The AMAZING New Generation of Leaders -- WTW 068 with Joe Calloway

What a thrill! First of all, for those who don't know, Joe Callaway was the very first guest on our very first Walking the Walk episode. Seems like ancient history, huh, Joe? Yeah, and he's also our highest-rated guest, so you guys love him, and I love him too. Um, I met him a lot of years ago now, huh? And Joe became just a dear friend and a trusted mentor and someone who, you know, I can count on my hands, and I'm blessed with this, I can count on my hands the people who really, really made a significant change in my life, and Joe is one of them and continues to make an impact in my life. So it's always a treat to to be with Joe. And Joe, you've been up to all kinds of cool stuff. I want you to catch me up.

Well, I'll give you the short version.

Yeah, yeah, I know you'd be here all day.

About, wow, almost exactly, Jim, 4 years ago, it was 4 years ago this month because it was 2019, I hit full on doing keynote speaking.

Yeah, which is—

which I had done other things. I'd done some consulting and a lot of workshop stuff, but keynote speaking was my bread and butter. And I just finally thought, you know, I've, I've done enough of that.

Oh, you put on your miles.

Oh my gosh, I put in the miles, put in the time. So that opened up a vast amount of time for me. And so, uh, I did and still do some more workshoppy type, uh, sessions generally with senior leadership of medium-sized companies or sometimes even smaller companies. But I'm also involved— I've gotten more involved with two real estate partnerships that I'm in, and we generally build condo developments and then sell them. Um, I'm also still involved with a, uh, a ski board— I mean, snowboard ski manufacturing company, right? Gilson Snow, that I was one of the original investors. Uh, and since we've talked, I've gotten pretty involved with the wholesale Kentucky bourbon business.

That doesn't surprise me.

So, and that's not a dig.

So people say, you know, I mean, but Joe, Joe is an aficionado.

Well, it's right down my alley and down my mental capacity, uh, track because it's very complicated business, Jim. We buy thousands of barrels of brand new, just distilled Kentucky bourbon, and we let it sit for 2 years Then we sell it to somebody else.

I like it, I like it. Well, if you want to store a couple of barrels, let me know. I've got some room. You might not get them back, right?

Exactly.

Yeah, yeah, yeah. I want to touch on the snowboard thing for a second, and there's, there's a, you know, a nefarious reason for this. Um, a lot of talk right now about innovation stagnating, and especially in young leadership. And it's always bad to paint with a broad brush because there are so many tremendous people out there. But I think the trends are also useful for us to take a look at, if nothing else, for a warning sign. And you seem, the stories that I've heard about your snowboard thing, you really bucked the trends there. I mean, this was a really incredible thing. And it started because you were actually coaching a group of young entrepreneurs, right, that evolved into this? Am I getting the story right? Not quite. You're close.

Uh, my daughter was in the 5th grade. One of her teachers was a Teach for America, you know, volunteer teacher who was fabulous, one of the, one of the most conscientious, dedicated teachers, uh, I've ever known. He was very close friends with a guy named Nick Gilson, who, uh, was also a Teach for America volunteer. And Nick had his class, and they were, I don't know, 5th, 6th graders. Yeah, everybody start a business to teach them about, you know, the free enterprise system and all that. And one of the students said, well, Mr. Gilson, you should start a business. And Nick thought, you know, he's an engineering grad from one of the Ivy League schools, brilliant guy. But he thought, well, I've been playing with the idea of a new snowboard design. I mean, a patented change in the way the snowboard is designed. And so darn if he didn't start a snowboard company from his grade school.

Yeah.

Your class. Oh, man. And I tell you, it's been so much fun for me. I was one of the first investors. I've been an advisor to Nick ever since, and now we're going on 8, 9 years. And, uh, young guy, my experience— and I totally get the, the trends, you know, that we read about in the media— my personal experience with young leaders is that they knock me out. It's so encouraging to see the thinking and the, the, the willingness to work hard, the willingness to be patient, the willingness to personally do without as you build a business. I've worked a lot with new entrepreneurs through Belmont University here in Nashville. And they just impress me to the core, Jim. You know, I can call them kids. I'm old enough. I hear you.

They're good kids.

And they're solid.

Good kids, these 30, 40-year-olds. I know it. It's crazy. I feel, I'm feeling the age too. Yeah.

But this myth that they expect something for nothing is just that. It's a myth. Now, I'm sure some do.

Isn't it sad that, you know, sometimes the negative aspects of what's going on get more attention. And that's why I'm so glad. That's why I wanted you to talk about that because it is important, I think, for us to validate and encourage and highlight the folks that are really doing it. I mean, I'm going to agree with you because I think it's easy to grab onto that trend. I think it's attractive to the media to do so. But I'm with you. I mean, in our workshops, I'm seeing more and more young people that are really just grabbing the bull by the horns and going for it. And that's, that's really encouraging.

It is encouraging. And I told you before we started the show, I spoke this morning at my daughter's high school entrepreneur business class. And these were mostly seniors, a sprinkling of juniors, but they were just— you could see their wheels turning and they were taking notes. Yeah, they, they want to learn. They, they want to know how this business stuff works. They're so open to ideas. And I, I was— it was very conversational, and the feedback and the participation and the contributions I was getting for from them. I just thought, these guys are so cool. They're so smart.

Right. Let's dive into that a little bit more because I'm so fascinated to hear your take on this. What specifically are you, if you know, are there really, like, let's start with this. Are there any real substantive differences, the challenges that younger leaders are facing today and in today's market? If so, what are they? And What are the similarities? I mean, what are these guys sharing with you that you're finding so energizing? It is an extreme that they give us that energy, right? I mean, yeah.

The similarities, the things that you and I have experienced as always being true, that are still true, that, for example, these kids, these high school students this morning, we're talking about, they talked so much about service. And the need to understand your customer. Um, and so there, there are a lot of values of doing business, uh, that really hold true today. The difference— and this is something I was talking to him about— I said service has become— I think by service I mean the experience of the customer, right? The satisfaction of the customer. Um, it's more important than it's ever been because if I want to find out a company, okay, I might look at their, their ad and go, okay, that's what they say about themselves. I want to know what the market says about them. And if you want to know what the market says, you go on the internet, you go to social media, you go to Yelp, you go to Google, and you see what customers say.

That's easier than ever before, isn't it? Because I agree with you. I mean, if I say it, it's bragging. If someone else says it about me, it's an endorsement, right? And exactly, we used to have to go and dig those up and get them printed, you know. Yeah, now, you know, push of a button, click of a mouse, and you've got all, all the, uh, reviews you need, negative and positive.

You know, I think one of the big differences is that used to be you started a business, things just didn't change as quickly, right? You started a business and you could stick with it and stay on that path for a long time until it got traction. Today you start a business, you put it out there, minimum viable product, you roll it out there, and the market will tell you very quickly, we like this, we don't like that.

And so you find you have to change direction, be flexible, adaptable, comfortable with uncertainty. Yeah, yeah.

One thing I see in a lot of the young people today is they're okay with that. They're okay with saying, well, okay, that didn't work, but I got information from it. So let me, let me change direction somewhat. And that, that mindset serves them well. And they have to have that mindset because that's the reality that we truly do have to— we just have to change more often and more quickly than we ever did before.

That leads us to, I think, really an important distinction that I still continue to see is our level of comfortable with uncertainty. And I'm seeing, certainly research bears this out, that the younger generation in general is a lot less comfortable with uncertainty. Yet, you and I, I think we have the blessing to be preaching to the choir a lot. I mean, we're preaching to the folks, the young people that are really going out and getting it. But here's the thing. They still have to deal with their cohorts who may fall into that mindset, right, that are a little— are you seeing that at all? And if so, how are they helping their own generation become more comfortable? Because like I said, I mean, flexible, adaptable, comfortable uncertainty. That's the only way we're going to get ahead. That's the only way any— I think that's a timeless mindset.

Yeah, you know, that's a really interesting question. I think that what occurs to me, Jim, is that, and you know, you mentioned that we preach to the choir. I think the people that are good with uncertainty, and it's funny, I ask a question of my clients I have for years. I'll say, let me ask you a question, a very broad general question. What's gonna happen next?

Right.

And they all look at me like, and I say, come on now. What's the correct answer? And somebody will always say, I don't know.

And that's like, if they come up with an answer, I'm always a little suspicious.

The correct answer is I don't know. Yeah. But I think, I think people that are comfortable with that, they tend to find each other. And the ones that aren't comfortable with that tend to remove themselves and say this, you know, I want to go someplace where everything is set up and it's going to stay that way forever.

And of course, there's a place, there's a place for that, and there's nothing wrong with that, that employee mentality, right? But having said that, that's not really who we're dealing with most of the time. We're dealing with people who want, you know, who want to be out front. They want to be leading people to a better place. So yeah, that's—

yeah. And you know what, one thing that I think we can all agree on as a trend is it used to be the most common career scenario was to have 2 or 3 jobs throughout your whole career. And now you might have 30 jobs through your career. There's just, there's a lot, a lot of change.

Yeah. You know, I remember going to a seminar when I was in the martial arts business years ago, and a lot of the people in the room, it was their first business, right?. And the guy leading the seminar was pretty insightful. And he asked if we were nervous about staying in business, you know, and why. And he said, he asked this really interesting question. And I think this speaks to entrepreneurs. And it deals with, you know, how you become more comfortable with uncertainty. He said, how many people, if you work for somebody else, work for a big company, how many people have to make the decision to fire you? And everybody said, well, one, I suppose, right? He said, okay, how many members do you have in your martial arts academy? And, you know, people gave various numbers. But he said, you know how many people have to make the decision to fire for you?

All of them. Yeah.

You know what I mean? And I think that's, that was one of the first times I remember becoming more comfortable with that level of uncertainty as an entrepreneur, right? I think I thought that made a lot of sense. Now, not that we want to piss off everybody that we do business with, right? Then go that way.

I'll tell you, that's an interesting, I think that's a really healthy perspective to have. Yeah.

Where is the more certainty? Is the certainty where And again, I think we're touching on tradition, right? Traditionally, there was a lot of certainty in having a good job, right? And having that sense of security. But these days, I mean, what did Google just lay off? 12,000 people?

That's exactly what I was going to bring up.

Yeah. And you never know. I mean, right? Well, they said it was a surprise. Yeah. I'm not making fun of the people, but you understand. I mean, there had to be some signs coming for that.

Yeah, well, it's, it's, you know, it's funny, we've been talking about— gosh, Jim, I remember in 19— what, '88? Doing, doing a presentation.

I wasn't born yet, Joe. I wasn't born yet.

Positive about change. Yeah, and that was the big thing. Was changed. And I look back at the change that was happening then, and it's like the old cartoon of a snail on the back of a turtle, and the snail's going, "Wee!" That's a— but you compare that to now.

Yeah.

And I tell you that you used the word uncertainty. I think having a comfort level with uncertainty is kind of getting to be a requirement.

Amen.

Certainly if you're an entrepreneur, it is.

No, amen. And you know, it's funny because I can't tell you how many times, you know, in a Sensei Leader presentation where, you know, someone will talk about a new idea. I said, none of these ideas are new. I said, most of what I'm preaching is, you know, I'm stealing from sources that are 2,000 years old, you know. And, uh, borrowing— I think was the Greek philosopher Pliny the Elder. When did he live? Around 500 or so BC. And he said, the only certainty is uncertainty. You know, it sounds like a stupid t-shirt slogan until you really, really think about it. And to me, it seems— and, and if this helps anybody, I mean, in my experience— and it's not always comfortable, don't get me wrong, sometimes it's brutally painful, sometimes it's horribly frightening, right? But all the best things happened out of the uncertainty because I think that's where we find resources that we never knew we had. We find energy we never knew we had. We start to come up with ideas that we didn't have to come up with when things were static, right?

Jim, I remember a little more recent history in the '90s.

I wasn't born then either, yeah.

I had two main clients. That accounted for 80 to 85% of my business. Both of them, for very different reasons, didn't have anything to do with me. It— one had to do with the total reorganization of the company.

Yeah, yeah.

The other one had to do with a, a change in leadership and ownership that shifted the philosophy. Um, within 2 months 85% of my business is gone.

Yeah.

And it, um, it was, it was horrible. You talk about brutally painful. I mean, that's— it was like being on the floor in fetal position. What am I gonna do? And I was forced to get creative, and I was forced kicking and screaming to come up with things that made my business so much better.

Well, that changed your life, really.

It totally changed my life, and it ended up being a much, much, much better, much more lucrative business than I was in before. But I didn't have the vision or the wherewithal. You know, there's an approach that, that I think can be valuable. Which is, okay, do this exercise. What could a competitor or even the market do to put you out of business? And when you come up with those things or that thing, the next step is, okay, start doing that yourself.

Oh, amen.

Self out of business before something or somebody else does.

Yeah, you know, I couldn't agree with you more. And it flashes me back to the early days when COVID hit and, you know, people were calling and were just beside themselves trying to come up with some way out of it, not knowing from day to day, right, what the global circumstances were going to be. And I think that was one of the biggest ones in our lifetime. Nobody was sure, you know, what we were going to have to react to. So anyway, you know, long story short, as we evolved out of that, It made me think about this. And I hope this helps people process uncertainty a little more. We might not know the specific conditions or circumstances, right? You didn't know what was going on inside those companies. But we do know, we can predict with certainty that these things are going to happen to us in business. We're going to find times when we have a cash flow problem. We're going to find times when competitors are stepping up and putting out ideas that we haven't anticipated, right? We're going to expect that there's going to be some kind of global pressure. We don't know what it is, whether it's the supply chain or inflation or anything like that. We know these things are going to happen. They're cyclical. They happen all the time, right? I like what you said. Why not prepare for those things, right? Why not prepare for those things now? Um, better be prepared and not have it happen than to be shocked when it does. No.

Yeah, what was it? There, there was a Oh, two things. A guy that I worked for a million years ago before I really had my own business, he had one was a little sign, a wooden sign that he kept on the front of his desk. And it was a business in which the unexpected things happened to contracts a lot. And it would be the situation where somebody go into his office and say, Jim, the such-and-such deal is falling apart. It's Armageddon. The world is coming to an end. And he would always point to that sign and it said, there is another way of looking at this. That's all it said.

I like that.

Yeah. And so it would always force us to go, okay, what would that other way or those other ways be. And the other thing that was very helpful was it became a mantra of everybody that worked there because it really was a business that just had surprises on a continual basis. And the mantra was, whatever happens is normal.

Hmm.

Now, whatever happens may not be acceptable. It might be painful, unusual, completely unexpected, but it's normal. It's just like the list you were just going down of things that happen, right?

Doesn't the universe— I think the physicist— oh, good.

Well, I was just saying it was really helpful for us to talk as a group about this idea of, guys, whatever's thrown at us, That's normal.

Yeah, no, I was just thinking when you said that about, you know, the great physicists throughout history have proven pretty much without a doubt the universe exists in a state of chaos and entropy, right? Not in a case, not in a state of stasis. So, we best embrace that. Now, leaders that are facing— it's interesting because I think one of the challenges that that we're facing is the rate of change, right?

Yeah.

People are not accustomed to. But I like what you're saying, that all these things can be opportunities if we reframe, if we look at things from a different lens, look at things from— And one of the arguments that we sometimes get into is this, where people still cling to the idea that leaders are people that have the answers. And I'd love to hear your perspective on this, especially in context to what we're talking about now. I don't believe that for a minute. I believe the greatest leaders, the greatest leaders that I've run into, that I've worked with, and who inspire me are the ones that very seldom have solid answers. But they've disciplined themselves to know how to ask the right questions continually. And well, here it is. Am I way off base? I don't know.

No, I'm right in sync with that idea. And I'm one of those believers in terms of the situations where I've been the leader and then looking at effective leaders that— because that's one cool thing about our work. We get to see, we get to work with some really good people, you know, under the umbrella of we're teaching them, but we're learning so much at the same time. And, you know, one thing that stuck with me was something that Steve Jobs said, which was He said, we don't hire smart people to tell them what to do. Yeah, we hire smart people for them to tell us what to do.

Exactly, exactly. You have smart people top to bottom, right?

Oh, I've always leaned towards and had a bias towards turning people loose on problems. Yeah, and challenges, and seeing what they come up with. Now, I have no problem being the person that's, that's leading the group. But as the leader, I absolutely reject the idea that I am the source of the only good ideas.

Right, right. You're guiding them. You're not forcing them down a lane that you've prescribed for them, right?

Yeah, exactly. I think people will so often, I think people will more often than not will surprise you if you point them at a problem and say, there you go.

Now you put me in mind of one of my favorite quotes from General Patton, right? Don't tell people what to do, tell them what needs to be done and they'll surprise you with their ingenuity, right?

Exactly.

That's amazing. Are the younger leaders that you're working with, are they more comfortable with— because what we're touching on here a little bit, I think, is this idea of vulnerability. And for those who haven't run into this research yet, vulnerability actually is showing up consistently as one of the most important traits of an effective leader. And for a number of reasons, but one of the most important is because it engenders trust. And we don't mean, you know, going out and, you know, throwing a fit and saying, 'Oh my God, the world's falling apart,' you know, and this and that. They don't— people don't want that from their leaders. But they want some openness, right? They want some openness. They want to know you as a human being. And if I'm hearing you right, because I think we're in lockstep with this too, we usually are, aren't we? Where when we're facing a challenge as an organization, I think the most successful organizations and the most successful leaders are the ones who go out and frame the challenge and say, look, this is what we're facing. What do you guys think? Can we get together? Can we come up? Are you seeing the younger leaders being a little more open to that mindset?

I'm seeing them being much more open to that. And I recall a leader who, and this was a few years ago, and he wasn't necessarily a young leader, but boy, he was good, Jim. And their company went through Wow, they went through just a firestorm, um, a lot of things going on that weren't good. And he said to the whole company, his message was very clear. He said, right now at this moment, I don't know, we're gonna have to figure out how to get through this. I don't know how to get through it, but here's what I do know. And here's what all of you know. I know who we are.

Hmm.

That is what makes me confident that we will get through it.

Yeah.

I don't know how to handle the circumstances right now, but by gosh, I know who we are. And that's what gives me confidence that, that we'll be fine through this. We'll figure it out. You know, it's funny. Uh, We're all friends. You guys are friends with my wife Annette and I, and Annette and I have joked for years— well, no, we're not joking, it's true, but it makes us smile— that our family mantra ever since we met each other has been— we ought to have it on a coat of arms somewhere— and it's simply this: we'll figure it out.

Yeah, right.

You know, we'll figure it out.

Yeah, yeah. Oh, how dull life would be without challenges. Once in a while, could use a few fewer challenges.

Yeah, that's for sure. And they do seem to come in bunches sometimes.

Yeah, yeah, yeah. But you know, it's, it's all good. And I think, I think you'd reinforce this, uh, uh, you know, trust me when I say that even though it didn't feel that way in the moment, I think the toughest the toughest times, the times where the greatest challenges can be looked back on as some of the best.

And Jim, I want to go back just briefly to the word vulnerability because there's really something there. I remember a senior official, a senior executive with a major airline at a big event. He came on stage, he delivered just horrible news to everybody in the room about what they could expect in terms of resources this coming year. It was just all bad news. And he said, uh, he prefaced it by saying, you guys know me, I'm going to tell you what's going on and where we all stand, and we'll get through it. We'll get through it together. This is hard for me. This is really hard, but here's where we stand. And at the end of telling everybody in the room— there were about 500 people— what they did not want to hear, he got a standing ovation. And after it, I was talking with a couple of the people, and I said, I think the answer to this is obvious, but I want to hear you say it. I said, he gives you nothing but bad news, and you give him a standing ovation. What's up with that? And I'm quoting, the guy said, because there's no bullshit about that guy. And we all know it. He tells us the truth. We know where we stand. We know where he stands, even when it's really, really hard. And so that vulnerability and that honesty, it made him relatable. And it also gave him tremendous credibility with them.

I'm almost wondering if the semantic is the problem, you know, that too many people associate vulnerability with weakness where it might be better to, you know, again, I can't help but borrow from my background, but, you know, the masters I was blessed to study with, and some of them were the most humble people even though they're some of the greatest martial artists in the world, but they were humble. That idea of humility that I think is, I don't know, I don't draw any hard line between vulnerability and humility. I think that's That's what this man expressed. That's a beautiful story.

It's a great story. And, you know, I'm loving what you're saying because when you see humility and vulnerability from a master, wow.

Yeah.

I mean, that has such— I think it has such a quiet, powerful, positive impact on people.

Works better than arrogance.

Humility from a master. That's a beautiful concept.

Yeah, yeah. Well, Joe, geez, it's been such a pleasure having you on the show again. And we— and, you know, I know we said this is my fault. I let— I let Walking the Walk slide, and I shouldn't have. Um, I really appreciate everyone who kept the thing going. I mean, we've been shocked to look at the— at the stats and see how many people have been listening to past episodes because we've got remarkable guests. Um, you guys kept it all going and gave me energy to to get it back up and renew it again. And Joe, you know, we always say this, but just want to have you as a regular guest all the time. How about every show?

Hey, this is like coming home for me. This space feels really good, and you know it does.

You got any pearls you want to drop for the— give you the final word here? I know it's always awful to put people on the spot like that, isn't it?

You know what popped in my head?

What?

Warren Zevon. Oh yeah, he knew he was dying. Yeah, and he was on David Letterman's show, and he and Letterman were dear friends. And Letterman said, okay, the world knows what's going on with you right now, what's your advice? And Warren Zevon said, enjoy every sandwich.

That's a great one.

I don't know that I can top that.

No, thanks for sharing that.