Scaling With People
Tired of spinning your startup wheels but never gaining traction? Buckle up, founders and CEOs, because this podcast is your rocket fuel to profitability! Every week, we ignite explosive conversations with bold-faced founders, brainy experts, and even a few out-of-this-world vendors. Get ready to crack the code on growth, master employee engagement, and blast through your scaling goals. We’re talking real-world strategies, actionable tips, and perspectives that’ll make your business do a cosmic dance. So, strap in and prepare for lift-off!
Scaling With People
Sell Without Regret with Joseph LoPresti
What if your biggest win isn’t the highest revenue month but the day you walk away on your terms? We go straight at the myths around exit timing, value creation, and “someday” planning with succession expert and wealth strategist Joseph LoPresti, breaking down the moves that turn a chaotic founder led operation into a transferable, high multiple business. From defining your Freedom Point to engineering enterprise value that a buyer will pay for, this conversation trades vague platitudes for clear steps any owner can start today.
We start by reframing success: income feeds your lifestyle, but enterprise value funds your freedom. Joseph explains how earlier planning widens your options, why three to five years is a sweet spot, and how to assess where you stand against best in class multiples in your industry. We dig into the buyer’s lens—recurring revenue, documented processes, leadership beyond the founder, competitive advantage you can articulate—and why “growing the bottom line” isn’t enough if growth depends on you. You’ll hear practical ways to reduce owner dependency, build predictable cash flow, and protect the value you’ve already created.
Then we tackle the money mechanics that too many founders leave to the last minute. Pre sale tax planning, entity structure, trusts, and capital gains mitigation need runway to work. Joel maps a two track approach: on the business side, assess, protect, enhance, and harvest value; on the personal side, model lifetime cash flow, set your Freedom Point, align investments, reduce taxes, and design your legacy with proper asset protection. We also unpack the power of coordinated advisors over siloed advice, and close with a personal action plan that clarifies ideal buyers, your post close role, and how your team will be treated during the transition.
Ready to sell without regret and live with intention after the deal? Press play, grab the free e book at exitbydesignbook.com, and tell us what metric you’ll fix first. If the show helped you think bigger about your exit, subscribe, share it with a founder friend, and leave a quick review so more builders can find these strategies.
Welcome to Skilling with People, your weekly playbook for turning chaos into compounding growth. Each week we go under the hood with battle test experts in all areas of business, from marketing to sales, operation and finance and people, plus product and leadership to unpack the plays, numbers, and systems that turn chaos into compounding growth. Learn straight from founders and experts who've done it and continue to do it successfully. There's zero fluff, just moves that you can still immediately. This podcast is brought to you by Guide to HR, human expertise, AI-powered impact. Welcome everyone to today's Skilling with People podcast. I'm Gwynaver Curry, your host and founder and CEO to Guide to HR. All right, guys. What if your biggest business win is the day you walk out and walk away from it? On this episode of Skilling with People, we're flipping the script on exit strategy with Joe Lepressi, who's a succession expert, wealth strategist, and the guide founders call when they're finally ready to cash in without crashing out. We're diving into why someday isn't a strategy and how to boost your company's value before you list and how to hit your freedom point, that magical moment where your business serves your life, not the other way around. So let's jump in, everyone. Welcome, Joel Presti. I'm excited to have you on the call. Uh share a little bit about yourself to the audience.
SPEAKER_01:Yeah, well, thanks for having me, Guinevere. I um Joel Presti. Uh I run uh a ClearPoint Family Office, which is a fractional family office that works with business owners on coordinating their business planning with their personal wealth planning, uh making it into a unified approach that's centered around the life and legacy that they want to design.
SPEAKER_00:Awesome. Okay, so let's get into it. My first thought is okay, I'm maybe too new or just starting out, or maybe in the middle of what I'm trying to build. I don't need to listen to this guy. I'll come back to it later. But I'm curious, is that false? When should a founder start thinking about their exit?
SPEAKER_01:Well, so there's a time they should start thinking about it, and then there's a time when they when they tend to really start thinking about it. Um, I mean, to be a little self-serving, you start thinking about it when you start the business. If you if you design the business based around you what you want to ultimately achieve, you're more likely to achieve it. Um, so we're we're seeing more and more business owners, uh, particularly the you know in the millennial age group uh generation that are is thinking about exit planning earlier in their career, uh, compared to like the baby boomer generation, which really didn't think about it until they reach retirement age and now they have to you know kind of figure it all out. Uh but it it obviously the earlier you do it, the better off you're going to be because you have time to plan. Um, and it's not just about the exit, it's about establishing freedom. And um, a lot of that is centered around um, you know, having personal freedom, not just financial freedom, being able to, you know, live the life that you want, spend the time that you want to spend with the people you want to spend the time with, and not so much be tied down to a business that's all centered around you.
SPEAKER_00:Yeah, that makes sense. Okay, so start thinking about it because you can plan and then obviously through your building in years, months, years later, you can course correct and make sure you're staying to that plan.
SPEAKER_01:Yeah, exactly. Now, the reality is that you know, when you start a business, you're you're scrambling, you're trying to figure things out, you're putting processes in place, you're growing the business, you're developing, you know, you're you're selling, you're running, you're you're doing, you know, everything from A to Z. And it's hard, right? It's hard to find the time to do this type of planning. Um, so ideally, if you can be three to five years out from the ultimate end game, is a sufficient amount of time to do some of the things that we'll talk about during this meeting. Uh, but the earlier you start, the better off you're gonna be. You know, there's just a lot of tax planning you could do. There's uh a lot of um, you know, value enhancement that you could work on along the way. Uh, and again, some of that centers around um, you know, creating a business that uh takes you out of it so you could step away from the business for lengthy periods and it to it you know being successful and be able to run and function and grow without you being at this you know the the that hub of of the wheel.
SPEAKER_00:Yeah, that makes sense. So what's kind of the first thing, or maybe a couple first things that a founder should be thinking about in regards to let's say that three to five years out stage, right? Um, you know, okay, I'm I've been I'm thinking I want to exit in three to five years. What's kind of the first step or uh thought process that I should be going through uh to get myself started?
SPEAKER_01:So uh I would, you know, there's a few things. I think one thing that comes top to top of mind is uh determine your freedom point, and that's the amount of financial wealth that you need to do whatever you want, whenever you want, of course, within reason. But when you can live the life you want without worrying about money. Um, and that really, you know, you have to tie in uh business planning. So assessing the value of your business, knowing where the industry that you operate in, what the range of values tend to be, know, you know, do an assessment of your company to see where you would likely fall in that range. So you could know what areas you could work on to improve your your multiple, the uh, you know, the the multiple of cash flow that your business would likely sell for. Uh, and then how that ties into what you need with your life and your lifestyle, your goals and objectives, and and see where you're at. Uh, you know, sometimes business owners find it to be are very surprised that they see they're already at their freedom point and they didn't think they were. They start to think about their business a little bit differently, uh, make decisions differently, protecting the value of that business becomes more important at that point. But on the other hand, others you know need it to grow more, but at least you know where you're at, what that gap is, and then you can start working on ways to improve the value to help close that gap and reach the freedom point.
SPEAKER_00:That makes sense. Yeah, understanding that target and then start working towards it. So um, I know you're also an author. Tell us a little bit about your book and what it's about.
SPEAKER_01:Yeah, so the book is titled Exit by Design. And um it's about um coordinating the personal wealth planning with the business strategy to you know reach the freedom point, kind of the things that we're talking about here. Uh, it discusses different concepts that blend in the business strategy with personal planning and uh make sure that it's coordinated and unified behind the uh you know, the life that the business owner wants to ultimately achieve.
SPEAKER_00:Yeah. And so let's think about like, you know, you're wanting to improve your business value and the sell price. What are some of the critical metrics that a business owner should be looking at consistently and trying to improve over time for that specific person of sale, or excuse me, for that specific reason of selling?
SPEAKER_01:So we like to have business owners kind of shift their mindset from how they view their business today to what they should be, how they should be viewing their business. Most business owners look at their business of how much money it's making and can it, you know, provide the income that they need to, you know, to live. Uh, we want to shift their focus to maximizing the enterprise value of that business. Uh, because certainly, you know, having sufficient income to fund your lifestyle is important and it's and it's part of maximizing enterprise value. But what's really going to secure your freedom is that that enterprise value. So let's start to look at what is the value of the business from a buyer's perspective, from a third-party perspective, not the way that most owners tend to look at the business, but what's important to a buyer? Let's establish what that value is today. Then let's look at areas that they could improve on to make the business look more attractive to potential buyers. And that's going to increase their enterprise value. Then you could look at ways to grow the business. Um, and oftentimes, you know, just growing the bottom line isn't necessarily that attractive to a buyer, particularly if it's if it's um because the business owner themselves are the ones that are generating and driving that growth. Right. There's other things that a buyer is going to look at. You know, if they want to buy a job, then they buy a business that's dependent on the owner. If they want to buy a business that could make them money without them having to be, you know, where it begins and ends, they're going to look at your business a little differently.
SPEAKER_00:Yeah, that makes sense. And it is, it's a different lens that the owner that you need to put on one, you know, just growing your business versus the value at the sell price point.
SPEAKER_01:Absolutely. They there, there's, you know, they're different metrics, right? So owner dependency is one. You know, we look at things like recurring revenues on, you know, what how do your revenues come in? Buyers really value businesses that have recurring revenues where there's predictability of cash flows, as opposed to businesses that have to bring in, you know, new business every month or every year, and they're starting at zero. Um, so things like that. Um, what's your competitive advantage? Why do your customers do business with you over your competitors? And being able to articulate that to uh you know, to to buyers and just articulating that to your customers is is very important.
SPEAKER_00:Yeah, absolutely. I I see that a lot of times, and it's so interesting when you talk about is the owner the one bringing in the business and like you know, to change it a little bit. I see when founders are ready to step away or step into a different role that they're not the one leading the business. That culture shift that happens internally, it's the same thing because the employees brought on to the business are all being brought on because of the enthusiasm, the vision, the personality of the CEO. And then they leave and the employees are like, wait, who's this next person leading? Do I believe in them? Do I think they're gonna grow the business? And it's the same kind of concept. You know, if someone's gonna buy your business, they need to be able to know that it's gonna thrive when you're not in it anymore.
SPEAKER_01:Exactly. So there again, you know, there's there's different buyers of businesses, of course, but if you're selling to an individual who's going to be the owner and operator of the company, then you know, they're gonna look at, you know, they're gonna look at it as just replacing you, right? But if you're if you're selling to maybe an a um um uh a strategic buyer, somebody else in your industry that's consolidating businesses in your industry, they want to know that they could be maybe bring some of their processes into your business. And if you're removed from it, that they're going to be able to profit from it. Right. So, you know, they're not buying what you've built, they're buying what they could take from that point and grow it further and profit from it further. Most business owners look at it and say, hey, I've worked here 20 years, 30 years. You know, founding business owners, many of them, it's you know, it's their life and it's their baby and what they've built. And they feel like they should be compensated for what they've built. A buyer wants to look at it and say, How could I profit from it from this point forward? That's what I'm willing to pay for.
SPEAKER_00:Yeah, absolutely. I mean, just like anything, when you purchase something for an investment, you want ROI on it, you want a return on that investment. Yeah. So uh, you know, let's fast forward sweet, you know, time sell the business. I'm super happy about it. Uh, how do you navigate all the taxes? And probably a big question here, but what's like the first couple of things that a founder should be thinking about in regards to minimizing the tax liabilities before or during and after the sale of the business?
SPEAKER_01:Yeah, so there's there's so much to talk about there. That it's uh and it's very, you know, it's very different from specific case to specific case. Um, but generally speaking, uh when we look at proactive tax reduction planning, we're looking at it on the business level while it's operating. What are ways to reduce taxes from the business perspective, which oftentimes is just going to flow through to the personal, the business owner's personal tax return. But if there are ways that we could reduce what's flowing over to the business, to the owner's personal return, that's an effective uh tax reduction uh strategy. Then we want to look at uh how to reduce taxes one for the for the the uh the income that does flow over to the personal uh business personal tax return, of course. Um so we're also looking at ways to mitigate the gain, that the tax on the capital gain of the transaction itself. That's where pre-planning uh becomes very important. You can't do that. You know, when we if if people call us, say they want to sell their business in six months, how do I, how do I mitigate the tax on it? There are some options, but you're limited at that point. If you start that three to five years out, there may be entity structures that need to be set up, there may be specific trusts, there could be some estate and wealth transfer, you know, asset uh transfer that can be carried out to satisfy um, you know, wealth transfer goals and family goals, etc. Uh so the more time you have there, the better off you are. And then ultimately, business owners need to get cash flow after they sell the business to be able to live their life. Pre-planning could help make that tax-efficient cash flow. If you wait until the business is sold and say, okay, now we need to invest this money, how are we going to do it? You miss a lot of wealth-building opportunities as opposed to focusing on that in the pre-sale planning.
SPEAKER_00:Yeah. And do you also assist on that whole investment before and after the sale?
SPEAKER_01:Yeah. So our our approach is uh really helping a business owner run down, we call it running down two tracks, two simultaneous paths. One is the business planning, and that is where the focus there is maximizing the enterprise value. So we want to assess the value today. We want to look at the industry they operate in and what are the range of values, uh, showing where the best in class companies sell for, show them how to get to the best in class. Uh, then we want to protect that value, right? And in other words, they've built X amount of value in their business. Uh, what are your biggest dangers and threats? Let's mitigate that and make sure, for example, if you were to pass away, how is that wealth going to get transferred to your family or to partners or uh, you know, however, however you you want it to work, make sure that that's in place, buy sell agreements, things like that. Then we go on to enhancing value and developing a strategic plan on how to uh exponentially increase your business value. And again, it's all about what that enterprise value is. And then finally, how do you harvest the value? Prepare for the eventual exit with business and personal readiness planning and assisting and securing an ideal buyer or transitioning ownership if you're, you know, if you're transitioning to family or to management or employees, for example. So that's the business planning path. The personal wealth planning path starts with developing a lifetime cash flow plan. Um so we could base all decisions and maximize their wealth and net worth around the life that they want to live. Once we know what their goals and objectives are, we determine their freedom point, what they need the business to be worth, to be able to live the life that they want, of course, along with the other assets that maybe they've accumulated. We work on proactive tax reduction planning, like we discussed earlier, business reduction, personal reduction, capital gain tax reduction. We focus on investment consulting and uh aligning investment strategy with their objectives, preserving wealth through market downturns for financial assets, for example. And then finally, that legacy estate and wealth transfer planning, making sure everything's in alignment with what they ultimately want to achieve from a legacy standpoint, and personal asset protection to avoid them hitting that you know proverbial uh financial iceberg, you know, those catastrophic risks that could uh that that that could be uh um you know ruining in personal situations. So those are the the ultimate, you know, kind of running down the six or seven or eight different levels of planning that need to be done for a life cycle for a business owner.
SPEAKER_00:Yeah, that makes sense. It's a lot to think about for sure.
SPEAKER_01:It's a lot to think about. And business owners, that's not what they're strong at, right? And and I think if you ask a business owner today how they're getting their advice, they'll say, well, I have an accountant, I have a financial advisor, you know, maybe an attorney. Yeah, maybe an attorney, maybe some business consultants, but they're working with those advisors individually and they're getting siloed advice. What really where the rubber really hits the road for a business owner is coordinating the business strategy and the personal wealth planning and crossing over those professional silos to make sure that gaps aren't are aren't existing that expose dangers and that opportunities are being fully taken advantage of. Um so that's where I, you know, we believe a team planning approach, people that are sitting around a table talking about the client and what they're trying to achieve and what are potential solutions and the synergies that come with it is a step above working with individual advisors. And then the business owner having to try to coordinate it all themselves. And that's just not their strength and you know what they have experience in doing.
SPEAKER_00:Yeah, awesome. Well, so as we wrap up today, are there any last final thoughts or tips or tricks, tools that the bounders could be taking action on as they wrap up listening to this call?
SPEAKER_01:Yeah, so it's it's uh, you know, I would say developing a personal action plan is something that all business owners should do. And that's looking at you know the different areas of their business and and how what what how do they want it to unfold? What does the end game ultimately look like? Uh how will your business transition? Will you sell it to a third party? Will you will you transition it internally? How are you going to capitalize on that ultimate enterprise value? Uh, who are the ideal buyers? Um, you know, what what role will you have in the company after it's sold? Some people want to stay on, some people don't. Uh, how do you want your employees to be treated during during and after the transition? You can control all those things much better if it's part of the conversation, you know, well before that transaction as opposed to after the transaction. And then, really personally, what does their life look like? You know, business owners have a hard time just walking away from something they've built over many years. You know, what are you going to do Monday morning after the business is sold? And again, you can't just wait till it's over and and the transaction's done and then think about it. You really want to plan that out well ahead of time. So, all of those are things a part of a personal action plan that we we find helpful for a business owner to put put in place.
SPEAKER_00:I love it. Well, thank you, Joe. This has been very insightful. And for those listening, I hope you got some good tidbits and some thoughts of maybe reconsidering your exit strategy. And uh, Joe, how can they uh reach out to you if they want to learn more?
SPEAKER_01:Yeah, so there's a couple of ways. Uh, one for all of your listeners, we'll make a uh a complimentary copy of our book e version available uh on the book's website. That's exitbydesignbook.com. And uh if they wanted to uh have a conversation, um then they could contact me at ClearpointFamilyOffice.com.
SPEAKER_00:Awesome, great. Well, thank you. We love freebies. So uh you heard it here, freebie at exitbydesignbook.com. And uh Joe, it was great having you on the call. We appreciate your insight. And for the listeners, thanks so much for joining us. If you like the podcast, share it, put a comment out, like it, follow us, and we will see you on the next one. Take it easy, everyone. Bye. That's a wrap for today's episode of Scaling with People. If you got value from this conversation, do me a favor, share it with someone building something big. And hey, I'd love to hear your take. Drop a comment, shoot me a message, or start a conversation. And don't forget to subscribe so you never miss the bold, unfiltered strategies we drop every week. I'm Winnipeg Cruy, founder and CEO of Guide2HR, where we help high growth companies scale smart with people for strategies and AI powered systems that don't just keep up, they lead. If you're building fast and want your HR to move faster, head to guide2hr.com and let's talk. And remember, scale isn't just about speed, it's about people. Until next time, have a great one.
