Wall Street Investment Banker Rand Selig Reveals the Dark Side Of Success And How To Crack The Code On Health, Happiness, And Purpose (#442)

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! “Learn from those around you that you love and respect.” -Rand Selig Exclusive Insights from This Week's Episodes Rand Selig was a top Wall Street investment banker with over 250 deals under his belt, a Stanford MBA, and a thriving firm named one of the be...
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“Learn from those around you that you love and respect.” - Rand Selig
Exclusive Insights from This Week's Episodes
Rand Selig was a top Wall Street investment banker with over 250 deals under his belt, a Stanford MBA, and a thriving firm named one of the best in the Bay Area. In this powerful episode, Rand shares the dark side of high performance and how the very systems that create success can also destroy fulfillment.
00:02:00 How Rand Selig went from Stanford MBA to Wall Street banker
00:05:30 The life-changing advice Rand’s mentor gave him—and how it reshaped his path
00:08:45 The red flags entrepreneurs miss when chasing growth
00:10:15 Why knowing your post-exit life is more important than the deal itself
00:13:00 The pivotal decision to build a firm based on life principles
00:18:00 Why thriving starts with character, self-awareness, and emotional mastery
00:26:00 How Rand Selig redefined success after burning out
00:35:00 The one transformational question every entrepreneur should be asking
00:44:00 The conversation every entrepreneur must have—before and after a liquidity event
Click here for full show notes, transcript, and resources:
https://podcast.deepwealth.com/442
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442 Rand Selig
Jeffrey Feldberg: [00:00:00] What happens when decades of leadership in corporate America collide with a deep desire to help people live more meaningful lives at work, home and beyond? Meet Ran Sig, a former high powered executive turned transformational coach, and the founder of Momentum Coaching and Consulting with a background that includes executive leadership roles at major firms like the North Highland Company.
Rand spent over three decades driving growth, building high performance teams, and navigating the complex business strategy and operations world. But Rand's journey didn't stop at success in the boardroom. Guided by a passion to unlock human potential, Rand now helps leaders and organizations create lives and workplaces rooted in purpose, alignment, and lasting impact through its proprietary momentum, methodology, and decades of hard won wisdom.
Rand supports CEOs, entrepreneurs, and rising leaders in transforming their results and their relationship to success. [00:01:00] Rand's work bridges strategic excellence with soulful clarity from coaching founders through major transitions to helping burnt out executives rediscover joy. His belief you don't have to sacrifice your wellbeing to build something extraordinary, and when you align your personal and professional values.
The results are exponential. Today, you'll hear the powerful story behind Rand's Pivot, his lessons from corporate highs and personal reinventions, and his insights into how leaders can unlock their next level of growth, not just in business, but in life.
And before we start the episode, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. Here's Sanjay, a graduate of Deep Wealth Mastery, and he says, the investment I made in the Deep Wealth Mastery Program, it's a rounding error compared to the value created today and the future value I'll receive.
Or how about William, who says, and I love this, A company that's attractive to sell is also a great one to own. The Deep Wealth Mastery Program gives me the best of both [00:02:00] worlds.
Now speaking of growth and adding value, check out what Leon says. He says that the Deep Wealth Mastery Program changed how and who we hire. We've now begun to hire talent today that we never would have hired if it weren't for the program. The talent we're hiring today is helping both increase our growth and profits and our future enterprise value.
Man, I love that kind of feedback because it's that kind of feedback that's what gets me out of bed every day.
Deep Wealth Mastery System, 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, created a system that we now call Deep Wealth Mastery, and that's what helped myself and my business partners all welcome from a different buyer, a different offer, a nine figure deal.
So if you're interested in growing your profits, preparing for a future liquidity event, whether that's two years away or 22 years away, and if 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 [00:03:00] deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as the Scale for Ultimate Sales System.
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. Whether you're a startup, whether you've been in business for three or four decades, whether you're manufacturing, whether you're high tech, SaaS, low tech, whatever the case may Come in and network with other business owners, with other businesses, just like you, because they all want to lock in their financial freedom and enjoy both success and fulfillment.
Again, 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. Please send an email to success at deepwealth. com.
Deep Wealth Nation, welcome to another episode. Let me ask you this. Are you surviving? And if you are, do you wish you're thriving or are you thriving and you wanna take it to the next level? And if you are thriving, I. Are you doing it across all areas of your life and dollars to donuts? I'm not a betting guy, but dollars to [00:04:00] donuts is probably, no, it's not all areas of my life where I'm not even thriving.
Well, you've come to the right place of how you're gonna come outta this episode a whole lot better. We have a very special guest in the House of Deep Wealth. Rand, welcome to the Deep Wealth Podcast, and absolute pleasure to have you with us. There is always a story behind the story. Rand, what's your story?
What got you from where you were to where you are today?
Rand Selig: Jeffrey, thanks for having me. Be your guest today. I have a, good story. I'm happy with my story. Starting actually in high school, I decided that being excellent and everything I did was important. So became an excellent student. I went on to college have a degree in mathematics and psychology, and then I went on and got my MBA at Stanford.
And while I was at Stanford, I. I had a mentor and have to tell your listeners, having mentors, no matter where you are, whatever stage you're at in your business or in your life, having a mentor is just a sensational thing to do. wish I'd had more. I had several really good ones.
So my mentor in business [00:05:00] school was Alan and Tovan. Alan and Tovan was Robert McNamara's number two throughout the entire decade of the 1960s at the Pentagon. And he was building a course which I was helping with, which was the cost benefit analysis in healthcare for medical students and for business school students.
And one day he's a super smart guy, a Rhode scholar. He's tapping his pencil on his desk. As we're creating more thoughts about this course we're creating, he says, by the way, what are you gonna do when you finish the program in June? I said, oh, well, I'm probably gonna go back to Washington dc I've spent some time there before going to business school and policy analysis is really what I'm very keen on.
And he said that's an interesting and important area. And who would you work with? And I said, well, probably one of McKenzie or Booz Allen, one of those. And he broke his pencil. He threw it at me and said, no. You are much more action oriented [00:06:00] than that. You know what they do with those reports?
They file them in the circular file. You have to go into investment banking. Do you know what that is? And I said, well, professor Ovn, I do. I'm a good student. And I had several friends who went to Wall Street last summer and he says, well then great. Go look into it. So that opened up an entire arena that I had really not considered at all.
I didn't think of myself as a Wall Street kind of person. And I had, a number of very nice offers and I decided to go to Lehman Brothers, which is in the history books. It was a great choice for me to become an investment banker. It took me a dozen years actually to realize that I wanted to stay as an investment banker, but on my terms, I didn't wanna be part of a big firm.
I didn't like meetings and I usually didn't like my boss. I wanted to live and die by resort. I wanted to. Be able to pick my clients and I wanted to pick the area of focus and services that we'd be [00:07:00] offering. so it took me a little while and a lot of thinking, so I set up my firm based on a set of principles, which I adhere to the entire time, over three decades now.
And the results have been fantastic. Last year, my firm, the State Lake Capital Group, was named the best sustainable investment banking firm in the San Francisco Bay Area, which is a really nice feather in our cap. So that's a bit of the story.
Jeffrey Feldberg: Absolutely love that story. And Deepp Nation. Before we go further, if you go to the show notes, pick up Rand's book, thriving, how to Create. At a healthier, happier, and more prosperous life. And I tell you the way, Rand, that you put that all together, we're gonna talk about that momentarily. I just love how you broke that all down.
It is really not just a book, but it's an instruction book for life in terms of what you've done and how you've put all that together. I wanna go back to your investment banking days for just a moment, because after all, this is the default podcast and we're talking about how we grow my business and profits today, and how I can exit tomorrow.
You've been on all sides [00:08:00] of the table, and I suppose the question I'm gonna ask, we could flip it over and give us the inverse of that, and perhaps we'll do that, but let's take the glass half full. When you look back at the deals that you worked with, the entrepreneurs, the companies that they just hated out of the park.
Were there some common themes or attributes or even poodle's law, Hey, yeah, Jeff, you know what? 80% of the results that these companies got, it came from these 20% of the strategies or the actions they were taking. They worked really well for them. Any insights on that of what you saw from the world of m and a?
Rand Selig: I've had the good fortune to have completed over 250 corporate transactions of all sizes, but, in the mid-market arena, primarily because that's. I think a lot more fun. I'm dealing with real issues. I'm dealing with owners of companies not the financial chief financial officer, and I would say that the ones that really stand out to me most are the ones who I.
We're [00:09:00] open and willing to embrace the conversation about objectives. What are you really trying to accomplish? That is absolutely in every case, our starting place. And I would say that from my experience with several of the major investment banking firms, that's overlooked and skipped. They're just gonna dive right into the transaction.
Chaching, they wanna get their fee the most the speediest way they can get there is better. I believe that it's critical that I understand what my client's objectives are. And that includes a lot of personal things, not just the financial side. It includes things like what do they wanna have happen to their employees?
It has to do with what role they wanna play, if any. Going forward. And we use those this is in many cases the first time somebody's really been asked that question because it's not about how are you gonna grow from, here to there. It's about who are you and you've created something valuable.
[00:10:00] What are you gonna do next? How can I help you with that? So this conversation about objectives we come back to. Throughout the course of the transaction. It's kind of a litmus test, if you will, because when we get to the place where we're now ready to launch and start contacting potential buyers or potential merger partners I bring out this set of answers again.
And when we're in front of a buyer, or after the buyers left, we returned to that. Did this buyer qualify based on our objectives? Yes or no? Or maybe if it's a, maybe, what further questions do we need to ask them? So what I've engaged most effectively, and which I'd say I always engage on this and has always been good, but the ones that have been most effective, my client lights up and says, I've been waiting for you to come into my life.
Thank you.
Jeffrey Feldberg: Very interesting what you're sharing. And actually it's been my observation as well. I'll put myself under the microscope and then take it broadly out to [00:11:00] the deep wealth community, deep wealth nation. I know for myself, Rand running my business really wasn't thinking beyond. Tomorrow, what's tomorrow gonna bring?
And then I get this knock at the door and we have a very valuable enterprise. But I was so busy doing everything else, I didn't really realize that. And it was a ready, not aimed in fire, but ready, fire, aim. And as the Deep Wealth knows, had we said yes to that first offer that came in the door, which was a seven figure offer, and nothing wrong with a seven figure offer.
Unknowingly, we would've been saying no to the nine figure value, the enterprise value that we had created that was there for us. It was just out of sight. So I couldn't agree more of, Hey, what's your North Star? Both in business and in life. I know you talk about that in the book a lot as well of what's going on with where you want to be and what you wanna do.
And actually it's a perfect segue for your book on thriving. And I'm wondering, when I started to go through it, I couldn't help but think. Rand for you, what was the personal turning point that [00:12:00] inspired you to write thriving, and how did that moment shape the message of the book?
Rand Selig: Well, beginning in high school I started collecting articles and making notes about things. I collected quotes and so in my office I had this four foot. Stack of papers. And I kept on looking at this over the years thinking there's several books in that pile and there's several books inside me. And so starting uh, four years ago, I said, now's the time, now's the time for me to really get busy.
And it took quite a while, several months to. Chunk, the four foot pile into files folders which ultimately became the chapters in my book. Along the way more than just being running my own firm which has been great. I mentioned that I. Built my company based on a set of principles.
And the principles include being able to live and work in my community. I didn't want to have a big commute. And if somebody said, oh, you don't [00:13:00] have a financial district address we're not interested, I'd say, I'm delighted to hear that because if that's what's most important to you, I'm not sure I wanna be, working with you.
I wanna work with somebody who cares about quality and substance and follow through and great communication. So, this book came from a lot of thinking about who I was as a walkthrough life, more than just being this founder and CEO of a company. I was also on 18 boards in my career.
I was a little league coach. I was a scout master. I got involved with a lot of environmental. Projects, not just on the board, but rolling up my sleeves to do the work, which is a lot more important than being a talking head sometimes. And so I had a lot of experiences with people in all stages of life in different ages.
And I realized there were a lot of sticking points that people were confused troubled a lot of pain. And I thought, okay, this is the time to [00:14:00] bring out in a very positive way, I'm relentlessly positive. A roadmap for how to go forward and create a life that is fulfilling the life that reaches your potential as best as possible.
life that allows you to get up in the morning and say, I'm ready to go. I'm excited about it. I tell people, and I've told my clients this over many years, don't retire, and they look at me and say, well, what the hell are you here for? I said, well, I'm here to help you do the transaction we've talked about.
But after that, there is another chapter for you. There is something else. So don't say retire, say rewire. Become another person. Build on top of all this great stuff you've been doing for quite some time. And I. Look into it. And in fact, many conversations I've had with people say, well, I'm afraid of selling.
Alright, we've got the deal done. I, all I now have to do is sign it. I'm a little anxious and I go, let's talk. What's going on? I says, [00:15:00] well, I don't know really who I am. I said, well, we have talked about this of course. So I just want to suggest that you lean into those kinds of things that have given you.
A sense of purpose beyond this company that you've built. What are your interests? What kinds of books do you like reading? When you do community service, and we've talked about that and you've begun doing that what are those areas? These are doors that you can knock on to create this new you, this rewired you.
Jeffrey Feldberg: So interesting that you talk about that and the post. To life, as we call it here at Deep Wealth and in our flagship program, deep Wealth Mastery. That's really the ultimate exit, and that's actually ran should be no surprise to you. That's where we start. So when you go through the 90 day program, day one, we're actually talking about, okay, imagine you are no longer part of the company, the company's no longer part of you.
What does that look like for you? Where do you wanna be doing? Because I'll share with you R and I'm sure. You'll probably agree with this. You'll let me [00:16:00] know. Jeffrey OnBase off base, at least for me, my post exit life that was. Very much an unhappy part of my journey. That's where I made all the mistakes.
Postex exit, not Pre-Ex Exit, because I lost my purpose. I lost my North Star. I didn't know what I should be doing. And believe you and me, no one feels sorry for someone. Lots of zeros in the bank account sitting at home in the pajamas, bored outta their mind that no one wants to come out to play because they're living their lives.
They're in their careers or building their companies, whatever the case may be. Well, that was me and finally was able to get through that. Wow. Looking back, the younger Jeffrey, I could only wish and hope that the advice that you shared in the book and what we're talking about right now, I would've taken to heart.
And speaking of the book, when I went through the first three chapters, to me this was a really important triage because you could have started anywhere. I. But you started with, well, number one, I want you to build your character. Number two, let's look at the relationship, not with other people, but with ourselves.
And then in chapter three, well, how are we gonna manage ourselves? You don't hear that a lot [00:17:00] in business, but you started there. Those were the first three chapters that you began with. Can you share with the deep Deep Wealth what was going on there? That's where you really decided to kick things off of, Hey, what's your character?
What's your relationship with yourself, and how are you managing yourself?
Rand Selig: Well, I think people uh, tend to skip over, especially if they've accomplished something and they've got a, an important title and set of responsibilities that they think are, are good ones. They say so well, I know myself, I know my preferences. I know you know things that I'm good at and, I kind of know that I.
And I think that's true. I think nearly everybody who's a serious person can answer some of that. The truth of the matter is that we keep involving, who we were five years ago is different than the person we are today. And of course, the world around us is very different. And the deeper dive around who you are, what you will stand for, and what you won't stand for what kind of environments are really best for you.
What kinds of [00:18:00] things do you really, are you best advised to get support around? Whether it's emotional kinds of things or it's the work kind of environment. People don't leverage themselves nearly enough. I mentioned not having enough mentors this kind of thing. So those first three chapters in my book are really anchoring.
To me there's absolutely no substitute in creating a thriving life other than to do that, get to know yourself, become really self-aware, and then stay with it. Keep enjoying yourself. I say the most important relationship you'll ever have in your life is the one with yourself.
And if you can get to the place where you know yourself well, you appreciate, maybe even love many aspects of who you are and the parts that you don't think are just as rock solid as the others, then mark them as places you can grow and evolve and be committed to that. That creates something so valuable.
It's inspiring to other people as well, whether you're working with them or [00:19:00] just, creating some kind of a friendship relationship with them.
Jeffrey Feldberg: Words to the whys in terms of what you're sharing there and, and I'm wondering when we look at those first three areas. And because here on the Deep Wealth Podcast, our tagline is helping you extract your deep wealth, both in business and in life. So both on the personal side as well as on the business side when we're looking at the character of us and the relationship with ourselves, and really managing how we're interacting with the outside world.
Love your thoughts on base, off-base. I could have the best service or product in the world. I can have the most incredible team in the world. But if I'm not showing up firing in all cylinders, I'm gonna be losing my competitive edge. I may not be getting the absolute best out of the business out of life that I could because on the personal side, I have some issues there.
Thoughts about that? I.
Rand Selig: Yeah I, think there are a number of hallmarks of people who are very centered. Who are accomplishing a lot, who are surrounded by high quality [00:20:00] relationships, deep and enduring relationships. I think one of those things is having integrity and integrity basically means that you do what you're saying you're gonna do.
Your word means something. Then when you say very casually, oh, I'll send you the link to that, or I'll email you with the name of that book that I just mentioned. You actually do it. You know, Just sort of drop the ball, you follow through. Now this applies in life, and of course it applies in business when you can deal with somebody in the business arena who follows through that way.
Wow. It you don't have to keep following up. You don't have to keep. Same stuff. What was the name of that book? I can't remember it. And dang, I wish I did because it sounded like a really good book or whatever the situation may be. So integrity becomes really important.
There are many elements associated with integrity. Being honest would be another. I talk about the importance of having a legacy and living it, knowing what your legacy is. I'm very big on writing stuff down, partly [00:21:00] because I think by writing down you see what's missing. You see inconsistencies you can't just think it through by yourself.
And so writing it down becomes another roadmap in a way. So, a legacy to me is one of these things that when you get clear about it doesn't have to be perfect and it does change over time. But I talk about my legacy being based on four things. One is excellence, which we talked about a few minutes ago.
Another is having purpose. All the way to the end. The very last bit of your life, having purpose, even if your purpose is just being kind and being respectful and being interested in somebody else being encouraging these kinds of things. A third one is, being the kind of person where you are, in essence being love.
It's not the romantic thing I'm talking about here. It's the kinds of qualities of respect. Caring [00:22:00] and concern, and you're doing that not with the necessarily only the people closest to you in life, but the people you, meet and you know, sitting next to you while you're having a cup of coffee.
it could be the person who brings you the cup of coffee and you say, oh, thanks. This is really great. I really appreciate make eye contact. And then you say, and by the way, what's your name? All of a sudden everybody has their story and everybody wants to tell their story and be seen and appreciated for who they are.
So, having a legacy and then living it, knowing what, who you are and what you're about is absolutely invaluable. You can grow, you can, be happy which isn't, a lot of people get stuck. They don't really understand what happiness is. A lot of business people, I think think of happiness as having more toys.
Well, I hate to tell your listeners that's not a great answer.
Jeffrey Feldberg: Yeah. So much easier. And I've found Rand that the key to all this in terms of. Speaking to people offering to be of service. Or some people say, going the extra [00:23:00] mile is that I'm doing this because I'm not expecting anything in return. It's not a quid pro quo. Well, I'm gonna help you only because you're gonna help me.
I'm just gonna help you because, and you have no expectations. And if something else comes outta that, that's great. But if nothing comes outta that, that's fine as well because my expectations are, I just wanna be helpful. And back to your earlier point about integrity. I find that today, particularly with social media out there.
There are so many people that just aren't integral and for us to step up to the plate, it costs no more money, no more time that we can be integral. We can have that integrity. We really stand out from the crowd and it's so much easier and so many ways to do that now because so few are doing it that we can really send out, add some value, and just.
Change someone's life or make a difference, or have someone smile or just be of a resource or of help. So I wanted to ask you as we're talking about that, when it comes to the entrepreneurial world, we're type A, we're chasing prosperity, but [00:24:00] oftentimes when we're chasing the rich life, after we've sold our business for a gazillion dollars, we're often forgetting about health and happiness.
How do you help people reconnect with what actually matters?
Rand Selig: Well, I think people who are most conflicted around this have some kind of external set of yardstick. They're defining success by looking outside at what a neighbor I. Is doing well, the neighbor's driving down the, the street in a brand new swishy car, or you're talking to a friend who just came back from a really terrific vacation, which of course is very expensive.
Or somebody's talking about remodeling their house even though their kids have now left and they're empty, nested, and they're all are all kinds of ways that people can look. Out and say, oh, maybe I should do that. Maybe I could use my financial resources in that way. And I think that doesn't produce the really fulfilling happiness that a lot of [00:25:00] people are really looking for.
I think it has to be an internal yardstick, and each of us is different. And that's terrific. That's what makes the world so interesting. So by looking inside, you say, well, what does make me happy? Is it being by myself or is it being with others? Is it being in nature? What am I doing?
Do I like animals? how am I doing financially? do I have the kind of advisors that I need who are giving me the information I need so I can make good decisions and sleep well at night, not be anxious when the markets are in turmoil? there are a lot of elements to that.
I think having relationships. Is absolutely key. I have met many very wealthy people and I helped them become, more wealthy along the way. But I would say a lot of them were not successful. lot of people say I'm shocked when you say that. I say They're not successful because look at their relationships failed all around them.
Their business relationships they've exited partnerships. their family relationships. Look at what they've done with [00:26:00] themselves. They've not taken care of themselves. They've been so. Obsessed almost with running their firm, that they didn't take time to take care of themselves with the right nutrition.
They're not sleeping well. There are a lot of these things, so are they successful? I have to say just my definition, my explanation but in talking to 'em I feel that's a big missing. A, A big hole in the donut right there. So there are a lot of things that we can do by looking inside. This is back to the knowing yourself.
And I'm saying this is who I am who I'm becoming. I'm looking forward to being that better person being the note taker. I am, I can look back at periods of time in my life where I was not the person I am today. And I'm a better person. Today than I was before. And I'm a better, and I'm a better executive as well because I bring the full me, I bring the kindness and respect.
When I show up at a meeting [00:27:00] before I launch into the big agenda, I say, lemme check in. How's everybody doing? Hey, George. What's that? You don't look like your normal smiling self. What's going on? You wanna talk about that? I'm always available to you, but if you wanna share what's going on right now with the group let's do it.
That's who we are. We're building relationships with each other, and I can bring that out. I don't have to feel like the agenda of getting, so much done in 45 minutes is. The most important thing, the most important thing is that we become a team and that we're committed to what our vision of the organization is, and we're aligned in.
Jeffrey Feldberg: Love what you're saying there. And actually as you're speaking, and I know in thriving you talk about, well, we need to redefine what pro. Is, and you just redefined prosperity for us and for me, it's actually a perfect segue into someone goes through this book now and again, you both nation, go to the show notes, pick up the book, it's a link there, it's a point and click.
It doesn't get any easier. And start reading, pick up Thriving, how to create a [00:28:00] healthier, happier, more prosperous life. The one question I have for you, Anne, when we start to implement the Thrive framework that you've begun to describe for us and that you fully talk about in the book itself. I'm wondering what would be a common mistake or a few common mistakes that we're making along the way when we're trying to implement the thriving framework.
What would you want us to know?
Rand Selig: Well, this is not for the weak hearted you have to be committed to yourself. You have to say, Hey, look, I've made mistakes along the way. You have to say, this is hard work, and I'm a little tired. Forgive yourself for not being able to do it all in one big. Giant gulp. It's little bits.
It's little steps. great book I read last year, atomic Habits, and that's one of the central points here. Little steps to build new habits. But you have to know what your good habits are, and you have to know what your bad habits are. Back to knowing yourself. So, I think people get stuck because they're trying to bite off too much all at once.
They're not listening to themselves. They're listening [00:29:00] maybe to a spouse, maybe to a good friend maybe even a mentor somebody who they want to carry the favor of.
By denying themselves their own sense of self, that's gonna be really hard to thrive. talk about thriving in four different aspects. The first, which you've been talking about thank you. Jeffrey is thriving personally, and that's half the book. It is that foundational, but then it goes from there into thriving with others. I. Thriving out in the world by being charitable and of service, being philanthropic taking all that you've learned and applying it and then thriving as you move ever forward in life.
This is the gaining wisdom We all have. Wisdom, gain more of it, and then evolve. Commit to becoming the better person. you know, Hemingway once said. Nobility is not being superior to another person. true. Nobility is being superior to your [00:30:00] former self, and that captures so much. Again, it's about, you, but not in a selfish, self-centered way.
It's about you becoming a shine, a shining light.
Jeffrey Feldberg: So true. And as you're talking about quotes and I was reading your book and actually it came up now when we were talking, it also reminds me one of my favorite quotes from Oscar Wilde, be yourself. Everyone else has already taken, and there's just so much to that in terms of, hey, where's my integrity?
Let me show up as my authentic self. And I know when we're going through the book and I was going through the various chapters, probably an unfair question. We're gonna ask it anyways. Ran. If you had to pick. Favorite chapter. It's almost like asking, well pick your favorite child, but is there a favorite chapter that you have?
What is it and why?
Rand Selig: That is extremely, extremely difficult question. I think the answer. Is gonna be different for different people because there are different points along the path where, for example, there's a chapter on gratitude. [00:31:00] Hugely important. Now I already have that. I am a very grateful person. And people say, well, how can I be grateful?
I just got this bad news. I just lost my job, or I just got the medical diagnosis. And I say, yes, I, and I'm sorry to hear that. And I try to be compassionate. What can I do to help you? But beyond that. Look around. Look around the support you have. Do you have doctors you trust? Do you have the financial wherewithal to get the medical assistance you have?
Can you find a new job? Do you have something to offer? These kinds of things make you more grateful because you can look, you can broaden your perspective around that. So some people would go to gratitude because it's just something missing for them. I'm reading. The book now for the audio book. I'm the narrator when I don't have the cold going on.
And there's a great chapter. I'm just delighted with this chapter. I hope it's great. Spirituality and religion religion of your own, where it works for you in [00:32:00] spirituality, meaning being in awe and being humble. Which for people who've accomplished a lot, having humility is a really important thing.
The way I get it is I go outside and say, I am a nothing. Look at this, millions of years in the making. How does this little bug do its thing? How does this tree sprout another leaf? It's just amazing. Other important things, of course, a huge chapter on emotions and I cover good ones like happiness and.
Try to demystify that. Explain. There are different ways people go down the avenue of, of happiness to love what is love. I say being love is more important than having romantic love. That, that, you know, but then also some of the uh, the tougher emotions being vulnerable being afraid losing somebody that you care deeply about.
These are all part of that chapter as well. So, I would say for your audience, and it's been especially [00:33:00] good for me along the way, is the chapter on leadership and management.
There is a lot of confusion all the time. Unfortunately, our language is a little bit wobbly and we use words interchangeably.
Management and leadership are two very different concepts, and there are very few people who are both good managers and good leaders. And I like to say, well, to distinguish again, just pay attention to what Stephen Covey said about it, he said. Operational management is the efficiency of, climbing the ladder to success, meeting your goals, whereas leadership is making sure the ladder is on the right wall. me that summarizes a lot. I look at that because I'm talking to people, I'm mentoring people around this, and I, you gotta again know where are you? Are you a, a good leader? Do you have vision? That's where I started at the beginning. I've always had a sense of vision and purpose around what we're trying to accomplish [00:34:00] and my management.
Dealing with other people is something I've had to work at and I've had to work hard at. And it's part of this evolving thing.
Jeffrey Feldberg: I wanna ask my next two questions. It's a similar theme. One has to do with the book Thriving that we've been talking about, and another is really looking at your business on the investment banking side. So within the thriving framework, if you had to distill it down into one single question, not just any question, a transformational question that someone should be asking him or herself. What would that question be within the thriving framework?
Rand Selig: The question is have you given yourself permission and unleashed your power to make choices in your life, to get on the path to thriving choices about how you're spending your time? Not just at the workplace, all around you throughout your life, who are you spending your time with? Are these people who get you, understand you, support, you, encourage you, tell you do [00:35:00] more or to do less as the case may be.
How about your habits? What choices are you making about that? What habits do you need to create? Which habits do you absolutely are working for you and you just wanna double down on them? And another choice of course is how you feel. And this is something that people say is that really a choice is absolutely.
Being positive, for example, is a choice you can make all the time. Rather than being afraid, being angry, being cynical. We live in a world, a lot of cynicism.
Jeffrey Feldberg: Some great insights there and you may answer this next question the same way. It's very similar, but now we're looking more big picture in terms of an entrepreneur, and again, in your experience as you look back, so we can look forward. I. What would be perhaps the one question that every entrepreneur should be asking, but they rarely do.
Rand Selig: I'll throw it out this way. Jeffrey, you asked me a great question that I have not been asked before. I've been asked a lot of questions, so, bravo on you. I [00:36:00] think it's the question of why am I here?
as the business person which I think morphs into who do I show up as when I come to work with others, whether it's clients or people, I'm, on my team that I'm, working with my company.
You know Why am I here? And when you dissect that, you have an answer. And again, I say write it down. When you dissect it and you say, wow is this the person gonna be attractive to all these other people. Is this the person who when my kids get older, they're gonna look up and say, wow, dad, you're amazing.
I'm so delighted to have you as my dad. Y Who is that person? We live a life for a lot of people and it's our society norm to try to have a lot of accomplishment. And I don't think you can get by in life without feeling that you're doing good work and you're having a sense of accomplishment.
You can measure that in certain ways. Certainly your investment account your bank [00:37:00] account are part of that. But there are actually, I think if you're honest with yourself only apart if you didn't have to work. What would you do if you are working? Who are you, what are you showing up as?
Jeffrey Feldberg: I love that question actually. I love both questions. And let me ask you this. I've been asking you very specific questions, but let me flip it from me to you, Rand, before we start to go into wrap up mode. Is there a question I haven't asked, and I know there's many questions I haven't had an opportunity to ask just yet, but is there a question I haven't yet asked that's important to you that you'd like to get out there to the Deep Health Nation?
Rand Selig: Well, I think the question is one about how do you keep going? How do you avoid burnout? How do you overcome difficult things? So that's a whole ball of wax right there. Life is filled with endings. Beginnings and in the middle is transitions. And how do you get through that?
Well, this has to do with having a lot of grit, being mentally tough, having resilience. I like to think of [00:38:00] resilience as a rubber ball. If you're looking the rubber ball bouncing and do it in slow motion, you'll see it actually deflating for a little bit and then it.
Shape and bounces back up with that.
The iron ball, the bowling ball, that when it lands on the ground, it does not change shape and it makes a big thud. maybe makes a dent in the floor and then it rolls away. So, being resilient, being mentally tough getting through the transitions that are inevitably part of. Of who we are.
And you've mentioned a number of times North Star, just making sure that you do know you're North Star, maybe a different North Star than the one three years ago. That's okay. That's cool. You, that means you're you're taking charge. You're the one driving the bus. You're the one saying I'm deciding how fast to go and when to stop and when to turn right.
When to turn left. Who to invite on my bus and. The tougher [00:39:00] question, who to invite off my bus.
Jeffrey Feldberg: Yeah, that is such a key one. Let me ask you, because. As rejection. My goodness. That is for most people, not all people, but for most people, rejection's probably the hardest thing. Not only being the reject ee if is such a word, but the person who's doing the rejecting. And I agree with you, Rand that and I, I believe one of my favorite quotes and it just really gets to the heart of what you're talking about.
We are the average of the five people that we spend the most amount of time with. And so Deep Nation, who are you spending the most amount of time with? And if you look at those people, no judgment. If you look at those people, are they holding you back? Are they lifting you up? Are they letting their trials and tribulations become your trial and tribulation?
You may not even realize it, but Rand, if we find ourselves that we want to apply the Thrive framework and we wanna thrive in all areas of our life, yet perhaps there's a work colleague or a friend, even a family member that is holding us back. How do we get them [00:40:00] off the bus?
Rand Selig: Well, I think, of course, it's, it has some kindness associated with it. You don't tell 'em they're a total idiot and disgusting to you. You can do it very kindly. Maybe have a cup of coffee with them and say, Hey, we've had this relationship for all these years and I really appreciate X, Y, and Z about that relationship.
Thank you. And what I'm finding now is that the person I am needs. Some other ingredients, some other qualities. So, I just wanna let you know that I'm just planning to spend a little less time with you. You don't have to say you're fired, you just, I'm gonna spend a little less time with you because I'm now gonna be really spending energy on surrounding myself.
Creating relationships with people who do are willing to support me in these kinds of ways. Now, it could be that the person will say, I wanna be that person. I will support you that way. And in which case you say, well, that'd be terrific, and wait to see if they do or [00:41:00] don't. But chances are that's gonna be a tough ask, that they're not gonna fulfill that.
it's a process then of finding new relationships. I talk about building relationships in my book there's an architecture for it, which I'm, I map out A lot of people have. Friends, I'll leave it in the friend domain who are about their age, plus or minus five years of their own age.
That's completely understandable. But there's a richness, absolute richness to have people, friends who are older, maybe 10, 20 years older, and people who are half your age or, whatever. And the way that happens is through a process of really being interested in them. And asking questions.
more high powered we are, the more we wanna talk. And we don't wanna be doing what you're doing, Jeffrey. Asking questions. Asking questions is the absolute crux of creating new relationships. And when you ask a question, you don't immediately reply, oh, I did that too. No. You just ask another [00:42:00] question about it.
Tell me more. You know what I heard you saying is this and this? Did I get all of that? That seems so interesting. when at the right time they'll come back to you and say, Hey, by the way have you ever done that? Have you ever, and then you can say, oh yeah, thanks for asking.
Yes. Well, I had a an experience too. It's not quite the same as yours, but it was also really a great experience, or it was tough. It doesn't all have to be all this positive stuff. So ask questions and listen.
Jeffrey Feldberg: Absolutely. Dale Carnegie had to win friends and influence people. That classic timeless book all about asking questions and I shared it before on the podcast. I'll share it again just now. I will always remember the story that Carnegie tells. He was at a dinner party back in the day. I. And he was speaking to someone that he just met.
He barely said all the five words. And the person walked away saying, wow, that was the best conversation I've ever had. Just because he was listening, saying a few words, asking a question, pausing, stopping, letting the other person talk because we all love to talk about ourselves. And by the way, Deep Wealth, when you go to the show notes and you click on the link for the book, [00:43:00] thriving.
Chapter nine, relationships with Others is in section two of the book, thriving Together. All of the strategies are there. So Rand, all that said, we're gonna go into wrap up mode now, and this is really my favorite part because it is a tradition here on the default podcast. It's really my privilege of my honor.
I. Every guest I ask the same question and it's a fun question. Lemme set this up for you. 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 is tomorrow morning and you look outside your window. Rand, this is the fun part, the DeLorean car.
There it is, curbside. The door is open. It's waiting for you to hop on in what you do, and you're now gonna go to any point in your life ran as a young child, a teenager, whatever point in time it would be. What would you tell your younger self in terms of life lessons or, Hey Rand, do this life wisdom, don't do that.
What would that sound like? I.
Rand Selig: Well, I, it's not an easy question for me because all of us can be authors of our own [00:44:00] story, which means that we can edit and delete. And I think in my telling of my story, I've done a good job with that. So the life I've led I really and that my history, I like, part of my history has been complicated and hard, but I've.
Turn that into, I've reframe that into the kind of pain and overcoming those pains has led to the person I am today. I've learned a lot. I've become a better, stronger person for all that. So I wouldn't want to even get in my DeLorean car and say, I forget that I'm not gonna have those kinds of problems again.
If there's one thing I picked my parents well and my father towering figure. Very tough guy. But I learned a moral compass and discipline from him and from mom. I learned. Love of nature love of reading, being curious, and both of them are all about service.
And I built me on top of that firm foundation. But one of the things I inherited [00:45:00] from mom was a blood disorder HLAB 27 positive, which leads to it's an autoimmune disease. And in my particular body, that means eye problems. And so, my iris actually gets inflamed and it's sparked by stress. So what kind of career have I had?
A very stressful career. So there were years and years, decades, maybe even where I had more than one of these eye inflammations going on during the course of the year. Would I change that? And either have a much more mild case of it or I wouldn't change my mom. No, I want my mom. There are other things I could have done about that I think differently.
I had great doctors. I had my wife was fantastically supportive to me throughout this period of time. I knew after several of these episodes that this was stress related. Even though my doctor said it has [00:46:00] nothing to do with stress. There's no data, Western doctors databased, no data that supports that.
I said, I know my body and I know this is what it's about. So I needed to take more hot soaks. I needed to. Go for more walks. I needed to breathe. So could I have learned those things earlier? Yes. There's a lot of pain associated with these inflammations as well, and times when I had something due a transaction click, I could not see out of one eye.
It's hard. Would I reduce the burden of that? I would. I. If I would.
Jeffrey Feldberg: Wow. So a lot going on there. And you've taken what life has dealt you and instead of being the victim, it is really the victor. Absolutely love that. What I'm also hearing you say is, Hey, you pitch great parents. Nudge, Nudge, win, wink. Love that, and the humor in that. But also on a serious note, to really learn from those around us that we love and respect.
Take the best of them. Hey, nobody's perfect, but people that we love and respect, what can I learn from? What are their examples? How do I [00:47:00] incorporate that into my life? And that's really Deep Nation, a terrific takeaway for you. And Rand, let me ask you this as we wrap things up here. If someone in the Deep Wealth, they have a question for you, they wanna speak with you, perhaps some coaching, perhaps some insights, perhaps even do a transaction with you, where would be the best place online to reach you?
Rand Selig: Well, my primary focus is around engaging with people about thriving and not so much the business format, but if somebody did have a question on either front, I'd be delighted to connect with them. And the best way to do that is to go to my book website. Www.randseig.com and there's a Connect with Rand page and you can say, Hey, I have a business question X, Y, Z, or I'd love to invite you to be a speaker at our book group or for our company.
Or whatever it is. I'd love to connect. I'm not doing one-on-one coaching but there are a lot of people that I've they've raised a question. I say, here's without [00:48:00] knowing you really well, here's some things I might suggest you think about. And by the way the back of my book are 75 paragraphs about books I've read.
Each book has impacted me enormously. I say go to that, the back of the book. And in your particular case, I think you get a lot of benefit by reading this, these two books, that kind of thing. So yes, absolutely go to my website, love to hear from you.
Jeffrey Feldberg: Dee[ Wealth Nation, it doesn't get any easier. Go to the show notes. It's all in there. It's a point and click for you. Well, Rand, this is official. It's 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: Thanks, Jeffrey.
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?
[00:49:00] 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?
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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.