? And let me ask you a question if you don't mind about something. I'd say Fire away. Good to hear from you. And I thought, well, I saw theming.
Going through their bucket lists and then becoming really kind of much smaller stumbling around with their thoughts and their words.
The golf games weren't enough to keep them fit. So I said, wow, it scared me. I said, I don't wanna be in that position, so I'm gonna hold on. I'm gonna keep doing deals. If it shrinks from doing three deals three clients at a time, three deals a year, whatever. I'm fine. This isn't about money.
It hasn't been about money in a very long period of time, fortunately. But it wasn't fresh and new as much as the clients were all different. and nothing was a cookie cutter. it didn't [00:30:00] feel like a big challenge. It didn't feel exciting. It wasn't invigorating anymore. During the beginning of Covid, so five years ago now, I was in my office and I was looking at this big stack of papers and I said, wow, there are at least one book in there, and there's at least one book inside of me. And I started undertaking that. And that's what produced thriving, how to create a healthier, happier, and more prosperous life.
And I gotta say that I've kind of shifted you getting out of the rowboat that was, drifting along to the new raft with so many adventures. So much exhilaration, so many great new people in my life. Our conversation, Jeffrey I meeting people where we're collaborating about things.
I'm just finishing up the audio book. All this is brand new stuff for me, and I feel alive and alert and I. And young. I've just shifted courses and it's, [00:31:00] I have a mission to engage people about the possibilities. So it's, there's very purposeful, very intentional work I'm doing I get up early and I'm excited.
My, feet hit the ground. I don't wanna go to the beach. I don't wanna goof off. I wanna engage.
Jeffrey Feldberg: You have your purpose, you have a sense of your legacy, and you mentioned this the last time we spoke, you mentioned it again and I wanna ask you, because I first, I love your saying. Don't retire. Rewire. And I would say randomized experience of working with entrepreneurs and even myself included, you're one of the few that's actually been able to do that in a way that feels good for you.
'cause for most entrepreneurs, and this is the question, what does it actually mean for someone who's built their identity around the business? They are the business. The business is them. And as an investment banker, you would see that more than most. It's really difficult to sell someone's business when it revolves around them.
Most buyers don't want a second full-time job, otherwise known as the business they just bought. So for those entrepreneurs that find themselves in that [00:32:00] situation where their identity is tied up in the business, what does that look like for them? Of, okay, don't retire, rewire. That's life. Without the business though, what advice would you give?
Rand Selig: yeah. I mean, There have been so many clients where we were just, weeks away from a closing. And they get, they, I just saw them getting more and more nervous and I said let's have another conversation. What's going on? Tell me what's going on. Is there something about this transaction that's making you pull back?
Talk to me, and I. Brand. There's nobody else I can talk to that's better than you. I can't talk to, I don't have a board that really means much. My spouse is not the right person. You have proven over this last, whatever, six, nine months that I can share that with you.
And it was about who they were. Their identity was their business card, and it said CEO, it said, founder whatever it had. And I said, I have these nightmares that I'm ripping that card apart. And I'm poof gone. [00:33:00] I'm nobody. So what do I do about that? And I said, this is not the first time we've talked about who you're going to do, who you're going to be, and what you're gonna do after the company is sold.
Because you said, and what we've arranged is that you're not going to stay in past a, a 90 day, six month period of time to transition the company. And after that, you've said you want it out. So that's where we arranged. Do you still wanna do that? Yes. Yes. So who are you? What do you wanna do?
We've had conversations about your hobbies. You've loved architecture, you've loved natural history. These are things that you've spent very little time with because of the press of the business and other obligations you have in your personal life. Now's the time. Now's the time.
Join a board. Go volunteer. Find out, dive into this. What is really going to be exciting for you, that you're going to wanna read about it. You're gonna wanna, you were [00:34:00] there, you signed up for a three hour shift at the museum or wherever, and you don't wanna leave. That's a sign, that's a big sign.
You can add variety of ingredients. Look what you've done to yourself, over the last 20 years or so. Y you have not had the time to take care of yourself. So add that as a project that creates some physical vitality to who you're, your strength is just naturally gonna be ebbing as you age.
So jump on that now. Strength, stability, stamina. It'll treat you give you many dividends if you handle that. But that's just an aside thing. That's just the fuel to get on with a new purpose. Find some people who need you. It could be your neighbors. It could be a nonprofit
Schools there's some entrepreneurs I've dealt with who are just brilliant in some way or another, or at least skilled. where are you gonna share that? Are you gonna go to the high school? you know, are you going to be [00:35:00] available to people who could really benefit from your collected wisdom?
Dive in. Dive in. Don't pull back, dive in, push forward. I'm here to have more conversations with you about this because it's a rich treasure trove of possibilities. Your, and then I tell 'em something they probably have rarely have ever heard. Let me tell you who I see. I walk them through and they're sitting there almost quaking like they're naked.
I see a marvelous person. Yeah, you've got skills and look what you've done with your company and look what the value you've created that we're now about to transact on. You've done that, but look at the person you are. Look at the person that people care about, that people come to your office and wanna share a story or ask for advice.
This is the person you are. And shrink away from that. Build more, do more with that with in other venues, and they get teary eye and I go, can I give you a [00:36:00] hug?
Jeffrey Feldberg: What I'm hearing you say, and as you're talking about this, it's really being honest with oneself going within, having the courage to have those kinds of conversations and then face it whatever is coming through. from the Don't retire rewire. So we've done that, and let's continue now because again, of your experience, both with what you're doing right now, author, thought leader, entrepreneur, investment banker, you've coached founders, you've seen founders through exits.
You've seen burnout. You've seen reinvention. What I'm wondering, generally speaking, and you'd be bang on to say, Jeffrey, well, there is no, generally speaking, every entrepreneur has a unique journey, a unique path. But generally speaking, what would be the silent crisis, and I'm using that deliberately, the word crisis.
What's the silent crisis that most entrepreneurs that you're dealing with, that you see them face, but is rarely talked about, if ever.
Rand Selig: Well, it's, the paradox of having created something of value [00:37:00] over some period of time. Feeling good about that and having your identity tied to that at the same time thinking, well, what's next? And shrinking and feeling very nervous. And nobody's gonna really be interested in me.
Nobody's gonna be interested in what I have to offer. Can't learn. I, given my age or whatever I can't pick up something new. I have accumulated power, but that's sort of authority power. I don't know how to create the power that has to do with people genuinely being interested in me and liking to be around me just because of me.
A lot of introspective sort of look that says, I don't know if I can do it. So in some cases that means they're holding onto their company for much longer than they In some cases it means that they have their bucket list, which is to travel and do some house projects and get the golf game going, and they think that's enough.
[00:38:00] And it, it is good for a while for sure. A lot of people need to kind of just get, pull away and, recharge in a fashion, but you don't recharge to just then sit around, you recharge to do something. So there's a, there's this sort of paradoxical accomplishment on the one side and confidence and in the other hand.
An unknown, a series of unknowns and the risk taking that might've existed in the, running the company or being involved in some position in the company. Those risks were understandable risks, so you could see other people doing this other new thing. I don't know. This sounds very scary and risky.
I don't know. I don't know how to embrace that. I don't know what to do about that. I think a lot of people look at this question of thriving and they think to themselves I don't need to worry about that anymore. I've resigned myself to this sort of level of being a six or seven on the scale of 10, and that's just the way life is.
And when I [00:39:00] say I don't believe it for a moment, and I'll tell you why. They wanna hear that. They wanna understand what I'm talking about. and I have my own personal story to tell, plus many other stories from other people I've seen and worked with.
Jeffrey Feldberg: My goodness. So much personal history there and experience both yourself, your clients. And let me ask you this before we start going into wrap up mode. Another somewhat of a personal question. When you're writing thriving, was there one chapter for you, Rand, that you struggle with more than most to write?
Rand Selig: Well, I should say it's just a way of background. This four foot stack of papers had lots of really great articles that made copies of little quotes that I'd come along the way with my own thoughts on many subjects. And so I wanted to go, went through every single page in that four foot stack to see does it belong in the book and where in the
book.
I'm very delighted. The book, as I've just finished the last [00:40:00] chapter of the audio book that I've recorded myself people said that's the way to do it because you know what to emphasize and, we like your voice. Say that one of the hardest for me was not sort of the content element of it, but the tone of it. the first half of the book is about thriving personally. And there are all these different dimensions that includes building character and money and, a series of emotions that are important. Gratitude, having purpose and meaning. But there's also one on spirituality and religion.
I was very nervous, I was very nervous about that chapter because I make two statements, very strong statements. I said, one, I think if you're gonna be thriving, spirituality a must have, and what I mean by spirituality is to be in awe. And to be humble and the higher you climb up this little ladder of life, the more being humble and being in awe [00:41:00] of this amazing world.
The way I get into spirituality more often than not is out in nature. So I think that's indispensable having spirituality. But the other part of it is religion. And I make the statement that if religion works for you I'm happy for you. It does not work for a lot of people. Religion to me should be about opening your heart, not closing your mind.
And so I talk about that. I got nervous. I like what I've written, I did a lot of reading about this. I had my own personal experiences with it. And I was very nervous 'cause I wanted my book to be available to everybody. I didn't care what religion you followed or didn't follow.
40% of people in the United States check off the box. None, no religion. that's where things are. That's the reality. And you go to a place of worship and it's not filled the way it was 10, 20, 40 years ago for sure. So I make a very strong statement [00:42:00] about that.
And I say, if you have religion, have it be one that works for you. A religion of your own. fact I refer to a book by that name. Very good book. And so the nervousness came is the right tone about that, because I wanted to engage everybody. I didn't wanna exclude anybody.
Somebody says, well, I liked most of the book, but then I got to that chapter and I threw it down on the ground and I'm not gonna read more of it. I didn't want that to happen. but I got through that and I did change some of the tone and tone in other places too. I didn't wanna come across as a person who knew all the answers.
I don't I wanted to create possibilities for people and inspire them and encourage them my readers in the early stage in the manuscripts and now with so much feedback so much incredible feedback reviews and people, telling me, bumping into me and saying, I know your book.
I loved it. Thank you. I say, well, what part did you like best? And they'll go on. I kind of look at my [00:43:00] watch, have to go. I can't, but here, email me. We, can you pick it up more later? it's been a absolute joy. It's my purpose for writing a book is coming true.
It's helping a lot of people. There are a lot of headwinds, whether you're in business or just in life in general, and it's easy to get stuck. It's easy to be confused. Life is a series of beginnings and endings, and in the middle of transitions, they can be very complicated. I talk about those things in the book, so
Jeffrey Feldberg: I love, what's there, and this is sounds like a journey, as much joy for you of putting this together with the book as what is ahead for the reader. Going through that again, deepp Nation, when you go to the show notes, I. Click on the links, pick up the book, and by the time this episode comes out, hopefully the audio book is out as well.
And pick up the audio book and listen to that and learn and listen, because Rand is from the trenches, a fellow entrepreneur, mergers and acquisitions, mal coach, thought leader, author. [00:44:00] He's been where we are, and he's been down that path and has a little bit more experience than we do that he can share what's ahead for us and how we could perhaps skip over some of these speed bumps that lay ahead and get to that thriving kind of state.
And Rand, I like how you built into that. Some people get turned off by this spirituality, which in my books is very different than organized religion or religion in general, but spirituality, and to me, that's played a big part in my life. And all the times that I've turned away from that have been some darker times in my life.
And when I've come back to it, and welcome in my case, God, back into my life. Wonderful things have happened and I'm right there with you. And so Rand, before we go into the wrap up mode, which is gonna be another kick at the can for you, because we did it once before and you were brilliant with that. Is there a question, and I know there are so many questions that I haven't yet asked, is there a question I haven't asked or a topic or a theme that we haven't covered either the last time we spoke or [00:45:00] together just now that you'd like to put out there for Deep Deep Wealth Nation?
Rand Selig: wanna mention, we did touch on this, I think the first time, and again today a little bit. But I just wanna really shine a bright light on the importance of relationships. This is the absolute glue in life. People often ask me what is success? How do you define success?
Did the people that you work with and you sold their companies, were they successful? And I go, in so many cases, the people that I added more wealth to their re pile of investments and so on. But I gotta say, I don't think in some cases they were successful. Why? Because just at least one thing, their relationships broken.
Broken relationships with partners with, in their personal lives, with families people not talking. This is not successful in my, and I have a very high standard for this. So relationships, the, so you have the relationship with [00:46:00] yourself. You gotta know yourself.
there's no substitute for loving yourself. the relationship you have with yourself is the most important relationship you'll have in your entire life. Buckle down with that one, relationships with yourself. Then this question of. Relationships with others. And there's a way to build and deepen and create an enduring set of relationships with people.
I've been doing that, I've been doing that for a while. And boy, it takes some work. I have a list, I go down the list of really key relationships with friends. These are or colleagues. There's a list of course, of the family that it's not a big family, so it's not an overwhelming thing.
But I go down, I say, I haven't heard from Phil in a while. And last time we talked about three months ago, he was just going through this really interesting business thing. Let me check in with him, see how that's going, see if I can, be of any help to him. He's a great guy. And I'm hoping it's all gonna be a good story when we check in.
[00:47:00] So I go through that, some of these friends and colleagues are not local, so it's an email, it's a, occasionally a Zoom. It's a phone call. Others are local and I'm saying, when's their next coffee or they're reaching out and saying, I wanna have lunch or coffee with you.
Building relationships, making them valuable to you and valuable to them. Again, this focus on someone else rather than yourself becomes really key. So relationships with others becomes an absolute gift that you can give yourself. And there's an architecture for yourself and for others that makes these relationships you know, valuable.
Even magical. And I talk about that. there's several chapters in the book talking about relationships.
Jeffrey Feldberg: And so really what I'm hearing here, and you wouldn't expect to hear this from a business guy, which I put you in that category very deliberately, a successful business individual and entrepreneur. Go within, be honest with yourself, build out [00:48:00] those personal relationships, your own personal network so that you can thrive and enjoy the journey along the way.
And speaking of the journey, Rand, as you're going through that, we're about to go into wrap up mode. But before we go into wrap up mode, any after thoughts on what we've just been talking about?
Rand Selig: Well, do, it wouldn't be a complete point I'm making about relationships, but I didn't talk about relationships at in workplace, a lot of people say it's all very transactional and my job is to be this, and those people above me are below me or in a different thing.
I don't have a relationship other than sort of a more formal one, and I push back on people with that, People are gonna do better and they're gonna enjoy the time better if they have a relationship. But on Monday morning you say, Hey, how was your weekend? But ask it sincerely, and you don't have to be waiting to, for you to talk about what you did.
If they wanna know they'll last, that's okay. But you just generally are interested in what they're doing. There's [00:49:00] managing up with bosses, I can do a better job, boss if I have these resources. I wanna do a better job. I wanna, contribute more, but I need this, I need that. Is that something you can help me with?
Those kinds of managing up conversations really valuable. And peers also. It doesn't have to be competitive, it doesn't have to be, I get the promotion or you do and not both of us. And so I'm not going to share my treasure tove of ideas with you 'cause you're. You're competitive or you're a threat.
So there's a way of handling that with relationships too. Again, something I talk about. Self friends, family colleagues at the workplace, relationships all around us embracing like a warm hug.
Jeffrey Feldberg: Yeah. So much to that you're really bringing. In the human element. I'm not hearing profit, I'm not hearing money, I'm not hearing accolades and success. It's more on the personal side, which is really interesting because when we started off the [00:50:00] conversation, it was all about the personal side. Hey, let's get the personal side right first, let's thrive personally, and then that will spill over onto the business side so that we can thrive.
And actually it's a perfect segue as we go into wrap up mode. Now, so you've done this before, you're an old pro. I'm gonna refresh your memory of our favorite question here. It's a tradition here in the Dupa podcast where every guest, including repeat guests like yourself, friend, are asked the same question.
And the question is this. When you think of the movie back to the Future, you have that magical DeLorean car that will take you to any point in time. So imagine now it's tomorrow morning and you look outside your window. Rand, this is the fun part. Not only is the DeLorean car curbside, the door is open and it's waiting for you to hop on in what you do, and you're now gonna go to any point in your life, Rand, as a young child, a teenager, whatever point in time it would be.
What are you telling your younger self in terms of life lessons or life wisdom or, Hey Rand, do this, but don't do that. What would it sound like?
Rand Selig: Well, if I could bring [00:51:00] who I am today back into the car and zoom back I would certainly be a lot more mindful. I had a boss early in my career. He said, you're never gonna have to worry about making money. You've got a lot of talent. Where you need to focus is on the journey, on the process that engaging people, the people who are working for you, the people who matter to, not necessarily the outcome, but to how they feel and how you feel about it.
Being more mindful, being more prepared to be in a conversation with somebody like my father. Or maybe people on my teams where I, they were tough. They were tough relationships. And I didn't handle that at that time the way I know I could today. And so thanks for the DeLorean car and bringing the more mindfulness into it, the more confident sense of I don't have to have [00:52:00] the answers.
I can have questions and I can ask questions like Dad. Is there another way that we could handle that so that the, even though I broke your rule in the rule book the consequence isn't quite so severe because I do understand why I'm supposed to be doing it. But can we have that conversation? And certainly didn't know how to have that back then.
Jeffrey Feldberg: I love that. And so if you're to take that wisdom that you shared with me, and if you were to distill it into a sentence to the younger Rand what would that sentence be?
Rand Selig: trust that the world is gonna work out. Just fine. And smile a little bit more. Be a little more relaxed. Don't be afraid that you're not, gonna be successful. That you're, the outcome that you want isn't gonna be there. It's gonna work out. Life is good.
Jeffrey Feldberg: I like that Trust that everything will work out. Smile. Life is good. And what's interesting, although you [00:53:00] didn't explicitly say it is built into it. Have some faith. Some terrific wisdom.
Rand Selig: Thank you. There's just no substitute for believing yourself no matter, how untied your shoelaces are. You believe in yourself. I think it was Martin Buber who said God is not in us individuals. God is in the relationship between two people. And so we manifest that in lots of different ways.
We can manifest it at the workplace. And I'm not talking about having a prayer session at the workplace because that's going to exclude some people who feel uncomfortable. I'm not advocating for that at all, but what I am saying is we can build relationships, and by my definition, by building those relationships in every part of our lives.
We're bringing that great, beautiful spirit in into the world.
Jeffrey Feldberg: Love that. And Rand, for a listener in the Deep Wealth Nation, they have a question [00:54:00] for you. Maybe they want you to come and speak to their company or their association or organization, or perhaps even some coaching. Where would be the best place online for someone to reach you?
Rand Selig: Thank you Jeffrey. The best places is just go to my book website www.randseig.com, R-A-N-D-S as in Sam, ELI g.com. There are many pages we're gonna add a couple more pages for audio listeners coming up, but there's a page it says, connect. Connect with brand and you can put in something about, Hey, we'd love to have you a speaker, or I have a question about something you wrote in whatever chapter.
Or here's what I appreciated about your book or what, whatever. You can just write a thing to me. I will get that in. It is there in the, book website, but then it becomes an email directly to me at my personal email. Then I can respond that way. So it's a very convenient flow. And I welcome that.
Absolutely. And that's why I'm here. That's this [00:55:00] submission to engage people.
Jeffrey Feldberg: Love that Deep Wealth Nation. It is effortless, it's easy. Go to the show notes. It's a point and click. It's all there. Pick up the book, pick up the audio book, reach out to Rand, have that conversation. You'll come out of it a whole lot more. I'm gonna say happy, faithful, and experience. And when you came into that Rand that said, congratulations, this official, once again, this is a wrap.
And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. Thank you so much.
Rand Selig: Thank you, Jeffrey. It's been a pleasure.
Jeffrey Feldberg: So there you have it, Deep Wealth Nation. What did you think?
So with all that said and as we wrap it up, I have another question for you.
Actually, it's more of a personal favor.
Did you find this episode helpful?
Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey?
And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.
Are you ready for it? [00:56:00]
The dramatic pause. I'll just wait a moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.
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So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.
And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe.
Thank you so much.
God bless.

Rand Selig
What if success wasn’t about how fast you scale—but how deeply you connect?
Rand Selig has spent over four decades guiding some of the world’s most recognizable brands and growth-stage companies through critical inflection points. As the founder of Selig & Associates, his approach goes beyond business strategy—it’s about helping leaders find clarity in chaos, purpose in performance, and alignment between who they are and what they build.
He’s advised Fortune 100 executives, private equity-backed CEOs, and founders on the brink of massive expansion or meaningful reinvention. But Rand isn’t the loudest voice in the room—he’s the one people listen to when everything is on the line. His gift isn’t just insight. It’s discernment.
Rand’s journey has been shaped by curiosity, listening, and a rare ability to ask the question behind the question. He believes leadership is an inside job—and that sustainable growth only happens when leaders are willing to look inward before scaling outward.
This is a conversation about the human side of high performance, and what it really takes to lead with conviction when no one else can see what you see yet.