For entrepreneurs, retirement isn't just a financial milestone. Often, it can be an identity crisis waiting to happen. After decades of building a business that defines who you are, what happens when the alarm clock, the purpose, and the daily grind disappear overnight? And how do you transition into a retirement that actually feels fulfilling?

In this episode, host Nick Carman is joined by Dustin Terry and Mike Zaccardi, along with a special guest, Clear Harbor's Senior Wealth Advisor and resident CFP Jerry Skalsky, to dig into what it really means to retire well as an entrepreneur. Listen in as they cover the psychological side of stepping away, how to define your “freedom number,” and why a conservative portfolio can quietly put an early retirement at risk.

 

What You'll Learn:

  • Why entrepreneurs need to retire to something, not just from their business.
  • How a founder’s identity gets tangled up with their company.
  • The three keys to a fulfilling retirement.
  • What determines whether retirees actually feel content.
  • How to define your “freedom number” by separating needs, wants, and wishes.
  • Why inflation is a bigger threat for entrepreneurs retiring early.
  • How risk tolerance differs between entrepreneurs and W-2 employees.
  • How serial entrepreneurs can balance funding a new venture against protecting the wealth they’ve already built.
  • Why ongoing financial planning can reveal when you can safely de-risk your portfolio and focus on legacy.

 

Ideas Worth Sharing:

  • “If you just stop working and don't have something planned to do with your time, you're going to be bored as hell.” - Dustin Terry
  • “The money is the easy part. The research is clear that the most content and purpose-driven retirees are the ones that have a good social circle.” - Mike Zaccardi
  • “Don't always assume that conservative means safe. We can be in highly conservative positions and still not be keeping up with inflation.” - Nick Carman

 

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Disclaimer: Founder's Fortune is intended for informational and educational purposes only. The opinions expressed by the hosts and guests are their own and do not necessarily reflect those of Clear Harbor Wealth Management.
 

Nothing discussed on this podcast should be considered investment, legal, tax, or financial advice. All investing involves risk, and listeners should consult their own professional advisors before making financial decisions.

 

Transcript:

You built a company, you carried the risk. But when it comes to your wealth, your exit, and your retirement, who's helping you? 

Welcome to Founder's Fortune: How Entrepreneurs Build Wealth, Freedom, and a Lasting Impact. I'm your host and small business expert, Nick Carman. 

Each episode, I sit down with our founder, Dustin Terry, and Mike Zaccardi, our director of research, to explore how founders transform business success into enduring wealth. 

Let's get started.

Nick Carman: Hi everybody. How are we doing today? 

Dustin Terry: I'm doing great. 

Jerry Skalsky: Awesome. 

Mike Zaccardi: Good. Nice.

Nick Carman: What is everybody's plans for 4th of July? For our listeners, we're recording this just a couple days before the 4th of July and gearing up for a big weekend here. What's everybody's plans? 

Dustin Terry: So our office here in Destin overlooks the harbor, and the fireworks show is right here that we will be able to watch from our balcony.

And you know we've got three young girls, so we'll bring them up here on the evening of the 4th and watch the fireworks show from the balcony. 

Nick Carman: No better view in all of Destin, I think. 

Jerry Skalsky: For sure. 

Nick Carman: Yeah. 

Jerry Skalsky: Yeah. I have an old neighbor that moved to Texas to be closer to his grandkids that they're coming back for about a week.

And so the neighborhood, we plan on meeting with them, doing a cookout. We're gonna do a beach on Saturday, that type of thing. So that's kind of our plan. 

Nick Carman: Yeah. Yeah. Mike, you're a little bit further from us, so anything different happen in your neck of the woods this 4th of July? 

Mike Zaccardi: No, not a whole lot. No, nothing too crazy, I don't think. 

Nick Carman: You're gonna keep all your fingers, you think? 

Mike Zaccardi: Yeah, I plan on doing that. Hopefully have a big steak or two, some good old American meat and potatoes on Thanksgiving, some hot dogs, all the good stuff. 

Nick Carman: Good. Good. Yeah, Destin, I'll be on the opposite side of the harbor here, watching from a friend's place.

They got a deck that will point perfectly at the fireworks, so we'll be watching from two different angles. So for our listeners, the elephant in the room is we've got a guest today, and so I'm really happy to have Jerry Skalsky here. Jerry is Clear Harbor's senior wealth advisor and our resident CFP, so really excited to have his perspective on today, and we're talking about retirement.

And more specifically, we want to get into what are we advising clients to retire to? What is the purpose? What is the vision? And I think Jerry is a great person to add some context and texture around that. So Jerry, I'd love if you'd just take a quick minute to kind of introduce yourself and your role within the firm and your experience working with retirement plans and that world.

Jerry Skalsky: Yeah, fair enough. Yeah, so my role is really do the financial planning. So I have all those meetings. I get the data that I need to help them set goals and priorities in retirement and kind of answer big questions of, "When can I retire?" "Do I have enough?" "Is my money gonna last?" A lot of little side questions come out of that.

"What do I get from Medicare? How does that work? When should I take Social Security?" All those types of questions. But I'll say a common theme, if you're a business owner, and to be honest, even if you're not a business owner, is the key thing is to retire to something. I'd say a lot of people that don't own a business, they want to get away from their job.

That's the big thing, and then they turn around and haven't thought of that. And to be honest, sometimes business owners, it's the same thing. They're so wrapped up in the business and looking at that, they're concerned about their employees, they're concerned about their clients, and they haven't really thought about retirement.

But generally, to be successful and happy in retirement, there's three things I always say need to happen. That is, can you live where you wanna live? You need to think about that. And it might be two different locations. It might be, you summer somewhere and you winter somewhere. That's real key.

The second thing is, do I have access to the people that are important to me? And generally, that's gonna be the grandkids and the kids, those types of things. And the third thing would be, can I do the things that I wanna do? That might be golfing, that might be buying a boat, fishing, traveling the world.

And in financial planning, a lot of times people think of that generally, but what's really important is to really make it more concrete and really put numerics to it. So you want a boat, let's talk about that. What kind of boat do you want? What's that gonna cost? You wanna travel the world. What's that gonna cost? We need to have that in there.

And specifically, I would say to really build a clear vision for what retirement is for you, and to make sure you're on track to accomplish that. And to be honest, that may, over the years, that changes a little bit, and you kind of fine-tune it, but I think that's really key in terms of retirement, is getting those three things in line.

Dustin Terry: Yeah, and I'll just go ahead and add onto that. From the entrepreneur's standpoint, Jerry talking about having plans and what you want to do in retirement, he mentioned a lot of those recreational things that people think they're gonna do, right? And yeah, you're gonna do some of that.

But being the entrepreneur in the room here, I understand the mindset and the personality of the type of people we're talking about here, and we start talking about retirement, and Jerry said, retire from something to something. Yeah, you wanna have goals and visions for what that retirement looks like, but you need to have some purpose too, right?

For 30, 40 years you've been jumping out of bed at 4:00 or 5:00 AM to go run your business, to put out fires, to do things that give you meaning and purpose. And so to then just turn that off on one day and then okay, you go play golf, you go fishing for a while, but eventually you have to have something that gives you some purpose.

Maybe it's grandkids, maybe it's a charitable organization, maybe you start a new side job, open up a little coffee shop, whatever that might be. But I can just tell you with the type of personalities that we're talking about with these entrepreneur clients, if you just stop working and don't have something planned to do with your time, you're gonna be bored as hell.

Jerry Skalsky: That's fair enough. 

Nick Carman: And what would you say are some of those markers for you when you're talking to a client, maybe if you have some examples of this, but where you see an entrepreneur that financially they're ready, right? We did the planning. We took a look at what their freedom number is, which we'll talk about probably here in a minute but they're not psychologically ready, right? They really haven't set that next target. What are some of those markers for you? 

Dustin Terry: Yeah. Psychologically ready, right? Their business is their identity, right? I mean, 30, 40 years of doing this thing. “I am, I own…"

You ask somebody who they are or what they do, they tell you about their job, right? And that is especially true for an entrepreneur, a business owner. “I own an HVAC company, I own a wealth management firm, I own an insurance agency,” right? That is their identity. And so it's just incredibly important to understand what that identity is going to be in that transition to retirement and understanding that it's going to change, and that is what a lot of times gives people a hangup with making that transition into retirement and deciding to just keep working, letting the business wind down, is because they don't really know who they're going to be once they hit that retirement date.

Jerry Skalsky: See, I can ask questions too, right?

Nick Carman: Yeah, go for it.

Jerry Skalsky: So, Dustin, I was thinking, a lot of times I think for business owners that have employees, that's real important to them. I mean, they're really tied to their employees, invested in their employees, and even their clients. Right? And I mean, they've got to feel comfortable that they're passing this business off, if you will, to someone that's gonna feel the same about their employees and about their clients, and I think that's helpful, too, for them to kind of get into their retirement years and feel comfortable and confident in that piece of it also.

Dustin Terry: Yeah, that's a great point. I mean, when we start to think about some of the topics we'll cover and exit planning's gonna be one of them, that certainly falls into that category of the planning around the exit is what happens to those people that are close to you in that business. Once again, go back to identity, right?

Those people are most likely all your friends, too. That's who you spent all your time with, and you're gonna lose your purpose, you're gonna lose your identity, and you're gonna lose your friends. Your friends. Yeah. Right? So is there any reason that sometimes people just put that decision off?

Nick Carman: Mike, what does the research say around what a successful retirement looks like versus one that leaves people kind of without meaning? 

Mike Zaccardi: The most important factor is clearly your social connections. There's no doubt about that. The money is the easy part. Getting to your freedom number, it may sound daunting for some people, especially early in their career, but I mean, generally, if you just set good habits, invest into a low-cost portfolio, basing your goals, you're gonna get there by traditional retirement age. So beyond that, the research is clear that the most content and really purpose-driven retirees are the ones that have just a good social circle.

It really comes down to the basic things: your friends, your family, how close you are to your loved ones, what your day-to-day looks like, what your Sunday looks like, and what your Tuesday looks like.

If you can nail that, and if you're already doing that in your working years as an entrepreneur, you're in good shape.

And, unfortunately, this comes down to a personality trait in a lot of instances. I mean, some people are, just naturally very gregarious, and they keep up with friends. They enjoy asking that question, "Hey, let's go, have a coffee or take a walk."

Others, normally men, are less inclined to do that, so they can struggle a bit more. So, when you think retirement, the first thing you think about are the dollars and cents and your income generation, Social Security, Medicare. But potentially, you'll have to think more about the softer side of things.

And that's partly why a good financial advisor is also part therapist at times to really help individuals get ready for that. 

Nick Carman: Yeah, and it's so important what you talked about, right, that social circle. And I'd add to that, expanding it a bit before we're in retirement.

I think about my parents, and their whole, like, purpose behind retirement was they wanted to spend as much time together as they could, right? That was their plan. And life happens. Dad passed away, like, six months or so after retirement, and so Mom really doesn't have a plan, right? And so over the last few years, it's been about six years, and so in that time, she's just now starting to find that community again, find that purpose.

And my wish for them is that they were having these conversations earlier, identifying the work in the community or identifying the hobbies, identifying those call it church groups or women's groups or whatever it is that she could have been a part of earlier to kind of grow that, that circle of community around her.

Dustin Terry: Yeah, that's a great point, too, Nick. Like, one of my favorite outcomes when dealing with clients or entrepreneur clients is, they're thinking they might retire in 5 or 10 years, and then we get in, we start having these conversations. Some of them are like, “I know exactly what I'm gonna do with my time."

And then we start going through the math and the quantifiable stuff that we think the business is worth and how much they've gotten saved already, and we say, "Okay, you could do this now. Would that be of interest to you?" And then that's just a really, to your point, about losing your dad early on in retirement, if you can do that and you can give...

And people have more years in a healthier state with their family and friends, that's just a tremendous outcome in my opinion. 

Jerry Skalsky: I think really to add upon that, it's not just the social connections what's important, but physically be healthy, and be prepared, if you will, in retirement.

You need to stay active, if you will, and that needs to be kind of talked about, too, 'cause a lot of times people get into retirement and they can't do the things they want 'cause they physically can't do it anymore. 

Nick Carman: Yeah. It's amazing how quickly people start to fester when they don't have a place to be, right?

Their whole career, they've run this business. Maybe they're working 30, 40, 50, 60 hours a week. They have a place to show up every day, right? And so having that purpose continue past retirement. 

Jerry Skalsky: Yeah, and I'll say, the other thing is, if your job is labor, it's physical intensive compared to you're sitting behind a desk, it's more mental, if you will. Sometimes they're forced to retire 'cause they physically can't do their work anymore.

Nick Carman: I think that we kind of went through the psychological, the personal, right? I want to get into the freedom number, right?

Finding that freedom number. This is one of the main themes of the retirement chapter of the book, and we've touched on it a little bit. It's more so than a simple, "Here's the cash flow needed to meet basic needs," but really, it's about creating a financial plan that gives them the life that they want and security that they want.

So I'd love to know, Jerry, when you are working with clients prior to retirement, how have you been able to help them create that vision in not just what they need, but really what they want to be able to live the life that retirement?

Jerry Skalsky: Yeah, and I always think of needs, wants, and wishes.

So needs are just the basic things that you keep your roof over your head, pay your utilities, all those types of things. But what are the things you want to do? And I actually encourage them to think beyond that. If you really had the money and you really wish, what could you do? And start to quantify those things. Sometimes people make bad money decisions not because they're not smart, is they don't have a clear vision for their future is sometimes is... you think about it, if it's physical and you want to get in better shape, well, you got to have a vision for that. And I always say two twins come with a vision automatically: motivation and discipline.

And part of what I try to do, especially in the goal development, is really pull from people what their vision is for their life and again, start to quantify that, start to articulate that, and that creates a clear vision. And I always say motivation and discipline come with that. They figure better ways to save, as an example, and they kind of hold each other accountable for a married couple.

But I think that's really important in doing planning is be clear. You got to have a clear vision of where you're going. And it's in them, right? But often, a spouse and a husband, they don't talk to each other about it, and they might say something here or there. And I think as a financial advisor, what I'm trying to do is pull that out of them.

It's there, right? And you've got to just pull that out of them, and then we start to quantify. It's good conversations between spouses, and having that, bringing that up. And the reality is it's not one and done, so from year to year, your vision is going to get fine-tuned and become more clear, especially as you get closer to retirement.

And so that's what I try to do when I think about that. 

Nick Carman: Have you had any clients that, as you kind of go through your annual or biannual strategy sessions, that all of a sudden that vision shifts drastically, gets turned on its head? 

Jerry Skalsky: Yeah, sometimes. We had a client last year, and I think I mentioned this to you earlier, Nick, they're someone that there was a place they wanted to buy.

They wanted to buy a boat. They wanted to be on the water, and they thought it was down the road, if you will. And we did all the numbers; we talked about their goals, and I said, “You can do that now. You've got the money to do that now." And they're like, "Wow," surprised. And they did. They were able to go buy that home and buy that boat.

Dustin, we're talking about a client right now that they wanted to sell their business in a few years. Well, that changed, right? After we kind of ran some of the numbers on them. Well, they can retire now, sell their business now instead. 

Nick Carman: Yeah. I bet those are pretty fun conversations to have, huh?

Jerry Skalsky: Yeah.

Dustin Terry: Yeah, those are the best.

AD BREAK

Hey, quick pause before we continue. If you're thinking about your next chapter, whether that's growth, transition, or retirement, we created the Founder's Fortune Assessment to help you evaluate your current strategy.

It's designed to uncover blind spots, identify opportunities, and give you a clearer picture of your financial planning and investment approach. To begin, visit foundersfortune.net or use the link in the show notes. Now, let's get back to the conversation.

AD BREAK END

Nick Carman: So what are some of the risks, as we're kind of looking at the freedom number, what are some of the risks that your casual investor or your casual business owner that's not getting the right advice, where are they missing?

Dustin Terry: I think, well, Mike, take that one. It's probably gonna tie into capital market assumptions and all those things in terms of some risks to the planning.

Mike Zaccardi: Yeah, I think it comes down to more your lifestyle necessarily than the portfolio. I mean, these days it's easy to get into a good portfolio, whether we're talking a W-2 employee or an entrepreneur, they know that they can set aside money, and that'll compound over the years, but if you don't get into that habit, that's where you get tripped up.

So over time, as expenses build up and you don't prioritize yourself, maybe you're thinking about your kids first or just any other priorities that come up that don't put your retirement near the top of your financial to-do list, that sort of thing can get out of whack.

And it's just one of those things where it doesn't happen in, one fell swoop, it just, over time, as much as an investment account can compound, so too can your mistakes. And a lot of times the mistakes are not errors of commission; they're errors of omission, and that's where a good financial advisor, partner on your wealth journey, any phrase you might wanna use, that's where they can just help you stay on track.

It's not any big thing necessarily; it's just keeping those guardrails intact that can do that. So just being intentional and getting most of the things right, I think, will get you most of the way there. 

Dustin Terry: Yeah, and another thing I would say in business owners and mistakes in terms of retirement planning is they always think they're gonna make so much more money next year, and “I'll do it next year," and then that happens for 15 years.

And then all of a sudden now we've got to, okay, well, we have that gap when we're talking about that freedom number in terms of what they need in terms of wealth to retire and live the way they want. So the risk is that they're just way... they've waited too long, they're unprepared, and now we've got a big gap to make up.

So to the point of Jerry's work and the planning that he does is, well, let's know what that is now. Let's not wait until we're ready to pull the plug to see, okay, what do we need to do to retire next year? The sooner that you start that plan, the better, so then you know what that freedom number needs to be.

You know what the business needs to be worth. You know what you need outside the business. You know if you have any income sources, what your Social Security's gonna be worth. So the biggest risk, I think, is just not having a plan in place. 

Nick Carman: I was thinking a little bit about entrepreneurs in general, and so far we've been talking about the entrepreneur that opens a business or maybe they purchase a business, they work their career there, they build it all in one place, and then, hopefully there's an opportunity for a liquidity event.

I'd love to know how these conversations differ when we're talking about that serial entrepreneur, the one that has to chase after the next thing, and maybe they've already gone through a couple of purchases and sales. I'd love to know how we kind of help them navigate how much they can put into the next venture versus putting it together in a retirement plan.

Dustin Terry: The first thing you have to do there is get spouses on board with each other with that type of personality, right? So you have someone, a couple, they have this liquidity event, they have an exit. One spouse, usually the wife, thinks they're set. Usually the husband's the one that wants to go take most of that money and start a new venture.

And so then we have to take that counseling role that Mike mentioned and, okay, well, what is going to provide you your comfort and your lifestyle that you want and need, regardless of whether how this new venture pans out, right? So, back to the whole purpose thing, the entrepreneur is like, "Oh, it's gonna work out, right? Of course. Like, I've done this once," right?

"So surely I'm going to do it again, and it's gonna go great." But yeah having that base plan in place, making sure that those base needs, wants, and wishes are taken care of, and then you say, "Okay, what is left over here, you can go start this new venture and roll the dice with that."

Nick Carman: I love that. When we're looking at our entrepreneur business owners, a successful business owner, it's not uncommon for us to see that they're retiring much earlier in life, and you kind of touched on this a little bit, Dustin. And so we're talking about people retiring in their 40s and their 50s rather than their 60s and their 70s.

And so what are some of the gaps in a “conservative strategy” that can lead to going broke safely? 

Dustin Terry: Yeah. So, if you're retiring at an earlier age than typical, you have to plan for the silent destroyer of wealth, inflation, and we all know about that, right? Since COVID, it's come back into the lexicon.

Hasn't really been an issue since the '70s. But if you are, with talking with the client the other day whose early 50s, going to retire probably soon, and that could be a 40-year period of retirement, right? And think about the rule of 72. 72 divided by the rate of return is how long it takes for your money to double, right?

If you think about a 3% inflation rate, that means that the prices of goods and services double every 24 years. Okay, so you're talking about now, talking about a 40-year retirement period, everything's gonna double twice. 

Right? So you have to invest to not only grow your wealth, but to just maintain the level of wealth that you currently have.

And I talk to clients about this all the time. Our clients, they've been successful. The types of things they're spending money on, ribeyes like Mike, those are not inflating at 3% a year, right? Yeah. First class plane tickets are not inflating at 3% a year. Luxury vehicles are not inflating at 3% a year.

It's 5, 10, maybe 15% in some instances. So you have to invest not only to maintain or to grow your level of wealth, you have to invest to maintain your level of wealth because governments are gonna keep printing money, right? And so inflation is going to be a fact of life, and you have to plan for it.

Jerry Skalsky: Yeah. Just to add on that, healthcare: you're 50 years old. You're not gonna get Medicare till you're 65. I mean, now you gotta deal with that yourself, and that's really taken off in cost too. Plus if you get sick, someone gets sick during that period.

Mike Zaccardi: When it comes to investing for retirement and inflation, stocks over the long run tend to be very good inflation fighters. Right. So sticking with that and not getting too hung up on some of the rules of thumb, like there's that old adage out there, like 100 minus your age, and that's how much you should have in stocks and bonds.

That may not be the, make the most sense in most circumstances. And something else to consider in today's environment as I kind of look at the investing side of things, while bonds have taken a big hit since interest rates rose and inflation kicked up around 2020.

Today they actually offer, if you look at some of the inflation-protected bonds, some decent yields relative to the last decade plus. So, those are some things to think about when it comes to investing for retirement. In some situations, there's kinda good news today versus what we were looking at five, seven years ago when those inflation-adjusted bond yields were negative in some situations.

And now they're nicely positive. So, you can get kinda lost and scared out by some of the horror stories in bonds, but that's a situation where taking a fresh look at what's out there in the investable universe can offer more, open more doors towards reaching good rates of return to hit your goals.

Nick Carman: Yeah, that's great. That's great. I was kinda reminded about risk and risk tolerance. Dustin, would you say that there's any differences that you kinda come to find in the type of personalities that entrepreneurs, that differs in risk tolerance? From a W-2 employee, do you think that there's a difference there?

Dustin Terry: Generally, they are more of the risk-taker mindset, but I think that's with things that they control. I understand my business. I'm going to lay it all on the line here because I understand it and I control it. A lot of times, they're putting everything back into the business to grow the business, which, as Mike discussed on the last episode or our first episode, that can absolutely be the best course of action in some circumstances.

But getting them from that, "I control my business, I'm gonna invest in me," to then invest in things that are outside their control, sometimes that can be challenging, right? Some of them have been investing in the stock market and putting money in a retirement plan their whole career, and it's not nothing, it's not new to them at all.

But some of them, it can be a challenge to say, "Okay. Well, I've never done this before. I've never put money in the market. I've only ever had money in my business." But then we have to have that conversation, "Well, you have to outpace inflation somehow, right?" Well, either you keep working and save more to put into CDs where you're gonna go broke safely, or you invest to outpace inflation.

Nick Carman: Yeah. And I like what you talked about the control aspect, and I think that's important when we're talking about business owners and entrepreneurs, that aspect of not just I can't control what's in the stock market, but moreover, I'm handing it in the case of clients at Clear Harbor, I'm handing my finances over to a team of experts, and I have to trust that they're able to control it, right?

And so it's kind of two levels removed. And so being able to have those conversations about how we handle the risk and how we approach that investment strategy is super important. 

Dustin Terry: We can't control the markets. We can't control what happens to the broader market. What we can control is knowing what we own and why, right?

And we write a lot about that, and Mike puts out a lot of good stuff on that. But, as long as you understand, hey, for the entrepreneur, that's what we try to equate it back to. Don't look at this as the stock market. Look at this as you're owning shares of these companies that have people like you that are running much bigger organizations that are trying to drive an organization forward, right?

And so then if you can get that into their mindset, "Okay, I'm buying shares of ABC Company," probably shouldn't use ticker symbols now, 'cause I think all matter of tickers have been put together into some ticker symbol at this point. But you're buying shares of some company where they are trying to drive an outcome, sell a good or a service.

And then if you can equate it that way, I think that helps get the point across. 

Nick Carman: So for the entrepreneur that's listening right now, and they're, let's say, five to 10 years out from retirement What are some of the key things that they should be thinking about now, and what do we want them to take away from this episode?

Dustin Terry: I'm gonna let our esteemed guest, Mr. Jerry Skalsky, take that one. 

Jerry Skalsky: Well, yeah, I think financial planning just benefits so much just going through that process. A lot of times, when they first meet you, trust is based on knowledge. Does that make sense? I'll just give an example. When I first met my wife, and I loved her, I was infatuated, but the longer I get to know her and have more experience with her, the trust just deepens, if you will.

And I think financial planning lends itself to two things, is not only do we get to know people better 'cause we're spending that time talking about their goals, getting all their information, things like that, they get to know us better. And I think that's really important. And then the other thing I don't want to de-emphasize this, 'cause I've noticed this a number of times.

At the end of the financial planning process, we come up with great advice. We come up with some good tax advice. We come up with better rates of return, all kinds of things, and a lot of times, you know what the people are most happy about? Is they went through the process. They feel like they know where they're going.

They got a vision of where they're headed, and what's that worth? Can you go to the bank and someone help you create a vision for your life financially? I just think that is so important. Just going through that process will lend itself to, I think, a lot of things like that, and you really knowing where you're going.

Nick Carman: It does. It does. For any entrepreneur that has an advisor right now, what questions should they be asking their advisor, and where can they kind of see there might be some room here in that plan that's not being addressed? 

Jerry Skalsky: I would just say, a lot of times, other advisors don't do planning.

We used to call them tissue plans. They're really soft rule, based on rules of thumb, and they don't really have deep conversations about things. I think a-advisors miss that. I'd say traditional advisors are trying to get to some kind of sale, low-hanging fruit, if you will.

And what we do here is we want to start with really understanding you, understanding what your needs, what's important to you. And the advice we provide, to be honest, written advice and objective advice, we don't want to brand it. We don't want people to feel obligated, if you will, to work on that side of the product side with us.

And we want them to make decisions with confidence and conviction, and they know what they're making for a decision, and they feel confident with it. 

Nick Carman: Some of my takeaways today, just, hearing you guys speak about this is, don't always assume that conservative means safe, right? We can be in highly conservative positions, and that means that we're actually not keeping up with inflation.

And then, really, and this goes back to, story about, my parents, is decide ahead of time what you're retiring to, not what you're retiring from, and have vision for what life looks like after, and realizing it's not the finish line, right? Retirement isn't, "Oh, we made it," and everything's done.

That's just the next step, the next venture, if you will.

Jerry Skalsky: I think that's important, too, is, sometimes by going through the plan, especially business owners, they're pretty aggressive and been aggressive their whole life. We run all the numbers, and you know what?

You don't have to be aggressive anymore. Why risk your plan and be too risky, if you will? You don't have to.

Jerry Skalsky: And I think that's really powerful.

Dustin Terry: I think I'm gonna jump in here now on that, Jerry, 'cause we had the conversation with a client this week who has done exceptionally well.

They've s- they've saved a ton of money. Thankfully, markets have done really well the last few years, and we're updating their plan, and we're in the middle of the... And I'm looking at their goals.

Jerry Skalsky: Yep.

Dustin Terry: Jerry’s updating all that stuff, and they're just shooting the lights out in terms of where they're gonna be and what their goals are.

So we're now starting to talk about legacy, because they are so ahead of what their needs, wants, and wishes are gonna be that we're talking that we've got estate tax issues. We've got all these other things that are now other problems that have to be solved, but they're really good problems.

Yeah. But the first thing we did is said, "Hey, we’re gonna back down your risk on the portfolio 'cause there, you have absolutely no need, even factoring in that long inflation time that we're thinking about, they have absolutely no need to take any risk, an inordinate amount of risk.

Jerry Skalsky: And that's emotionally meaningful to them. 

Dustin Terry: Yeah. Yeah. Right? It was a big relief because then you're thinking, it takes less... They're looking at their accounts less. It's just a relief off their shoulders. But yeah, that's why Jerry always says, planning is not an event. It's an ongoing process. Those things change. 

Nick Carman: Well, thank you, gentlemen. I think that we've got a ton of really awesome takeaways for our listeners today, and I'm just looking forward to having a continued conversation. Jerry, we can't wait to have you back on the show. We'll have more episodes with Jerry here. And everybody, have a safe and fun 4th of July. Thanks, guys.

Jerry Skalsky: You bet. Thank you.

We hope you enjoyed this episode of Founder's Fortune. You can get your copy of the book on Amazon or through our website, clearharborwealth.com. If today's episode gave you a new perspective on your business, your investments, or your long-term wealth strategy, the next step is gaining clarity, and our firm can help.

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