564: Buying and Selling a Business or Practice

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For most high-income professionals, the path to financial success seems straightforward: work hard, earn a great income, save diligently, and invest wisely.

The problem is that even the highest-paying jobs have two significant limitations.

First, much of what you earn is exposed to taxation. While there are certainly strategies to reduce your tax burden, there is a reason many of the wealthiest people in the world own businesses rather than simply collect paychecks. Business ownership creates opportunities for tax efficiency that are often unavailable to employees.

Second, a job—even a very lucrative one—is generally not an asset you can sell. You may earn hundreds of thousands or even millions of dollars per year, but when you stop working, the income stops too.

A successful business, on the other hand, can generate ongoing cash flow while simultaneously building enterprise value. Over time, that value may become one of your most important assets and, ultimately, something you can sell for a substantial payout.

Now, this is not a call to quit your day job and become an entrepreneur overnight.

In fact, for many of us, the better question is whether there are opportunities to acquire an existing business rather than build one from scratch. Every day, thousands of profitable small and mid-sized businesses are owned by operators approaching retirement who may not have a succession plan. In many cases, these businesses can be acquired with financing, professional management, and a thoughtful growth strategy.

This week’s guest, Joe Prencipe, helps us understand exactly how that world works.

Joe is an attorney who specializes in business acquisitions, sales, and deal structuring. In this episode, we discuss what makes a business valuable, how buyers and sellers often leave money on the table through poor planning, and why deal structure, taxes, financing, and operational realities frequently matter far more than the headline purchase price.

We also discuss practical issues such as SBA financing, seller financing, valuation multiples, how to evaluate acquisition opportunities, and what characteristics make a business easier to grow and ultimately sell.

Whether you already own a successful practice or business, are considering acquiring one, or simply want to understand why business ownership remains one of the most powerful wealth-building tools available, I think you’ll find this conversation particularly valuable.

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Transcript

Disclaimer: This transcript was generated by AI and may not be 100% accurate. If you notice any errors or corrections, please email us at [email protected].

You’d be shocked, uh, at how many smart people making two million bucks per year don’t do the tax planning for their sale. They think they did it. Maybe they didn’t put it in their LOI. They think they talked to their accountant about it, but they’re about to close their business sale and their, their tax structure wasn’t even approved by the buyer yet, and now you’re gonna lose 500 grand

Welcome, everybody. This is Buck Joffrey with The Wealth Formula podcast. Uh, before we start today, remember, there’s a website associated with this podcast that you should definitely visit for various resources. That is wealthformula.com. Today, what we’re gonna talk a little bit about is something I’ve talked about before, which is business ownership.

Now, listen, I know that many of you are high-income professionals, and that is a great path, you know, for financial success, right? You’re– You may be making hundreds of thousands, maybe a million dollars or more. You work hard, you earn a great income. It’s great. The problem is that even in the highest paying jobs, there are some significant limitations.

The first one is taxation. You’ve experienced it yourself already, I’m sure, if you’ve gotten into this investing stuff and alternatives as well. There’s this huge opportunity to take depreciation losses and things like that, that you simply can’t take with a W2, uh, W2 job. Now, certainly there are ways to, uh, circumvent that, but cer- but they’re much harder than if you, uh, actually have a business, right?

Second, okay, this is something that I think a lot of people don’t think about, which is, okay, even if you have a great, great salary, you don’t own that asset. Once you leave, it’s done, right? You may be earning, again, uh, hundreds of thousands or, you know, a million dollars or more, but when you stop working, the income stops.

And on the other hand, you get somebody who’s making the same amount on a yearly basis, maybe they have a, a, uh, practice instead of being an employee at a hospital, and they’re making the same amount of money. But guess what happens over time? They have built enterprise value. So not only do they get the fruits of their labor today, but over time, they eventually have the opportunity to cash out with something that they’ve built over years and years.

Now, just to be clear, this is not a call to quit your day job and become an entrepreneur overnight. In fact, for many of us, the better question is whether there are opportunities to acquire an existing, uh, business f- um, that, you know, that you can have an additional to, to your job, right? And, you know, because every day, thousands of profitable small and small, small and mid-sized businesses are, are basically getting sold by people who wanna retire and, you know, have a succession plan, right?

Those same people that, uh, we mentioned before who’ve been working and making money, they wanna get out, eventually they wanna sell, right? And a lot of these businesses can be acquired, uh, with financing and, you know, you can get some management in there and, and, and grow thoughtfully. Whatever the case may be, this is something you ought to actually think about.

And again Hey, if it’s not your cup of tea, it’s not your cup of tea, but, you know, think about it and really consider if you should be involved with some kind of business ownership if you are not. This week’s guest on Wealth Formula podcast, uh, is actually an attorney who specializes in business acquisition, sales, and deal structuring.

And what we’re gonna talk about, what we start talking about is actually, you know, for those of you who have businesses or practices, ways to maximize what you’re actually gonna get for those. But then the second half is really focusing on, well, what about acquiring a business? You know, what sh- you should, you know, what should you be looking for and that kind of thing.

Anyway, whether you own a successful practice or business today, consider, are considering acquiring one, or maybe you just wanna understand what these benefits are, um, this is gonna be a good podcast for you to listen to, and we will have it to you after these messages.

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Welcome back to the show, everyone. Today my guest on Wealth Formula podcast is Joe Principe. He’s a international M&A and attorney, managing partner of Principe International, which is a firm specializing in business acquisitions, exits, complex deal structures. Uh, with experience in elite firms like Freshfields and Baker McKenzie, as well as the SEC, he advises business owners and investors on high stakes transactions, tax structure, liability, uh, protection.

Uh, his, his work, uh, really focuses on helping entrepreneurs maximize value while minimizing risk during major business transitions. Welcome, uh, Joe. How are you?

I’m doing good, Buck. Thanks for having me, and I look forward to the opportunity today to tell people some, some more about how they can protect themselves when they’re investing their money, whether it’s through a partnership, investing in a friend’s business, selling your business- Sure

or otherwise.

I know, uh, you are, uh, um, heavily involved obviously with M&A, and probably the most common thing that I hear in our group is, well, there’s a lot of dentists. They sell their practices and, and they actually do really well. When you have business owners and they, you know, like how early should they, uh, start preparing for an exit and, you know, like what, what are some of the things that they ought to be thinking about?

Yeah, so there’s really two big advisors you get when you’re selling your business. There’s… Well, there’s three. There’s your broker, there’s your accountant, there’s your lawyer. What people always end up doing, and I, I literally live and breathe M&A from the 1 to 10 million, uh, sale range, which would, which would probably people listening to this here will be a business that they own, all the way up to the $100 million dollar, dollar plus range.

And when we’re down there in that 1 to 10, 1 to 20 million range, people always wanna push hiring the lawyer to the way back at the end, and it comes back to bite them. Uh, just, just for one example, uh, to answer the question, uh, you, you should really hire that lawyer as early as you can because we get in there and we make sure that you’re sale, you’re exit ready.

And things that these type of people miss and mi- You’d be shocked, uh, at how many smart people making two million bucks per year don’t do the tax planning for their sale. They think they did it Maybe they didn’t put it in their LOI. They think they talked to their accountant about it, but they’re about to close their business sale and their, their tax structure wasn’t even approved by the buyer yet, and now you’re going to lose 500 grand just because you didn’t hire a competent attorney early enough.

So there’s a lot of stories like that. It’s kind of surprising. You think people making a million, two million a year are having perfect advice all the time, but it’s just not the case.

So, um, let’s talk about that, like, in terms of the taxes in particular. Yeah. Like, what, what kind of… You know, give us a rundown of, like, you know, what, what’s the difference between, you know, saving an extra half million dollars a year in taxes?

Like, h- how, what are some of the things that you do that are important? Is it about, like, you know, whether you’re buying a business or buying, uh, the assets, things like that or, or how does that work?

Yeah, I know that. That’s definitely, it’s up that alley if it’s an asset purchase, a stock purchase, that type of situation.

The thing is, is that a seller and a buyer are at odds when it comes to s- tax structuring. Most oft- often it is super advantageous to the buyer to get asset purs- purchase tax treatment. But in a lot of cases, for example, I was … I’m just gonna think of recent cases. Just dealing with a client this morning where the seller wants QSBS stock, so they want this qualified small business stock sale tax treatment.

You don’t need to know the lingo. Yeah. But on the other hand, the buyer, my client, put in the LOI way months ago upfront that we’re gonna get asset purchase tax treatment. Seller’s attorney never, uh, I mean, I don’t even think they looked, frankly. This, the broker, and let me tell you, I love business brokers.

I work with them all the day. I do brokerage work, but they miss that stuff all the time for their multimillion-dollar clients. So that’s one example. Um, often you’ll hear, hear people say that if you’re a seller, a stock purchase is actually more advantageous for you. So just keep stuff like that in mind.

Sure.

Sure. That makes sense.

Would you say that that’s probably the biggest mistake? Uh, what are some of the other, you know- Oh, yeah … mistakes that, that, that owners make that, you know, you, you probably need to

address early?

Yeah. There, there’s a lot of them. It, it really does shock the conscious. Um, I always mention that one because I’m literally telling people every day, even my own clients, “Stop missing this,” and they still do it, and I have to fix the LOI.

And so another big one is working … This, this concept might be too legalese for people, so I’ll break it down, of working capital. Mm. So very often people wanna sell their business, and they think to themselves that, “Well, I’m gonna get more money for my inventory.” So, I mean, this might not apply to a medical practitioner.

Just take an Amazon e-commerce store seller- Yeah … as a hypothetical. So there’s these little pieces of the business that a seller often thinks that aren’t gonna be included in the purchase price. Working capital is one of them. Part of that’s inventory. Some, uh, if you’re a construction company, we have this thing called w- like, you know, basically the projects that are under construction, we call it works in progress.

Right. So this, these are all these pieces, these elements of working capital, which is, I’m not gonna get into how to calculate it. Uh, and sellers very often have never talked to, like, their broker, who’s the guy who represents you when you sell a $1 to $20 million business. Your broker won’t bring it up. It won’t be in your listing.

So now you’re not even educating the guy who’s gonna buy your business if working capital is included or not, and it totally will change the purchase price by 500 grand in a $5 million business.

Sure.

And so, uh, that’s another one, and that ties us to a really interesting thing is- Uh, people aren’t aware ’cause it’s not like selling a real- piece of real estate.

Uh, your business listing when you sell your business is so critical to have the little pieces in there like, “Here’s the tax treatment, guys.” I got that out of way j- out of the way just by putting it in my listing. “Here’s the working capital, guys.” You get it l- out of the way up front, and suddenly you’re doing a fantastic deal, but most people never do that.

It’s very rare.

Yeah. Yeah. Um,

you

know, what kinds of things drive, uh, valuation?

Yeah. Yeah, yeah. That’s a great question as well. I thi- so first of all, what I like to say is there’s this, uh, there’s the, like, let’s say the spectrum of, uh, ba- based purely on how much, uh, s- seller discretionary, how much money, let’s just say, you’re taking home as an owner of a business.

If you’re in the 1 to 5 mil- let’s, let’s say 1 to $2 million discretionary earnings range, you’ll get a certain multiple, and it’s usually within a specific range, like 2 to f- uh, 2.5 to 4.5x is very normal for that type of business. And then when you’re earning a little bit more, say you’re earning 5 million per, uh, per year plus SDE, then you’re gonna be in a different range.

You might… It depends on the industry, but you might be in an 8x, a 12x range. Mm-hmm. So those… That’s the key baseline. How much are you… Actually, it’s not your gross revenue. People often think that, “Oh, I’m making 2 million bucks gross. My business is worth 2 million.” If you’re making, you know, if your, if your margins are 15%, so you’re making 300K net profit off of that gross, let’s just say SDE to make this all easy.

You’re making 300K. Man, 300K deals trade at 3x, 3.5x. So your business is only worth 900 grand. It’s not worth 2 million. And that’s a big problem sellers have, um, where they’re thinking it’s off of gross, but it’s off SDE. And then back to just answering your question about what are the other core drivers of these multiples.

It, it, you know, if it’s owner-operated, that’s the biggest one you always run into. It’s like you’re trying to sell your business, but you run the business. It’s actually ironic that you have so many of these very smart, intelligent people, but they’re not experts in buying or selling businesses or these investment deals.

So they just don’t know what they don’t know, and they end up s- shooting themselves in the foot. So that’s another one if it’s owner-opera… I’ll give you one last one and shoot it back to you. Let’s see. Um, if your business is 10 plus years old and your staff has been there consistently, you demand and you will receive a premium.

So now you’re in the 4.5x, 5x range of what should’ve been a 3.5x deal because your business is… It’s the well taken care of used car. It’s not that junker that that kid rode into a ditch, and it’s worth so much more. So that’s another driver for you.

You mean, and by the way, those valuations look really different based on different, uh, you know, if you’re in, uh, various fields, right?

Um, th- then the other question I have is, um, you know, kind of what’s going on these days. Like, what– how are those valuations being affected by interest rates?

Uh, that’s a good question. So the main thing you s- so it, it, it connects it in a very interesting way in these 1 to t- $10 million business sales, and I’ll, I’ll hone in there ’cause it’s ve- it’s widely different based on where you’re at in the market.

So if you’re on these 1 to $10 million business sales, what happens is you’re usually, uh, being f- not all the times, but a lot of the times you’re usually being financed by an SBA 7loan. And these loans, uh, they, they definitely have higher interest rates now than they did a couple years ago, but they’re not so much higher where they’re totally destroying the bankability of these transactions.

It’s just a, okay, now it’s gonna cost a little bit more to service this debt. These loans are always 10-year loans, so that, that’s a good thing. It’s, you know, it’s, it’s being pushed down the line. Usually there’s growth plans that are gonna help service that. So it’s not the end of the world. Um, and what you find a lot of people end up doing that are selling businesses of that size is if you’re on the buy side

Or, sorry, if you’re buying business of that size, and if you’re a seller ’cause you get stuck with it, is, uh, say the interest rate you got is at 12%. Well, they- they’ll say, “Hey, I’ll pay you, the seller, 500 grand over five years, and you’ll get better tax treatment when you do that, and just charge me, like, a 6, 7, 8% interest rate.”

So they’ll, they’ll try to get some interest rate- Yeah … uh, rate down through seller financing. Right. Very common.

Right. Right. Let’s flip a, flip a, the switch a little bit and, um, you know, we have people in the show who are interested in buying businesses. Do you deal with the buyer side too, I presume?

Oh, I have s- yeah.

Yeah. Nowadays, most of my clients are buy side because I’m the, uh, I’m the, like, exclusive attorney for one of the biggest business buyer communities in the country called Carl Allen’s Dealmaker Wealth Society, and I do… I can’t say all their deals ’cause people are free to pick a different attorney if they want to, but I just have so many buy-side engagements constantly streaming in the door.

Yeah. Interesting. So tell us a little bit about, you know, the activity on that side. Like, if you’re, um, o- the same types of questions, I guess. Like, what, you know, what should you be looking for when you, when you’re looking to buy a business?

Yeah. And this is straight from the horse’s mouth. People really need to hear this.

Uh, so I often… a- and if you’re out there looking at businesses to buy, I mean, this is right on point. I often have clients who go on BizBuySell, these other listing websites. They don’t realize that the best deals have already been taken off the website ’cause they’re, they’re not full-time scrapers or they’re not full-time searchers.

And so very often they’re already dealing with the pickings, and they don’t even know it. And what you need to be doing instead is you need to look at only listings that are, like, a couple days old. You’ll end up finding the best ones there. Actually- Quick side note, I actually hired an automation engineer to create a fr- a free scraper I’m gonna start giving to people where it does just that.

It scrapes the last 24 hours of listings and shoots them off to business buyers because people are just … They’re missing out on the best deals. So that’ll be up on my website here in a week or so, but that’s just a free thing d- I’m doing for my clients just because of this problem. And real quick, I wanna say this.

One other super important thing that people are always missing when they’re buying businesses is they’re, they get comfortable with, oh, 4X. People say 4X, 3.5X is normal. Uh, people say 4- 4.5X is pushing it. What they don’t know is that when you’re doing an SBA 7A loan, and with a lot of commercial lenders, you’re already pushing the debt service coverage when you hit 4.33.

People think, oh, I can bank it at 4.5, but they don’t actually calculate the monthly cash take-home. And when you run a f- sh- Just run a 5X on a target and check the, you know, debt service coverage with the monthly cash take-home, and you’re gonna be like, “Oh, that $3 million business is making me 16 grand a month, and I took out a $2.7 million loan for 16 grand a month?”

It’s crazy. Now you’re locked into that. You have little buffer. If it goes, uh, belly up, now you got a nice personal guarantee on a $2.7 million loan, and you might just, you know, go belly up with it

You mentioned BizBuySell, which is, like, one of the, you know, major sites for small businesses. Is that kind of…

Like, it- it’s, I’m curious ’cause I’ve been in the market looking for businesses too. I find this, uh, to be a very frustrating thing. Um, is that really your best option? Like, I mean, how, how else do people source, source businesses?

Yeah, so I wouldn’t say it’s your best option. I’d say it’s a really common one that people use.

There’s several big websites out there. In Florida, uh, there’s the, the MLS for real estate brokers, uh, also has business listings, for example. Mm-hmm. There’s all sorts of… There’s, uh, uh, Axial, LoopNet, uh, yada. I can’t remember them off the top of my head. So there are, are several. Uh, the problem is, is that you’re not a professional searcher usually, and so you have to say to yourself, are you gonna take, uh, put in the time that it takes to be a professional soccer player?

Are you trying to be an investment banker and a deal sourcer? Man, oh, man, those guys graduate from Wharton and spend 15 years before they’re experts. So you really have to check yourself if you’re gonna go just hire a s- I don’t do, uh, searching. I mean, I do s- like, I have my sales team help clients who are searching for free, but I don’t do searching as a job.

There’s experts out there, they can be really expensive. They can be 10 to 15 grand, and you might not get very good leads. So that’s a big problem in the space. Um- Yeah … one of my best clients, he’s an expert at just cold calling, uh, off-market business owners, and, uh, just having an… He’s an ex-fireman, so he’s a real, you know, he has good vibes, and people love him when he calls them, and they wanna sell their business to him.

So that’s one route. They’re not often sale-ready, though, when you go off-market, so.

Yeah, it seems like the brokers in the space are not like real estate brokers. I mean, they’re not really spending a lot of time, like, you know, trying to listen to what you want and go and find you stuff. They’re just, they’re, they’re basically representing the sellers, aren’t they?

I mean, they aren’t really doing much of anything else. Y-

you read my mind. Uh, and so it is what it is. The money is on the sell side, in owning the seller representation. A- and there are a lot of brokers that do represent buyers. As part of what I do for clients in certain states, the brokerage spritz- splits are really common, and I’ll do buy side brokerage i- in certain situations for those clients.

But yeah, I mean, brokers are… You know, there’s a lot of great, really knowledgeable brokers out there, so I’m not gonna smack talk them. But they’re also there just to make a commission. They’re not there to, like, spend all of their time and money finding you your perfect deal necessarily. Um, so yeah, they’re not really the choice for sourcing.

Yeah. So you’re, you’re really talking about an internet-heavy scraping sites, things like that, or cold calling. What do you think of, um, franchises?

Yeah, okay. Franchises are very interesting. You know what? I’m even reading, uh, wait, what was it right now? The E-Myth right now, where he, he goes hard, and you’ve probably read it.

He goes and talks about franchises and stuff. It was funny. I mean, it’s old news, obviously. And, uh, so franchises, I mean, the go-to statement, uh, that… So I’m not an expert in franchises, first of all, so I’ll make this brief. The go-to statement is, uh, uh, people often say, you know, there’s better opportunities in buying a small business with an S- SBA 7loan, ’cause you get really good terms on those loans.

Yeah. It’s, you only have to put 5% down on a 7loan. So I have clients, uh, so, like, I had a guy, a $5.5 million, I don’t remember the exact numbers, but it was 5% down. So 5% on 5.5, I guess that’s 250, uh, 275, something like that. He spent 275 to buy a business that was generating, like, 1.5, I can’t remember, 1.7, uh, uh, SDE, which is crazy.

So anyways, um, yeah. Anyways, so franchises, don’t know a lot about them. There’s usually better deals in these smaller, uh, business acquisitions that, that’s what people often tell me. When people, they, they ask me to ru- re- review their franchise docs, I’ll do that, but it’s few and far between.

What have been, um, some of the more common or more successful, um, acquisition i- in terms of the space?

Like, like, what, what’s hot right now? Like, what, what are people looking for?

Yeah. And, and so, it, it, it really goes back to the thing you wanna be looking for, the whole investment thesis of buying a business generating free cash flow of one to $10 million is getting that 2.5X, 3X multiple deal. If you’re looking at, if you can only find the 4.5Xs, there’s something wrong with how you’re searching.

You’re not getting to the deals quick enough. And so I have a client right now, we’re closing, it was pushed, we’re closing on the 12th. They’re buying a 1 point… Well, now it’s, like, 1.09, but 1.1, because we negotiated the purchase price down. But, uh, $1.1 million electrical contractor in Arizona at a 2.5X.

Fantastic deal. That, that’s all, that’s a win, and obviously you gotta due diligence it. You have to have a quality of earnings done with- by a, you know, an expert. And so there’s all these things that go into the pie, but that’s what you need to be looking for when you’re buying a business.

Yeah, you know what, and when you say that, too, about the contractor, uh, the other thing that comes to mind is when these businesses are that small, they’re often heavily dependent on on the owner.

You know, like, I mean, the contractor in this case probably was a contract- you know, he was, probably was a contractor of the owner. I mean, I mean, how often with these smaller businesses do you really get something that isn’t, you know, heavily dependent on, on the owner?

Yeah, so, uh, you’re, you’re right. It’s very common that these are owner-operated businesses.

When you start to get to the 750K SDE, so that, uh, that’s the, again, that’s the- Yeah … owner’s take-home. When you start to get to that, to the 1.5, they’re not the GM anymore. I mean, that guy’s on the golf course earning 1.5. And so, um, that … So it is the higher you get, the more l- uh, the more likely it is for it to have a GM, but also part of the battle plan, and whenev- whenever we’re working on deals, there’s just a strict process we follow.

Uh, part of the battle plan is that we put a GM in place. We get a headhunter done before closing who has the right license. As of the time of closing, he’s starting. That GM is now, uh, doing the transition. He’s learning everything from the seller. And you didn’t ha- I mean, sure you have to do stuff, but now you’re not coming in and buying a job.

Um, so that’s, like, part of the, the process. Yeah.

Yeah. Yeah. I mean, uh, what, what do you … I mean, in terms of the clients that you, that are buying businesses on your end, is that g- generally a sweet spot then, like, over, over 750 seller’s discretionary earnings?

Uh, absolutely. Um, that’s what I tell people to be looking for.

When you’re, when you’re down at, like, 500, and then you just start running the numbers, you just start saying to yourself, “Wait, why am I doing this again?”

Mm. Yeah.

When you get to 750 plus to 1.5, now you’re saying to yourself, “Oh, uh, now I know why I’m doing this.”

Yeah. Yeah. Absolutely. Well, interesting. So tell, um, tell us a little bit, uh, more about your business and, you know, how, how people can get in touch with you.

Yeah, absolutely. So you can get in tou- touch with me at my law firm’s website, principe.com, and the spelling’s probably on here somewhere. And, uh, my intake’s in there, so if you’re gonna buy a business, if you’re selling a business, if you’re doing a large investment transaction or a partnership, uh, you can just go through in there.

You can book a call through my system, and then after you kind of go through that process you’ll get on the phone with me or one of my attorneys, and we’ll walk you through the steps to, to handle your transaction for you

Fantastic. Thanks so much for being on the show today, Joe.

No problem. Hey, thanks for having me, Buck.

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Welcome back to the show, everyone. Uh, hope you enjoyed it. Again, just something to consider, right? Business ownership is incredibly valuable, not only from the standpoint of, you know, the tax benefits that you get from it, but also having an asset that you can, that you can sell eventually, right?

Now, I know a lot of people think, “Well, gosh, you know, I, I’ve got a full-time job, and I don’t have time for this,” and I get it. Um, so one thing that, uh, a lot of those full- you full-time job people ought to consider is, well, why don’t you go create your own practice, right? You may have a busy practice already that you’re working for, but is there any reason you can’t create your own practice, something that you can sell later?

And the reality is that there is some pain that goes along with that, right? There is some short-term pain. But I know that for the most part, you know, there’s, there’s a, a kind of a shortage of doctors and people who are highly specialized. And, you know, give it a year or two, and you’re going to be making as much money as you currently are, and you’re gonna have an asset that you can sell as well.

Anyway, just some thoughts to consider. This is Buck Joffrey with Wealth Formula Podcast signing off.

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