Ep 37: Shane Pilgrim: From Military Veteran to Business Advisor - Embracing Transitions and Redefining Success

Show Notes:

Intro 00:00 – 01:54 Shane Pilgrim I appreciate that, and I'm glad you enjoyed it. Yeah, just talking about the transition.

Story behind his Alexander Hamilton socks
01:57 -  03:00 Shane Pilgrim Yes, sir. No, they're both Alexander Hamilton. The story behind the socks is my good friend Todd Simmons is a big sock connoisseur, and there was a period where we were having this sock war on Facebook and going back and forth and, who had the toughest socks. When I'm speaking I  to say,  I'm channeling my, my Alexander Hamilton, so, I got these socks. I can't remember. No duels. Well, maybe a verbal duel or a mental duel, A battle of wits, but no shooting here. I  to wear these socks just to kind of remind myself that it is okay to think differently and be a maverick and be visionary and creative and sometimes  great things come out of that. So I'm just a big fan of Hamilton, big fan of the music and, and rock the socks to suit.

The Challenge most service members have with thinking differently and their first year after exiting the military
03:10 – 08:05 Shane Pilgrim Yeah, well, I mean, the obvious challenge while you're in is the hierarchical nature of what we do and in a lot of cases there's an expectation that you get to a certain level before you have vision and leadership and creativity when the opposite is actually. True, which is you're born with certain God given talent. I believe that I'm creative in the way I think is because of a product to the talent God gave me. Plus, the environments that I grew up in growing up as a special operator, what I told people earlier today when I spoke was about, I had a boss that told me as a young E4. One man could change the Air Force and I really ascribe to that and I always try to do things regardless of the structure above me, the pressures and all that I was always  hey, why can't we challenge the status quo? Why can't we do things differently? And I think it led me to continue as a special operator, because in that environment, it was actually valued  it was more about your capability and less about your rank or position in terms of what you could do to affect the mission and how much responsibility even you could have. And I was lucky to be in those environments. So I just kind of found places where They appreciated divergent thinkers and did it. And I mean, even if I wasn't, if I was somewhere where it wasn't, I did it anyway, right? Because I'm going to be me at the end of the day. And, , it's okay. If you're a true leader, then you're okay with somebody challenging and challenging assumptions, because that's how iron sharpens iron. That's how you get better. How do you balance that, , after the military? Just challenging assumptions because, to me it's a different battlefield and there's so many skills that, We learn in post military life,  the difference is that people want to make money. So if you challenge assumptions in a way that creates more revenue or drives more innovation you might find yourself really appreciated. There's obviously a structure everywhere. There's a boss. I work for myself, but I also have customers that I'm beholden to, but I know my strengths and I know that, freedom is one of my values, freedom in terms of supporting our way of life and supporting our country, but also supporting the way I think and the way I  to move. And so I find places to work and people to work with that appreciate that freedom and want me. And once you find that sweet spot and help them make money, then yeah, they're all about it.  In industry, innovation isn't  a buzzword or a thing that we do to stay ahead of,  it's about staying ahead of the competition, which directly affects your bottom line. So it's a necessity,  we're saying it's a necessity, but in practice, a lot of times in the military, it's, they want the status quo. People want comfort. They're not as comfortable with change. Industry has to change to survive. So, you might find yourself as a maverick being more comfortable on the outside than you are on the inside. If you don't  change, try irrelevancy. I think there's necessity in the military. There's just a ton of bureaucracy and there's not the need for a bottom line. We're conditioned to spend money, in business to their condition to save money. Again, if you can prove you may have the best idea in the military and I still don't think we're at the point where  immediately it shoots to the top of the pile and it's executed  you've got to go through these echelons. In industry, they're thirsty for, Hey, you got the next best idea and, and it can get us there now. They're far more thirsty for it I find.

After being retired, looking back on one skill he overlooked in the military, but now realize the value?
08:28 - 11:55 Shane Pilgrim I always thought that my network and the people that I had befriended and helped and that had helped me in the military, I never looked at it as something that was marketable that would turn into a career for me. I think that was good and bad. Good because I was friends with people because I was just genuinely friends with people. I was helping people because, I get a certain satisfaction, that's how I actualize is kind of growing other people and helping people out. And I take a lot of pride in that and I get fulfillment from that. But then, I transitioned and people were willing to help me. I probably hadn't talked to in a while or thought about in a while and I thought it was really kind of cool things that I had invested in for the right reasons turned out to be things that helped me on the outside without even ever really thinking about it. So that's what I would say is  my skill at networking. My friendships, my relationships that I had nurtured and just the way I had treated people. Actually, you don't think of that as a skill, but being a good teammate and being a person of respect and that treats people with respect and a person of your word. When you come around on the other side, people know it's still you. And you have more, you have less transactional relationships because a lot of the military relationships can be transactional. I work for you and I need this relationship because I want you to help me. And then, but when you're giving to people  And then it comes around and you're , Hey man, can you help me navigate this maze? Or, I need some information on X or Y. They're absolutely and I remember that time, which I'm , oh, yeah, sure. But I don't even really, might not even remember it, but , people come up to me all the time and go, Hey, man, you helped me out with this and I really appreciated it. And everybody should strive for that.  At the end of your career, that that should be a marker of successes. How many people you touched and how many people you helped uplifted, whatever, not necessarily how high you rose on the totem pole. It's in my wheelhouse to act that way and be a good teammate because I grew up believing the team and the person on the left and right were everything regardless of the circumstance. And now I find teams that are  fun to work with and it's fabulous. This is great, everybody I work with. It's just like I was still in the military.  I have great teammates and we do things socially and blah, blah. And I, I still have my military network of friends.  I come here and I can't walk through the hallway. That's a great space to be in as a person is being widely connected and having a lot of connections.

How a failure, or an apparent failure, set Shane up for future success
12:08 – 14:09 Shane Pilgrim I think I've had many failures.  Ha ha, a favorite failure story. I wouldn't really consider it a failure, but I talked about... and directly related to transitioning. I got out and I went to work immediately for a friend of the family in a director role in a small company. I think  I jumped the gun in terms of probably should have took a little bit more time and been a little bit more deliberate, but some of it was some anxiety of, Hey, this is a good job. I know the people I don't think I took the right amount of time to really look at my options. And I don't I think I ended up…I was there probably about six or eight months and then I transitioned. I learned a tremendous amount about business. I learned a lot of things, but it wasn't necessarily the experience. It didn't pan out the way I thought. In terms of success, I hold nothing against those guys, I mean, they are great human beings, and they gave me an opportunity and I'm forever grateful for that, but I wasn't a cultural fit necessarily, it was too much of a transition coming out of the military, it didn't work out the exact way I wanted, but it's not a complete failure because I learned a lot, I learned about myself and sometimes learning what you want is as important as learning what you don't want. And it's okay to learn in the civilian world and then move on to something else. And from that, I moved into running my own business. Some of those skills I take with me.

If you are not networking you are not working
14:10 – 15:22 Shane Pilgrim Yeah, 100% true. Everything I have a large majority of it, I've gotten through networking on my boat charter business. A lot of it is Marketing and repeat business. But it's the same kind of networking skills. The ability to connect with people and remember them I have in the boat business. We'll have people that charter with us two or three times a summer and have been for the last three years while we've been in. Longevity. Those things are important and it's the same skill in networking, you see people especially in in business  in the tech industry and other industries I work in you'll see people and you'll see them again and again and they remember you or they  you remember something about the conversation and, then it turns into a kind of a budgeting relationship and then blossoming relationship and they want to work with you. That’s turned into business for me and turned into me being successful.

2-3 books Shane recommends about networking and transitioning he recommends. Also, same advice for podcasts, articles, and YouTube videos.
15:23 – 17:57 Shane Pilgrim I'm not a big reader, but I have read some business books. The attention for it is where I struggle. Some of my favorite books, The Millionaire Next Door and I don't know if you've read it, but it's about a guy that did marketing and he studied people that were worth two to 10 million and wrote a book about their habits and their spending. The essence of the book is that the millionaire that you think, Shaq and Kobe, it's actually a guy in a middle class, the majority of them. Middle class neighborhood, not the biggest house in the neighborhood, driving a Ford F150 or an older Mercedes, just facts about what these people spent their money on and how they spent their money. And I think that's essential to what I talked about today in terms of the preparation. The preparation that gives you the ability to take bigger risks in terms of where you work and how you work and how much you work those habits Good to Great is a tremendous book. And it's just about building a business and waiting for the point where, why certain businesses took off at a certain point. It was just little things that they did along the way and kept going, pushing a flywheel is what they call it and then at some point it spun off. Trying to find that moment and having the patience to wait for that moment and make the right decisions along the way. So those two are really good. What's another book I  really liked leadership Secrets of Attila the Hun because it talked about Attila as a multidimensional leader, not necessarily just a vicious killer. He did kill people, but it was always for effect and for a message. He also spent time in the Roman court learning diplomacy. He wasn't, he hated it there, but he took everything he learned there and turned it into success on the battlefield and use it against them in multiple ways. So I think that kind of strategic thinking and that openness to exposing yourself  to other things, or learning while you're exposed, not intentionally are skills that transition to life and transition to business.

On Admiral McRaven
17:58 – 18:58 Shane Pilgrim Yeah, I'm a big admirer. He was the JSOC (Joint Special Operations Command) Commander while I was serving there. One of them that I served under. And I've met him. I got a picture with him in my house. yeah, big fan because of what he did with POTF and the risks he took for preservation of the force and family as a Commander. I will always be an admirer of Admiral McRaven.

Keys to establishing, establishing a unique style without getting pigeonholed
19:16 – 23:31 Shane Pilgrim The first thing that comes to my mind is what I talked about in that panel, which is what makes me unique a lot in the outside world is that I did many different things. I worked in special operations. I worked in airlift. I worked in testing acquisition. I worked on a joint staff. I worked, in presidential airlift, so I had this kind of smorgasbord of experiences that when I go to companies and they ask me, what have you done or, we just have casual conversation I was , yeah I did this and I did, and they're , holy cow, man, , , what, what didn't you do? That gives you a kind of confidence and I think, from a stylistic perspective is born of a growth mindset. I wasn't afraid to try new things. I didn't fear  when they said, they came to me at when I thought I was going to retire and said, Hey, we want you to help stand up the Space Force. I didn't fear that. I love the challenge because I was, okay, everything is going to be different and it's all about change and being creative and that's my style. So I'm , all right, I mean, I wasn't planning on doing this, but , I'll give it a shot. And I had the right teammates, Toby Towberman and K Wright telling me, which is another part of my style is I have friends that I trust and teammates that I trust that can see my blind spots and also see opportunities for me. My style is I rely on my close circle to point those things out and that's I think that's worked really well for me. My style is to always be growing and willing to try new things and be creative and that's key right there. It was something that, when I got out, I wanted to capture my individuality. I wanted to not be the same person I was. And I come places here and people call me Chief nonstop and I take that in. I appreciate that respect. But, once we get into the conversation, I'm immediately , Hey, my name's Shane, you yes Chief. That's what they normally tell me. But , I just, part of my style as well is. To be an individual, right? To, to transition from the military and transition into, into individuality, a lot of which I either suppressed or I had certain rules that, that I kind of colored within to play those parts and play those roles. And now I want, again, freedom is one of my priorities. So I want stylistic freedom. I want creative freedom I want financial freedom, and everything I do lays out based on my values that's pretty important to me.

One of the best or most worthwhile self-investments he made in the past six years
24:46 – 28:37 Shane Pilgrim One, taking the job to help stand up the space force, I felt was a self-investment and I didn't see it that way at the time. That was 2020, so the first two years of the standup, I was there. And I because it was  a chance, It was a risk. I could have gotten out. I could have gone into industry at that point, but I chose to kind of invest in my passion and invest in people on that team that I trusted were like minded and doing something historic and cool. I also, during that time, well, during the last six years, I invested in that boat business that I started with, with a business partner. That was a pretty cool investment. Started as kind of a side hustle with a tax benefit that turned into  real work and real business, fortunately, but during the time I was at Space Force. It was pretty stressful because we had so much work to do in such a short time and I had joined a CrossFit gym at the time. So  I actually was investing in my health while I was under a lot of stress and I thought that was really good, CrossFit, it's  a cult right, somebody does CrossFit because they tell you in 30 seconds. I was in Old Town CrossFit at the time and in Alexandria. I look back and I was reflecting today because I spoke about commitment today and about the Space Force values, which was, was my project. As I was talking through, how hard it was and how much work it was, man, how did I handle that? And then I remembered that it was really CrossFit and I was in the shape of my life. I had never been in that kind of shape, insane shape. I was in my forties. Yeah and to get to that point, at this point in my life, it was awesome. I think for my health, I need to get back there because I got lazy since. But yeah, that investment in health and in energy to produce more energy to do the work that I needed, which was an investment,  and also to start this business on the side that then got really busy. I think those were incredible investments. Yeah, I'll say that, and it's not  a traditional investment, , but you can look at an opportunity as an investment and a lot of people don't do that. By taking this opportunity, the things you learn, the growth you have, the things you're able to, to achieve that follows me now for the rest of my life, businesses that I work with, I don't, I try not to lead with my resume, but they'll do it for me. They'll be Hey, this is Shane and he was on the space staff and he was a guy. Did the values, and they're super proud to be working with me because I did that And I never thought , okay People are going to want this to be, yeah, I was just this is something cool that I did but to them  It matters that I did that and it’s really cool to have.

Bad advice he hears often regarding people as they are transitioning out of the military
29:22 – 38:10 Shane Pilgrim Oh yeah. Money talk is sometimes poisonous. This is when money is poisonous. When you have an expectation and it's okay to know your value, but when you set a number on your value,  your value is so much more than a number that people pay you. It could be benefits. It could be the team you get to work with. It could be an incentive package. People going into a job  saying, Oh, I'm not taking less than this. And sometimes their numbers are ridiculous and I'm , yeah, no, how about 200,000 and you really only worth 130. You can't tell them that because then they get a hurt feelings report. We tell them anyway, or I'm ,okay, let me know how that works out for you. Money it's, it's not the be all end all. I incidentally, I have a friend just took a 50,000 a year pay cut and I won't mention who he is or what, but was in a job, making 200 and was miserable. Took another job for 150 and I was ,dude, I have so much respect for that action because so many people talk about do what fulfills you and do this, and then they go to company X and they slave because they become a slave to a lifestyle, they become a slave to bragging to their friends about what they have and what they make when that's not really a fulfilled life. The fact that he took that action because he was saying for months he's, I'm miserable, I hate it I don't want to go there anymore , he's yeah, they're paying me this and doesn't matter. I'm miserable and then he took action on it and I was  man bravo to you because so many people stick it out. They get comfortable in that that money. That's a big one. The other one is  I talked about people going, Hey, how can I be you? I never want to hear that question. You are not going to be me. You're going to be you. You may do similar things. How can I be in that industry? How can I, is such a misnomer that you're going to be me and you don't know my life and you may not want it. It's not easy. Trust me. I just kind of get thrown off and I understand  what people are saying. They're not coming from a malicious place, but I'm also kind of, man, you're not asking the right questions and that's a mistake and a missed opportunity because a lot of times people ask a question. And they already have the answer in mind that they want, well if you do this, this, and this, A checkbox, right? Yeah, here's the boxes to check. And then, shazam, you're me, sitting here in a suit doing a podcast. No, That's not how it works.  So I watched a series and I thought it was really good, and then I sent it to my son. I wanted him to watch it as well. The philosophy is sound. You may find that the number you need to do all the things that make you happy is far less money does not make people happy It's proven, the suicide rate among rich people is just as high. It's a people issue. What do you want to spend your time doing? What do you want to spend your time? Who do you want to be able to spend your time with? There's so many other intangibles that have nothing to do with how much money you make, or that can be done without chasing a number. Financial advisors will do an analysis and tell you, Hey, this is the number you need to live the current lifestyle you're living. So you need to decide is the way you're living right now, really your rich life, or is it just the way you're living right now?  I don't fixate on numbers. I almost got in a fight one time with a dude in a bar because he was so mad at me  for not, cause I, I don't care about my number and he's you gotta know your number. And I was, well, no, I don't. And he's, what are you talking about? But, yeah man, money is poisonous. Not money isn't poisonous. Fixation with money is poisonous. And it, it ruins people in a lot of ways and I see it very often, and I think it's a problem or I wouldn't mention it. Learn how to handle money, learn how to manipulate money, learn how to save money, most importantly. Because there's a discipline of not being there yet, but there's also a discipline when you get there, which is something  I would have loved to talk about entrepreneurship all day today, but What do you do when you retire and all of a sudden you're making a hundred thousand dollars more than you've ever made your whole life  do you have a plan for that? The discipline of plenty is the same as the discipline of it's not the same, but it is actually, it's different, because when, when you're broke, being disciplined might be, Hey, look, we can't go out, because we ain't got it. What if you can buy everything you've ever wanted? Should you?  And people don't think that way, but that's a real issue, because you can make a ton of money and, and be more broke than you were when you didn't have anything, if you don't have disciplined habits. Maybe get something from the VA,  and then you go and get a decent job. I had this same discussion with a friend of mine, Okay, you're about to make 100,000 more this year. Have you thought about that? Have you thought about the tax implications of that? Have you thought about what you're going to do with that? Have you thought about how you're going to keep yourself under control? That's something we need to talk about, among even higher ranking people, because it's not how much money you make, it's how much you spend. There's a lot of broke doctors and lawyers running around.

If movie were made about his life, who would play him and what would the name of the movie be and SHOUT OUTS
38:18 – 40:10 Shane Pilgrim Wow. Who would play me? I mean, I would love to be James Bond. Okay. But  an old school James Bond, Sean Connery, or Roger Moore. Roger Moore because he was goofy, but he was the smoothest in my book. So yeah. Roger Moore would play me, young Roger Moore, not old Roger Moore. And really, I think the title of my movie or the soundtrack of my life would be Make Your Own Luck. Luck is where preparation and opportunity meet. If you're prepared and you're open, have you ever read The Alchemist? It's another favorite book of mine. The Alchemist's principle says that the universe is conspiring. Whatever you believe the universe is, so it could be Good or...nature, whatever, to put you in a position, you just have to be ready to accept it and so my whole life, I think things have happened to me for a reason and I've been lucky or fortunate enough, but I've also been prepared and open to opportunity. And that's really made the difference in my success. So, make your own luck, go out and get it. Three people I want to give a shout out to. My wife Crystal, my son Julian, and my mom.

If there was a GIANT BILLBOARD that he could place anywhere in the world with his message on it for the world to see, where would the billboard be and what would the message say?
40:11 – 41:24 Shane Pilgrim I'd put it at Times Square in New York City because I'd want to be on Times Square. Yeah, maybe not. Yeah, I don't want the underwear on me. What would it say? I think my slogan I talked about is really making your own luck. But I think...Something I said at my retirement was, I felt  in my career, I didn't lead with the fact that I was different enough. I was born in the Caribbean. I grew up in the Caribbean until high school in New York and I never really spoke about it a lot because I felt in the military it was better to just kind of conform and fly under the radar. But what I said at my retirement was people should lead with their differences. Because our differences make us a stronger team, and it's almost better for our national security to acknowledge how different we are and then use those strengths to be better as a nation. I'd put lead with your differences.

More about Shane and Outro
41:25 Shane Pilgrim I'm on LinkedIn. Shane Pilgrim, P I L G R I M. I should probably be the only one on there. My company is Kaya Co Consulting, so if you put those things together, love to connect. Or, reach out to me with a question, happy to help anybody that I can, particularly veterans or anyone else , as long as I have the time you can have the benefit of anything I can give you. Yeah, so that's, that's probably the best LinkedIn.

More info about the guest:
LinkedIn: https://www.linkedin.com/in/shane-pilgrim/
NextOp: https://nextopvets.org/

Books and People mentioned: 

• Alexander Hamilton
• Todd Simmons
• Book The Millionaire Next Door
• Book Good To Great
• Book Leadership Secrets of Atilla The Hun
• Admiral McRaven
• Chief Master Sergeant of the Space Force #1, Roger Towberman
• Chief Master Sergeant of the Air Force #18, Kaleth Wright
• The Alchemist
• Family

Quotes: "If you are not networking you are not working"

Key Takeaway: In redefining wealth and success, Shane proposes that true richness lies in the freedom to do what one desires, challenging the conventional definitions. He shares his own journey of changing his mindset on wealth and success, stressing that it's not about the amount of money one has but what it enables one to do.