Should I Take on a Leadership Role Again? (I Failed Last Time)

Summary

The EntreLeadership Podcast

Episode: Should I Take on a Leadership Role Again? (I Failed Last Time)

Host: Dave Ramsey · Date: February 4, 2026

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Episode Overview

In this episode, Dave Ramsey provides real-time, practical leadership coaching to listeners facing business and personal challenges. The main theme centers on whether to step into leadership after a previous failure, including how to rebuild confidence, approach relationships across generational gaps, and how to cast vision more effectively. Dave also tackles hard family business dilemmas, absentee ownership, and delivering tough feedback compassionately.

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Key Discussion Points & Insights

1. Stepping Back into Leadership After Past Failure

[00:51] – [08:19]

Caller: Tyler, age 29, considering a sales leadership role after a rough first attempt.

• The Challenge: Tyler struggled to lead an older team member previously and fears a repeat scenario. He’s now offered another leadership position in his company, again over a teammate older than himself.

• Root Issue Analysis:

  • Dave pinpoints that the prior issue was likely not age, but a matter of the team member’s unwillingness to accept authority.
    • “Sounds like he didn’t think you were worthy to lead him.” — Dave [03:47]
  • Tyler confirms he successfully led another older team member, reinforcing Dave’s diagnosis.

• Leadership Rhythms:

  • Dave recommends consistent 1-on-1 meetings (weekly or biweekly) to build relationship, accountability, and trust.
    • “My job as a leader is to serve you... and also, I’m gonna let you know where you’re not on track.” — Dave [05:35]
  • Emphasizes the dual role of leader: serve and correct.

• Managing Age Gaps & Insecurity:

  • Approach an older team member with humility—express desire to learn from their experience, while being upfront about your leadership responsibilities.
    • “You’ve been here longer than me...you’re going to help me be mentored and get better because I really want to tap into all of your knowledge base and learn from you.” — Dave [07:05]

• Vision Casting Concerns:

  • Tyler feels he struggled to rally his team around a shared vision.
  • Dave suggests collaborative goal-setting over “imposed” quotas to secure buy-in.
    • “A goal that we’ve agreed to is good for the health of every individual on the team and the customer.” — Dave [08:06]

Notable Moment:
Dave offers a practical template for casting a “desired future” as a leader, available in the show notes.

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2. Family Business Crisis: The Hard Choice

[14:48] – [30:59]

Caller: Cole, 26, must choose between growing his property management startup or rescuing his financially-struggling family trucking business.

• Cole’s Dilemma:

  • His trucking business–owned by his 59-year-old father–is facing enormous losses after a poorly researched acquisition in Alaska.
  • Family is “begging” Cole to help; Cole is torn between loyalty and the practicality of saving his thriving, self-made business.

• Dave Dissects the Situation:

  • The trucking business is deeply in debt ($2.5M) and bleeding cash; without urgent changes, bankruptcy looms.
  • Dave questions whether Cole’s future would actually benefit after years of painful recovery work.
    • “You’ll be giving up a decade of your life...and then if your dad hands you the keys and doesn’t want anything for the business...is that what you want?” — Dave [24:15]
  • Dave advises not to make the leap without absolute certainty about long-term rewards, clear agreements, and an exit plan if things worsen.
    • “If you go over there blind, I have to recommend you don’t do it without knowing where you’re going to end up at the end of the story.” — Dave [28:25]

• Key Guidance:

  • If helping, keep your own business alive as a fallback.
  • Get everything in writing: roles, ownership, debt repayment, and what’s promised after the turnaround.

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3. Delivering Feedback Without Drama

[32:09] – [40:08]

Written Question: Megan in Boulder asks how to give honest feedback without triggering team defensiveness and drama.

• Dave’s Feedback Formula:
  • Never criticize in public.
  • Calm, scheduled, private “accountability meetings” build trust and context for honest feedback.
  • Always combine correction with care for the whole person.
    • “You care and you love your people and you care about your people. And then you’re sitting down and saying, ‘Hey, we’re trying to hit this goal. This is the agreed goal...and you’re not carrying your part of the weight.’” — Dave [33:23]
  • If defensiveness is a pattern, examine your delivery style.
    • “I kind of think this is on you. I’m gonna let you spend some time in the mirror and think about how you’re giving the feedback.” — Dave [36:39]

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4. Running a Business Remotely (Absentee Ownership)

[40:08] – [47:40]

Caller: Luis, running a contracting business in Montana while on a long-term mission in Guatemala.

• Scenario:

  • Luis’ business operates smoothly under trusted managers while he oversees from afar.
  • He worries about long-term viability and maintaining company culture from a distance.

• Dave’s Perspective:

  • Such arrangements can work for considerable periods, especially if the management team is well trained to “finish your sentences.”
  • The issue comes when business conditions change (market shifts, partner company changes, major pivots).
    • “I don’t know without your set of eyes on it when they will recognize when you have to pivot the next time...” — Dave [43:13]
  • Strong, regular communication rhythms are essential. Growth may slow, but stability and purpose can persist.

• Key Takeaway:

  • Periodic check-ins, clear communication, and realistic expectations are foundational for remote leadership. If growth plateaus but stability holds, consider it a success given the circumstances.

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Notable Quotes & Memorable Moments

• On Impossible Relationships:

  • “That’s not on you. Nothing you could have done would have changed that...he didn’t want this little snot nose telling him what to do.” — Dave Ramsey [03:54]

• On Collaborative Vision:

  • “A goal that is imposed is called a quota. No one wants a quota. But a goal that we’ve agreed to is good for the health of every individual on the team and the customer.” — Dave Ramsey [08:06]

• On Rescuing Family Businesses:

  • “You’ll be giving up a decade of your life to help your family...the juice is not worth the squeeze.” — Dave Ramsey [24:15]
  • “If you go over there blind...I have to recommend you don’t do it without knowing where you’re going to end up at the end of the story.” — Dave Ramsey [28:25]

• On Honest Feedback:

  • “You can give feedback, but you’ve got to do it in the context of we’re all trying to win.” — Dave Ramsey [36:03]

• On Absentee Leadership:

  • “The distance is not an issue. It’s the flow of communication and your finger on the pulse of the business...some major portion of this—if it’s wobbling, you need to be able to feel that wobble and you can do that from Guatemala.” — Dave Ramsey [47:40]

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Important Timestamps

| Segment | Timestamps | |----------------------------------------|----------------| | Tyler: Returning to Leadership | 00:51 – 08:19 | | Cole: Family Business Dilemma | 14:48 – 30:59 | | Megan: Giving Feedback w/o Drama | 32:09 – 40:08 | | Luis: Absentee Ownership Concerns | 40:08 – 47:40 |

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Episode Tone & Style

Dave Ramsey’s style is direct, sometimes tough-love, but always practical and peppered with wit and strong analogies. He balances encouragement with honest reality checks, especially when discussing difficult or emotionally charged leadership and business crossroads.

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Summary Takeaways

• Not every failed leadership attempt is your fault; sometimes, people just won’t accept authority, regardless of your approach.
• Consistent rhythms of one-on-one connection and accountability are foundational for building trust and executing leadership duties.
• Vision casting should be collaborative: empower teams to imagine and own the destination, not just comply with top-down mandates.
• When considering complex family business entanglements, be relentlessly practical—clarity of roles, agreements, and long-term benefit is essential.
• Honest, drama-free feedback is a pillar of healthy teams—but it demands thoughtful timing, tone, and delivery.
• Absentee leadership can work with trusted managers and strong communication—but the true test comes at the next inflection point or crisis.

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For more resources and templates from this episode, visit: https://www.ramseysolutions.com/shows/the-entreleadership-podcast

Transcript

[A]

From the headquarters of Ramsey Solutions, this is entree 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 got a question you want to ask on the show, fill out the [e-mail] ask or call and leave us a number and we'll get to you and put you on the phone. Number here is 844-944-1070. That's 844-944-1090. Tyler is in Naples, Florida. Hi, Tyler. How are you.

[B]

Dave?

[C]

I'm doing well. Thanks for taking my call. How are you?

[A]

Better than I deserve. What's up?

[C]

So I had. I was hoping to get some advice from you. I am entertaining a new position at my company, and it would be a leadership position in the company. And specifically one of the. One of the person that would be on my team is older than I am, and I had an experience earlier in my tenure at the same company in a leadership role was leading a guy that was older than me as well, and it didn't go so well. It was very, very challenging to build trust and relationships with the guy that was on my team and just wanted to see if you had any advice for me on what I could do differently this go round.

[A]

How old are you?

[C]

29.

[A]

Okay, what type of business is this?

[C]

It's a general contractor.

[A]

Okay, so the guy that you're leading, what's he do?

[C]

He is on the. He's on the sales team.

[B]

And.

[C]

And so am I. And so he would. He would be a sales rep and I would be leading this specific industry that they want me to. To focus on.

[A]

Okay. All right, and how long ago was the other experience?

[B]

A.

[D]

18 months.

[C]

24 months ago.

[A]

Okay, and what happened? What was the end of that?

[C]

The company hit a little bit of a rough road and the position that I was in was, I guess, pseudo eliminated. And so they. I was asked to just go back into the field as a sales rep, which I did. And another opportunity has. Has come along since then.

[A]

Where'd the guy go that you had trouble with before?

[C]

He is still with the company, but reports to someone differently now.

[A]

Okay, what happened? What do you think went wrong?

[C]

Yeah, I don't want to. I don't want to make assumptions, but it just felt like. Like it was hard to get over the barrier or so it felt of the age gap be between us. You know, I I tried to, I tried to do what's best for him. I tried to lead with a, with a servant's heart. But you know, every time we would, I shouldn't say every time, but many times when we would have, when we would have conversations, they would start to, I don't want to say get aggressive, but they would be more conflicting than they needed to be. And I don't believe or it never felt like he, he trusted that I had his back.

[A]

Sounds like he didn't think you were worthy to lead him.

[C]

You could put it that way, yes.

[A]

That's different than not having his back. He didn't want this little snot nose telling him what to do.

[C]

That's it. That, that is a fair statement. I, I could agree with that.

[A]

Yeah. So that's not on you. Nothing you could have done would have changed. That is. Am I, am I wrong?

[C]

No, I don't think so. And the other reason I would agree with that is because I ended up hiring another guy on my team. But he then departed to go somewhere else. But he was also older than I was and we didn't have any problems.

[A]

So I don't know that it was an age gap. It was a lack of someone that has inability to be under authority and so, or at least they perceive themselves not to be under your authority. So your leader, if you take this role, this new role, or I guess you have taken it, has your leader got your back?

[C]

Yes.

[A]

Okay. With this type of sales arrangement, we have regular rhythms of every two weeks or every week, each leader will sit down with each individual and find out what's going on, good, bad and ugly, and how the leader can help. And also that's a time that you course correct if there's any issues. And so it's just a one on one accountability, very short, maybe 30 minutes. Once a week or once every two weeks, each leader meets with each person on their team. That happens all through Ramsey, not just on the sales teams. And that's an opportunity then for you to build relationship, for you to understand what's going on in their personal life, hear all their feelings out and find opportunities to knock down blockers and serve them and ask questions. How can I make your life better? That's my job as a leader, is to serve you in that way. And also I'm gonna let you know where you're not on track and where your sales calls aren't where they need to be. And if you don't have sales calls where they're not be, then sales aren't gonna be there. And if sales aren't there, then we're gonna have another problem. And it's a. So we got to get these sales numbers, we got to get these call numbers up or whatever it is that you're course correcting. Right. So are you going to be able to do that with that type of regular leadership rhythm of an accountability meeting with the new guys?

[C]

Yes, yes, I do believe so.

[A]

Okay. And so you know what I would do then is just sit down with each person, including this older person, and, and say boss's name. And I have talked about it, and we think the best way to get this thing running is to have a short meeting once a week or once every two weeks to where I can find out how you're doing and I can find out how I can help you. Because my job is to make sure that your job is as easy as possible and that you make the most money possible and therefore you make the company the most money possible. And everybody's smiling, Everybody. And so we're going to be doing that. The decision's been made and I'm going to be here to help you. And also part of helping you is going to be if we see something that's off track. But most of the time I'm just going to be learning from you because you're older than me, you've been here longer than me, you've been doing this a while, and I probably got a lot I can pick up from you. And so you're going to help me be mentored and get better because I really want to tap into all of your knowledge base and learn from you. But at the same time I want to be able to help you and at the same time I want to be able to speak to you if we need to course correct on something. So. And look at the guy and go, would you help me with that?

[B]

Okay.

[C]

No, I think that that makes a lot of sense. And Dave, I think one of the other areas where I was gapped in the past, and maybe you can shed some light on this for me as well. I don't feel like I was. Was great at, I guess, vision casting for, for the. The guy on my team, or maybe even the team, and in general, not to say that that would have solved anything or everything, but certainly something I feel like I could have been better at. Do you have any advice or best practices on what you've done as. As the owner and founder and leader of Ramsey when it comes to vision casting for the company?

[A]

Well, you're really for your department and your area is what we're talking about. It's not the whole company, but, like, okay, you know, the boss man, whatever his name is, has tasked all of us with, you know, increasing sales at this amount. And if we do that, we're all going to be happy because we're all going to be cashing some checks, and the company's going to be happy, and the customers are going to be happy. And so what we need to do is figure out how we can get there together, and let's sit down together as a group and trying to come out with a desired future. What is our desired future? What's the goal that as a department we're aiming at, and then what are each of our jobs in order to get there? And so you might even come up with a number that says, you know, okay, this is our. This is our annual goal. It's not a quota. It's something we're coming up together. This is what we're shooting for. The team is having a team meeting and saying, we want to go Super Bowl. Okay, well, what has to be true that wasn't true last year? Well, we got to hit the weight room. Well, we got to have to get rid of the OC and get a new one. Well, we're going to have to whatever, right? What's it take to get to the super bowl that we haven't done before? Because we got to do something different to get to a place we've never been before, and then just everybody together, pull together, and come up with a shared desired future, as Henry Cloud calls it. And when you've got that desired future, then you can come up with some elements of what has to be done. And if we do these five things to do the desired future, we'll automatically hit the desired future. And those are called defining objectives. And as a matter of fact, there's an actual template that we'll put on this episode where right now you can jump in on the thing and click, and you'll get the desired future template, and you can put that together, and we'll put that in and make it part of the episode for all of you listening. But, Tyler, you can pull it up, too. Then when you go back and listen to yourself on the podcast, and our guys will send it to you in the meantime, because we've got your phone number, so we'll get it out to you. But bottom line is, we rally the troops around a goal that is not imposed, but that they participate in creating a goal that Is imposed, is called a quota. No one wants a quota. But a goal that we've agreed to is good for the health of every individual on the team and the customer. And then we start figuring out what has to be true to hit that goal. Then we, all the troops, rally around that. Okay, I'm going to hit the weight room. All right. I'm going to do the workouts. I'm going to do the wind sprints. All right. I'm going to do the. I'm going to make the extra calls. All right. We're going to spend some more money over here on this lead on the CRM product. So we get you a better lead generation thing in here, whatever it is. What do we got to do to get this thing moving? And we're going to do it together. And let's go to a place we've never been to before and make more money than we've ever made in our lives and help more people than we've ever made than we've ever helped in our lives. Let's kick this thing in the butt, make it run. And that's vision casting. That's all it is. But you get buy in. It's not. You come in with trumpets and announce where we're going. Instead we talk about, okay, where could we go if we dreamed a little bit? And let's start coming up with some numbers. All right, if we did average order value of this and we made this many sales last year, we did this, a 10% increase would be that. What would a 25% increase look like? Oh, that may look like that. Can we get that? Is that possible? I don't know. Wow. What do y' all think? And just kind of keep throwing that stuff out there and then germinate and create at the first of the year. Create something that we're going to do by the end of the year, and then we start aiming at that, and if we're off, we got to pick it up, you know, we got to get with it. And that's all it is. It's vision. All goals are our vision with work clothes on. That's all it is. And so goal casting is what we're talking about more than vision casting. It's the same thing. We're still figuring out a defined, clear target, and then we start, you know, sending rounds downrange at the target. It's that simple. Yeah, that's good. Good stuff, Tyler. Good stuff. Those are really humble and solid questions. Very, very well done. 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 [e-mail] Ramsey that's netsuite.com Ramsey. Well, it's hard to grow your business when you're stuck in the day to day. If you're working 60 hours a week and most of that time is spent putting out fires, you're a fireman, you got a big problem, your business is running you instead of the other way around. Here's the reality. You can't grow a business until you grow yourself. That's why many of you need Entre leadership executive coaching. Our coaches have helped thousands of small business owners go from stuck and frustrated to scaling and confident. They'll help you uncover your blind spots, overcome what's holding you back and focus on the work that actually grows your business, not just the work that keeps you busy. So if you're tired of spinning your wheels, you're ready to lead the business with clarity and confidence. Go to entreeleadership.com coaching fill out a form to talk to our team or click the link in the show notes. Cole is in Springfield, Missouri. Hey Cole, welcome to the show. How can I help?

[D]

Hey Dave, thanks for having me on. I appreciate it.

[A]

Sure man.

[D]

So I am a part owner of a property management company. We manage around 400 single family homes, duplexes and apartments for real estate investors. I have a team of five employees and our gross revenue this year is going to be around $550,000 for a bit of a backstory. To better help explain my question. I'm very much in the treadmill stage of my business. I started this company right out of college and have spent the last five years really in the day to day, you know, slowly getting team members. And I'm finally starting to see the benefits of the work that I've put in. So my struggle or my issue is my dad has a family trucking business that's been very successful for over the last 20 years. But in the last 30 months it's experienced some significant financial hardships, some due to poor business decisions and some due to economic factors. So my question for you is, should I stay focused on my property management business? Should I leave my property management business to go help my dad, or should I try to run both my business and help out my dad's business?

[A]

How old is your dad?

[D]

He is 50.

[A]

9. 69 or 5. 9.

[D]

5 9.

[A]

Okay. How big a business is that?

[D]

They do just under $20 million a year in gross revenue.

[A]

What happens to the business when he's done?

[D]

He does not have a succession plan.

[B]

He's.

[D]

He's always really wanted me to come take the business over and work for him.

[A]

But you haven't wanted to?

[D]

It's not that I haven't wanted to. I really wanted to go out on my own, I think after college to, you know, learn business and kind of learn how to do things on my own before just stepping into my dad's business. I just always kind of thought that would be the easy button. And I'm in a unique situation now where my business is making a lot of money and his isn't. And now, now they're essentially begging me to come help them.

[A]

They are begging you to come help?

[D]

Yes. Him and my mom are.

[A]

You don't have any siblings involved?

[D]

No, I have two younger sisters, but they are not involved at all.

[A]

That's hard, trying to think through the different aspects of this. It's a bigger business, but it's struggling partly from some outside things. So you're going to have to overcome him doing stupid things and overcome the outside things. Is he gonna take that kind of input?

[D]

I think he will.

[B]

He's a.

[D]

He's a very smart businessman. But I think this whole situation has kind of made him paralyzed. He's just not. Not making smart decisions. And I think it's. It's because he's been so successful for so long and then just kind of nearing retirement and having all of these things hit him at once that has caused him Truthfully, to be, you know, on the edge of filing bankruptcy.

[A]

So it's losing money.

[D]

It's losing money, yes.

[A]

How much is it losing?

[D]

So he. His main business runs in the lower 48. It made about a million dollars. This year. He acquired a company out of Alaska, and it's projected to lose about $2 million. So that's. That's really the main issue here is he bought this company out of Alaska and it's losing every dollar that his main business brings in. It loses $2.

[A]

Does it owe money?

[D]

It does. They have a lot of debt, which is the main reason he can't get out of it.

[A]

How much debt?

[D]

About $2.5 million.

[A]

So the unwise business decision was he bought something and paid too much for it. That's killing him. So if Alaska went away, he'd be okay?

[D]

Yes.

[A]

Okay. I assume he signed for those notes?

[D]

He did, yes.

[A]

Okay, who does he owe the money to?

[D]

To local banks.

[B]

Here.

[D]

Here in.

[A]

So he borrowed money from Missouri to buy Alaska?

[D]

Yes, he did. And to make the plot even thicker, he has a business partner on those trucks. So he has a local doctor here in town that buys these trucks with him for depreciation and tax benefits. And so really, truthfully, what's your opinion.

[A]

As to why the thing's failing so dramatically? Because he obviously had no idea. I mean, this is. He didn't just miss the projections a little bit. This is like a scam. I mean, he, like, got scammed.

[D]

Yeah.

[A]

Or something. Or he missed it so amazingly bad. How did. I mean, what in the world happened?

[D]

I'm not. I'm not truthfully. Sure. I think. Yeah, I think he really did get scammed. He just didn't do his due diligence during the acquisition.

[A]

He overpaid so much that. Yeah. So he's got two and a half million debt, but he's also losing two million dollars a year.

[D]

Correct.

[A]

Where's he coming up if he's only making a million in the lower. Where's he coming up with the other million in losses? Borrowing it.

[D]

He has a really good friend that is his partner, who's a doctor, who is making all of his payments and essentially keeping his business Alive. It's about $100,000 a month that he's paying.

[A]

Okay, so if you go over there, what's the way out? I don't see a way out.

[D]

I think the way out is to have a tough conversation with his partner, to sell all these assets at a loss and try to get a loan to his friend, rather than to the bank. And then I think there's some issues with team members and employees that could be fixed that could really help turn this business around as well.

[A]

So just sell off the assets for Alaska, close it and move the debt from the bank to the doctor.

[D]

That's kind of what I'm thinking. Unless you, you have a better suggestion, that might work.

[A]

But you still got a $2.5 million problem laying there. And. Let's see. So, okay, if you move that over, what will the assets bring? If you sold Alaska off for book.

[D]

They would bring. We're in the middle of getting quotes, but probably a million dollars.

[B]

So he said, okay, so you'd move.

[A]

A million and a half off and you make a million a year, you get rid of the bleed and you pay the million and a half back in a year and a half and you're out of debt. Has the lower 48 got debt on?

[D]

Does have some debt, but the business is covering all of the debt and is making good money.

[A]

But if you're making a million dollars a year, you can recoup the partner, put him back whole pretty quick on the million and a half plus whatever else he's put into it. Right, so it sounds like a three year turn.

[B]

Yes.

[D]

Yeah.

[A]

And then the question is, do you want to do that with your life?

[D]

Yeah, that's. That's what I'm struggling with. I'm finally making a fair struggle.

[A]

That's a fair struggle.

[D]

Yeah.

[A]

So if this all turns around and, and let's. Okay, three years. The pardoner is an owner. To what degree?

[D]

He's an owner in a separate llc. It's essentially just a holding company. So he doesn't own anything in the actual business that all the revenue flows through. It's just a LLC that owns the assets. That's the semi trucks for the lower 48 as well.

[C]

Yes.

[A]

Okay, so I mean, where in this story do you end up with this business free and clear of the partner and the debt? 10 years down the road of working for nothing and then you end up with this business. Is that what you want?

[D]

I'm not sure. I would do anything to help my family, but I don't. I really.

[A]

You'll be giving up a decade of your life to help in your family. That's what we're saying. And then if your dad hands you the keys and doesn't want anything for the business, but by then you've worked your way all the way out of the partner because you know that partner owns, you know, owns you as Long as he owns all your assets. Duh. And so we gotta get him out of there, and we've gotta get him repaid, and we gotta get Alaska cut loose, and we gotta turn this thing around, all of that. So you end up with a trucking company 10 years from today. And you're how old right now?

[D]

I just turned 26 yesterday.

[A]

Yeah. So you're 36 years old with this thing, and your dad is 69, and he's retired and didn't get anything. Or if he wants something, it takes it even longer. Wow, Cole, this is hard. The end game for you, the juice is not worth the squeeze. The only reason you would do this is just to help your dad, but you've got to keep the other business open because you're. You're. You're not going to be in this business because it may not make this turn. And you actually. You don't want to go down. You don't want to go over and help them rearrange the chairs on the Titanic. So you want to be over there helping and. As long as you can. But I don't. And no offense to you, but even if it was someone super experienced, if I came in there, okay, I'm not sure I could turn this dadgum mess around in time to make it fun to have bothered to screw with it. And that's not being cold or anything. It's just your dad has got such a deep hole he's dug here with so many different ditches running out of the hole that by the time we get all that fill back in, there's not enough fun.

[D]

Yeah.

[A]

You know, if you did go over there, it would just be to try to help and not really casting your future on that. Instead, it's just you putting some business energy, some. You're not in the forest, so you can see the trees stuff. You can encourage your dad, coach him along, give him some ideas, even help him implement some of the ideas. Meanwhile, you got to keep your other thing running, because I don't. I don't. I don't think. I don't think you had any desire to go over there and run this thing ever. And the fact that it's in the ditch and your dad and mom are asking you for help, and you love them and you want to help them, which makes you a good guy. That's your. The only appeal to you, because there's no business appeal at all. Am I missing something?

[D]

I mean, it does make good money. Prior to this acquisition, he was making 1.5 to $2 million a year, every year.

[A]

Yeah. But you're gonna have to use all of that to clean the partner out. Clean the partner up and clean the partner out.

[B]

Yeah.

[A]

And that's gonna take three to five years. And then. So there's no fund for the first decade. That's what I'm saying.

[D]

Yeah.

[A]

And then at that point, how's your. What's your dad going to want out of this?

[E]

Do you.

[A]

Did you. Did you say to yourself before this all happened, gosh, someday I'm going to go over there and run that company?

[D]

I did. I've kind of always thought that.

[A]

Okay.

[C]

Back my mind.

[A]

So this thing you built was kind of a temporary thing?

[C]

Yes.

[B]

Yeah.

[A]

All right, then that's different. So then if you're going to go over there, you need clarity on the end of the story. If this works, where does it leave you? Okay. If you sell off the assets, we restructure with the partner, then we buy the partner out over time, then you buy your dad out over time. What's the timeline, what's the dollar amounts, and where does this leave you at 40 years old? You've got to have clarity on that, because if you go over there, assuming all these people are going to take care of you. Well, you know what assuming does?

[D]

Yeah.

[A]

Yeah. So we don't want to do that. I want lots of clarity from dad and the partner that, okay, I'm going to come over here and I'm going to pour myself into this, and I guess you're going to sell off your other thing or just let somebody run it for a while and see what happens in case this thing blows up on you in six months, you could go back over to the property management thing. If you kept it running a little while, you got somebody can run it for you.

[D]

I. I don't, but I could always try to find someone.

[A]

Yeah. Or live. Lift somebody up from inside and say, you're now the manager and I'm gonna give you a percentage of profits, and then you and I are going to meet once a week for an hour, and we're going to. I'm going to help you keep running it, mentor you over here, and then you're going to spend your other 52 hours over at the trucking company. Yeah. You really need to know. Not just. I always thought I would work there. And not just. It's a big business. It makes a lot of money. No, it doesn't. It sucks right now. And not just I'm helping my mom and dad, but also, where do you end up. And that's not selfish. Because when you're down there fighting through with dealing with these stinking bankers and selling off these assets, and you get the grit and grime of this whole mess on you because this thing's messy. There's a lot of fish hooks in this. You're gonna get stuck, you're gonna bleed before this is over. And so you gotta know that the blood and the calluses are worth it. And that at the end of this thing, your dad's not gonna go, oh, Well, I want $20 million for this. And you're like, you've lost your dadgum mind. You know, after what, After I gave up the other thing came over here, and now you're getting greedy. I mean, you need to get all this cleared up ahead of time. And then if he gets early onset or something, you've got it all on paper and you know where you're going. And you guys need a letter of agreement that this is where we're going. And involve the. Involve the partner. If you go over there blind, I have to recommend you don't do it without knowing where you're going to end up at the end of the story. You should not go over there. And I think he's at a place he's humble enough, he's willing to give you that. I don't know if the partner is, but the partner's right writing some big checks. So maybe they're ready to get a little help over there and stop the dad gum bleeding. Wow, that's an interesting case, Cole. I hope it works. I hope you can turn it around. I will tell you though, man, you got some heavy lifting to do. No pun intended.

[E]

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[A]

Question of the day is from Megan in Boulder, Colorado. Dave, I want to give my team better feedback, but every time I do, someone gets defensive. What's the best way to give honest feedback without triggering drama? Well, we don't do drama, so drama is a deal breaker. So. Well, I think you need to be real careful about how you're giving honest feedback and the setting in which you're giving the feedback. If you're giving negative feedback in front of other people, then you deserve the drama. You should never do that. If you're giving feedback, corrective feedback with an inappropriate level of volume or laced with cuss words, then that's not negative feedback. That's cussing somebody. Don't do that. And you're gonna get drama. But if you say, all right, every Thursday morning at 8, you and I are going to meet and see how you're doing and see how I can help you. And we're gonna have a regular rhythm of an accountability meeting, and we're gonna set the goals together and we're gonna work together to hit those goals. And I'm here to help you, and I'm also here to observe and let you know if you're not, you know, if you're missing a guardrail here. And if, based on that, very calmly and with a scheduled accountability meeting, that you sit down and you learn about their personal life and you find out that their daughter is sick or you find out that they've just had a new baby, or you find out these things and you take all of that into consideration. You know, you care and you love your people and you care about your people. And then you're sitting down and saying, hey, we're trying to hit this goal. This is the agreed goal. And you're not carrying your part of the weight. And then if they get defensive, probably not going to do that very often. I'm going to say, look, we're going to work on this. And so if you don't want to do this, then you may be opting out because we all here adhere to this guideline, and this is what we all do. And if you want to be a We, this is how you get to be here. But you know, occasionally we'll have somebody lose their mind and go into drama mode, but it's so rare because we don't tolerate it. So the leader is not in drama mode and certainly not the person. But, you know, I don't know the extent of what you mean by drama, obviously, from an email coming in, but I guess I'm just gonna. One of the corrective measures is the drama. We're gonna correct the drama. Look, the proper way to react to this is say, yes, I see it, be self aware, understand what's going on, but you are dropping the ball on this. And if you can't see that, then we've got another problem. A, we have a drop ball. B, we have a lack of self awareness, even after I pointed it out. So this is a problem. Now we're going to have to work on that because we've got to get aligned on this, you and I, because we're going to work together and we're trying to win the Super Bowl. We got to put the ball in the end zone and so push, push, push, push. And if you get pushed back then, then you've just got an immature person and you've got a bat higher. And what that means is that they're going to have to work somewhere else. We're going to set you free in Jesus name. And so, you know, that's. We just can't. We're not going to. I'm not going to sit with somebody three times and they're defensive on the same thing and still not hearing me. We're going to be talking about other things other than the thing they're defensive about, like their defensiveness or their drama. You know, this is a new thing we have to work on now because before we were just working on this other problem. But now that you got defensive and drama about it, now I got to work on the defensive and drama part. And so if we can't correct on that, then we're agreeing that we can't work together. And that means you leave because I own the place. So I'm not leaving. You are. And that's that, you know, that's what's going through your head. We're not that smart alec with them. Okay, but you know, you just take that strong a stand with them, Megan. Very calm, very kind, very clear, but very strong and a regular rhythm with an accountability meeting that's working towards a set goal. And one of those goals is to correct the issue on this. And so I'm going to give you a guess the way you worded this, that I want to give my team better feedback. But every time I do, someone gets defensive. Okay, so this sounds like you. It doesn't sound like them. It sounds like your delivery might suck. So, you know, you can give feedback, but you've got to do it in the context of we're all trying to win. And how can I help you get to the place I'm helping you feedback with? I'm gonna serve you, walk with you, lift up your arms, make sure we get this done together. We're not doing it, but if you just walk past someone in the hall and tell them to do something, that's way different. And, yeah, you're going to create problems with that, especially if you embarrass them in front of other people within earshot of other people. And so, yeah, so since it isn't a singular person, it's. Every time I do someone, I kind of think this is on you. I'm gonna put you. I'm gonna let you spend some time in the mirror and think about how you're giving the feedback. When you're giving the feedback, what it sound. Reverse moccasins a minute, walk a mile in their shoes, and let you hear what you're saying back to yourself and see if you can adjust the way you're delivering this. I'm very sarcastic and bombastic in my head, but I would never talk to someone directly, individually like that, that I'm trying to change. That's counterproductive. And so I'm gonna be kind. I'm gonna be clear. I'm gonna be direct. I'm gonna be strong. But. But. But I'm not. I'm not sarcastic like I am here on the air, and I'm not, you know, I'm not gonna bust up on somebody like that. That's. We're not doing that. But in my head, I am. I'm going like, I own the place. You're confused. You know, in my head, but I'm. I wouldn't say that to somebody, so you kind of got to think that through. Megan, is the inner monologue leaking out? Maybe? Is that the. Is that what's going on? I'm not sure what it is, but, yeah, the wording of your email might be a clue. If you're working 60 hours a week and most of that time is spent putting out fires, you got a big problem. Your business is running you instead of the other way around. You're a fireman. That's why you need Entree leadership executive coaching. Our coaches help you uncover your blind spots, overcome what's holding you back, and focus on the work that actually drives results. If you want that kind of clarity, go to entreeleadership.com coaching and fill out the form to talk to our team or just click the link in the show notes. Thanks for being with us. If you want to help us out, click the follow button or the subscribe button. Leave us a nice five star review. Share the show, tell people about the show, spread the word. Baby, we need your help. You are our only marketing chance. If you want to be part of the program, leave us a phone number at 844-944-1070. That's 844-944-1090. Luis is with us in Helena, Montana. Hi Luis. How are you?

[B]

Hey, doing well, Dave, thanks for taking my call today.

[A]

Sure. What's up?

[C]

Hey.

[B]

So I think to boil down my question simply is, you know, how can I manage to run my business with my permanent absence? We run a contracting business in Montana. I've been in operation for about seven years. We did about 2.7 million year of 2024. We had a projection of probably increasing that to about 27%. But in that time we felt, my family felt the calling of jumping into the mission field. And so we've been in Kichegu, Guatemala, serving for the last nine months. And so since then and being here, our, our company's been operating by our, our project manager and then kind of, you know, I guess another project manager which is family. And it's been running smooth. But now that we've made this commitment of staying long term in the mission field, I just kind of have some, you know, some nerve, I guess, some fear of not being present because I was very present, you know, the last seven years I kind of grew this business simultaneously working in the fire service full time. And then it kind of just grew where I stepped out of the fire service and just focused on my business. So just wanted to see your thoughts on that or if it was even feasible and just kind of. Yeah, see, see what you, what you think on that.

[A]

How many team members?

[B]

So we have two. Two team members that are leaders and then we have sub crews. We have two sub crews that range about six to eight total. They fluctuate and that's essentially who carries out all of our work. And I guess to be a little bit more specific, we were in the contracting field which was building envelopes. But then we started seeing that our Profit margins were a lot better doing roofing and siding. So then we transitioned to exclusively roofing and siding. And then ultimately with my leave, just to help the team out, we dropped down to just roofing. And now all of the roofing jobs are actually coming through another partner company in our hometown. So essentially they don't have laborers, our company has laborers and they've been in the area 20 plus years serving. And so the relationship was doing work for them exclusively with my absence. And it's worked out well. We, we're all Christians, believers. And, and it's just the flow has been a lot better than what we expected as an entire, I guess, team effort. And so that's some of the peace that gives me in making this decision to stay long term. But at the same time, like I said in hearing your, your entree leadership podcast, at times that can also, I guess, be sticky.

[A]

Yeah, I mean, what you're describing is a very difficult to run absentee. And because there's a lot of day to day decisions, these project managers, or whatever we want to call them managers at this stage are, they're running the business. And so the best you can do is train them to do it the way you would do it. Be able to finish your sentences. What would Luis do? What would Luis do in every one of these cases? And then if they know the answer to that, they can execute and then just report to you, you know, once a week or once every two or three days whenever you get updates, what's going on, plus or minus emergencies. And so that can be done. You guys, it sounds like you have pivoted three or four times since you started this. And I don't know without your set of eyes on it, when, if they will recognize where, when you have to pivot the next time, because there will be a next time. And without your eyes there, I don't know that they'll see it. So that might bring the end to this. But for a while, I think you can run it this way until some major shift or disruption occurs. And then if they don't catch that before it occurs, then that wave of that disruption, some shift in the market, a shift in the relationship with those people, they can be Christians and still decide not to use you.

[B]

Absolutely. Yeah. And we did, we did take steps before the transition of a pretty intensive training program. So like you're saying, you know, to answer those questions where they could be the eyes and the ears and, and do the transactions and have a, an understanding of the lingo that is involved with Roofing and. Yeah, and all of that.

[D]

So.

[A]

Sounds like you got. Sounds like it's working pretty well right now. What's your fear today?

[B]

Well, one is, I think was more, I think the distance. You know, we're 5,000 kilometers away from home and you're not a phone call. You know, I think we can get phone calls. It's just, I don't know, I think it's maybe that, I don't know, the buildup of what it could be pride, I guess, of what's been created and I don't know, it could be maybe outside noises of, you know, that sounds, you know, like a terrible idea, but I think it would be that really just, just maybe losing that or more, I think, because we love, we love our sub crews. They've been working with us a long time. I'm Mexican at heart and my crews are that. And so when we thought of shutting down the business or the idea of shutting down the business, we just looked at, you know, we saw all of the people involved, all their faces, and the revenue that that is generated and that pays and feeds them, which I'm sure they could probably find work elsewhere. But it's almost been this attachment of such a really good work environment.

[A]

You're a good man. You care about your team. That's good.

[B]

Absolutely, yeah.

[A]

And I think the operational aspect, as long as it keeps running the way it is, is doable. It's when it shifts. Next time that bothers me is if they, if they are. Because it's one thing for them to be able to finish your sentences inside of an operational situation. It requires a different level of delegation for them to have vision on your behalf and see the next change coming and knowing what to do with that change. You pulled that off. I don't know if somebody trained to do operations might pull it off. I know they won't pull it off as well as you, but you can keep your finger on the pulse it enough. I mean, there's not any reason with email and phone calls you can't stay fairly involved. It's not that time consuming, so.

[B]

Correct. And we've, we've implemented that. Hey, coming into the new year 2026, regardless of revenue, our, our main focus is to stay, stay connected, you know, once a month, zoom call at a minimum, if not quarterly, and just, you know, checking up the speed on everybody, making sure things are good, you know, what's needed of me so I can prepare. And so we're having these conversations now as we gear up, you know, for the first quarter and actually, you know, starting the first year we moved here to Guatemala March, so I did have first quarter to kind of do all of that before leaving. And so now that we've made this decision, you know, now I think it's just the next gear.

[A]

The distance is not an issue. It's just the, it's the flow of communication and your finger on the pulse of the business so that some major portion of this one of the biggest gears in the cog. If it's wobbling, you need to be able to feel that wobble and you can do that from Guatemala. You don't have to be on site to do that now. I don't expect to see 27% growth annually without you there. If they maintain or slight amounts of growth, I'm going to be really, really, really thrilled with that if I'm you and you should be given, given the situation. So if you can keep it running and stay about as profitable as it is, or get a little bit better, a little bit better and keep these folks all employed while you're taking this time on the mission field, I think that's God's hand and that's a blessing from God that you can do that. And it funds then also your mission work, I'm sure. So you're self funding that in the process. That's not bad at all. So hey, you're a good guy. I like talking to you. Very good stuff folks. Remember, better a wary warrior than a quivering critic. This world needs more high quality leaders, so take courage and lead. I'm Dave Ramsey, your host. Thanks for joining us on Entree Leadership. If you're a business owner who's been grinding it out and rarely gets time to step back and think clearly, I want to tell you about something special. The Live like no One Else cruise is a seven day experience in the Western Caribbean with me and the Ramsey team. This isn't just a vacation. It's an intentional time away to reset your perspective and celebrate the progress you've made financially and professionally. And in 2027, we're bringing entree Leadership at Sea back that includes special entree leadership breakout sessions you can sign up for. Designed specifically for business owners and leaders. You'll get practical teaching, real Q and A and focused time to think through your business with people who understand what you're carrying. Space is limited. Learn [e-mail] events or click the link in the show notes.