
Loading summary
Travis
And Doug, there's nowhere I wouldn't go
Podcast Host/Announcer
to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row
Jason Redmond
at a comedy show.
Podcast Host/Announcer
Hey, everyone, check out this guy and his bird. What is this, your first date?
Travis
Oh, no. We help people customize and save on
Podcast Host/Announcer
car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird. Yeah, the bird looks out of your league anyways, Only pay for what you need@libertymutual.com Liberty.
Jason Redmond
Liberty. Liberty. Liberty.
Podcast Host/Announcer
You're listening to the Travis Makes Money podcast presented by GoHighLevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet. Just go to gohighlevel.com travis.
Travis
What's going on, everybody? Welcome back to the Travis Makes Money podcast where it's our mission to help you all make a little bit more money. Today on the show, I have a new friend of mine, Jason Redmond. He's a retired Navy seal, combat wounded warrior, New York Times bestselling author and transformational speaker. Shot in the face during combat operations, he bodies the overcome mindset through his speaking, coaching and advocacy work. He's delivered over 700 keynote presentations now and authored multiple books on leadership and resilience. Jason, what's up, man? Welcome to the show, Travis.
Jason Redmond
Honored to be on, man. Thank you.
Travis
Of course. So I usually start this thing off with more of the entrepreneurial crowd by saying, what was the first dollar that you ever made? That was really exciting. But it seems that you went directly into the military path, following, following like the, you know, high school era. Tell me a little bit about your decision to take that path. Obviously, like Special Forces is something that doesn't, you don't just happen to fall into typically, you know, it's like, comes from a deep desire to serve at the highest level. So tell me a little bit about that decision.
Jason Redmond
Yeah. And, and I can answer both at the same time. I worked, I actually got kicked out of the house when I was 17. So I started working when I was, I think I first job when I was 15, but 16, I was waiting tables. And I'll never forget that moment was I'll never forget when I got my first hundred dollar tip. Oh yeah, that was amazing. Like, man, if I hustle and I do a good job, there's a reward for this. And, and I, and I bought a pair of Oakley razor blade sunglasses. I blew my entire paycheck.
Travis
Hell yeah.
Jason Redmond
And spending. But obviously my path was to go into the military man I came from family, a family of service and special operations had really piqued my interest. And I learned about the SEAL teams, and I just set my sight on that, and that's what I locked onto and followed that path all the way to completion.
Travis
Was it. Was there ever any other options in your mind?
Jason Redmond
Not really. You know, the thing is, I mean, there were other options in the aspect. There are other special operations units. So I did, for a short period of time, I tried to go in the Navy first, and I kind of butted heads with the initial Navy recruiter, which kind of made me steer over to the Army. So I was going to go Ranger, Green Beret. I actually got disqualified because I had ruptured my eardrum when I was a kid. So, you know, first major obstacle, first major adversity, you know, but that didn't stop me. I was like, well, no is always the first is the first obstacle to yes and completion. That's what I always try and tell everybody and my kids. So I started looking at other things, and during that time, new recruiter came in who was like, hey, let's, you know, much more open and much more willing to help me. And he did. And that led me down the path to become a seal. The thing is, in the Navy, there is no other special operations path as opposed to many of the other branches. I mean, the Navy, really, we have the SEALs, we have SWIC, and we have EOD, but for me, SEAL was it. And once I went on that path, if you don't make it, then you're going to be your. Your option when you're. If you don't make it through SEAL training, you get assigned to the regular Navy. And that was not an option for me. I didn't join the Navy to be in the regular Navy.
Travis
Yeah, right, right. Because, I mean, those are two wildly different. Like, it's. It's not. It's not the army, where it's like, okay, I didn't make it to this cut, but I'm also still doing a lot of the same type of work. You know what I mean? It's. It's a wildly different career path at that point. Almost. When you're having those initial conversations with a recruiter, is it. Is it with the intention? Like, are you talking to them about, like, I want to be a Navy seal? Like, and do they help you put you on a path to that, or are they just kind of like, yeah, you and everybody else guy get in the back of the line.
Jason Redmond
There's some of both of that. Although, you know, when I came in. I came in the military in the early 90s, and the seals weren't as prevalent. Definitely a lot not in the spotlight like it is today. And we didn't really have a clear path. Today, it's much different. Our young men that are out there that want to become SEALs, there is a very clear path. There's actually a draft they have to try out, they have to get put into the draft, and then they're selected to go to SEAL training. So very different from when I was younger. Probably much more encouraging because we want the large amount of numbers so that we can, you know, we can funnel it down to really have the top candidates that are going to become seals.
Travis
When you initially started SEAL training, were you optimistic? Were you pessimistic? Were you like, man, this is way more difficult than I thought it was going to be? What was your mindset going into that?
Jason Redmond
No, I knew it was going to be hard. I mean, I came in the Navy, I went through my initial school, or job, if you will, which for me was intelligence specialist. Back when I came in, you had to have a Navy job before they sent you to SEAL training. That way, if you failed out, which 80% do, then you would go to the Navy to fill that job. Yeah, today it's different. Our kids go straight into the pipeline, and then if they don't make it, then they figure that out afterwards. So I went to my initial Navy training, and then I got assigned actually to work at the East Coast SEAL teams before I went to SEAL training. So I had a good understanding of what I was getting myself into. There were guys there who helped, you know, prepare us to get ready for training. So I knew training was going to be really hard, and it was really hard. So there was no real shocks, was there?
Travis
What was the most surprising thing during a SEAL training or SEAL selection or. Not necessarily surprising, but, like, what was the most difficult part for you?
Jason Redmond
I mean, Hell Week is definitely the biggest obstacle for everybody. I mean, hell Week is the part where everybody gets pushed past their breaking point. I often joke that there are people who will tell you I. There are people who will talk about the times that they struggled and thought about quitting like I did, and almost everyone. And then there are the liars, the guys who say, I never once thought about quitting. I mean, training is designed to push everybody over the edge, but that's where you're truly forged. Those are the moments where you truly start to understand who you are, and you break through and you begin to recognize that, hey man, I can push through this pain and adversity and doubt. Keep going.
Travis
It's the, it's the whole extremity, extremity expands capacity notion that you, when you get to an extreme situation that you never thought you'd be able to make it through, you, you expand the capacity by which you now view as the frame of what you are capable of doing, which before might have been limited and now starts to become more unlimited. When you, when you make it through something like that, I would assume when you're, when you're coming on the other side of something like Hell Week, do you feel like a breath of fresh air? Because I know. Because that's not like the end of training, is it?
Jason Redmond
No, it's at the beginning, actually. Yeah, it's, it's within the first. It varies, but it is very much at the beginning of training. You know, I think for me it was the sixth week. I think currently it's the fourth or fifth week.
Travis
Yeah. And so when you're, when you're coming out of that, is it, is it in your mind when, like coming out of Hell Week, I assume there's a high attrition during that time period. When you're coming on the other side of it, do you have like this mental win that's like, okay, I made it through that. If I made it through that, you know, I should be able to make it through the rest of this thing?
Jason Redmond
Yeah, 100%. As a matter of fact, the statistics are in your favor. If you make it through Hell Week, you have a 70% chance of graduating, whereas prior to Hell Week, you only had a 20% chance of graduating. So up here. But we also have an 80% attrition rate during Hell Week. So Hell Week alone is the great weed out. The majority of the class gets cold during Hell Week. So if you make it to the other side, 70% chance of graduation move forward about a month. There's a super hard evolution in dive phase called pool competency test. And that is probably one of the second hardest evolutions in SEAL training. If you make it through that, you now have a 90% chance of graduating. So barring all the little stupid things that can set you back. So they're definitely confidence boosters when you make it through these big benchmarks.
Travis
How many people come into SEAL training do you think anecdotally are relying on like, you know, physical aptitude versus the mindset mental aspect of this? Because from what, from what I understand, from my ignorant perspective, of never having gone through it. It seems to me that, that you, you obviously pulling from the, you know, the best and the brightest of people who know what they're getting into, yet there's still an 80% attrition rate. And it seems like regardless of what type of physical shape that you're in, it just doesn't matter because they're going to push you so much that it, that you can't help but break. In that context, the only thing that can carry you through is some form of mental resiliency. Right.
Jason Redmond
I, I mean, I would. It, it is, yeah. Physical attributes don't. As a matter of fact, the reality is when you check into SEAL training, you'll do your final physical test. And there is no reason, every single person that passes that test, there's no reason why you shouldn't graduate physically. You are capable of doing all a SEAL training. It's just mental. And what, what, what I've definitely seen and I, and the stats will prove it and I mean some of this anecdotally, but I think, guys, I wasn't this natural athlete, man. You know, I was a runt. I'm not a big guy. I'm about 5, 7, 1 70. And I really had to, I had to work hard. Now don't get me wrong, there were some things. I was a good runner, but I wasn't the best swimmer. So, you know, everybody has these challenges. But what I came to find was guys who were naturally gifted athletes and they were star athletes most of the time those were the guys who would end up leaving sooner than others. And I think it was just because they were genetically gifted enough that they didn't have to work as hard as everybody else.
Travis
Yeah, they never experienced that, that like, I'm not good enough before.
Jason Redmond
That's right. And everyone, everyone gets punched in the face with it at SEAL training.
Travis
Yeah, quite literally. Yeah. Okay, so, so how long, how long with your career from, you know, graduating and becoming a SEAL till when you're done?
Jason Redmond
I did 21 years. So I came in in September. I joined while I was still in High School, September 92. And I retired from the Navy in the very end of August of 2013.
Travis
Wow. And so, so tell me now about this, this date in, in 2007, which, I mean, that's crazy. That's like what, 15 years almost to the day that this episode of the
Podcast Host/Announcer
show is brought to you by Chime. Chime is not just another banking app. They unlock smarter banking for everyday people with products like MyPay giving you access to up to $500 of your paycheck anytime and getting paid up to two days early with direct deposit. Some old banks still don't do this. So forget overdraft fees, minimum balance fees, monthly fees. Chime turns everyday spending into real rewards and progress. Plus, they have this new credit card which I'm a big fan of, this Chime card. It's the new way to build credit history with your own money and actually get rewarded every single day. So a lot of cards like this, they require you to put some sort of money down and then they will give you a credit card based on the money that you put down. But when they do that, because it basically is working off of the cash that you have down as collateral for the credit line, you don't get rewards on it. Well, Chime changed the game with their new credit card as well. There's no annual fees, there's no interest, no strings attached. And when you get qualifying direct deposits, you get 1.5% cash back on eligible Chime card purchases. Chime is not just smarter banking. It is the most rewarding way to bank. So join the millions who are already banking and fee free today. My younger self would have benefited from this, and I know you will too. It just takes a few minutes to sign up. Head to chime.com travis that is chime.com travis this episode of the show is brought to you by Factor. Look, everybody who's listening to the show is busy. I get it. There's kids, there's distractions, there's businesses, there's side hustles, there's podcasts, there's everything to prevent you from eating good quality food all the time. So for me, eating healthy isn't necessarily a willpower problem. It's just more of a setup problem. It's just easier to pick the processed food because I know I can just grab it and eat it really quick. Well, enter factor with factor. I'm hitting my nutrition goals this season. Without the planning, the grocery runs or even the cooking, they have meals built around your goals. Whether that's weight loss, overall nutrition, more protein, or GLP1 support for strength and workout recovery. Check out Factor's Muscle Pro collection. Every meal is crafted with functional ingredients. Lean proteins, colorful veggies, whole foods, healthy fats. In fact, they ban 175 plus ingredients. So no artificial colors or sweeteners, no high fructose corn syrup, no refined seed oils, just nutrient dense food. It's fresh, never frozen, and they have over 100 rotating weekly meals including globally inspired flavors like Mediterranean and Asian. Mediterranean is my favorite, so there's always something new to look forward to. Try the newly launched ready to eat salads with vibrant ingredients like elote, corn and miso at home mame. Plus there's over 70 add ons to round out your your nutrition from like all the snacks and stuff that you grab throughout the day, from green juices to, you know, peanut butter, energy bites, things like that. It's ready in two minutes. Factor shops, preps, cooks and delivers straight to your door so you have more time for everything that you love. This spring I use this and you should too. Head over to Factor Meals.com TMM50OFF and use code TMM50OFF to get 50 off. 550 not 1550 off and three daily greens per box with new subscription only while supplies last until September 27, 2026. That's FactorMeals.com TMM50OFF and use code TMM50OFF to get 50% off and free daily greens per box. Factor meals.com TMM50OFF.
Travis
You were in was when this, this attack happened. So, so tell me a little bit about that. Take us back to that, that moment.
Jason Redmond
Yeah. My team and I were, we were operating in the Anbar province, the western province of Iraq, really the heart of the Al Qaeda insurgency was around Fallujah and the Anbar province. And we were going after a senior Al Qaeda leader. Pretty dangerous individual. We'd been tracking most of the deployment and we, that night we went after him. And to make a long story short, he was in a house and his team had set up an ambush line as we were maneuvering up to the house to try and get him. And we walked into a very well executed ambush. Multiple. Myself and multiple members of my team were shot. I was hit eight times by an enemy machine gun between my body and body armor, including a round of the face. So I owe my life to my teammates. I owe my life to The Air Force AC130 gunship that was up overhead. We ended up calling in the closest fire mission in the entire Iraq war. And thankfully we all made it out and started a new journey.
Travis
Wow. All of you made it out. Were you unconscious during this? Like, like, how do you survive getting shot in the face?
Jason Redmond
I was, it knocked me out when it initially hit me and I, and I will say I'm very fortunate. I mean, it didn't hit me forward that probably the outcome would have been a lot worse. All the bullets hit me forward, but I had turned to move to where Our guys were. And the round caught me from behind. It hit me right in front of the ear, traveled through my face, took off my nose, blew out my right cheekbone, it broke my bones above my eye, vaporized my orbital floor, broke the head of my jaw, shattered my jaw to my chin, and just did a lot of damage and obviously knocked me out. So I was out for about what we estimated to be five or 10 minutes, pinned down in front of the guys, and then, you know, came to and, and really recognized that A, I was out of the fight, both physically because I was so messed up, and B, because I was pinned down out front. So I just had to focus on, you know, staying awake to stay alive. I mean, that was kind of a mantra I had while I had to trust my teammates and, and obviously the, the Air Force to, to bring in the air, us out of there.
Travis
How long before they like, how many minutes, you know, elapsed between getting shot, waking up, being like, oh, I don't even know what's going on, Just trying to stay awake here until you're waking up in a surgery center, you know, a few hours later it was, we
Jason Redmond
know that gunfight lasted about 40 minutes. I was hit in the first couple of minutes along with teammates. So, you know, I was pinned down for probably 35 minutes, which is a long time to be shot at by big bullets. But, but you know, we're here, man, and that's, you know, that you can, lots of rabbit holes we can go down. At the end of the day, everyone in life will go through trauma. That's the reality. You don't have to go through the bullets and bombs of battle to experience trauma. I, I survived this vicious enemy ambush, but everybody gets ambushed in life. I mean, that is the premise. And the guy, the, the bottom line of everything that I talk about to people. Everyone gets shot up. You get shot up by injury or illness or loss. You get blown up by rejection and failure. All of us walk through the minefield to depression and despair. The difference is it's a choice to drive through trauma and grow from it. You know, I've taken it and turned it into something that I can help others drive forward and overcome the trauma they've been in their lives. And that really, it became a monumental, life changing moment for me on the battlefield to survive that. It is, it is the baseline of almost everything that I speak on, along with going back a couple years prior where I messed up as a leader. And that really messing up as a leader and growing set me up for Success coming out of that battle. And it's the same thing that I talk to everybody. You were talking about expanding and SEAL training out of your comfort zone. You know, that's the overcome mindset that I speak on. Be thankful for the hardship that you go through, because by navigating successfully through it, it sets you up for greater success and greater adversity in life.
Travis
What kind of a newfound perspective did you gain when you wake up from something like that and realize that you. That you made it, that you survived? Is there like. Is there immediate, just like, gratitude? What. What's the feeling?
Jason Redmond
Yeah, I. I didn't think I was going to survive when I. When I drifted unconscious in the operating room and finally let go, I wasn't sure I was ever going to wake up again. So to come to, I was so elated, you know, and. And granted I hadn't done drugs and suddenly now I'm high on opium. On.
Travis
Yeah, you know, synthetic morphine, I think is what exactly.
Jason Redmond
Yeah, it's a highly potent synthetic morphine. So that stuff works a kite. And euphoric. Because I survived to know that I'd be able to go home and see my wife and kids again. But then the reality set in. I mean, only took a couple of days for. Holy smokes, man. I am super messed up. And the doctors were inundated me with a lot of bad news, how difficult this journey was going to be. And it was. It would take four years and 40 surgeries to go through.
Travis
All surgeries.
Jason Redmond
Yeah, there was just that lot of infection problems and issues. So the bottom line, it gave me tremendous perspective. Most people who come that close to death don't get to come back. So I. I tell people I have a. I have four frameworks that I speak on. Lead always. Which built on the framework of three rules of leadership. Lead yourself, lead others, lead always. The overcome mindset and how we get off the ax from the life ambush as we encounter mission. And mine is built around the sign on the door I had. But the last one is all about making the most of the life you have. Living greatly. It's why I'm so aggressive in my entrepreneurial journey and probably doing a lot more. Many people that say, man, why are you doing as much as you're doing? Well, I don't know. Because I can. Yeah, because I want to. And because I. I don't want to waste this life. The second chance at life that I was given. And I think so many people live their life know it's fueled by fear and doubt. And, you know, the what if? Mindset. What if I fail? What if people make fun of me? What if this doesn't work? You know, they'd rather settle than expand. So all those things have driven me to live as greatly as I possibly can, and I try and encourage others to do the same, because when you. All of us are going to die, that's the reality. You're never going to get away from that. At least probably not in our lifetime. Maybe a couple lifetimes from now. Maybe.
Travis
Yeah, maybe they'll figure something out, but probably not anytime soon. Soon. Yeah.
Jason Redmond
Yeah. So you want to get to the end of your life and you want to look back and go, man, I did it. I don't. I went after everything and. And you'll fail, and that's okay, but at least. At least you'll fail and you'll be like, at least I. I know I went after it. I have the. The victory of achievement and. And understanding why it didn't work and the satisfaction of doing the work and figuring out, instead of, like, the ma. The vast majority of people out there that get to the end of their life and they ask themselves, well, what if. What if I had done this? What if I. Would my life have been different?
Travis
Yeah. The regrets of the dying man. There was a lot of data around the idea that most people regret things that they did not do rather than regret things that they did do.
Jason Redmond
And I'm. I'm living proof. And I say the same thing.
Travis
Yeah. On the entrepreneurial side, tell me a little bit about what the business structure looks like these days. Is it, you know, keynote speaking books? You know, what are some of the sort of monetization points that. With the. With the stuff that you're working on now?
Jason Redmond
So I'm involved in five different businesses, and there's a reason for that. And this is something that other people out there, the entrepreneurs. And I love that you and I talked at the beginning about the fact that so often, so often the mindset is if you want to be successful and make more money, you just need to spend less. Like, it's a mindset of you're limited at this point. So the way we increase the money we have is by spending less. And I hate that mindset. Like, I want a growth mindset. I want to. How do I make more money? And I was speaking, and speaking was doing really well, but I got punched in the face with COVID So my company was on a. We were on a. We were doubling, doubling, doubling every year, and we were projected 2019 was the biggest year we had ever had, and we were projected to double it again to finally break seven figures. And in 2020, Covid happened, and it was my sole revenue source, aside from my retirement income from the military. And if it hadn't been for that retirement income, I would have lost everything. I would have lost my house. I would have lost everything. We had to get really tight, and thankfully, we weren't living crazy outside of our means or anything. But it taught me a lesson, like, you need to. It actually created a framework that I live by now, and I speak at entrepreneurial events about this, and it's a little fun play on words. Like, if you want to truly achieve success on the entrepreneurial path, you got to embrace dei. And people are like, man, aren't you, like, a conservative dude? And I'm like, so what DEI stands for is, number one, you got to diversify your income streams. And that was the first thing I figured out. I was like, dude, speaking, it can all come to a grinding halt. So you need to start looking at how do we diversify? So I started expanding into coaching and other things. But then I kind of came up against rule number two. The E stands for you got to look for ways to earn equity and an exit. Because what I began to realize, man, is in speaking, I can't sell myself.
Travis
That's right.
Jason Redmond
You know, a lot of people out there look at Tony Robbins and the model that he built. But it is, I think, as technology is advancing and as we're all getting inundated with this virtual world we live in, I think it getting more and more and more difficult to duplicate yourself and. And to scale in the manner that Tony Robbins did. It's just, you know, I would try and sell other speakers. I tried to build out a speaker's bureau and all these things to sell other speakers, but they didn't want those other speakers. They wanted me. Yeah. And I was just trading time for money, so there was no exit. I couldn't just sell myself and exit the company. So I started looking at, okay, how do I build equity? And how do I look for exits? So that led us down other paths. So we actually started to put our money to work. That becomes the big thing. So my wife and I got super intentional. We had read the.
Podcast Host/Announcer
This episode of the show is brought to you by Wayfair. It's way day at Wayfair. From April 25th through the 27th, you can score the best deals in home, like, up to 80% off with free shipping on everything. Wayfair makes it easy to find exactly what fits your style and needs, from furniture and decor to home improvement and outdoor essentials. And it's all on sale during Wayday. Best part, everything ships fast and free during Wayday. Plus you can shop with Wayfair Verified, AKA your shortcut to the good stuff. So their team of product specialists vets everything by hand using a 10 point quality inspection so you know that you're actually getting a quality piece no matter what your budget is. Look, I we basically have redecorated our home with Wayfair in the last few months and at every time we use a site I'm always blown away by how easy it is to use the platform itself. Also to find like the craziest stuff. Like if you think for a second that there's something that's not on Wayfair that you could put inside of your home for something, just test me out on this. Go to Wayfair and search for it. I promise you you're going to find it. It's crazy whether regardless of your aesthetic, if it's mid century modern or farmhouse or contemporary or eclectic, or you're looking for outdoor furniture or home upgrades or you want to upgrade the kids room or you need a new shoe rack, whatever it is, Wayfair has it. They make it simple to narrow down to exactly what works for your style and for your budget. Plus they have great reviews, filters, visual tools to help you make sure that it's the right fit and then, you know, installation and assembly could be available depending on what you buy. It makes the process easier. Their shipping always blows my mind because you can get some like a literal Our dining room table that we just got came from Wayfair and they shipped it to our house fast and completely for free. So they have thousands and thousands of five star reviews to help you shop with confidence and find things that fit perfectly into your home and lifestyle. Wayday is the sale to shop the best deals in home. We're talking up to 80% off with fast and free shipping on everything. So head to Wayfair.com April 25th through the 27th to shop Wayday. That's Wayfair.com W-A-Y-F-A-I R.com Wayfair Every style, every Home this episode of the show is brought to you by Shopify. Starting something new isn't just hard, it is terrifying. So much work goes into this thing that you're just not entirely sure that's going to work out and be hard to make that leap of faith. Trust me, I know. When I started this podcast, when I've started several of my businesses, I just wasn't even sure what I was doing. Like, what if nobody listens to the show? What if I make a fool of myself? What if I embarrass myself? Nobody buys my stuff. Now I know that I was right in believing in myself and launching my podcast and several of my businesses, despite all the fears and hesitations. But it also helps when you have an amazing partner like Shopify on your side to help. Shopify is the commerce platform behind millions of businesses around the world. And 10% of all E commerce in the US is using Shopify. Like, this is the place that hosts all of your favorite products and services. So if you are considering this, then Shopify is a must. Especially, especially, especially if you're going to launch some sort of an E. Comm product. So get started with your own design studio. With hundreds of ready to use templates, Shopify helps you build a beautiful online store that actually matches your brand's style. But Travis, what if I get stuck? Well, Shopify is always around to share advice with their award winning 247 customer support, which is very, very important to people like me who are still some for some reason, like caught in the 1980s and I want to talk to somebody when I actually have a problem and instead of just relying on an AI system. And did I mention that the iconic purple shop pay button that's used by millions of businesses around the world, that's from Shopify. It's why Shopify has the best converting checkout on the planet. Helps boost conversions, meaning less carts going abandoned and more sales for you. So it's time to turn those what ifs into with Shopify today. Sign up for your $1 per month trial today at shopify.com TMM go to shopify.com TMM that's shopify.com TMM
Jason Redmond
book rich dad, Poor dad, which really changed my mindset. Turn rich people turn their liabilities into assets. Poor people just look at how do we continue to operate within the existing structure we're in. It's the reduced cost mindset. Yeah. Whereas rich people say, well, how do I leverage my money so that I can make more money? My family, we were big skiers, we love skiing. And every year we would spend anywhere from five to $10,000 on a ski vacation. Well, I realized, man, I'm giving everybody else my money. So we said, let's take speaking money and let's start buying ski condos. You know, and, and obviously I couldn't afford to buy a Vail, you know, slope side ski condo at that time. But we started looking at places where we were going and we just rapidly started purchasing. Today we, and we built a company around that. So I now own six ski condos. Nice. And. Yeah, absolutely, man. And, and so now I'm able to go ski at our ski condos and somebody else paying my mortgage.
Travis
Yeah, that's the nice thing, man, is like you can, you can invest in the things that you actually enjoy and that, you know, there's so much noise about like, what you should do with your money and you should put your money here, you should put your money there. And it's just like, okay, but at the end of the day, if you just get really good at this one thing, regardless of what everybody else is saying, you know what I mean? Then like, it just, you don't have to go buy 185 door apartment complex in order to be able to make your money, make you money. You know, it's like, well, I like skiing. We know these areas. I know that. I know what I pay when I rent Airbnb when I go skiing. Like, you know what I mean? Like, there's going to be demand here. And then you just go deep in that vertical and it, and it can pay dividends and allow you to continue doing the stuff that you love doing. You know?
Jason Redmond
That's right. Yeah. So if you have a need or even a want, how do you turn it into an asset? I mean, and really you could. I've started to look at this with almost anything. I mean, if I wanted to buy a really nice car, I could buy it and then put it on Turo and rent it. Now I'm gonna have to share my car. There's a. But the reality is these are different ways that you can get things you want. So it's a mindset of building equity in something.
Travis
Yeah.
Jason Redmond
And then the exit front, I started looking at that. So that led us to buy. The next thing we needed was a. We needed a new office space. We had outgrown the office space and we had a temporary office space during COVID but they sold that building and we had to move out. So now it's faced with, man, I need an office that I can record videos and then I can do all the things that a influencer and coach needs to do. Well, we started looking and my wife found this beautiful building that was way more than what I thought we could afford. But the more we looked at it we were like man, what if we turn this into co working and like a creative media event center? Because I need an event center and I need recording studios. I need all these things but I don't need them all the time. So that's what we did. We ended up buying this building. So once again taking the existing money and equity we had, putting it to work to buy this so to leverage this asset and now getting other people to pay for it.
Travis
Yeah.
Jason Redmond
So that became our next thing. So our next business. We split that business into two things. One is the building itself. So and the other one is the actual co working and event center and creative center. So we can either sell those together someday for an exit or we can hold onto the building and sell the business later. So once again being creative, the last component is increase income. So dei so the exact opposite of reduced costs. And I mean don't get me wrong, in a business be smart. But at the same time how do we get creative and look for ways to increase our income? And so I'm speaking, we have our short term rentals, we now have our commercial building which is slowly growing and doing well and getting into the profitable territory. But what I realized I still wasn't. This becomes the pivotal question that you have to ask yourself as an entrepreneur is what I'm currently doing taking me ultimately where I really want to go? Because I'll tell you what, the mindset of just saving money within your existing scheme is never going to get you. If you truly want to level up in this life, if you want to go to middle class to upper middle class, to wealthy to high net worth, you've got to change what you're doing is the reality. And I started to recognize that the current things that I was doing, real estate could potentially get me there. But I needed a lot of capital to do it. So I started looking at how do I invest in up and coming companies that one, going back to one diversifies me, two has equity and three, now I have the potential to exit something that can scale. So I invested in a, in a Whiskey Seltzer company that we're growing that so that's kind of the next mo. Patriot Hard Seltzer is our Whiskey Seltzer company. We're in New Jersey, we're in Texas and we're, we're getting ready to launch into Virginia. And then I am a founding member of a new technology company we're trying to revolution called turbovets. So we're trying to revolutionize how we deliver our active Duty, service member benefits and as they transition over into veteran, all through a high level, AI automation driven platform. So these are the things that I've done. Embrace dei, diversify your income streams. Number one, get a good strong income stream. And once you got that machine running pretty well, take that money and start to invest in others. Figure out how you diversify or figure out. You know, speaking for me is the most powerful thing I have. So that's my cash cow and I'm taking that and I invest that into other things. Number two, diversify. Or number two, look for things that have equity and exit. So real estate is a good, good one. Turn your liabilities into assets because they both have equity and you have the ability to exit them. You can sell them off at some point if you need. Look for companies that can do the same, that you can scale equity and exit. And then the last one, look for how you increase your income. I want to make more money.
Travis
Yeah, you and me both, Jason. I think everybody listens to this show. I think is probably in the same boat. One, one last quick question for you, if you'll allow it. What's a skill set that you had to gain from on the entrepreneurial side that you didn't necessarily need to have in the military? Was there something that was like I have to learn how to do this thing that I have not ever really had to learn before?
Jason Redmond
Oh man. Probably the biggest thing. I don't want to say you don't have to sell yourself in the military. And I, and I still lean this way. I'm not a big fan of very colorful flamboyant sales techniques.
Travis
Sure.
Jason Redmond
Which is pretty common in the business world. There's nothing wrong with that. But there's a lot of times where colorful flamboyant sales techniques are borderline high level exaggeration and sometimes.
Travis
Absolutely.
Jason Redmond
And, and I am not a fan of that. But there is a balance there. You have to sell your product and what you're doing and then you have to deliver on it. And, and, and you have to put yourself out there. You have to build a brand. So all those things were things that I had to do that the military. You don't do. You don't do that in the military. You, you, you sell yourself on your capabilities that you want and you would never over exaggerate what you're able to do. Whereas oftentimes in business, at least on a lower level, you should exaggerate a little bit and then push your business to reach that point. You need to deliver on it. Yeah, you know, don't over promise and under deliver, but that's something I've had to get out of my comfort zone in the, in the business world to embrace and understand.
Travis
Love it, man. That was, that was if, if I, if I were going to guess what your answer was, I felt like that was what it was going to be. Something about sales or like putting yourself out there or something because it seems like it's like wildly the opposite in the military. So. Jason, I appreciate you coming on the show, man. I know you're a really busy guy. Do not take your time lightly. Where can people go to get more from you?
Jason Redmond
Yeah, you guys can find me@jasonredmond.com that's my main website for speaking. I am blessed to be able to get out there and share my message. You can find me on the socials. Jason Redmond, WW is my social profile for all of them out there. You can find us at patriot hard seltzer patriotselser.com and if you are a service member or veteran, we are turbovets.com and we are coming. We are coming.
Travis
So, Jason, love it, dude. Thanks so much for taking the time. Everybody else listening, remember, money only solves your money problems, but it's easier to solve the rest of your problems when you got money in the bank. So let's solve that one first here on the Travis Makes Money podcast. Thanks for tuning in. Catch you guys next time. Peace.
Date: April 8, 2026
Host: Travis Chappell
Guest: Jason Redman – Retired Navy SEAL, combat-wounded warrior, bestselling author, and transformational speaker
This episode features an inspiring conversation between Travis Chappell and Jason Redman, who recounts his extraordinary journey from adversity in the SEALs and surviving a life-changing ambush in Iraq to building a multi-faceted entrepreneurial life. Redman discusses how hardship forged his “overcome mindset” and how he now channels those lessons into business, wealth creation, and helping others turn trauma into growth and advantage. The discussion covers leadership, resilience, multiple income streams, asset building, and how to translate military grit into civilian and entrepreneurial success.
First Exciting Dollar / Early Ambition (01:46)
Choosing the SEAL Path (02:23)
SEAL Training – Mindset Over Muscles (05:15–11:04)
Iraq Ambush and Survival (15:23–19:43)
Immediate Aftermath & Life Perspective (19:43–22:39)
Building a Business After Combat (23:07–26:12)
Investing in Interests & Asset-Building (30:34–33:54)
Scaling Up and Seeking Exits (33:55–37:02)
Most Challenging Entrepreneurial Skill (37:02–38:36)
Resources and Where to Find Jason (38:55)
On Resilience:
“No is always the first obstacle to yes and completion.” – Jason Redman (03:10)
On Facing Adversity:
“Training is designed to push everybody over the edge, but that’s where you’re truly forged.” – Jason Redman (06:35)
On Trauma:
“Everybody gets ambushed in life... the difference is it’s a choice to drive through trauma and grow from it.” – Jason Redman (18:22)
Living Life Fully:
“You want to get to the end of your life and you want to look back and go, man, I did it. I went after everything... at least you’ll have the satisfaction of doing the work and figuring out, instead of... what if I had done this?” – Jason Redman (22:08)
On Wealth Building:
“I want a growth mindset... how do I make more money?” – Jason Redman (23:17)
“If you want to truly achieve success on the entrepreneurial path, you gotta embrace DEI: diversify your income streams, earn equity and an exit, increase your income.” – Jason Redman (26:00 approx.)
Advice to Entrepreneurs:
“The mindset of just saving money within your existing scheme is never going to get you. If you truly want to level up in this life... change what you’re doing.” – Jason Redman (35:09)
| Timestamp | Segment | |---|---| | 01:14 | Jason’s background, early work experiences, and decision to join the military | | 03:10 | Overcoming adversity getting into Special Operations | | 06:18 | SEAL training, mindset vs. physical ability | | 15:23 | Iraq ambush: being shot, survival, and the aftermath | | 18:22 | Turning trauma into a message and mindset | | 23:07 | The failure of a single income stream, COVID, and entrepreneurial pivots | | 26:00 | The DEI framework for success and risk diversification | | 30:34 | Asset-building through ski condos and workspace innovation | | 35:09 | Growth vs. scarcity mindset in personal finance and business | | 37:24 | The challenge of self-promotion and sales as a veteran entrepreneur | | 38:55 | Where to find Jason & current projects |
For more practical wisdom from real money-makers, subscribe to Travis Makes Money and connect with Jason Redman at jasonredman.com.