HI 144 - Veteran on the Move & Support Systems with Joe Crane
7 Dec 2025 · 26 min
Episode 144 of the Heroic Investing Show (host Gary Pinkerton) features Lt. Col. Joe Crane (USMC, retired), host of the Veteran on the Move podcast. The conversation focuses on guiding veterans and military spouses toward entrepreneurship: why veterans make strong entrepreneurs (mission-focus, discipline), common pitfalls (working in vs. on the business, missing hard skills like bookkeeping), the importance of community/tribes during transition, and a broad survey of business types veterans pursue. Joe offers a downloadable entrepreneurship guidebook listing ~38 programs/resources for veterans and spouses and points listeners to veteranonthemove.com for more episodes and materials.
Questions this episode answers
144
Lt. Col. Joe Crane, Marine Corps (retired), AH-1 Super Cobra attack helicopter pilot
veteranonthemove.com
About 38
Chapters
Welcome to the Heroic Investing Show. As first responders, we risk our lives every day. Our financial security is under attack, our pensions are in a state of emergency. A single on duty incident can alter or erase our earning potential instantly and forever. We are the heroes of society. We are self reliant and we need to take care of our own financial future. The Heroic Investing show is our toolkit of business and investing tactics on our mission to financial freedom.
Hello and welcome to episode 144 of the Heroic Investing Show. This is a podcast for first responders, members of the military, veterans and really anyone looking to improve their financial future and gain some freedom with their time. We teach America's heroes how to build passive income, foster entrepreneurship, build their startup business and safely grow wealth through real estate and other alternative investments. We help current and prior first responders and veterans, active duty members of the military put protections and systems in place to enable them to build a life where they can focus on their passion. They can give back time with family, improve their financial situation and work on those hobbies that inspire them. We give them the time and the financial capability to provide that service or product that they are uniquely gifted to share with the world. Focus on their unique talents so that the world around them becomes a better place and in return their life improves. My name is Gary Pinkerton and and I co host this show with Jason Hartman. I think in today's show first we couldn't have a better fit and it's also opening up the door to some other tremendous resources that are perfect for this audience. I have been living somewhat of a parallel life with my friend Lt. Col. Joe Crane, Marine Corps, retired, AH1 Super Cobra attack helicopter pilot. He lives the state next door to me. We were in the military for the same years for almost the same length of time. He finished up his time in 2013 and mine in 2016. We're both running a podcast aimed at fostering entrepreneurship and helping active duty members as they transition to veterans and this applies as well in the in the first responder world, going from exclusively focusing on that salaried W2 income and working all kinds of crazy hours, deploying very frequently transitioning into something that is their own business or at least a nice transition into civilian world. Joe's show, which is called Veteran on the Move and you can simply find it at veteranonthemove.com is focused exclusively on providing tools for individuals who are interested in entrepreneurship. So ours has a little bit more of a real estate and passive income bent and it doesn't predisposed that you will head to starting your own small business. And entrepreneurship kind of blends the gap between the two. Joe's is more focused exclusively on entrepreneurship, and so what he does is he interviews people in a fantastic podcast series that provide ideas and tools to help you make that transition and be successful in entrepreneurship. The tagline for his podcast is your Pathfinder to Freedom. And in reading just a small bit here from the Veteran on the Move website about Joe's purpose with this, he says that your Pathfinder to Freedom's purpose is guiding veterans in their transition to entrepreneurship. He interviews today's most influential people in the world of entrepreneurship. And this whole program, Veteran on the Move, is about promoting the ideas, tools and resources available to today's entrepreneurs. We want to help you find the tools and resources needed to start your own entrepreneurial journey. So I think that does a great job of capturing what we talk about in our interview together. I won't spoil it won't be a spoiler for what Lt. Col. Joe Crane has to talk about. I think you will really appreciate it. And when you go to his website, check out his most recent podcast that he just aired or a very recent one was episode 232 and it's the when he turns the table on me and does an interview of me and I had a great time in both of these podcasts, I think both of the audiences have an opportunity to learn greatly. I think they're probably a very much shared audience. But if you haven't heard of Joe's podcast, please do go over there to Veteran on the Move and check it out. He's got some tremendous resources there and make sure you download a couple of the books and resources that he talks about in our interview and that you will find on his website. So without further ado, man, I am tremendously humbled and proud to have made the connection and feel fortunate to have made the connection with Lieutenant Colonel Joe Crane. And I think you're really going to appreciate this interview.
Well, everyone, thank you again for joining us here on the Heroic Investing show. And as I mentioned in the introduction, we have an incredible special guest, himself a podcaster and I think been doing it a little bit longer than me, but I'll have to check on the, on the details of that. We we have with us Mr. Joe Crane, somebody who has been in the military as long as I have. Flew a little bit different vehicle though, and I'll let him introduce that he runs the Veteran on the Move podcast. Joe, thanks so much for joining our group.
You bet. Gary, thanks for having me on your show. Really been looking forward to this because I'm usually on the other end of the interview, I'm asking the questions and so I guess now I get to answer the questions. So it'd be a little bit different show for me. I don't do a lot of podcast interviews, believe it or not, even though I'm a podcaster, I just do busting interviewing.
Yeah, very similar. We're running parallel lives here because actually everyone I'm going to be interviewed very graciously on Joe's podcast when we're finished or you know, it will run somewhere around the same time and that'll be my first as well, with the exception of of course being on Jason Hartman's and a couple of times on Patrick Donahoe's Wealth Standard podcast. So I haven't done many, probably less than you, Joe. And so thanks again for joining us. Can you tell my listeners a little bit about why they should go listen to Veteran on the Move and you know what your target is because I think it's pretty similar to ours.
You bet, Gary. So the entire time I was, I was in the Marine Corps, I was, I was a Cobra pilot in the Marine Corps most, most of my career. Active reserve, active reserve. I actually was in the cockpit except for just a handful of years. And the entire time I was in the military I always had this entrepreneurial urge. I was always messing with something on the side. I spent my free time, weekends, time on deployment, reading books, talking, anything to do with investing, real estate, investing, even played around with some multi level marketing companies starting my own business. It was really before the early days of Amazon. You know, running an online business wasn't really easy at that time. But I messed around with affiliate marketing, you name it, I've probably touched it or looked at it over many years a couple of decades while I was in the military and I said, you know, when I finally retire from the military, I'm going to dive deep into this entrepreneurship stuff. And my last couple years I spent, I was one of the Marines on the staff at the Army's Command of General Staff College in Fort Leavenworth. And it was the deputy director of the Marine Element, which is a fancy name for the xo, basically just a small detachment where we, we basically dealt administratively, a little bit of leadership wise with the Marine students were going through the army course of year. So academic environment 9 to 5, no duty, hardly any travel, no weekends, no holidays, you know, all that. So really good deal. I decided I Knew I was going to do something in entrepreneurship, but I didn't know what. And it was a couple years away from me. Retiring opportunities coming up. I'm like, you know what? Why don't I go use some of this tuition assistance, some of this extra time here in the aggregate environment? I'm going to go get a master's. So I went get a master's in entrepreneurship from Oklahoma State, and I said, at least I'm getting something that can be put on a piece of paper. In doing so, I knew that I was going to go back to my airline job that I had before September 11 happened, and I got furloughed. So I knew I really didn't need to pad my resume with an MBA and try to impress somebody to go get a job in corporate America. I knew I was going to go back to the airlines, and I was going to go in entrepreneurship. So I wanted to study entrepreneurship because the first time I went to college, you couldn't get a degree in entrepreneurship that didn't really exist. And so I was incredibly excited about studying and being immersed in the world of entrepreneurship, even though it was in an academic environment. So that's what I did. I finished the degree right before I retired. And I found that it really opened my eyes to all of the different programs, people, and resources that are out there to any budding entrepreneur, but even more specifically to people from the military community, veterans that want to go into entrepreneurship. There's a lot of resources and programs out there, many of them being free, that you can get involved in to help you get your business started, even to help you discover ideas if you don't even have the idea. And I was totally ignorant to all this stuff when I started. And when I came in on the other end, I'm like, holy cow, there's so much good stuff out there. But I bet you most veterans don't know about them. And that's where the idea from the podcast came. So I started Veteran on the Move. And my goal, and this was four years ago, I was going to interview mostly veterans that have become successful entrepreneurs. I've also interviewed a number of people that run programs from different colleges, universities, different nonprofits. There's a lot of great programs out there that help veterans transition and transition into entrepreneurship. I've interviewed a number of them. So my goal was to interview anybody that has, you know, either can tell their success story in entrepreneurship or runs a program that will help anybody from the veteran community, military spouses, veterans, themselves, if you're still in, if you already got out. Anybody in that niche that wants to go into entrepreneurship. If you listen to veteran on the move, you'll be hearing like minded individuals tell their story or talk about programs out there that can help you get started and be successful in entrepreneurship. And I've been doing that for four years now.
Wow, that's fantastic. And so you're doing what, one episode a week or a couple episodes?
When I first started, I was doing two episodes a week to try to gain more downloads per week or downloads per month.
Right.
But two a week became.
It's burdensome.
Yeah, it became burdensome and it was just too much.
Yeah.
And believe it or not, there's a lot of people that can soak up a podcast a day from a particular show or whatever. But believe it or not, most people are, you know, they may have five or six different kinds of podcasts they listen to. So one episode a week is kind of the sweet spot for a lot of listeners. It's also the sweet spot for most podcasters.
Yeah, I agree. That's really what I've experienced as well. I do one and then we do kind of a flashback Friday or, you know, one of the best from the past on a related subject. So, you know, very, very similar to your approach. And so you have now, gosh, you got a couple hundred episodes out there. You've probably had the opportunity to start to compile some common themes that you hear from the entrepreneurs that have been interviewing. And can you share some of those with the audience? I think that may be some of the best material, the best use of their listening time.
Oh, yeah. The thing that comes to mind first and foremost is all the things that make veterans great employees are very similar to all the things that make veterans great entrepreneurs. And if you can be a soldier, if you can be a pilot, if you could be an infantryman, if you could be a Marine or Navy SEAL or any whatever it was you did in the military that you excelled at. If you can do that, then you can do entrepreneurship. You can be successful at entrepreneurship. Veterans are very mission oriented. We're very mission focused. So we have a lot of these great soft skills like leadership and discipline and just that deep reach deep down inside your gut and never quit and never give up, which is what you need to be successful in entrepreneurship, because you're going to hit a lot of obstacles. And we'll find that veterans possess so many of those great core skills that are required to succeed in the business world. On the flip side of that, no matter who you are, what you did in the military, you're probably missing some of these hard skills. Like you might not be an accountant, you might not be good at bookkeeping, you might not want to do bookkeeping, you might not know much about taxes or business structure. And that's okay. You don't need to become an expert on those things. Matter of fact, you're better off if you don't become an expert at those things and spend your time doing that. You really need to maintain your focus on the pointed end of the spear so that you're the one with the big blue arrow mentality on where your business, where your company's going and you bring in people that are experts at those other things because those things still need to get done. And this is not just true with veteran entrepreneurs, it's true with all entrepreneurs, especially solo entrepreneurs. It's so easy to get overwhelmed with all the sidebar stuff that really it's got to get done. But I almost want to say it really, that the stuff that doesn't matter because if you're spending all your time doing accounting, bookkeeping, sending out sales invoices, paying the bills, if you spend all your time doing that, you're not actually working on your business, you're working in your business. You're being consumed by your business. And you might feel you might be really busy, but if you take a step back and look at it, you're not being very productive. And so that happens real early, real easy and early on in a lot of entrepreneurs, businesses, and then they wonder why they're not making money or they're not making enough money. It's because they're swamped with the day to day grind. Instead of getting out there and doing what they originally set out to do, and that's to deliver that great idea, that great service or that great product, and they get caught up in the minutiae of things and eventually fail.
Right. So great points there. And one of the, you commented that one of the things that make veterans very good employees also makes them great in entrepreneurship. And I think everything is exaggerated in the entrepreneurship world. You know, if you don't want to get up and go to work as an employee, try doing it when no one's holding you accountable as an entrepreneur. You know, it's going to be tough worried about the changes in cash flow or not making the numbers. I mean, that's magnified big time as an entrepreneur. And I don't mean to scare people off, but going from a great month to a month where you didn't even make anything balance or no sales, it's wholly possible, especially when you have a new, you know, kind of fledgling company. I think other things that members of the military and first responders do, people who have been leaders in, in stressful situations, the things that they do is that they have a great support structure. Right. They have friends, they have family. I mean, think about the family that follows you around everywhere and redeploys all the time with you. Right? That's a pretty strong. They may not like it, but it's a strong family unit. And the same thing with friends that you've been in battle with or that you've just gone through really unfun training events with, whatever. They're really good people. So you got an incredible support structure to back you. But ironically, actually, I don't know what the statistics are. Maybe you do. It's my feeling that not a lot of military go out and become entrepreneurs after they retire. Is that true or no? Any idea?
Yeah, actually, the percentage of the viewed as a percent of the population, military veterans are twice as likely to go out and start their own business than the regular population.
Really?
That's awesome. That's awesome.
So. And often, you know, you know, shout out to military spouses out there. Oftentimes it's the military spouse that's the entrepreneurial one of the couple, you know? Yeah, there's a lot of military spouses doing phenomenal things with their businesses. Some of them. A lot of their businesses have nothing to do with the military. And some of the military spouses have embraced their experience as a military spouse and involved in veteran issues and transition and all that. And they're right all, you know, right up there in the middle of all of the military issues with their business. So I always jump at the chance to have any of the military spouses that are running successful businesses on the show just as much as I do the veterans, because there's plenty of them out there that are doing great things. So it's always good to see.
Yeah, exactly. Well, certainly they've had to pick up the pieces and be able to adjust when schedules change and they're kind of left holding the bag. My wife certainly saw that numerous times. That makes a lot of sense to me. I'm surprised that at least people who have done a longer career, we get very dependent. I don't know how to say dependent, but we become. Our comfortable space is around having some rules and regulations, operating procedures. We value kind of consistency and things like that. So those don't necessarily cause you to want to leap out there and hope the road gets built under you. But I can certainly see that with military spouses, no doubt. Can you speak a little bit to the types of businesses that you see people starting? Is that, is that also fully across the board? Is it, you know, franchises and, you know, creating inventing new widgets?
Oh, I tell you, I. I've got no common team whatsoever. It. It's completely across the entire spectrum, you know, which is good to see.
Yeah.
There is no stereotype whatsoever for what veterans are going to go into business with. I've seen it all. I've seen it from cleaning companies to mowing grass companies, taking a lawn mowing business to over $4 million a year in revenue with government contracts and to high tech stuff, invention of products, providing services. It's across the entire spectrum. There's not even like one, even a theme of anything that comes to mind when you ask me that question. It's everywhere. Yeah. It's good to see.
Yeah. That's awesome, Joe. And I appreciate you sharing that audience. I mean, these guys have heard me spout probably too many times my vision and what drives me and essentially that is to help other people, to help enable people to get back to what I think our founding fathers were looking for when they put in place the American dream. Right. The American dream is to have the ability to provide for your own family, to have things that you want, have a rule of law behind it, so that when you create something, you. You reap the benefits of it. And a lot of that comes from small businesses that we saw as kids, or maybe you're not quite my age, but I remember seeing back on the farm, if I needed something, one of my neighbors was making it or somebody in the town was making it, and it wasn't all coming from overseas. And so I believe that we have a society of people that are more confident and they're happier if they're able to get up every morning and add value and get compensated for it and kind of control their own destiny. That's really what drives me. Sounds very similar to why you're trying to nudge people in that direction.
Absolutely. And we talk about all of the issues associated with transition. Transition out of the military doesn't matter whether you're the service member or the military spouse or even the kids, Everybody goes through that transition when you either get out or retire. And it's so vital. I firmly believe. I'm no psychological expert by any means, but I firmly believe that the veteran suicide rate is so High because so many of us lose our sense of purpose when you get out of the military. You mentioned earlier about that support group you've always got around you and we may PCs all over the place and pack up and leave everything around us and move to different places. But oftentimes when you get to your new unit, there's some guys that you knew from initial training, or there's some guys you knew from your last unit, or there's all the people that you plug in with when you get there are very like minded from the people you just left. So it's not like, especially the military member themselves, it's not a really big change because they're leaving one military unit, going to another and there's change there. But when they get up and go to work, they were in the same uniform they were at the last place and they're surrounded by like minded individuals. And so it's not that big a transition. But when you get out or you retire or you go work, you get hired at some civilian corporation or you go into business for yourself, all of that's gone.
Yeah.
And even if even though you know it's coming, sometimes you don't realize the impact it's having on you and your spouse and your marriage and your family and you sometimes guys don't realize it until it's too late. And it's so easy to have that happen. So that was really one of my goals for the veteran on the Move podcast in the community was to provide access to a tribe of like minded people. So if you're getting out of the military and you want to go into entrepreneurship, you need to surround yourself with people that are a little bit farther down the road than you, that are already in business, that can walk you through those struggles and roadblocks and obstacles and help you along the way.
Right.
Put you through some of those tough times. So when you leave the military, you lose that culture, you lose that community. You need to figure out how to quickly replace it with something else that's healthy. Not your buddies down at the bar. But who can you get around the beauty of entrepreneurship? The one thing I love, I love the military mindset. I love being around Marines all those years eternally warped and twisted because of 24 years of being around Reeves. But I loved every minute of it. And of course you always miss the people more than anything. But entrepreneurs are like the next best thing. People that are entrepreneurial minded, they're very mission oriented, mission focused. It's much like being around your buds in the Military. It's very similar to that with most ventures. So it's a very invigorating sport to be involved in. And I would be analogous to playing a sport because you practice a lot, you have game days, you win some, you lose some, you go back, you practice some more, and you go back out again. So even though you're even, you may be a solo entrepreneur, but you need to get, you know, whether it's a mastermind or Facebook groups or, you know, the vfw, wherever you can find your tribe, you need to go get involved in it and get plugged in and stay. Get people around you to have your best interest in mind and speak a language that you want to learn. Speak a language that you speak because you don't want to be floating around there all by yourself because you will lose focus, you will lose direction, and then you'll just be spinning your wheels, not going anywhere. So it's, it's. Enjoy the fact that you can be a solo entrepreneur and run your own business, but don't think you can do it alone.
Yeah. So that was an awesome comment, Joe. And being on an island is certainly a good descriptor for being an entrepreneur. You mentioned before about creating a community, about creating the tribe. As we come to a close here, Joe, what do you have or what would you recommend? Maybe something, some resources you have at Veteran on the move or specific episodes or anything like what would be a next couple of steps for members of the heroic investing show that got inspired by what they heard Today on my.
Website, I've got a free download which is several years old, and I've come out with an update to that. I have not posted it on the website yet, so it's not available. The old one's still available for download. The new one is not. I call it my entrepreneurship guidebook for military folks. Anytime I hear of a great program that would be beneficial to veterans or their spouses or anybody from the veteran community, I would write it down. And so what I did was I got close to about 40. I think the list is 38. There's 38 great programs for veterans and their families that they can go get involved in to help them get involved in entrepreneurship anywhere from mentoring programs to incubators. Some of them are government run. Some of them are run by universities. Some of them are nonprofits. A lot of them are free to veterans and military spouses also. So if somebody wants that guidebook, just haven't got it up on my website yet. You can send me an email and I'll give you my email address. It's Joe J. O eteranonthemove.com if you send me an email and say, hey, Joe, send me the guidebook, just send it to you for free.
That's awesome. I'm doing it right now. Thanks so much, Joe. It's been tremendous having you on our show. Thanks so much and can't wait to join you on yours.
All right, Gary, yeah. It's been great talking veteran entrepreneurship with you and thanks for having me.
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