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Index/Finance/Best But Never Final: Private Equity's Pursuit of Excellence
Best But Never Final: Private Equity's Pursuit of Excellence artwork

Rollover Equity and the Power of True Alignment

Best But Never Final: Private Equity's Pursuit of Excellence · 2026-03-17 · 45 min

0:00--:--

Key moments - from our scoring

Substance score

66 / 100

Five dimensions, 20 points each

Insight Density14 / 20
Originality12 / 20
Guest Caliber16 / 20
Specificity & Evidence11 / 20
Conversational Craft13 / 20

Rollover equity - where a business seller retains ownership in the deal structure - is a cornerstone mechanism in lower middle market PE, particularly for founder and family-owned businesses. Doug McCormick and Lloyd Metz explain that rollover works by allowing sellers to exchange their existing equity for equity in the new PE-backed entity tax-free, while monetizing the majority stake at sale. A seller might own 25-50% of the post-deal enterprise, creating meaningful alignment with the PE firm's growth strategy. The tax efficiency is substantial: if a $10 rollover investment compounds at 4x returns, it grows to $40; that same $10 sold and taxed then reinvested elsewhere yields only $28 at 4x, a 40% difference. Beyond mathematics, rollover signals genuine belief in the business's prospects - both to PE investors and internally. It also removes concentration risk from family net worth, allowing founders to take prudent risks and play offense rather than defense. Board seats and minority shareholder rights follow meaningful reinvestment, enabling founders to participate in follow-on capital raises. Sean Mooney stresses the psychological shift: founders who've monetized enough capital sleep better at night and commit harder to aggressive growth plans. Bankers often push for lower rollover percentages, but PE firms consistently reward meaningful founder reinvestment with higher valuations and better terms, recognizing that skin in the game drives execution.

Key takeaways

  • →Rollover equity allows sellers to keep 25-50% ownership in the post-deal entity while getting liquidity on the majority stake, with the retained portion structured as tax-free equity exchange that compounds at the full investment basis.
  • →Tax deferral on rollover equity creates substantial long-term wealth: a $10 rollover at 4x returns yields $40 versus $28 for a taxed-and-reinvested alternative, a 40% difference that can result in founders making more on the rollover than the original sale.
  • →Meaningful founder reinvestment signals genuine belief in the business's growth prospects to PE investors, often resulting in higher valuations and deal premiums compared to minimal rollover situations.
  • →Removing concentrated net worth from the balance sheet allows founders to psychologically shift from defensive, risk-averse management to offensive growth mode, committing harder to the PE firm's value creation strategy.
  • →Board representation and minority shareholder rights tied to meaningful rollover give founders governance participation and pro-rata rights in follow-on capital raises, preserving ownership percentage as the business grows.

In this episode

  1. 1Introduction to Rollover Equity in Private Equity
  2. 2Tax Efficiency and Financial Benefits of Rolling Over Equity
  3. 3Alignment and Signaling: Why PE Firms Value Rollover
  4. 4Governance Rights and Board Representation for Rollover Investors
  5. 5Risk Management and the Psychology of Business Ownership
  6. 6Signaling Effects: What Rollover Percentages Communicate to Capital Partners

Mentioned

Lloyd MetzDoug McCormickSean MooneyHCI Equity PartnersICV PartnersBlueWave

Guests

Doug McCormickLloyd Metz

Topics in this episode

Family business successionlower middle market PEValue creation playbookRollover equityTax-free equity exchangeSignaling and alignmentFounder reinvestmentBoard representationMinority shareholder rightsFollow-on capital raises

Questions this episode answers

What is rollover equity and how does it work structurally in a PE transaction?

Rollover equity means a seller retains an ownership stake (typically 25-50%) in the business after a PE firm acquires a majority stake. The retained equity is structured as a tax-free exchange rather than a cash sale, allowing the owner to participate in future value creation without immediate tax consequences on that portion.

Why do PE investors prefer founders who roll over meaningful equity?

PE firms value rollover equity because it signals the founder genuinely believes in the business's prospects and creates alignment with the PE firm's growth plan. Founders with skin in the game are more committed to executing value creation strategies and make daily decisions with equity upside in mind, reducing the risk of misalignment between PE and management.

What is the tax advantage of rolling over equity instead of selling everything and reinvesting?

Rolling over equity defers taxes on that portion, allowing it to compound on a larger base. If a $10 rollover investment grows at 4x to reach $40, selling and reinvesting that same $10 after taxes yields only $28 at 4x due to immediate tax drag, creating a 40% wealth difference over time.

Can founders who roll over equity get board representation and governance rights?

Yes, meaningful rollover investors typically receive board representation, minority shareholder rights, and the ability to participate in follow-on capital raises to maintain their ownership percentage as the business grows.

How does rollover equity help solve the 'defense versus offense' problem in family businesses?

Taking liquidity off the table relieves the psychological pressure of having most personal net worth concentrated in a single illiquid asset, allowing founders to shift from risk-averse defensive management to aggressive growth offense and feel comfortable taking prudent risks.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

14 / 20

The episode provides substantive, practitioner-grounded insights on rollover mechanics, tax efficiency, and alignment incentives that a B2B operator unfamiliar with PE would learn from. However, much of the content is explained at a conceptual level rather than densely packed with novel claims - concepts like alignment, signaling, and tax deferral are discussed repeatedly without introducing fundamentally new frameworks. The discussion of junior-level equity education challenges adds fresh dimension but represents a smaller portion of runtime.

So the tax deferral and then the incremental compounding that you get in a good outcome, it really is powerful. And people often say if these situations perform well through a combination of leverage and growth, you can make more on your rollover than you did on the initial sale.
We haven't gotten it perfect yet, but we're still working at it.

Originality

12 / 20

The episode covers well-known PE concepts - rollover equity, alignment, signaling - without introducing contrarian or first-principles thinking. The framing is conventional within PE circles. The one novel angle is the discussion of education failures around junior-level equity incentives and the timing of belief formation, but this remains somewhat underdeveloped. Mostly the conversation validates and reinforces existing PE orthodoxy rather than challenging it.

Equity is the one instrument where we're absolutely 100% aligned.
It's the right thing to do. It aligns incentives, it doesn't sell false signals.

Guest Caliber

16 / 20

All three speakers - Lloyd (host), Doug McCormick, and Sean Mooney - appear to be active, hands-on lower middle market PE practitioners with relevant deal experience. They speak from direct involvement in structuring and closing transactions, not from sideline observation. Doug and Lloyd operate as partners doing deals; Sean provides multi-year personal case study. However, no biographical confirmation is provided in the transcript itself, so caliber is inferred from speech patterns and specificity rather than stated credentials.

Doug McCormick and Sean Mooney. Together we'll navigate the corridors of private equity, revealing the uncommon knowledge, challenges, successes and lessons that drive the world of private equity and business forward.
my whole career, nearly 20 years in P.E. that was ingrained. The power of this alignment and rolling over it.

Specificity & Evidence

11 / 20

While the episode contains some concrete examples (pool cleaning platform, $10 → $40 vs. $10 → $7 → $28 math model, 80 - 90% liquidity scenarios), it lacks named companies, real deal numbers, exit multiples, or timelines. The tax math example is illustrative but generic. Most claims are stated in categorical terms ("we've seen situations," "many deals") rather than grounded in specific case data. Personal anecdotes from Sean (90% rollover, college funding) add specificity but remain singular.

So let's just do a real quick scenario. Say you had $10 that you're going to reinvest in the business or rollover. And if you just roll over 10, and let's say we do four times our money, so 10 turns into 40.
I rolled north of 90% of what I had in this new one.

Conversational Craft

13 / 20

The hosts ask clarifying follow-ups and dig into mechanics (e.g., 'does the owner have to sell stock or assets?', 'what are red flags?'), and Lloyd pushes back gently on complacency around signaling effects. However, the conversation rarely reaches genuine disagreement or tough questioning. Answers are long and monological; few moments where the host interrupts to probe a soft claim or challenge an assumption. The tone is collegial to the point of lacking edge. Sean occasionally personalizes discussion effectively, but overall the dialogue prioritizes narrative flow over adversarial rigor.

But I want 80% of my value cashed out today, and I'm only going to roll over a little bit. Like, those are super inconsistent. But that kind of presentation happens really often, and it's super telling.
So in the first case I want to hug that leadership team and I, uh, walk away from the second one. Why you just don't believe you couldn't send a more clear signal that you don't believe in the future prospects of this business.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A37%
  • Speaker C32%
  • Speaker B31%

Most-used words

equity64team25private24family22value22point21doug20rollover19part18money15roll15partner14leadership14risk13seen12signaling12

Episode notes

Doug McCormick, Managing Partner at HCI Equity Partners , and Lloyd Metz, Partner at ICV Partners , join BluWave’s Sean Mooney to explain why rollover equity sits at the center of private equity dealmaking. They break down the mechanics, tax advantages, and alignment dynamics that allow founders to take liquidity while remaining invested in future growth. The discussion also explores signaling, governance rights, and why investors pay close attention to how much an owner chooses to reinvest. If you want to understand why rollover equity drives many of the best outcomes in private equity, hit play.

Full transcript

45 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign.

Speaker B: Get ready to peer behind the curtain of the private equity universe with each episode of Best But Never Final. Hi, I'm Lloyd Metz, joined by Doug McCormick and Sean Mooney. Together we'll navigate the corridors of private equity, revealing the uncommon knowledge, challenges, successes and lessons that drive the world of private equity and business forward. Let's go.

Speaker A: It is great to be back with Lloyd and Doug. Doug and Lloyd, how are you?

Speaker C: Good man, good man.

Speaker A: How are you doing? Great. It's always a good time. We get to pull ourselves out of the craze of the days and then talk about fun subjects like rolling over equity into transactions. What do you think about that?

Speaker C: Nothing more exciting here on a Friday afternoon.

Speaker A: That's what Lloyd lives for, is talking about rollover equity on a Friday.

Speaker B: What else would you want to talk about? This is exciting stuff. This is actually super exciting.

Speaker A: It is as exciting as it sounds because it really actually is. It's something that, uh, makes the world go round and round in lower middle market private equity in particular. And it's a way that multiple people win. And who doesn't like the more button? We've all seen that commercial. Again, let's just all get more. Why don't we jump into that if that sounds good to you guys?

Speaker B: Absolutely. Let's do it.

Speaker C: Let's do it.

Speaker A: All right, Doug, uh, kick us off when we say rollover equity for people who aren't in the PE world, what is that, first of all? And why should owners want to do this?

Speaker C: Why not? Let's start there. So first of all, what is rollover equity? So essentially, if you're thinking about selling your business, it's simply keeping a stake in the business on a go forward basis. So oftentimes Lloyd and I are dealing in a lower middle market where we're buying founder and family owned businesses in many cases. And so as part of that transaction, we would often buy a, uh, majority and the family may keep partial ownership interest. So why is that interesting? Well, first of all, private equity is generally a high return asset class. And so you're always asking yourself, what am I going to do with the money once I sell the business? And so here's a good alternative in general, but I think there's a bunch of other reasons, right? You know this asset super well. You've lived with it, you've owned it. So you have a very good perspective on the risks and the opportunities, probably more than any other asset or investment that you could choose to make. Now, if you're rolling over, it presumes you think your partner is competent and you believe in the strategy. But in many cases when guys like Lloyd and I are getting involved, there's because there's a specific strategy about how you're going to create outsized value. And so whether it's a growth strategy around, you know, a new product or a new geography, or it's a consolidation strategy, you have the opportunity to avail yourself to that. In many cases you should think about when people take our investment, they're looking to realize a uh, significant value creation opportunity or they're looking to diversify their assets. And rolling over allows you to do that. You've sold a majority, you can deploy that money in a variety of different assets and this is the portion that you remain concentrated. And I think the last financial benefit is it's super tax efficient. And what I mean by that is if you sell the entire asset, you're going to take all that money, you're going to pay tax and then you're going to invest in. It's going to compound on that reduced number. Whatever I roll over, you can generally structure it in a way that's tax free and that allows me to compound that bigger number. So it's like staying in the game with maximum dollars at work. One more point I'd make is there's a soft benefit. And that is, I think it gives the owners a chance to be a heads up partner. And I think there is a different feeling when you got skin in the game and the ability to kind of speak as an equity holder. And I think a lot of entrepreneurs who are used to being in charge kind of like that. So there lots of different reasons on why this is very prevalent in our part of the market.

Speaker B: And Doug, uh, can you say a little more? What is it maybe that uh, guys like you and me, why do we like rollover? Why do we offer rollover? Why do we like to see leaders of businesses rollover equity?

Speaker C: Yeah, two big reasons. One is I do think there's a valuable signaling element here. Right. Like it says, I've, uh, agreed to purchase your business at a fair value and it's a fair value that the seller still believes the prospects for the business are really good. And I think the other thing is in many cases, listen, we are relying on these management teams to drive the value creation playbook. And we want them to be aligned in a way that they're willing to work hard and be committed and stay involved and stay invested emotionally as well as financially to go make those things happen that we all think are possible. So that alignment is super important and powerful.

Speaker B: The alignment part, you can't emphasize more how important that is. Right? Because you definitely don't want, as we've talked about in other episodes, you don't want any gap between what we think is possible, what the founder, the CEO, family member, leader thinks is possible. They have ambitions and aspirations to double or triple the size of the business. We're there to help them achieve that. Uh, you got to remember the starting point. And so they need to benefit and gain from getting that growth dream realized as much as we do. Like, you can't have a us versus them dynamic. You can't have a leader of a business thinking that they work for the private equity firm. So you absolutely want to them to benefit as much and in some cases you can set it up, they can benefit even more than we do if we hit the plans, if we grow as dramatically as we all think we can. That last point, Doug, I think is super critical.

Speaker A: Let's plan on digging into that a little bit more because I think it's important. That's the name of the game, right? It creates alignment. And for our listeners, one of the things that you'll hear probably from the private equity professionals or friends who are not, they'll talk about this being the second bite of the apple. As the person on this podcast who is the jargon person, I'll let you know that's what you're going to hear. But before we go about my metaphors and cliches, let's maybe drill down first a little bit, just about the mechanics. So when we say rolling over, does that mean the owner has to sell their stock or the assets of their company, pay their taxes, and then buy it back in after taxes? Or are there ways around that so that they can get favorable treatment and defer that day till later?

Speaker B: You pay taxes on the part that you sell and get cash for at a very high level, simple way that that's hard to avoid. The part of rollover is the part that you're not selling. And so you're exchanging equity in your business that you currently own for equity in the new entity that the private equity firm sets up. And so that exchange of equity for equity is tax free, just at a very high level, simple explanation. And so there's opportunity for that leadership team, that leader, their family members, whoever is in the current business who wants to continue on in the new private equity backed journey to own 25%, 30%, 40%, close to 50%, depending on how you cut the deal. With your private equity partner, you own that much of the go forward equity of the new business. So to Doug's earlier point, it gives that leadership team an opportunity to benefit from the growth plans as much as the private equity firm. And given that they're going to be running the business, Doug, I think you said it very well. Like we're relying on that leadership team to execute and drive the business. Those hour to hour, day to day, week to week, month to month decisions, they're going to think about it differently if they own a material amount of equity. There's the idea that there's our expectation that they're going to make decisions that benefit the equity value and the equity shareholders and all of those little decisions that add up to the bigger decisions and add up to the ultimate results. They're going to keep that in mind

Speaker A: as we drill further down on structure. So the good news is your seller business, you get to a monetize the majority of your ownership in a company, get real money to take that stress off your shoulders. You will have to pay taxes on the part that you sell. Now if we drill down further on that true or false, is it better to live in Tennessee or New York, Maryland or Virginia?

Speaker B: Hey, hey, hey, wait, I'm not gonna touch that.

Speaker A: Wait a minute, where do I live?

Speaker B: Oh, wait, I live in Tennessee or Nevada or Texas. Yeah, yeah.

Speaker A: Now the ultimate is Puerto Rico, which I haven't gone that far yet.

Speaker C: Sean, I appreciate you really rubbing that

Speaker B: just for our listeners. It's interesting where some of this applies. And Doug, uh, you've probably seen it. Sometimes it's a family owned business. So Sean, you ah, are the leader of this business and you have siblings and maybe you have an um, aunt or uncle. They want 100% liquidity. You kind of don't. Right? So in total we're talking about the family needs to roll over. But it's best if it's the active participants in the business who are leaving money into the company, who have continuing equity interest in the company. If it's your older brother and older sister who aren't involved in the business and it's your uncle, your dad, who is the founder's brother, well, we can cash them out because they're not important to the business or they're not active in the business. And oftentimes rollover is helping to bridge those kind of dynamics.

Speaker C: And just to uh, do some real quick math because I think the power of this tax efficiency is really interesting. So let's just do a real quick scenario. Say you had $10 that you're going to reinvest in the business or rollover. And if you just roll over 10, and let's say we do four times our money, so 10 turns into 40. If you sold that and invested it somewhere else, your 10 turns into seven. So your four times is 28. Right. So the difference between $40 and $28, 40%. So the tax deferral and then the incremental compounding that you get in a good outcome, it really is powerful. And people often say if these situations perform well through a combination of leverage and growth, you can make more on your rollover than you did on the initial sale. And that model I've seen manifest itself a number of times. And so it's kind of the gift that keeps on giving.

Speaker A: I think that's a great point. And that's that whole second bite of the apple thing where how many times have each of you seen that where the owner or the person who rolled in made more than the original transaction, in many cases by significant numbers. And maybe we'll talk about next, maybe how that alignment supports that case, but it gives you this opportunity to really get some of that risk off their shoulders. Maybe align, we'll talk about, align the shareholders within a large family business where the operators are solely involved in the next ownership. What about for those who roll over if it's a family business or whomever, if there's one big holder, if you will, what do they also get if they've rolled over a substantial amount in terms of governance versus maybe a family seller where the CEO may continue, but they've sold every dollar of their equity.

Speaker C: If a management team or uh, a seller is meaningfully reinvesting, we would treat them like any other meaningful investor. So they often get board representation, they get minority shareholder rights, and that includes things like participation on new investments. And so they get to maintain their ownership percentage, which can be important, you're investing along the way. And so in good deals we're actively trying to get more exposure. And so this gives you a chance to preserve your equity along the course. I think those are the two biggies, minority rights, board representation. And I think the big one on minority rights is just the ability to participate along the way.

Speaker B: I think you got that 100% right, Doug. Part of the other benefit is, and again, it depends on the circumstance and how much people decide to roll over and how much people decide to liquidate. But I've seen situations where taking that very, very concentrated personal or family net worth tension off the TABLE so they've literally put enough money in cash and liquid investment somewhere in the bank or an investment firm for their family. Whether it's college aspirations or whatever their family objectives are, they've got enough that they're now comfortable taking more risk. Actually they literally personally at the job, working at the company are more comfortable opening up the playbook and taking more risk. It's actually pretty cool to see. And so when you find the right person and they roll over the right amount, you kind of see that dynamic play out and it's really cool to see.

Speaker A: This episode is brought to you today by HCI Equity Partners, a lower middle market private equity firm focused on partnering with family and founder owned manufacturing, service and distribution companies. ICV Partners, an innovative private equity firm supporting management teams of leading companies at the lower end of the middle market. And bluewave, the business builders network, connecting the most proactive business builders in the world with the best of the best service providers for uh, critical variable on point and on time, due diligence and value creation needs. Now back to the episode. I think that's so spot on. That's always, I always thought about we'll do sessions with new team members who join and I'll share kind of like the history of the private equity industry. In large part they created a segment that didn't exist. But one of the things that I think business owners feel, and if you can talk about this more, is that once something becomes worth a lot of money, you start playing defense and then what happens, Doug? Uh, you can maybe talk about when you watch like the army football team start playing defense and not offense, what happens to the score?

Speaker C: It stays low.

Speaker A: But like any sports team that we all like now, I'm a Cleveland Browns fan so I don't know what it's like to have a leaf and so, but I've seen other teams when they have leads, but inevitably psychologically losses way more than gains and then the companies start playing defense and then if you're able to take some off the table, then suddenly you can go to sleep at night. But then you keep them on in, you're playing for the future as well. So talk about that some more about how that defense versus offense and how you kind of almost reinvigorate yourself.

Speaker C: I think there are two aspects of what you're getting at. The first is fundamentally I think private equity is solving one of two things. It's solving the succession planning need to help finance generational transfer or it's bringing growth capital to the table where they can Execute on a strategy. And to your point, if this asset is the majority of the family's net worth, you've got to manage that asset in a way that's pretty low risk or risk adjusted, relatively secure. And so you're also consuming the family, spending the money to live a normal life. And so this allows you to kind of take the money off the table. And to your point, this becomes, quote, your equity portion of your broad portfolio, and you can really kind of make some meaningful moves and take some risk. But prudent risk in the context of a diversified portfolio.

Speaker B: Now, that dynamic is 100% true. And I don't know about you, Doug, but for us, we often are trying to figure that out in our diligence or in our pre diligence. Getting to know a, uh, leadership team, an entrepreneur, trying to get in between their ears to figure out how are they thinking about things. Because rarely, at least in my experience, maybe folks are more forthcoming with you, Doug. Rarely do people share what they're thinking and feeling as it relates to what this transaction means, how they're thinking about it, what are the other factors that are affecting their decision to transact, for sure.

Speaker C: And that's why I, uh, think actions often speak louder than words. And we circle back to this whole concept of there's a big signaling aspect of what reinvestment means from our seat, where we get to evaluate the business and do all the diligence and do our work. And then we get to also say these guys are acting in a way that's consistent with the underwriting. So I think that's super, super powerful.

Speaker B: Absolutely.

Speaker A: I'll even personalize it. My whole career, nearly 20 years in P.E. that was ingrained. The power of this alignment and rolling over it. And you could see family business after family business, kind of like fighting the risk and playing it safe. And in the earlier days of their businesses, they're all gas, no breaks, and just creating tons and tons of value. Then it starts being worth something. Even though I knew that for the vast majority of my professional career, I started feeling that here at Blue Wave, where it's just like, every day I'm like, oh, my God, this thing is worth something now. Like, what if I screw it up? I would constantly have to hold myself accountable, saying, like, don't screw it up. Don't screw it up. Be safe. And I think every business owner feels it, but I never knew what it really felt like being on the other side. And then we brought in some capital, and I took a, uh, modest amount off as far as a minority equity investor that came in. But really, as much as anything, just for my wife, it was great because she's like, uh, all right, dude, if you get hit by a bus, at least college is paid for.

Speaker C: Well, and good chances. She knew you were going to screw it up.

Speaker B: Yeah,

Speaker A: she's still giving me time, too. This is very true. So she's like one of two ways. You take a little bit off or you double your insurance. I think it was more of an. And wait a minute. No, actually, somehow amazingly, I've been able to double down on this thing for nine years. But to your point, it's like, that's in everyone's mind. What if I screw this up? The vast majority of my net worth is in this thing, and it's all on paper.

Speaker B: So you've lived this, John. You've lived this. Yeah. You get it.

Speaker A: Yeah. The differences on this one versus maybe the next one is that I rolled north of 90% of what I had in this new one. And we'll talk a little bit about what that signals to the investors and what it does in other ways that does create a huge amount of alignment because I'm still like, the vast majority of what I have is in this business. So every day I wake up like, oh, God, I started zero. Let's go.

Speaker C: One comment on your specific situation. So we've all talked about how there's an important signaling aspect here, but in some cases, it's not a perfect signaling aspect. In many deals that Lloyd and I do, because we're still providing 80, maybe even 85, 90% liquidity in your situation, there is no way that you could do that deal without believing in it. Right. Because there's no basis on bringing in capital and keeping 90% where you don't think that's a good outcome for your own investment. Right. So you couldn't take enough off to make that make sense.

Speaker A: I think that's exactly right. You have to really believe in it. And I also, to be candid, I also have a pretty good vision of how we're going to get to the next spot. In large part, I think through the grace of having been in your industry for so many years, that I just learned a lot about the next road ahead. But so many people I can imagine if I didn't go on that path, I would really want to partner where I'd say, I don't know how to get it there. And don't take this as I really know how to get it there. I have strong hypotheses And I guarantee you, uh, to your point, I'll screw it up probably two times a day, but I'll go left and right really quickly. But to your point, I think it also says a lot of people if you didn't get to see that movie over and over again, it really behooves to also bring in a partner. And so talk about now you've got an owner who's rolled in, and then maybe, what are the benefits of now that the risk is off their shoulders? They've got fuel, they've got a partner to show them the way, and then maybe they've got less noise from the family. We all know family businesses can be amazing, but there's also tough elements of it.

Speaker B: I just want to go back before we jump into this. I think the piece that Doug was raising about your specific decision to roll over, whatever, 90% of your value and take a minority investor relative to the control buyouts that Doug and I do and that many private equity firms do, the nuances of signaling do differ. I just want to take a little time and talk about signaling, though, because I'm consistently surprised at how many CEOs, business leaders of the companies we look at don't really think about the signaling effects when they say, we think this business is about to hit an inflection point and it's going to double in size in three, four, five years. And with your help, we can triple it in size. But I want 80% of my value cashed out today, and I'm only going to roll over a little bit. Like, those are super inconsistent. But that kind of presentation happens really often, and it's super telling. And so for any business owners or entrepreneurs who might be listening to this episode, just be mindful of that. You don't listen to your advisors if you've hired bankers or brokers or what have you, because they will try to get that rollover number lower. But the signaling affects your capital partner. It gets you off on the wrong foot.

Speaker C: I think I agree with you, and I'll even be a little more explicit. I think people actually will lean in on value more. If you're putting skin in the game with you in a way that your 20% didn't cost 20%. I think people will stretch in a way to say, I was going to pay X, this guy's going to be a partner with me. And I'm willing to lean into that because I value that alignment of incentives in the signaling.

Speaker A: What does it tell each of you? Maybe we'll do like the binaries. And you've got, uh, in the extremes of what's possible in a buyout. So you have an owner that says, hey, I want to bring in a partner, I want to get some liquidity, but I want to roll, I want to roll 49% or have 49% as much as I can roll to get 49% of the ownership afterwards versus the person who says, I don't want to roll anything. Maybe I'll roll 1 to 2% over. What goes through your mind when you see that and the banker tells you about that for the first time.

Speaker B: So in the first case I want to hug that leadership team and I, uh, walk away from the second one. Why you just don't believe you couldn't send a more clear signal that you don't believe in the future prospects of this business.

Speaker C: So in the first one, where there's this meaningful reinvest, you don't have to underrate what they believe, you're underwriting what they believe to be true. And in the second one, you're underwriting do they believe and you're underwriting whatever the base case is. So obviously that's a, uh, slightly more difficult underwriting. I will say I've had situations where like we bought 100% of the business and there were reasons that made total sense. Sometimes it's an estate issue. Sometimes it's a really significant older founder who has said, I need to be fully retired. We have done deals where we've cashed people out 100% but I think the circumstances have to be reasonable in the context of like, why they're doing it

Speaker B: and in the case, Doug, with the older founder who wants to be cashed out entirely, how do you set it up such that the go forward team can benefit from equity other than the incentive equity grant, have you ever cut a deal with the, uh, founder to say, hey, gift or grant some portion of your current equity to the leadership team for them to roll over?

Speaker C: The situation where I find, uh, this coming up the most is when we're doing a consolidation platform. I've already got my platform and I'm working with entrepreneurs where they're a small piece of a bigger business now and they're not maybe a senior part of the new team and they want a hundred percent liquidity. And at that point I kind of say I've got a business to scale with competent managers and I know the business well enough and I can act like a strategic in a way that I can buy them out 100%. And feel pretty confident about being able to manage the outcome and underwrite effectively. So I'd say that's the most common scenario where I found that got uh, it.

Speaker A: Let's drill down further because I think this is a really important like what are the red flags for business owners? And that signals that they may not even know they're sending. And they say, I don't want to roll anything over. You know, I want to be a CEO just as options in the business, just like if you had hired me outside of it. And so what goes through your fear? You buy this business and it's a multi part of a multi location platform. We'll say it's pool cleaning, something like, oh, you're doing a new platform and pool cleaning. And this person says, I want to sell everything. And they are kind of the company. What goes through your mind about what are the bad things that could happen? Are they signaling immediately one day after close?

Speaker B: Well, a big part of it is. And again, this is also part of what you try to suss out as you get to know a company's leadership team, the CEO and diligence. You're trying to figure out is this transaction going to result in enough money in terms of proceeds, net of rollover, where that person, if things don't go to plan, if things go south actually and get bad, where they can walk away and they're perfectly happy with their proceeds in the bank and their lifestyle won't be impaired, they can literally just walk away and go do whatever they want to do next. You're trying to figure that out.

Speaker A: Yeah, that was always my fear is like, okay, they're going to move to Florida. They got all the sales relationships. They're like the fabric of the business. And they were so fundamental to the story of the business. And then one day later they're out and then you're left without all of this historic knowledge, the leadership. And all of that's risk. Right. And if risk goes up, you mentioned earlier, price goes down. And so these sellers are signaling things to buyers of companies that they might not even appreciate that they're doing. But professional buyers all have scars and wounds from um, countless, countless cycles of these things. At least I did.

Speaker B: Now Doug, you do raise an interesting distinction between this dynamic with a platform company versus an add on. I agree with you. An add on. The dynamic changes. If you need that leadership team to drive the new product line that you're acquiring or the new geography or service line that you're acquiring, that's different than necessarily I Need a platform, I need a partner. I need you to stick with me to get this investment thesis off the ground and to completion like you would with a, uh, platform. So I appreciate you raising that distinction.

Speaker C: Yeah. And I think there's one other aspect here which is I think we're always trying to evaluate not only is it a deal that we like, but is it worth our time to get there. And I think when you have a partner, two things happen. One, you get a pretty good sense of is there good chemistry and are you well positioned to win because they really like, they like you or they value you for uh, your skill set or expertise in what you're about to do. And the second thing is this is not just a negotiation around price. There's all kinds of terms and conditions and indemnities and things that we're going to have to navigate. And if you've got somebody that's got a significant reinvestment, I think it ends up being more of a I'm negotiating a partnership document versus I'm doing a transaction that I'll never see the seller or the buyer again. It's much easier to navigate and therefore higher probability close.

Speaker A: So someone one time taught me this great term. It was called selfish altruism. And it's that you're doing the right thing, hopefully because it's the right thing. But often doing the right thing is selfishly good for you. One of the things that I think about rollover, it's the right thing to do. It aligns incentives, it doesn't sell false signals. It gets people the opportunity to have liquidity, but then also the fuel and the reinvigoration to build something even better. For both sides though, I think there's a lot of selfish altruism. And for the PE firm you get to get good outcomes for your own investors. B, you get create in some ways super life changing outcomes for the partner at uh, the business that you're creating. C, it's the CEO of that family business then gets to go and realize their full self. Not only generate income, but then kind of build their own legend and their team's legend. Talk about these other side benefits that come that serve the long term benefit of not only the IRRs and MOICs but but also just these more subjective benefits. The things it does for your own firms. When you have these stories again and again and the investors themselves, what they're able to do and what the CEOs are able to do.

Speaker C: I totally agree. I feel like some of my best investors are people that I've partnered with historically, where we had a chance to work together, we had a good outcome, they've created some wealth, they've seen the quality of the organization through an entire deal cycle because there's no better diligence. Right. They understand how we're going to prosecute and how we're going to compete in the marketplace. We've had super good experience there. And talk about great references. They can speak to the goods and the bads and proof points on a

Speaker B: great outcome that reference uh, that halo effect of successful outcomes. And you can speak to the CEO or whatever member of the executive team as what does the private equity firm like to work with from an executive perspective? But you can also speak to them like Doug, you're mentioning you had money up with them, how did it turn out? And how do you feel about their commercial skill as investors? Right. So those can be two separate conversations that these people can address. And I, uh, may be in the minority here, but I'll also say it feels good at least for me to see an entrepreneur express their ambition, where they want to take this business. We come and help them get there and to see them achieve it and to have created wealth for themselves and the people that they have on their team who are having six figure and seven figure outcomes, that actually feels good to me and maybe some other of my private equity colleagues feel good when you see that happen. And so that is selfish altruism in many respects. We want them to do well and when they do well, we do well. And I'll even take it a step further. At our firm we often provide some structures that juice up the rolled over investment, matching loans and other structural elements that can double up or if you want, triple up the rolled over amount so that you can have equity participation further down into the leadership ranks, down to the supervisor level if you want, where people are putting up five figures and have the chance to turn into six figures if things work out well. So we don't mind people making a larger multiple of their rollover or their money that they write a check for than us. We don't mind that at all actually.

Speaker A: I think that's amazing and it's very well said. Have you all also, once you realize the future that they can become, have you ever invited these uh, business owners, rollover partners, to participate in your own PE funds afterwards?

Speaker B: Yes. The CEO of our uh, firm's very first investment is an lp. He loves coming to the annual meetings and asking questions. After all those years where we were

Speaker A: asking him questions Sometimes the shoes on the other foot, I guess.

Speaker B: Oh yeah, absolutely. And he's loving it. Yeah.

Speaker C: Be careful what you wish for. Right.

Speaker A: Keeps on mentioning this thing called DPI or something, I don't know. But that was the other thing, but I think is a good thing is they do well. And that was one of the most powerful things we would do is we would invite them into the fund. Really frankly, pretty advantageous terms. And then to your point is then they become almost like this sage council that you can bring in for the next deals and talk to them about it because they've seen it, they've done it. Not only are they an advocate in reference calls, but then they become part of almost like a peer or ah, a limited partner who's backing you. And that whole kind of circle of trust, the karma wheel kind of spins and spins.

Speaker B: Yeah. Now, uh, I have a question for Sean and Doug. We've talked in other episodes about value creation. We've talked about portfolio operations colleagues. And what does value creation mean and the different aspects of it. How do you think rollover equity and making sure the team has enough equity, how does that actually come into play when you are talking about a value creation plan and the execution of it? How does that make a difference?

Speaker C: Candidly, I think it's really tough to operationalize the difference, but I fundamentally believe that it results in a, uh, positive impact simply because you have direct line alignment of incentives and not only risk of gain, but risk of loss, which I think is more appropriately balanced. And you know, listen, equity is the one instrument where we're absolutely 100% aligned. And you know, a lot of incentive programs are not perfectly aligned as much as you try. Right. If you have KPIs for the guy who's on the shop floor, that's related to, you know, throughput on a weekly basis, that may not translate into profitability or equity value. And annual budgets based on profitability for the year have nothing to do with end state equity value. It's simply, uh, interim measurement, period. So to me it is the ultimate everybody on equal footing. We're paying directly for the outcome we're most desirous of incenting.

Speaker A: That's spot on. And when I think about it personally, one my own rollover into this transaction, one, I'm highly incented or incentivized, whatever the incorrect term is, to work really, really hard. And the vast majority of my net worth is tied to the success and failure of our team. And so I have high incentives. And frankly, I'm fortunate because we Brought in great investors who are great partners, and I frankly probably didn't do it soon enough. And that I really am benefiting from their partnership and having another ear and another set of perspectives to help us make better decisions faster. And so we really are benefiting from that. And they bring a lot in that regard. So we're fortunate with that. And then I think the second part of it, and this is something we've done from day one, just from the private equity way, is push equity down into our organization to inspire our, uh, team members to think and act like owners. And what I'd say is it's kind of a mixed bag. The leadership team people, and ultimately people who either became on the leadership team or recruited in, were people who truly demonstrated their ability to think and act as owners and truly value that equity. And I'll tell you, there are people who are not in an organization who didn't value that and they're no longer with us. And so for me that's a huge signal, uh, of like, can they be here on this run, not only where we are today, but tomorrow? Because they can think of and worry and get as excited about the multiplying effect of equity as much as I can. And then where it's been more mixed, I think is on the junior level, people where they don't really understand it. And maybe that goes to us for not explaining it as much. I am always shocked when there is natural, either, uh, unplanned or as much as often the not planned turnover, how seldom the options get exercised. And that's just extremely candid and probably more candid than most people want to hear. I am kind of surprised by that part of it in ways that I didn't think would be the way it happened. Does that resonate with you all?

Speaker B: It does. And we're starting to talk about incentive equity versus the bought equity or rollover equity. We're still trying to fine tune how to make that incentive equity, whether it's profits, interest or stock options, to make it easier to understand and therefore perceived as valuable with lower middle market companies. We haven't gotten it perfect yet, but we're still working at it.

Speaker C: So, Lloyd, for what it's worth, I think it's a really interesting point. And it's less about structure and more about education. Right. Because we all are pretty familiar with it and have seen the power of it. And I think in many cases the challenge with these equity incentive programs is it's really powerful once somebody's experienced it once. Right. And I've seen this scenario where we have a great outcome and at the end, these people get paid and the light goes on at the end. And they didn't see the power of the program until the very end, which is totally inconsistent with the intent. So I think, uh, education's key here.

Speaker B: It is. And you remind me of occasions where when we've gotten to a, uh, successful exit, you hear people say, I wish I'd bought more. I wish I'd rolled over more. To exactly your point. It seems theoretical to them when you're talking to them and inviting them. And I think you can sketch out what it might look like, but when it actually happens, people are like, doggone it, I messed that one up.

Speaker C: I think it's interesting, Lloyd. I think we need to do a better job of when we're upfront in investment, of talking about what it means to my partnership. So we're in there going, okay, so we're buying your business, by the way, we're 3% or 5% of the capital of the fund. And so that means we personally have this kind of investment in your business. We believe in it, we expect it to do this. And this is how it translates for you because I think not only is it an education issue, but it's a credibility issue because you're coming in on the front end, they don't know you from Adam, and you're saying, this is going to be a great deal, we're going to do three times our money. But they don't necessarily believe you or they don't have reason to have trust in you yet. And so I think some of this is where the commitment comes at a stage in the relationship that's relatively immature.

Speaker B: And to that point, and, uh, you articulate it beautifully, we have generally kept the door open for the leadership team to buy equity. We usually keep that door open after close because to your point, oftentimes after the first year, they get to know us as private equity investors and as people, so they're not as scared as they might have been pre and shortly after close, they start to see that some of these crazy ideas actually are working. And so oftentimes a year in, people will come knocking on the doors like, can we buy more? And a group of employees or a group of the c, uh, suite or whatever it is, have six figure dollars that they've cobbled together to put into the company. And we're always accepting that. We never turn that away because of the positive signaling effects that we talked about earlier. Right.

Speaker C: I'm with you. 100%. Except it's now 1.2 times your money.

Speaker B: Yes. Then you have to have that conversation. You have to have that conversation. But that's okay. That's okay.

Speaker C: No, I'm totally with it. One more point that I do think it gets back to an earlier point. We made many of these deals. There will be multiple investments during the life of the investment. And so it gives people the chance to say, I see it, I believe in it more now with a little bit of time of working together. And so on the next deal when they have their chance to participate pro rata, you see really good uptake on that.

Speaker B: That's right.

Speaker A: As I'm thinking through exactly what you're sharing, it's kind of a call to action to me. It's like I've got to do a better job explaining what this stuff is. The people who get it are those who've seen it before and they're usually this more senior level people and they don't get. It's kind of like everyone's from Missouri. It's the Show Me state. And so if you haven't seen it and you haven't spent the time teaching and teaching and teaching, it's hard to appreciate. And that's something that we're going to do better on. And I think a large part is just inspired by this conversation here. Just don't hold me to it. If our team members are listening to it. I'm just kidding. We're going to do a better job,

Speaker B: a continuous process to figure this out and get it right. Because we had an episode a little bit a uh, while ago. We talked about the American economy being very dynamic and uh, at the lower middle market, private equity firms are trying to spur innovation, trying to spur growth, trying to spur evolution in family owned businesses of which this country has millions of them. This is an important key to unlocking all of that talent, energy and creativity. When you find the right people, find the right partner and incent them the right way with rollover plus bought equity, broaden out the leadership team. Some pretty amazing companies can get built and some pretty amazing outcomes and wealth can be created. And that's a worthy pursuit.

Speaker C: Totally agree.

Speaker A: 100% all. Ah right. Gentlemen, this has been another awesome conversation about really one of the core concepts and flywheels of business and value creation and wealth creation in private equity and candidly probably the entire US economy now. So I really appreciate you all, uh, kind of pulling back the curtain and candidly sharing like here's how it works, here's why it works, what should be done, and here's some of the considerations that need to be made when doing it. So thank you once again Lloyd and Doug for sharing.

Speaker B: Thank you Sean.

Speaker C: Good discussion guys. A uh, special thanks to HCI Equity Partners, a lower middle market private equity firm focused on driving transformational growth through customers consolidation strategies by partnering with family and founder owned manufacturing services and distribution companies. Uh, learn more@hciequity.com ICV Partners, an innovative lower middle market private equity firm supporting management teams of leading companies at the lower end of the middle market. Learn more about icv@icvpartners.com and finally, Bluewave, the business builders Network connecting the most proactive business builders in the world with the best of the best service providers for critical variable, on point and on time, due diligence and value creation needs. Learn more about BlueWave@bluewave.uh net for further information on HCI, ICV and BlueWave and relevant topics discussed here in the episode, please see the episode notes or links.

Speaker A: The views and opinions expressed in this program are those of the individuals presenting and do not necessarily reflect the views or positions of any other persons or entities, including those referenced herein. No representations, warranties, financial, legal, tax or other advice are made herein. Consult your advisors regarding any topics discussed during this episode.

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