Episode 194: The Hidden Financial Beliefs That Shape Great (and Bad) Leaders

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Preview

Jim: If you don’t mind, I want to read the email. “More specifically, it feels like I’ve reached the end of a chapter where the skills and ideas that energize me simply have no room to breathe.”

Darryl: Once I take inventory of the risk, I am buckling down the chin strap and I’m going. I’m all in, and I am absolutely 100% leaning into optimism, and there’s nothing that’s going to stop me from breaking through. I’m going to continue pushing through the ups and downs, the uncertainties, the self-doubts.

So what was it behind her decision of not wanting to retire? She grew up without money, and her parents were military, and they taught her to be very frugal with money. There was just the way they approached it that was still embedded in her subconscious.

Appreciation of our Supporters

Winston: Hey, before we jump into the podcast, we want to thank all our donors and supporters who make the Today Count Show possible. It’s through your generosity that we’re able to shape leaders through this content and this podcast. Be sure to like, subscribe, and follow wherever you find yourself coming across this content. All right, let’s get to the podcast.

Introduction

Jim: Hey, welcome back to the Today Count Show. Leadership is what I want to talk about today. I like talking about it every day, but it’s not just about vision and people. It’s also about how we think about money. Money reveals what we value. It represents a lot of different things to a lot of different people: what we fear and what we trust. Whether we like it or not, leaders lead from their philosophy of money, whether they’re aware of it consciously.

Today, I am joined by Daryl Lyons, who is the founder and CEO of PAX Financial Group. He’s an author, and he’s a longtime advisor to leaders and families. Daryl helps people navigate not just markets and insights, but meaning—how money, faith, and stewardship intersect in everyday leadership and everyday life. This is a conversation about money. Don’t make any mistake about that. You’re going to want to hang around and listen if money is important to you. It probably should be. But it’s also about wisdom, and hopefully we’re going to talk about that wisdom. So, Daryl, welcome back to the show.

Darryl: Yeah, thank you for having me back.

The Mid-Career Dilemma: Outgrowing Your Role

An Unexpected Email and a Familiar Story

Jim: Yeah, I want to throw you a curveball. I talked about it before we hit the record button, but I’ve been in an email conversation with somebody that I’ve known for a certain amount of years in a different context. And I don’t know if that was seven years ago or ten years ago. I don’t know when it was, but I was working with his company. We met this gentleman, and in the Lead Today community we have a lot of that that goes on. We have a community, and people connect with each other.

I received an email from him. It’s a little bit lengthy, but he’s not a whole lot younger than I am, and he’s in a little bit of a dilemma. If you don’t mind, I want to read the email, and I want to sit with you on it, because I thought about you when this email came in. I’m going to pick up a little bit after his introduction. He said, “I have outgrown my current role. I’m deeply unfulfilled, and I’m more alive when I’m working on the ideas that I believe could genuinely contribute something meaningful to the world. At 62, making a major shift requires faith I’ve never exercised before, and that is both exhilarating and unsettling.

Career Reflection and Identity

A few months ago, I shared a new resume with you.” That’s to me. He’s talking to me. “You may recall that it had some introspection woven into it.” It was actually very creative. I enjoyed what he did with it, “Not just a list of roles, but an examination of what has driven me across my career.” He talks about that in his resume, what fires him up, what he’s accomplished in that sense.

“You helped me illuminate parts of my wiring that I had never articulated, and I’m grateful for that. To be honest, I haven’t marketed that resume, not because it’s poorly done, but because I realized something uncomfortable. I am no longer built to work inside someone else’s system.” I have thoughts about that, but I’ll save it for now. “The thought of stepping into another traditional revenue role, no matter how well-paid or respected, feels like a slow erosion of who I am. It is worrying even to imagine.

Misalignment Versus Depression

This doesn’t feel like depression to me, although I’m sure some of my history and tendencies color the experience. What it does feel like is misalignment. More specifically, it feels like I’ve reached the end of a chapter where the skills and ideas that energize me simply have no room to breathe.”

He plays with words pretty well.

“When I’m working on the ideas that have been taking shape—systems thinking–” I think about this but not the way he does. “A new approach to CRM, I’m always looking for a better CRM,” I have to say that. “Alignment frameworks, buyer ecosystems—I feel awake in a way I haven’t in years. There is purpose, clarity, curiosity, and even joy. When I step back into my current environment, all that disappears.

That contrast is what’s driving this note. I’m not looking for validation so much as perspective. I would invite you thoughts, etc, etc.”

Where do you encounter this, Daryl, in your conversations, or do you encounter this very often?

Darryl’s Perspective: Truth, Faith, Risk Inventory, Optimism

Darryl: Yeah, just over the years walking life with a lot of people. I’ve been doing this since 1999, so I’ve had a chance to walk with a lot of people in career transitions and very difficult life decisions. Sometimes their financial guy becomes the primary thinking partner. Everyone’s different but I’ve encountered similar concerns. I really love that the request is not validation, just perspective.

Jim: “What are your thoughts?” Yes.

A Mentor’s Influence and a Shared Pattern

Darryl: Yeah. There was a man who mentored me for years. His name is Dan Miller, and he wrote a book called 48 Days to the Work You Love. He’s an incredible man. He was a New York Times bestselling author.

Jim: 48 Days to the Work You Love.

Darryl: Big-time book. It did really well. He passed away unexpectedly. He was out of Nashville. Incredible guy. I really enjoyed him.

And his primary business—he had a coaching platform that supported or maybe was the primary driver behind his work as a writer. But having listened to him and conversations, this pain that the writer is experiencing is not uncommon.  It feels, I think to a certain degree, in the way he described it, as a slow death. And I think experiencing that truth and calling it what it is is important. I think many people just discount it and keep moving on, and they don’t realize that they’re slowly dying and they’re not alive. I think expressing that and saying, “This is where I’m at, and this is the reality,” is important.

Faith, Safety, and Risk Inventory

The other thing I heard that was interesting is the expression of his faith that he’s never exercised before. I’m paraphrasing here, and not to imply that he doesn’t have faith and that it hasn’t been exercised in other directions, but I do find it a peculiar paradox in the Christian faith where we tend to—not all of us, but many of us—despite being believers and trusting God, prefer safety. And I think if we take inventory, it is a little bit of an indictment of our faith because if we take inventory of the decisions we make, many times we decide to go the safest route.

And if we really step back and say, “I trust God, and I’m hearing from Him, and I’m validating it through His Word, I’m validating it through the body of Christ, I’m prayerfully considering, and He’s telling me to move this direction,” but I continue to lean into security, I think this is an indictment of faith that is in the body of Christ, and it’s pretty prevalent. I love the idea of him stepping out into an arena that’s a little bit scary, and if it wasn’t scary, it’d be abnormal. But I absolutely love it. Age is irrelevant to me. How old did he say? 63?

Jim: 63.

Darryl: So we’re talking 20 or 30 years of life left, and who knows how many of those are working. It could be a day. It could be 20 or 30 years. And so the idea of leaning into something that allows him to come alive, I absolutely love it. Like, 100% love it.

Leaning into Optimism and Assessing Risk

The Pragmatic Side and Taking Inventory of Risk

What’s the pragmatic side of this? Of course there’s bills to be paid, and there’s potentially spouse and family involved that have to be a part of this decision-making process. So as I think about the pragmatic side, I think about the way I process business decisions because even as an entrepreneur, I have different divisions of business. I have nonprofits I run. And so it feels as though every day I’m starting a business because I have to make decisions that have consequence—potential consequence. That means the consequences of me being embarrassed, of making mistakes, of failing, of losing money.

And so the first thing I prefer to do whenever I make a decision is to assess the scope of the risk. When we assess the scope of risk, we often find a way—do we hedge it? Making sure we have enough cash. Do we manage through it? Do we get in front of it? In other words, having conversations with people, saying, “This might not work out, and here’s what we’re going to do if it doesn’t work out.”

Leaning Fully into Optimism After the Assessment

All that to say is once I take inventory of the risk, I am buckling down the chin strap, and I’m going. I’m all in, and I am absolutely 100% leaning into optimism, and there’s nothing that’s going to stop me from breaking through. I’m going to continue pushing through the ups and downs, the uncertainties, the self-doubts, and I am absolutely going to find a way on the other side.

And I think the reason I like that approach is because many people jump in, and then they have these degrees of hesitation along the journey. They’re hesitating. I’m just getting all of that out up front, and then I’m leaning into optimism no matter what. And I think those that actually lean into optimism end up doing the best. And I’ve seen that over the years many, many times over.

It’s those that have hope, that have optimism, that push through the self-doubts, that are consistent. And a part of that is casting a vision and designing a strategy, which is what you’re an expert in. But without knowing all the context, I love this mentality—starting with truth, and then taking inventory of your faith, and then leaning into something that’s giving you life. Yeah, it’s a long-winded answer. Sorry.

Jim’s Reflection on Safety, Confidence, and Forward Motion

Jim: No, it’s good. I think the email deserves that, I like your perspective. I know a little bit about the author of this email, and I told you that before we started the podcast, and I’m going to bring that up here in a minute because it might have some bearing as to why he’s thinking the way he is and the way he’s moving the way he is.

But as you were talking, before I jump into that, I did think of two sides of this argument. Let’s call it an argument. You’ve got the safety thing. Those motivational speakers love pulling out the story about “burn the boats,” right? I’m sure you’ve heard. Yeah, burn the boats. But some of us are just not wired to burn the boats. If we’re burning the boats, we make it look like we’re burning the boats, but we’ve got a couple others stashed somewhere in the weeds. It’s kind of where we’re at.

But I think what I want to agree on is that the positivity, the moving forward, the energy that you’re putting towards one thing is going to bring you a return on that investment. It just will. That’s how God created everything.

I think about golfing. When I’m about to release a putt, if I have questions in my mind about the line that I’ve chosen to putt and the speed, if I have questions in my mind, that putt is disastrous. But even if I’m wrong, and I’m sure that I’m going to go with what I’m seeing and I putt it with that confidence, even if I’m wrong, that putt usually turns out better than the one where I’m second-guessing myself, right?

But I’m going to pull up his–

Darryl: Some context.

Temperament and Soft Skills (INTJ & Working Genius)

Background on Myers-Briggs and Temperament

Jim: Yeah, some context. So, in Myer Briggs, for those who are not aware, it’s probably one of the oldest, if not the oldest, temperament assessments that’s been out there. And actually, you’ll find hints of it in Ezekiel chapter 1. It’s a bizarre text there, but the prophet has a vision that God has given, and humanity is described in four ways. And lo and behold, it’s very similar to the four major types of temperament in the Myers-Briggs.

Carl Jung used it before it was called Myers-Briggs and whatnot. But anyway, real quickly, I don’t often see the results. And just for your sake, since you’re with me here, D, I’ll show you his results.

There’s eight different letters that we can choose from the Myer-Briggs. It’s E, I, S, N, T, F, and J, representing extroversion, introversion, intuition, sensing, feeling, thinking, judging, and perceiving. Just real quickly, the way that words evolve, what our current culture calls judging a bad word. It’s really a good word in its original context. Normally, if you’re a person who is wise, you’re a person of sound judgment. That’s kind of the idea behind it in its original sense.

The INTJ Profile and Dominant Traits

What I’m saying is unusual about his temperament is how dominant each of the four letters that has come out for him, which is an INTJ. The way that I illustrate that with letters is if somebody is an introvert but not a massive introvert, then I would illustrate it by writing a lowercase i versus an uppercase I. If that makes sense. In his case, if I were to write his four letters, they would all be uppercase: I, N, T, J.

What does that mean? Well, the NT, we pull out rational. So he’s very logical. When you throw in the other two bookends, the I and the J, we call it a mastermind. So he’s a rational mastermind.

When I pulled up the other part of his assessment, the scary thing, and I mean that with all humility and respect, is the people side of who he is: the sociability, the empathy, the extraversion. Not a natural place. So he is kind of like a scientist. He’s like that guy. When he mentioned processes, systems, CRM, all of that, I’m going, “Yeah, that sounds–”

It only made me think of one other thing. Are you familiar with Patrick Lencioni?

Working Genius and Natural Strengths

Darryl: Yeah, I’m a huge fan of The Advantage. In fact, he just did a call the other day. I listened to it. It was fascinating. He’s great.

Jim: And it’s called Working Genius, right?

Darryl: Yeah.

Jim: I just deleted the tab I had open. Here it is. One of the other things I thought about here was and I don’t know. He can go on to Working Genius, and I think the assessment is pretty cheap, but it can kind of validate what he’s thinking.

Of the six working geniuses—wonder, invention, discernment, galvanizing, enablement, and tenacity—I’m going to guess that invention’s a no-brainer. He definitely has strengths in the invention side. What I’m not sure of is whether his other genius is wonder or tenacity. I’m wondering about that.

With that said, you’ve given some advice, but any other thoughts?

The Missing Piece: Communication, Sales, and “Transfer Confidence”

Early Struggles, Social Skills, and Sales Reality

Darryl: Well, the INTJs—I don’t recall mine, but I think mine’s similar to his.

Jim: Probably. I would guess that.

Darryl: I really had to work on that social skill. When I first got in the industry, I took an industry assessment and I didn’t pass.

Jim: What does that mean?

Darryl: I know, right? They weren’t supposed to hire me. And they didn’t say I had the skill sets to be good in this industry. They let me in because they had to meet a quota. They were recruiters. And it was the end of the year. They said, “Okay, the minimum standard’s ten. You got a nine. Close enough. We’ll let him in.”

I struggled. And I almost got fired in the industry. I found a client, and this was God. That client gave me enough revenue to meet the contract requirements.

I would say this is obviously not impossible. Many people have had success with that profile, but the reality of that deficiency, for lack of a better word, needs to be addressed. Pushing through the discomfort of the awkwardness, there are plenty of resources to shore up those sales skills. Once you develop a sales funnel and think about the steps in a sales process, marketing, and prospecting process, sales is just a transfer of confidence.

You may have the skills to solve a lot of problems through a CRM. We use Salesforce, by the way, as a side, which is a complex system.

Sales as a Transfer of Confidence

Jim: It’s very complex. You usually need a lot of consulting to get that working for you the right way, don’t you?

Darryl: I have somebody full-time on it. It’s a heavy lift. The reality is, even if you are a good consultant and can solve problems, you have to be able to transfer confidence. You have to find a way to shore up these deficiencies.  Knowing that, this is not an insurmountable task. There are plenty of people out there that can work with somebody like that to make sure they can transfer confidence. That includes uncomfortable roleplay.

I used to role-play a lot. I remember once I was so nervous about making calls for clients that I put a sticky note on my phone that said “coward.” That was my hack. I hacked my way through.

Jim: Isn’t that interesting.

Darryl: In the initial stages, it doesn’t matter how good he is or how good of a systems person he is. If he can’t transfer confidence, it’s going to be hard for him to succeed. It’s almost as thought the first two or three years, it’s really focusing on shoring up communication and sales skills and living in that discomfort, and that’s okay.

Living in Discomfort and Building Communication Muscles

Jim: It’s funny you put a Post-it that said “coward” because I did something same thing. Mine was just a little different. Once I realized that I felt that a big part of my calling in life had to do with communicating—preaching, teaching, and coaching—I also learned by just looking in the mirror and getting feedback that I have a serious countenance. On all of my outlines, I often draw smiley faces just to remind me to smile.

Darryl: That’s good.

Jim: We all have little nicks in our armor. I think I’m very happy sometimes, but if someone takes a picture of me, when I’m supposedly very happy, I’m going, “I’m not sure I look very happy.”

Darryl: Yeah, exactly.

Temperament, Character, and the Need for Support

Jim: So I had to tell my face. I guess where my advice is that I agree. I would encourage this friend to face this reality. You have to remember I’m very interested in humanity. I’m curious about humanity. I don’t usually look at what’s wrong with somebody.

Darryl: Are you talking about humanity as the greater ecosystem of people communicating or an individual person?

Jim: Individuals. What that does is that overflows into teams and cultures. I like starting with the leader and getting inside the leader’s head and heart. I have a little triangle that I use. We don’t have time to get into that today, but the real quick overview is, what I’ve come to believe in my theology / psychology, my integration of theology and psychology would be this, your base is your temperament. I believe God gave you a temperament at conception, and it’s never going to change.

What’s built on top of that is your conditioning. Your conditioning is everything that’s happened to you in life, you good, bad, and ugly. Then there’s one more layer, last layer is your character. The good news is that all of us can transform our character.

Then it comes back to what I’m going to do with my temperament and what I’m going to do with what I’ve gone through, good, bad, or ugly, and partnering with God and pushing that out on the other end. Being the character, behaviors, and belief systems that I want to have.

The other thing I would say to this gentleman is that though you are super smart, the area you are not as smart, let’s just call it people smarts, you have to get coaching there.

Support Systems and Finding the Right Environment

The other things is you’ve got to surround yourself with some sort of support system. Going back to your earlier comments about, you got to stay positive, you got to follow the plan, you got to stick with the plan, you need a squad that cheers you on.

I’ve noticed something about my grandson. He’s a very good swimmer in high school, and he swims a little tiny bit faster when he’s swimming on relays with his team. There’s a team thing in him where he doesn’t want to let his team down. I’m more independent than he is.

My summary on this and then we’ll move on. Obviously, a brilliant individual who can solve a lot of problems. I’m not sure he should check out of somebody else’s system as he labeled it. Maybe he needs to find a place where his way of thinking, going back to Patrick Lencioni, the Working Genius. If he hasn’t looked at that, I’d encourage him to do that.

Darryl: Yeah, it’s great.

Jim: I think he’d be encouraged by that. There has to be organizations out there, software companies, etc that would love to have him on the team. Wouldn’t you think?

Darryl: Yeah, that’s a good point. He could find an environment where he can find that life again, I’m sure. With remote work today, it’s more possible.

Retirement Reframed: Age Is a Number, Purpose Isn’t Over

Jim: The last time you were on the podcast, I recalled we had a significant conversation about how retirement is culturally being redefined. You even help people think through what retirement looks like. In other words, what I’m trying to say is, you’re 63. It’s not a cliché. It’s really true. It is just a number. If you keep yourself healthy, does that make sense?

Darryl: Yeah. Retirement was initially defined in the ’40s. Before that, Germany created the first pension. At the time, you have a pension adopted at 65 with life expectancy at 67. It wasn’t much of a financial obligation for a country or annuity company to pay out something only maybe in two to ten years.

Now, some people are retiring sooner and living really long. We’ve got to set aside what we might think 65 means because it has absolutely changed. There’s more work for God to do in and through those people that are beyond 65.

Purpose Beyond Traditional Retirement

Jim: It can look different, but it doesn’t mean you have to do the traditional, I’m going to take five strokes off your golf game or play bingo or whatever it is. The last thing I want to say and then we’ll transition, meeting with this gentleman one-on-one, I was very fond of him. A lot of our conversations were about interpersonal issues in the workplace.

Being that I am an INTJ, not to the extreme that our friend is, interpersonal skills did not come naturally for me and still don’t, really. I think the reason he and I connected is just truly because over the years God has given me a curiosity and interest in others. That might be a path that he may want to work harder on in the beginning on that path. It has certainly helped me.

Reset the Conversation: Books, Background, and Money Imprints

All right. That was great. You, yourself, have written I think four books.

Darryl: Correct.

Jim: Yeah. Four books: 18 to 80 Life Stage Thinking About Money, Small Business, Big Pressure, I love that title. It’s about leadership and stress. The Grand Money Chasm, the picture that you have on that cover I think says something about generational health maybe. At least that’s the picture that I got there. Then, Biblical Responsible Investing. I think I have a couple books in my library and I have read one of them already.

Darryl Lyons’ Background: Money and Childhood Imprints

Let’s reset the expectation here. We’re going to talk about money, leadership, worldview, and stewardship. Let me throw out a question. I want listening people to know a little about you first, a little bit about your background. We don’t have to stay on it forever, but what did you absorb about money growing up, spoken or unspoken, and how does that shape you today?

Darryl: Sure. My mom had me when she was 16, and my dad was 20. It wasn’t easy for them to find their footing financially. My dad did very well in a fire and safety business, but in the ’80s, if you were specifically in Texas in the ’80s, ’87, there was the S&L crisis, the savings and loan crisis that took place. Oil–

Jim: When was that?

Darryl: About ’87. The market had a big crash. They called it Black Friday.

Jim: I worked for Bank of America in those days.

Darryl: In the pyramid building?

Jim: Yes.

Darryl: That was a tough time for a lot of people, my dad included. That seemed to be an important imprint on my mind that I made a decision at a young age that I didn’t want to work for somebody because he was let go, and it impacted our family. I grew up, money was just uncertain. There was extremes. We had food, and we had–

Jim: Did you talk about it as a family?

Darryl: No, not really. It was just, “We don’t have money.”

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Emotional Weight of Money and the Pursuit of Mastery

Darryl: You’re 16 and you don’t have auto insurance. It got to the point where, it’s funny now, we got a new car and we didn’t have the money for the title. We had the temporary title, but that fades, so I learned how to color it in so it would last longer. Just little things like that.

I remember edging the mobile home, the skirting, and if you get too close when you’re edging it, it’ll crack the skirting. That’s when, in my mind, I thought, I really want to have a house with a foundation. There are just these little things.

Jim: When did you realize the emotional weight of money, or a lack thereof?

Darryl: Yeah, it’s a good question. I think as a kid, sometimes it comes off a little embarrassing, it’s probably easier if you’re around a lot of other people that are struggling. There were times in Boerne, Texas, we lived, and that was a community that tended to have a little bit more. At the time, they weren’t wealthy, but when your peer groups see that you don’t have things and people say stuff, that’s when it becomes a heavy thing for a young kid.

Then probably about 18, there was this pursuit of mastery of money that happened pretty early. I worked at a bank. That’s how I paid my way through college. I studied accounting and finance and started in the industry in 1999. I went on and got my master’s at A&M Law School and have been studying this. A student of money ever since. I find it fascinating, the collision of money and scripture. I’ve enjoyed the journey of studying, and it never ends because it’s not just a math equation. Very much of it is not math.

Money is Not Just Math: Behavioral Finance

Jim: When did you begin realizing that it wasn’t just about the actual dollars and numbers, that there was much more underneath?

Darryl: Yeah, it’s tough because I still default to the dollars, but then I realize that humans aren’t rational.

Jim: Yes. We think we are.

Darryl: It’s hilarious.

Jim: Right? Do you think this is a true statement? We think we’re rational.

Darryl: We really do. We have this overconfidence. Underneath this facade of money confidence exists a family story that’s really driving the decisions subconsciously. Something that happened in childhood that is really the driver of how decisions are made. It’s not a spreadsheet that ultimately dictates the future. It’s some weird event that happened.

Family Stories Beneath Financial Choices

As an example, a lady I was guiding financially to retire, there was no money issues at all. Economically, she checked all the boxes: lots of zeros, multiple millions, plenty. She would not retire. Her health was problematic, stress, marriage, everything. The rational side wasn’t making sense to me. But if you dig deeper, and we had conversations over tears, because to go here sometimes is painful, you recognize that–

Jim: To go to the source.

Darryl: The source.

Jim: Not the future, not even the reality of the numbers, but the deeper things.

Darryl: It’s been a journey for me to accept that that’s the reality because I like to spreadsheet things out. If it makes sense, it is what it is. But here, we had somebody that wouldn’t accept the data. I can run data just like anyone else in probability scenarios. So what was it behind her decision of not wanting to retire? It wasn’t financial security. In fact, all the evidence suggested her health and her marriage needed her to retire.

It was rooted in the fact that she grew up without money. Her parents were military, and they taught her to be very frugal with money. That was just the way they approached it, it was still embedded in her subconscious and part of her decision-making. We had to acknowledge that. It wasn’t as though I was going to overcome it. We just had to recognize it.

Jim: How did that come out? A sense of guilt and shame that she had money?

Behavioral Finance in Practice

Darryl: Not a sense of guilt and shame, just the desire for more economic security. You just don’t have enough. This happens a lot. If you model out somebody’s financial future, we can get to a place where we accept that reality. For example, if I were model out your financial future and say you have a 99% chance that you won’t run out of money, and we accept that, getting to that place is actually beautiful. Then you can make decisions that have wonderful long-term value.

For example, somebody with a high probability of not running out of money can take some of their money and shift it aside, give it life by investing it accordingly so it becomes an inheritance. I’ve taken you through a journey but let me map it out for you just a little bit. I’ll take somebody through a rational process of going through an economic forecast. Whether or not they accept that rational forecast, maybe I’m guessing, 10–20% of those people won’t accept that rational forecast because there’s something underneath them that’s not allowing it.

Jim: Interesting.

Darryl: What I have to do is–

Jim:  In the sense of believing it or not believing it?

When Security Needs Override Forecasts

Darryl: Yes, that’s right. I’m dealing with a spouse, a husband and wife. One of them could have a hard time accepting that reality. The consequences of not accepting that reality are problematic. As an example, this person said, “I just don’t have enough security. I need more.” Maybe it was five million. I don’t remember what she had. In her mind, she needed ten million. It didn’t matter. It was a nebulous number.

My point is that I take somebody through a rational thought process and then find out along the journey that they’re irrational humans. I’ve got yo find a way to dig at the source. If I can’t get them to accept the reality of math, then the decisions they make can be consequential.

What Makes This Approach Different

Jim: Do you think this differentiates what you do from, not that we’re going to bad mouth other advisers but, do you find that this kind of unique for you?

Darryl: Yeah, it is. We’ve systematized it. It’s rooted in behavioral finance, which a collision of neuroscience, psychology, and traditional finance. I was mentored by a guy out of Harvard who guided me through this process. We adopted technology similar to Myers-Briggs, but it’s specifically rooted in work done by Daniel Kahneman, Thinking, Fast and Slow.

Jim: When you model things out, correct me if I’m wrong, it’s not just the numbers, inflation, if you get this return on investment. It’s based on needs and wants as well. Is that right?

Darryl: Oh, very much so.

Jim: On the expense side of things, whether they want to travel or are homebodies, whether, to your point, whether they want to build generational wealth and leave an inheritance.

Darryl: It’s insane how many different opinions people have on this. I try not to be dogmatic. I’m an expert at my own opinion, so I can tell them what I think they should do, but navigating that and getting husband and wife on the same page.

To answer your question, the tools that we use, if there’s one thing we try to implement is making sure the non-CFO spouse has a voice. That’s lost in the industry as a whole.

Worldview, Stewardship, and Serving God vs. Money

Jim: That’s good. Back to another point that you’re making about getting down to it. I find that in my psychology, when we start talking about money, I still struggle with it today, to be frank. It’s not my parents. It might be the culture or what I heard growing up. I’m going to call it religiosity. I’m not talking about accurately exegeting Scripture,  but I’m just going to talk about religiosity. Sometimes what is projected.

When I have a nice thing, whatever thing it is, it could be a simple thing, could be a $100 thing, but it’s a luxury, I have to fight guilt. And yet I have this desire to provide, and so I can only imagine, I’ve worked with couples and individuals who have looked at me, clenched their jaw and their fist, and have said even things like, “I grew up poor, and I will never be poor again.” But they’ve never really defined that, and so it drives them off a cliff. So that’s good.

Worldview, Entrepreneurship, and Hidden Drivers

Well, I think kind of what we’re talking about, we can step right into this, is whether they realize it or not, that is certainly part of their worldview. A lot of people don’t want to use that term worldview, but when you look at what you have learned growing up and making this transition as an entrepreneur. I like how you said that, because I kind of had that little thing happen to me too, because I forget what happened, but one of my devils, which is sometimes a good friend who just exposes things that you didn’t think about, and now you’re starting to think about it. So, in a humorous way, they become a little devil.

Darryl: Yeah, I understand.

Jim: So I had a friend have me put on a spreadsheet how much I made the bank, how much my work profited the bank. And that was a really bad thing to do, because I found out in one year, and I don’t remember the numbers now, that my actions, my work, netted the bank millions and millions of dollars because of lending millions and millions.

Then, in the mid-80s, looking at my salary to what I made, it was less than double digits in the percentage. And so I said, “I’m out.” And I didn’t leave that day, but I said, “Okay, I’m out. This doesn’t make sense.” Plus, there was a filthy side to some of it that I felt anyway, a dark side to the banking world that I have a hard time articulating, but I felt it.

Formative Experiences and the Question of Stewardship

I remember one summer I worked at a machine shop right out of high school, because you’re right out of high school and you’re trying to make money, and you’re not really saying what’s the best job, you’re just getting the job. Yeah. It was actually at a machine shop that my uncle used to run. And I would go to work, and I would come back filled with oil, and literally most of the time the lifespan of those clothes wasn’t very long. I’d have to take them off, throw them in the bathtub, because there’s no place to put them. Yeah. And then I’d have to get cleaned up.

I’m exaggerating, but sometimes that’s how I felt as a banker coming home from work. There was just something about your life being surrounded by all of these things. I remember elderly people would come in, and they would fight me for an eighth of a percent for their CDs, and would even swear. And I’m going, “My gosh, these people are wound up so tight.”

But here’s my question. Whether we realize it or not, and particularly every leader, they work from a worldview. How has your worldview evolved over time, not just from your own childhood experiences that you alluded to, but all these stories that you could probably tell of helping people?

Serving God vs Money: Fear, Giving, and Spiritual Tension

Darryl: Yeah. I think part of humans is to discover God. That’s part of what we do. I think it’s understated. We discovered math. Math was already here. We just discovered it, right?

Jim: That’s good.

Darryl: We discovered radio waves.

Jim: I’ve never really heard that before. I like that. Math was already here waiting for us. It just took us a while.

Darryl: We discovered AI, artificial intelligence. We’re discovering a lot.

I think a beautiful thing about our, you know, we’re not pursuing God; God’s relentlessly pursuing us. He’s always there, never leaves us, never forsakes us. We discover Him through His Word and through engagement with the body of Christ. That discovery process has been a journey of a worldview abiding in Him, and the overflow of abiding with Him is clarity on what He wants to do in and through me.

That has changed quite a bit, mainly because I’m in a different position than I was in my teens and twenties. As I take inventory through prayer, what does He want to do? My worldview is often defined by the mission statement that I create.

Mission Statements and Personal Calling

Jim: Do you have that memorized?

Darryl: Yeah. I help others believe in a bigger life.

Jim: Wow. Yeah.

Darryl: “Help others believe in a bigger life” is important because it’s flexible enough in nature to have a secular tone.

Jim: What I like about that is it, you’re making me want to adjust mine now because even though others is plural, it felt more personal than mine. Mine has to do with shaping leaders, but it feels a little more corporate than yours does. Yours feels more personable. I like that.

Darryl: Well, thank you. I honestly never stress tested it. This is what God put on my heart.

Jim: Well, I’m a critic on mission statements and purpose statements, so I think that’s outstanding.

Scripture, Stewardship, and Organizational Purpose

Darryl: Well, a little story. We had a mission statement as a company that we had evolved as a company, so we needed to revise our mission statement. And we hired a consultant, and he was a great guy. We paid him a lot of money to do some consulting work, and we adopted a new mission statement. We took it to a peer group to criticize, and they said, because it had kind of American stuff in it, it sounds more like a Trump rally cry than it does a mission statement. So I said, “Okay, well that’s not going to work.” And I decided we need a mission statement. We don’t have one. So here’s our mission statement.

I told my team, “Here’s our mission statement. Our mission statement is: we exist to 1 Timothy 6:17–19.” And they go, “What is that?” I go, “Command those who are rich in this present age not to be arrogant or put their hope in wealth, but command them to do good, to be rich in good deeds, to put their hope in God so that they may give life to others and they can take hold of the life that is truly life.” Little paraphrase at the end, but that became our mission statement for about two years.

That was our guiding light because that was our default. And then we’ve since massaged it to create something that’s a little bit more packaged, but it still defines the way I think about things. Yeah. 1 Timothy 6:7–9.

Jim: But you’ve done a great job summarizing it. It’s high level. You probably have a narrative that you’ve written underneath that, I would imagine. That’s really good.

High-capacity leaders + serving God vs money

So, high-capacity leaders. I had a friend of mine say something to me the other day that I don’t want to give too much detail on because it’ll give away his identity, but he’s kind of new in the faith. He’s very successful, makes a lot of money. When you have a lot of money, you have a lot of options. You often have these revenue streams, especially entrepreneurs.

A lot of corporate guys have what I’d call revenue leaks, where they spend more than they need to, more than they can possibly consume. I’ll leave it that way, and you can use your imagination as to what that may be. There’s money going out, but they don’t even get to consume what their money is going toward. It’s impossible to do.

So what do they believe about money, and where do you think high-capacity leaders go wrong with this whole thing of money?

Serving God or Money: A Spiritual Divide

Darryl: Well, it’s scriptural. This is very important. I believe you can love the one or hate the other, be devoted to one or despise the other, but man cannot serve both God and money.

Jim: Repeat that all again.

Darryl: We can be devoted to one or despise the other. We can love the one or hate the other. But man cannot serve both God and money. It’s polarizing. I’m suggesting that you’re serving one or the other.

Jim: Which informs which.

Darryl: Oh, that’s a question?

Jim: It’s a statement.

Darryl: I was going to ask, a question mark or period because I–

Jim: Yeah, same.

Darryl: So that’s really interesting. If you were to say, “Wait a minute.” And my life is dictated by money because I can look at your transactions.

Fear, Giving, and Trust Beneath the Numbers

Jim: Let me interrupt you only because we’re on the same page here. So let’s go back to that. You’re going, “Wait a second.” You’re going, “Okay. Is that a question or a statement?” I’m going, “Okay. Well, actually, let’s play that out.” If I tell God, and I’m probably not saying it audibly, the typical person thinks it. And if they’re not thinking it, their behavior is even more telling. But if I say, “I’m going to give this amount to this church or to this ministry or whatever,” if you hear that, that still sounds like I’m in charge. Right?

Darryl: Yep.

Jim: And so it’s almost like I’m putting God in a place where He says, “Oh, thank you, Jim. Thank you. Thank you, man. We needed that. We really needed that.” To your point, it’s not an “and,” right? It’s not one drives the other.

Darryl: It really isn’t. I think that’s where we kind of live in this lukewarm kind of space. And so it’s so interesting when we hyperfocus on God and let the overflow of our relationship with Him dictate our money decisions. I’m not saying that it’s going to be smooth. It’s very much a process, and there’s a lot of tension that exists here.

Jim: We’re insecure sometimes. What is God saying, right? We don’t always know 100%.

Spiritual Tension, Wealth, and Abiding in Him

Darryl: Sometimes it’s Chinese food, sometimes it’s God. Yeah. Right. But I get a chance to ask a lot of tough questions because I get to see people’s financial statements, and I can ask them about their giving. As a body of Christ, giving as much as we talk. But if I were, as an example, a very successful business owner—I talked to him the other day—and I called him out in a very tactful way about his giving. We have a good relationship, and his comment was, “It’s hard for me to transition to giving because I have so many obligations now.” I think that’s a great starting point, but it still doesn’t answer the question: who does he trust?

Fear, Trust, and Giving Decisions

Jim: So let me ask you: is it fear? Is it comparison? Is it scarcity?

Darryl: Yeah, I think it can be any of those. Even as you mentioned before that you struggled with nice stuff because the idea that having nice stuff is problematic. You can even ask yourself, is that rooted in your own concern about having nice stuff, or is it more of a concern that people are going to see that you have nice stuff and say something about it?

Jim: Oh, that’s absolutely what it is.

Darryl: Yeah. Okay. So it’s so nuanced, right?

Jim: I’ll tell you this right now: I don’t like crap. I like really nice stuff. I’m also somebody who believes that things should be done in excellence. My dad told me that he affirmed what I’m doing in my life, but he said, “One thing that you probably should have been was a Division I NCAA basketball coach,” because there is just something about playing games that I believe demands perfection.

I’m a little loony in that way. And so perfectionism has a religious overtone to it psychologically when you think about it. And I can’t be perfect. That bothers me. I can’t have something nice but be pure about it because I don’t want to be accused of something that’s not true. Or is it true? And so you’ve got all those things going on in your head.

Abiding in God and Navigating Money Conversations

Darryl: That’s right. And it is tough to unwind. The good news is we have the Word of God as our framework. There was a minister that said, “We don’t have any problems. We just have people.” Meaning that if we unpack what he was saying—I don’t recall his name—I believe that having thinking partners to discuss these money issues, other believers, is really healthy.

Unfortunately, pastors are stuck in this situation where it’s hard for them to discuss money issues because they feel like it’s going to jeopardize the relationship between the pastor and the flock. So I feel that part of my role—and there are others; I’m not by myself—is to illuminate what God wants to do in and through people around money conversations. And it’s not black and white. It is very nuanced.

You alluded to relationships with parents and perfection and all the stuff that comes with money. It’s so challenging. And so that’s why my suggestion isn’t one to say, “Here’s how it’s done.” It’s more, “What’s the source of truth?” What I find is that those that abide in Him, the overflow of that—and we read about this in Galatians—is love, joy, peace, patience, kindness, self-control. These are all things that we want, that we pursue through money.

Money as a Spiritual Battle

And so I think it is a spiritual battle that is understated in our society, especially since we’re the richest country in the history of the world.

Last scripture I’ll throw at you. “It’s easier for the camel to go through the eye of the needle than for the richest nation in the history of the world to experience the kingdom of heaven.” Now, we know that that’s the illustration of a camel through the eye of a needle, but it’s–

Jim: Ffor those who don’t know. The walls of a kingdom would have short and small entries as a way of slowing down an attack. In order for a camel to get through there, it’d have to drop on its knees and kind of shimmy through it. So, it was really difficult. So, it’s not the literal eye of the needle that your mom used for your clothing and then camel.

Darryl: Yeah. Right.

Jim: Otherwise, we’re all dead.

Darryl: It’s like a Tom and Jerry episode or something.

Jim: Right.

The Kingdom of Heaven and Abiding in Him

Darryl: Yeah, but this is an interesting scripture because you could suggest that entering the kingdom of heaven is something that we could experience here. We hear about, “Thy kingdom come, thy will be done on earth as it is heaven,” the fullness of Christ, the overflow of love, the life that is truly life—that kingdom.

So, it’s easier for the camel to go through the eye of the needle than for the richest nation in the history of the world to experience the kingdom of heaven. And so, I think we have to ask ourselves: this thing that we call money, this currency, this store of value, is more spiritual than we think. And so, we’ve got to make sure that we’re abiding in Him. Otherwise, by default, our flesh will worship that money thing.

Wrestling With Corruption, Scripture, and Lifelong Formation

Jim: Yeah. Because there’s no simple answers. I don’t have any problems calling out things that I think are absolutely corrupt, which is part of the problem that I probably struggle with, because I don’t want my name, my ministry, or my business to ever be associated with the likes of corruption.

So, you take Kenneth Copeland. I don’t have any problem mentioning his name on this podcast and saying, “How does this guy live with himself?” I don’t know. And there’s a stack of them. There’s a stack of them.

But what’s really hard about that is you talk to supporters of those kinds of people involved in that corruption. Because there’s no hard math that says once you make this or once you have this, it becomes evil. The heart of the matter is, to what you’re saying, it’s a spiritual thing that takes a lot of wrestling.

And I’m going to lean into what you’re saying. The reason why I encourage the Lead Today Community to stay in the Scriptures, regardless of whether you even are understanding them or not, is that it’s a journey. It takes a while to even learn how to hear God.

Darryl: It’s crazy. It’s crazy hard. It’s crazy fun. I love it. Every day I read the Bible. There was a time that a friend of mine told me he loved the Bible. He opened it and it was amazing. I said, “I don’t get that.” And then I just kept doing it, and then all of a sudden it started to come alive. I don’t know. It’s just kind of a thing. At a certain point in life, I started to come alive.

Wisdom, Influence, and Closing Reflections

Jim: I’m a big Peter Drucker fan. Most people listening to this podcast have no idea who I’m talking about—

Darryl: He’s the OG.

Jim: Yeah. Right. He is and no one has replaced him as of yet, as far as I’m concerned. But about every two years, I pull out A Year with Drucker book and go through it. Every time I do, I’m reminded of how much his stuff lines up with the book of Proverbs.

And I’m going, “If I just keep reading the book of Proverbs like I’ve been, I will be Druckerized, and we’ll be good.”

Darryl: That’s so good.

Jim:  I know we’re drawing to an end here. Let me ask you a couple more quick questions.

Darryl: Sorry to be long-winded too. Some of these topics are obviously important to me.

Jim: One of my friends’ clients sent me a podcast last week that was two and a half hours. Obviously, I didn’t listen to it in one sitting.

Darryl: Or at 1.75. I listen to my podcast, my own podcast, at 1.3.

Jim: Yeah. Well, it’s painful, right?

Darryl: Right.

Jim: It’s painful. But anyway, I listened to it. So, what I was going to say is I think you have so much to share. I think we have kindred spirits here about this topic, and even broader, that you just need to be a perennial participant on this podcast.

Darryl: Oh, thank you. I’m honored to just come back. I appreciate it.

Restless Leaders: Peace, Coping, and Defining the “Right Things”

Driven Leaders and the Reality of Restlessness

Jim: So, all right. Most of the leaders I work with are driven, and they’re driven financially. Outwardly, they are super successful, but inwardly they are restless. What do they need to hear? If they’re listening to this, what do they need to hear?

Well, I’m just going to sit back and listen to you, because I fall into that category. There’s always something to do. Defining restless, I think, is important because there’s this spiritual, this soulical kind of thing—mind, will, and emotions. And then there’s the physical energy piece, where you always have to be doing something.

Yes, those two are the same, but they can be different. Some people are just high-energy people that are always doing things, and that can rest at a fast pace. There’s plenty of people that can rest at a fast pace that are spiritually engaged. They’re locked in with Jesus, but they just do things.

From the outside looking in, we might say they’re soulically not resting, but they’re like, “I’m just wired this way. I promise you guys, I’m abiding in Him. I’m sleeping. I’m checking boxes. I just like to do things.”

Jim: They just don’t do it the way somebody else does it.

Disturbance Beneath the Surface and Unhealthy Coping

Darryl: So, it’s hard for me from the outside looking in. But there’s a bunch of people that, even if they’re moving fast physically or they’re on the couch physically, inside they’re disturbed. They don’t have this peace that’s just disturbing them.

Jim: That’s different.

Darryl: That’s different. That’s real. And oftentimes, the fruit of that in entrepreneurs is pretty ugly fruit. Nine times out of ten, it is alcoholism.

Jim: That’s how they’re numbing it. That’s how they’re medicating. We all medicate. That’s a great podcast by itself. Probably getting two or three guys around this table who’ve got some experience working with people and just having a layman’s conversation about it would be pretty healthy for people to listen to.

Leadership, Trust, and Doing the Right Things

I’m going to share this as we get ready to close, since I mentioned Drucker. I totally forgot about this, but on the front end of that same book that I was referring to, he said, or at least the general editor who was synthesizing some of his words said that when you listen to speakers today, they all have different kinds of definitions of what a good leader looks like or what good leadership looks like.

And then, as Ducker sometimes does, because he doesn’t always do it, sometimes he is a guy who beats around the bush. He goes around the bush 40 times and then lands it. In his mind, he’s got to do that for you to get the whole context of what he’s about to say. Other times, it seems like he doesn’t care. He just lands the plane.

In this case, he lands the plane. He goes, “Look,” and I’m kind of picking off of what you said about, on the outside, it looks like we’re all doing things maybe differently, and is it necessarily right or wrong how someone’s doing it? But anyway, Ducker says this. He goes, “Leaders come in all kinds of shapes, sizes, styles, and what have you. And there is evidence that just about every one of them works within their context.”

Good leadership comes down to two things. One is they’re getting the right things done, and you can trust them.

Defining the Right Things in Practice

And that was just so crisp with all the leadership material that is being thrown at us today. I thought, wow, now that can be unpacked in a lot of ways, which is great, but going back to that base.

So, I think that’s what I would insert in our conversation. I would say, as a leader, are you confident that you’re about the right things? And if you’re about the right things, you probably notice that there is a trust culture that is beginning to surround you in that. I know that’s a bit abstract, but it’s at least a directional deal.

Darryl: It’s good, though. Yeah, it makes sense. And there’s been a lot of different theories on what leadership is. It’s been obviously studied, but narrowing that down, and even unpacking that on a completely separate podcast, and asking ourselves what is the right thing to do.

And sometimes I define what I’m supposed to do as the right thing as cast the vision, create a strategy, ensure the culture is maintained, and find kinks in the hose. That’s kind of how I break down, if I were to say what’s the subcategory of the right thing. That’s how I frame up my role in leadership of 21 employees. There’s a lot of moving parts, even in a small business.

Conclusion and Resources

Jim: How do people find out about your practice? How do they get a hold of one of your books?

Darryl: Yeah. So, I’ve got the Retire in Texas podcast. That’s one way. LinkedIn’s a good link. In the Retire in Texas podcast, I cover a lot of money topics, everything from behavioral finance to what’s the economic landscape. I’m not an economist, but I tend to have a pulse. I’ll talk about stuff that is concerning. If Bitcoin’s the flavor of the day, I’ll discuss Bitcoin. Connecting through that podcast platform is good.

And then LinkedIn, but you can also get any of those books on Amazon. In fact, all proceeds to those specific books go to four kids that live in my house.

Jim: That’s awesome. And that should be your first ministry, right?

Darryl: Exactly. Promise. You can’t cash jelly beans. There’s not a lot of money in books. But yeah, thank you for supporting.

Jim: No, there’s definitely not. Or at least I haven’t figured that part out yet. Anyway, well, Darryl, great to have you with us. Thanks for being here.

Darryl: It’s my pleasure. It’s fun.

Outro

Winston: Hey, thank you so much for joining us on the Today Counts Show. We’ve got so much more planned for you, so stay tuned and stay connected on Instagram, LinkedIn, Facebook, and subscribe on YouTube. And remember, today counts.
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