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Sept. 9, 2026

REGENERATING Leadership and Wisdom Across Generations with Captain David Gallimore

REGENERATING Leadership and Wisdom Across Generations with Captain David Gallimore
The Adventures of Pipeman
REGENERATING Leadership and Wisdom Across Generations with Captain David Gallimore

The conversation focused on the concept of regeneration in both personal and societal contexts, exploring what it means to continually evolve, adapt, and mentor others through authenticity and vulnerability. The discussion explored generational divides, the responsibilities of elders, and the ongoing process of personal growth. Several points were raised, including the role of communication in bridging generational gaps, the influence of religion, and what it means to lead by example in an ever-changing world.

Main Topics Covered

  • The inspiration and goals behind starting the REGENERATE Show
  • Navigating life transitions and embracing vulnerability
  • The evolving nature of generational relationships and the definition of "elder"
  • The necessity of psychological safety and authentic connections
  • The importance of continuous personal development and modeling a growth mindset
  • Reflections on religion, belief, and the human tendency to seek control or certainty
Key Discussions & Stories
Genesis and Purpose of the REGENERATE Show
  • One concept discussed was the motivation and initial vision for starting the REGENERATE Show, including the desire to pay forward knowledge and help next generation leaders who may not have access to traditional executive coaching 04:14.
  • The conversation traced the show's evolution, emphasizing a commitment to co-creating spontaneous, authentic moments rather than over-planning 05:14.
Generational Gaps and Elder Influence
  • A key theme that emerged was the increasing division between generations, with the observation that younger generations no longer emulate their elders as closely as before 07:52.
  • The discussion explored how elders can lose influence by failing to communicate effectively or by being overly judgmental 08:50.
  • The concept of “elder” was reframed: rather than being strictly about age, it’s a relative position based on life experience and perspective 11:19.
Authenticity, Vulnerability, and Communication
  • Several points were raised, including the need for elders to approach others with curiosity and a willingness to learn, instead of assuming they have all the answers 12:42.
  • Listening to understand rather than to respond was highlighted as a crucial skill for building trust and co-created learning 14:01.
  • The conversation highlighted the significance of apologizing for mistakes and demonstrating a commitment to personal growth 15:07.
The Messy Middle and Lifelong Learning
  • The discussion explored the idea that personal development is an endless process—“the messy middle”—with no true endpoint 22:16.
  • Authenticity and being present were stressed as practical takeaways for showing up as a positive influence in everyday interactions 18:11; 20:17.
Reflections on Religion & Societal Control
  • Thoughts on how formal religion can foster division and fear, while noting the value of questioning and seeking personal understanding 24:17.
  • Comparisons were drawn between practical religious teachings and broader tenets of living ethically, using examples from Judaism and the film "Planet of the Apes" to illustrate human tendencies toward control and fear of the unknown 27:15.
Notable Quotes
  • “We co-create the magic in the moment.” 05:25
  • “The true definition of an elder is just somebody that is older … it’s a relative position.” 11:49
  • “As an elder, I think I’m learning that the best way to be in the world is to be curious and to ask questions related to that curiosity.” 13:10
  • “If you have this attitude like just because you’re older and more experienced that you know better, they’re not going to listen to you.” 16:36
  • “The messy middle is basically from the day you’re born till the day you die.” 22:38
  • “Listen and stay present.” 30:41
Resources and Links Mentioned
Quick Action for Listeners
  • Listen and stay present in your interactions this week 30:41.
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0:11 Yo, the Pipe Man is back from the last stop of the Pipe Man radio tour. Oh, and I have a lot to talk about about that. I definitely need to regenerate after that because it was, oh my God. Well, we'll talk about it more in a second. But first, let's introduce to the Adventures of Pipe Man, the one and only Captain David Gallimore. What's up, Pipe Man? He's trying to be me. Look, he's trying to be me wearing his shades. He looks like he's in Men in Black with these shades on.

0:56 I'm trying to channel my Pipe Man while I'm with you. There you go. I have to take it off a little. Oh, yeah, you are dark. I was going to say your shirt is dark. I was thinking men in black. Look, but he can't keep them on because then he won't be able to see crap. I can do it without seeing crap. Okay. So my first question for you, Captain, is why are you even here? That is such an existential question. Where to begin, Pipe Mountain? I'm here because I have a deep respect for what you do and who you are. And when you invited me onto your show, I said, fuck yeah, I want to be on Adventures of Pipe Men so we can have publicly more of the conversations that we have privately, which I always learn from you, my friend. Nice.

1:45 I love that. And so let's start off right off the bat. You have a show on our sister station, K4HD Radio. Tell us... about that show, let's first start off with what made you want to initiate doing that show? What were your goals? And then tell us a little bit about now that you've been doing it, have those goals stayed the same, evolved, or what you feel has changed from before to now? So I have to give full credit to Linda, who has a show on your W4CF, is that right? Radio station?

2:34 Very close. The one we're on right now is W4CY radio. CY, CY, yeah. You should know which station you're on when you're a guest. I should, shouldn't I? Duly noted. So she had me on her first show. which was she's in her seventies and she wanted to help bring on people to tell stories about the messy middle of their growth and what they were doing the next chapter of their life. And I had such a blast, but it was rebel meddler. You're one of your producers. One of your awesome, awesome producers. She's also usually one of my co-hosts, by the way, but at our studio in Louisiana, I just got off the phone before the show. Somebody shot through the window. No.

3:25 Is she okay? Yeah, everybody's okay. It just shattered the window, but nobody saw anything. The cops are on the way. So she couldn't be with us right now. Plus she's also, she's still engineering another show. That's how dedicated we are here is that we get, somebody shoots through our window. Your show's still going to keep going. It's the true measure of a pro, right? The show must go on no matter what. Exactly. So Rebel, just as we were finishing kind of a debrief with Linda, she said, you know, Dave, you have a voice for radio. And I secretly thought, thank God she didn't say I have a face for radio.

4:11 Well, you might have that too, but I'm not sure. Hey, hey, hey. So I then reached out to you And I was very much a newbie, still am, my God. Dean has had, to your listeners, Dean has had to educate me, not once, not twice, but multiple times on how this world really works. And I'm grateful. I truly am. And so the objective that I have, and it really hasn't changed very much, is how can I show up vulnerably and authentically at 64? neurodiverse, ADHD, wiring, retired corporate program executive, developed all sorts of businesses, entrepreneurial for IBM and Boeing, et cetera. But now really wanting to give back and pay it forward to next generation leaders who might not be able to afford my bill rate as an executive coach and a business startup coach. So this is my opportunity to You know, bring in fascinating people, as I know you love to do, and we don't overplan it. We co-create the magic in the moment. That's been such a kind of comfort zone stretching opportunity for me, who's usually very much a planner. As Dean will tell you, writes too many long texts and far too many long emails.

5:44 and tries to deliver too much value. So I can be taught, albeit slowly. And so the fun that I'm having and why I'm really delighted to be on your show is I'm starting to get some traction. People are responding to this idea that if we're gonna adapt, and I was listening to all the things that you were ranting about in a good way, by the way, our disruptive, turbulent, today and future and your evidence that you provided about triple digit temperatures at one of the last festivals, my belief and the consensus of most of scientists, geologists, climatologists, all of the different disciplines of science all over the globe have come to the consensus that human beings have probably more than their fair share, in addition to Mother Earth, who's in a receding ice age. So we're in this together.

6:41 And as a captain, maritime captain, we're in the same boat together. And what I want to do is talk with you and engage with these ideas that we have to work on ourselves, provide ourselves more resilience, ability to adapt. If we ever want to be able to be respected as a role model, as an elder, And so while we're doing that work, how do we show up then as our better selves with next generation, our children, our grandchildren, friends, family, et cetera? That's really what now is motivating me on The Regenerate Show and what I look forward to talking with you about on this show.

7:23 Well, one thing I do want to say, too, is I think we constantly have to regenerate in life. OK, and that's evolving, in my opinion. But I also want to say that sometimes people need to learn how to communicate for other people to learn. Because we're living in a world right now where people are arguing and attacking each other. You're not going to change people's minds. It isn't going to accomplish anything. So here's the thing, especially with the division of generations we have now. Like when I was younger, when you were younger... There was still the generations had conflicts, but we were closer match than we are now for sure. You know, um, we emulated the elders. Now we generally don't, we do the opposite, but I think that's also because of the elders and because the elders are not handling things the right way. Okay.

8:30 And perfect example. Climate change. How an elder can deny climate change when they know there was a nice age? So my point there is, there has already been climate change in this... Yeah, exactly. So why are you saying it doesn't happen and it's fake news, it doesn't exist? Like, if that were the case... you would be riding your dinosaur to work right now. Exactly. You know, so I think that's utterly ridiculous. But then again, I think the elders now more than ever talk so negatively about the younger generation that why would they listen?

9:19 I'm not, I wouldn't listen if I were them either. You know, I'm friends with a lot of the younger generation. Why? Why? Cause I don't do the same judgy crap that the rest of my generation does, you know, and you and I, although we're not many years apart, we are two different generations. You're a boomer. I'm a gen X. And there is such a difference there where I'm not. Now there wasn't when we were younger, but now here's the funny thing about your generation is how did the hippies turn into the yuppies turn into the boomers? There's something weird about that. The boomers tend to be the exact opposite of what they were when you were youthful. And that's the thing I have to say about the younger generations now. We don't know about Gen Z and Gen Alpha yet. Well, Gen Z a little bit. But millennials, you could see that they... They evolved, but they also kept true to who they were. Whereas the baby boomer generation, by becoming the boomers that we call the boomers, did not stay true to who they were. The liberals of the 70s and the 60s are now the alt-right of this decade.

10:46 Doesn't make sense to me, but that's true of a lot of what's going on too. It's like everything's kind of switched, but I think in order for the elders to have influence, maybe they need to understand every generation beneath them. And to me, the boomers are the elders. The Gen X aren't the elders yet because we're still a little childish. Okay. But we probably will be. So the Gen X can learn something too. Well, so I have a different definition of elder. I think if, Somebody is looking up to you. Yeah. And they could be 12 and they're looking up to somebody who's 14. True. They could be 24 and they're looking up to somebody who's 34. So my belief is that elders is not necessarily over 65, nor is it coming from a particular point of view.

11:37 I love that you're saying that because we've always been taught that the elders are the old people. But you're exactly right. The true definition of an elder is just somebody that is older. That could be- It's a relative, right? It's a relative position. And largely it's based on you fuck things up a bit as you get older and you have some life experience. And maybe that life experience, if shared to your point, in a way that meets the junior, can I call it that? The younger helps meet them where they are so that they can build a bridge, a communication bridge. so that that experience can be passed on so that we don't have more Darwin awards.

12:20 Right. So tell us a little bit about what being an elder is to you, meaning what it takes to be an elder that actually has influence. So my friend, I am still very much a work in process on this, but I'll tell you three things that I've learned, especially since I kicked the corporate crazy to the curb back in January of 2022, is one, I don't have all of the answers. So as an elder, I think I'm learning that the best way to be in the world is to be curious and to ask questions related to that curiosity. And you know this well because you're curious and I've listened to your interviews. You know, you don't bring, you have sometimes a point of view, but you don't bring blinders into that conversation. You remain curious and you kind of suspend your judgment until you've learned more. And I think that's a way of being that I've learned to be really, really helpful. Because then if somebody knows that I'm there to meet them where they are and really learn first and be curious to enhance that learning, they're going to be way, way more willing to share what they believe. And then now I understand where they're coming from. And now I can start

13:51 to link maybe some of my key ideas or elder wisdom, if I can call it that, in the appropriate ways, like might be video, it might be over a beer, you know, it might be on the water sailing. So finding those, those locations. So that's the first thing. Second thing I've learned is in the process of communicating, we co-create learning. If we're willing to really listen to listen and not listen to respond. So you're hitting on a point that's so important because Most people listen to respond and they're not listening because the whole time you're talking, they're thinking about how they're going to respond to you.

14:39 Yep. Yep. And then the last thing, and this was part of what I sent to you earlier, is because I'm imperfect, I'm a human being, not a generative AI bot, I'm going to make fucking mistakes. And I know that I can keep learning and to be a better husband, better father, better man, better sailing instructor, better coach. So bringing that growth mindset and modeling that commitment to growth. And when I make mistakes and I make them often, I apologize to my wife. She knows I'm still very much in training. I apologize to my son, Ian, who's 32, and my daughter, Catherine, who's 29, who I would give up my life. for those people, now my two new grandchildren, Daisy and Calvin. And so how do I continuously get better, even though I might be viewed as an elder from other people and they may think I have it all figured out and I don't think that serves them and it certainly doesn't serve me if I buy my own bullshit that I've already got it all figured out and I'm just opening up their brain, opening up the flap and then pouring wisdom in, that's not sticky. That's not going to help the next gen. It's not going to help society.

16:06 I love what you're saying too, because too many elders act like they know it all. And the people that they're mentoring know nothing. And I'm a firm believer. You can learn something from anybody. You can learn. They could be no matter what age, what their social status is, their job is, their education. They could be the lowest person on the totem pole and you can learn from them. And when you have this attitude, like just because you're older and more experienced and more wise that you know better, they're not going to listen to you because they can't even conceive of that too. That's another thing I think we have to cover because like there's things I'm learning now that I used to argue with my dad about, that I'm like, he doesn't know what he's talking about.

17:01 And I'm like, oh, I guess he did. So you were saying earlier about every one of us is an elder to somebody. What does that actually change about how we show up on a Monday morning, or in this case, Tuesday morning? So I really appreciate this question. It's so... practical. And I think sometimes conversations that I have on podcasts, you know, it's, it seems performative and, you know, very theoretical and all the rest, but okay, what are we going to do? I have a two-part answer to that. First, I think I suggest whenever we meet family, friends, bosses, employees, teammates, you know, just, just think of our relationships ecosystem that we traverse through, that we are committed to being authentic and we are committed to being as vulnerable as the situation will allow. Because I think people are so in need of psychological safety. When you look at all the root causes of lack of engagement in organizations, mental health problems in universities and in middle school and high school, there just really isn't a psychologically safe environment. I think as elders, we have failed miserably in creating environments where

18:36 people feel safe and can come and do their best work and their most creative work, be it in a family environment or a team environment, an organization environment. Certainly when I was a musician performing in a band in high school, you know, We were doing jazz and we were doing rock and roll and we had to trust each other that we were going to be able to have each other's back to allow that creative freedom to really blossom and to create the magic in the moment that the audience really resonates with. They feel the emotional connection. It's not performative. It's not just scripted. It's not pre-written.

19:17 There's a lot of nuance that happens in the moment when you're a musician, as you know well. So showing up authentically and vulnerably. And then the second part is to really be curious and to find out when you ask somebody how they are, that's not the typical American, how are you? And then you don't listen for the answer because you've moved four paces past while they were while they were answering. It's, it's just taking a moment and stopping. And when you ask the question, how are you? And, and somebody actually tells you something meaningful or real. Now that's the opportunity to listen, to be meeting them where they are to figure out if there's pain or opportunity that you might be able to help lessen their pain or enhance or accelerate their opportunity, that you are in service to that individual at that moment. And that's all you have at that moment. Alan Mulally, one of my mentors from Boeing days, who turned around Boeing Commercial during 9-11 and then turned around the Ford Motor Company during the Great Recession, he has a unique ability When he's with any one of us, and certainly he did this with me, I think I'm the most important person in the world. Even though this guy is the CEO of a multi-billion dollar corporation, I never felt that. I always felt that he was absolutely present. You can feel the

20:49 difference energetically. You see it in somebody's eyes. You create that connection, human to human connection. So needed, right? Given all of this accelerating change due to AI. Right. So those are the two things that I try to remember when I traverse, swim, sail through my ecosystem of people and relationships. Nice. And so now one thing I really want to know, and I say this not in the same way, but all the time. Why can't we finish our own work first and then lead others? I mean, listen. so many of us are telling others what to do and we haven't, we're not doing it. We're not walking our talk or we haven't finished doing it. Wouldn't it be more responsible to actually do the work first, then lead others?

21:49 So this is probably the best pushback on all that I've been saying. And I'm going to give you, my version of this and it'd be really fun to hear your version of this because I know you and I've talked about this in the past right how do we how do we be with our families even though we're still in the messy middle of our lives so so the short answer is guess what we're never going to be fucking done we're a work in process that's the messy middle the messy middle kind of teases that Oh, there's a beginning, a middle, and an end? No, I don't think so. I think the messy middle is what we're going to be in. We're in the soup. We're in the stew. We're trying to figure life out, and especially with all the turbulence and all the change.

22:38 Yeah, to your point, the messy middle is basically from the day you're born until the day you die. You know, the not middle is before and after that. Yeah, and if you talk to some people who believe in incarnation, and I believe in Einstein, that we're just in different forms. We just go from the current form that we're in to energy, back to energy. We become some other form, some other way. So there may be lessons even after and before the birth and the death, some people believe. I agree. Until I die, I won't know how to tell you what that's going to be like.

23:19 That's a good point right there, too, because Like, you know, I believe reincarnation is a possible thing. But I believe all of them are possible because until we do die, we don't know. And we may not even know then, especially if extinction is the one, because then you'll never know. So we may never know. And we tend to live our own life worrying about what we're going to do after we're here. Maybe we should worry about what we're doing while we're here. Bravo. I mean, talk about being curious. Formal religion, based on the studies and certainly of history, formal religion has often done a lot to divide us and to keep us, you know, othering others. And we've held up wars as justification due to religion. And yet we don't really know.

24:16 So that's being curious, right? I don't know. I hate to say it, but religion... is more about, I hate to say it, but religion's more about hate and fear and control than anything else. And that doesn't mean I'm against religion. I'm just not the person that, like I have my beliefs, but that doesn't mean there can't be other beliefs or they can't be doubt. Being a Jew, that's something we're actually taught as a Jew, is to question everything, question God, question the Torah, question the Bible, don't believe crap. OK, and that's why I gravitate more to that, because I don't you know, we don't believe in hell and damnation. We do believe in reincarnation. We believe in you keep coming back till you do it right. Then you ascend. I think that's a better idea. And that's more of learning than, oh, don't do this or you're going to hell. And this fix fictional character is going to make you burn. I don't buy that. I don't buy making people live in fear.

25:25 I don't buy making people live in control. I don't buy people that aren't even walking their talk, telling others and leading others what to do. Rabbis don't claim to be, you know, saints or better than anybody else or just another human being that had a little more education about their religion. We call them the teachers of the community. We don't call them people that are of a higher godly level. I'll tell you what, too, since we're on that subject just very briefly, I don't get the whole concept. Maybe you can explain it if we want to or move on, but I don't get the whole concept of how the leaders in a religion are the ones that can't procreate. That makes zero sense to me. Rabbis... can procreate and who else better would you want to procreate but the people that are the most religious and know the most about it i mean that's just weird to me.

26:32 Yeah i i i'm not uh catholic i don't know if there are other religions that espouse that as well but it just seems to me part of our human nature is being denied i mean our genes are all designed to have us procreate Exactly. It's the reason why we exist, frankly. We wouldn't be made to be able to procreate. If you believe in God, why would God want to make us to be able to procreate if he didn't want us to procreate is the way I kind of think about it. And I just think sometimes these man-made rules, because they can't be God-made in my opinion, are just silly.

27:15 Because Again, it dates back to a time of trying to control human beings. And sometimes I get it. Because if you go back to ancient times, and even now, man does not follow man's law. You have all these laws that are man laws, yet we have more people in prison now than at any other time. So what good are those man's laws if people are not following them? But I think the whole concept of religion came about because man will follow an unknown because of the fear of the unknown. And that's kind of how it was created. And very interesting, I don't know if you know this, but real quick, that's the whole concept of the movie Planet of the Apes, the original one especially, because it was written by an agnostic to prove, or not to prove, but to teach the agnostic point of view, which it's not that they don't believe in all this stuff, They believe in the concept of it. Like, you know, so if you look at, you know, plan the apes, what did they do? They copied everything from religion, but then they showed also how ridiculous it was that you had these, but then it had all these rules, but then the same token, it showed exactly what I'm saying about man will not follow man's law. So in order to keep the apes in line, They didn't tell them the truth about the scripture. Okay, which is what we do now.

28:48 We don't tell the truth about the historical facts of the scripture. Why? For a good reason. Because the humans blew up the world. So they didn't want the apes to learn that and then do the same thing the humans did. And guess what? You go to the third Planet of the Apes movie, that's exactly what happened. The apes found out That was all bull crap. And they blew up the world again. And I think that's the only good part of organized religion is that concept right there. Yeah. Well, I remember studying comparative literature, comparative religion, rather, at Yale. And, you know, I remember the Jewish faith really saved thousands and thousands, hundreds of thousands of people by... their recommendations on what to eat and what not to eat in the desert.

29:44 It just makes sense. And so that kind of, if I may call it practical religion, saved lives. Other tenets of religion, like don't kill your neighbor or don't covet your wife, those are probably pretty good things to also honor. Exactly. They're all good rules for being a good human. And the problem is we could talk on and on and on about everything. There's even things I want to talk about more with you. But we're not only out of time, we're late. So I'm happy to come back. It'd be a privilege and an honor whenever it's convenient for you, my friend. I had such a blast. Thank you. Thank you so much. So I'm going to ask you one last question before we go.

30:25 A quick answer. And you have to answer it quickly, not in David Gallimore fashion. Hey, hey, hey, hey. I represent that. One thing listeners can do this week. What is it? I would say listen and stay present. Stay present and listen. I love that. Couldn't be better advice. And so everybody make sure to check out the show regenerate, tell everybody real quick how they can check out your show, your website, your business, all that, and do it quickly. Yeah. So a regenerative world group.com is a website and info at regenerative world group.com is an email and the regenerate show on K4HD. com and K4HD TV and all the other variants of the talk for media empire that Dean Piper has My sensei, my elder, continues to make.

31:25 The world a better place. And see, I'm his elder and I'm younger. Now, what day and time to watch your show? Ah, thank you. Mondays, 10 a.m. Pacific. So what's that? 1 p.m. Eastern. Yep. All right. You heard it, everybody. Thanks for listening. Thanks for being here on the Adventures of Pipe Man. We're going to roll out of here. Thank you for listening to The Adventures of Pikeman on W4CY Radio.