Answer Box (TL;DR)
In this episode, Dan Pascone sits down with James Gorzynski, CEO and Managing Partner of Certified Exit Planners, to unpack what “strategic exit planning” really means for business owners. Instead of treating exit planning as a last-minute scramble when you’re ready to retire, James frames it as business strategy: aligning your personal goals, your financial plan, and your company’s value so you can create predictable outcomes whether your exit is 2, 5, or 20 years away.
You’ll hear how to think about the “three-legged stool” of exit planning (personal, business, and financial), what actually drives valuation and deal multiples, why owner-dependence can quietly crush value, and how recurring revenue, systems, SOPs, and strong people can radically increase what your company is worth. They also explore the mindset shifts needed for owners—especially baby boomers—to delegate, build structure, and design a work-optional or hybrid-retirement lifestyle instead of burning out inside a business that can’t run without them.
Key Takeaways
- Exit planning = business strategy with the end in mind. It’s not just about selling; it’s about aligning your personal goals, financial needs, and business performance so that whenever you choose to exit, you can do it on your terms with fewer surprises.
- The “three-legged stool” must be balanced. Effective exit planning aligns (1) your personal readiness, (2) your financial readiness, and (3) the actual business value and structure. Remove or ignore one leg, and the whole plan can collapse.
- Start earlier than you think. The best time to begin exit planning is years in advance. Owners 2–5 years from a potential exit should be engaging more deeply; those 5–20 years out should at least be educating themselves and making strategy tweaks now.
- Cash flow and multiples drive value. For most sub-$50M companies, valuations are based on a multiple of free cash flow (SDE/EBITDA). Typical deals might trade in the ~2x–4x range, but structure, recurring revenue, and reduced owner dependence can push multiples much higher.
- Owner dependence is a value killer. When the owner is the rainmaker, ops manager, and key relationship-holder, buyers see risk and compress the multiple. Building systems, delegating, and developing leaders can significantly increase value and reduce day-to-day stress.
- Recurring and predictable revenue is gold. Companies with strong recurring revenue (e.g., SaaS, contracts, subscription-like models) can trade at dramatically higher multiples than project-based or “eat-what-you-kill” models, sometimes 10x or more compared to low-multiple peers.
- People and culture are where most value lives. Roughly 80–90% of many owners’ net worth is tied up in their business, and 80% of that business value is usually tied to people. Investing in team, culture, SOPs, and leadership is central to a successful exit and transition.
- Clarity and organization unlock momentum. Many owners carry a “swirl” of ideas, worries, and to-dos in their heads. Exit planning helps get that onto paper, prioritize high-ROI moves, and create a clear roadmap that can be executed and refined over time.
Key Moments
- [00:26] – Dan introduces Episode 32 and frames the conversation around strategic exit planning and business owners looking to unlock the value they’ve built.
- [01:24] – James explains what exit planning really is—business strategy that aligns financial, business, and personal “legs of the stool” to create predictable results.
- [02:54] – James shares his background: accounting, data analytics, fractional CFO work, attempting to buy businesses, ultimately starting and selling his own company, and discovering the exit planning gap.
- [04:44] – Who James serves: culturally aligned owners of $2–$30M revenue businesses across trades, home services, franchises, and increasingly medical/healthcare, with a focus on values and fit.
- [06:03] – When to start exit planning: why the best time is “yesterday,” and how timelines differ for owners 2–5 years out versus 5–20 years out.
- [08:15] – The process: valuation ranges, benchmarking, discovery, SWOT analysis, prioritizing low-hanging fruit, and implementing high-ROI improvements before going to market.
- [11:00] – What drives value: cash flow and multiples, how most sub-$50M deals are priced, and why owner dependence and structure dramatically impact the multiple.
- [14:28] – Recurring revenue vs. project-based models: why SaaS- and contract-heavy businesses can trade at 10x+ while owner-dependent, non-recurring businesses may see 1–2x.
- [16:59] – The people factor: why 80–90% of many owners’ wealth is in the business, and ~80% of that value is tied to people and culture.
- [18:10] – Reducing owner dependence: CRMs, SOPs, sales playbooks, delegation frameworks, and specialized staffing as tools to build structure and value.
- [20:35] – When better systems make owners want to keep the business: how putting structure and people in place can create “mailbox money” and hybrid-retirement options.
- [21:57] – Dan introduces the concept of hybrid retirement and how flexible work and purpose can be built into exit and life design.
- [24:05] – Common challenges at the start of an engagement: intangible concepts, cluttered minds, lack of clarity on options, and how the first 30–90 days create momentum.
- [26:26] – Lightning round: coffee, Italian pizza, multiple screens, “operate with the end in mind,” favorite business books, personal productivity hacks, travel goals, and the importance of networking with intention.
Episode Summary
Episode 32 of the Making Sense of Your Money podcast features James Gorzynski, CEO and Managing Partner of Certified Exit Planners, in a conversation focused on strategic exit planning for business owners. Host Dan Pascone opens by highlighting how many owners think about exit planning only when they’re already at the doorstep of retirement—and how that mindset can leave a lot of money and options on the table.
James explains that exit planning is really just business strategy with the end in mind. Drawing from the Exit Planning Institute (EPI) framework, he describes the “three-legged stool” of a successful exit: personal readiness, financial readiness, and business readiness. If any one of those legs is missing or misaligned, the owner’s plan can topple. His work involves helping owners align those three dimensions so their eventual exit—whether in 2 years or 15—is as intentional and predictable as possible, rather than reactive.
James shares his journey from data analytics and accounting into fractional CFO work, then into small business ownership himself. He evaluated hundreds of acquisition opportunities, started and eventually sold his own business, and realized how many owners lack real support and structure when it comes to preparing for a transition. With both sides of his family rooted in small business ownership, he felt drawn to a career helping owners make better long-term decisions and build an informal “advisory board” of professionals—financial advisors, CPAs, M&A attorneys, coaches—through the lens of operating with the end in mind.
The heart of the conversation dives into valuation and what actually drives the value of a business. For most sub-$50M companies, James notes, valuations are based on a multiple of free cash flow—SDE, EBITDA, or similar—usually in the 2x–4x range. But that’s just the starting point. Owner dependence, structure, recurring revenue, and the quality of the team can dramatically change the multiple. If the owner is the chief rainmaker and daily operator, the multiple compresses. If the business has strong systems, SOPs, delegated leadership, and predictable recurring revenue streams, the multiple can jump—sometimes into double digits for the right model.
James and Dan explore the difference between project-based or “eat what you kill” revenue and recurring, contracted revenue. Using examples like landscaping and SaaS, James explains how two businesses with the same cash flow can have radically different valuations: an owner-dependent, project-based shop might trade at 1x–2x, while a recurring, contract-heavy business might attract 10x–20x, depending on quality and predictability. That gap represents millions of dollars in potential value and is exactly why owners should be thinking about exit planning years in advance, not months.
They also discuss the people side of the equation. James notes that 80–90% of many owners’ net worth is tied up in their business, and roughly 80% of that business value is tied up in people and culture. Investing in systems like CRMs, clear sales playbooks, SOPs, and specialized staffing can reduce owner dependence, increase team engagement, and drive both cash flow and multiples higher. In some cases, the business becomes so enjoyable and self-sustaining that owners decide to keep it and enjoy “mailbox money” or hybrid-retirement lifestyles instead of selling immediately.
Dan connects this to a theme he calls “hybrid retirement”—designing work and life so owners can keep doing meaningful, purposeful work with more flexibility and less grind. The goal isn’t always to sell and walk away; sometimes it’s to reshape work so owners can travel more, spend time with family, or pursue other interests while the business continues to run with a strong team and structure.
Finally, James shares common challenges he sees at the start of an engagement: owners often have a swirling mix of questions, fears, ideas, and obligations in their heads, but little organized clarity about their options or priorities. The early phases of exit planning focus on education, discovery, assessment, and getting everything onto paper—valuations, SWOT analysis, priorities, and a roadmap. Within 30–90 days, that process typically creates excitement and momentum as owners see a path emerge that aligns their business, finances, and life goals. The episode closes with a lightning round where James shares his love of Italian pizza, multi-monitor setups, EOS/Traction, quarterly travel goals, and the transformative power of networking with intention.
Transcript
Lightly edited for clarity and flow.
Narrator: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.
Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.
Dan: Welcome to episode number 32 of the Making Sense of Your Money podcast. I’m your host, Dan Pascone. I’m the founder and CEO of Tailored Wealth, and each episode features a trusted voice in the financial world, bringing their expertise to help high achievers to confidently make sense of their money.
Dan: Today, I’m excited to introduce a special guest. We’ve got with us James Gorzynski, who is the CEO and Managing Partner of Certified Exit Planners. I’m pretty excited about this discussion. James is a real expert and specialist on a topic that I’ve written a little bit about lately, and that is strategically exiting your business. So, James, thanks so much for joining us on the Making Sense of Your Money podcast. Pumped to have you today, brother.
James: Pleasure to be here.
Dan: Good, man. Good. So, we’ve got a lot to cover, and I know your expertise is going to be super valuable to our audience. So, let’s jump right in. Give us a quick like 90-second overview of what you do, how you help your clients, and then maybe a little bit of a backstory of how you got into it.
James: Yeah, absolutely. So, the idea of exit planning is basically business strategy. I like to mention that first and foremost, because a lot of folks hear the term “exit” and they immediately think that they’re being pushed towards the exit. Well, they are indirectly, but not necessarily right now.
James: A lot of the clients that we help are two to ten years out from an exit, but in reality the concepts and the strategies can be used with anyone at any phase of their business. We really strive to help folks align the three legs of the stool with regard to the CEPA—Certified Exit Planning Advisor—credential through the EPI, Exit Planning Institute.
James: The three legs of the stool are: the financial leg—how is their financial performance and plan; the business leg—how is the business performing; and then finally the personal leg. The idea is, if you have a three-legged stool and you take one leg away, it falls over. So exit planning uses business strategy to align all three of those legs of the stool to accomplish a cohesive and predictable result for a business owner. We help develop those plans and strategies, implement them, and when the time comes, we help broker the deals as well.
Dan: Love that. A lot of stuff I want to unpack there. That was a great summary. So let me ask you this: first off, how did you get into this field? What made business strategy and exit planning something that you were attracted to? And then what prompted you to go look at the CEPA designation?
James: Great question. I originally came from data analytics from quite a while ago, and I had a degree in accounting. That background was helpful, but ultimately I kind of moved into more of a fractional CFO role over time, working with smaller and smaller business owners. Most of them were legacy businesses run by a few folks, very family-focused.
James: I decided that I wanted to partner up with someone and grow a business, so I tried to develop a partnership with a few different folks. A few of them did not work out. Essentially I decided I was going to buy or start my own business. I evaluated several hundred businesses, made a few offers that fell through, and during due diligence I saw some red flags. It just didn’t work out.
James: At that point, I ended up starting a business. I ultimately sold it a few years ago, went through a successful exit myself, and realized that there are a lot of folks that aren’t getting the necessary support they need. My family on both sides—my side and my in-laws—are all small business owners. So at that point it kind of clicked. I wanted to help people make the best possible decisions and really help be part of their fractional advisory board.
James: That means working with financial advisors, CPAs, M&A attorneys, business coaches, etc., through the lens of exiting and operating with the end in mind. It essentially fell into place, and I feel very fulfilled now in my role. It was a long journey, but it was worth it.
Dan: Good for you. Good for you. Sounds like small business ownership and leadership is sort of in your blood, so to speak. That’s a great backstory.
Dan: All right, so let’s talk about what your specific clients look like. Obviously, you’re dealing with business owners, right? But what types of businesses are you typically working with? Let’s start there and then we’ll talk a little bit about what your process looks like.
James: Wonderful. Most of our clients, I view them more from a cultural perspective first. A lot of folks go into niche industries and I’m kind of falling into that same path long term. For example, we work with a lot of trade service businesses, home services, franchises, as well as dry cleaning, laundromats, landscaping, HVAC, roofing, plumbing, all that kind of stuff.
James: However, we are technically agnostic. It really starts with a discovery phase: do our cultures and ethics align? For example, we had a client that we actually had to step away from a few months ago. That was a tough decision—I never like to “give up,” so to speak—but their culture and ethics were showing their true colors after a few months working together, and it just wasn’t a fit.
James: So that’s first and foremost. The second piece is that we are working more and more with some of those industries I mentioned, and that’s also where I came from. Recently we’ve been working with more medical and healthcare-based companies as well. From a revenue perspective, they’re generally between two and thirty million in revenue. We really help with the growth phase on the $2–$10 million companies, and we help a lot more with exit strategies with some of the larger companies, just to give you an idea there as well.
Dan: Awesome. Very cool. All right, so when is the right time for a business to engage with an exit plan? You think about exit and, to your point, you think, “Hey, I’m on the doorstep of retirement. I want to go figure out how to sell my business. I want to make sure it’s optimized from a financial perspective, and I want to figure out the most tax-efficient way to go about this.”
Dan: That’s a lot of the work that we do with business owners, frankly. But when is the right time to connect with someone like you, that’s going to help make those three legs of the stool stand up, if you will?
James: I would say yesterday.
Dan: I like that. By the way, when somebody asks me when they need a financial plan, that’s what I usually say—yesterday. So I’ve got the same answer for you, brother. Go ahead, keep going.
James: The reality is that you can’t get back time. The most successful exit plans are, by definition, a plan. You can’t formulate and execute a real plan if you don’t have enough time.
James: My advice is to look at your exit timeline. Start with your exit timeline: what does it look like? Understand and educate yourself first and foremost. Talk to an exit planner as soon as possible just to get educational resources. That doesn’t necessarily mean a formal engagement right now. It might mean, “I need to understand more of what this really is and how it can add value to my family, my business, my employees.” That’s what helps frame some of the decisions.
James: That’s what’s really cool about exit planning: it starts to help business owners rethink how they operate. Thinking about operating with the end in mind, you start making decisions with the exit plan in mind, and it can really shape better results. So my biggest piece of advice is get information and resources now. Then when it makes sense, pick up the cadence—start working more on the exit plan and maybe formally engage a few years down the road.
James: If you’re in that two- to five-year window, I would say “soon.” If you’re in that five- to twenty-year window, start with education and understanding how it works.
Dan: So let’s say you’re in that two- to five-year window. Let’s talk about the folks that are a little bit closer to this—whether it be they’re ready to retire, or maybe they’ve just built up a business that’s got some value and they want to realize it and take some of that value and turn it into personal wealth. We see that all the time with business owner clients we work with.
Dan: Tell us a little bit about the process. What goes into getting a business ready to effectively exit?
James: Great question. There are a lot of variables, and that’s really where we help co-pilot the process. From a high-level perspective, we start with a foundation: where are you today?
James: First, we look at what the business is likely worth. We go through a range of value, comparing and benchmarking against similarly sized businesses as well as similar industries. We’re leveraging prior sales—just like comping a house, for example, except business valuation is a little more art than science at this level. That’s the first phase.
James: The next phase is a discovery phase, where we learn a lot more about the culture, the people, and the “nuts and bolts” of the business. We assess strengths and weaknesses through something like a SWOT analysis—something people are probably familiar with.
James: Then we start working through a process where we provide the highest value for the lowest cost possible. What are the lowest-hanging fruit we can implement to impact the value of the business and income to the owner? Those are the two most important parts in any business owner’s world. They tend to focus more on the income part, but in reality the value can produce a much better result for their overall plan and help close their “wealth gap.”
James: We talk about the wealth gap: do they know what their number is—what they need to retire and do what they’re passionate about, whether that’s family, travel, etc.? From there, we go into more execution mode, implementing and striving for certain KPIs, metrics, SOPs. We bring in other professionals for specialized needs.
James: Again, we’re thinking efficiency: the highest ROI for the dollar invested is how I like to operate. When we’re close to a sale—usually 12 months out—we also do pre-exit research, drumming up some pre-vetted buyers on the brokerage side. The team focuses on that simultaneously.
James: Then when we’re 12 months or less from a target exit, we spin up the business for sale: market it, talk to well-qualified buyers, and start taking letters of intent. We review multiple offers and hopefully take one to the finish line.
James: We don’t stop there. After the transition, we’re checking in, making sure the transition plan’s going well, post-life is great, and we actually have coaches who help with retirement as well. We try to add value the whole way through the process.
Dan: Very cool. Very cool. Very comprehensive.
Dan: You talked a little bit about value there, which I know is probably a hot button for any of our business owners listening. What typically goes into the value of a business that’s looking to be sold? And then what have you seen as far as recent trends—maybe in different industries? Obviously valuations are always on the move based on the marketplace, and you mentioned evaluating what similar businesses are trading for at any given time. Give us any intelligence you can share around general valuations and maybe trends in specific industries.
James: Great question, and it’s a multi-part answer. I’ll give you the best answer I can.
James: The two biggest factors in valuation are generally going to come back to cash flow. If you’re not investing your money to improve future cash flow and increase value, that’s a signal to rethink the strategy. That’s where exit-planning-oriented business strategy comes in.
James: With a market or income approach, the two most important components are free cash flow and the multiple. There are a lot of other valuation methodologies, but honestly most of them are pretty convoluted and more commonly used for $50M+ acquisitions. For anything under $50M, you’re probably going to focus on a multiple.
James: Most businesses are going to trade between roughly 2x and 4x of cash flow. So for example, if someone’s making $500K in profit—adjusted EBITDA, SDE, whatever term you want to use—and you multiply that by three, then conceptually your business is worth $1.5M. If it’s a more well-run business, maybe with stronger systems and less owner dependence, and it’s closer to a 4x, then now we’re talking about $2M, $2.5M, $3M or more, depending on specifics.
James: The other part is the structure or what some folks refer to as “hub and spoke.” If the owner is heavily involved and there’s an owner dependency in operations, you’re probably going to be closer to that 2x multiple—or even lower—because buyers see risk.
James: So maybe you’re still making the same $500K, but the business is only worth $1M now because the owner is the chief rainmaker—selling everything, running operations. If you can delegate and create better structure, the multiple goes up and the value goes up.
James: Regarding different industries, a lot of folks are moving more toward recurring revenue models. Easiest example: landscaping. If you’re doing project-based commercial work versus recurring residential or contract-based services, most buyers will pay more for predictable, recurring contracts. They’re going to pay a much higher multiple on those types of revenues and cash flows versus a purely project-based system.
James: So, that’s a strong shift. Another example: lower-labor-intensity companies. For example, self-serve laundromats or assets that are run with a more automated model. It’s more capex-heavy, but they can take accelerated depreciation on the front end and they don’t have to worry as much about labor. The business kind of runs itself. They’re just worried about repairs, maintenance, and maybe the real estate side of the transaction.
James: Those are a couple of examples. If you want specifics, I’m happy to provide them, but that gives you a flavor.
Dan: Yeah, you hit on a point that I’ve seen myself, both in my own business dealings and with a number of our clients. Let’s unpack this idea of the recurring revenue model versus the “eat what you kill” model.
Dan: I know that the recurring model trades at a much higher multiple. So let’s almost compare two sides of the spectrum. You’ve got a SaaS business that’s got contracts usually booked at two- to three-year terms, so they’ve got booked revenue for two to three years at a per-client level. Then you’ve got, on the other end of the spectrum, landscaping like you mentioned, where you’ve got to go out and lock down new clients every season or every year.
Dan: What can the difference in a multiple be between that really recurring, repeatable revenue model versus the one where you have great variance in any given market or cycle?
James: Using your examples, there’s a massive variance. Going back to our $500K cash flow example, I’ve seen some roofing or landscaping companies trade at 1x, 1.2x, 1.5x, 2x.
James: So in that case, you’re talking about a $500K business (or $750K, $1M depending on the exact multiple). Then I’ve seen recurring-revenue businesses trade at 10x, 15x, even 20x depending on how strong and predictable their contracts are.
James: Take that same $500K profit. With not much recurring revenue and high owner dependence, maybe the business is worth $500K or $1M. If it’s the opposite—high-quality recurring contracts, good structure, lower owner dependence—now we’re talking $5M, maybe more. That’s a 10-to-1 variance in value. It can vary quite a bit.
James: That’s what a lot of business owners can really impact over time. If they are at that three-, five-, or ten-year mark, they can start thinking strategically and position themselves for making a lot more money at the time of sale—while also being strategic about tax savings and setting themselves up for success.
James: Honestly, it’s also great for employees. If you delegate to a few key people, they feel a sense of ownership. That can really help culture. Another thing people don’t realize: roughly 80% of your wealth is usually in your business, and 80% of your business value is tied up in your people. The “80” number pops up a lot. Sometimes those numbers are even higher.
Dan: I’ve seen 90% in some studies.
James: Exactly. So why not focus on the most important parts: the business being 80–90% of your value, and then 80% of that value being people? Focus on the two things that can bear the most fruit.
Dan: Very cool. Very cool.
Dan: All right, great segue into my next question. Let’s talk about people for a second—the lifeblood of any business, I certainly believe. You mentioned owner dependency, and I’ve seen this be very typical. I’m sure you have, too. It’s a real pattern with baby-boomer-led and operated businesses.
Dan: For those listening, there is a massive shift happening right now. There are so many businesses run by baby boomers who are looking to retire. So whether you are one of those baby boomers and you’re looking to get your business sold effectively—this is a great conversation—or if you’re someone that wants to invest in a business, there’s a lot of opportunity out there right now. In fact, I’m looking at a couple myself.
Dan: With owner dependency, what do you and your team usually do and recommend for that baby-boomer business where, sure, they have good people working with them, but the day-to-day starts, stops, and ends with the owner? How do we get it so that there’s less reliance on that owner? Because, to your point, when you pluck that owner out, the value and day-to-day capability gets significantly reduced. Let’s talk about that process.
James: Great question. Every business is going to have a different starting point, so it’s highly customized. It depends on personality as well.
James: For example, if someone is open to tech and they see the value in it but don’t really understand it, that might be a good situation where you bring in some help—maybe AI tools, automations, and someone who can build procedures and add value quickly.
James: A CRM system is a great example. I can’t tell you how often I run into a company that doesn’t have a proper CRM—somewhere to track prospects, follow-ups, scheduling, and so on. I find it incredibly valuable; I did when I was running a business myself and still do to this day. Those are low-hanging fruit. They can add a lot of value very quickly, increase efficiency, and free up employees’ time to spend on revenue-generating items like sales.
James: The other big one is implementing SOPs and sales strategies. I find it interesting how many business owners know the value they provide—great customer reviews, strong reputation—but they can’t clearly describe their ideal customer profile. Going through a sales playbook exercise and understanding whether they’re spending time in the right areas to create predictable revenue with good ROI can be a game changer.
James: Empower some employees to do new things or bring ideas to the table. Use delegation wisely. Start with the lowest-risk items first. Don’t delegate the most important thing you do best or really enjoy. I encourage people to look at it with a quadrant system:
- Things you do really well and really enjoy—don’t touch those initially.
- Things you don’t do well and don’t like, and that are low risk—those are prime delegation candidates.
James: There are always folks we can bring in through specialized staffing agencies. For example, we have relationships with trade and service staffing firms—that’s all they do. They can help with office work or field work. We also have a specialized restaurant staffing recruiter. Restaurants are a tough business—I’ve been in that space before as well.
James: So we bring in additional help and resources to improve the company’s structure and take things off the owner’s plate.
James: What’s funny is that sometimes the business starts to run so well that the owner doesn’t want to sell. I view that as a success. There have been multiple times where a couple years go by, they’re collecting “mailbox money,” and even if they’re making a little less personally because they’ve invested in structure, the business is worth a lot more and they’re not touching day-to-day operations. Now they’re spending more time with family and friends. It’s an interesting and positive result for a lot of folks once they see the potential.
Dan: Yeah, you hit on a couple of things that I’m super passionate about.
Dan: Number one, I can see that happening—where you guys come in and help folks get focused on the things they love to do and are really good at. Maybe they were looking to sell because half their time was tied up in stuff they don’t enjoy.
Dan: Anyone out there running a business: the greatest advice I’d give is to spend as much time as possible doing the things you love and are really good at, and then find other talented people to do the rest. To your point, a lot of times people just look at that as a price tag. Those are investments. There are so many opportunities to get really good, often inexpensive staff today, as long as you spec it out and plan properly.
Dan: The second thing you touched on that I’m also passionate about is flexible work. I call it hybrid retirement. That’s a concept we write and talk about a lot with our clients. Essentially, whether you’re running your own business, volunteering, consulting—whatever—the idea is that as you progress in life and in your career, you get to a place where you can define what you want your work to look like.
Dan: Work can be super purposeful. Whether it’s your business or a nonprofit you volunteer at, it doesn’t matter. The idea is, as you’ve been in the workforce for a while, you can start to design your working hours to your liking. It can be very purposeful but with much more flexibility—more time traveling with your family, playing golf, whatever you like outside of work.
Dan: That’s a concept that, I’ll tell you, I’ve seen firsthand with our clients. It gets me jacked up talking about it because I’ve seen how much of a lifestyle shift it can be for people and how enjoyable it can be—not when you’re 80 and sitting on a beach, but when you’re still in your prime working years with more flexibility and enjoyment in your work.
James: Absolutely. I like what you touched on there. It’s not just about the third or fourth quarter of life. This happens a lot with folks in their 30s, 40s, 50s, 60s—the age doesn’t matter. It really comes back to their passion and what drives them.
James: The question is: how much can they relax and just do what they love? That’s the huge value and driving factor we see, and we really like to hone in on that.
Dan: Cool, man. All right, one more and then we’re going to shift gears.
Dan: What are the biggest challenges—probably some you’ve already hit on—that businesses and business owners typically face when you start your engagement with them?
James: Great question. The first thing is that it can be difficult to show exactly what we’re going to do. It’s more of a concept at the start. We often use visuals, graphics, and general frameworks. Some folks struggle a bit until we start the discovery and assessments. Then it clicks—the light bulb goes off.
James: That’s one of the things we’re really passionate about: talking about what’s hard to see at first. Once they’re in the program, they really see and understand the value. That’s very fulfilling—for us and for them.
James: I’d say the other big challenge is clarity. There’s a lot swirling in their heads—personal and business. We help them prioritize and organize those thoughts. That’s what we’re there for.
James: We bring in folks who can help with specialized needs for different parts of the business, different industries, different personalities. But the goal is to boil it down to their most ideal exit and then work toward that, massaging and evolving it over time.
James: I’d say getting everything out of their head and onto one piece of paper—figuratively—is the biggest struggle at first. That’s why there’s a lot of movement in the first 30–60–90 days. We have checkpoints along that path. After 90 days, there’s usually a lot of excitement and momentum.
James: So I’d say they’re often not sure of all the exit options, and there’s not a lot of clarity. That’s why I mentioned being a resource and support earlier. We view ourselves as a resource first, and then yes, we consult on specific scenarios. But we want to educate people first and really help guide them through the process.
Dan: Yeah, that’s great. I imagine that exercise creates a high degree of clarity, which is really important, especially when you’re starting an engagement. That makes a lot of sense, brother. Great stuff.
Dan: All right, we’re going to shift gears a little bit now. We’re going to get to know you a little bit more. So James, you are officially entering the lightning round. We never tell our guests about this ahead of time, so it’s meant to be super organic. All we ask here is that you share the first thought that comes to your head. Could be a one-word answer, could be a more drawn-out thought—anywhere in between. You ready?
James: Sure.
Dan: Let’s do it. All right. Coffee or tea?
James: Coffee.
Dan: One meal for the rest of your life—what is it?
James: Italian pizza.
Dan: Italian pizza, I love it. Do you have a favorite pizza spot?
James: I don’t know the name of it, I forget. It was in Italy.
Dan: It was in Italy—okay, good. You can’t go wrong with that. Remind the audience: where are you located, James?
James: Charlotte, North Carolina.
Dan: Charlotte, North Carolina, okay. Sounds good. We’re going to have to have you come up to Connecticut for some New Haven pizza at some point in time—we’ll do that.
Dan: What is one tool or piece of technology—hardware or software—other than your computer or your phone that you can’t live without?
James: Piece of technology…I would say, it sounds weird, but TVs or screens. It helps me visualize things quickly.
Dan: Screens. You’re a multiple-screen guy. Okay, that makes sense.
James: Yeah.
Dan: Me too. I’ve got three going right now, and we’re actually moving into a new office space—I might even add to that. So I’m with you on that one.
Dan: Do you have a favorite quote or phrase about business or success?
James: I use the phrase all the time, and it’s partially borrowed from Stephen Covey and Warren Buffett: “Operate with the end in mind.”
Dan: Love it. Big fan of both of them, so you can’t go wrong there. Do you have a favorite book on business or success?
James: I would say Walking to Destiny was great. Some of the EOS books—Traction was wonderful.
Dan: I’m a Traction guy. I’m with you on that one. In fact, I’ve read all the EOS books, and I would highly recommend anyone who’s even just leading a business unit to read them. Start with Traction, then How to Be a Great Boss, Entrepreneurial Leap—all great.
Dan: Do you have a personal hack that you can share with the group that you live by?
James: Personal hack: to retrain your thoughts. I tend to think of different things at different times, and the most accessible piece of technology I have is always my phone. So I have a task board on my phone. When I think of something—every time I have a conversation, after I hang up—I’ve trained my brain to ask, “Do I need to put that in my task board?” I know I’ll forget otherwise.
James: The other thing, from a physical perspective: I always put things at the front door if I need to take them somewhere. I’m going to trip over them if I don’t. It’s one of those simple hacks.
Dan: You and I use two of the same ones, man. I love it. So I go as far as using two different functions within my phone. I have Siri set reminders for me if there’s something that I want to do at a specific time, or I have an integration between Siri and Notion as the platform where we keep all of our intellectual property, notes, to-dos, and all that stuff.
Dan: I have a setting so I can just speak to my phone and it will send something to my to-do list. I love those. Those are great ones. And putting stuff at the front door is great too, because I used to always forget things I wanted to bring to work, and now if it’s at the front door, you can’t forget it.
Dan: What’s one bucket-list item that you’ve already accomplished?
James: I’ve already owned and sold a business.
Dan: Perfect. Love it. Congratulations on those.
Dan: What’s a financial milestone that you’re personally working towards?
James: I want to hit the financial freedom point where I can do a lot of the things I’m conveying to business owners. For example, I’ve set a goal to travel at least once a quarter to a place I’ve never been.
Dan: Love it. That’s awesome, man. Great goals to have, great things to plan for. We love seeing people do the things they really enjoy in life with their money.
Dan: Last one: if you could give one piece of advice to your younger self, what would it be?
James: Network. Network. Network. I think I spent a lot of time working very hard in specific jobs and for other folks, and I was in a very narrow hallway doing really wonderful things for a small subset of people. I got a lot of great feedback and mentoring, but the part that I did not do well when I was younger was networking.
James: I think I would have been exposed much faster to what I’m doing now and what I love to do if I had talked to more people—because I didn’t even know that M&A brokerage was a thing until well after I started this path.
James: So I would say: network. Talk to more people, learn what they do, spend time and listen. Listening is wonderful. Through observation and listening, you’ll learn so much about the world around you. And I think you’re more likely to end up doing business with people you love being around. So I’d add one more: say no if someone doesn’t fit your culture and your values.
Dan: That is such good advice. Everybody tells you to network, right? But for listeners out there, what I like that James said is: network with the intention to get to know other people, learn what they do, and listen.
Dan: That’s the effective way to network. There are so many people who are just networking for selfish reasons, but if you network with the intent to get to know others, you learn so much. Not every connection will be a home run for your career or business, but if you have enough of them, you’ll find ones that are. And you’ll always learn along the way. Every new person I speak to each week—and I have the luxury of speaking with a lot of new people—I learn something from them.
Dan: I love your thoughts on that. James, thanks so much for sharing your time and your insights with us today. That was a lot of fun.
Dan: That’s it for the episode. You can find our podcast along with our newsletter and our YouTube channel—all free—at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life.
Dan: James Gorzynski, thanks for joining us.
Frequently Asked Questions
What is “exit planning,” and how is it different from just selling my business?
Exit planning is the process of aligning your personal goals, your financial plan, and your company’s structure and value so that when you eventually transition—through a sale, succession, or even partial exit—you can do so on your terms. Selling is an event; exit planning is an ongoing strategy that influences how you run the business years before a transaction.
When should I start thinking about exit planning?
Earlier than you think. If you’re 2–5 years from a potential exit, you should be actively planning and implementing changes now. If you’re 5–20 years out, you should at least be educating yourself on the concepts, understanding what drives value and multiples, and making strategic moves (like building recurring revenue and reducing owner dependence) that will compound over time.
What types of businesses does James typically work with?
James and Certified Exit Planners work primarily with owner-operated businesses between roughly $2M and $30M in revenue. While they are technically industry-agnostic, they frequently work with trade and home services (HVAC, roofing, plumbing, landscaping), dry cleaning and laundromats, franchises, and increasingly medical and healthcare businesses. Cultural fit and alignment of values are top priorities.
How is the value of my business usually determined?
For most sub-$50M companies, valuations are based on a multiple of free cash flow—often SDE (seller’s discretionary earnings) or EBITDA. Typical deals might trade around 2x–4x, but that multiple is heavily influenced by structure, recurring revenue, owner dependence, team strength, and risk profile. Recurring, contract-based revenue and strong systems can push multiples much higher, while project-based and owner-dependent businesses tend to trade at lower multiples.
What is “owner dependence,” and why does it matter so much?
Owner dependence describes how much the business relies on the owner for sales, operations, key relationships, and decision-making. If the owner is the “hub,” buyers worry the business won’t perform once that person leaves, which compresses the multiple and reduces value. Reducing owner dependence—through systems, SOPs, delegation, a strong leadership team, and proper tooling like CRMs—can significantly increase both value and buyer interest.
How does recurring revenue affect my company’s valuation?
Recurring revenue—through contracts, subscriptions, retainers, or other predictable models—greatly increases the predictability of future cash flows. Buyers will often pay materially higher multiples for high-quality recurring revenue compared to one-off or project-based revenue. In some cases, two businesses with similar profit levels can have 5x–10x differences in valuation based largely on the quality and predictability of their revenue streams.
Is this episode personalized financial, tax, or legal advice?
No. The conversation is educational and discusses common patterns, strategies, and concepts in exit planning and business valuation. Your situation is unique, and exit decisions involve complex tax, legal, and financial considerations. Before making decisions about selling, restructuring, gifting, or transitioning your business, you should consult with your own qualified financial advisor, CPA, and attorney who understand your full situation.
Disclaimer
The information in this episode and on this page is for educational and informational purposes only and is not intended as individualized investment, tax, or legal advice. Business valuations, exit strategies, and tax outcomes depend on your specific facts and circumstances, and laws and market conditions may change over time.
All investing and business ownership involves risk, including the possible loss of principal. Before making decisions regarding the sale or transfer of a business, restructuring ownership, or implementing specific tax or estate strategies, you should consult with qualified professionals—such as a financial advisor, CPA, attorney, and other relevant specialists—who can review your complete financial picture and objectives.