EntreLeadership - Your Biggest Barrier to Success with Ryan Holiday

Episode Date: September 27, 2021

The last 18 months have been this generation of business owners’ greatest challenge. A natural byproduct of a challenging situation is fear. You’ve probably felt your fair share of it recently as you guided your team through the chaos. But as a leader it’s your job to lead no matter the circumstance, and that’s going to require courage. In this week’s episode of The EntreLeadership Podcast, we sit down with Ryan Holiday to discuss his new book, Courage Is Calling. Ryan challenges us to ponder the question, “What would the world look like if we all acted courageously every day?” Then, in our second segment, George Kamel sits down with Ramsey Solutions’ Executive Vice President Blake Thompson. He breaks down how we, at Ramsey, have been taking calculated risks since the early days when The Dave Ramsey Show still only had one station.   The EntreLeadership Podcast Ryan Holiday's Website Courage Is Calling by Ryan Holiday The Gift of Fear by Gavin de Becker Ramsey Solutions' Website Watch the Borrowed Future documentary trailer Borrowed Future podcast Download the Mission Statement Mapper Schedule a call with Tim, the Producer.   Learn more about the offers from our EntreLeadership Partners: BELAY  |  Gravy  |  Hite Digital | NetSuite Learn more about your ad choices. Visit megaphone.fm/adchoices

As a business owner, you're faced with new and bigger challenges every single day. And when you don't have all the answers, fear starts to set in. So the real question is, how do we deal with that fear? From the Ramsey Network, this is the Entree Leadership podcast, where we help business leaders grow themselves, their teams, and their profits. I'm your host, George Camel, and today's episode is all about having courage in the face of fear, which connects to our business driver of Personal. Our first guest is Ryan Holiday.

He's a best-selling author and one of the world's foremost writers on ancient philosophy and its place in everyday life. Ryan's newest book is Courage is Calling. Fortune favors the brave. I sat down with Ryan to talk about how small business owners can face their fears head on with heroic courage. In our second conversation, I talk with Ramsey leader Blake Thompson, and we talk about how to take calculated risks in your business. Up first, my conversation with Ryan about conquering your fears. Ryan, it's good to have you. How are you?

Yeah, thanks, man. Good to see you. I'm real curious because I know you're an avid reader. You read, I don't know, it feels like a gazillion books a year. You are raising small children with your wife. You are running a business. And you're also writing new books, releasing books. How do you do it? Are you fully human? I do think I'm fully human. I would say that instead of all those things sort of competing with my time to read, they're all related to each of. other, right? So I read to be a better father. I read to be a better writer. In fact, if I'm not reading, I can't write. So it all stems from the reading. I even, I also have a bookstore. So it's, it's work in that sense as well. I made this distinction pretty early on in my life and my career that reading wasn't a distraction from my work, that reading was a part of my work, or it was my work.

It is my job. So, you know, I think people will sit at their computer and read ESPN all day and and not feel that you know, they're not working, right? Like, it looks like you're doing your job. But if they were to lean back in their chair and kick up their feet and read a book, this would somehow be slacking off. And I just don't see it that way. I make time to read and I do it like it matters because it does. And on top of that, you decided I'm going to be a farmer too, right? Well, I'm not much of a farmer. I do live on some property outside Austin here in Texas, but I'm not growing anything. It's more of a hobby. Yeah, that's awesome. Well, I'm pumped to talk with you. Obviously, all of this reading has made you a great writer. And I'm really excited about

this book because I think it's coming at a perfect time where I think people need courage now more than ever. So I want to get into the book and you really, you break it up into a few sections. And the first section that we enter is fear. Is that really the first thing we have to combat when it comes to, you know, being a business owner and tackling the new thing every day? Yeah, you can't be brave without overcoming fear first. If it wasn't scary, if it was easy, if there was a guarantee, first off, everyone would do it and there wouldn't be any value in it. But it's precisely because it's scary that it creates the opportunities that we're looking for. So yeah, I sort of, I set up the book as fear being the sort of the first battle that gets in between us and not just what we want to do, but what we can do, what we're capable of doing, what we're called to do. And so that's that first obstacle that we have to get over. Yeah, you talk about in the book being scared for a moment versus being afraid all the time, living in fear. What is the difference between those? Yeah, there's a great Faulkner quote.

He says, it's okay to be scared. You can't help that, but don't be afraid. And this actually is a pretty ancient stoic principle as well. We have an immediate reaction to things. We have that sort of flicker of fear or we have that temptation or we have that doubt. You know, we have the initial emotional reaction, right? somebody jumps out from behind a corner, you're going to be scared. But if you decide not to proceed after that, that's what we would term being afraid. So all of these things that we're talking about,

starting their own business, having to have a tough negotiation, having to fire someone, these are things that should scare you because they're hard, right? And if you've never done them before, there's a certain amount of uncertainty in them as well. But that's not an excuse, not to do them, right? You still have to proceed. And that's why they call courage the sort of the triumph over fear. Again, if you weren't afraid, it wouldn't be particularly admirable that you did it. Yeah. And you talk about this internal voice that leads us into the person we want to become. We talk a lot about in this podcast about growing yourself as a leader and becoming that person. What is that internal voice doing in your head that says, hey, this is scary, don't do this.

Is it this kind of devil on the shoulder? I think it's a lot of different voices, actually. I tell the story of Florence Nightingale in the book. And, you know, she at a very young age, gets this call. An internal call, you could call it a spiritual call, but she gets called to something greater than just being sort of a spoiled, rich person in Victorian Britain. And she hears that call, but she thinks it can't possibly be meant for me.

I don't know what it is. I'm not good enough. She feels this sort of imposter syndrome. doubts, right, early on. But as she begins to explore it, she gets this idea that she was meant to be a nurse. And then she starts to hear a different voice telling her not to do it. And this is the voice of society. This is the voice of her parents. This is the voice of her sister. This is the voice of the men who want to marry her, right? All the different voices that are telling her, that's not appropriate. That's not a good idea. Her parents actually take this as like a betrayal.

Like, what are we not good enough for you? You think you're better than us, you know, all that kind of stuff. And eventually, like, something like 15 or 16 years after she first gets this call and she hasn't done anything about it. She hears the voice again. She thinks it's the voice of God, but it could be anything. She says, the voice says to her, are you going to let what other people think prevent you from answering my call? And this is what finally sort of pushes her over the edge and she does it. And her journey is not just fear of what other people think, but real sort of danger on the battlefield and from disease. But I think a lot of different things hold us back, our own doubts, the doubts of other people, the real dangers and risks of what we're doing.

And you just think about where the world would be if she had decided to refuse that call. I love that idea of answering the call. A lot of business owners, the last 18 months, has been some of the toughest decisions, some of the most fear, some of the most opinions from people than they've ever experienced. And we have a, a core value at Ramsey's Solutions is fear not. We don't make decisions out of fear. So what is the cost of allowing fear to rule your business strategy and decision making? Yeah, it's actually the most repeated phrase in the Bible is be not afraid, which I think is a sort of a lovely little example of what you're talking about. One thing to think about, and there's a great book by

Gavin DeBecker called The Gift of Fear. He's a personal protection expert. He works with lots of celebrities and stuff. But he says, you know, one question to ask yourself when you're being afraid is what is this worry costing me? What am I not thinking about by choosing to be anxious, worried, afraid, nervous, filled with self-doubt? And so I like to think about it as kind of a resource allocation issue. This is something I was thinking about as I was writing this book and another book I got this advice from someone. It's basically the idea of don't be afraid of the material because the material can sense this and it's not going to help. Right.

So if you think about being afraid as it's like, you know, on your computer, when it's going really slow and you find out it's running some program in the background that you didn't even want to be running in the first place, I kind of see fear as something like that. It's just eating up our bandwidth. And ironically, by eating up the bandwidth, it's actually making it less likely that we'll be able to successfully do whatever it is that we're struggling. to do. The thing is hard enough. You're stepping up to the plate to hit against a pitcher in major league baseball. Being afraid of the ball is going to make an already extraordinarily

difficult thing even harder. Yeah, and fear is kind of this part of life that we just have to manage. We're not going to just get rid of fear. We're always going to have some level of that, and we have to manage it well. And so how do you see great leaders managing fear and succeed in spite of it? What are some of the tactical things we need to do? One of the things I think you want to do is you want to take these really vague fears and concretize them. So oftentimes we're like, I remember when I was dropping out of college, I was terrified. This is the scariest thing I've ever done in my life. It's the most uncertain thing I've ever done in my life.

A lot of people, including my parents, were telling me it was a terrible idea. Part of what I sort of worked through was like, well, what's the worst that could happen, right? If it's this sort of vague fear, like, well, I could end up under a bridge somewhere. I could be a laughing stock, right? This could be the biggest regret of my life. And I remember a friend of mine, an older sort of mentor, he was like, you know, I took a year off of college. He was like, I got sick.

I spent a year in the hospital. And he's like, do you know how often it has come up in my life that college took five years as opposed to four years? Precisely zero times. He's like, the worst case scenario here is that you go back to school, this not having worked out, right? it doesn't matter at all. And so I think often the reason we're so afraid of things is that we've catastrophized when in fact the worst case scenario is actually quite manageable. And Marcus Reelis,

who I quote in the book says, you know, you're afraid of something. What will you do if it happens? And he says, you'll meet it with the same weapons that you've met all of your previous problems. Right. And so if you can go into what you're afraid of with some confidence, some sense of what you've been able to manage in the past, you realize that, you know, perhaps this has more to fear of you than you of it. It reminds me of this, you know, this epidemic of anxiety that so many people are experiencing, and it's this fear of something that hasn't even happened yet, and we're already playing out these worst case scenarios in our head to kind of protect ourselves. And I can see that with a lot of business owners out there who have had to make these hard decisions, and there's

new restrictions, and there's new regulations, and my employees are upset because I didn't do this I did too much of this. I think there's just so much to manage for those people out there. But fear isn't always a bad thing, right? There is some level of fear that is actually a healthy thing where your brain is saying, hey, use this to make better decisions, be wise. So how do we use fear as a productive force in our life and in business? Yeah, this is really, really important.

And as I said, you know, if you didn't feel fear, it would be a bad thing. And it's a good thing that you do feel fear. Aristotle talks about this. He says, actually, courage exists on a spectrum. Right? He says on the one end of the spectrum is cowardice, but on the other end of the spectrum is recklessness, the feeling of no fear. So courage is actually a midpoint between these two extremes. And that's really important. If you never had doubts, if you never felt fear, if you never questioned whether something was safe or good or likely to be successful, you'd drive off a lot of cliffs,

right? You'd crash into a lot of walls. You'd make a lot of unnecessary mistakes. It's not that every time somebody tells you that something is a bad idea, they're wrong, right? Sometimes they're right. So fear is really helpful, or at least some semblance of self-awareness, some understanding of risk and capability is really important. You know, a lot of businesses fail because they were too ambitious, right? They expanded too quickly. They took on too many projects. You know, they opened too soon. And someone who was a little more humble who took a little bit more time to evaluate all the different contingencies would have been more resilient and perhaps more sustainable in their pursuit. So it is important. Yeah, it reminds me

of this concept of kind of discernment and just having the wisdom that sometimes comes with age, right? Sometimes you just go, you know, the 60-year-old business owner looking at the 22-year-old business owner is going, man, he's just running and he's real ambitious, but he's about to make some real big mistakes because he doesn't have the right levels of fear, not making the right decisions. Well, look, and we all have different risk tolerances, not just individually, but based on where we are in our lives, right? So I can't afford to drop out when I'm 19 years old from college and be okay, totally failing. You know, my decision in my mid-20s to leave my corporate marketing life to become a writer, I'm a little bit older. I have a little bit more accomplished, but I'm also

with my now wife. So I have to consider the consequences of my decision on someone else. Now, as a father of two children, you know, with a brand and reputation, it's not that I don't take risks. It's that I have a different risk calculation. That's not to say I go around being afraid, but I have more to consider. This is true, not just in business, but COVID. If you're a 17-year-old or a 19-year-old and you're unattached and you live by yourself, you have a different risk calculation than if you live with your elderly parents who you take care of, right? It's a different calculation. What does that the process of discernment look like for you as you've kind of moved into a different

season of life? Because I think a lot of business owners, they're probably, you know, in the same space you are in the business sense where they're going, hey, I can't make the same risks and decisions when we were a 10-person team. We're now a 25-person team and there's more things to consider. Is there kind of a thought process or framework that they can use to make those decisions? Yeah, I mean, one, I think the idea of really thinking about the worst case scenario, really fleshing out, you know, what are the options? But the other thing, I think, it's not simply true that just because you're older or more successful or have more responsibility, that you should never take more risk. It also goes the other direction. You think about our politicians.

It's like, look, you have six years of job security here. You don't have to run, you know, for reelection for many years. And yet you're afraid of losing your job, right? What good is the job security if you're not going to use it? Or, you know, what good is having a company with 10 million or $100 million in revenue if you then act as if you can't afford to take risks, right? Jeff Bezos talks about this with Amazon. He says, look, I don't do bet the company bets, right? Meaning I'm not going to go all in on this or that. But that's not that he's risk averse. It's that he wants to take a lot more day-to-day smaller risks, right? So I I think as you get older and bigger, I think about this with my writing career. If my success as a writer and my platform doesn't allow me to take creative gambles here or there, what good is that success, right? It's actually not success.

It's actually decreased my autonomy. I'd be better off being an author with no audience if having the audience is going to prevent me from exploring what I'm interested in exploring. Yeah, Ramsey, we've adopted the model, I believe it's from Jim Collins, of the musket ball versus the cannonball. And we do a lot of musket ball things where we can kind of test to make sure we're going to the right direction before we use the cannonball, which is going to take a lot more resources and money and time and people to pull off. So I love that concept of taking the smaller risks, not feeling like you've got to put it all, put it all on black and hope for the best. That's right.

That's so good. So the second part of the book goes to the namesake. We're talking about courage here. and you'd say the way we deal with fear is obviously with courage. So what is your definition of courage? We've often said there's two kinds of courage. There's the moral courage and there's physical courage. I actually think at the end of the day they're the same thing. It's when you risk yourself, whether it's your reputation or your physical person, whether it's your finances or something else. you're always, courage is about putting yourself out there saying, you know, I volunteer. It's saying, I'll try. It's saying what you think. You know, it's believing that this idea that

you have could work. It's when you bet on yourself. When I think about courage, you know, you kind of go, well, that person's a courageous person. But we know no one is just born courageous. And their environment shapes them, the people in their lives, the voices, their experiences will shape that. but what are the steps that someone can take to build that muscle into their character? Well, and I would also say that courage isn't something that you earn, like, as a title that you get forever, right? There's plenty of people who have been physically courageous but moral cowards. And conversely, there's been people who are frail and weak who you would never have thought as being as brave or as strong as a special forces operator, but push come to shove under incredible pressure, you know, managed to.

to stand up for what they believe in or stand up for a cause that's right. So courage, I think you want to see as something you do on an ongoing basis. And what my premise of the book, and I sort of talk about this a little bit in the conclusion, I think it's preposterous to describe yourself as courageous or cowardly, right? I think it's more something that you try to do on a daily basis. More often than not, do you let fear guide you or do you do the braver, stronger thing? So as we think, think about how we apply this in our life. I mean, one question I like to ask is, well, what would the world look like if everyone acted this way, right? If everyone decided, well, I can't risk my stuff for this, right? And I think we see this in Washington. We see this in business. We see this in life.

You know, nobody wants to be the one that takes the hit. They're waiting for the right moment. But of course, there never is a right moment. This is an excuse to not have to, make yourself vulnerable. Yeah, and it makes me think of the fact that everyone's kind of looking to you and you're feeling the weight of that decision going, how are people going to feel about me and this decision? Are they going to like me? Are they going to hate me? What's the feedback going to be like? And it brings me to this question because in this book, in the section, you say, the world is asking about your courage every single day. What do you mean by that?

Yeah, it's the idea that it's not a one-time thing. It's not just, oh, I served in World War II, and I was courageous then. But then, you know, you know, it's the idea. You know, it's not a one-time thing. But then, you came home and you looked around and there was segregation. Did you say anything or did you, you know, simply focus on the fact that this wasn't, you know, something that affected you, right? So when we think about courage, we think about it as a constant question that the world is asking you, are you going to do the right thing or are you going to do the easier and more expedient thing? And I think, again, it's about pushing yourself, especially as you get older, especially as you have more leverage and confidence in yourself, can you do this more often than

not? And when you're saying doing the right thing versus doing the easy expedient thing, is that coming from a place of values? You know, when you're trying to make the right call versus trying to make a decision to make this thing just go away, so you don't have to deal with it anymore, what does that look like to make a decision from your values? Well, I think values are an essential part of courage because there's a great quote from the poet Lord Byron, he says, you know, the cause makes all that hallows or degrades courage in its fall, meaning that to be courageous for the wrong thing is not something we admire, nor is it particularly meaningful. So when we think about courage, it has to be paired with values, or else it's just jumping out of an airplane for the hell of it, right? I was talking to a special

forces operator, and he was talking to me, he's like, we always have this example. of throwing yourself on a grenade, right? He says, if you can avoid throwing yourself on the grenade and no one will get hurt, well, then to throw yourself on the grenade is stupid, right? It's suicidal, right? And this goes to the idea of recklessness versus cowardice on a spectrum. It matters who you're doing it for and it matters what you're doing it for, right? You know, I contrast sort of two examples of courage in the book. For instance, read Hasting deciding to burn the boats behind him, get rid of the DVD business for Netflix to become a streaming company. That's an immensely courageous thing to do, right? That's extremely difficult. I contrast this with the decision of the

CEO of CVS several years ago to stop selling cigarettes, right? There's something that costs the company several billion dollars a year in revenue. Do they both require courage? Yes, because there's uncertainty. You're potentially risking something to potentially gain something. But in the case of CVS, this is of real societal value beyond just being a positive move for the business, right? And in fact, they see that cigarette sales nationally decrease. So CVS takes the hit, but society captures the benefit of this. Yeah, I think all of us want that level of courage. I mean, all the people we look up to in history have some level of courage. They stood up for something they cared about. They stood in the face of fear and opposition and they powered through and made a change in the world potentially because of those

decisions. So I think we all want that. And it all points to your last section here of heroic. So I want to talk about this because this kind of idea of heroicism, it points to something bigger than ourselves. And when we make decisions that benefit just us, that doesn't feel very courageous or heroic. It feels easy. So for the small business owners listening, they're doing this every day. I feel like they are the heroes because they are in service of something bigger than themselves. They're serving communities, their marketplace, their employees. What would you say to the business owners out there who are doing that heroic work every day? Well, you look at someone like the CEO of Texas Roadhouse during the pandemic, right? He takes his salary down to zero and he distributes that money to the employees. And so you think about all the decisions that you face as a leader or as an owner of a business where your, interests and the interests of your employees and certainly the interests of society are not always

aligned as we'd like them to be, right? A business could be very successful, but pollute the environment. A business could, I remember when I was at American Apparel, the CEO would say to me sometimes, he's like, look, if I was only in this to make money, I would have been a drug dealer. He's like, that's the best business in the world. Obviously, I have ethical concerns that guide me, that act as a sort of a set of boundaries for what I'm willing to do and what I'm not willing to do. And so you've got to think about why you're in this business, why you do what you do, and what your purpose on this planet is, right? You can't take the money with you when you die,

but you can think about the legacy you've created for your family, for the people who depend on your business, and for your business's impact on the world. So I think oftentimes, and look, we have competing constraints. We have shareholders. We have investors. We have fiduciary duties. At the same time, you know, I think about this with my business, Daily Stoke.

We make a lot of cool little products. And I have to ask myself, you know, is it worth 20% better margins to have this made in a Uyghur sweatshop in China? Or would I rather work with a family-owned business here in America and feel like I'm making a positive difference, right? And so you've got to make all sorts of decisions. But where courage comes in is that you, this is rarely the easier thing to do. This requires risking more capital, right? This requires perhaps working with someone more inexperienced. This requires going against the grain of your industry, to not outsource, to have a charity component in your thing, to pay a living wage to your workers.

the easier thing is almost always to do the more sort of ruthlessly capitalistic thing, but this comes at a cost not just to society, but also to your soul. And you've got to ask, where do your values come into play? Yeah, we talk a lot about on this podcast about having that the mission, the vision, the core values dialed in so that you have that foundation to make those decisions from, especially when you're a small business owner, you're competing against the big dogs and you're the underdog. And again, you're not going to be a ruthless capitalist and

go, well, you know, I'm going to compete with them by doing unethical things. These are, you know, mom and pop businesses. These are people who are salt of the earth, people fighting that fight every day. And you talk about in the section this idea of wilderness. And I just felt like, man, business owners, last 18 months, have been in the wilderness. So what do small business owners need to remember while they're in the wilderness or as they start crawling back out? So that chapter comes from one of my favorite quotes from Winston Churchill, who knew this intimately. But he talks about how we all come from society from the world.

But to be great at what we do, he says, you have to go into the wilderness. He says every prophet spends time in the wilderness. He doesn't mean in the woods. He means isolated or separated from everyone else and from conventional society. And he says, this is difficult, but this is where psychic dynamite is made. And I think if you can think about these last 18 months, as you being forced back upon yourself, you being forced to ask yourself,

what is important? What do I want my business to look like? What is my obligation to society? What's my obligation to other people? I was telling you about my bookstore earlier. I had to think about this. Look, in Texas, it's a good thing and a bad thing that you can basically do whatever you want, right?

Because now you have to decide what you're comfortable doing. You have to make these decisions. as opposed to them making them for you. So I have to decide, you know, are we going to require employees to wear masks? Are we going to be open during this surge or that surge? You know, are we going to stay open, right, when it would have been easier to close, right? You have to make these difficult decisions, but the upside is you should emerge from it with some sense of what you're capable of, right? We've all, if your business is still standing, your business has endured a historic,

historically significant event. If you are still standing as a person, you have survived something as great as the Depression or the Second World War or the 1918 pandemic. Like, you should emerge from this with some sense of what you're capable of. And so you needed courage to survive it. Having survived it should give you some courage going forward

because you know that you're stronger than you were when you went into it. That's encouraging. Well, as we wrap, I want to talk about stoicism. I know you're real passionate about stoic virtues, very obvious. I'm a part of your daily stoic email newsletter, which I love. So I want to end with this. What advice do you think the stoics would give to the modern small business owner today?

So in the middle of the Antonine plague, which is named after Marcus Aurelius, Marcus Aurelius, the great Stoic philosopher, lived during a plague, not like the one that we've just endured. and I really spent some time with meditations during the pandemic, and it helped me understand it on a new level. So he says, two quotes I'd leave you with. One, he says, there's two kinds of plagues, the one that destroys your body and the one that destroys your character, right? And so thinking about that there's two things to be worried about. And I think you and I both know a number of people that whether they've got COVID or not, they've definitely been infected with something. And it's changed them and it's made them worse in a lot of ways, left or right. They've been consumed by something. So that quote really hit me. But the big one that I think I'd leave a small business owner with, Marcus writes, it's unfortunate that this happened.

And then he catches himself and he goes, no, it's fortunate that it happened to me and that I've been able to survive it and not be changed by it. And I think that's what we want to think about. So yes, would you have chosen an 18-month pandemic that's killed hundreds of thousands of people and shut down businesses and caused all. the consequences that it's caused, no. But it did happen. And better it happened to you than to someone who didn't have the resources that you have, who wasn't as strong and entrepreneurial and resilient and creative and decent and brave as you. And that's why you were able to get through this. And that's

why you are a good leader. So if you think about it, not as something that you're unlucky that it happen to you, but that it's lucky that it happened to you because you have the skills to turn this into something. That's the place that courage gets us to. Wow, that's powerful. I'm not even a small business owner, and I'm encouraged to go fight another day. So, Ryan, thank you so much for your time, for your wisdom. The amount of time you spend just thinking about this stuff and distilling it down so that we can all benefit from it and the listeners can benefit from it. I'm so excited about your new book, Courage is calling, and how it's going to help so many people, and especially leaders and business owners out there. So thanks so much for taking the time.

I'm honored, man. I appreciate that. Thank you. Huge thanks to Ryan for an awesome conversation on courage and fear. If you want to get his newest book, Courage is calling Fortune Favors the Brave. Just click the link in the show notes. So now that we know how to face our fears with courage, it's time to learn how to take calculated risks in your business. I'll have a conversation about that right after this. Our second conversation is with Blake Thompson. He's the executive Vice President of Ramsey Network, and he shares how to take calculated risks towards your vision. Well, Blake, it's good to have you on the Entra Leadership Podcast. How are you doing?

I'm doing good. Thanks for having. So you are the Executive Vice President of Ramsey Network, which means you are responsible for the show that listeners are listening to right now. That is correct. That's big time. Yeah. We have a lot of these shows. This one's really important. Yeah, you started back in the day, this is what, I mean, 25, 30 years ago now, back when the Ramsey show, was a fledgling radio show, right? And now it's this behemoth that it is today. Yeah. Give us an overview of the journey from this little radio show out of Tennessee to now making a feature-length documentary that you're involved in.

Yeah, so the radio show actually started 30 years ago. We'll be celebrating that next year, just FYI. I've been here for 25 years. So when I started, we were just on in the local market of Nashville, Tennessee, it was called The Money Game. And Dave even had a co-host. And it was just a small show here that was starting to gain momentum and do very well. And so when I started with him, it wasn't because of me, but around that time, it just started catching fire. And we beat Rush Limbaugh in this market, which was a huge deal. And people started noticing it.

And so we just said, hey, this message isn't just for Nashville. We really feel like it's a national message. And so we decided to syndicate. And that's why he hired me originally was to have his own producer and to help syndicate the radio show. And in syndication, of course, that means grow the show in other markets. And so we just started. I know we're going to talk about risks today and how we do it, but it was a risk. It was like, do you take this huge monster risk and pay a lot of money for people to just put your show on their stations around the nation? And that's not what we did. We did a little tiny baby

steps into, let's get our first, our second radio station, Nashville, then Oak Ridge, Tennessee. we got Russellville, Kentucky, and grew it that way with little small risks of going, we think this is going to resonate, but before we just go blast money into this, let's make sure it's not just a Nashville problem. Yeah, and now we're over 600 stations, well over that on the radio show, and as times have changed, we've gone digital, and so we've got podcasts, and we've got YouTube, and we've really started to get into the video space as well. So here we are, you know, you're 25 years into this vision and this mission, and you're

you've been constantly taking risks because you know that what got us here won't get us there. Yeah. So talk to us about the evolution from radio show into documentary land. Yeah, it's like with anything, not just in what we do, but any of the business owners listening. It's, you can't just rest in what has got you to where you are today. We've reached a level success, of course, because we've done radio for 30 years. We've done podcasts for 15 years since the inception. We've done YouTube since it started. So we have done a good job of working at making those better, being number one.

We're in the top 1% on all those things that just named. But we can't just sit in that and rest in that and get fat and not keep moving ahead. So we're constantly having to say, where's the consumer? Where's the industry going? And of course, streaming is huge right now. And so that's something that we need to be on. We're not on Netflix today. We need to be on Netflix, Hulu, whatever.

We might need to have our own streaming app. So those are the things we're looking at and seeing consumers over there in this huge field. Though we have 18, 20 million listeners on all our other stuff, podcasts, YouTube, and radio, there are so many more people we're not touching and hitting in this day and age on places we're not. So you talk about the documentary. That was a great example of, hey, people are watching documentaries. People are watching film. People are streaming this stuff in their living rooms at home.

We're not there and we need to be there. So that's the only way you're going to grow, even as a business, is not just resting in what you've accomplished today, but always looking forward in the future and where the customer and the consumer's going. Yeah, it's interesting. There's this kind of balance that I feel where we're listening to the customers, we're seeing what's happening out there in the marketplace. We're also trying to balance that with our mission and our vision and making sure that we're aligning those two things. Is that where a lot of these decisions come from when you guys decide to do something new? Yeah, it is. It's all about what level of... strategy or risk you're going to take. We can't just, you look back in the history of this company and I can show you times where

we just shot like this big huge. We call it musket balls or cannon balls. You guys have talked about on the podcast, I'm sure, when we talk about risk. And that is, how can we learn from the customer by surveying, testing, shooting musket balls versus a million dollar cannonball? Like, let's go do this documentary because we feel it's a good idea or we think it is. You can look back in history on times we did the latter. and it failed. But if we did it right and gradually took the strategic risk instead of this carefree

or we think or feel or wet finger in the air kind of risk, that's what's led to success in the past. And that's how we teach our team going forward and how to launch anything brand new. So for the business owners out there, they're going, okay, Blake, so you're saying I don't need to go spend a million dollars on this huge risk. I can take some small steps today and start to test some things out and see what resonates and see what works before I make a huge financial. decision. Definitely. I just highly encourage those listening. One thing that we've learned in the last 25 years is just find out from your customers, your consumer, what's the felt need, where's the market going, et cetera, versus basing it on a feeling or a gut thing only, and then just pouring a lot of money on this huge risk and just hoping it works versus, again, these musket ball kind of

shooting these little musket balls and gradually building upon them in learning. And then, going, okay, we've proven this is where the market's headed. We've proven this is what the consumer wants. This is their felt need. So now we can invest this money or whatever this into this thing that's going to hit those needs. So let's talk about this documentary, Borrow the Future, how the student loans are killing the American dream. This is really our first foray into film and documentary, and it's very exciting. Our team saw a screener. Obviously, the documentary is coming out October 14th. They can't wait for everyone to stream it and check this thing out. But we did some musket balls here with this before we said hey we're going to spend you know a million dollars

into a documentary there there was some steps we took to get there talk to us that's a great example um instead of just going hey we know we should be over here because we're not in the documentary world or the film world um let's just invest a million dollars and go create this documentary and choose the topic just based on what we feel it would work that would be an error um so what we did is we said okay how can we test that this stuff resonates? So we decided to do the borrowed future podcast a few years ago, and George was a huge part of that. I highly recommend you go listen to that series.

And that was a risk for us, but a lower risk. And when I say it was a risk, we had never done that type of storytelling podcasts. We're great at having a personality and a host and a call-in type show and everything we do, and we've proven that for years, but we've never done a storytelling kind of thing around a topic like a student loan industry.

So that was a risk, but it was more of a musketball risk where we said, let's try to just do a podcast with the resources we have, the team we have, we didn't have to go hire a host, we had George, we didn't have to go hire this whole team to do it. Let's try it with our own team just to prove the thing first. And that was eight episodes, I believe, eight or nine that you guys did. And the success around that was amazing, and it resonated. And everyone knows student loans is a problem right now. but when you really talk to the people in the industry and the people who have been burned by them

and are living in that crisis right now like you guys did with that Barl Future podcast, we learned this is a big deal, this is huge, and we were smart enough to go, hey, while we're doing this audio, let's take some cameras and film too in case this grows into something else. Very small risk, still a risk, but what it did is it proved the fact that, hey, this could be also a film now because of the success of the document, the podcast, and that's what made us step into, okay, now let's invest some dollars and try our first step into the documentary. Yeah, that's awesome. And you're right. I mean, after what, a million and a

half downloads with the Bard Future podcast, we're going, okay, clearly people care about this topic and they want to hear from us on this issue. That's right. And we know that visual components are so huge. Everyone's watching devices these days. Let's do something visual that people can really grab on to and watch in 90 minutes. Yeah, so it was a good mix of knowing that, there's an area that we're not in and should be, but instead, like you said, investing all resources, hiring a whole team, spending a million plus, and just going, we figured out ways to baby step into that and prove it first and end up exactly where we wanted to be, proven that it's a needed thing. Yeah, and this is all tied to our vision, which is important to remind people that we're not taking

risks that are outside of our mission or our vision. And it really helps. When you're taking a leap towards the vision, you're going to get closer to the vision and to the mission. So that's a great reminder for the listeners. And this documentary, it probably took a lot more time and a lot more money than you guys expected. So talk to the listeners about what it looks like when you kind of jump a little further than you wanted to into the risk. Again, I feel like we did it the best we could by not jumping fully on the other end of we're going all team, all money, all resource. But at the same time, even the way I explained we did it with the podcast and proving it, it was still a major risk because we had never done that before. So I think your point is dead on.

Our mission is to help people and give them hope and to meet them where they're at with the resources, et cetera. And this student loan thing was so proven that it's such a crisis on the news, everywhere you look. But after talking to them and meeting with them and all that, it factored into that risk. It was like it's still on mission. We've proven it up to this point. It's a place we need to be. So let's invest some dollars. And at the end of the day, just because we did this documentary and it's going to be streamed on October 14th, that doesn't mean we've hit the pinnacle. That's still a test too. It's our first one. So we're going to have to see on the back end, was this worth it? The time, resources, two years to make, the money we put into this. And we're hoping,

it is and we feel we did the right strategy to get there. But a risk is a risk, no matter what level you look at it. But you've got to be willing to take those in order to grow and go down that path. We're taking this risk in hopes to helping millions of kids not make a terrible decision to go into college with debt and come out 20 years still having that debt. That's a risk we're taking because we feel so strongly about helping fix that problem. But at the same time, we're hoping this documentary resonates and works so we can do another documentary. The worst thing to do is this thing is flat and we took this risk and it doesn't work out. We're probably not going to go spend a ton of money in the documentary world.

When we look and try something else, sure, we're going to risk streaming coming up shortly. We're going to risk television programming, et cetera, things we're not at. Yeah, that's a good reminder too of the fact that we're actually looking at the numbers and we're looking at what happened, doing post-mortems. We do meetings like that all the time where we do four helpfuls and go, hey, what were What didn't work? What could we do better? What was missing, wrong, confused, all those different things to help us make better decisions going forward. We don't just do things and go, okay, who knows if that worked, but let's just keep going. That's right. It's vital. That's vital. The back end of that time to do that. So let's talk about other risks that you've seen the Ramsey leadership team take in your 25 years here because I think it's so crucial to not lead with fear. I mean, one of our core values is fear not. We don't make decisions based out of fear. So how do you take that risk and not let fear get in the way and start to make those changes towards your vision? Yeah, I mean, Ramsey's Solutions, the 25 years I've been here, is built on a lot of risks. And like I mentioned earlier, and Dave would even say this, and he said it before from a stage,

we can look back and see where those risks were calculated and done right with the musketball mentality, like I talked about, and the times where we shot a cannonball and spent a ton of money and made hires, and it was a failure. And what led to this new mentality of this leveling of risk and strategy of musketball versus cannonball came from those failures. So to your point, learning from our past mistakes or just kind of analyzing after the fact of what you did, what worked, what didn't. And so we're built on that.

Top of mind, things that come to my head, radio syndication. I mean, like we talked about earlier, we were just on locally, we were doing well. We could have just rested in that and gone, this is the pinnacle. We're helping a lot of people in Nashville. were the top talk radio show in Nashville and stopped right there. But we were so driven with our mission and what our goals were and our vision that it was bigger than that. So we took the risk of, okay, we're going to have to go try to self-sindicate this. No one does that.

They usually get bought and then been told what to do and talk about on air and then they get on everything. Well, Dave's not going to do that. We're going to have full control on how we talk to the market and our people. And so we took the risk of self-sindicated. and people told us all over the place and convinced us you can't that's not possible it's a huge risk you're going to spend that much time and effort to try to do this yourself and it worked and that's a great example of something we've done in house another is ramsie education when we were doing the radio show and syndicating it we were talking to adults mostly every day and what we started learning was that their children needed this and they were telling us they needed this they're not being taught this in high school or junior high So we saw that felt need, and that was a risk because people were like, there's no way you're going to be able to take the message you're teaching financially because there's scripture around it. It's based on, you know, godly principles and all that in the public school system. So we felt so strongly that it was a felt need and needed to happen that that was a huge risk for us to do that.

And we're told we couldn't do it. And today we're in one out of every three high schools in America in public schools doing what they're. told us we couldn't. If we wouldn't have taken that risk, we wouldn't be helping all those kids. And then other things like Ramsey Press, the publishing we do in house. We try to do books using other people and we found out they suck at it and they don't focus on us like we would focus on us in the marketing plans and all that. So we took a monster risk of saying we're not going to go with major publishers and we're going to do it ourselves in house. But it was small strategy, a little bit of time, small risk to figure out that world and how to

do it versus put all the guns, all the money on this. And, you know, just looking back in history, this place is built on really strategic risks. Yeah. And I think about all the different business units that are here. And it's kind of like Dave's investing advice where he says you've got to diversify, right? We want to be in four types of mutual funds. We don't want to be in single stocks. It's too risky. And we've done that well as a company where, hey, if one area, it doesn't do well because we fired a musketball and it failed, well, the company's not going down because of one piece over here. So that's a good reminder. On top of the of the fact that Dave Ramsey is, you know, the cash is king guy.

And so we do things with a cash position so that nothing is that big of a risk. You're not going into debt over things. Yeah, and along with that great point is the fact that when we do shoot a muskabal over here, that doesn't mean we're going to hire a ton of people. And when it doesn't work, we have to lay them off or figure out where they're going. Everyone listening can do certain things and test with what they have today to prove the need and the value and then make the decision of the bigger risk and the cost of, the hiring, et cetera, versus a lot of people do it the wrong way and go, I got this great idea,

let's invest all this money and hire all this to do it, and then it flops. Yeah. When you take an uncalculated risk that involves going into debt, that's probably the most dangerous situation to be. That's right. That's huge. So as we wrap here, I want to talk about the small business owners and what they should be investing in what are those calculated risk, what is the kind of courageous steps they need to take towards their vision so that they can, you know, fight again tomorrow and help the customers. Yeah, again, I've said it probably five times already, but we've been very successful with it here and learned it the hard way of doing it wrong so much. And that is invest in learning about

your customer. I mean, that's the bottom line. Start there, surveying, testing, et cetera, felt need, what is it? And you'll find when you do that properly and learn, you're learn those things, making that investment to fill those felt needs or to do whatever you need in your business to reach that customer at that level and where your industry is even going, those risks and decisions will be a lot easier to make because you have proven facts. So to answer your question, I just highly encourage those listening to invest in figuring out what your consumer and your customer wants, the whole musketball thing versus cannonball, and then invest in your team itself.

We do that well around here, and Dave's been doing it since day one. It's investing in the culture, in your team. You might not see it instantly, but what it will equal down the road and we've seen here is loyalty, ownership mentality, the stuff you want as a small business owner

from your team. That's so good. So it really starts with investing in your own company, in your own culture and team, and then you can go, hey, is there a new software we need to get? Or there's some new hires we need to make?

do we need to expand into a different location? And it starts with really listening to the customer and then making those decisions out of your values, your mission and your vision. One great thing Dave always says that goes along with this whole conversation, especially for business owners, is he always challenges us to break it before it breaks.

Like really be out in front of it. Is it something you should blow up or change the way you're doing it or go for this risk before you're on the other end going, man, I should have done it because it's going to break on. its own because I'm not strategically taking the risk in figuring out where we should be going. Well, Blake, I love this conversation. I love your heart around this stuff. You're so passionate

about our mission and our vision. And I am extra pumped about this documentary that you and our team are going to be putting out on October 14th. So, thanks. Pump for you. Thanks for you and your team to release that documentary Borrowed Future coming October 14th. If you want more information or you want to watch the trailer, you can go to borrowed future.com. As Blake talked about in episode, you need to know your vision, which is born out of the mission for your business. A mission statement is the driving force of a company. It says exactly who the company is, who they're not, and why they're in business. So whether you haven't developed a mission statement for your business yet, or you just need to refine it, we've got a worksheet

called the Mission Statement Mapper to help walk you through that process. If you want to download the mission statement mapper, just click the link in the show notes. Hope you enjoyed today's episode of the show. If you did, leave us a review and subscribe. so you don't miss the next one. And if you're a small business owner with 2 to 200 team members, we want to hear what you think of the show, what you like, what you don't like,

and what we could do better. You can give us your feedback by clicking the link in the show notes to schedule a call with Tim, our producer. If you want to keep up with us on social media, you can follow us at Entree Leadership. This episode was produced by Tim Hull, edited by Jacob Harrison and Bob Orquez,

and mixed and mastered by Will Rudder. I'm your host, George Camel, and on behalf of the entire Entree Leadership team, Thanks for listening. Until next time, keep learning and keep leading. If you enjoy this podcast, you should check out other great podcasts from the Ramsey Network, like The Ramsey Show. We want you to take control of your life and money once and for all. I'm Dave Ramsey, and along with my co-hosts on The Ramsey Show, we'll give you straight talk on everything from budgets to career to relationships.

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