This Is the Exit Strategy Most Founders Miss | Dan Pascone with Evan Duke | EP #46

Most founders wait too long and go into a sale unprepared costing them money, options, and peace of mind. In this episode of the Making Sense of Your Money podcast, host Dan Pascone interviews business exit planning strategist Evan Duke about what owners get wrong when selling a business, why serious exit planning should start 5–7 years before a sale, and how issues like customer concentration, key-person dependence, and lack of leadership depth can kill value in due diligence. They also discuss buyer types (strategic, PE, family office), how earn-outs actually work, and why aligning your exit with a clear life-after-business plan often determines whether selling feels like freedom or regret.

• We’re entering a massive exit wave (“silver tsunami”).

  • A huge percentage of privately held businesses are expected to change hands in the next decade as baby boomer owners retire.
  • Evan cites estimates as high as 74–88% of businesses attempting a sale in the coming 10 years.
  • That creates both opportunity and intense competition for founders who want a successful exit.


• Ideal exit-planning window: start 5–7 years ahead.

  • “Day one” exit thinking is great, but for most owners, a realistic sweet spot is:
    • 5–7 years before you might want to exit (start thinking strategically).
    • 3–5 years before exit (engage an exit advisor and implement changes).
  
  
  • Key fixes diversifying customers, building a leadership team, reducing reliance on the owner take years, not months.
  
  


• What buyers hate: concentration and key-person risk.

  • Customer concentration: One client at 80% of revenue is a giant red flag; buyers see “single-point-of-failure” risk and may walk or heavily discount.
  • Founder-centered relationships: If buyers “can’t see the difference between you and the business,” they’ll fear revenue walks out the door when you do.
  • No team, no sale: A business with no employees or all value tied to the owner’s personal efforts and IP is often unsellable in its current form.


• Buyers you may encounter and why they matter.

  • Strategic buyers: Competitors or related operators (e.g., an HVAC roll-up) looking for synergies, complementary services, or geographic expansion.
  • Financial buyers: Mainly private equity professional buyers who acquire, improve, and later resell businesses.
  • Family offices: Longer-term capital with their own unique criteria.
  • Most are professional deal teams reviewing dozens of opportunities (Evan mentions PE firms often look at ~80 deals before buying one).


• Unsolicited offers are rarely the full story.

  • Example: an owner gets a $52M unsolicited offer; after a proper process, fair value turns out closer to $70M.
  • Lesson: don’t assume first offer = best offer. Without advisors, you’re negotiating against professionals on uneven ground.


• Business valuations vs. what buyers pay.

  • A formal valuation is helpful for expectation-setting and benchmarking.
  • But: there’s a difference between “valuation number” and the actual price buyers are willing to pay in the market.
  • Many M&A firms “test value” by quietly surveying potential buyers on what a business like yours might be worth.


• Earn-outs are increasingly common.

  • Trend: a growing share of deals include earn-out structures (additional payments if future performance targets are met).
  • Example: Instead of $10M up front, a deal might be:
    • $7M paid at close, plus
    • $1M per year for 3 years if revenue/EBITDA targets are hit.
  
  
  • Earn-outs let buyers de-risk; for sellers, they reward a business that keeps performing after you leave.
  
  


• Your business must be able to run without you (the 90-day test).

  • Evan’s rule: if you can leave for 90 days and the business runs smoothly, you’re closer to ready for a sale.
  • If you can’t be away for 90 minutes without fires, you are not ready.
  • Key steps:
    • Build a real leadership team (CEO/GM, COO, CFO/controller, etc.).
    • Document processes, controls, budgeting, and decision-making.
    • Shift relationships and visibility from “you” to the company brand and team.
  
  


• Meaningful life after the sale is critical.

  • Owners often underestimate the identity and purpose gap once the business is gone.
  • Dan and Evan both stress planning for:
    • How you’ll spend your time (beyond “move to Denver” or “travel more”).
    • New sources of meaning: mentoring, Vistage-type roles, board work, community impact, passion projects.
  
  
  • Aligning the business exit plan with your personal life plan often determines whether the sale feels like freedom or regret.
  
  


• You need a coordinated team: exit advisor + wealth planner.

  • Evan focuses on readiness of the business (operations, leadership, risk, positioning).
  • Dan’s team focuses on the owner’s personal side (cash flow, taxes, investing, life after work).
  • The best outcomes happen when business strategy and personal wealth strategy are aligned years in advance.

• (00:00) – Episode intro & setup. Dan introduces himself, the podcast, and guest Evan Duke, a business exit planning strategist, and frames the discussion around what founders get wrong about exits and how timing affects outcomes.
• (01:14–01:55) – Evan’s background story. Evan shares his path from aspiring professional musician and orchestra president into business operations and finance, and how he became focused on exit planning.
• (02:00–03:16) – The “silver tsunami” problem. Evan describes the demographic wave of baby boomer owners exiting and cites high estimates of how many businesses will try to sell in the next decade.
• (04:07–04:58) – Ideal client profile. Evan outlines the typical business he works with: $5–$50M in revenue, various industries, often founder-led and at the stage where the owner wants to move on.
• (05:10–05:49) – When to start exit planning. They discuss ideal timing thinking 5–7 years out, formally engaging an advisor 3–5 years before a potential exit.
• (06:20–07:58) – Biggest surprises in M&A. Evan highlights how owners underestimate due diligence and risks like customer concentration and personal-brand dependence.
• (08:26–10:01) – When a business is not sellable. Evan describes a stormwater business with patents but no employees or real infrastructure an example of a situation where a sale is very unlikely without major changes.
• (10:01–10:49) – Types of buyers. Evan explains strategic buyers, financial (PE) buyers, and family offices, and the importance of understanding who’s across the table.
• (10:49–12:49) – Professional buyers & under-offers. He explains how PE firms review dozens of opportunities and shares the story of a $52M unsolicited offer that turned out to be far below a $70M market value.
• (13:07–14:53) – Valuations vs. real-world pricing. Evan talks about using valuations to set expectations, but also why they don’t guarantee what a buyer will pay.
• (14:53–16:57) – Earn-outs on the rise. He explains the growing prevalence of earn-outs, gives a landscaping-company example, and ties earn-out success to how well the business runs after the owner exits.
• (16:57–19:14) – The 90-day test & leadership build-out. Evan details his method: org chart review, promoting internal leaders, formalizing CEO/CFO/COO roles, and documenting processes so the owner can truly step back.
• (19:14–21:28) – Life after exit and meaning. Dan asks about post-sale life, and Evan shares the Denver example and stresses the need to plan for purpose, not just geography.
• (21:28–22:21) – Aligning business and personal strategy. Dan connects exit planning with broader life planning making sure money, time, and goals line up.
• (22:21–25:27) – Lightning round. Fun questions help listeners get to know Evan: favorite meal (Supreme breakfast burrito), his TV as must-have tech, a quote from Kevin O’Leary, a favorite biography, and hiking to the Matterhorn base camp.
• (24:42–25:00) – Advice to younger self. Evan shares: “No matter how difficult things might seem to get, keep going” success often comes from not quitting.
• (25:27–26:26) – How to connect with Evan. Evan shares his LinkedIn (Evan B. Duke) and website (EvanDuke.com) as the best ways to reach him.
• (26:15–end) – Wrap-up & resources. Dan closes by mentioning recent storms, plugs makingsenseofyourmoney.com for more content, and reminds listeners to prioritize their version of a rich life.

In this episode of the Making Sense of Your Money podcast, Dan Pascone hosts business exit planning strategist Evan Duke to demystify what it really takes to sell a privately held business well. Evan describes how his background in music, orchestral leadership, and financial operations led him into the world of M&A and exit readiness just as a demographic tidal wave of baby boomer owners (“the silver tsunami”) is preparing to sell their companies.

Evan explains that many founders operate under a “work hard now, figure life out later” model. The problem, he says, is that “later” comes quickly: by the late 40s or early 50s, many of the best options favorable tax windows, strong leverage in equity negotiations, or flexible career pivots have already shrunk. He urges owners to think in terms of a 5–7 year runway for exit planning and to engage specialists at least 3–5 years before a potential sale to fix structural issues that scare buyers.

Among those issues, he highlights customer concentration (e.g., one client representing 80% of revenue) and key-person risk, where the owner’s personal brand and relationships are inseparable from the business. Evan shares stories of businesses that look impressive on the surface patents, strong accounts but prove nearly unsellable because there are no employees or systems that a buyer can reliably acquire. He contrasts that with the kind of company buyers want: one where leadership is in place, processes are documented, and the founder can leave for 90 days without chaos.

Evan also walks through the landscape of potential buyers: strategic buyers seeking synergies, financial buyers like private equity firms who are professional deal teams, and family offices with long-term capital. He warns owners not to get star-struck by unsolicited offers from PE firms, noting that professional buyers often review dozens of targets and may open with offers well below what a robust sale process could yield. A story about a $52M unsolicited offer later revealed to be under market by nearly $20M drives the point home: you need advisors to level the playing field.

On the valuation side, Evan stresses the difference between a formal valuation report and the price a real buyer pays, and he notes the growing use of earn-outs structures where part of the purchase price is contingent on future performance. He gives a simple example of a $10M sale with $7M paid up front and another $3M spread over three years if targets are hit. Proper preparation building a self-sustaining business can both reduce reliance on earn-outs and increase the likelihood of actually collecting them.

Throughout the conversation, Dan repeatedly connects the business-side planning to the personal side. They talk about how easy it is for an entrepreneur’s identity to be fused with their business and how important it is to answer, in concrete terms, “What will I do after I sell?” Rather than vague ideas like “move to Denver,” Evan and Dan encourage owners to think about mentoring, community involvement, passion projects, and other roles that provide meaning beyond work. Aligning the exit strategy with a thoughtful post-sale life plan, they argue, is crucial to avoid the emotional whiplash of a big liquidity event.

The episode closes with a light-hearted lightning round that humanizes Evan and a set of practical pointers on how to connect with him. Dan wraps by reminding listeners that the podcast, newsletter, and YouTube channel are all available at makingsenseofyourmoney.com and urges them, as always, to prioritize their own version of a rich life one that integrates money, time, and purpose.

Dan Pascone: I'm Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast real conversations to help high earners make sharper decisions so their money works as hard as they do. This is episode number 46. And today I'm joined by Evan Duke, who is a business exit planning strategist. And we break down what founders often get wrong about exit planning.

Dan: We talk about when you actually need to start preparing for an exit and why the business needs to run without the founder before a sale. Then we discuss how aligning your exit with your life plan determines whether selling your company feels like freedom or regret. Before we dive in, make sure you're subscribed on your favorite platform. And if you find the show valuable, I'd really appreciate it if you left a quick review. Thanks so much, and enjoy.

Dan: Evan, thanks for joining the Making Sense of Your Money podcast. Excited to have you today.

Evan Duke: Glad to be here and really excited to talk with you.

Dan: Yeah, likewise, likewise. We've been on break for a little while, so this is the first one back in 2026. So I'm excited to have you and talk a little bit about your business expertise, which is a really, really unique segment which is business exit, right? So for those founders, business owners, or even key executives out there, business exit is such an important time in your career from a wealth generation perspective. So I'm excited to chat with you about that. But first up, just tell us a little bit about your career track, how you've gotten into this, and currently what you do today.

Evan: Gotcha. Well, I actually started out wanting to be, of all things, a professional musician. I did my studies specifically on trumpet. I actually earned a doctoral degree, and it was actually during my work on that that I was beginning to realize that, you know, hey, we're right in the throes of the Great Recession and the recovery. And I realized chances of me finding a job they were not going to be that great, just because so many people were just holding on in college teaching.

Evan: And long story short, I really got involved with several music businesses and then kind of branched out. And I actually had a career for about a decade as the president of an orchestra. And really along the way, I just was able to get heavily involved in operations, really on the financial side with budget development and controls and really just such a wealth of experience.

Evan: As time was going on, I was beginning to realize we have a very serious issue that we're facing today, and that is with the silver tsunami, with all these baby boomers who are getting ready to retire, but more importantly, exit businesses. I have seen numbers as low as 74% and as high as 88% in terms of the number of businesses in the next ten years that are going to sell. You know, that's just insane when you think about it.

Dan: Cut.

Evan: And that's the big reason why I decided, you know, I really wanted to focus on this is because a lot of the work that I do is basically taking past experiences, but really trying to help make sure that each business is well built and ready to survive the M&A due diligence process, which anybody who's experienced it would know that it's very rigorous, very challenging. And there are just so many ways that you could wind up having value knocked off the business.

Dan: Yeah, absolutely. I want to get into that a little bit further, but paint us a little bit of a picture of the types of business owners and the types of businesses that you're typically engaging with. Because I imagine, you know, there's expertise in being able to work with certain size businesses or types of businesses. So tell us a little bit about the ones you typically operate.

Evan: Well, the ideal client we're talking about annual revenue between $5 to $50 million. When it comes to industry, it's less important, but it's more in terms of the actual stage of the business. Basically, it's where the business owner a lot of these businesses, baby boomer might have basically started this business in their garage, and they just built something that's impressive.

Evan: They want to exit, and they need help doing it. And so, you know, that's really who and what I am looking for. I mean, landscaping that's very hot right now, professional services. So really the profile will vary, but at the end of the day, it's really just that particular stage where the founder or the owner they’ve built a business, they're ready to move on, and I come in and help them do that.

Dan: Got it. Okay. When is the right time? I'm sure you're going to tell me the earlier the better, but when are you typically engaging with a business owner? When's the right time to start to prepare for a sale, if you will?

Evan: Well, theoretically, as you said, earlier the better. I've heard some people say really day one. But, you know, for those of us who aren't really don't have that much forethought I mean, most of us are like, okay, is this business going to actually earn something? We're not necessarily thinking about exit. But really the ideal thing is about five to seven years out is when you should start thinking about this because ideally you're coming to me three to five years from the exit saying, okay, now is the time for us to do this.

Evan: And a lot of it, it's not necessarily just getting things documented, it's getting the right people in place to make sure that this is a successful transition.

Dan: Yeah, and you know, I've got a number of clients who either have sold or are preparing to sell their businesses. And I oftentimes want to engage in a similar timeframe to discuss the opportunities that they have from a personal finance perspective. And you're obviously coming at it from a lens of the business and the corporate side. So what do you find are like the biggest challenges that a founder faces when they're looking to prepare for that rigorous M&A process that you referenced?

Evan: The biggest thing is just not realizing what is in store. And really, one of the big things is just the level of preparation. It's not necessarily about getting your books cleaned up, which, you know, that's an important part of the process. But it's the fact that, you know, trying to de-risk and things that we may have thought were a good idea, we realize actually they're not.

Evan: Like, I remember actually it was a call I had with a friend of mine who's an investment banker said that there is this one business who was really proud of this one particular account that they had built out. I mean, it was massive. It was 80% of their business. As soon as the M&A advisor heard that, they said, okay, we need to stop here, because that any buyer is going to look and go, okay, huge customer concentration risk.

Evan: So it's things like that. And it's really part of the reason why it's so hard is, again, it's things that we may not have realized was a problem. And one final example along these lines is, in addition to customer concentration risk, let's say you're a very friendly, people person. You are just making friends left and right, and in short, you've managed to leverage your personality to create an incredible network of people who do business with you.

Evan: Here's the problem: a buyer is going to look at it and go, okay, I cannot see the difference between you and the business. So sometimes it's that personal brand. So really, that's why having somebody come in and take a look at it through a different lens will help you see things that I thought were pluses were actually minuses.

Dan: Yeah, that makes a lot of sense. That key man risk or the business being so reliant on the owner is certainly real. But when maybe, Evan, do you look at a business and say, it isn't right for a sale or it isn't right for some sort of M&A activity? Like, how do you kind of help the owner evaluate that? And then what are their other options if maybe, you know, they have some of those risks that you mentioned earlier?

Evan: Well, really on the customer concentration risk, it's a matter of obviously like, okay, you need to find ways to not necessarily grow other accounts but bring in new accounts. And that's just gonna take some time. Really, a lot of the others like, for example, the personal brand that again is gonna take some time because you're going to need to find ways to basically make it more about the company and less about you.

Evan: Really, a lot of those again, it depends on the situation. And, you know, I'm gonna be rather frank, and this is something that I hope people will take seriously. There are gonna be some situations where a person is gonna be trying to sell something and I'm gonna say, this is not gonna happen.

Evan: And I think of one particular potential client I talked with last year. He had it was a stormwater drainage business. Just really impressive what he had done. But they didn't have a single employee. He had some substantial IP I mean, he had patents for the Eurozone as well as the US. So there was a lot of value to it. And he had some other assets that he owned.

Evan: But, you know, there were no employees and everything that had been done, while it made sense logically at the time, it was such that there was just no way that it was going to sell. And I just use this as an example that, you know, sometimes you will have that. But really, at the end of the day, the big thing is, you know, that this is why obviously the earlier you engage with somebody, the better, because some of these are going to take time to fix.

Dan: Yeah, absolutely, that makes a lot of sense. And then, you know, we've seen a real kind of storm of interested parties in acquisitions and buying businesses. You mentioned the amount of businesses that are gonna be sold. A lot of that is because of the baby boomer dynamic in America, but can you talk a little bit about, you know, from a buyer's perspective what typically marries up with the seller appropriately, right?

Dan: We've obviously you know, you've seen private equity get into all these different types of businesses, including smaller, more mainstream businesses than maybe they had been in the past. So talk a little bit about that buyer-seller relationship and kind of figuring out where the right marriage is.

Evan: Well, and again, this is why having a good advisor is crucial. Really, you have multiple types of buyers, and understanding what they look like will help you a bit. You have strategic buyers who, you know, they might be trying to buy a complementary product or like, say, an HVAC company. What they're going to do is they might just try to buy multiple other companies and just, you know, consolidate. So you have a strategic buyer out there.

Evan: You have what we label financial buyers, which are private equity primarily. They'll come in, they'll buy a business, they'll essentially do what—flip the business basically. And then obviously, you'll have, you know, family offices, which really are kind of like their own unique niche. But here's where it's very important if you're selling and the buyer-seller relationship and why it's very important that you don't try and do it yourself.

Evan: These buyers are professional buyers. I was doing some research, and the private equity firm your typical private equity firm before making an offer on a business for buying it, has reviewed 80 other types of offers. They're very thorough. And quite frankly, one important thing that also should be out there for your listeners are the unsolicited PE firm offers.

Evan: Somebody comes in, they say, you know, hey, we'd like to make an offer for this amount. And I remember a story about somebody receiving an offer of $52 million for their business. They thought, this is great. And they went and talked with their accountant who said, you know, it's a good offer, but I don't know if it's a fair offer. Let me put it out to my network. And lo and behold, actually that business was worth 70 million.

Evan: So I use that illustration, I use all this to say, you know, beware seller beware. You're going up against people who are professionals and the dynamic is such that you need to get the right advisors to help even the playing field.

Dan: Yeah, that makes a lot of sense. And that’s a good segue to my next question, which is: how do you think about business valuation? How should a business owner think about business valuation? And then what sort of trends have you seen in the last year or so around business values in maybe various industries?

Evan: Well, when it comes to business valuations, there are really two important things to remember. Number one, I think for business owners, getting a business valuation that is going to be really helpful for managing expectations. Just so that way you know, okay, this is around what I can expect.

Evan: On the flip side, when it comes to the business valuation, it's realizing that there's a difference between what the business is valued at and what, you know, the buyers are going to be willing to pay for. So that aspect of it and that's why, I mean, the M&A firm I work with on multiple things, you know, when they try to figure out what the value is, their approach is they'll send it out to buyers, asking, you know, “Hey, we have this such-and-such business in the Southeast. How much is it worth?”

Evan: So that's when it comes to valuation, obviously it's important to get them with some periodic frequency just because there's a lot of good benchmark information. But just understanding how they fit in; it's not like, okay, your business is valued at 50 million, therefore you should get 50 million for it.

Evan: The other thing that I wanted to add in addition to the subject of business valuation is with trends. This is a key thing: earn-outs are becoming more and more common. I forget what the percentage is, but there has been a sizable jump in the last if I remember the research about six years. I can't remember what percentage of deals, but they're becoming more and more frequent.

Evan: And a lot of it comes down to buyers they're just looking at the business and going, okay, yeah, we agree that it's worth this, but, you know, we're just not feeling comfortable, you know, going up to here. So if it performs at such-and-such a level, then, you know, we'll give you an earn-out. So the earn-outs have become much more common. And again, that's just because there's some deeper due diligence and there's some concerns about the fact that the business may not be actually worth the amount that the seller wants for it. And that's kind of where that hashes out.

Dan: Yeah, that makes a lot of sense. I mean, it's a de-risking mechanism for sure. Explain to our audience how a typical earn-out might look like, how would that be structured with respect to the overall deal? And then, what does the owner need to do in order to maximize that earn-out?

Evan: Gotcha. Well, really, let's say I'll just use a straight example. Let's say that you are selling a landscape company for 10 million. And, you know, we'll look at it and we'll say, you know, this company, it's great, but, you know, what we're going to do is instead of giving you 10 million upfront, we'll give you 7 million upfront. And over the course of the next three years, should it perform basically as expected, you can get a million per year over the next three years.

Evan: Now, obviously if it performs well in year one, you'll get it. And, you know, if it continues to perform in years two and three, you'll get it. But as is the case with some of these, okay, well, it falls short of expectations and as a result you don't get it.

Evan: Now, your question to answer the question about earn-out. Ideally, this is where getting your business optimized, operational and getting absolutely everything in order that will come in handy because if you have it well built so that way it's still humming after you left, it will continue to be very productive. Ideally, you know, if you're able to get it optimized and completely ready, you may not even need the earn-out because there's going to be no argument over whether or not it's ready. That's really better preparation is going to be what's going to help you maximize your earnings.

Dan: So I'm hearing kind of a key theme here, which is, you know, preparing the business to be able to run without such a reliance on the owner, right? That seems to be a key theme for the sustainability of the business and ultimately the value of it. What do you do and what do other advisors do to prepare a business owner to make what they've built less reliant on them?

Evan: That is a very good question. What I would do right at the beginning of my engagement is, in addition to a business and a cultural assessment, I'll ask them to fill out and I'll also look at the organizational chart. What we'll get started, once I get all that information together, is like, okay, not only do I know what we need to do, but I know how the leadership team needs to look.

Evan: Obviously the business owner well, they're probably functioning as CEO, possibly as CFO, and, you know, who knows, maybe several other roles. Well, let's find out in that business who we can elevate to CEO. And then, okay, if we have the talent, let's take somebody who might be doing the current bookkeeper work, get them in a controller type of role to get that position filled up, then promote them up to CFO. If there's somebody who would be a great COO, we could fill them in.

Evan: But by getting that leadership team and all of those responsibilities the owner used to have completely spread out, and then once that team is assembled, we start going to work getting everything thoroughly documented make sure all processes, policies and procedures are clearly laid out. If there's not a budget development process, get that instituted, make sure that there are proper controls in place.

Evan: In other words, start with the leadership team, get the right people, then build everything out so that way, you know, we have what I like to call the 90-day test. Can you walk away from the business for 90 days and it continue to function? If the answer is yes, you're ready to sell. If the answer is you can't be away for 90 minutes, we’ve got some problems.

Evan: So that really is the way that I would approach it. And I know there might be some other people who would approach it differently, but that is the methodology that I use to get it ready for sale.

Dan: Yeah, makes a lot of sense. All right, last question before we transition and this is where my team comes in, but I want to hear from your perspective. What advice do you maybe give the actual owner on sort of their life post-business, right? How do you make sure that they've got all their ducks in a row from a personal perspective, whether it be financially, family, how they're gonna spend their time, etc., etc.?

Dan: Because I'm sure, you know, most of the entrepreneurs that you deal with have spent a good portion of their life building this business, and it's a key component to what they've been as a person. So how do you kind of help them on the personal side of life after the sale?

Evan: That is a great question and that is the reason why I absolutely love working with wealth managers in this process. Because, you know, really just getting them to think, okay, you've been spending 60–70 hours a week building this business what are you going to do?

Evan: And I remember, I think it was last year, I had a conversation with a wealth manager. In fact, I even I think I may even have shared this story earlier today with somebody. But, you know, they had a business owner client who was getting ready to exit. And they asked, okay, once the sale goes through, what are you going to do? And it's like, okay, I'm planning to move to Colorado, specifically in the suburbs of Denver, and, you know, just spend time with friends and family.

Evan: Great. What are you going to do in Denver? And, you know, we look at this and it's the type of thing you might be thinking, well, I'm going to move to Denver and, you know, get a house there. But well, no, seriously. You've been spending 60–70 hours in this business. Even in Denver, what are you going to do?

Evan: You know, there’s I mean, some people, maybe it's travel the world. I know Vistage chairs you know, that would be something that could be phenomenal. I mean, if you've spent 40 years building a business, you could be a tremendous mentor to somebody.

Evan: But really, to kind of circle back to the question, it's just a matter of thinking, okay, you've got to have something that you can really put yourself pour your life into. Something that you can say, yeah, I feel like I get significance and meaning out of doing this.

Dan: Well said, and I think that's so, so important. You know, a lot of times I'm helping people figure out whether they be employees or they be business owners—figuring out sort of what they're gonna do post-work. Figuring out the personal side of that, to your point, sometimes people take that for granted, but it's so important to align the business strategy with your personal strategy and make sure that you've got things working hand in hand so that you can optimize what you're trying to do with the rest of your life, which that's why we do all of this, right? So great points there.

Dan: All right, we're gonna shift gears a little bit. You are officially entering the lightning round. All right, so here's the deal with the lightning round. We're gonna give you a series of questions. Just give us the first answer that comes to your mind. Could be a one-word answer, could be a long, drawn-out thought just whatever comes to your mind. You ready?

Evan: Okay. I think so, we'll see.

Dan: Get to know you a little bit better. One meal for the rest of your life what is it? One meal, you have one meal for the rest of your life, what is it gonna be?

Evan: One meal? Absolutely the Supreme breakfast burrito.

Dan: Supreme breakfast burrito, I like that. I hadn't gotten that answer before. That's a good one. I like it, I like it. What's one tool or technology could be hardware, software, it doesn't matter other than your phone or your computer that you can't live without?

Evan: I think this is outside of the box but kind of right up next to it. I'm going to go with my TV.

Dan: All right, that sounds good, that works, that works. Do you have a favorite quote or phrase about business or success?

Evan: Well, it's funny because I'm actually looking on the wall and I have this quote by Kevin O'Leary: “Profit is the loudest applause your business will ever get.”

Dan: That’s a good one. Mr. Wonderful, I like it. Do you have a favorite book about business or success?

Evan: Wow, that is a really good question. That is a very good question. I know that it's not about business, but I actually think I read, it was actually during the pandemic, the biography of Gary Bettman, who is the NHL commissioner. Just him taking a league that made 400 million annually into, I think, six billion now in just 30 years, and just what he did. I'd go with that.

Dan: I like it, that's a good one, very interesting. What's one bucket list item you've already accomplished?

Evan: Going to Switzerland and getting a chance to hike up to the base camp of the Matterhorn in Zermatt.

Dan: Very cool, very cool. How long ago did you do that? Tell us a little bit about what that experience was like.

Evan: It was a little it was. Okay, I'm gonna say it's an undisclosed amount of time, but just because I'm looking at the calendar and realize it couldn't have been that long ago. It took about nine hours to get up and back, and I was just so thoroughly exhausted. But the views were spectacular and just the incredible scenery.

Evan: And to kind of cap it off, that night there was this huge thunderstorm that went through and the next day there had not been any snow on the Matterhorn. It was completely covered in snow. So just thinking we left in the nick of time.

Dan: Wow, very cool. Good for you. Good for you. All right, last one: if you could give one piece of advice to your younger self, what would it be?

Evan: No matter how difficult things might seem to get, keep going. I think it was Adam Rose who was once interviewed and just noted that basically the difference between those who succeed and those who fail is those who succeed didn't stop. And it's that simple.

Dan: It's such good advice. It's so true of really anything in life if you think about it. And you know, sometimes in the moment it may not be that clear, but you hear that advice over and over again you know, “I wish I had just stuck to it,” or those that really made it, they just stuck to it. So that's really good and really simple advice, but so pronounced.

Dan: All right, and then finally, if our listeners wanna connect with you, collaborate with you, follow you, what's the best way to do that or reach you?

Evan: Well, I'm on LinkedIn. My profile is Evan B. Duke. And then my website is EvanDuke.com. Really, either of those—I mean, I'm on LinkedIn regularly. Of course, my website, you know, I have an opportunity I have a booking page as well as a button for you to call me. But those will be the two most effective ways to reach out and talk.

Dan: Yeah, I love following your stuff on LinkedIn. I think you've got some great content, so I urge any of our listeners to follow you, especially those that might be entrepreneurs, because Evan puts out a lot of really good insights there. So Evan, thanks so much for bringing your insights to Making Sense of Your Money podcast. Appreciate having you today.

Evan: Yeah, thank you. Thank you for having me and I hope you and your listeners have a great rest of the day and stay warm the rest of this year.

Dan: Yeah, we will, we will. We just got through a storm. Evan's down in South Carolina. I'm up here in Connecticut and surprisingly it’s very rare to say that but we got very similar weather patterns. It's kinda happening that way across the country right now, so it's an interesting time.

Dan: That's it for the episode. As always, you can find the podcast along with our newsletter and our YouTube channel all for free at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life. Cheers.

• Business Exit Planning: Preparing a company years in advance for a potential sale operationally, financially, and strategically.
• “Silver Tsunami” of Owners: The demographic wave of baby boomer business owners approaching retirement and exit.
• Customer Concentration Risk: Overreliance on a small number of customers (e.g., one client making up 80% of revenue).
• Key-Person Risk: When a business is overly dependent on the owner’s personal relationships, skills, or brand.
• Strategic vs. Financial Buyers: Strategic industry players seeking synergies, financial, investors (e.g., private equity) focused on ROI and future sale.
• Earn-Outs: Deal terms that pay a portion of the purchase price later, contingent on performance.
• Business Valuation: Formal estimate of enterprise value, useful for expectations but not the same as a final sale price.
• 90-Day Test: Evan’s simple readiness check: can the owner be gone for 90 days while the business runs effectively?
• Post-Exit Life Planning: Designing how you’ll use time, energy, and capital after a sale (travel, mentoring, community work, new ventures, etc.).

• Making Sense of Your Money – Podcast & Newsletter Hub
• Tailored Wealth – Work with Dan and the team
• Exit Planning & Executive Wealth Resources
• Contact Tailored Wealth

If you’re a founder or executive thinking about an exit in the next decade, consider:

• Clarify your 10-year picture: Write down what “life goes perfectly” looks like for your work, family, health, and impact.
• Assess business readiness: Look honestly at customer concentration, leadership depth, and how dependent the company is on you.
• Get a valuation & reality check: Use a business valuation and advisor input to set expectations and identify gaps.
• Build your leadership bench: Start grooming internal leaders or recruiting key roles so the business can pass the 90 day test.
• Talk to a wealth planner: Coordinate the business exit with your personal tax, cash flow, and investment plan.
• Map your post-exit life: Sketch out concrete plans for how you’ll spend your time and energy after a sale so the transition feels intentional, not empty.

A thoughtful, early-start exit plan can turn the sale of your business from a one-time transaction into a launchpad for the next chapter of your life.