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My Father’s Retirement Package Could Break Our Business

EntreLeadership

Mon Jan 05 2026

Summary

The EntreLeadership Podcast (Ramsey Network)

Episode: "My Father’s Retirement Package Could Break Our Business"
Date: January 5, 2026
Host: Dave Ramsey

Episode Overview

This episode dives into real-world leadership and business dilemmas faced by entrepreneurs and leaders, focusing on high-stakes decisions like succession planning in family businesses, extending grace to employees, leading teams through unpopular changes, and confronting the question of whether and how to consciously grow your business. Dave Ramsey combines listener Q&A with his signature blend of candid, heartfelt advice and well-worn business wisdom.

Key Discussion Points & Insights

1. Mindset for the New Year: Approach as if You've Already Won

[00:10 – 05:54]

Dave opens with a motivational story illustrating the power of perspective, especially as leaders enter a new year.
“What if you approached [2026] as if you had already won, rather than from a position of scarcity and stress?” – Dave Ramsey [04:40]
The way you perceive challenges and opportunities in the coming year can be as important as your skills or experience.

2. Major Call: Navigating Succession & Dad’s Retirement Compensation

[05:54 – 18:23]

Caller: Sam (Oklahoma City)
Situation:

Sam is a 3rd-generation head of operations at a manufacturing firm (4.2M revenue, 22 employees).
His father faced health issues, wants partial retirement, and to transfer the business, but his desired compensation could “break” the company. Sam struggles to balance honoring his dad with financial prudence.

Key Numbers discussed:

Dad's current salary: $140k
Dad’s new ask: salary, benefits, rent totalling just under $500k/yr
Market rent for property: $144k/yr
Company profit last year: $600k

Highlights & Notable Quotes:

“It’s not dishonoring to keep a company… because if you go broke you can’t pay him. If he causes you to go broke, he cut his own foot off, right?” – Dave Ramsey [08:14]
Dave walks through the math: Even with $144k in rent and maintaining a $140k salary, profit would only drop from $600k to ~$450k; not “breaking the business.”

Dave’s Solution/Advice:

Avoid profit sharing for dad post-transfer; prefer fixed payments for clarity and future business growth.
Structure:
- Pay dad $150k/year for a set period (e.g., 10 years), then only market-value rent on the building.
- Lock in a long-term lease at today’s market rate to avoid future disputes.
- “The honor is not a dollar amount. The honor’s a posture of your heart.” – Dave Ramsey [17:35]
- Don’t let the definition of “honoring” become entangled with overpaying beyond what’s reasonable and sustainable.
If any negotiation becomes a matter of perpetual dissatisfaction, remember: “People who are bound and determined to be unhappy… there’s not enough money in the world to make those people happy.” [16:55]

3. Call-In: Extending Grace or Drawing the Line with an Employee

[20:28 – 28:17]

Caller: Brandon (Tulsa, OK)
Situation:

Fired a new employee (single dad) who missed 4 days in 4 weeks for family/sickness reasons; asks how and when to balance grace with discipline.

Dave’s Insights:

Use “the golden rule” — treat people how you’d wish to be treated, but also assess the scale and scope of the issue:
- Is it a one-off crisis or a pattern that threatens business function?
- In small teams, chronic absenteeism is a much bigger burden.
“Anytime we have a team member come to us and say a personal situation is a strain… the first thing I teach is to assess the scope and size of the problem.” – Dave Ramsey [22:45]
Illustrates with stories: grace for extraordinary, genuine crises (like a baby’s cancer diagnosis); less so for recurring, disruptive issues.
On communicating grace to the rest of the team:
- Be transparent when you can (“So-and-so’s kid has cancer…”), but maintain privacy and dignity for sensitive matters.
- Avoid “sanctioned incompetence” — don’t allow the team to perceive that misbehavior or excessive absence is tolerated.

4. Call-In: Leading Through Unpopular Change

[32:29 – 40:24]

Caller: Caden (Charleston, WV) – Small college athletic dept.
Situation:

Leadership feels a conference change is necessary; staff will see it as a step down and react negatively.

Dave’s Guidance:

Reference: Patrick Lencioni’s “The Ideal Team Player.”
Technique: Before announcing the change, go on a “listening tour” to make the team problem-aware — have them recognize the same issues leadership sees.
Story of Nehemiah: Address the problem with your team first, so “they start saying, ‘Hey, have you noticed that the walls are down?’” [36:29]
“If you can get them to recognize and be problem aware, then you can start to say… I think we’ve got to rebuild the walls. And then Nehemiah would start rebuilding… and he had everybody’s buy-in.” – Dave Ramsey [37:20]
Even with finesse, some team members may never buy in; leaders must still “square your shoulders, stiffen your backbone and make the call.” [40:18]

5. Call-In: Do I Need to Grow My Business?

[43:09 – 49:53]

Caller: Andrew (Anchorage, AK) – Small aircraft maintenance business
Situation:

Maxed out on work, reluctant to expand staff due to aversion to training/overseeing more people, questions whether growth is essential.

Dave’s Wisdom:

“Nothing is stagnant. It's either growing or it's dying.” [44:38]
Even slow, gentle growth is critical to staying vibrant and resilient — e.g., hiring even one more team member can increase stability and reduce vulnerability.
“You’ve defined what you want your business to look like. It’s supposed to bring you joy and serve your customers… And I like your attitude about it a lot.” [49:30]
Growth need not be dramatic, but you must always have a slight lean forward to avoid eventual decline.

Notable Quotes & Moments

On New Year perspective:
“What if 2026 was your job interview? What if you approached it as if you had already won?” – Dave Ramsey [04:40]
On family succession:
“The honor is not a dollar amount. The honor’s a posture of your heart… It’s not like I have to pay Daniel a certain amount for him to feel honored. If he does, that’s not real honor. That’s just a transaction.” – Dave Ramsey [17:35]
On leading change:
“You’re solutioning for problems that they don't believe are there. So what if you started telling them, here's a problem I see—a problem—and don’t present a solution?” – Dave Ramsey [36:15]
On business growth:
“Nothing is stagnant. It’s either growing or it’s dying… Lean in enough that you create some kind of upward momentum.” – Dave Ramsey [44:38]
On employee grace and boundaries:
“We treat people like we want to be treated… but I’d fire the guy too in your situation—not because I’m a big old meanie, but because his needs in his life right now do not connect with the needs we have as a company.” – Dave Ramsey [27:10]

Structure by Timestamps

| Segment | Topic | Timestamp |
|---|---------------------|----------| | Opener & 2026 Mindset | New Year perspective | 00:10 – 05:54 | | Call 1 | Family business & retirement succession | 05:54 – 18:23 | | Call 2 | Grace vs. boundaries with employees | 20:28 – 28:17 | | Call 3 | Leading through unpopular change | 32:29 – 40:24 | | Call 4 | Questioning growth in business | 43:09 – 49:53 |

Takeaways for Listeners

Approach leadership decisions from a place of confidence, not scarcity.
Succession planning demands clear numbers, objective assessment of “honor,” and often, tough conversations with family.
Extend grace where it’s due, but don’t sacrifice business function or invite sanctioned incompetence.
Change management works best when people are “problem aware” before being asked to buy into solutions.
Sustained growth—no matter how incremental—is vital; don’t confuse “no pressure to grow fast” with standing still.

Tone & Style

Dave Ramsey maintains his classic, practical, witty, and sometimes blunt tone throughout, combining empathy for callers with zero-nonsense financial and leadership advice.

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Transcript

A (0:10)

From the headquarters of Ramsey Solutions, this is Entre Leadership, where I take calls from leaders like you about what it takes to win at any stage of business and leadership. I'm Dave Ramsey, your host with over 30 years of experience leading in the trenches right alongside you. If you've got a question, we'd love to have you fill out the form@entreeleadership.com Ask or give us a call and we'll get you on the show at 844-944-1070. That's 844-944-1090. So here we are, the beginning of a brand new year. 2026. Can you believe it, man? Something about a new year that's a clean slate. A fresh start represents grace and mercy. Everything's in front of us, nothing's behind us. That's why they have the baby as the new year, right? It's the image that we have. What's interesting is how you approach the year and what you believe about the year is going to determine your results as much as how brilliant you are or how. How lucky you are or whatever else you believe in for destiny. I remember being at a motivational seminar a thousand years ago, and the guy told the story about perspective and the way we approach things. He said there was a guy who had been out of a job for years and he was really struggling. And he finally got an interview with this great company in New York City. It was the job of a lifetime, the job of his dreams. And he was really intimidated and really worried about getting the job. So he flies to New York and he checks into the hotel room, and just as he's getting ready to walk out the door the next morning to go to the interview, nervous sweat in the palm of his hands, heart's beating a little fast, the phone rings in his room just as he's walking towards the door. And he stops and he picks up the phone and it's his wife back home. She says, honey, I got great news. You don't have to go on the interview. I just won a million dollars on a lottery ticket. You don't have to go. We got a million dollars. And he said, well, yeah, that's awesome. He goes, we'll celebrate. This is amazing. This is a cool moment in time. And he goes, but I'll tell you what, just for the fun of it, just for kicks, I'll go do the interview. So he goes to the company to do the interview, and as you might imagine, he's in a little different posture. He's Relaxed. His heart's not beating. It's not life or death. Matter of fact, he may not even take the job if they offer it to him because he's got a million dollars, right? And probably because of his posture, the way he was thinking, the position of his heart. The interview went exceedingly well, and they made him a job offer beyond his wildest dreams right on the spot. And he said, well, I'll have to think about it. I need to talk to my wife and I'll call you guys later this afternoon and let you know if I need to take it or not. He didn't mention the million dollars. Got back to the hotel room, the phone's ringing again. He picked it up, and his wife said, honey, I. I made a huge mistake. I found out that I had read this wrong, and we did not win anything. We do not have a million dollars. So what had changed? He never really had the million dollars. But his perception, the attitude, the altitude, the positioning of his heart, the way he walked into the job interview changed because of what he believed his future looked like. He went from glass half empty to glass half full or completely overflowing, whichever way you want to look at it. And he wasn't arrogant or cocky in a way that was just off putting, but he had just extreme confidence. But he actually didn't have the money. As a matter of fact, he never had the money and was never going to get the money. But it changed his whole approach. So what if 2026 was your job interview? What if the year was what you've got to look forward to? Because it is. And what if you approached it as if you had already won, rather than approaching it from a position of scarcity and stress and anxiety? Those things are all real in business. We all get the crap beat out of us in this world called leadership. But what if you approach this year as if this was a Monopoly game and I might be a little ahead or I might be a little behind, but it's not life threatening, and I can just sit here with a pleasant smile and a straight backbone and some courage and approach our conversations completely different. I think that's what I'm going to do for 2026. I'm going to approach it as if I've already won. Why don't you join me in that? Our phone Number here is 844-944-1070. And you can join me here, too. That's 844-94410. Sam is in Oklahoma City. Hey, Sam, what's up in your World.

A (16:23)

Interesting discussion. I don't know if I'm helpful or not, but I'm just kind of thinking through the numbers with you and looking at the impact on you, the impact on the business profitability, the impact on your dad, looking at where he's coming from and trying to find that ground. But people who are bound and determined to be unhappy, Sam, are gonna be unhappy. There's not enough money in the world to make those people happy. And so. And if he's kind of doing all this against his will, and his wife wants him, your mom wants him to go travel, and he wants to keep working, there's not anything you can give him that's gonna be okay. He's gonna be pissed no matter what. Cause he's already pissed. But if he's really wanting to do this, and he also loves you and he loves the business that he's helped to run. Third generation now, then he doesn't need to do something that's going to handcuff the business or handcuff the son that he loves. And so that's the balance. So he actually has to honor those things as much as you want to honor him. But the honor is not a dollar amount. The honor's a posture of your heart. And his, too, by the way. So I want to honor Ramsey and honor Daniel Ramsey running this place and honor the entree leadership team doing the entree stuff. I want to give them honor, then they give me honor. But that's Not a dollar amount. It's not like I have to pay Daniel a certain amount for him to feel honored. If he does. That's not real honor. That's just a transaction. And that's what I mean by you can't make somebody happy. Just bound to determine not to be happy. It's not a dollar amount. And you know, overpaying someone or paying someone something, that's ridiculous. And him calling that honor, that's not true. That's not true. So good question. Good discussion. Sam, thank you for joining us. My man. Proud of you. Keep it up. It sounds like a great business. 4.2 million 22 team members, third generation manufacturing in the United States of America. Salute.

A (21:36)

Yes and no. We have to assess what's going on. And so this guy's a single dad. He's got a little girl that's been sick. That's one thing. The second thing is that there's a pattern. Taking care of your kid. Will never fire you for taking care of your kid. Okay? That's just. We just don't do that. And so there's a lot of grace for that. But if there's a pattern that says, quote, under the heading of taking care of your kid, that you're not working at all, then this isn't going to work because we need you here. And so if this, you know, if you ascertain by looking at the leader, looking at his attitude about it and just kind of assessing the situation, and you say, well, you know, based on that it looks like this is gonna be the way of life as long as this guy works here, then, yeah, I would have let him go. Because you can't, you know, if it's just gonna be the rest of the time he works here, he's gonna miss a day, a week, you know, no, that's not gonna work for me. So he's gonna have to get a different kind of a job because of his childcare situation and because this job requires you to be here because we can't do plumbing. Remote. Right. And so, you know, yeah, I would have done that. So anytime we have a team member come to us and say a personal situation is a strain and are just informing us and, you know, letting us know that something's coming, then the first thing I teach entree leaders to do is to assess the scope and the size of the problem. In other words, how much impact is it going to have on them? Okay. A weird example of that is I remember many years ago when I wrote about this, I had a lady walk in my office and tears in her eyes and her lips started quivering as she started talking and tear ran down her cheek. And I said, what's wrong? And she said, my baby's sick. And I went, oh, no, I'm so sorry. And I said, so what is it? She said, the daycare called and they're running a fever, and this is their first week in daycare, and this is my first baby. And I went, oh, yeah, okay, this is a little separation anxiety here. Mom's not. This is hard to put the kid in daycare, very hard to do that, especially your first baby. And you're taking this little baby over there, and then the first time they call, you're going to run right over there. And so when I'm looking at all that, I kind of smile as the old guy and go, this too shall pass. You're going to get through this, and, you know, you're going to get used to this. And by the time you've got three or four kids, they call from the daycare, you go, yeah, we'll be there in an hour or two. You know, we'll get around to it. Be there by the time, closing time. You don't drop everything and run over there like the house is on fire. And so I assess the situation. I decided it's a small thing, so no big deal, right? Go take care of it. The second one, about two days later, another lady walks in my office, same thing, tears in her eyes, lipsticks quivering. When she said, I said, what's wrong? And tear ran down her cheek, and she said, my baby's sick. And I said, oh, my gosh. And I'm thinking about the other one, kind of rolling my eyes, but I didn't. And I said, what's wrong? And she said, got cancer. Oh, whole different thing, right?

A (25:04)

Yeah, yeah. And so I said, you know, I called my HR director in. I called her leader in. She was in accounting at the time. And I said, her baby's got cancer. As a team, as a family, we're all getting ready to fight leukemia and beat it. Ready here. Ready, set, go. And those people didn't Mow their grass all that summer our team did. Those people didn't cook a meal all that summer, our team did. And she didn't work because you can't do accounting while your kids got chem. Your brain doesn't work when you're doing that. So she got the whole summer off with pay. Because that's what I would want somebody to do for my kid if my grandkid had leukemia. Right. And so we treat people like we want to be treated. But that's a lady that had been with us at that time for four or five years had not missed a day. This was an extreme situation. And so, you know, and she still works here, by the way. Been here 20 years. And if you say something bad about Dave Ramsey, she'll kill you. Because we were loyal to her and she's loyal to us. And so assess the size of the problem and then you can determine whether your company is of size and you can afford the absence and afford to extend the grace or not. You got 10 people. If one of them's not there, you have a 10% drop in production, minimum, maybe a 40% drop or a 30% drop, depending on how many people you got in the field. You don't really have the margin to extend extreme grace. And a day, a week, that's pretty extreme. So I would have fired the guy too, in your situation. Not because I'm a big old meanie, but because his needs in his life right now do not connect with the needs we have as a company to be able to have him on staff. And so you were not heartless, I hope, but I would not consider you heartless for having done that act. I would have probably done the exact same thing. But what I'm saying about all that whole long, drawn out story is that assess the size of the need and then say, can our company, can our situation. How much of this can we accept and is their request reasonable or do they have a weird thing going on? And so like we had a lady that worked here for about 90 days and then she was having anxiety and her request was to work from home for the rest of her career. Well, we work at work, so that doesn't work out. So you're going to have to solve your anxiety some other way. And that's not heartless. That's more like your situation, Brandon, where we assess the size and scope of the need and how does it compare or connect with our needs here and with our ability to extend grace. And we didn't have the ability to extend that kind of grace. Cause it changes the whole culture of our organization. If we start, anybody who's having a bad day with anxiety goes home. That doesn't work because we all have anxiety all day long. It's part of what we do. So.

A (28:35)

If it's something that's not shaming, we tell them so and so. So and so's kids got cancer, we're all praying and they're not gonna be here for 90 days. Cause we're going to chemo and we're paying them and they're on our team and we love them. And you should be glad we do stuff like that. Cause it could be you next. And the team, they like that. But if they think that we're just being weak leaders or something, or too cowardly to confront misbehavior, then that's sanctioned incompetence. And that's bad. You don't want the team feeling that. And if they don't know what's going on, they could think it's sanctioned incompetence. So if you say so and so's kid's sick. If I've got a team member who's mad cause they're not at work, cause their kid sick, that team member's in trouble. You know, we want. We want good human beings working here. And childhood illness is something anybody's ever had a kid. It takes your breath away. So even if you hadn't had a kid, you know, so all that. So yeah, it's a. I communicate it. But if it's something shaming, if they're having to go in for. I don't know. I've got two people right now that have maybe vague psychological things going on. I'll just leave it at that. And are doing some. Doing some on sites they're out of. They're not in the office. And they're getting help on site somewhere. That's about as much as I want to say. And that's exactly what I would say to the team too. Because the team listens to this. But anyway. But I mean, why would. I'm not going to shame someone that's trying to get help in that. That's not valuable. We just said so and so is working on some stuff. They're not here. And everybody just goes, okay, we trust the team. Because when we trust leadership, because they tell us what's going on, unless it's something that is harmful to the person and then it's the only time they don' and so, you know, just lots and lots and lots of grace on that as well. So, Brandon, I'm proud of you. You're asking the right kind of questions. You're why working for a small business is the best place to work in America because you actually care. You know how much analysis or heartache corporate America would have over that situation. 0 negative 2. I love entrepreneurs. Don't forget, guys, I started my company on a card table myself. So I know what it's like to have people counting on you, your team, your family, not to mention your customers. And when you're the one signing the paychecks, you can't afford to fly blind. But I'll be honest, early on, one thing that nearly sunk us was wasting time with spreadsheets that didn't add up because business units didn't talk to each other. I finally told my team, just fix it. And they did. We got netsuite. That was years ago and we've never looked back. See, netsuite isn't just for tech giants. It's built for growing businesses like yours. Over 43,000 businesses already run on NetSuite, including a lot that started just like you. And now with built in AI, NetSuite is helping them even more. It's one system connected to every part of your business. For real time insights, not guesswork. NetSuite AI flags, inventory issues, cash flow risks, even supplier delays before they become problems. So you can trust the data, stop wasting time and make the right decisions faster. Take a free product tour today@netsuite.com Ramsey that's netsuite.com Ramsey. Caden is with us in Charleston, West Virginia. Hi Caden, how are you?

A (35:57)

Yeah. I don't know if this will work. I'm making it up on the spot. Cause that's what we do here, it occurs to me there's a story in the Bible and I watched a guy do this in a leadership conference one time, and I've used it a lot and it's worked well for me about Nehemiah. He was sent, he was allowed by the king to go back to the Jerusalem. The walls had been torn down. And so Jerusalem was bare and was being raided by enemies. Cause they had no walls. And Jerusalem was being plundered because they had no walls. And Jerusalem had all these problems because they had no walls. And so Nehemiah was sent back to Jerusalem with the job, with the mandate, with the certification from the king to allow him to rebuild the walls. And instead of just coming back and blowing trumpets and announcing, which is what you're talking about, we're going to change, we're going to build the walls. Instead. He kind of went on a listening tour and went around and said, talk to people. He talked to the aristocrats, he talked to the soldiers, he talked to the merchants. And he goes, hey, have you all noticed that the walls are down? And they said, yeah, the walls are down. In other words, he presented the problem and he did this. He circled back a couple times to where finally they started saying, hey, have you noticed that the walls are down? There's now saying it to him. Because you're seeing problems that your team that's gonna be disillusioned by this move are not seeing. And you're solutioning for problems that they don't believe are there or they don't know are there. So what if you started telling them, here's a problem, I see a problem and don't present a solution. Just I see a problem. You know, we've got this problem because we're in this conference, we have this problem. And do that with several coaches, do that with several staff. The ones you're worried about being disillusioned by the move. And if you have the luxury of time, do it two or three times and try to get them to come to you and say, hey, have you noticed we have this problem cause we're not in that conference? Or because we're in this conference or whatever it is. And if you can get them to recognize and be problem awareness, then you can start to say, you know, I think as the leader, I've got to help you all solve this problem. I think we've got to rebuild the walls. And then Nehemiah would start rebuilding the walls. And he had everybody's buy in because they had become problem aware. And they bought into the solution. But if he had just come in and announced we're building the walls, they were going, why? We don't care about the walls. They're not problem aware. And if you announce this, they're not problem aware. It occurs to me, and so even if you lose the morale of a couple of them over time, I still am going to make them, through some methodology, problem aware so that then when it does come, they at least know. And also while I'm doing that somewhere in the conversation going, you know, if we changed, that'd probably be like a blow to your reputation because you'd be a coach in this conference instead of that conference and that might feel funny to you and just let them know they're seen.

A (40:24)

And they'll just sit there in the problem. You know, I know it stinks, but it's mine, you know, and it's like, yeah, sometimes people do that and there's nothing you can do to f just a toddler. And you know, that goes with it. So you're a great leader to be asking this kind of question, Kayden, and you know, and then still have the courage to square your shoulders, stiffen your backbone and make the call because that's what good leaders do, even if people don't understand. But I'm going to do everything I can to do a listening Tour a problem awareness discussion and involvement by asking questions and get them to recognize and see what I'm seeing. So at least they go, yeah, he kind of telegraphed that. I knew he was going to throw the pass over there. I knew he was going to do this. But it wasn't like, what the crap? What is, what is Kaden doing? You know? And it takes the shock and awe out of it, which is what you want to do. Let the air out of that. So very cool, man. You're a good man. You're a good leader. Thank you for calling in. I'm honored to have you in our Entree leadership audience. You wouldn't build a house without a blueprint, so why are you trying to scale your business without one? Here's the truth. Without a plan, you're just reacting, not leading. And if you're always reacting, you can't build the momentum your business needs to grow. That's why we're giving you Entree Leadership Elite's strategic planning template for free. This is the same template my team uses every year to plan for the next 12 months of growth. And you'll also get the course that shows you how to use it. In under 30 minutes, you'll know how to build a clear plan to grow your business so you can finally get out of reactive mode. No more flying by the seat of your pants. Just clear, practical steps that take you from putting out fires to actually growing. Go to entreleadership.com strategy to get the free strategic planning template today or click the link in the show notes. Hey guys, you can help us out by following the show, subscribing to the show, leaving a nice five star review, seeing how much you love us. Well, it's fair because we love you. So shut up. Thank you very much. We appreciate all the help and share the show. Click the click the share button or cut the little linky thing out and send it to a friend and say, watch this little linky thing. It's worth it. Works for me, guys. We appreciate you guys hanging out with us here. Andrew's in Anchorage, Alaska. Hi Andrew. What's up?