590 Cindy Jennings

[00:00:00]

When Plans Break

Jeffrey Feldberg: What happens when the person who always has the plan suddenly reaches a chapter where the old plan no longer works?

Cindy Jennings has spent more than 25 years studying change, leadership, human behavior, and what happens when life collides with work. She's the founder of Interwovenly and the creator of LifeWise Programs, where she helps business owners, executives, managers, and high performers navigate the transitions most people rarely prepare for.

Cindy Jennings Intro

Jeffrey Feldberg: Her work began with a realization that should make every founder stop and think. 

We build systems for strategy, performance, growth, and succession. Yet when a death, diagnosis, divorce, business exit, retirement, or other major disruption arrives, even accomplished leaders can suddenly find themselves without a playbook. 

Cindy knows something about reinvention herself. She built a business, chose to close it when that chapter ran its course, [00:01:00] returned to corporate consulting, developed new skills, and ultimately built a second company around helping others navigate change more intentionally.

Today, her work challenges a deeply held assumption among high achievers: that if the financial plan is right, the rest of life will somehow work itself out. Because sometimes the hardest question isn't what's next for the business, instead, the question becomes, who am I when the business no longer needs me?

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 [00:02:00] 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 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 [00:03:00] 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 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.

Host Sets The Stakes

Jeffrey Feldberg: Deep Wealth Nation, welcome to another episode of the Deep Wealth Podcast. Deep Wealth Nation, let me ask you this. When it comes to your business, are you the business and the business is you? What will you do when the chapter closes? And I don't care if you're saying, "Jeffrey, it's decades away, I've got no plans."

Let me tell you something. You will always be likely walking away from the business. Sometimes it's a big exit. We never talk about that. Everyone has it coming to them. But oftentimes, next generation or you get an offer you can't refuse. So what are you gonna do? What does that look like? This is one of my biggest mistakes on my side.

We got an amazing guest who, my goodness, I can [00:04:00] only imagine what I could have prevented the pain on my side had I known about her beforehand. But that said, Sendy, welcome to Deep Wealth Podcast. An absolute pleasure to have you with us. There's always a story behind the story. My goodness, you have quite the story.

So what's your story? What got you from where you were to where you are today?

Cindy Origin Story

Cindy Jennings: By accident, Jeffrey. My own wealth advisor sat me down, I think it was in 2019, and was like, "When do you want to retire?" And I was honestly a little insulted 'cause I'm like, "Hey, do I look like I'm ready to retire?" And I was just getting ready to start a new business and... But what jolted me actually and started this whole journey for me is I didn't know.

Like, Not only did I not know when I wanted to retire, if I wanted to retire, quite frankly, 'cause I think of myself as I've gone in and out of entrepreneurship, but I think of myself as an entrepreneur. I didn't know what was next. And so I really just, I thought, " At the time I was working for a management consulting firm, getting ready to go out on my own, and I'm like, "I do strategic planning and change, management for large [00:05:00] organizations, so how do I not have a strategic plan for myself?"

I was Surprised, to put it lightly. And so I just, as a problem solver, set out to figure that out for myself, and so I did, and then just looked into, like what creates a meaningful life outside of work? What creates, purpose and meaning? And laid that out for myself, and then I started talking to my friends, and they were saying, "We need that too."

And what I found as I was doing these workshops for my friends in living rooms, and then they were like, " our friends want it," and so it just started to expand, if you will, and people were finding real value in this. And a few things came up. One is how hard it is to know what you want in life, how weird it is to be like, "What do you want?"

And I think some people know, and you can say, oh, travel or money, or like there's the surface-y things that come up. But in like what do you really want? What's really gonna fill your cup? That's a hard question to answer, and so I figured out a methodology to surface those answers for people.

[00:06:00] And the other thing is, was surprised at how many people in those little workshops did not have a financial plan. Either if they were entrepreneurs They had a business plan, but they didn't have a personal financial plan or a personal plan. And so I don't work in the financial planning space, but I work with those people, and I highly encourage a three-pronged approach, having your business plan, your business financial plan, and your personal, financial and personal plan.

So it just sort of evolved. It happened by accident from one question and just me wanting to seek the answers, and it has evolved into now working with business owners who are looking to sell their businesses. Primarily that's the big transition, right? So what's next? Sometimes it's life-changing money.

Sometimes it's enough to start the next business. If you're just gonna start the next business, is it the same thing you did just in a different place or with new people, or is it something completely different? So we answer those questions together. And that's how it's evolved.

I also work with corporate executives, and recently starting to work with a [00:07:00] younger generation in professional athletes as they make that transition from professional athlete to what's next for them. So all high performers. High performers making big transitions who have a lot of their identity tied up in owning a business, being successful, meeting goals, and when that goes away, what happens?

Post Exit Identity Crash

Jeffrey Feldberg: What I love about that, whether in Deep Wealth Nation you are a founder, perhaps you're working with the founder, you're part of the C-suite and you've been brought on board, or even an athlete in your case, Cindy, of all those different groups that you're working with, to me, and speaking from personal experience we're talking a little bit offline with this, this was my dark night of the soul.

I had no identity outside the business, and Deep Wealth Nation, do you? If we took away the business, who are you? What would you be doing? Would you be like Jeffrey on day one of post-exit of, "Hey, I'm bored. Let's go out and play." But everyone, "Jeffrey, I'm sorry, I can't. I've [00:08:00] got my company I gotta run," or, "I'm in my career, I can't do that," or, "I have other responsibilities."

And no one's gonna feel sorry for some guy who just closed a big deal sitting home in his pajamas bored out of his mind. And so with that in mind, when you're working with a new client and when you look at who you've worked with, is it good old Pareto's Law? Yeah, Jeffrey, 80% of the things that are literally keeping people up at night are coming from the same 20%, or maybe it's 90/10 or 95/5 of these areas here.

Are, Are there common patterns that you're seeing? A- and if there are, what are they?

Common Post Sale Patterns

Cindy Jennings: 100%. you are illustrating at least a couple of them. So there is the euphoria of selling your business, right? You're like, "Sweet, I'm out of here." You know, let's go, We talked about going to the beach and having a piña colada. But what happens is the infrastructure, the foundation, having a business tells you when to wake up, where to go, who to talk to, what problems to [00:09:00] solve, and suddenly you've got a whole bunch of money and freedom, but the freedom comes without any kind of structure.

And so you're sort of in a free fall, a lot of people. I won't go into statistics, but there are statistics about people falling into really bad places. And in my early starting of this, I was working mostly with people post-sale who were in depressed, pretty scary places, some of them where it's like this is beyond my skill set.

You need to really go get some real help. And then we can work on building that foundation back up. Now I try to work with people before that so we don't have to go into the chasm, right? Go into the abyss, if you will. So I think two things. So one, there's just the assumption that life is gonna be great.

Two is what you said your friends are not in the same place as you. So all the people who are also, I don't know if you have other entrepreneur friends or just other people who are working, and you're at a relatively young age, and they don't have the freedom to go do the things you can do. So also very much a pattern.

And then three, I think the other pattern I see a lot is the [00:10:00] people who don't pre-plan what they're gonna be or who they're going to be post-exit, what's gonna fill them up, what's gonna give them purpose, is that they have this euphoric... in months one to three, it's euphoric. By three to six, maybe you're still in little euphoria, but there's a little something underneath where you're like maybe this isn't all it's gonna be cracked up to be."

And by, month six to 12, you're either making really bad decisions or you're buying a business again that you don't really want to buy or, any number of, things that come up that weren't really intentional and don't put you at, in a good place to be set for success going forward.

Jeffrey Feldberg: Yeah. As you're talking about that, I'm going down memory lane and really for myself, the first, and I don't think I'm unique with this, the first six months for me, it was a lot of sleeping in. I never had that opportunity when I was building Embanet. It was going 24/7, on the go, traveling six months a year, all, all those things.

But by around month six or seven, when lunch became the highlight of the day, I said, "Okay, I've got some [00:11:00] issues here." And all the time in the world and zeros in the bank with no North Star, no purpose, that is when trouble began, at least for me to set in. 

Why Plan Before Exit

Jeffrey Feldberg: But before that, and here's where I want to hone in on, I- I'm speaking to the founder in Deep Wealth Nation who's thinking, "Yeah, Sendy, good for you.

It's all fine and good. 10 years, 20 years, maybe 30 years away, come back and talk to me." I was like that. I was young, naive, stubborn, Type A personality. I couldn't even imagine life after the exit, and I would tell myself, "Jeffrey, just get across the finish line. Once you've done that, you'll figure it all out."

Whereas the narrative, which was completely wrong with what I shared, "Hey, Jeffrey, yeah, get across the finish line. Carve out some time for the day after the sale." And if it wasn't a full sale, it could've been a partial, [00:12:00] whatever it was going to be, that I could test things out that I wasn't doing it in real time with all the time in the world.

So speaking to that founder saying, "Yeah, Sendy, whatever. Two, three decades, come back and talk to me," what would you say to that founder that would have him or her think twice about that?

Cindy Jennings: A couple of things. I think we hear a lot start with the end in mind, and that would be from a valuation standpoint, from a business standpoint, and I think it's equally as true on the personal standpoint. I guess I would ask you, what is it all for? So what is this building the business for?

So some of it is sense of accomplishment, ego, all those kinds of things. That's fine, and what else? So I think if you add the question and. So I wanna build the biggest company. I wanna have the biggest exit. I wanna have the biggest multiple of an exit. Great, and what? For what? So to what end? Is it worth the cost of having no friends, no life for the next five to 10 [00:13:00] years?

Or do you wanna have and bring friends along in those five to 10 years? Can you do both? Are you... Do you wanna be healthy and vital and vibrant when you sell that business? So what's the and? So I wanna have $10 million and the best health because I'm gonna go do these things, or I wanna have $50 million, or whatever the number is for you, and so that I can go do these things.

my hope for business owners along the way... look, I can sink into business and get focused and ignore my social connections, my health with the best of them, right? But it's, to me, I guess as I get older, it's you find that it's not worth it. It's I want both. I want success and I want health.

I want success and I want meaning outside of just what I do. I find tremendous value in meaning in what I do, but I don't want it to define me. So I guess I would add a, an and or a so that to that question. And I think if you know what you want, [00:14:00] if it is 10 or 30 years, if I'm 30 years old and retirement feels so far away or maybe I'm never gonna retire, which I totally relate to, but it's like what does that...

Like, what's it for? What is this for? And when you have that North Star, to use your term, then the decisions you make along the way I think change. And so a lot of the work that I do is, yes, we're figuring out what's meaningful and purposeful to you, but a lot of it is about how you make decisions. So if you have a plan, if you have an idea of what you want, those are gonna change obviously.

Opportunities are gonna come up. Things are gonna change, of course. But if you have an idea of you know that in 10 years, in 20, 30 years, I want my life to look like generally like this, then I make different decisions about my business now.

Jeffrey Feldberg: It's interesting. 

Money Mindset And More

Jeffrey Feldberg: Let me put two things out there. Would love your thoughts on this. And a shout-out to AJ Wasserstein, a fellow post-exit entrepreneur, and he's uh, an alumnus of The Deep Wealth Podcast, also a personal friend. He studies [00:15:00] this now. That's all he does is study it. And a short while back, he had done his latest survey.

Cindy, it blew my mind because he went to post-exit entrepreneurs. Some of them had a few million put away, some of them were worth billions, and everything else in between, yet the answer was the same. "Do you have enough money? And if the answer's no, how much more would you want?" And regardless of how many zeros were there, from the millions to the billions, it was two X to three X more.

Think about that. Of, yeah, I've got 10 million socked away or a million or a billion. I wouldn't mind having two or three times. I don't feel it's enough.

So wow. Regardless of the money, to me it's just all part of the human condition in terms of what's there and it's never enough and where do I wanna be and, yeah, I could have some more money and not having that, that North Star.

the second data point is guests who have been going through The Deep Wealth [00:16:00] Podcast, some of them, wow, what they've accomplished is incredible, and without any judgment, no aspersions, I wouldn't change a day with them because with what I hear, it's as though they're locked in their own golden handcuffs.

I'll just be polite. Their own golden handcuffs. It's the next conquest. They've got to the top of one mountain. Great. Let me go to the top of the next one. Versus when I've spoken with other people who maybe they pale in comparison to the number of zeros they have in the bank, but wow, are they rich. They are rich in the terms of joy, fulfillment, happiness, and they've kept things really simple.

Would love your thoughts on those two opposite ends of the spectrum there of what's going on.

Cindy Jennings: Yeah. I think again, I'm not a financial psychologist, but I play one on TV. No, not really, but I think just from experience we are, as a species, as humans, really weird about [00:17:00] money, right? We come from different backgrounds. This isn't always true, but I find that a lot of entrepreneurs who are super successful usually are overcoming some kind of adversity early on.

Doesn't always mean that. And so when you look into that psychology, it's like their fear of being homeless and poor is high. It's really high. It's not rational because they have got multiple zeros in their bank account, and I think, when you said earlier nobody is gonna feel sorry for the guy that's got a bunch of zeros in his bank account and is unhappy, but the reality is it's true.

And so I think, there's some shame around that where it's like, oh, I guess I just, need to keep doing that. It may not be recognized, we just have some internal things about money in, within ourselves, and if you don't know what that is for you, what your mon- your motivator or your fears around money are, I think you continue to run on that hamster wheel.

I can think of a person who has about 50, [00:18:00] has plenty of money in the bank, and not believe it, does not believe it. Financial advisor tells him, "You're fine. You could quit today, walk away, not even sell your business. You're fine," in his heart, does not believe it. And so, you know, that is a real thing, and I think the other piece of it is we are so used to, whether you wanna retire or not, we're so used to like, save for retirement, save for retirement save, save, save.

And so then when you can finally sell your business and relax, we can't because we're so used to investing, putting money into business, putting money in our savings account or wherever we're putting it into new investments. It's so hard to rely on the funds that you have in your stock portfolio or your, wherever it is for you and just rely on that and believe that it's going to last you the rest of your life

Cindy Framework Overview

Jeffrey Feldberg: And so not to get all depressing for the evaluation of what's there, walk us through your system, also your insights of, "Okay, Sendy, yeah, I'm still not so [00:19:00] sure, but I'm hearing you of what you're saying. I'm open to hear a little bit more. So what does it look like? I start working with you. Yeah, I heard you on the Deep Wealth Podcast, and I don't see it really ever happening, but we'll give it the benefit of the doubt."

Where are we starting? What are we doing? How long does it take? What does it look like?

Cindy Jennings: Yeah. I think, and to your point, I mean, this system is not gonna be for everyone. This is for the lifelong learner and the person who wants to have a quality of life alongside business and wealth success. So I do use a minimum of a 10-year horizon for my work, and we're looking at eight key areas of life as we do that.

There's some work, pre-work that happens beforehand. We're looking at values. So your values are one thing as you... And we all have values. Whether we can name them or not, we have them, and so we just put names to them, your personal values, not your company motto, not your company core values, your personal values.

And then how those might change over time, which ones are gonna stay, which ones are gonna change. And then we also look at [00:20:00] how you like to be in action, right? That can vary for different people. So it could be giving back as an action for some people, or just making more, as an action for other people.

So how do you as an entrepreneur, as a business person, like to be in action? And then we'll take those into this, these eight areas of life, and we use a, at least a 10-year timeframe. 

Time Spaciousness Vision

Cindy Jennings: If they can think out 20, it's actually preferred, and there's some neuroscience behind it that I won't bore you with, but essentially it creates time spaciousness.

So I think if you're an entrepreneur right now not buying into this, but you want to succeed going forward and you want to have this great life, not just have a lot of money, then the spaciousness allows you to It does something in your brain and that, again, I'm not a scientist to do that, but if you think 20 years out, if you put the age to that, in 20 years I'll be...

Let's say I'm 30, I'll be 50. So if you put the age to it, in 20 years I'll be 50, I want my life to look like this. It allows your brain to [00:21:00] not solve today's problems, and to be like, "That's what you're doubting me right now?" Like, "Oh, okay yeah, yeah, that all sounds nice and great." "I've got real business problems to solve right now.

I can't think about myself. I'll think about that when I get there." This forces you to think about 10, 20, even 30 years out if you have the capacity to do that, and it allows you to get out of today's problems, and then think about what you truly want. And so if you want a, again, let's go back to the 10X multiple sale, or I want a, a billion-dollar sale, whatever it is, that's fine.

Excuse me. So from a business standpoint, it can help you see great, how do I get there? How do I become... If I'm 10 million today, how do I get to a billion in 10 to 30 years?" So that helps you that way. And then who do you need to become to be that billion-dollar exit person, and what does your life look like at that point in time?

So if you have a billion-dollar sale, what are you gonna do with your time? Are you gonna buy a yacht? Are you [00:22:00] gonna buy a... Houses for all your friends? Like, What are you gonna do? Are you just gonna pile it away? Who are you when you're 50 years old and a business owner with a sale? Again, I'm not gonna convince anyone who's really stuck in their brain that this, I don't get it.

But what I can say is this time spaciousness is a magical tool when you can really allow it to get out of your day-to-day grind as a business owner. It even pulls you above the five-year strategic plan, right? To really think about your life in a deep way- what it's gonna look like, not just from a business standpoint, but from, will you have kids by then?

If you do, how are you gonna pass on generational wealth? If you're a grandparent, how are you gonna pass down your family cultural legacy? Are you gonna teach them about money? Are you gonna teach them about relationships? Are you gonna teach them about health and vitality? What are you gonna...

Like, how do you want to your life to be used and to be remembered going forward? And while if I'm sitting here in front of my computer and spreadsheets, [00:23:00] that feels so long and so foreign from me, but if you can allow yourself the space to sit back, take a moment, even if you do it on your own, that's great.

If you do it with me, we'll work out together and push you. And The people who do it, their goals, they don't even el- they elevate from the business standpoint, but they elevate from the personal standpoint, and I just see I see shoulders raise when we go in, and I see them drop, releasing some of the anxiety.

I mean, being an entrepreneur, you're filled with anxiety all the time. At least I am. what am I doing next? What's the next thing?" "We gotta solve this problem. Let's go." And so if you're like, "Oh, okay, I actually have a direction and the freedom and the way to make decisions about this going forward," there's something that relieves some of that pressure and tension.

So I guess I would say if you're a stressed out entrepreneur right now, that this is a way to relieve some of that pressure and stress in a way that is it's long-term relief. It's vision building. I think it builds excitement for the [00:24:00] future versus fear, and gets you, pulls you out of the day-to-day into, the bigger purpose that you might have.

Fulfillment After Exit

Jeffrey Feldberg: And as you're talking about that, Sendy, in preparing for today, the one word that kept on coming up in my research, and I was so happy to see it, fulfillment. Offline we were speaking about another F word, fun, but here's another one, fulfillment. And because to me, happy means different things to different people, and oftentimes we confuse happiness with something it really isn't.

No judgments there. Fulfillment, though, gets, at least for me, to the heart of the matter. Of it is exactly where it should be. Yes, this has me energized. I love where I am or what I'm doing with that. And so with that in mind, again, going down memory lane, a really good friend pulled me aside. This is post-exit.

I had these grandiose plans, and he said, "Jeffrey, I tell this to you as your friend with all the [00:25:00] respect and love in the world, stop your plans. Don't move forward. Travel the world. Take two years. I'd love it if you took three years and just did nothing, and then re-look at your plans." And of course, I knew better.

Yeah, whatever.

Didn't listen. But he was right, because those plans did stop after considerable expense, time, and effort down the road. And where I'm going with this is with you being the expert as a strategist and as a change advisor, post-exit, whether I wanted to recognize it or not, the Jeffrey pre-exit was a different Jeffrey post-exit.

And it's not that one was better or worse, those are just labels, but there was a definite difference. And what's going on with that of post-exits? I can imagine someone in Deep Wealth Nation, "Yeah, give me those problems. I'll happily take [00:26:00] them, Jeffrey. Time and money in the bank. Yeah, no problems.

Bring it on." Easier said than done, because it's not the easiest path either. And if you've been there, you know exactly, or you are there right now, you know exactly what I'm talking about, Deep Wealth Nation. But what's going on behind the scenes with that of people change. Our outlook changes regardless of where we are and what age we have and where on the journey we are.

Post-exit, things change, and maybe you're not selling a company. Maybe you're leaving the corporate world and you're now going into retirement, and you haven't thought about that, and you're just gonna take it head-on like a founder who sold the company. So what's going on there, Sendy? What would you want Deep Wealth Nation to know?

Jeffrey Plans And Lessons

Cindy Jennings: Before I answer that, I have an answer, but I wanna know what were your plans? in broad strokes, what were your plans that went

Jeffrey Feldberg: in broad strokes, yeah, I was buying companies to run. I was buying personal real estate like it was going out of style, and the checks were being written, and the time was going. By the way, [00:27:00] spoiler alert, all of it failed. All the businesses went down the tubes, even though when I started Embanet, on paper, it should have failed.

No money, no team, no experience, yet it was a success. Post-exit, the newer companies should have worked. I had the money, I had the experience, I had the team. I lacked the passion. And on the personal side with the real estate, I just, three years later, why do I want those headaches? Why do I want that cash burn?

What am I doing? Does it really need to be that big? This is crazy. This is insanity. I had changed as a, a person, and the other thing I'll throw your way out there for Deep Wealth Nation, I don't believe I- I'm alone in this. Imagine for just a moment, all of us have a gazillion dollars. Some long-lost relative we never knew passed away, someone shows up at the door, "Oh, here's a check.

You're the only heir of this fortune." And after you buy your [00:28:00] toys, you travel, all those other things, what's really meaningfully gonna make a difference? I mean A real difference, going back to fulfillment in your life. And in my case, it was really not much, really nothing at all materially. The gap, the black hole, so to speak, the unfulfillment I was feeling could not be filled with shiny objects or buying things.

Happiness, fulfillment, it's an inside job. Yes, money greases the wheels. It makes life a whole lot easier. Long-term wise, it doesn't bring happiness. So maybe TMI for you to your

Cindy Jennings: No, it's good

Jeffrey Feldberg: question. But yeah that's what was going on.

Health Meaning Community

Cindy Jennings: The reason I wanted to ask, and I, hope it's okay to say, but I think that those plans were what do you do with your money, not do- what do you do with your life, right? So we know from research that you need three things if you're not working. You need your health, you need meaning, and you need community.

So when we look at the eight areas of life, so that runs the gamut of physical health and [00:29:00] vitality partner and romance if you have one in your life fun and adventure, certainly your financial spirituality and meaning, home. Let me see if I can remember all of them. That's about it. Home your family life, and then your personal legacy and growth.

So those all wrap into sort of these three, health, meaning, and community, in different ways, and we're breaking them down into a bit more granular. A couple of things. 

Values Into Scaffolding

Cindy Jennings: So when I say plan, If I back up a second, again, if we go back to those values and how you like to a- we're tapping into, first of all, who are you?

So when we start working, we do a, a deep download of discovery, and I apologize, it's a prior guest of yours, she talked a lot about, she loved I can't remember her quote, but she didn't like building businesses, she liked creating new markets. She liked doing pioneering nobody's done this before kinds of things.

And so in discovery, we hopefully uncover things like that, right? So even if you're working in your business, it's like, okay, what's your thing? What do you really love to do? And so when we create a plan [00:30:00] that's post-sale, or even before you sell ideally that you're starting to experiment on, that this plan is more like, it's more like a scaffolding, if you will, than a plan.

So plans can be, feel hard and fast. I always feel like plan- plans can change. But we're building them off the multi-dimensions of who you are versus just you as a business owner or just the money that you're going to gain from that. 

Guitar To Giving Back

Cindy Jennings: I can tell us... There's a, business owner who sold, and he loved playing guitar.

He'd set it down for a long time. And when he sold his business, he's like, "Fine, I'm gonna, play my guitar." And he did that for the three to six months, right? Loved it. Played with friends. He just, played, got himself back into the rhythm, whatnot. And he didn't want to join a band. He just wanted to play, but he then also was missing the engagement of people from his business.

And so what he did is he found a children's hospital, and he also wanted to travel and have freedom, which many people do selling a business, right? Or even in the business. And so he developed a relationship with a children's hospital. He goes in [00:31:00] and he plays, a couple times a week, but then he can take time off when he's traveling and doing whatever.

And he just gets to commun- you know, he plays like, he now has relationships with the nurses, and the doctors, and the kids, and the physical therapists. And this is a whole new world to him. He was not in healthcare prior to this. And he gets fulfillment from both doing something he loves- He's giving back, he's expanding his world into this new healthcare thing, so his mind is expanding.

He loves to learn. So he's tapping into several things that came up for him when he talked about what fills his cup, right? what's his meaning. And now, as a result of that, one of his investments is he's looking at buying one of the School of Rock franchises, He's not gonna be the day-to-day guy. he just wants to be involved in it 'cause he loves music and kids and wants to, just be involved in that kind of thing. Versus, if I may, contra- like, maybe you love real estate. Sounds like maybe you didn't. And so maybe there are other investments that would actually provide meaning for you that you could be involved in a small or a large way, depending on what you want what [00:32:00] uncovers for you in this process that, and then it's like this, the thread starts to pull, right? Oh, I like to play guitar. Oh, I actually like to be around people. Oh, you know what? I'm interested in healthcare. Oh, maybe I'll, go back to do School of Rock. So school- buying a School of Rock franchise was never in his original plan, but it's there now.

I mean, This is a small example, of something that can happen, but it's one thing begets the other, and I just really encourage, if we go back to why would I do this now, even if I'm not selling in a long time, it's like experiment now with what fills you up. I highly encourage it.

And I, usually I'm working with people one to two years away from sale, and so I'm like, "All right, let's just, you know..." I had one business owner who's like, "I love to paint, and I love to play guitar," and I... Like, he had 12 different things he wants to do. He had no issue with what am I gonna do next?

It was more of like, let's filter down to which ones are actually gonna be real for you. And we, worked through that as well, and he started before he left, while he could. So it's just, I think the piece [00:33:00] of it is when you leave, a business sale is largely financial, right?

And people plan for that. You've got nine steps for it and what I love about your work is business owners don't plan for it generally, so I love that you have a plan to do that. But I think the piece that gets missed is the personal plan. This is also a personal transition. and by personal, I don't just mean you.

I mean it's like, you are now doing this podcast, and you are giving back to people, and you found your way here, and I would assume, but you can confirm, that this is filling your cup in a way that buying real estate did not. So it, yeah.

Jeffrey Feldberg: Yeah. 

Test Drives Before Exit

Jeffrey Feldberg: And what's interesting, and Deep Wealth Nation, it's very subtle, and let me bring you in on this Deep Wealth Nation, because the groups that, that you're working with, Sendy, so yeah, founders and people that are leading organizations, the C-suite, even athletes, what's going on there is when I'm no longer the athlete that [00:34:00] I'm competing, those days are gone, or I'm no longer leading the company that I was hired to lead, or I no longer own the company, or I'm just not doing the day-to-day, when you're still doing those activities, by taking the time out now, even a few hours a week, you can learn very quickly...

to your example, Sendy, I love playing the guitar, but that's all it is. After the first hour or two, I can't stand it. Or, yeah, I love playing the guitar. I can see myself not performing and touring and all those other things, or maybe it is, but I can see myself somehow involved with that. We give ourselves the time, and this is the key, in a no-pressure way, nothing ventured, nothing gained,

Cindy Jennings: Угу

Jeffrey Feldberg: I can figure out I can see myself spending more time with this.

I really feel energized after I'm done with this or, wow, I feel energized, but all the energy was drained out of me

Cindy Jennings: Yeah, that went [00:35:00] the wrong way.

Jeffrey Feldberg: that, that's right, that we give ourselves the time. I never had that, not because of anything other than me, to point it back to me. I didn't do that. And so in real time, when the stakes were high and I was already feeling guilty I'm not doing enough, I could be doing this, or I...

The shoulds, I should be out there. When we can do it when we're so loving what we're doing, even though we don't have the time, when it comes a time, if I've done it right, when I've done it right, I'm working with you, obviously I'm gonna do it right, that chapter has closed. It's a continuation. Yeah, it's not gonna be perfect.

It's a larger continuation because I know what I don't want to do, and I know what I do want to do, and I've removed a lot of the speed bumps and hiccups along the way. Thoughts about that?

Freedom Needs Structure

Cindy Jennings: Yeah, I think you hit on a couple of things. One, I think a great observation is we can tend to romanticize things that we think we wanna do, right? And I think travel is one of those things. Travel is lovely. I love to travel. [00:36:00] But is it gonna solve all of your problems? No, it's not. Taking care of your grandkids if you're at that age, like lovely, but it's not gonna be all of your time.

I think there's that piece of it. something you said way earlier, that this is very much an inside game. If you're traveling and figuring out sort of who you are and what you want and doing all the things, awesome, more power to you. But I think when you just go from... I think people think the transition's gonna be easy 'cause you've got all this money behind you, so life is good, right?

And the reality is, it's incredibly difficult. Incredibly difficult. I mean, You are not the only one to say, first six months to a year after selling a business was the dark night of my soul and which leads me to, high performers, business owners, athletes, chief executives, C-suite, we all have a scorecard whether we know it or not, right?

And if you're at work, you have a scorecard: revenue, KPIs, all the kinds of things. And that creates structure,

We think that the money's gonna give us freedom, and it does. It gives us freedom to create [00:37:00] our own new structure, right? I think as humans-- like, it may be a more spacious structure, a wide-open one, but I think the value of what I see, when people leave their business, they have a lot of anxiety, maybe a lot of excitement, too, they-- hopefully, they do.

And having-- redefining what your structure is, what gives you meaning, purpose in your life post, now you've got all the money in the world or at least enough to have discretionary, decisions about your life, still having some structure around that is key. Otherwise, you're floating. I think people think freedom is bliss, and really, it's-- when you have all of the options.

Think about going to a grocery store, and you've got 35 different barbecue sauces to choose from, and you don't-- you've never bought a barbecue sauce before. Which one are you gonna choose? Why and how? Is it based on the label? Is it, what taste profile do you prefer?

Maybe you're grabbing a bunch of them off the shelf and checking it out, but you don't really have a way to know until you try. And I think some, putting some structure under what is gonna bring value to your [00:38:00] life is really important. I don't know if I answered your question.

Did I answer your question?

Jeffrey Feldberg: absolutely. And Deep Wealth Nation, really you're hearing two friends, it's a fireside chat, we're talking with each other. Your takeaway, and it's a big one, as I jokingly say in the podcast, imagine it's time to submit your taxes. Are you gonna learn the tax code or are you gonna bring on a chartered accountant who's gonna do it for you?

This is bigger than taxes. This is your life, Deep Wealth Nation. And so do you wanna be the guinea pig with your life? Or would you rather work with someone like Sendy who's been there, done that for countless founders, executives, now athletes of, "Yeah, Jeffrey, you're gonna have some speed bumps. It's actually good for you to go through those speed bumps, but I'm gonna minimize them, and the ones that you do go through, they'll be fewer and they'll be far rougher than they would've been."

Wow, what a difference that would've made for me, Sendy. I can only hope back in the day that pre-exit Jeffrey would've been wise enough and smart enough and without the [00:39:00] ego to listen to your sage advice that would go along with it. What a difference though that could have made, and why have to be the guinea pig of my own life when someone like yourself could really make a difference and, "Hey, let's try this instead of that.

What do you think, Jeffrey?" "Oh, yeah, that is so much better." How am I doing with that in terms of the system and the strategies of what you're doing when you're working with someone?

Process And Decision Compass

Cindy Jennings: I think what appeals to people is there is a process and a structure to what I do, and it's also flexible enough to be bespoke, to be custom to exactly who you are, right? So we tease out using the system that I've now honed over several years to, nobody's plan is gonna look the same.

Nobody's experimental plan is gonna be the same. And we do a lot of the heavy work. So it's about a six-month program to start with, and so the heavy lifting is really in the first six weeks where we're doing this deep dive into kind of who you are, da. And then the rest of the time is [00:40:00] experimenting and me being there right beside you 'cause you know what?

It's hard to do that even if you have all the time, but if you're working at the same time, it's so easy to just be like, "Oh, that's hard. I don't know how to do that. You have to get the beginner's mindset which, frankly, if you got the ego, it's hard to do, right? And so I'm there to help you, to be like, "Hey, how did that go?

Okay, that wasn't great. It could look like this." Or, "Do you know I saw this person do it this way and this person do it that way. What if we combine that with yours, and we make a third way? What would that look like?" It's also some of the decision-making, too. So I talked about that a little bit earlier.

But, you know, I had one business owner, and I said, "What are you gonna do?" And he just wanted to, he wanted to be done. He was done, right? And I said great. What are you gonna say when the request to consult come in?" He goes, "Oh, nobody's done that. Nobody's done that." And the very next call we had, which was like a couple weeks later, he goes, "I had lunch, and I got the consulting question." But we'd already talked about it, so he had his answer, and we had gone through sort of that decisioning. I have a decision compass which is a tool we use in the [00:41:00] process. And he had already...

That's that North Star, if you will. What is it that I want, and what's the question I'm gonna ask myself to keep me there? And so he already had that, and so he had his answer ready to go for this person that was like, "Hey, come consult with us." And he had his answer ready to go. So- I think the structure appeals to those of us that are...

You know, when you're in business, there's structure. Even if you're a free-wheeling entrepreneur, there are still certain things that you need to accomplish to do. It very much aligns with strategic planning, right? And I think by nature, entrepreneurs are opportunistic. So I think when I say there is a plan or a scaffolding that you then gets tested and reconfigured, that generally appeals to the business owner who is okay.

You're not gonna just try to tamp me down into some plan that I can't get out of," right? And give you the freedom. And I guess I would say, you know, the, freedom without direction is drift, and freedom with a structure that you've designed is purposeful and intentional, and I think allows your next...

we're living so much [00:42:00] longer, right? So it allows your next 10, 20, 30, 40, 50 years to be really incredible versus taking a year or two dive into the dark abyss, you know, and having to claw your way out of it.

Sell Or Keep Options

Jeffrey Feldberg: And what's interesting about that, as Cindy, you're talking about that the mind works in mysterious ways, I'm actually thinking of a founder who went through our nine-day Deep Wealth Mastery, Bill. And at the end of it, Bill came to me, said, "Jeffrey, what I love most about the program is if my business is now at a level that I can sell, it also means I don't have to.

I don't have that pressure." And so where I'm going with that, Cindy, working with you, I've put together this life plan, this life map. I can now make that decision of I'm not gonna sell the business out of fear because I don't have to sell the business. I can keep on doing what I'm doing. I can have it all.

I have a life I enjoy outside the business. I can continue in [00:43:00] the business, and if it makes right, if it looks good, the numbers add up, and it fits my terms, not the other way around, then yeah maybe. But if not, I still have a great business. I have a great life. I don't have to go anywhere. What a difference with that versus, "Oh my goodness, I can't sell the business.

What am I gonna do?" And it's the deal of a lifetime that you're passing up because of fear of I can't imagine life outside the business with all those different things that are going on with that. Thoughts about that?

Cindy Jennings: Yeah, what's coming to mind for me is I actually have a client right now who is intending to sell in November, so we're-- yeah, in, so in about a month, six weeks. But they are very much in the place where like, if it doesn't sell, So I find a lot of people like, if the business is running itself do I sell it or do I just keep it and then what?

I don't find that the process is l- significantly different. Again, we go back to that who are you? What do you want? What are your values? What is it, the life that you wanna create? And then [00:44:00] this couple, they're like, we really would like to sell, but if it doesn't, then we know what we want it to look like after refusing to sell."

We know it w- And so by having their plan figured out, So they have some wiggle room in it, if you will, right? To, okay, if we sell it, great, we're gonna do these kinds of things. We wanna explore with this, and we want our life to look like this. And if we don't sell it, if we decide, you know what, if it just falls through for whatever reason or something goes sideways, we're okay with that.

We don't hate the business. We kinda like it. But we would structure it like this and, being less involved and go live our lives, go live 80% of what we've just outlined anyway. And so, I think it can live side by side, and that's the beauty of it. Again, I just think the exit is a structure for, and a forcing function, if you will, to think about what you want in your life.

But this process... I mean, again, if you just go back to the very beginning where it's how in the world is it so hard for us to define what we want, in our [00:45:00] lives? So you could be in a corporate job, and still do this process and still have it me- be meaningful going forward.

Jeffrey Feldberg: Absolutely. And for me anyways, it's as much about what I want as what I don't want.

Both are decisions, both bring clarity. When I know what I don't want, okay, not going there, and actually step three future buyer, we talk all about that. Hey, what don't I want, and what do I absolutely want to see? If it's either there or not there, it determines am I walking away from this?

Are we continuing to talk? So I'm right there with you in terms of what you're sharing, really big points that are there. And speaking of that, before we go into wrap up mode, we're not quite there yet, but let me ask you this. Is there, Cindy, a question that you and I haven't covered? A big question or maybe even a topic or a theme that we haven't covered that you want to get out to Deep Wealth Nation

Spouse And Partner Transition

Cindy Jennings: Yes, for sure. I was talk about the importance. If you're... The [00:46:00] Deep Wealth Nation business owners are married or partnered, that this is absolutely a decision that impacts them as well, whether they're involved in the business, working on their own, or staying at home, however that works out for them.

It is a two-person transition, and my work includes the spouse or partner when I work with them because of that. And so I just wanna point that out that, they don't have... The spouse does not have to be involved, but I highly encourage it. The amount of anxiety in a spouse or partner can be equally as high as a business owner, if not higher sometimes.

And also, if you... Let's just go with being married, just for ease of sake, but you could be partnered. you know, You've been married for 10, 20, 30 years, and you have a certain way of operating, and when one person is going to sell a business and suddenly have a lot of free time that wasn't there before, that is a major adjustment, even when they both want it, and navigating that causes a lot of anxiety.

I can give you all kinds of stories. I had one client who he was actually a corporate executive, but [00:47:00] he was retiring in May, and we started working the May before, so a year ahead of this, transition, this exit. And his wife was like, "Oh my gosh, he already gives me a ton of to do things.

When he retires, all I'm gonna be doing is running around doing his list," and she happened to be a stay-at-home. She had a career, and then she had retired earlier, and she's "I've got my life figured out and I really want him to retire, but I do not want all these, I do not want all these honey-dos."

And so we worked through that, and we worked through some communication tools for them. You're going into this transition. You have a new way of living also at home and a new way of communicating, so just giving them tools to navigate some of those changes. And in November of last year , I get a panicked call from her saying, "Oh my God, he just moved it up.

He's retiring in December, not May," 'cause there was a family member taking over the company, and he was ready early. And she's like, "What am I gonna do?" Even though we had gone through, " Here's how you can manage some of that. Here's how you both can work through that. You want to do these things together.

[00:48:00] You're in total alignment there." We'd worked through all of that, but when the time came for the date to move up, she was not ready, and she was freaked out. So just say that to say the work that we had done was really helpful 'cause I could be like, "Remember the tools we talked about, remember the things you can say," "Here's the brown paper bag.

Take a couple of deep breaths. Everything's gonna be fine." It impacts the spouse just as much

Jeffrey Feldberg: And Deep Wealth Nation, wouldn't you want to know upfront that with your spouse, I'm just gonna make this up. by the way, Cindy, I am not a golfer, but imagine I was a golfer. Said, "Oh yeah, I'm gonna be golfing every day of the week, and I'm gonna have my spouse doing that with me," or, "I'm gonna be traveling the world.

My spouse is gonna be doing that with me." And get there hey Jeffrey, I don't want to be golfing with you," or, "I don't really want to travel all that much." I would probably want to know that now, not later, to prevent some of the hiccups or the friction that could go along with that. And one of the benefits, Cindy, of working with you, again, you've been there, done that.

You've got the system. You know the questions, you [00:49:00] know the typical pitfalls, that it's a great point. Hey, let's design a life now. Not gonna be perfect. It'll change along the way, but let's design it now that for the most part, we're probably 90, 95% spot on, and you can make the course corrections as needed when needed with that.

Thoughts about that before we go into wrap-up mode?

Cindy Jennings: I'm with you 100%. I think if I just stick with the spouses, I have another story really quickly. They had been talking about the sale, and he was like, "Oh, I think I'm three to five years out." And by the time we were about six weeks in, he's like, "I'm putting this on the market tomorrow," and so his wife was like, "Whoa whoa, whoa, whoa, whoa. Like, I know we talked about this, but I mean, you just escalated. You just, put this up, three to five years earlier. I was not ready. I thought I had time to prepare for this." And so when we really dig into the issues her outward fears were about divesting, right?

Like, how are we gonna survive on this? And again, before he even sold the company, they were fine. We're talking about spending multiple tens of thousands in a month, right? It's like they're [00:50:00] good. But she was worried about Medicare. And, they do not need to worry about Medicare, but that was how her anxiety, how her fear was manifesting.

And so then just bringing them aligned, you know, as he was putting the business on the market, that he could say, "Oh, okay, I understand where her anxiety is coming from. We can start to address this now," and show her the financials and show her where we're at and show, you know, doing some of that just alleviated her fears, but it hadn't occurred to him to do that until I was like, "You know this is not about Medicare, right?

This is you expediting the sale process, and she's freaking out 'cause she thought she had more time to mentally and emotionally prepare for this exit." So

Jeffrey Feldberg: Exactly. And whether it's our spouse or our family, I'll use general analogy and then we'll go into rapid mode from there. Maybe kids are the better example. If I'm in the kitchen, I make something for the kids and I give it to them versus the kids help me prepare the meal, odds are if they help prepare the meal, they're gonna eat the meal versus me preparing it, I just [00:51:00] show up, "Okay, here you go."

And so if we take that very simple analogy, it's probably oversimplified. If my spouse, if my family members are involved in, "Okay, here are the plans for my post-exit life. Here are the plans of while I'm in the business and pre-exit," and they're a part of that, we don't have to explain later why'd you do that?"

Or, "Why didn't you do this?" Everyone is part of the journey together, and it's so much easier for everyone where transparency, accountability, everyone has a say. It doesn't mean I'm gonna listen to them,

or maybe I am gonna listen to them. I never thought of that. You're right. You know me better than I know me."

Whatever it's gonna be, everyone has a voice at the table, and then I'm making informed decisions, and that's where we wanna be. So that said, Sendy, my goodness, we can just go on and on. I absolutely love that. It is time to wrap up. 

Back To Future Advice

Jeffrey Feldberg: It's a tradition here on the Deep Wealth Podcast. It's my privilege, my honor.

Every guest I ask the same [00:52:00] question. It's a fun one. 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 Sendy, the fun part is tomorrow morning you look outside your window, not only is the DeLorean car curbside, the door is open.

It's waiting for you to hop in. You know what you do. You're now gonna go to any point in your life, Sendy, 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 life wisdom? "Hey, Sendy, do this, but don't do that." What would it sound like?

Cindy Jennings: I would say I have always been business-focused, and I would also say, "Hey, Sendy, don't take it so seriously." Take it seriously enough to achieve the goals that you want, but also go have more fun. Go find more freedom to have fun

Jeffrey Feldberg: Love that. Hey, enjoy. Have more fun, have more freedom, have more fun. Love where you're going with that so much. In our minds, we make it worse than it actually is. 

Where To Find Cindy

Jeffrey Feldberg: And Sendy, all of that said, someone in Deep Wealth Nation, they have a question for you. They [00:53:00] want you to help them, help their team. Where's the best place online to reach you?

Cindy Jennings: You can always reach out to me on LinkedIn easily s- Cindy L. Jennings. I think linkedin/cindyljennings. You can also find me at lifewiseexit.com, and you can e- do- email me at cindy@lifewiseexit.com

Jeffrey Feldberg: And the great news, Deep Wealth Nation, doesn't get any easier. It's in the show notes. It's point and click. Just go there. It's waiting there for you. And Cindy, congratulations. It's official. It's a wrap. 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

Cindy Jennings: Thank you, Jeffrey. Great to be here 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. 

What did you think? 

Subscribe And Final Thanks

Jeffrey Feldberg: 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 [00:54:00] and keep these episodes coming to you.

Are you ready for it? 

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.

And every time you subscribe and a fellow entrepreneur subscribe, it's a testament to how together, Yes, we are. We are changing the social fabric of society. One business owner at a time, one liquidity event at a time. So don't let the momentum stop here. Subscribe now on your favorite podcast channel.

You'll never miss an episode. You'll be the first to hear from the top industry leaders, the innovators, the disruptors that are really changing and shaping the business world, and [00:55:00] maybe you're commuting, maybe you're at the gym, maybe you're taking a well deserved break that we spoke all about on this episode.

The Deep Wealth Podcast, it's your reliable source for the next big idea that could literally revolutionize your business. So once again, please hit that subscribe button, stay connected, inspired, and ahead of the curve. And again, your next big breakthrough moment, it might just be one episode away. Maybe it was even this episode.

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.