How MSP Founders Can Save Millions in Taxes Before Selling Their Business

Nick Bartolo joins Talk Tech to break down how MSP founders can prepare for a successful business exit while minimizing taxes and protecting long-term wealth. This episode covers QSBS strategies, F reorganizations, post-sale investment planning, and the financial mistakes founders should avoid before an acquisition.

Key Insights:

•  How MSP owners can use QSBS and F reorganizations to potentially reduce capital gains taxes 
•  Why preparing your business for sale years in advance creates more exit value and flexibility 
•  Post-exit investment and tax strategies that help founders preserve and grow wealth after closing 

Takeaway:
If you’re an MSP founder thinking about growth, acquisition, or succession planning, this episode offers practical insights to help you maximize your exit and avoid costly mistakes.

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Transcript

SPEAKER_01 0:03

Welcome to Talk Tech with Rob Scott. Welcome to Talk Tech. I'm your host, Rob Scott, and today we're visiting with my friend Nick Bartolo. Nick, welcome to the show. Hey Rob, good to see you. Good to see you. I really am excited to have you on today. You and I have been talking about a lot of interesting stuff. And just like I do with other guests that I invite to the show, if I meet somebody that I think is cool and interesting and funny, then I want to invite them to be on my show and you definitely check all three boxes.

SPEAKER_02 0:38

Oh, so you're setting the precedence that I need some funny jokes now. So pressures on, challenge accepted.

SPEAKER_01 0:44

All right. I'm sure, I'm sure that that won't be a problem for you because I think it comes naturally. But for those who don't know you, Nick, why don't you introduce the audience to uh who you are and what you do?

SPEAKER_02 0:57

Well, you know, again, thanks, Rob, for having me on. Um, Nick Bartolo. So what I do is I founded and run a wealth management firm called Essential Partners. Okay. So in Essential Partners, what I do is I specialize in working with business owners who are likely to have an exit or sell their business at some point in the future. All right. So that's that's what I'm up to now. I mean, I could I could take you back to birth, Rob, but I don't think we all want to go back that far. But I kind of started this journey in working with business owners first as a CPA. I kind of came from a very technical background, did accounting, got fascinated in investments during the dot-com bubble. All right. I call it, I call it the OG Tech bubble. I mean, we may have another bubble going on right now. Time will tell. But I got fascinated with investing during that time. And then I realized you could make a career out of that. So for 17 years after getting my MBA, I worked on Wall Street. And it wasn't in wealth management, it wasn't doing asset allocation. It was actually understanding and analyzing businesses, traveling around the world, meeting with CEOs and CFOs of big Fortune 500 companies, and actually making decisions on whether or not we should invest in those stocks, sometimes bonds, for large institutions like pensions, endowments. So we were managing money for those types of constituents. Okay. After doing that for you know 17, 18 years, I wanted to take that and you know kind of be a greedy capitalist, add value to my family, but more so like add value to potential families, where I took this institutional knowledge and then started to manage money for families and business owners. So that's what I've been up to over the last lump number of years.

SPEAKER_01 2:45

And and and and that's the context in which I came to know you. One of my mentors is a founder of a very successful B2B SaaS company, and and uh you're his wealth manager, and he told me amazing things about you. And is so often, you know, this this world works is you know, you you know, it's what circles you run in are the people that you meet. And and what I understand about you, Nick, that makes your services different than maybe other wealth management services is you really uh have the expertise to help founders prepare for an exit. Uh can you go into that a little bit more? I think a lot of people think that they're gonna just build their business, run their business, and one day they're gonna sell it and it's all gonna happen magically, but in reality it's not quite that simple. Uh, talk me through how you help founders uh prepare for a potential exit.

SPEAKER_02 3:43

Yeah. It's a good point, Rob, because oftentimes what you see is that money is so emotional. And when you're a business owner and your whole identity and your cash flow and everything that surrounds your life, your social life is all wrapped in your business. Sometimes that decision to sell actually becomes overly emotional. So you're having a bad couple quarters, you're dealing with some folks on your team that where you're having to micromanage them. You know, I had a business owner recently tell me that they just sick of uh babysitting adults, okay? And they're ready to just like take this emotional purge and sell their business, right? Which is absolutely the wrong approach. So what we try to do, and I think it's like very different than let's say a financial advisor. I think people have a lot of can misconceptions or they have accurate uh perceptions of financial advisors in that they take your money, they charge a fee, and they just like put it in a cookie-cutter portfolio. All right. We really pride ourselves in getting involved in planning well before the sale happens. And that's on multiple dimensions. So the first thing is that a lot of businesses, they're just they don't know what to do in order to actually prepare the actual business to be sold, right? So that's a critical first step. Their books aren't in order, right? They don't have systems and procedures that are documented. They may be the driving force, manager, doer in the business, which doesn't necessarily set it up well, to be sold, all right? Those are just like some of the operational aspects. But then what we do and where we get involved is actually thinking about quantitatively and processing that decision on if you should be selling your business in the first place. What happens if you could potentially sell that business two, three, four, five years down the road? And is that money that you're going to have on an after-tax basis enough to actually fund your lifestyle once you sell? So you can live your live your life, step away from the business, do the things you've always wanted to do where you didn't have time, where you're in the business, you know, take that trip, pay for your kids' college, whatever the case may be, right? So a lot of people don't necessarily connect the dots from that pre-sale decision to sell, how much money they're gonna have after tax and what that's going to mean for their life after the sale. Okay, so because the way I look at it is like, how can you possibly know when to sell your business if you don't know how that money is going to be invested and whether or not it can actually support your lifestyle? Okay. And so I think there is a big planning disconnect there. Not to mention, and we can get into it whenever, but not to mention all of the tax strategies that you can. Well, let's pause right there.

SPEAKER_01 6:36

Let's pause right there because I've heard a lot of that messaging before, what you just talked about. We help people get ready, we help them prepare their business, uh, we help them plan. That's not a unique differentiator from what I've seen in the marketplace. But one of the things that I think makes what you do very unique is your tax expertise and the tax strategies that you've implemented for your customers. And I'd like to jump into your whole reasoning behind focusing so much on tax strategy and the importance of the qualified business stock and strategies that you've developed around that, to where founders today, if they plan correctly and have the right structures, can really significantly reduce their tax exposure, which gives them much more money to finance their lifestyle such that when they do the calculation that you're talking about, the tax savings really put a lot more money in the net take-home, so to speak. So, talk about your background with developing these tax strategies. What are you seeing that's working the best? And what is the state of the art when it comes to tax strategy for founders who are exiting?

SPEAKER_02 8:01

Okay, yeah. So that's that's a good point. And so there's a few, there's multiple dimensions of this, as you know, as you and I have talked about. And it can happen five years before a sale, and if nothing has happened, let's say before a sale, there's still you know strategies that can be implemented that could save 20 to 30 percent of a tax bill after the sale, depending on a multitude of factors, including the timing of the sale. So let's just kind of unpack some of those one by one, right? So if you have your business set up, you have a longer-term time horizon on when you want to sell. Say it's three years, say it's five years, okay? And let's say you're sitting there, and a lot of small businesses, right? They're they're an S-corp, right? They may be, you know, operating as an S-corp because of the tax advantages there. And so they can't necessarily, they don't have the entity set up as a C Corp in order to take advantage of Section 1202, which is the qualified small business stock, as you alluded to, all right. So if those businesses are an S Corp and they want to take advantage of QSBS, they can actually convert to a C Corp, right? There's a special process. You can't just go to your local attorney and convert to a C Corp. There's a special process in order to do that, and there's attorneys that specialize in that type of transaction or that type of transition to that entity to make sure that it's done properly, all right? But let's say you do that. Let's say your business is valued at $10 million at the time that you go to convert from an S-corp to a C Corp. It is true that during that five-year transition period, there are going to be some tax disadvantages of being a C Corp because the C Corp is an actual taxpayer, 21% for federal purposes, and then any state taxes, depending on the jurisdiction. So you are paying more tax. So if you take so then if you take distributions from the C Corp, you pay an additional dividend tax on that for your personal income tax. Okay. The dreaded double corporate tax, which is why everyone uses the S-corp. Yeah, exactly. So yeah, we all we all love double tax. That seems fair, right? And so anyway, I die I digress. We don't we don't want to talk about estate taxes and all kinds of stuff now. But so let's say you execute this conversion and your your company at that time is valued at $10 million. Okay. If you wait then five years and you execute a stock sale of your C Corp, you can get a 10x tax break on the value of your company at conversion. Okay. So in this example, it's $10 million at conversion. You now have $90 million that you can get tax free, right? When that business is sold, if it's a stock sale. And I say $90 million because that initial $10 million that you created in value at the conversion, that's still subjects subject to capital gains tax. But the incremental you can get up to additional $90 million, okay, if you wait five years. If you wait three years, you can still benefit from this conversion, but it's 50% of the gain. Okay. So 50% of that incremental gain could be tax free, right? So a tremendous benefit just by knowing that this exists and working with the types of attorneys that have successfully executed this type of reorganization historically.

SPEAKER_01 11:40

Okay. And what you're talking about is commonly referred to as an F-type re-org, correct? Correct. Yes. And and the effect of it is to reorganize an LLC or an S-corp that's taxed as a partnership into a C Corp structure that can then over time qualify for the qualified small business tax exemption that you just described. Is that correct?

SPEAKER_02 12:06

That's exactly right. And with the one big beautiful bill, there were some modest changes to it. One change being that prior to the conversion, you have to be less than a $75 million value of your business. Okay, so if you're above $75 million, you can't justify anything below that, then this isn't available to you, this QSBS treatment. There's a lot of technicalities, you know, related to this. That's why you know I advocate specialists in this realm, but it is a substantial benefit. The other risk I would point out is that a lot of acquirers, I would say nearly all acquirers, they prefer to do an asset purchase, right, as opposed to a stock purchase. And that's because if they do an asset purchase, they can effectively amortize or depreciate that value that they're acquiring, where a stock purchase you can't. Also, a stock purchase, and you know this, speaking of the choir here, you're assuming the full liabilities of that corporation, whereas an asset purchase you're not. Okay, so there are there are a couple wrinkles, and some would argue, and there is credibility to this, that a stock purchase may warrant a modestly lower valuation, right? I don't think it's low enough to you know have the full tax burden, right? We're not talking about that, but whether it's 10%, whether it's 15%, modestly lower valuation, you could see that in a negotiation.

SPEAKER_01 13:41

The other thing that we've seen, Nick, is the use of reverse triangular mergers. So imagine a structure where a NUCO is the acquirer of the stock, and then the purchaser merges with that company or acquires the assets from that company. Uh, and that way you could theoretically create a structure which gives you the best of both worlds, including the asset purchase concept that favors the buyer and the stock sale strategy that favors the seller. So there are some complicated structures. I'm thinking back to my days when my client Xerox uh purchased ACS and I was involved in a litigation involving their reverse triangular merger, and I learned more about that stuff than I thought I would ever need to know. Um but but the other thing that's interesting, Nick, is that this uh qualified small business stock for people who have substantial businesses who might might exceed the protection of a single entity, uh you've developed some stacking strategies that could extend the the benefit of the qualified small business stock uh tax strategy even to many multiples of what a single entity could achieve.

SPEAKER_02 15:14

That's right, that's right. And so, and again, like I always like to point out like the personalization aspect of it, right? Because depending on someone's heirs, like whether or not they have kids, whether or not they're married, you know, whether or not they have causes that are near and dear to their heart that they're already donating to, that can have a big influence on what strategy is going to be most optimal for them. Like none of this is like totally optimized, but that personal aspect is huge. However, so let's say you have a scenario. So we talked about this conversion strategy. Let's say alternatively, you have a scenario where a company was started as a C Corp. So it's already been a C Corp, it was under $50 million in value when it was started as a C Corp, and it's just been operating that way for the past, let's say, 10 years, okay? That type of situation would most likely be eligible for QSBS, but there's a limitation on how much would be tax free on a transaction. It's $10 million, okay? And so if you have a single owner and they get this $10 million exemption, there's options to actually, as you mentioned, stack that $10 million across different entities, right? So these entities could be a charitable remainder trust, it could be a non-grantor trust with the benefit or the beneficiary being a child or a family member, a parent, a wife, et cetera, et cetera, okay? A husband. And so if you have multiple tax IDs and multiple taxpayers that own a portion of that corporation, they can then effectively stack these $10 million tax exemptions for each of those entities. Okay. So they need to be different in characteristic. You can't just stack, you know, 10 charitable remainder trusts and sell the stock within those charitable remainder trusts, have the distributions flow back tax-free to you as the first beneficiary of those charitable remainder trusts. But there's a number of nuances and there's a number of strategies that have been executed successfully where you can stack multiple $10 million exemptions in order to further not pay not pay capital gains tax on the sale. I will say one other thing about QSBS that some that people should go wide eyes wide open into, and that is that there's a lot of states that actually don't recognize QSBS. Okay. I saw I was working on um an Illinois case recently, a California case. And so you're still paying state tax, you're not avoiding the state capital gains tax um for a transaction because of QSBS, but the federal tax is obviously much more common and higher for all taxpayers. Okay, so that is that is another important caveat.

SPEAKER_01 18:19

That makes good sense. The other, I think, unique value differentiator in what you do and what I've seen in the market is you not only help founders get ready, but help them with tax strategy going in, but you also help manage their investments with uh some non-cookie cutter strategies for how to maximize the return on that after tax money after the sale. So why don't you talk about the services that you offer to your customers in the in the context of post-sale and what strategies you've seen as being working the best for your customers now uh after they sell?

SPEAKER_02 19:04

Mm-hmm. Yeah, at the end of the day, we're a money management firm. Okay. Like for us, all of the tax planning and the tax mitigation, people pay me paying less tax on the sale and doing all that planning, that's sort of icing on the cake. But at the end of the day, like our job is to manage the money for someone after the sale. Oh, and oh, by the way, like because I think I have this nerdy fascination with tax, like we want to do that as tax efficiently as possible because portfolios can essentially bleed out if it's not structured properly with the taxes coming out year after year on ordinary income. You know, you try to rebalance your portfolio, you're paying capital gains tax if it's not structured properly. Okay, so managing money for business owners, to your question, managing money for business owners is an entirely different exercise in my experience than managing money for, let's say, a corporate executive. And the reason why is that business owners live with this day-to-day decisions strategy, cutting costs, figuring out how to grow revenue, and they've controlled all of these cash flows and all of these decisions to increase their net worth over time. All right. And so when you have someone who's going from that level of control and that mindset, and a lot of them, by the way, don't have many investments or any investments outside of their business. Okay. So when you get this pile of cash after you sold your business, it's like a completely different emotional paradigm than managing money for someone who has just sort of squirreled money away and grown their retirement or grown even a big pile of money over time. All right. So the first thing that we do is we start slow. All right. First, we try to mitigate the taxes on the sale of the business after the sale through investments. And you and I have talked through some of those strategies in the past, Rob, but really utilizing tax loss harvesting with some of the money that's been received from the sale in order to generate investment returns first and to be a part of that asset allocation, but also to reduce the taxes on the business sale. Okay, so so really marrying investments with tax mitigation to then have more money to make money with, right? Like I'll give you, I'll give you a little example. Like, let's just say, and I'll get out my um my old school HP 12C here, but let's just say you know you have a million bucks that you save somebody on taxes, all right? Let's say it was a yeah, let's just say you save a million bucks, and instead of paying the government that you can invest that over 20 years, earn a 9% return. That turns into 5.6 million dollars, right? So you can just see, like, by being able to reduce the tax. Taxes, you have more money to compound to where you're creating. Shoot, that's a nice exit for a lot of people in end of its own right. Just the tax savings, right? Turning into 5.6 million. Okay, so that's one piece. But then that type of strategy, you can continue to have that investment which uh participates in the broad US stock market or global stock markets, while also continuing to provide tax benefits into the future. Okay, so that's one sort of core pillar of not only generating returns within the stock market, but also reducing tax. More broadly, then, when we think about business owners, it's about generating good returns that's going to keep up with purchasing power and then some. So think high single digits, low double digit returns, but wanting to do it with much lower volatility so that portfolio can be resilient across all tip all different economic environments. Okay. Let me give you an example. So financial asset prices have historically moved with changes and expectations around economic growth and inflation. Okay. So if you think about that, it's like think of this stagflationary environment. I'm sure you know that term from the Yeah, I was born in 1970.

SPEAKER_01 23:20

I know what that is. Exactly.

SPEAKER_02 23:21

Exactly. I was in the 70s myself. So we know that term, right? I was a toddler, but you know, I was there. And um, and so stagflation is this idea that the economy isn't growing as fast as people think, but inflation is going up much more than people think. Our most recent example was 2022, okay. In 2022, that's when we had inflation spiking to 9%, and the economy was like, eh, we didn't go into a recession, but it was sputtering, okay? And so if you think about this with financial asset prices in 2022, stocks were down over 20%, all right? And so I like to obviously bring things down to first principles thinking. So think about your business, think about an MSP, like anything, right? It's like if your revenue isn't growing as fast as you thought, but yet your costs are rising more than you thought, what's gonna happen? Your cash flows are gonna compress, and when a cat and when the cash flows of a business compress, the valuation, at least temporarily, also goes down, right? So it should be no surprise in 2022, that stagflationary dynamic that stocks were down over 20%. All right. And so that's one of the four examples of how these two variables change and how it impacts asset prices. In that stagflationary environment, you want to own assets that are actually participating in the inflation. All right. And so commodities in 2022 were up over 20%. Gold, which has been a long time holding of all of my client partners, gold was up a little bit in 2022, but far outperforming stocks. All right. So it's not about like predicting exactly where the economy and inflation are going to be. It's about ensuring that portfolios have some exposure to the various asset classes in order to generate returns across these cycles. I'll give you, I'll give you one last example before like everybody starts nodding off on all my you know economic investment speak here. But COVID is another good example, right? Q1 of 2020, I don't think any of us can ever forget that, right? So, in that environment, what happened? So the economy came screeching to a halt, so economic growth was lower than people thought, and inflation collapsed as well, right? No one's buying anything. Of course, inflation is gonna collapse temporarily. That's what's called a deflationary environment, right? When economic growth and inflation are going down. Of course, lo and behold, if you use the same business analogy, stocks were down 35% in Q1 of 2020, right? Because revenue, profits, everything is collapsing at that point. However, gold was up 10% in Q1. Long-term treasury bonds were up 20% in Q1. And treasury inflation protected bonds, so basically inflation-linked US government bonds, they were up 15%. All right. So again, I'm not advocating that someone should have 30, 40, or 50% in those types of assets. But imagine if you had 10% in gold and 10 or 15% in US Treasury bonds, right? You're having a very different experience than someone who's 100% in stocks. You just sold your business, you're down 35%, and lo and behold, you're letting greed take over and you're selling everything at the bottom, right? That I mean, that's that's the natural inclination. You took your life's work, you put it in the stock market, and you're just basically getting flushed, right? So it's about trying to moderate through these cycles, and then over time, when you're rebalancing and being opportunistic, you can generate a really nice return.

SPEAKER_01 27:14

And what I've heard from some of your clients that you know the the money from the exit is just the tip of the iceberg with what can be done with the investment strategy. So, you know, I would say to those founders that are holding on to every last penny, you know, in a sale, uh, you don't need to get every nickel out of your sale if you've got the right uh strategic advisors from a tax perspective and the right investment strategy with the money after closing. You could still turn that 5% less than you wanted into a big pile with the right strategies.

SPEAKER_02 27:51

You really can. And I mean, the investments, the investment tax strategy after the sale, you know, like it can be the difference between doubling or tripling your net worth over a 20, 30 year period or running out of money. Right? These small changes, you know, one 1%, 2% of tax drag over a long period of time while you're spending the money and continuing to potentially draw it down, it literally, you know, I've seen the cases where it can be the difference between between those two scenarios.

SPEAKER_01 28:23

Uh if if someone's a business owner, maybe they own a SaaS business, maybe they're the CEO or a founder of a MSP. Um how do you determine which of those companies are the best fit for your services? How does someone who's thinking about maybe selling their business someday or maybe even involved in currently a process to sell their business? How do you evaluate um who's the right customer for your business? If you were a SaaS business, I would say, tell me your ICP or ideal client profile. But I just want to understand, you know, who's that customer that's most likely to benefit from your services.

SPEAKER_02 29:08

Yeah. Yeah. So for I don't have any hard and fast minimums, you know, when I think about like this ideal client, but the more money someone has, typically the more impact we can have. And not just because it's larger dollars, just because there's different strategies available to different wealth levels. Meaning, someone that has a $15 million exit, we can help a lot more than someone that has a $1 million exit. Okay. But typically, you know, we'll help folks anything from $5, 10 million and up in order to be able to execute some of these strategies, right? So, you know, we have clients in that five to ten million dollar range, and we have clients, you know, north of 50 million. So it's it's really all across the board. But again, this concept of like kind of like five and ten up is where we can really have a bigger impact.

SPEAKER_01 30:01

That makes sense. And if someone wanted to start a conversation with you or continue the discussion on the topics that we've discussed today, what would be the best way for them to get in touch with you?

SPEAKER_02 30:13

I would say the best way to get in touch with me is like you can just email us, you can go to the website. I mean, the email is info at essentialp.com, you know, E-S-S-E-N-T-I-A-L P is in partners.com. And our website, same thing, you know, essentialp.com, where we have contact information there.

SPEAKER_01 30:36

Before we go, I just want to ask you this burning question that I've been thinking about.

SPEAKER_02 30:42

I gotta deliver on a joke right here, Robin. All right, I'm ready. You want to hear the question first, or you want to do the joke first? No, no, no. I'm gonna I've got to try to weave a joke into the question.

SPEAKER_01 30:52

Perfect.

SPEAKER_02 30:53

Into the answer.

SPEAKER_01 30:54

Yeah, well, yeah, I would say that you know, my question is if if you had from all of your experience, from Wall Street to everything that you've done in tax and wealth management, investments, if you could say, you know, one bit of advice to a founder or business owner that's thinking about exiting, you know, what is it that you could share with them that's the most meaningful takeaway that you think that they could get from your experience?

SPEAKER_02 31:25

It might it might be a little unconventional, but my advice to that person is don't wait. Okay? And I don't mean like don't wait, like call our firm and start planning. Like, no, I don't mean that. I mean don't wait in preparing your business to be sold. Okay. And the reason why is that the future is entirely uncertain, and you may get hit, you may be the only one in your family that's involved in the business, and you may get hit by a bus tomorrow. All right. And if you get hit by a bus tomorrow and your business is a mess, it's not ready to be sold, you haven't been diligent about preparing that business, you're leaving your family, like not only have you died, which we're all sad about that, but you're leaving your family who's devastated from your death with now a business that doesn't necessarily have any value. Okay. And so if you take the steps now to prepare the business to be sold, put some of the pieces in place and have those relationships to where if something does happen, right? You you know a broker that can sell your business. Like we don't, we don't, we don't do that, obviously. But you know a broker, the business is actually prepared to sell. Who knows? Maybe you do have some other tax and investment strategies. But by just preparing the business to be sold and setting your family up for that, you know, terrible situation, I think that's like the best first step that anybody can take.

SPEAKER_01 32:49

Yeah, that's excellent advice. And I always say preparing a business to be sold is good business whether you're gonna sell or not. So true. And what I've heard. Guess what?

SPEAKER_02 33:01

You'll make more money along the way.

SPEAKER_01 33:03

And what I've also heard is the exit rate is 100%. You're either gonna exit on your feet or not on your feet. Unfortunately for all of us. And so I heard the death rate is still 100%. We need a that's excellent advice, Nick. I will challenge you to a lawyer joke contest. I'm gonna go first. Oh my gosh. Oh my gosh. Go ahead. Why does a shark not bite an attorney? Professional courtesy.

SPEAKER_02 33:40

Oh, I'll give you a more of a finance investing one. It's gonna be very lame, though. Like, um have you ever heard of the two-handed economist?

SPEAKER_01 33:53

No.

SPEAKER_02 33:55

On one hand, it seems like the economy is growing strongly, but on the other hand, there's some cross currents where it could be not as strong as people think. Sounds like the weatherman. Exactly. Exactly. Economics, the dismal science.

SPEAKER_01 34:11

Ladies and gentlemen, my friend Nick Bartolo, if you've got any questions about uh qualified small business stock, uh investment strategy, preparing your business to exit. I can personally say Nick is amazing at what he does, and he will serve you very well. So if you're in the need for additional information about any of those topics, reach him at EssentialP.com or reach out via email, and uh I'm sure he'll take good care of you. Nick, thank you for joining.

SPEAKER_02 34:46

Thanks, Rob. Great to see you.

SPEAKER_01 34:47

Good to see you too.

SPEAKER_00 34:49

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