How Should I Split My $3.5 Million Company?

Summary

The EntreLeadership Podcast — Episode Summary

Episode: "How Should I Split My $3.5 Million Company?"

Date: October 13, 2025
Host: Dave Ramsey, Ramsey Network
Notable Guest: Wes Henderson (co-founder of Angel’s Envy, founder of True Story whiskey)

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Episode Overview

This episode centers on two main topics:

1. Succession and ownership transition in a family-owned business: Dave Ramsey provides coaching for Dan, a successful electrical contractor, about the complexities of selling and splitting his $3.5 million company between his two sons.
2. Building and sustaining a legacy in a family business: In conversation with Wes Henderson, Dave explores the rise, sale, and rebirth of a multi-generational spirits business, extracting lessons on legacy, growth, and navigating family dynamics.

Both segments offer practical insights on leadership, succession, operations, and how to keep business and family healthy and aligned.

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Detailed Breakdown

1. Succession Planning: How to Split a $3.5 Million Company

Caller: Dan from Indiana (Electrical Contractor, 67 yrs old)
Segment: [00:47] – [15:34]

Dan's Context

• Owned and operated a successful, debt-free electrical contracting business since 1982.
• Two sons actively involved in the business as part-owners (each currently owns 20%).
• Two other children not involved in the business.
• Dan and his wife plan to sell their remaining 60% shares of the company to their two sons over the next two years.
• The sons have complimentary but asymmetrical roles; one leads operations, the other specializes in estimating and safety.
• Key Question: Should I do a 50/50 share split, or something different? How to avoid pitfalls with shared ownership?

Dave Ramsey's Key Insights and Advice

a. Separate Day Jobs from Ownership

• Quote: “The first thing I would do is separate their day job from their ownership.” ([03:42])
  • Each son should be compensated fairly for their specific job roles—ownership and operational roles should be distinct.

b. Fairness to Non-Employed Siblings

• The proceeds from the sale of shares to the sons will go into Dan's estate to ensure the non-business-involved children are also treated equitably.

c. 50/50 vs. Minority Splits

• Pros/Cons:
  • 50/50: No natural tiebreaker. "Anything with two heads is a monster." — can lead to deadlock in major decisions.
  • Minority (e.g., 51/49): The 49% partner has “zero power.” “...if I have 51/49, we’re simply going to do what I say.” ([06:30])
  • Quote: “The downside of 50/50 is...you could get to headbutting and not come to any conclusions.” ([06:24])
• Dave suggests there’s no "perfect" split—each carries risk.

d. The Solution: Robust Operating Agreements

• Create clear operating documents (“operating agreements”) governing:
  • Owner roles vs. management roles
  • Decision-making authority delegated to management/CEO (not across-the-board owner votes)
  • Procedures for major events: death, disability, disinterest, divorce, drug use (“the Ds”)
    • Quote: “You need operating agreements that address all, I call them the Ds…and that's kind of what we're getting into here.” ([09:13])
  • Buy/sell agreements (often with life insurance)
• Quote: “If you leave it vague and it's 50/50, it's going to be a freaking fight.” ([09:38])
• Involve a business attorney skilled in family business structuring.

e. Succession and Leadership Transition

• Transitioning leadership (general manager/CEO) is independent from transitioning ownership.
• Ensure the successor (likely the operations son) is respected by the team:
  • Quote: “Was Daniel elected in the boardroom or on the elevator? Meaning does the team think he can do this?” ([12:37])
  • Announce and gradually increase the new leaders’ visibility and responsibilities to ensure smooth transition.

f. Managing Family Emotions

• Communicate intentionally with all family members (both inside and outside the business).
• Recognize that making the structure and expectations explicit is both a legal and relational necessity.

Memorable Praise from Dave

• “I see how you’ve grown a three and a half million dollar company off the card table in your living room. Way to go. You’re impressive, Dan. Well done, sir.” ([15:10])

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2. Lessons in Growth, Sale, and Family Business from Wes Henderson

Interview guest: Wes Henderson
Segments: [27:47] – [51:32]

The Angel’s Envy Story: Launch, Boom, and Sale

• Wes co-founded Angel’s Envy bourbon with his father post-retirement (2011 launch).
  • Quote: “It was literally me sitting in the basement with my father telling him I wanted to start a bourbon brand. And dad said…sure. And it happened like that.” ([29:23])
• The business innovated with port barrel finishes, breaking conventions and attracting new demographics.
  • Quote: “We knew that the whiskey industry needed a little bit of a turnover...and we felt like we had the expertise and we had something cool and fun to do it.” ([30:00])

Rapid Growth and Acquisition

• Launched in 2011; meteoric sales led to a family decision to sell to Bacardi in 2016.
• Wes credits nimbleness and deliberate branding for their outsized impact.
  • Quote: “We were very nimble. You know, it's not like a big company that's like trying to turn an aircraft carrier.” ([40:01])
• Regrets about selling: “I think we sold too soon…we didn’t need to sell, we had no debt, we had a great distribution platform.” ([41:08])

Tough Family Dynamics

• The death of Wes’s father complicated the emotional and legal context during the sale:
  • Quote: “We did not do a good job of preparing ourselves, be it with making our wishes known clearly, ...and that caused a lot of heartburn with everybody, really did.” ([36:54])
• Lesson: Make wishes known and have documentation in place before the “what if” happens.

The Next Generation: "True Story"

• Wes now partners with his own six sons in a new whiskey venture, “True Story.”
• Each son has different skills, roles, and levels of engagement—requires tailored management:
  • Quote: “You can't put your kids in a box and make them want to be…what they need to be for you. You have to recognize those gifts.” ([43:58])

Core Family Business Principle

• Quote: “To me, it's got to be family first…Family is not always your immediate family. It's your team members. ...Businesses come and go, family's always there.” ([49:44])

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3. Memorable Quotes and Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 03:42 | Dave Ramsey | “The first thing I would do is separate their day job from their ownership.” | | 06:24 | Dave Ramsey | “The downside of 50/50 is...you could get to headbutting and not come to any conclusions.” | | 09:13 | Dave Ramsey | “You need operating agreements that address all, I call them the Ds...divorce, disinterest, drug use, disability, death.” | | 09:38 | Dave Ramsey | “If you leave it vague and it's 50/50, it's going to be a freaking fight.” | | 12:37 | Dave Ramsey | “Was Daniel elected in the boardroom or on the elevator? Meaning does the team think he can do this?” | | 15:10 | Dave Ramsey | “I see how you’ve grown a three and a half million dollar company off the card table in your living room. Way to go. You’re impressive, Dan.” | | 29:23 | Wes Henderson | “It was literally me sitting in the basement with my father telling him I wanted to start a bourbon brand. And dad said…sure. And it happened like that.” | | 40:01 | Wes Henderson | “We were very nimble. You know, it's not like a big company that's like trying to turn an aircraft carrier.” | | 41:08 | Wes Henderson | “I think we sold too soon…we didn’t need to sell, we had no debt, we had a great distribution platform.” | | 43:58 | Wes Henderson | “You can't put your kids in a box and make them want to be…what they need to be for you. You have to recognize those gifts.” | | 49:44 | Wes Henderson | “To me, it's got to be family first…Businesses come and go, family's always there.” |

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4. Additional Coaching: Employee Raises (Bonus Section)

Caller: Stuart, farmer from Colorado
Topic: Structuring employee raises
Key Points:

• Assess raises based on market, not emotion.
• “Unless you are doing something that is an outrageous amount of money, you're not going to get an outrageous reaction.” ([22:00])
• Annual review is important for structure and accountability.

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Key Takeaways

• Document everything: Clear operating agreements and succession plans prevent family and business crises.
• Reduce ambiguity in leadership and ownership: Separate job performance/pay from equity; define major vs. day-to-day decisions.
• Communication matters: Family and team buy-in are essential for a successful transition and healthy legacy.
• Stay nimble and innovative: Small companies can outmaneuver legacy players—if they leverage their agility.
• Family first: Businesses can be bought and sold, but family relationships endure and require intentional nurturing.

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For Listeners Who Haven’t Tuned In

This episode delivers practical, battle-tested wisdom on passing your business to the next generation and keeping your family and purpose intact. Dave Ramsey and Wes Henderson don’t gloss over the challenges—deadlocks, legal pitfalls, and emotions—but arm you with actionable steps, memorable stories, and insightful quotes to help you win in the most important game: business and life, done with intention.

Transcript

[Dave Ramsey]

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 this show, you can fill out the [e-mail] ask or give us a call at 844-944-1070. That's 844-944-10720. Dan is in Indiana. Hi, Dan. How can we help?

[Dan (Electrical Contractor Caller)]

Good afternoon, Dave. It's a pleasure to speak with you. I feel like I know you a lot better than you know me, but we've appreciated your practical invite advice through the years.

[Dave Ramsey]

Well, thank you.

[Dan (Electrical Contractor Caller)]

So I'm 67 years old. I'm an electrical contractor. Since 1982, I bought an electrical business that I was working in with a business loan at 18.2%. That was before I knew what business was. Worked in the field through the day and with the help of my wife, we operated the business side after hours from a folding table in the basement of our home. So we're currently a sub s Corporation. Since 1985, we have a revenue of about 3.5 million with an average of 15 to 20% net. Appreciating the advice through the years, we've been 20 years plus debt free with our line of credit being untapped.

[Dave Ramsey]

Way to go, man. Look at you. You're in a great American success story. Congratulations.

[Dan (Electrical Contractor Caller)]

Well, thank you. Yeah, we've been, we've been blessed through the years. Prior to your influence, we, we were connected to Larry Burkett and Crown Financial, if you're familiar with those.

[Dave Ramsey]

Oh, yeah.

[Dan (Electrical Contractor Caller)]

So we currently have 11 team members. That includes myself and I have two sons that are working in the business. They have each purchased 20% stock in the corporation over the past seven years. We also have two other children that are not involved in the business. And we are in the process of selling the business out of our estate. So within our plan is to sell the current or the remaining 60% shares within the next two years to our two sons that are in the business. And this kind of comes to the question, they complement each other well. They work together well. Their roles and responsibilities in the business are very different. One is project manager and operations manager, has a high profile in the company and the other is an estimator, safety director and does other miscellaneous jobs here in the office with a lower profile. Both are essential. Their levels of Responsibility vary, but they're somewhat difficult determined percentage. So it gets down to the core of the question. As the remaining shares are purchased, how should we be thinking of percentage of shares distribution and pluses and minuses pitfalls of a 5050 share distribution versus something different than that.

[Dave Ramsey]

Okay. The first thing I would do is separate their day job from their ownership.

[Dan (Electrical Contractor Caller)]

Okay.

[Dave Ramsey]

Okay. The day job you get paid for. One gets paid for being an estimator. One gets paid for being the ops manager or future president or whatever. Right. And so I have two children in this business. Rachel Cruz Ramsey personality, gets paid like the other Ramsey personalities. Same schedule of percentages for royalties or speaking gigs or appearances or whatever that John Deloney gets. Okay. Same kind of thing. My son is the president of our company and he gets paid for being the president. And it's a completely different thing that does not affect their ownership. Their ownership is separate from that. And then ownership dictates how the profits are distributed. But the day job, you get paid for the position. Okay. And it could be an indicator into where how to split this up if you want to do that. And so they are paying for these shares, is that correct?

[Dan (Electrical Contractor Caller)]

That's correct.

[Dave Ramsey]

Okay. So then that money is going to go into your assets which becomes part of your estate that will be split among your children upon the death of both of you.

[Dan (Electrical Contractor Caller)]

I assume that's right. Yeah, that's the plan.

[Dave Ramsey]

So that's how the other kids are oak are. Okay. Because they don't. They're not getting anything free and you know that the other kids aren't getting so that the non working, the non in the business kids. So all right, Then that comes down to. Okay, if we have two owners regardless of their position inside the company, what is the best way to structure that? Yeah, even there's no tiebreaker. Okay. And if it's odd, if it's 5149 or anything where one of them is a minority shareholder, they have zero power. So it's kind of all or nothing is the problem because, you know, if I have 451, we're simply going to do what I say. You don't, you don't really get a vote when you're a minority shareholder, technically speaking. Okay. So that's the downside of that. The downside of 5050 is anything with two heads is kind of a monster. Right. So. So, you know, you could get to headbutting and not come to any conclusions. Okay. Then having said that, what I want to do is I want to put in Place operating agreements for them that they are involved in drafting. And I want to say, okay, the owners are not involved as owners in the day to day operation. The owners are involved in setting the tone, the values of the company and the large decisions, setting the vision, setting the CEO in place. But the owners don't need to have an owner's meeting to decide what coffee we buy for the coffee room. That's by the leadership team that included in the CEO. And so we're not going to have a 5050 meeting every time we have to make a decision around here. The leadership team is powered by this operating instructions to make the decision. And the only time you could, the only thing the leader, if you hate the decision and you're the owner, is you could just remove the leader. Much like a board of directors in like a publicly traded company, right? Board of directors represents the stockholders and they put the CEO in place. But the board of directors doesn't walk up and down the hall, hiring and firing, setting marketing plans in place, deciding on products. The board of director puts the CEO in place who puts the leadership team in place that does everything and runs the business. So I want to separate the operations of the business day to day from the ownership in what would be called some operating documents that the young men agree to. And you can help them form that you probably get a good lawyer involved that has done that before, help you put that in place. Also in those operating documents you probably ought to solve for death of one of them, disability of one of them, disinterest of one of them. Because the way you made the decision let them buy in is they were involved. What if they decide they want to quit and go work somewhere else? Do you want them to still have a ownership position? You can decide either one, but you need to address that ahead of time. Divorce.

[Dan (Electrical Contractor Caller)]

Yeah, that don't make sense.

[Dave Ramsey]

What happens, you know, because your, your one son doesn't want to be working with his ex sister in law because the judge awarded her her ex husband's stock. And so you need operating agreements that address all, I call them the Ds and it's usually when I'm addressing partnerships and that's kind of what we're getting into here. But it's divorce, disinterest, drug use, disability, death, all of these bad things that happen have a D on them for some reason. And so if I talked to a young man earlier today, his partner just didn't want to work. That's disinterest. Right. So I would write all of that out in the operating agreements. And we agree to that ahead of time. And in this instance, I would have to buy you out or you'd have to buy me out. In this instance, you know, we do this. And so, you know, if it's. In the event of death, what happens, you could do, buy, sell agreements on that, that life insurance is provided to son A to buy out son B's estate in the event that son B died, and that kind of stuff. So that's the way you keep this from. If you leave it VAGUE and it's 50 50, it's going to be a freaking fight.

[Dan (Electrical Contractor Caller)]

Mm. And that was another question I had. You know, you hear often of your sinking partnerships.

[Dave Ramsey]

Yeah, yeah.

[Dan (Electrical Contractor Caller)]

You know, how. How would a 50, 50 stock split be different?

[Wes Henderson]

Not.

[Dave Ramsey]

The only difference is it's. It's a succession plan. We didn't open up the business as a partnership. So in my case, I've got three owners, all three Ramsey Gen 2 will be the three. They're. They own 33, I own 1%. They own 99% now. So they own 33 each in my case. And that's in a trust. And the trust has the operating statements in it. Okay. Of how they're going to interact. But the good news there is two of them can outvote the other one in the end of the story. And so there's not gonna be this tiebreaker thing that I'm more worried about in your case. So. Yeah, I think I want to address all of that. And what that makes us do is it makes us clarify what the roles are. Okay. It sounds like the operations guy is probably going to end up being the guy running it, the president or the CEO. Right.

[Dan (Electrical Contractor Caller)]

We'll see how that comes together. He has a. He has the larger role at this point.

[Wes Henderson]

Yeah.

[Dave Ramsey]

And probably more of the aptitude, it sounds like.

[Dan (Electrical Contractor Caller)]

Yeah, yeah. Which. Which kind of leads into. Well, we are, according to the assessment that we took on our stage of business, we're. We're at a peak performer and entering the legacy phase.

[Dave Ramsey]

Sounds like you are. I agree.

[Dan (Electrical Contractor Caller)]

Yeah. And then what? Our goal is to transition two years, within the next two years from dad as the general manager, CEO to the two sons who are vice presidents. And would you have any suggestions as far as transferring leadership roles or hierarchy? I feel like we've got a window of time here to work on that, but just wondering if you would have some advice there.

[Dave Ramsey]

Yeah, it's independent from the other discussion. You can keep hundred percent ownership or you can keep 60% ownership. And still do that transfer of power. And it might actually be cleaner. Do that first and then do the. The other, or do the other one first and then do that. But I think you got to get your leadership team in place before you transfer the rest of the stock over. So it sounds like that's a really good thing to do. The biggest thing is that the team believes, based on the actual actions of the individuals involved, that they can do the job. So, like, when my son Daniel moved in the president's role, I was talking to my friend Dan Cathy at Chick Fil A, and we've talked about succession a lot over the years because they've got a great model at Chick Fil a as well. And he said, was Daniel elected in the boardroom or on the elevator? Meaning does the team think he can do this? Would the team have voted for Daniel to be moved in? And I went, oh, 100% on the elevator. And then the operating board decided along and me decided it was time. And that's proven to be true. That's three years ago. But yeah, so it needs to be that when you announce it, it's almost like, oh, I already thought he was.

[Dan (Electrical Contractor Caller)]

Yeah. And I would say we're probably pretty close to that right now. I've been somewhat pulling back a bit, you know, through the last couple years. And so I think that would be.

[Dave Ramsey]

The team sees it coming. Even though you haven't necessarily gone announced it with trumpets, right? Yeah, but I would start announcing it with trumpets and go, this is where we're headed. This is what we're going to do. And probably going to see some changes moving in this way. And you start to let the vendors know, some of the customers know, and. And, you know, lots of communication around it. And then it's. And, you know, and he is proving himself in that role daily. His competence to where everyone's going, you know, this is good. He may actually be better than the old man, you know, which is actually what they're saying around here too.

[Dan (Electrical Contractor Caller)]

But whoever that may be, I hope they are. Yeah. Yeah. And then, you know, and then in light of that, I don't want to create another treadmill, you know, and so that's kind of why we're wanting to give this some pretty. To where, you know, we're seem to be in a good place at this point.

[Dave Ramsey]

You're very wise. Every question you've asked is dead on. I think you've really got this dialed in. And all you're doing. All we're doing here is clarifying A bunch of details. You've got the big rocks, you know what to do and you know, and you've got the right order on things. And now you just gotta talk through, you know, the operating stuff, the feelings around it. But the every bit of the structure that you've outlined is very good. I like it, every bit of it. I think I see how you've grown a three and a half million dollar company off the card table in your living room. Way to go. You're impressive, Dan. Well done, sir.

[Wes Henderson]

Well done.

[Dave Ramsey]

Good stuff, ladies and gentlemen, Good stuff. That's how it's done on purpose. You don't win on accident. Winning is an intentional series of acts, series of touchdowns. And then you look at the scoreboard at the end of the game and we go, we won.

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[Dave Ramsey]

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[Stuart (Farmer Caller)]

I'm doing pretty good. How are you, Dave?

[Dave Ramsey]

Better than I deserve. What's up?

[Stuart (Farmer Caller)]

So I'm a first generation farmer with five employees and we're on track to do about 750,000 in revenue this year. My question for you is, how do you recommend approaching employee raises and how much and how often?

[Dave Ramsey]

Well, when I first started, I avoided doing the annual review where we handed out raises because it sounded very corporate to me and I can't stand corporate crap. The problem was I forgot to do it. And I would look up and it had been two years since somebody got a raise and then they would quit. Well, you never gave me a raise. And I'm like, oh, that's not cool. I was just busy and everything about it. I didn't have any kind of file tickler or anything to wake me up. So we started doing annual reviews. Now, keep in mind, we do reviews every week or every other week because we have a rhythm of meeting for accountability for performance. So we don't wait till once a year to review someone's performance. So the annual review is just a touch point to remind us to address the raise. So that's one time we would give a raise. Is that the annual. At their birthday, so to speak. Their Ramsey birthday. Right, the Ramsey bursary. And so the second time would be if they changed jobs within the company and they got a promotion. And obviously they would need to. We'd need to adjust the pay to the new position that they moved to. And the third time would be if something has happened in the marketplace that that particular job has just gone bananas and we're not. We're no longer paying market rate and we need to up it in the middle of the year because we realize we're way off on that. That one hardly ever happens anymore because we stay on top of it. But I mean, an example of where that might have come up is like back during COVID everything went from $10 an hour for entry level people to $20 an hour for entry level people. And so, yeah, you need to do that or you're gonna lose them.

[Stuart (Farmer Caller)]

Yeah. And I don't know, maybe that's part of what I'm struggling with. I, you know, the average pay for everybody entry starting it's about $20 an hour. And I feel like every time from there going forward, I try to do annual rate. I always do annual raises and I'll even do like thousand dollar plus Christmas bonuses. And I got 401k. Good matching, good 4% matching.

[Dave Ramsey]

Way to go.

[Stuart (Farmer Caller)]

And paid vacation. But, but, and so I feel like I'm trying to be fair to everyone. I, I want to think I am, but anytime I give any kind of raise, it doesn't, it's, I don't know, it doesn't seem to be appreciated enough. Like it's, Everyone always seems to be wanting. I guess everyone always wants more.

[Dave Ramsey]

Yeah.

[Stuart (Farmer Caller)]

In general. But it just makes me wonder if I'm, am I not doing the right amount? Like I give over 7% raises every year, sometimes beyond that and I don't.

[Dave Ramsey]

Know, maybe the amount would be incorrect if it, if, okay, let's say you got somebody and they were $20 and you've gotten them at $25 and you look up and most people around you are paying 30.

[Stuart (Farmer Caller)]

Sure.

[Dave Ramsey]

Then you're 7% irrelevant all of a sudden. Right?

[Stuart (Farmer Caller)]

Yeah, totally.

[Dave Ramsey]

And I don't, I don't know what the Grand Junction, Colorado, you know, labor force demand is. My guess is it's a little bit seasonal.

[Stuart (Farmer Caller)]

Oh, it can be A lot of what we do, we do, we do a lot of greenhouse operations too, along with field work. And so we do some year round work.

[Dave Ramsey]

Yeah, but if you're competing with anyone working around tourism, you know, wintertime, big, big business. Right. Because it's ski country.

[Stuart (Farmer Caller)]

Sure. Yeah, yeah, yeah.

[Dave Ramsey]

And they can go over the ski lodge and make $40 an hour and you're trying to keep them over in the greenhouse for 20.

[Stuart (Farmer Caller)]

Right.

[Dave Ramsey]

That's what I mean. That's the marketplace I got to look at. And so I don't know if that's happening to you or not. It may not be competing for the same labor pool. I don't know, I'm just guessing, but I have landed in Grand Junction and gone skiing, so I don't, I know what it is. But yeah. Anyway, the, Unless you are doing something that is an outrageous amount of money, you're not going to get an outrageous reaction.

[Stuart (Farmer Caller)]

Sure.

[Dave Ramsey]

So a little bit of a yawn is okay.

[Stuart (Farmer Caller)]

Right.

[Dave Ramsey]

Because it's a dollar an hour or a 50 cent an hour or whatever it is. I mean, it's not, you're not saying, you know, you're not announcing that they just won the lotto. So don't expect them to act. Yeah. And so I, a lot of times when we're reviewing with someone, it's a, you know, a reasonable raise, but it's not eye popping. And so the reaction is thank you. Yeah, they don't hate us, but they also aren't doing double backflips and crying and calling their wife and screaming down the elevator about how much money they just got either. Because they did. Because it wasn't that, you know, I have had that happen. But it was a situation where someone got, you know, a ridiculous raise because the situation was ridiculously changed. But the standard annual review raise is based on what the marketplace is paying for that position.

[Stuart (Farmer Caller)]

Okay. Yeah.

[Dave Ramsey]

And that's not going to be, that's generally not going to create an emotional reaction with the team. And even though you're giving them more of your money and your means, you have less of your money and you would like for them to be a little happier about it, it's kind of a yawn. And that's okay because it's not a big chunk of change and, you know, that's what we're facing. So. Hey, that's a good question. It sounds like you're a great business owner that loves his people. You're the kind of small business people that this podcast is for. Thank you for being out there. Stuart. What does the future hold for business? Ask nine experts and you'll get 10 different answers. Economic growth or a recession. Business taxes will go up or down. AI will help us do work or replace us all. But there's no such thing as a crystal ball. That's why more than 42,000 businesses have future proofed themselves with NetSuite by Oracle, the number one AI cloud enterprise resource planning system. Ramsey Solutions uses NetSuite, and you should, too. Whether your company is earning millions or even hundreds of millions, NetSuite helps you respond to immediate challenges and seize your biggest opportunities with one unified business management suite. There's one source of truth for the visibility and control you need to make quick decisions. NetSuite's real time insights and forecasting can help you see into the future with actionable data. And when you're closing the books in days, not just weeks, you spend less time looking backward and more time focusing on what's next. And speaking of what's Next, download the CFO's guide to AI and machine learning at netsuite.com Ramsey it's free at netsuite.com Ramsey thanks for hanging out with us. Folks on entree leadership. So I'm trying to think, it's gotta be 15 years ago or so, I was connected up with a local store owner of spirits. And he said, there's a guy that's famous in the spirits world, in the bourbon world, that has signed a bottle because he listens to you in Louisville, Kentucky on the radio. And he signed a bottle and you need to come by and pick it up. And as a friend of mine owned the store, Tim and I went by and I got the bottle of angel's envy signed by the legendary Wes Henderson. And in the bourbon world, I was just completely. It's like I had a. The rolling stones had signed an autograph for me, and it was pretty cool. And fast forward, just a few months later, they were doing an event at that particular store. Wes was down, and I got to come down and meet Wes Henderson. And he and I became instant friends because I'm such a fanboy, for one thing, of what he does and how he does it, but also he loves business and he loves the stuff that we do at entree leadership. So we had a lot to talk about from day one, and I became enthralled not only with the whiskey, but with the family business aspects and the whole story. Our guest today is Wes Henderson. He's the co founder of angels envy, one of the most innovative bourbon brands of the last decade. One of the most profitable, too. He built angels envy alongside his father, the legendary Lincoln Henderson, who was a master distiller at Jack Daniels and pioneered the cast finished bourbon and creating a brand that changed the whole industry. And after selling that company, Wes turned his focus to a new family venture with his sons, who are also master distillers as well. And the company is now called true story, a whiskey brand built around connection, legacy, and storytelling. So that's what we're gonna do. We're doing a little storytelling. Welcome, Wes. Good to have you.

[Wes Henderson]

Thanks, Dave. I appreciate it. You've come a long way in your bourbon journey. You really have. It's been a joy, though. It's been a joy over the years being able to share bourbon and, you know, sit around and where there's some cigars being smoked, and that's really what bourbon's all about. So I'm really happy to talk about it today.

[Dave Ramsey]

Yeah, it's a lot of fun. And watching you guys, watching your whole journey you've been through, Like, I've watched you do about three or four different iterations of what I mean, you know, you were just barely into the Angels Envy thing. When I met you and I watched you go all the way through that and then the sale of that and then the new, the new startup and what's happened with the boys. The boys are grown up during that time and your sons into the business and become, you know, they're in master distillers and brands in their own right. So take us back to the beginning. I've heard the story, but I think it's fascinating. Your dad, Lincoln, retired from Jack Daniels.

[Wes Henderson]

He did.

[Dave Ramsey]

And how did this Angel's Envy thing then happen?

[Wes Henderson]

Dad was a Brown Foreman which owns Jack Daniels and all those brands for like 40 years. And dad's latest concoction, let's call it, or latest discovery at Brown Foreman was a brand called Woodford Reserve. So that was really a walk off home run for my dad. So dad retired and gave dad some time to chill and relax and realized he was a little bit bored. And that directly led to us sitting down and talking about doing Angels Envy.

[Dave Ramsey]

Yeah. And so talk about the. So you and your dad say, okay, we're going to do Angels Envy. We're going to use his master distilling expertise, your marketing expertise. I guess it's going to come together.

[Wes Henderson]

That's right. And really the way it came together was really cool. And I kind of skipped over that a little bit, but it was literally me sitting in the basement with my father telling him I wanted to start a bourbon brand. And dad said, what dads do? He said, sure. And it happened like that. And on day we had no idea how we were going to get there. We knew it was a long path to entry, but we felt like we were going to embark on it and we felt like we had to be different. And that's what we forged on to do with Angel's Envy.

[Dave Ramsey]

I don't remember seeing a bourbon finished in a port barrel before I saw Angel's Envy. I think that's the first time I ever saw it. Were you the first ones to do that?

[Wes Henderson]

We're the first ones to do it and be successful at it. It happened a few years ago, but like a lot of things, it wasn't the right time for it. It was a good whiskey, but we took some cues from Scotch. We knew that the whiskey industry needed a little bit of a turnover and something to spark things. And we felt like we, we had the expertise and we had something cool and fun to do it. Now it wasn't without some detractors. It was a controversial move when we started it.

[Dave Ramsey]

Yeah. And so talk about the production of that because. And then how you land on the price point because it blew up. It was massively successful, but it was partly because you could produce it in volume, and it was partly because of what you produced in volume, and it's partly because the price point you chose to be in, because in a single barrel world, you all did a blend.

[Wes Henderson]

We did right. I think it was a. It was a very deliberate decision to bring a new style of bourbon to a price point that was affordable, yet it was still super premium. And at the Angels Envy price point. And same with Trustory, we felt like we could bring in people new to the category, yet we could still bring in bourbon aficionados as well.

[Dave Ramsey]

Yeah, well. And, you know, I guess Lincoln's palate, I mean, just his ability to blend those barrels in such a way that it created a generic enough predictable product that it garnered the reputation of just being excellent.

[Wes Henderson]

I mean, Dan had a great palate. That's one thing that I've always noticed, and I think I've been blessed to kind of get that from him. But to create a whiskey that's very approachable and has a mainstream approach that opened up a lot of doors for us. You know, bourbon, the bourbon demographic is expanded and we brought in more women to the category. We brought in younger people to the category. It wasn't your typical bourbon, you know, older guy, you know, male dominated demographic. We brought in a lot of people to the party that weren't there before.

[Dave Ramsey]

So you, you gathered up some barrels, you put you. You finished them in port barrels, you put them in the market. What year was it that that first. That. That first bottle hit the shelves?

[Wes Henderson]

We launched in 2011. We were supposed to launch in 2010, but the barrels weren't ready yet, so. And we weren't going to release anything before it was ready. That's kind of become one of our, our mantras in the company. So in 2011, we came out with the first bottles of Angels Envy.

[Dave Ramsey]

Yeah. And to be clear, the whiskey was already aged. The only question was how long it was going to be finished in the port barrels.

[Wes Henderson]

Exactly. We did what a lot of producers do and still did and still do. We sourced our initial whiskey, we had it produced for us to our standards and our taste profile. And then we would take the whiskey, we would do the finishing in those port casks, we would do the blending, and then we would do the bottling.

[Dave Ramsey]

And that gets the generic hit and gets the flavor profile right where it needs to be and be consistent so that you don't open one bottle and then another bottle. And they're way different.

[Wes Henderson]

Exactly. And that's the. That's the artistry to it. It's. We're taking barrels from all over the. The warehouse from different producers. And it has to be the same every time. It's like the puzzle has to look the same every time, but the pieces are different every time as well. So consistency was really big. And plus, like we were sourcing whiskey that was produced by other producers. We weren't just going to stick that in a bottle and put our name on it. Finishing set us apart. It allowed us to put our mark. And the blending, all that. And there's so much talk about master distillers and I think it's very important. But at the end of the day, the blending is the art form. And it's not just the art form and making it work consistently. It's the art form and innovation. And that's what we're really good at.

[Dave Ramsey]

Well, and something I figured out I was doing a deal with a. Years ago, a guy that had a restaurant ate a barbecue sauce. And the barbecue sauce was great until he tried to produce a thousand cases of it. And we went to volume. The chemistry all changed. It screwed up the whole thing. They almost never got it the same. They never got. He could do small batches in the kitchen at the restaurant and get it just like he wanted it. But when you go to a vat in a factory to do barbecue sauce, it changed the whole deal. You know what I'm talking. And I suspect that you kind of run into the same thing here.

[Wes Henderson]

It's the whole thing. It's the same thing. You know, scalability is so important and keeping on top of consistency and quality and making sure that, you know, you cannot let any drift happen with that product. You've got to be so vigilant to make sure that when you're scaling it, it's being scaled the right way and, you know, take your time and doing it. But I've seen a lot of businesses try to do that and it doesn't always work.

[Dave Ramsey]

So that thing, if it's 2011, the first bottles hit, that's about the time I probably got a bottle from you signed. I mean, you must guys must have been just coming out and so that thing went up into the right hard. I knew it got big, but. But I don't know if I realized it got that big that fast. Cause you guys, it became one of the top, most profitable brands out there by the time that things changed. So then Lincoln passed away at what year was that?

[Wes Henderson]

That was 2015.

[Dave Ramsey]

So you had four years of this?

[Wes Henderson]

We did.

[Dave Ramsey]

Okay. And then you and your mom are owning it at that point, right?

[Wes Henderson]

Correct.

[Dave Ramsey]

Yep. And you guys made a decision to sell.

[Wes Henderson]

We did.

[Dave Ramsey]

And what year was that?

[Wes Henderson]

We sold in 2016 to Bacardi.

[Dave Ramsey]

So it was a five year runs.

[Wes Henderson]

It was a five.

[Dave Ramsey]

And I had in my head this was a decade. That's so wild. You sold it to Bacardi. 2016 is the number public?

[Wes Henderson]

It's not.

[Dave Ramsey]

Okay.

[Wes Henderson]

It's not.

[Dave Ramsey]

Bring it up then. Yeah, I know what it is, but I didn't know if it's public. Okay.

[Wes Henderson]

It was, it was a. It was a good deal.

[Dave Ramsey]

It was a good number.

[Wes Henderson]

It was a good number.

[Dave Ramsey]

It was an incredible number. But yeah. So you got sold a lot a whiskey in five years.

[Wes Henderson]

We did, we did.

[Dave Ramsey]

And the bourbon craze was probably at its zenith also. It's cooled off a little bit now compared to what it was. Yeah, it was like anything you touched that had brown water and it was going nuts. And so. And you wrote you rode that, that horse well. So during that five years, you have meteor. Meteoric growth. Does that put a strain on the family business parts?

[Wes Henderson]

Oh, absolutely. I don't know if the, the strain, I think. Well, there's certainly strain. Anytime you're sacrificing that much, you're spending that much time on a business and you lose work and family balance. I mean, that's always a strain and that's part of being an entrepreneur. You just have to. You got to figure out how to live with that or you're in trouble. I think our biggest issues came probably when it became time to sell the company. And then you've got a tremendous asset like that. You're trying to make sure that that's what you want to do, it's the right time to do it.

[Dave Ramsey]

And now it's with your mom, Right? It was recently widowed.

[Wes Henderson]

That's correct. Right. So I mean, there was definitely some stress. A lot of stress points there. And to this day, I think there's still residual stress points from that. And a lot of that has to do with. I don't. My dad and I did not foresee what that company was going to do. And we did not do a good job of preparing ourselves, be it with making our wishes known clearly, be it with proper documentation, all those things as to what would happen if dad passed. And that caused a lot of heartburn with everybody, really did how old was he? Dad was, I think, 73 when he passed away. Okay. So, you know, he was a melanoma survivor for a long time. I think, though, when dad decided to do this, we knew in the back of our minds that we were going to lose dad probably sooner rather than later. And this was his kind of way of, okay, do something with my son. Let's do something with my grandsons, and let's spend the last years of our lives together doing something fun that we enjoy.

[Dave Ramsey]

So were the grandsons old enough to be involved early in the deal or they came in later.

[Wes Henderson]

One of them was my oldest. Kyle, I think was about 18 at the time. But look, it was all hands on deck with us, Dave. We were filling sample bottles in the garage as a family. You know, when my kids were little, you know, they would help bring the glass bottles over to the table and we would fill them and all those things. So they were already involved. But Kyle, the youngest, was not even 21 yet.

[Dave Ramsey]

And he's a master distiller now, right?

[Wes Henderson]

Kyle is. Kyle is our boy. He's more of a productions director than anything. But the boys all have distillation experiences. But one thing I think I've done a good job with the boys is that I'm putting them in all different aspects of the business. You know, I want them to learn supply chain, marketing, operations, finance, all those things. Distribution, all those things. I don't think we've done as good of a job as we could, but, you know, we're certainly fighting the good fight and trying to make sure they know those things.

[Dave Ramsey]

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[Wes Henderson]

Wow.

[Dave Ramsey]

You became in the, in the spirits world, a household name in five short years, competing against brands that have been around for a hundred years maybe, or a decade or decades anyway. And when you look back on that, you gotta get some absolute things. We did this right? And we did this really Wrong. Give me a couple of those.

[Wes Henderson]

I think what we did really right was, is that we were able to recognize what was happening in the industry. We were able to respond. You know, we were very nimble. You know, it's not like a big company that's like trying to turn an aircraft carrier. We knew we were nimble. We were willing to go up against the big boys. We weren't scared of them. As a matter of fact, I would get excited every time I heard somebody got ticked off about something that we were doing. You know, we're like at the beginning, we're this little lap dog yapping at your leg or whatever and nobody paid attention to us. But all of a sudden I'd hear stories about, people were talking about us, other brands and their marketing meetings and I got excited about that. But I think the biggest, if I were to go back and redo things, and I don't want to redo much because I think if you change any little thing, it's like blending whiskey, you can change 1% of something. Ended up with something totally different. I think we sold too soon. I really do. I think that it was a decision not just made within our family, but with our partners. And everybody saw this meteoric rise of the industry and people start thinking, well, maybe, maybe it's not going to get any better. I think that we definitely, we didn't need to sell. We had no debt, we had a great distribution platform, we had a lot of Runway left, but we had some folks that wanted to exit. So I regret that to this day. Once again, I would never change it because things could have been different, Dave. You know, we could have screwed it all up. But I wouldn't mind having the company where it is now when it's worth a couple billion dollars. That wouldn't, wouldn't stink.

[Dave Ramsey]

I would not hate that.

[Wes Henderson]

No, I wouldn't hate it.

[Dave Ramsey]

All right, very good. So after making the sale, you stayed on a while, worked for Bacardi a bit and then I guess a non compete, I suppose ran out. I would imagine that's normal anyway in that world. And so then you could have just retired. Obviously you had enough change in your pocket. You had a liquidity event. So what pulls you back in and you know, to true story and get this whole new brand moving?

[Wes Henderson]

I think, I think before I get onto the true story, I think a quick note was, is that we had a great acquisition with Bacardi and that's the reason I stayed. It was a really good example of a big company not screwing Up a small company, which happens more often than not. Yeah, right. Especially a family brand.

[Dave Ramsey]

So to their. To their. To their credit.

[Wes Henderson]

Absolutely. To their. Now, now, that doesn't mean it wasn't a 24 hour job for me to make sure those guardrails were up, to make sure they didn't screw it up. But they were smart enough to leave us alone. They knew they had to make rum. We knew that. We knew how to make bourbon. So, you know, those, those ends never kind of came together. Yeah, I could have done nothing. I wasn't built that way, Dave. I don't think I tried some other things. They have some other interest. And our family's been in emergency services for a long time. We've done a lot of those things, which I got a lot of joy in. But I'm a creator and I really wanted to do something with the boys, so it seemed like this might be the thing to do.

[Dave Ramsey]

Okay, so you did something with your dad. Now your boys are doing something with their dad. How's that different?

[Wes Henderson]

Oh, wow. It's a lot different. Number one, I have six sons, so.

[Dave Ramsey]

There'S not a one on one.

[Wes Henderson]

There's a little more. To me, with my dad and I, it was a very interesting dynamic. You know, I really came back to the table with a lot of business and marketing experience. Although I had the palate, I was around whiskey all the time. I knew how to make whiskey. Dad was this legendary master distiller, just a force on his own. But we worked so well together and dad was very nurturing. And dad, I think all dad wanted to do, once again, to work with me and work with his grandkids. I think with the boys, it's a little different dynamic. If anything, just the numbers, you know. So I'm dealing with six kids, all of them with different interests at different ages that have different accomplishments or to reach different plateaus in the business.

[Dave Ramsey]

Different gifts.

[Wes Henderson]

Different gifts. And not. This isn't just in business, it's with your kids. You can't put your kids. If you're smart, you don't put your kids in a box and make them want to be what you think they need to be or what they need to be for you. You have to recognize those gifts. You've got to give them the Runway to do it. And you've got to nurture all of that. And that's part of. It's not going to work if you don't do a lot of that stuff.

[Dave Ramsey]

You got to work at it. There's six opportunities for Somebody to be mad all the time.

[Wes Henderson]

Right, Right. And for the most part, though, I'll tell you what, most of it, especially at the beginning, they would direct at each other. You know, it's that competition amongst brothers. There's those little jealousies once again. Hey, this one's older. Why does this one have more responsibility? Why does this someone get to do this? I'm like, well, this one's been in the company for a lot longer than you have. You know, he's earned that. That doesn't mean you can't achieve that on your own. So it was more, I think, the dynamics between them, but there's also the dynamics with dad, and those change, those shifts. And as they learn more, as they get more responsibility, as I start to learn that they know more and start giving them more. But, you know, and look, Dad's not perfect either, you know.

[Dave Ramsey]

So what was the date the True Story began? What's the official date?

[Wes Henderson]

We launched the brand in October of 2024. So it hasn't been very long.

[Dave Ramsey]

Not even a year old.

[Wes Henderson]

Not even a year old yet.

[Dave Ramsey]

I thought I was around about that time. I thought I remembered that showing up. I know you showed up at an event we were doing about then, and if I remember, I think you sent me pictures of the bottle.

[Wes Henderson]

I did. I was so excited. I had to show you.

[Dave Ramsey]

I was excited to see him. I'm honored to watch from the inside a little bit. That's pretty cool. So I love the brand title because, as you said, so much friendship and relationship occurs around some brown water and a good cigar. And so True Story is a story. I think the underlying marketing touch of that's genius. Talk about how you came up with that.

[Wes Henderson]

One of the things that really made me think about the name True Story is I was at an event in Houston, and we were sitting in, like, a library with overstuffed chairs. And it wasn't a tiny, typical bourbon event where it's an educational seminar. It's just a bottle signing. I had people in a room, 50 people in a room. I sat down in an overstuffed chair in the middle of the room, and we just had a conversation about bourbon. And that really clicked with me. Another thing that clicked with me is when I sign bottles for people, they'll say, I'm not going to open this. You know, I'm going to keep this. And the first thing I say is buy two. Right?

[Dave Ramsey]

Yeah.

[Wes Henderson]

Yeah. You know, that's always the consummate salesperson in me. I'm always selling. But there's so many stories.

[Dave Ramsey]

One to collect, one to drink.

[Wes Henderson]

There's so many stories inside that bottle waiting to be told, and you need to open those. And I like being present, Dave. I think I'm present by proxy at a lot of events. At the end of the day, when you've had a good day at work, a bad day at work, when somebody passes away at a wedding, whatever that situation is, we're there with you to start the conversation. And that's how I look at bourbon. It facilitates those moments that make a difference.

[Dave Ramsey]

Yeah. Yeah, it does. And I guess it's probably the Southern roots of the whiskey that kind of give it that ambiance, that flavor, so to speak. Is that it? It just sitting on the back porch hanging out with some guys, you know, or hanging out with your family or whatever it is, or after, like you said, a long day at work or whatever it is, that kind of a thing. It's different than a typical cocktail in the way it's consumed and the situations it's used in. And that's why I think True Story is a great brand. Great brand. And so right now, you've got the high rye out, and you got a bourbon blend out, right?

[Wes Henderson]

We do. We started out kind of in the same sandbox that we're in before with secondary barrel finishes. I think we do it than anybody, better than anybody else. We've got a bourbon finish and a white musk casks, and we've got a rye finish in amber Ana and sherry casks, and they're very distinctive. Very. The flavor profiles are just incredible, especially the rye. It's off the hook, and we're getting great consumer feedback from it. People love the package. You know, you see that package, and you can't miss it.

[Dave Ramsey]

It's completely different than anything else on the shelf.

[Wes Henderson]

It is. And, you know, then that's scary. You know, it's. I've had a lot of back and forth in my mind on. But it was the same way with Angels Envy. When the Angels Envy bottle came out, it was so different. But you know, what I've learned, Dave, over the years is I think that when I start getting. I find when I'm starting to get uncomfortable, a lot of times, as we're pushing the envelope, that means I'm on the right path, you know, and you have two choices. Either you feel like, okay, I'm uncomfortable with this. I'm scared of it, or I'm uncomfortable enough that I'm going to kind of explore this a little bit more and find out whether or not that's something that could lead to something special.

[Dave Ramsey]

So consummate family business. Now, two different generations, two different endeavors. So that gives you a unique view because there's not a straight line through this. It's a start, stop, start again thing. And so that's a different vibe than a standard legacy handoff succession. Third generation, fourth generation's taking over the business because we had the sale and then a fresh start again. And now with the boys. So when you think about family and business together, what's the one principle you would pass on to the entrepreneurs out there? Because one of the top questions we get are subject matters. Questions that we get is just family business questions all the time on this show.

[Wes Henderson]

Well, and you've always been really good at those discussions. And I've thought about this really hard. And I. I think where I land is that to me, it's got to be family first. And I have to explain what that means to me. Family is not always your immediate family. It's your team members. It's everything else. At the end of the day, as a family unit, your immediate family, I think family has to come first. You have to have healthy relationships because all this bleeds into the business. If you don't have that bedrock of communication, if you're not regularly communicating. We're big on family meetings. You know, we talk once a week now. Do we do it every week like we're supposed to? No. Should we be disciplined enough to do it every week? Of course. And I find out where we start to drift in those relationships is when we're not having that communication. So. And look, people are going to screw up. I'm going to screw up, the boys are going to screw up. But at the end of the day, we have to remember that we're in this together. Businesses come and go, family's always there. But without that cohesive family unit where we're doing the right things. And really, Dave, I want my kids to be good humans. I really do. I want them to be successful. I want them to experience wonderful things in life. I want them to have the financial rewards for working hard and giving them independence, because I believe that brings independence if you're successful. And that's what I want from them. And so family first, that's gotta be it. No matter how crazy things get, no matter how stupid we get, stupid mistakes or whatever, we have to be together.

[Dave Ramsey]

Amen. Co founder of Angels Envy and now the owner and launching of a new brand almost a year ago called True Story Legend in the whiskey world. In the bourbon world, my good friend, Wes Henderson. Wes, thanks for hanging out with me, brother.

[Wes Henderson]

Thanks, my friend.

[Dave Ramsey]

Appreciate it. Good times, good information. Solid stuff. Good stuff. So, 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.