This week we dig into one of the trickiest conversations in small business: handing a family business down to the next generation. It's a topic that comes up constantly in the work we both do outside the show, and it rarely goes the way anyone expects.
We talk about the gap between owning a business and actually operating it, and how often parents assume they're still running the day-to-day when the reality has already shifted without them fully realizing it. We get into the emotional side too, the assumptions everyone makes without ever putting them into words, the resentment that builds when expectations aren't clear, and the awkward reality of a parent still drawing a full salary for a fraction of the hours. We also talk about the professional team around a family business, the accountant, the advisor, the insurance person, who's been there for decades and may not actually be equipped to help with a transition like this.
The through-line of the conversation is that almost none of these problems are really about money. They're about clarity, communication, and having the hard conversation early instead of waiting until resentment has already set in.
Highlights
Hey everyone, welcome back to this amazing episode of the Blue Cow RBS podcast. I am one of your award-winning hosts, Brad, along with the guy in Detroit Motor City. There you go. Thank you for hitting your cue today. I really appreciate it. I appreciate you getting it right today. that's awesome. That's awesome. I know it was a long week. I got it, but you know, it's
Doyle (:Steve. I got it, Tate. I'm all over it. I'm all over it.
Brad Herda (:Thank you for participating. We appreciate it.
Doyle (:We got it. Yeah, we got it. We got it down. We got it down. So
Brad Herda (:So, Mr. Doyle, earlier in the week we were doing a podcasting mastermind with our cohorts and our colleagues, and we were talking about guesting and different things. And then we're like, hey, you want to record today? So we said, sure. And you were given homework. Your homework today, your homework was to come back with our topic du jour for our conversation with our audience. So did you
Doyle (:Mm-hmm.
Doyle (:That was.
Doyle (:Yeah, exactly.
Brad Herda (:Knowing you were a kid in high school and college who didn't do all his homework on a regular basis, did you actually do your homework or did the dog eat it?
Doyle (:And well, no, Doug did need it because I mean, well, she did did get me a little haircut, so you know, kind of got me got me moving. But yeah, we we do have a topic du jour, if you will, for the day. All right, so let's let's go down the path of multi or family ownership.
and dynamics in a small business.
Brad Herda (:Alright, so we're gonna we're gonna light this fuse. It just passed so we're recording here just after the fourth of July and Steve wants to keep the fireworks going, apparently. So even though this is now gonna be in September, it's gonna be Steve's launch. He's he's he's got both hands on both keys. Here we go.
Doyle (:I d I did launch some fire. I did.
Doyle (:Here we go. So you know it's very interesting. So I do have a few clients that are family businesses, meaning in one case it might it's you know dad runs the business and one of the kids there's two kids in the business, one
Wants to be in the business, the other one, It's kind of just here and I don't know if I really want it. have another one where it's it's it's family business now. and looking at the next generation taking ownership. And I've had a couple conversations with some potential clients where it's you know.
Mom and dad have this business. sons and son-in-laws are in the business to take it over. And the interesting thing that comes up a lot.
Brad Herda (:Can't wait to hear this.
Doyle (:That comes up a lot, and it doesn't really matter what it is. I see it a lot in this scenario, is
I just don't know if they're ready to take over the business.
Brad Herda (:That's the that's the elder generation saying that statement, or is that you saying that as their as their advisor?
Doyle (:I don't
Doyle (:that that's whether or not that's a personal decision, right? That but we can navigate those waters. It's more of the original owners that are in that transition seat coming to the realization I want out, but I don't know if my kids want this.
Brad Herda (:kids want this or can handle it? Those are two different questions.
Doyle (:Yes. Correct. So let's go with let's go with can handle this for the show.
Brad Herda (:Okay. all right. So know, from a generational perspective and population, right, the age gap between parents and children has grown over the last 35 years. Right. My my parents, my parents were nineteen years older than I was, right? I didn't have my kids till I was third, right? So it's nineteen eighteen, nineteen years old. You started adding families, right? And then it was
Doyle (:Good.
Doyle (:Mm-hmm. Yep.
Brad Herda (:2022, 25, 27, 30, 32, 35. Right. So now you have this 30-year gap between yourself and your kids. And if you are 60 and your kids are 30, and you have a successful business that's maybe doing 40, let's just use a 30 to 50 million dollar type organization, family business, manufacturing company.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:Are you going to really hand over that business to a thirty year old?
Doyle (:Depends on how you look at it.
Brad Herda (:It's a it's a great question because the question that I have then becomes well, who has all the relationships? Who has who's tied all the did is is your business successful because you have all of your family friends that you do business with are now all your friends and you're entertaining, whining, dining, and you're in their pockets and vice versa. And
Doyle (:Yeah.
Doyle (:Yeah. Mm-hmm.
Brad Herda (:There's many family businesses that are like that where they're particularly in the construction trades world, right? It's Builder Bob is talking to AC Allen, who's talking to Flooring Fred, right? They're all together in cahoots and they all make the things happen. And now Flooring Fred is going to leave and go to give it to, you know.
Doyle (:Mm-hmm.
Doyle (:Yeah.
Brad Herda (:flooring Franny, his daughter, and she's outside looking in, and all of a sudden the business starts failing because she's not in the circle or wanting to do all not or wanting to do all the things, or I'm not gonna go snowmobiling with all the guys, or I'm not gonna do this, or I'm not gonna do that, or because she's got her own family and and wants to do things. And so yeah.
Doyle (:Mm-hmm. That is a reason.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm. Or right, you you've got let's just what you just mentioned was mom and dad have a set way of doing things.
child notices that and goes okay but if I'm gonna run this I want to do it my way which is not the same as how you got it here.
Doyle (:And this is where I've seen some of the interesting dynamics pop in of
I got some ideas from the kids have some ideas and it's at what point does the does mom and dad go, hey, you can go ahead and make some of those decisions.
But then some caveats come into play. you can't make right. Yes, exactly. Exactly. Mm-hmm. So so this is where it becomes very interesting, dynamic and conversation to have, because at some point there's a I want to let go as an owner.
Brad Herda (:there's there's there's a ton there's a ton of caveats that I was there's a ton of things like, hmm yeah, okay. We could
Brad Herda (:As an owner or as an opera as an owner or as an operator? Mm, but but two two
Doyle (:But I don't
Yes. Well that I it's two hats. Two hats. However, however, our owners aren't seeing it as operators. They are seeing it as I own this business. Therefore, I'm still in charge and I want to make sure that everything runs through me before decisions are made.
Brad Herda (:Yeah. Screw you, mom and dad. Right. Either trust me or you don't. One of the two, right? I mean, that's that's that's where it ultimately ends up getting to. So so there's a lot of things at play and every state is different, right? every state has its own different laws and rules as to what you can transfer, what you can't transfer, taxation, all there's lots.
Doyle (:Well, and that it does. Absolutely it does.
Doyle (:we haven't even got there yet. No.
Brad Herda (:we haven't gotten there, which is why and I don't necessarily know that I want to go down that path, but I want to get that out on the front end is that there are you know, lots of transfer of wealth abilities and things like that that you can do from a tax perspective and other things. We are not the experts in that area. Seek other professionals. If you need those connections, we're more than happy to make them for you or or introduce you to them. But for me, because I have similar situations.
Doyle (:Right. Yep.
Doyle (:Yes.
Brad Herda (:For me, it's always about separating and getting them, the family to understand you have these three levels, right? I have I have the ownership level, right? This the shareholder level, which is sits on top of the mountain. Then I have my board level that many family businesses don't have in play. They they
Doyle (:Mm-hmm. Yep.
Doyle (:Mm-hmm.
Brad Herda (:They see themselves all together as the board, but that's the right, that's where I bring in the, you know, mom and dad are the shareholders up here, but then I've got maybe mom, dad, uncle, uncle George, you know, Aunt Mary, maybe the kids. We talk about some things. That's really kind of your board of advisors, board of director type scenario that talk about strategy direction review things.
Doyle (:Doyle (10:11.879)
Mm-hmm.
Brad Herda (:Then we have our operational level is who's actually running the day-to-day. And this is where most elders of the family get lost. They want because they want to believe they're running the they they own the business. So they think they're running the business, but they're not. And they've already transitioned the operational ownership over without giving the authority.
Doyle (:Okay, why is that?
Brad Herda (:Because it becomes the phone call that why'd you do this? Why'd you do that? And then the kids are all pissed and moaned because they're like, Well, then you should have taken care of it. Well, I wasn't around. I was in Florida on vacation. Well, no shit. Right? But it needed to be solved today, not at your convenience because you're traveling. So you know, so I try to make sure that we get that operational side of the business really understood. And
Doyle (:Correct.
Yeah.
Doyle (:Mm-hmm. Right.
Doyle (:Yeah.
Doyle (:Mm-hmm.
Brad Herda (:And set up the
Okay, who's running the company? If I'm the are we calling in a president, operations leader, whatever I don't care what title you give it, but what are the things that fall on that responsibility? Here, mom and dad, here's all the things that you claim you're doing. Circle all of them.
Doyle (:Mm-hmm.
Brad Herda (:It's a very I don't there there's you're not gonna lose a lot of ink if you use a red pen. You're you're probably gonna have almost all the ink left in that pen when you give them that give that list of things. okay. so I go through a couple of those types of things to sort of create the clarity. It's harsh, it's ugly, it's emotional, but it's important.
Doyle (:Mm-hmm.
Doyle (:Yeah. Mm-hmm.
Mm-hmm.
Brad Herda (:And then they get to bitch and complain about all the things and all the stuff. Like, I'm like I and as as a third party outside there, I as a third party outside there, I'm like, if you want to do all that, great, then just say so. It's okay. But you didn't do it. Somebody else stepped up because they knew that needed to be done, and they're your family members. Is why are you taking it out on them to do the things because they stepped up? You should be proud that they stepped up.
Doyle (:These are all the things that nobody told you, right?
Brad Herda (:You should be happy they stepped up. Because if they didn't step up and call the lawyer or the legal team or the whatever, you'd be you'd be you'd all be, you know, whatever right now. So why are we arguing over that? Just if you want to do this, great. If you don't, then don't. Just decide. It it's okay. This isn't this isn't judgment. This is about understanding clarity.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm. Right.
Doyle (:Mm-hmm. Mm-hmm. I find it
It's more the converse how to bring up that conversation that is very important. It can't it can it usually is, but it doesn't have to be.
Brad Herda (:it's ugly it's ugly. It is ugly as hell.
Brad Herda (:It usually is, it doesn't have to be because too often it gets emotional instead of factual.
Doyle (:Well, because you're bringing it up when there's already tension. Usually. Yeah, usually something's happened. For at least for me. Something's happened. Emotions have built up. People are telling themselves stories. And then all of a sudden there is a yes. Correct.
Brad Herda (:no, not necessarily. Not
Brad Herda (:Without clarity there's only opaqueness.
Episode two what what episode was two two eleven, two ten?
Doyle (:I don't remember which one, but I know it's in the two hundreds. but anyways, right? It
Brad Herda (:Two twelve. Transparency without clarity, just opaqueness. Two twelve.
Doyle (:Yep. So you know, f the sooner you can identify that this transition is happening.
And you're having those conversations with a level of clarity.
Brad Herda (:Well, so so there's the is so so so you're assuming that there is a conscious awareness that it's happening. Most most of them are unconscious behavior that it takes place, and then there's animosity, remorse, regret, and anger and frustration and jealousy and all the other things that go along with it. Because the other part that tends to happen is that the kids are paid like the kids, mom and dad are still making full boat.
Doyle (:Correct.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Well, yeah.
Brad Herda (:for their salary that they're doing zero hours of work for or very minimal hours of work for and still getting paid their salaries plus distribution. And that that is the hardest conversation to have to say, look, you're working 10 hours a week. Maybe if we're lucky, we'll call it five. So you're working an hour a day, you're not taking home $200,000 a year for working five hours a day for your job role.
Doyle (:Mm-hmm. Right.
Doyle (:Mm-hmm.
Brad Herda (:It just it you just can't do that because it's well, I'm the owner. Yes, you are the owner, but operationally it makes no sense. And if you were to ever try to transition at some point outside the family, that's just gonna come back and bite you in haunts you. So you gotta find ways to allocate funds, assuming you're gonna also try to transition equity.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm. Yeah. So there's a there's a lot that comes up more when you're closer to that point. And I like to talk about it very much all the time, honestly. Because most there's so many assumptions. Well, I just assumed.
Right, let's let's let's have that conversation so that we don't have those awkward conversations. They're gonna
Brad Herda (:The the
To me, the the biggest question a sibling or a non-equity owner family member that's actually operationally running the business, the biggest thing to get that family over the hump, in my opinion, is okay, what do you need every year out of the business to live and survive? What is the what is the annual number? And then we can work backwards from there.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:And figure out how we're going to make it happen.
Doyle (:Mm-hmm.
Brad Herda (:If I need $300,000 a year out of the business to live the lifestyle that I want to retire in, because you've earned they've earned the right, they've earned the opportunity, they've done all those things. It's there. And if and if there's a right, if you're doing 10, 15, 20 a year, that that shouldn't be theoretically, it shouldn't be a problem to to make that happen. You just have to go about it differently. And the family member, the
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:The senior family members need to talk to their tax advisors and their tax planners because, well, now this is all taxable income. Hmm, is it? Could be, maybe, likely, could may I you gotta go through all those things. Your life is changing as well. And and you're entering another phase of life where it is a unknown commodity for you and you're scared. And is there will there be enough? Will there be this? What if they mess it up? What if the what if that?
Doyle (:Mm-hmm.
Doyle (:Right. Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:What if my favorite customer friend of mine decides to take his business somewhere else because we're not going fishing three times a week?
Doyle (:Mm-hmm.
Brad Herda (:How how's John gonna handle that with running the business without that? Mike, okay, well, those are all great conversations, but those are all ifs. So let's put things in place to not worry about the ifs, but let's make it the when's. When John understands that you are leaving the company and your son or daughter are going to run it better or even more effectively. Or they might be happy as shit to give you more business because now they're taking care of you taking care of the problem that you wouldn't step on that you wouldn't take care of.
Doyle (:Right.
Doyle (:Mm-hmm.
Doyle (:Yep. Yep. That's right.
Brad Herda (:you wouldn't hire that you wouldn't hire that extra shipping guy because why would I pay somebody thirty two dollars an hour to be in shipping and receiving? Well, because we got these customers that would give us more orders if we could get them out the door more effectively. That thirty two dollars, that sixty five, seventy grand a year is gonna turn into six and a half million dollars of revenue. I'm hiring that shipping and receiving person.
Doyle (:Mm-hmm.
Doyle (:Right. Mm-hmm.
Brad Herda (:What you don't know won't hurt you, mom and dad. You're just gonna see top line revenue go up. great. How'd you make this happen? You know that person you didn't want to hire? Yeah, we hired him. You did what? Over my dead body. Go fire his ass right now.
Doyle (:Mm-hmm.
Doyle (:Yeah. Uh-huh. Mm-hmm. Yep. So there's so much that happens just in that. I mean, that's this we're all we're doing right now is just scratching the itch on the surface on this. Cause there's so much from a family dynamic that
Brad Herda (:Doyle (19:20.871)
You know what, you know what, Brad? I think we're just gonna turn in that to this nobody told me series. All around family dynamics. Nobody told me. Family dynamics. When we go to transfer.
Is going to be challenging.
Brad Herda (:It it it is and it's not gonna be easy and I the the the other piece for the elder business folks that own the companies, own the things. Who's on your team?
Right. The thing that the thing that I find, the thing that I find when I go through the transition and through the transition of going with the kids to move on or or whatever happens, the financial advisor that you've been paying as the president of your company for the last twenty-eight years, likely the same age, likely starting to retire as well, all of a sudden, now they gotta do some work.
Doyle (:Doyle (20:20.382)
Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:They've been in your pocket collecting all the money for all these years. Now all of a sudden it's like, whoa, I don't know if I can really do all of that. I know how to take your money. I know how to do well, hold on, we're at this phase now that I need you to help me with my tax planning, my estate, my the Yeah, I don't know if I'm the right guy for that. Really? And now suddenly they ghost you or go forward. So so on that side of it.
Doyle (:Right.
Doyle (:Mm-hmm.
Mm-hmm.
Brad Herda (:Who's my accounting person that's all of a sudden been taking my money doing payroll and accounting quarterly? And now we got to go through and figure out some of these other things. And you whoa, that's gonna cost you more money. What do you mean it's gonna cost it's no? So your insurance person, your tax person, your property manager, whomever it might be, that are those big chunks of certainty around you, both personally and professionally.
Doyle (:Mm-hmm.
Brad Herda (:Many of those team members you've had for a long time.
Doyle (:Mm-hmm.
Brad Herda (:Are they really doing you a service or are they just there to collect their check?
Doyle (:Brad Herda (21:34.999)
And and that is the biggest thing I get when I make that trend. It's like, how come we didn't solve this problem sooner? Because that service provider never asked the question. They were just there, they assume that mom and dad were always going to say no because they told them no 15 years ago and never asked the question again. How come we're exposed on this type of coverage along because nobody asked the question? Because mom and dad are too cheap. They don't want to spend for that type of thing.
Doyle (:Yeah.
Doyle (:Correct.
Doyle (:Mm-hmm.
Doyle (:That's right.
Brad Herda (:You mean I could have spent that money, I would have been protected on that particular incident? Yes, you could have been, but you decided not to address your risks. How come that machine, we didn't replace that machine with X, Y, and Z? Well, because your machine sales guy that you had over it, pick whatever company you're with, said I'm gonna do this, and they gave you the thing that they had to get off the floor of that was sitting there for a bunch of years. You overpaid for it, and now they can't get parts for it. but but he never did me wrong before.
Doyle (:Mm-hmm. Yep.
Doyle (:Mm-hmm.
Brad Herda (:Yeah, but she didn't challenge him to do the right thing either.
Doyle (:Mm-hmm.
Doyle (:Exactly.
Brad Herda (:So, so kids and siblings and parents, right? You gotta understand who's on your team. And parents need to be open to the conversation to understand the trust but verify mentality for those service providers. Trust that they're doing the right thing, but verify it against somebody else.
Doyle (:yeah.
Doyle (:Mm-hmm.
Doyle (:Yeah.
Doyle (:Mm-hmm.
Doyle (:Yes. And I do I do see that where there's a lot of verification happening.
But because we're not communicating, it looks like a lack of trust. And so again, it comes back to nobody told me that it was going to be this difficult just to turn it over to one of my kids.
Brad Herda (:Mm-hmm.
Doyle (:There's just so much going on that all the stuff that you've known as an owner to look at that you're assuming your kids know no.
Doyle (:And allow them the opportunity to ask the questions to challenge you but not it well yeah, correct. I mean it's challenge.
Brad Herda (:Without being a dick about it. Well well, you're my kid, you should know this. But I'm not your kid right now. I am I am your I am your operation your COO of your company. I am yes, I happen to have the same last name, but I am not your kid in this room here. So stop treating me like that. I I just had this conversation with somebody the other day. When my youngest son was in robotics, we're there after hours and he
Doyle (:Yeah.
Doyle (:minute.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:lashed out at me. I pulled him aside. I said, would you ever do that to another mentor? He's like, no. I said, did you do it because I was your dad? I'm like, yeah, because you were yelling at me. I said, no. I wasn't yelling at you as my kid. I was yelling at you as a stupid team member on this on on this to say, hey, we need to get this done. There's a time to it.
Setting those boundaries of when you're when you're even if it's as simple as, Hey, I'm coming to you as my COO or I'm coming to you as my son or daughter, or I'm coming to you as my dad your father versus owner, using that language is really, really important to create those boundaries.
Doyle (:Right.
Cause if you don't it's fun.
Not really.
Brad Herda (:Right. So there there no, there's where it goes probably wrong. And then all of a sudden and the other piece to be really honest is the family really needs to sit down and understand what is the business really worth at the end of the day, potentially from an outside versus inside transition perspective. You know, and we had, you know, we've had like Matt Mindle drop on the show talking about eSop opportunities. We've had other FAs on
Doyle (:Well, yeah.
Doyle (:Mm-hmm. Yeah, you
Doyle (:Mm-hmm.
Brad Herda (:financial advisors talking things, what is it really worth? And is it worth the effort to continue the legacy? Or is it worth is it more worth the effort to get the check and distribute and move on? And if you're going to do that and your kids aren't owners, they don't have equity shares, you better have an agreement as to what that's going to look like or set expectations with them. If you're all of a sudden your company for four, five, six, seven million dollars, are your kids going to want to get out and take their portion of that?
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Brad Herda (:Or not, because if they're only thirty years old, probably not.
Doyle (:Yep. So if you need assistance with this, might know a couple people that could help you walk through just the conversation to have. Just keep that in mind. You know, if you need somebody to bounce ideas off of, that's what this show is for.
Brad Herda (:A few.
Brad Herda (:Look at you, Mr. Smarty Pants.
Doyle (:Brad Herda (26:44.428)
I'm glad we could keep you engaged for the entire show. How who you texting?
Doyle (:Hey, hey. You know? It's all good.
Brad Herda (:fl placing your bets. Are you doing a little day betting? What are you going on there? What's got what you got happening?
Doyle (:Me? What do I this
Brad Herda (:Polishing your phone?
Doyle (:It's over there, it's plugged in. no, I don't have any on my desk right at the moment. I just have this eyeglass cleaner that my surrender flag. I mean that and the dam it doll.
Brad Herda (:You have Bidget Spinners?
Brad Herda (:Surrender flag there. The family business surrender flag. There you go. There's our next Amazon product.
Brad Herda (:What?
Doyle (:We'll talk about that later.
Brad Herda (:So okay. All right. But yes, the transition out of family business is a
It's about planning, it's about making sure that it's clear clear communication. The biggest thing is open, clear communication. And
Doyle (:Mm-hmm.
Brad Herda (:As much as it's easy to it's easy to say, hard to do, try to keep emotion out of it. right. If you're 60, your kids are 30, you probably have a gap that you're not willing to to put in to willing to take that risk on, depending upon the size of your organization. But by the same token, do you trust your kids to do the right things and go forward? And and what do you need to put in place to make that happen? And how do you satisfy that? I've seen
Doyle (:Mm-hmm.
Doyle (:Right.
Brad Herda (:Organizations where the parents have hired one of their good friends to kind of be the gap person to lead the organization so until the kids can get to be old enough. Horrible decision. Don't do that, folks. Please don't do that. Please don't hire a family friend to do that because you y all you're doing is creating distrust between both sides and you're putting that friend of friend in a very bad position.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Doyle (:Mm-hmm.
Hundred percent.
Brad Herda (:Don't do that. So well, Mr. Doyle, thank you for coming with a topic. Thanks for lighting that fuse. I know we did a lot of rambling today, but there is the the family transition is a overlooked art form that everyone is unique and different, every state is unique and different, every business is unique and different, and you need to make sure you put the right people in your corners.
Doyle (:Hey. Yeah, no problem. So good.
Doyle (:Uh-huh.
Brad Herda (:And if your current team is not able to do that, you need to go find new team members to support you through that transition and find the right lawyers, find the right financial advisors, find the right tax planners, find the right support team through your operations planning, people process type things along the way. Cause so like when you sent your kids to school, they listened to the teacher, but they didn't listen to you.
Doyle (:Correct.
Brad Herda (:That's kind of the same that's kind of the same thing.
Doyle (:Yeah. Same thing. Same thing.
Brad Herda (:So All right, Mr. Doyle, have a fantastic rest of your day and we'll see you soon.
Doyle (:All right.
All right. Later, man.