Private Equity Experience

High-Performance Teams vs Family Businesses in Private Equity

• Emily Sander • Season 1 • Episode 33

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In this episode, the hosts explore a fundamental question in Private Equity: should you build a high-performance team of top external talent, or rely on trusted family members to run the business? Through real-world stories, they unpack the trade-offs between trust, competence, and scalability– especially during high-stakes moments like PE transactions.

The conversation dives into the complexities of family dynamics, including trust gaps, role misalignment, and the emotional ties that can both strengthen and hinder performance. They also highlight how outside executives, especially in roles like Chief of Staff, can help bridge gaps and drive alignment.

Ultimately, the episode reveals that there’s no one-size-fits-all answer. The key is aligning the right people to the right roles at the right stage of the business, while balancing performance with trust to maximize long-term value.

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Who Are We?

Three insiders. One mic. All things private equity — explained. Hi 👋 We’re Ed, Rory, and Emily — a CEO, a CFO, and a Chief of Staff — here to demystify the world of private equity. Between us, we’ve sat in the founder’s chair, run PE‑backed companies, and worked on the deal side, so we know the wins, the pitfalls, and the jargon (and we’ll explain it).

Through the Private Equity Experience Podcast, our book On‑Ramp to Exit, and a library of free tools and templates, we share real‑world stories, practical strategies, and insider insights to help you navigate every stage of the PE journey — whether you’re leading a portfolio company, joining a deal team, considering PE, or just PE‑curious.

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Podcast Welcome

Welcome to the Private Equity Experience Podcast. Your backstage pass to the strategies, stories, and secrets that drive value in the PE universe. No filters, no fluff, just straight talk and expert insights to help you navigate the private equity world with confidence. And now your hosts, ed Barton, Rory Leaphart, and Emily Sander.

emily-sander_2_03-19-2026_134958

Today on the Private Equity Experience Podcast, we decided to talk about. The team makeup, and we're talking about high performance teams versus family business model. In our previous pods, we've talked a lot about efficiencies and getting the right people on board and staffing and growing that thing. Is that better suited toward finding the highest talent and the people best suited from external hires to do those roles? Or is it Hey man. It's all in the family. These are people I know. They're people I trust. They have my, they have my bloodline, they have my name. These are the people. Um, and we've got some stories from different, all different angles, but the, the first one, and maybe most the direct one, ed, is you've talked about your oldest daughter who has become, become a Nepo baby as you like to call her.

rory-randall-liebhart_2_03-19-2026_134959

Baby.

twinkle-toes--it-_2_03-19-2026_134958

she's the nepo baby.

rory-randall-liebhart_2_03-19-2026_134959

Oh my goodness.

twinkle-toes--it-_2_03-19-2026_134958

you know, I, and that was as much for me by necessity as anything. So I had a,

emily-sander_2_03-19-2026_134958

She saved your ass.

twinkle-toes--it-_2_03-19-2026_134958

yeah, I had an accounting manager leave on like the 31st of January. That was a primary TA was my tax manager for my clients. And so all of a sudden I'm like, okay, well I, you know, I, I

emily-sander_2_03-19-2026_134958

That's like the worst timing for tax season.

twinkle-toes--it-_2_03-19-2026_134958

Worse timing. Um,'cause you know, if I, so. You know, basically my daughter had gotten, um, she, she had gotten a back injury, um, could not continue to work where she was working, which required a lot of physical exertion. Um, and so she was outta work and I was like, okay, well, you know, you're coming to work. you know, you're going to do data entry for tax returns and spent, you know, a long weekend kind of teaching her how to do that. And she's been cranking along ever since. And, you know, kind of said, okay, well she's good with people. She, she likes people. She's a, she's a friendly kid. And so I've had her doing the phone calls, I've had her kind of setting some stuff up. We've got, part of our practice includes.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

planning and, and you know, kind of working with, uh, with founders and their families on how to position our assets. And so she's been, uh, she actually finds some of this stuff interesting. She's, she's learned, she's stuff I would never have expected, like she has taken to some of this incredibly well. Um, she was a out of necessity

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

well, you know, if I'm gonna have to. Pay her rent anyway. She might as well get, I might as well get something out of it. And so that was, that was part of the, the thought process. Um, but it is also, and, and, you know, you, you kind of touched on it, Emily, at the beginning. When I had an employee kind of leave me at the wrong moment, my immediate reaction was, I'm gonna hire somebody who, I don't have to worry

rory-randall-liebhart_2_03-19-2026_134959

Yes. Yes.

twinkle-toes--it-_2_03-19-2026_134958

be able to trust

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

do what I want'em to do. Now that may not be the best hire. As a matter of fact, I could tell you it probably wasn't the best hire, the smartest thing for me to do it. Be go find a. C-P-A-C-P-A candidate, they had, you know, five years tax experience and would be able to take a bunch of stuff off my plate, um, instead of me going, I'm gonna have to train somebody. But what I did know was, I know I've got a reliable, someone who's gonna do what I tell'em to do, um, for the next, you know, period of

rory-randall-liebhart_2_03-19-2026_134959

Totally.

twinkle-toes--it-_2_03-19-2026_134958

I'm

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

sure it's, see, to see how it goes. And she's got some skills. So it was a, know, it, it was a little bit of a necessity hire, but it was also a reactionary hire to. I just got, I just got left an lurch by a professional who had all the credentials and decided to take a better offer right at the edge of tax season as a tax person. And so, you know, leave me an lurch. I'm not gonna get left in the lurch again and let me bring on a kid

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

I

Standards for Family Hires

rory-randall-liebhart_2_03-19-2026_134959

Yep.

emily-sander_2_03-19-2026_134958

your heart of hearts, do you hold her to the same standard as everyone else on your team?

twinkle-toes--it-_2_03-19-2026_134958

higher,

emily-sander_2_03-19-2026_134958

Higher.

twinkle-toes--it-_2_03-19-2026_134958

higher. Hire,

rory-randall-liebhart_2_03-19-2026_134959

Okay.

twinkle-toes--it-_2_03-19-2026_134958

yeah,'cause I, so I've got some employees. For the most part, both of you have worked, have worked for

rory-randall-liebhart_2_03-19-2026_134959

Yes.

twinkle-toes--it-_2_03-19-2026_134958

I am, I tend not to be a real, like, come beat on you type

rory-randall-liebhart_2_03-19-2026_134959

No, no.

twinkle-toes--it-_2_03-19-2026_134958

right? I am very

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

wanna hire really good folks. I want'em to be self-managed. And if they're not, I tend to move them on. Um, but even then, it's probably, you know, 90 days later that I should have minimum. Um, with Julia, the first week she was here, she showed up late. And so I made her, I made her show up. And so she was supposed to be working from home the following week because it was her training week and I made her show up at the office at eight o'clock Monday morning.

emily-sander_2_03-19-2026_134958

That's right.

twinkle-toes--it-_2_03-19-2026_134958

an hour drive for her.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

she was gonna be, and if she hadn't showed up on time that day, she was gonna be here at Tuesday morning at 8:00 AM and she was gonna continue to be here until such time as she could figure out how to show up on time. you know, and I had a conversation with her that I would probably never have with a first, first week employee.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

so, and she's held to a higher standard. Now. Again, the flip side to that is when she's doing a really nice job, it, you know, kind of brings some tears to my eyes because I'm so proud of her and I generally don't get that with many

emily-sander_2_03-19-2026_134958

You're saying you don't cry for everyone else's good job.

twinkle-toes--it-_2_03-19-2026_134958

no. So, I mean, it's, it's, it, there's, but yeah, I actually hold her to a higher standard

rory-randall-liebhart_2_03-19-2026_134959

yeah,

twinkle-toes--it-_2_03-19-2026_134958

most of the rest of the

emily-sander_2_03-19-2026_134958

Gotcha. Gotcha. Very cool. I mean, we all have our stories, right? I mean the, we work for a number of companies and we'll, we'll. Save names for such time as, as later than this podcast. But, um,

rory-randall-liebhart_2_03-19-2026_134959

Off air.

Outsiders in Family Firms

emily-sander_2_03-19-2026_134958

but there's been like married couples and family kids who just should not be in certain roles. So that adds, that can add, I should say. It can work very well. It can also add some complications and complexity and different dynamics that you better be aware of if you don't wanna step on some landmines.

rory-randall-liebhart_2_03-19-2026_134959

that's, and that's the thing, you know, like. Working for a family business that has those dynamics as somebody that's an outsider, is a really interesting dynamic too, because you, you have to navigate the vagaries of the relationship amongst the family members, which isn't always like, you know, um, super seamless and, and harmonious in any way. So it's like, I, I find that interesting. You know, I think there's a human element of working for family business, I find intriguing, but it, it does. Lent itself to more challenge, to navigate more than just some, corporation that you work for. And you know, it's not, it's not run by family, so it's like. You, you get, you get a different flavor, even if it's a highly successful, major commercial enterprise. Like, it's just a different feel, you know? So,

emily-sander_2_03-19-2026_134958

Yeah.

rory-randall-liebhart_2_03-19-2026_134959

and I've had, you know, I've, I've, I've, I've had the ability to work with all types of businesses like that, whether it's startup tech businesses or, you know, family, um, investment businesses, things like that. Um, and on the flip side, I've worked for, you know, massive public companies too. Totally different dynamics, but um, but yeah, the family dynamic is interesting. Um, you know, how you earn trust from, as an outsider, from people, that's as important as how competent you are for your job. You know, my role doing these has been more like the CFO guy, so the money guy. So, you know, having my. Face under the hood of the, the, of the business. See what all is happening in there is, um, know, you have to earn a lot of trust to, to be given those, those vantage points. And so, but yeah, but then holding people to, um. To standards, you know, holding a family member to like spending standards or to, know, um, accounting standards or, you know, uh, documentation, things like that. You know, challenging to navigate takes a certain type of personality to be able to do that. And, you know, have people respect your, both your, you know, authority, but also your, you know, their ability to trust you, you know, so.

emily-sander_2_03-19-2026_134958

I think another big dynamic is did they bring you in or were you brought in by some other party and now like you're just here and there's, you know, family dynamics no matter what. And then you add the business to as like, is this an outsider? Or like, no, we know we kind of need this type of person in our business.

rory-randall-liebhart_2_03-19-2026_134959

really good point. I think, um, what you're alluding to is, you know, sometimes in my case I'll say I've come in, I was brought in by families in various different. Um, scenarios, uh, I could see where, where the other side of it is, like you were brought in.'cause someone, some of the family members themselves were not probably competent enough to be doing what needed to be done or some other dynamic that triggered a change. And I have not been in that situation, which would've been harder and way more awkward. Um, but basically for me, coming into a family business, dealing with family members, running the business is more like I spent just as much time relationship building with them on a human level, personal level. Um, as it is like, how, you know, how competent are you? How much do you understand this industry? I mean, I, for me personally, I've gotten into businesses where, it's manufacturing or whether it's investment, you know, different type of investment businesses like. I don't know these businesses, I, I'll learn them, but it's more like, Hey, you're a fit from the dynamic that's already here amongst the people, and family members. And so that's, I think where, um, where I work well is just my demeanor with these people, um, is, is very easy going and very trustworthy. So, you know, you could take like the smartest, there's way smarter people out there than me, but like, maybe they don't have the same way to connect with other people that way. So.

emily-sander_2_03-19-2026_134958

You're super threatening, like just that vibe you give off.

rory-randall-liebhart_2_03-19-2026_134959

Exactly. Yeah, yeah, yeah, yeah. Super aggressive, overbearing. Yeah,

twinkle-toes--it-_2_03-19-2026_134958

and mine's been largely the

rory-randall-liebhart_2_03-19-2026_134959

you have, you're right, exactly right.

twinkle-toes--it-_2_03-19-2026_134958

financial officer, generally

rory-randall-liebhart_2_03-19-2026_134959

Yeah,

twinkle-toes--it-_2_03-19-2026_134958

the spouse of one of the,

rory-randall-liebhart_2_03-19-2026_134959

that's,

twinkle-toes--it-_2_03-19-2026_134958

of the, one of the founders who was in the CFO role.

emily-sander_2_03-19-2026_134958

And that's not awkward at all.

twinkle-toes--it-_2_03-19-2026_134958

not awkward at all. Um,'cause you, you, you're essentially,'cause again, the, the private equity folks that are bringing me in are like, look, they just aren't a CFO. They, you know, they might be able to balance a bank account might maybe, and, but what they were, and this kind of goes to that Julia conversation earlier, is the founder trusted them with the money.

emily-sander_2_03-19-2026_134958

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

So they can, you know, so there was this really like, I don't trust, so think about that dynamic. The founder goes, I don't trust anybody with the money. So my spouse is gonna be running the books. And then the private equity guys come in and go, we're taking your spouse out. We're putting someone you don't know that we're putting in to the

emily-sander_2_03-19-2026_134958

Who knows more about this and can call out your mistakes.

twinkle-toes--it-_2_03-19-2026_134958

Yes. At that. But that. you were so uncomfortable that you put a family member in there as opposed to a qualified person because you didn't trust anybody with the money.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

we're gonna put someone in that you don't know that you didn't choose to go handle the money. So it created, for me all, almost every one of those was attention filled

rory-randall-liebhart_2_03-19-2026_134959

Mm-hmm. Yeah.

twinkle-toes--it-_2_03-19-2026_134958

They got. Even when they said, no, no, no. And in, in both cases, the festivals were like, no, this is great. I'm glad you're here. I'm happy to be giving this up. And in both cases it was just challenging one far more than the other,

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

far to the point where I got on the phone with PE guys and I go, they're, they're gone. Or I'm gone'cause this is not gonna work. This is like not working. And. can't,

emily-sander_2_03-19-2026_134958

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

you, you, you're gonna have to kind of throw down with the founder because this isn't working.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

know, again, I, to the PE guys credit, they, they said, okay, we got your back. And they, they made the moves necessary,

rory-randall-liebhart_2_03-19-2026_134959

That they did.

twinkle-toes--it-_2_03-19-2026_134958

it, it was not a comfortable experience at all.

emily-sander_2_03-19-2026_134958

Yeah, no, I mean I must have like a super like threatening persona because I've been brought in by PE and similar like husband and wife couple, and. Like very blatant, you know, when Emily's fired, here's what we're gonna use her salary cap for. I was like, oh, I guess we're talking about this in this meeting. Okay, that's, that's not awkward or unfriendly at all. But it was like, all right, like, let's move through this. And you know, you try to make the best of it and you try to like earn their trust and you do everything you possibly can. And then at some point it's like, if this is not gonna happen, then look. I was brought in to move this forward and I will do it with you and hold your hand and coach you and be an executive therapist to your dynamic and blah, blah. And then like, we gotta go, like you can get on board or get, get the F off board. Um, but that became a very, uh. Awkward, uncomfortable situation as well, where it was like

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

literally like they would forward me emails being like, here's the breakdown of like how we're gonna use this. Like, what is Emily doing? Like, well, I'm like, oh my gosh. So there's, there's that whole side of things as well.

rory-randall-liebhart_2_03-19-2026_134959

I mean, bringing it back to sort of the, the, the focus of the pod is like, you know, of a business, performance of teams, right? Like so you know, when there is and the dynamic, the one way you can, you know, really make it start to work is by. Showing everyone around you in that family or you know, in that dynamic that you are affecting change and positive performance, then, then you start to sort of see, see them get more bought in or, you know, um, kind of get the, the. Um, you know, working as a unit basically, whereas upfront, you know, it's like a lot of skepticism and like, Hey, this is change. Change is not good.

emily-sander_2_03-19-2026_134958

The outsider.

twinkle-toes--it-_2_03-19-2026_134958

Yeah.

rory-randall-liebhart_2_03-19-2026_134959

have to deal with that kind of stuff. But. they know that you're the real deal or you, you, you start to, you plus people you bring in, show those around you that, you know, it's the real deal to run a business with a performance, uh, you know, high performing team like that, then they, they either have to shut up or get out. And I, you know, one of the cases that Ed's talking about, here's exactly, that's what happened. You know, it was like, we, we, we know what we're doing here so you gotta, you know, shut up or get out and they got out, you know, so.

emily-sander_2_03-19-2026_134958

And here's the flip side too. If they are like, if they get hip to the fact that you do know what you're doing, you're gonna make the business better and move it forward. And option A is for like the founders to stay in place if they can stay in place through this whole. Process, like that's option A. Option B is like, if you can't make it for whatever reason, you gotta get off the boat. But it's not anyone's option. A and I, you know, we talk about this in our book, but it's, it's conveying to the founder, you still add tremendous value to this company, the way you add value changes.

rory-randall-liebhart_2_03-19-2026_134959

Correct.

emily-sander_2_03-19-2026_134958

If they can get over that, which, which is an open switch. Sometimes they can, sometimes it's a bridge too far. But if they can get, get there and get through it, that's, that's golden. That's money.'cause then you have like,

rory-randall-liebhart_2_03-19-2026_134959

you

emily-sander_2_03-19-2026_134958

yeah.

rory-randall-liebhart_2_03-19-2026_134959

It helps when they can see that they're gonna make a hell of a lot more money doing

emily-sander_2_03-19-2026_134958

Mm-hmm.

rory-randall-liebhart_2_03-19-2026_134959

you know?

emily-sander_2_03-19-2026_134958

Yeah. Yeah.

rory-randall-liebhart_2_03-19-2026_134959

of cases that, you know, we've all three been involved with together. It's like, you know, a lot of resistance by folks about change, but you know. When you walk away with a shit ton of money that your, your tone

emily-sander_2_03-19-2026_134958

Solve some of the problems.

rory-randall-liebhart_2_03-19-2026_134959

you

emily-sander_2_03-19-2026_134958

Yeah.

rory-randall-liebhart_2_03-19-2026_134959

and play a lot more and you make a fuck load more money and it's pretty compelling, you know, so, um.

twinkle-toes--it-_2_03-19-2026_134958

I was gonna say the other, the other piece of that, and the one that I've run into the, the biggest challenges has been where the family member that's in the business is not horribly effective and their identity is tied

emily-sander_2_03-19-2026_134958

Yes.

rory-randall-liebhart_2_03-19-2026_134959

Great point. Really good point.

twinkle-toes--it-_2_03-19-2026_134958

so it's, it's beyond, and again, they may have gotten bite one of the apple'cause it may have been a kid or a spouse in the business. And so they've gotten, you know, eight,$9 million out of it in the first bite. And they're like, yeah, but you know, my, my experience, see, and it's not what I've got. That's not what I'm seeing. That's not what's happening right now. And so I'm ringing. Um, and so that's, that's not what I'm, that's not what I'm seeing right now. And, you know, I feel like I've, you know, not enough money is, is coming in and it's disenfranchised

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

so that's a problem.

rory-randall-liebhart_2_03-19-2026_134959

Yeah. Can be. Certainly. Yeah.

emily-sander_2_03-19-2026_134958

Well, unlike another permutation of this is like I was working with, uh, with, uh. Kid of a founder and the, the, the parent was like v like a very strong personality, like very overbearing, very like micromanaged. You're doing it this way and you're doing exactly what I say, and you're my employee and not my kid, and blah, blah, blah. And so the kid was like, Hey, if I have someone who's like. Willing to teach me things, not just yell at me and willing to like show me how to do things and kind of invest in me and bring me up. That was a very positive thing for this individual. So it's like, hey, like I'm, I'm here to make your life easier. Um, I see kind of what you've been dealing with and what's going on, so let's work together on this stuff. And that was a very, you know,

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

Hidden Family Ties

emily-sander_2_03-19-2026_134958

conducive situation. So I think there's just different dynamics and situations and personalities you walk into. But if you are in a family run business, you. Best know those dynamics and, um,

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

think Ed, you and I have talked about a case where someone had a different last name and so like, oh, you are related to this person, and I did not know that until a couple months in.

twinkle-toes--it-_2_03-19-2026_134958

I, I actually had a, a situation where the, the private equity folks decided that they were going to, you know, they were basically going, well, yeah, we've got a problem here. And so we're, we're looking at kind of some of these, some of the family hires to see if there was any shenanigans going on. And, you know, so they're like, who's related? And so I give'em a list of who's related and then like. Two weeks later, they go, what about this one, this one and this one? I was like,

rory-randall-liebhart_2_03-19-2026_134959

What about no man?

twinkle-toes--it-_2_03-19-2026_134958

the wife's sister. That's the, that's the niece and that's the wife's brother-in-law. And I was like, I had no idea.

rory-randall-liebhart_2_03-19-2026_134959

Yeah. Yeah.

twinkle-toes--it-_2_03-19-2026_134958

I'm like, I didn't know they were family too. And you know, so there's, so basically at one point this company had 10% of the staff was related to the founder and the private equity were having problems with the founder. And all of a sudden they're like, well, if we have a problem with the founder, are we gonna lose 10% of the staff?

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

mean, my, my general, my general rule of thumb or advice for any founders out there is, look, if you're gonna be moving into private equity. and that's the direction you really want to go. My recommendation is take, you know, six months to a year ahead of that and figure that either you or the family members need to be out of the business at closing. Because even

rory-randall-liebhart_2_03-19-2026_134959

No.

twinkle-toes--it-_2_03-19-2026_134958

you are all adding value and it's wonderful and it's kumbaya and all that other stuff, the situation that. I just ran into where if it doesn't become that, and then the private equity guys go, okay, now we've got, you know, 5%, 10%, three key, three key executives are now at risk. gonna be factored into your purchase

emily-sander_2_03-19-2026_134958

Mm-hmm.

rory-randall-liebhart_2_03-19-2026_134959

Yes, it.

twinkle-toes--it-_2_03-19-2026_134958

piece is gonna look at, or I would be looking at it going. The team that's coming in the, as you grow the business, there's gonna be pressure to continue to promote family members. They may not be qualified. There's gonna be dynamics that aren't gonna work. The other folks in the company, and this has been unique, this has been, has been ubiquitous across everyone where there's, where there's family of a founder, they're treated different.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

they may not be treated different'cause they've been told they're treated different. They're treated different because you don't yell at the, you know, like I, I sat there and go, look Julia, I, I treat her at a higher standard than I treat the other employees flip side. I will guarantee to you. And I actually had Christie tell me, she goes, I'm not keeping track of her hours. I'm not, you know, I'm, I'm not gonna discipline her. That's, that's you because.

rory-randall-liebhart_2_03-19-2026_134959

You know, that's an interesting point. Yeah. Yeah.

twinkle-toes--it-_2_03-19-2026_134958

so you create a dynamic that really, that again, is fine in a small family owned business, but I will sit here and tell you if, when I go to exit the business, my, my strategy is to separate the legal piece from the accounting piece and exit the accounting

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

And that's why Julia's learning both. And she's gonna exit with me on the legal side because you can't sell the legal piece.

rory-randall-liebhart_2_03-19-2026_134959

Mm-hmm.

twinkle-toes--it-_2_03-19-2026_134958

so I'm like, okay, I'll, you know, I'll, and that'll be my. You know, kind of putter around and do stuff. And as I get old and senile, the, the accounting piece is something that the, that's a, that's where the rollups are today. And so, you know, but I don't want her to have to, that's a part of the dynamic that I'm like, look, I, that's not gonna work for, for an

rory-randall-liebhart_2_03-19-2026_134959

Mm-hmm.

twinkle-toes--it-_2_03-19-2026_134958

needs to be all arms length. And I'd recommend anybody kind of think about that going into a transaction position yourself.'cause you've added risk, which increases the risk premium. And is going to decrease your price by having family members in key positions in the organization.

Reps And Warranties

rory-randall-liebhart_2_03-19-2026_134959

agree with that. One thing I would add to that is, don't think you can just kind of fake it till you make it past close, because there's going to be. Reps and warrants and all sorts of other things in your master purchase agreement that's going to affect how things go after the sale. And so, you know, and, and most likely some of your purchase price is gonna be held back in the first place anyway for, for reps and warrants and things like that and in escrow or what have you. So yeah, you, you, you gotta have your housekeeping done. Um, for sure. In that way is what

emily-sander_2_03-19-2026_134958

Tell people what reps and warrants are again.

rory-randall-liebhart_2_03-19-2026_134959

It is basically, um, well, Ed's the lawyer, but I'll talk in non-lawyer terms, but it's you, you're making, you're making, um, representations about your company and facts to be true and you, you warrant that that's the case. And if they're found to be untrue, then the buyer has recourse to,

emily-sander_2_03-19-2026_134958

Yeah.

rory-randall-liebhart_2_03-19-2026_134959

be, you know, compensated or made whole in some way because of that.

When Family Works

emily-sander_2_03-19-2026_134958

Gotcha. And I think the other flip side to this is from the kids' perspective. So you have a second or third generation

rory-randall-liebhart_2_03-19-2026_134959

Yeah,

emily-sander_2_03-19-2026_134958

in there. I've, I've worked with people who are wildly insecure in their roles because they know, they kind of got it'cause of their family name and they know that it, had it been on merit and talent,

rory-randall-liebhart_2_03-19-2026_134959

sir.

emily-sander_2_03-19-2026_134958

would be a different situation. So, I mean, some of these people are really. Good people and they're doing their best, like at the, but they're just like, I didn't, I don't wanna do this. And they're kind of plugged into this thing. So you have some of those types of things. Um, I think

rory-randall-liebhart_2_03-19-2026_134959

It was

emily-sander_2_03-19-2026_134958

this is

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

like, uh, less common, but you have like a kid. Of a founder who happens to be really freaking good at that job.

rory-randall-liebhart_2_03-19-2026_134959

Hmm.

emily-sander_2_03-19-2026_134958

it's kind of like when you see these like, um, quarterback families like the Mannings where it's like Arch Mannings coming up and it's like, hey, like, you know that for his whole life he's been around that and he speaks that language is kind of in his blood and just in his DNA. And so that can be a huge advantage now. Does he have all the physical gifts and the mental pieces and all those things, but he's been in that since the time he was born, and that can, if you happen to be inclined toward that, that can be a huge advantage for some of these folks.

rory-randall-liebhart_2_03-19-2026_134959

no doubt about it. Yeah, I mean, and don't let us, you know, paint a picture of that. You know, family members or family run businesses or whatever is, you know, is not, these are not strong business people. I've, I've worked for some incredibly, you know, deft and savvy and and really impressive business people, and it happens to be a family business. Like, it just, it, it's all types, you know? Um, and it, it, it could be that they're, they're those things for that specific business, like what you were alluding to there, Emily. I don't know, like it's some of, some of these people take it so seriously, you know, their, their entry into the business being through blood, if you will. But they, they have the chops, they have the desire, they have the drive, and they have the wherewithal to be super, super, super successful. So, you know, it, it, it really is, it doesn't change the dynamic of family business, but you know, the, the individuals running the business, you can have as much of a high functioning family team as you can. Of non-related executives in some corporation. That's a fact.

emily-sander_2_03-19-2026_134958

And, and my dad. Um, so, uh, he was mentored by someone, uh, when my dad was young and this person brought my dad up into the role he has now. And then this person's son took over the business. But my dad remembers, uh, Chris', his name. Uh. Sorting magazines in the front lobby because his dad made him do every single job. And I mean like every like mail room, like sorting, you know, all like every single department. He had to sit there, um, for years. Like he didn't go to school. And he is like, I don't wanna go to college. Dad said that was fine, but you will sit in every single department I have for at least six months to a year. Um, so he did all those jobs and then it turned out that, hey, you know, um, the son had. Just a different interest, like a different, um, so he focused on a different part of the business where his dad was another part, but it worked fine. But he just understood that. So I mean, there are, you know, there are stories where this works out well. I,

rory-randall-liebhart_2_03-19-2026_134959

Totally.

emily-sander_2_03-19-2026_134958

know, know another one where it's in the family, but it's not to be whatever. It's an Italian family, so there's a large family and it's like, you know, cousins and son-in-laws and you, you have a large pool of people to pick from. It's not like, Hey, outta my two kids, you know, does either one of them.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

Chief Of Staff Glue

emily-sander_2_03-19-2026_134958

It's like, Hey, we've got like, and Johnny and all the, all the different things. I was like, oh my gosh, is there, is there any part of the stereotype you don't fit right now? Um, but that's.

rory-randall-liebhart_2_03-19-2026_134959

one value add as an executive outsider though for these businesses is somebody that can be the gel that kind of keeps, keeps things together. I think a chief of staff role for someone like that, or you know, sometimes the CEO, sometimes CFO, whatever. Those, those roles can be the thing that kind of gels the family together. I mean, I've personally been in situations where I'm like the go-between, between family members that aren't necessarily on the best terms and it's very uncomfortable at times, but sometimes it's necessary. You know, they're high performers in their roles, but. Outside of the business, they're not on the best of terms and it's just life. We all go through that in our own relationships. But yeah, it can be like the intangibles for, uh, an outside executive to be able to manage through that is a very, very specialized, even call it a skillset. I'd say almost like, I guess it could be a skillset, but I'm almost like, it's more like just a quality. You might have to be able to do those things, but um, it is important to have that kind of person that's sort of quarterbacking everything. Like I said, I think some roles lend themselves to that chief of staff being one of those, I think in a big way.

twinkle-toes--it-_2_03-19-2026_134958

Yeah, I think,

rory-randall-liebhart_2_03-19-2026_134959

too.

twinkle-toes--it-_2_03-19-2026_134958

think that's most key. that type of position.'cause you need somebody who is able to be responsible for everything and responsible for nothing at the same time, which is really what the chief of staff is and is able to, is able to kind of understand all those dynamics and then. Work to kinda move the pieces around the chessboard so that you're able to get the move right

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

rather than just, you know, kind of,'cause again, when you're an operational executive, you tend to be focused on your specific area of expertise and you'll wonder bus your way through the family situations and tend to run into problems. And I. Exceptional chief of staff is going to help you navigate that. And so that's,

rory-randall-liebhart_2_03-19-2026_134959

Oh, I,

twinkle-toes--it-_2_03-19-2026_134958

that is, and that it was actually in a situation similar to this where Emily, where I put Emily in a chief of staff

rory-randall-liebhart_2_03-19-2026_134959

mm. Mm-hmm.

twinkle-toes--it-_2_03-19-2026_134958

I needed somebody to be able to help. The entire executive team navigate some of these family dynamics.

rory-randall-liebhart_2_03-19-2026_134959

sure.

twinkle-toes--it-_2_03-19-2026_134958

the same thing. You know, same thing. We did something similar at, at uh, at the company Rory, you and I

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

I ended up with Corina in

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

and, and

rory-randall-liebhart_2_03-19-2026_134959

Absolutely.

twinkle-toes--it-_2_03-19-2026_134958

kind of the same

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

you're just like, okay, I, I need somebody to help navigate some of these strange dynamics. And the chief of staff is absolutely

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

And, and it's, and takes a lot of that. I don't want to say takes the pressure away, but certainly from the operational executives, it helps them. It's a, it is a resource that is almost required in

rory-randall-liebhart_2_03-19-2026_134959

truly,

twinkle-toes--it-_2_03-19-2026_134958

of.

rory-randall-liebhart_2_03-19-2026_134959

yeah. Yeah.

emily-sander_2_03-19-2026_134958

And it's interesting because chief of staff role is a high trust role, so you have to have someone you trust, you know, has your back. And so I, it was interesting that you brought in people who, like you trusted implicitly and you had worked with them before and you had a shorthand with when you were kind of. Surrounded in some sense with people like, uh, not quite sure where my footing is

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

with these folks, so that's interesting. So

twinkle-toes--it-_2_03-19-2026_134958

I don't, I don't think I could bring on, I mean, this is not a good, good thing for, uh, someone who recruits chiefs of staff, but I, I don't know if I could have a chief of staff who I hadn't worked with in a different

emily-sander_2_03-19-2026_134958

yeah. Yeah.

twinkle-toes--it-_2_03-19-2026_134958

where I had that level of trust. I just

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

Yeah.

rory-randall-liebhart_2_03-19-2026_134959

Makes

Trust And Timing

emily-sander_2_03-19-2026_134958

Yeah. And I think, you know, to the topic of this episode is like, are high performing teams better than family? You know, teams and nepo babies, and it's like, hopefully we've conveyed, there's not like a right or wrong answer to that per se. There's just kind of like, what, where are you in the business? Um, what do you need? What are you trying to get to? Uh, one thing I'll say for a number of these. Founders that were couples that I've been referring to, I can tell you without the spouse in early, the business would not exist. Without them being accounting or operations or whatever,

rory-randall-liebhart_2_03-19-2026_134959

yep.

emily-sander_2_03-19-2026_134958

whatever,

rory-randall-liebhart_2_03-19-2026_134959

I see

emily-sander_2_03-19-2026_134958

the business would literally not be there. So they, they played a critical, critical role, um, at, at that early stage. But anything else to throw in there? Like if someone's considering like, how do I make up my team? Or is this a risk or is this an advantage? How do I go about that?

rory-randall-liebhart_2_03-19-2026_134959

No, I think nothing that we haven't already covered, but I, I always think the common denominator with any team to be high performing is, is working with trust across people and across. know, kind of roles in departments and on an executive team. Without that, you know, the weakest link in the chain is, you know, can make the whole thing unwieldy. So whether it's a family business that you have to build trust in a certain way, or a corporate team that you have to build trust in a, like a slightly different way. It just comes down to that. You gotta, you gotta work together cohesively. Otherwise it's not gonna, it's just not gonna work.

twinkle-toes--it-_2_03-19-2026_134958

Yeah, I, I think it is a, like I said, I touched on it. If you're going into a private equity transaction, you know, I, I'd really consider whether. That risk is worth the, is worth

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

premium to the buyer. And if, and you're gonna need to address it one way or the other, but if you are an operating business, then you know you need to do, and I think, Emily, you just hit it well with the, some of these businesses and certainly the one we worked at would never have made it without,

rory-randall-liebhart_2_03-19-2026_134959

Mm-hmm.

twinkle-toes--it-_2_03-19-2026_134958

the spouse. I mean, it would've been a complete disaster. Um, so. You know, they just, it just outgrew the spouse and that's the, and, and their skillset. So I think the, the issue is you need to have the right people in the right spot at the right time in that company's life cycle in order to be able to be successful. And sometimes that is gonna be family, because you need that level of trust. You need people to be able to act before you have to say anything. They need to, you need to know that you know, they've got your back and everything's okay. And then. The business is likely to transition and change, and there needs to be an expectation as to how that's gonna look. I think at the beginning going, Hey, there's gonna

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

twinkle-toes--it-_2_03-19-2026_134958

where this is gonna have to transition and, and do it in such a way that, you know, it's, it's effective for everyone. And I think that's the, that's the hardest part of the, the, the puzzle. But it's, it's also, you know, the most critical to, to long-term success for the business.

emily-sander_2_03-19-2026_134958

And I would just say if you're in one of these situations or you're making some of these types of decisions. Take a step back and zoom out and say what's best for my family member as a family member. And treat that person as a human and individual.

rory-randall-liebhart_2_03-19-2026_134959

right.

emily-sander_2_03-19-2026_134958

Um, I remember early, early, early in my career, many, many moons ago, I was, uh, in between, in between stuff. So I did an internship at my dad's firm and I did a great job, and they wanted me, they offered me a job and it was like a sweet job. And it was like gonna be, you know, kind of a, kind of a, not a, not a. Conveyor belt automatic to kind of promotions and things, but it was like, here's, here's your path forward. And I turned that down. And I remember sitting across the guy, the guy's name was Michael Herman, and he said like, we wanna offer you this job. Here's the stuff and here's how it would work. And I was like, thank you so much. I really do appreciate that, but I'm gonna have to.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

know, decline this offer and move on. And he was like, N no, wait, what? You tell me why? And I'm like, because my last name is the same as my dad's right now.

rory-randall-liebhart_2_03-19-2026_134959

yeah.

emily-sander_2_03-19-2026_134958

everyone would know who I was related to.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

he is like, no, no, no, no, no, no. Like you'd be flying your own banner. Everyone would know you're doing it on your own. And I'm like, no, they wouldn't, Michael, they would, they, they would always have a question on the back of their head. And even if I did a great job and I was assuming I would do a great job. They, there'd be that little piece where like, I wouldn't know. They wouldn't know. And I was like, I'm not, I'm not doing that. And so I dec decline. He made me decline him three times I remember. And then I went off and I, you know, went on a whole tear of like, probably can psychoanalyze it for like 20 years trying to prove myself and I could do this on my own. Uh, which is kind of shortly.

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

after I, I met you two at G two and you kind of saw me in that, like, let's go stage. But, um,

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

that's what I was coming out of where I was like, Ooh, that's, that's a path. I could see that path. And my dad afterwards said, you know, um, as. As the administrative manager of this big pension fund, multi-employer pension fund, I, I wanted you on my team'cause I knew, I know you're good, but as a dad, like I'm really proud of you and I'm, you know, I, I'm looking, you know, I want what's best for you and this path is gonna be successful for you as well. So

Family First Closing

rory-randall-liebhart_2_03-19-2026_134959

Yeah.

emily-sander_2_03-19-2026_134958

would just, you know, people are people and if they're your kids, they're your family members. Just

rory-randall-liebhart_2_03-19-2026_134959

Mm-hmm.

emily-sander_2_03-19-2026_134958

'em like that first and, and then all the other pieces fall where they may.

rory-randall-liebhart_2_03-19-2026_134959

Well said. Well said. Yep.

emily-sander_2_03-19-2026_134958

All right. There we go. Little family. Little family talk. Thanks, ed. Thanks. Big rigs.

twinkle-toes--it-_2_03-19-2026_134958

family.

emily-sander_2_03-19-2026_134958

Welcome to family. There we go.

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