Are you ready to learn the secret to success? Join us today as Kyle Depiesse reveals why you shouldn’t sacrifice your personal life for professional success and practical ideas to thrive at home and in the marketplace. Stay tuned to learn about fortune, success, and family!

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Why it’s beneficial to try out new activities
The powerful benefits of mastermind groups and mentors
A more satisfying kind of richness in life
What happens when you step out of your comfort zone
2 qualities you need to develop to overcome life’s challenges


Kyle Depiesse is a husband, father, and entrepreneur. After spending 13 years climbing the proverbial ladder in Corporate America, he decided to leave that pursuit behind and chase another path that was more fulfilling to him. He is the Founder of Guys Trip, taking others on bucket-list adventures and helping them find community. Kyle has been married to his wife, Lois, for almost 10 years, and together, they have a 5-year-old son, Cal. They split time between Grand Forks, ND, and the Northwoods of MN.


Website: Guys Trip
Podcast: Reaching Beyond | Apple  Spotify


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Full Transcript
Kyle Depiesse  00:00
You have to be really careful who you’re listening to, especially in times of fear. And you have to understand what’s my investment, objective and philosophy. And let’s make an agreement in good times what we’re going to do in bad times. So when bad times happen, we aren’t afraid of it. We’ve already agreed to our philosophy and we know our objectives. Welcome
Greg Lyons  00:17
to the passive income brothers podcast.
Tim Lyons  00:20
Here we take the fear out of real estate investing using real life stories of everyday successful investors. Let’s go. Welcome to another episode of the passive income brothers podcast. My name is Tim Lyons and today I’m joined by two rockstars. Like I say every week, but we keep on getting better and better guests. But one of which is my brother, Greg, what’s going on today, Greg?
Greg Lyons  00:39
Well, no upgrade here, Tim, sorry about that. But we definitely upgraded the other guests. We just got back from multifamily mastery five in Orlando, great conference put on by Jake and Gino. And I think some of the biggest takeaways, you always learn the nuts and bolts of real estate and you meet a lot of people. But Tim, I think it’s the sometimes it’s the mindset, and the motivation that you get out of conferences, that fires me up so much, right. And I think I took it out on my kids. I’ve been fired up since I got home. The last two days, I’ve been on fire around here. So I think as we bring Kyle on, I think it’s really interesting his story. And I think we’re always trying to find our way through life. And this is a great story of that constant journey that we’re always on dude
Tim Lyons  01:25
100%. And so if anybody’s out there is listening, and you’ve ever gone to a conference, right? You are all fired up during the conference, you’re all jazzed up, everything’s great, you come out of that you can basically fly the plane home, that’s how good you feel. And then you get home into your everyday life. And if you got kids, you got kids stuff, if you got a spouse, you got spouse stuff, if you got a messy apartment, or messy house, or whatever the case might be you’re back in your own world. And it’s hard to sometimes bottle up that motivation, bottle up that experience and kind of drip it out as needed. Right. So this is where I think it’s really powerful to have somebody like Kyle coming on the podcast, because as you hear his story and his journey, it’s not unlike any of our journeys, right. I mean, you can really feel the resignation of his resignation a word I think it is. But you can feel it right, Greg? So
Greg Lyons  02:21
Well, Tim, we may have to edit that part out maybe not your mastery of the English language is unbelievable. But I think with you and I, we have each other to lean on. A lot of the times, if you’re flying high, I might be low. But we’re able to bounce off our motivation together as we’re building cityside capital. Not everyone has that partner to go through their business journey or their life journey with and you know, people turn to podcasts. And you should always turn to this podcast for a variety of stuff, including the English language. But without that, you know, you have to find your motivation in different places, podcasts, conferences and business partners. So sorry, I’ll stop talking to thank
Tim Lyons  03:03
God. So with that I want to bring in I want to bring in Kyle deputy. Yes. How you doing, Kyle?
Kyle Depiesse  03:10
I’m good. You know, I’ve got two brothers, one older brother, one younger brother, and just a few minutes with you guys just jamming on each other just reminds me of my brothers. So I think you guys got something really cool going here together. It’s a fun energy. And I’m excited to be a part of it today. So thanks for having me on. Yeah,
Tim Lyons  03:28
man. So we got to know Kyle, we are part of a mastermind group. As an entrepreneur, sometimes it can be incredibly lonely out there, right? Because no one exactly knows what you’re going through on a day to day basis. And then you’re out with your everyday friends and talking about other stuff. And you’re like, man, like you just don’t get me. But when you’re part of a mastermind. There’s something in there that when you’re sitting in a room, whether it’s virtual or in person and everybody’s rowing in the same direction, everyone kind of gets each other. We’re leaning on each other. We’re adding value, we’re taking notes. There’s something powerful. So we got to know Kyle on a call that we had a couple of weeks ago, and Kyle story ran right through me like a freight train. And I literally ended up in tears on the podcast call because his story spoke to me it hit me at the right time I needed to hear it I needed to hear the message. So there’s something really powerful about that. So I want to invite Kyle just to kind of tell the listeners a little bit about your story, your core story, what brought you to where you are today, and then we can dive into it? Sure.
Kyle Depiesse  04:33
So I’ve been married for almost 10 years. My wife’s name is Lois. And she is got to be the youngest woman with the name lowest that you will know because everyone whose name is lowest is not from this generation. It’s a generation or two older. So we’ve been married almost 10 years. We have a five and a half year old. His name is Cal Callahan for short. And my background professionally speaking is I started out in tribal wholesale in Southeast Wisconsin amo Wisconsin. I’ve got a packer shirt on I’m a pack khalfan Despite our recent struggles, I’m sticking with them. But I’ve traveled wholesale and then I moved to Minneapolis 2005. I worked in Target merchandising kept working my way up the corporate ladder, right like maybe your some of your listeners are in debt and they’re grinding away. They’re trying to move up that ladder and get a bigger title, a bigger paycheck and all the things right. And I moved on from them. I got into Carlson rezidor Hotel Group, they own Radisson Hotel and Country Inn and Suites. And I had a great job I was traveling I had a portfolio of hotels that I was responsible for. So I had a Aruba I had St. Maarten, they were in there. And I love traveling. Traveling is a big part of my life. I love the travel does for me, the perspective that it brings. For me, I got married then. And I was just traveling probably a bit too much. I wanted to be a husband who was there, I do want to be gone all the time. And so I left the hospitality world, I went into video game distribution, which is kind of funny because I don’t play video games. I haven’t in decades, even when I was younger, I didn’t really play them. And then I found myself really burned out in about 2015. And I was burned out because I was climbing the corporate ladder, I had my eyes on what I defined as successful, which was a very self centered version of that word success, titles, the paycheck what it would allow me to buy what people thought about me the car was dry all this stuff, right? I was really lost in that. And then when I achieved that, I looked around and I was like, Dude, this is not what I thought it was going to be. This is not who I want to be. I’m so focused on work. Maybe it’s the ALC non alcoholic and these workaholic is the word for it. Although I will say that a lot of times coming home from work like I just be so tired, so burned out. So last so confused, I would just turn into some escapism behaviors and end up grabbing you know, what would be one beer turned into three, or maybe it’s one glass of bourbon turned into more. And I was doing that more often than not, I’m like, wait a minute, I’m confused. Like, this is what I thought I wanted to be when I grew up, successful, good title, all these things. And it was the exact opposite. I was really lonely. And so I left the corporate world, I like to say that I retired from the corporate world. And I kind of went through this process of saying, Alright, I’m gonna look back on my 13 years of corporate America career, what did I love doing? Like, what are the dots here? How do I connect the dots. And I found out that I love to uncover the process of learning for people. I’m a teacher at heart. And so I took the pendulum and I swung it all the way back over left corporate America and became a high school business teacher. I did that for two years. And then my wife, Lois, and I had our son, March of 2017. And my wife took her three month maternity leave, that puts us perfectly with when the school year ended. And my wife and I decided that I would take the promotion, the best promotion ever to a stay at home dad. And so June of 2017, I was a stay at home dad, which is a beautiful gift right of spending time with your child. But the other gift came in a form that I just wasn’t really prepared for. And it’s a gift that I’m eternally grateful for. And that gift was much like the wall behind us here, just a white canvas, a blank page. And I said to myself, What do I want to create in this world. And through a lot of failures, through a lot of just taking action, even when I’m afraid a lot of learning, I came to what you mentioned before is this lifestyle brand called guys trip where I just help driven men connect, have fun and learn. And we do that through taking bucket list adventures and trips together. So that’s the long and the short of it. And I’ll let you kind of pick away at whatever you’d like to from there.
Greg Lyons  08:45
Now that’s a you know, so funny when we can encapsulate our lives in like four minutes, right? You just packed like 20 years, your life into like four minutes. But the main thing I want to take out of there is with you being a Packers fan this year that both the Giants and the Jets beat the Packers in consecutive weeks. Yeah. So that’s the only thing I got out of your story. We’re in unfamiliar uncharted territory. I’ll
Kyle Depiesse  09:12
tell you that. True.
Greg Lyons  09:13
But maybe I got a couple other things out of your story. But no, it’s we all have that crisis in life of No, sometimes it’s not a crisis. Sometimes it’s been life crisis sometimes mind hit a little bit early. I mean, I’m a recovering college basketball coach. And when we had my son we had the boy it was I wanted to do something a little bit different. Right. And I probably had to midlife crisis in my life. Because right before we started cityside capital, I was searching for that next thing and Tim and I got together and started raising money for apartment buildings. And that was my thing that really gave me energy and like a lot of our listeners are climbing that corporate ladder, right? They haven’t taken the dive into either becoming a pet passive or active investor? And sometimes like you did, you found out your ladder was up against the wrong building. And when you find that we don’t always have the courage to go back to that blank canvas like you did. And we’ve had a lot of great experiences High School Business teacher and stay at home dad probably have to rank up at the two top things. I mean, I think that’s awesome to make that kind of career pivot. But you mentioned, you know, kind of pivoting towards guys trip is trip is an outstanding business learning opportunity. And I think you could really help people with your business. Can you dive in a little bit and tell us what guys trip is? And really how you become that teacher with your new business?
Kyle Depiesse  10:49
Yeah, so my background in corporate America was in leadership positions. And when you’re in corporate America, you get sent to a lot of leadership conferences, I took an interest in personal growth and development. So I voluntarily went to John Maxwell conferences in Orlando, Florida as well. And there’s nothing wrong with this style of learning. But being a teacher and going back and getting a degree in education, people learn differently, right? Like not everyone learns from just sitting in a crowd and watching and listening to a guest speaker. And so I found myself to be the guy who would go to these conferences, there’s hundreds or 1000s of people. I mean, you guys know what it’s like, you have a lanyard with your nametag on it. And it’s a round table with seven other people there and you don’t know anyone, but you’ve got the pen, the Marriott conference center pen with a pad of paper in your life too. And I just like I want to gouge my eyes out, like I am not learning from 8am to 6pm guest speaker after guest speaker after guest speaker. So I was a guy who would strategically sit by the exit doors of the conference room, because there’s four concrete walls, there’s no windows. And I would say forget this man, like, I’m gonna go surfing, I’m gonna go hiking, I’m going to golf, I’m gonna do whatever it is that there is the adventure is in that area. Because when I get my body moving, when I get outside of my routine, when I’m doing something for the first time, like there is a flood of learnings that come into my little brain. And I’m like, wow, like, what can I learn about surfing in this environment that I can take to my business. And these lessons come at you and just waves pun intended. So I was like, There’s got to be other people that do this. And so I had said, when I was staying home with Cal, I was like, You know what, this is 2019. I’m just going to create this 48 hour container. And I’m going to invite people into my network who are like, Man, I’m just grinding away, I’m working hard, I’m lacking in creativity. Because when you get good ideas sitting in front of your laptop, like how often do those creative I you know, it doesn’t really happen. So like, here’s what I’ll do, I’m gonna curate 48 hours, I got a personal chef that’ll come in, I got really good champagne, I’m going to land a helicopter at the resort. It’s never been done, we’re gonna go up, we’re gonna hover over some waterfalls. Trust me on this. And what was odd you guys is that all dudes showed up to that trip that very first trip, I never marketed it to be all guys. But what was really odd, so I’m an accidental entrepreneur. But it was really obvious to me, based on those conversations that happen there. Guys don’t have a good outlet to just talk about like, Man, I’m struggling with this. Or hey, like, I’ve got this going on in my personal life. Do you guys going through that too? Like, how are you getting through that. And if I can do a good job, any problem or challenge that anyone brings into my group can be solved in that room, or one connection away. And that’s the beauty of bringing like minded people together with diverse backgrounds, industries and interests, we can problem solve together. And as men a lot of times, like I put my head down, I’m gonna do me You do you? Nope, we break through that wall vulnerability really quick, I got some fun ways to do it. And these guys like the ethos of the group is I want to see you win just as much. And I’ll be just as enthusiastic as seeing myself win, and I want you to win, I’m going to help. And so that’s kind of the beauty of it. That’s the genesis of it. I never intended it to be all guys, but I was like, You know what, I’ll just keep doing what I think is the next right step. The path will be revealed to me and so it turned into guys true.
Tim Lyons  14:37
Well, I’m about to start doing some push ups in the aisle, if anybody else wants to join me, because that fills up My Cup. You know, Greg, I mean, you know my story, Greg, I mean, the listeners sort of know my story, you know, 17 and a half years in the New York City Fire Department nine years as a ER nurse, per diem and stuff like that. I wasn’t an entrepreneur, I was punching the clock, but I felt like I was running in place right so Let go the hospital started to decide capital. I didn’t know what I was doing. I just kept on doing right, some purposeful, daily practices. And I built, you know, Business with Greg. And we’ve had some measure of success early on. But I felt like I was very alone in the process, right. I felt like maybe a lot of the people in the firehouse couldn’t understand what I was doing, because not taking anything away from them. But I was just in a different place, building a business building a dream, you know, didn’t really know what the next step was. But I was taking it anyway. And I thank God I had Greg with me, right, my brother, but early on, Kyle, I don’t know if you know this, but Greg and I are really cheap. All right. And I think we’re getting better. I think we’re growing. All right. I think we’re taking some massive action towards not being
Greg Lyons  15:43
cheap. We have a company, we have a company credit card now. A company credit card now,
Tim Lyons  15:50
for a few months,
Greg Lyons  15:51
it has $100 limit, but nonetheless, we have
Tim Lyons  15:56
so when we heard about mentors and coaches and people like our podcasts are spending 100 grand a year on coaches 100 grand a year on mentorship, and Masterminds, Greg and I would talk I call each other be like, Dude, did you hear that podcast? And they’re spending like six figures in coaching per year. Like, that’s crazy, whatever do that, like, that’s loser. You know, meanwhile, like, we weren’t even open to the idea of how powerful that could be right? So fast forward, I get coaching Greg’s like, Dude, what are you doing that he’s like, Alright, cool. I get coaching again. And he’s like, Dude, what are you doing? And he’s like, Alright, cool. So then fast forward, we went to this conference this weekend, and I went ahead and I bought VIP tickets. Now, I hope everybody can see Greg on YouTube, just go check out his face. But, you know, I told Greg, I was buying tickets, but I went ahead and bought the VIP tickets. And, you know, I’ll save you the drama about when you’re in the room with the folks that are rowing in the same direction. And the people that can be one connection away, one phone call away, one deal away, or problem solving, right? And like really making it happen, like Dude, it was palpable. Like we were in the right room. And as we’re having, you know, we’re saying our goodbyes in Orlando this past weekend. And Greg and I both sides of each other almost same time. Like, I don’t know that I could ever go to a conference again, without going VIP.
Greg Lyons  17:19
That actually came out of my mouth. Yeah, we met him his mouth,
Kyle Depiesse  17:23
you’re investing in proximity, I think like intimate proximity. And that’s like to go back to a video game reference. That’s like the cheat code. I mean, it is you’re truly getting the shortcut. You don’t have to. But I do think that a shortcut can be a really good investment. Because you might, it’s hard to quantify because that shortcut that proximity, that thing that you learned from this person, it might have saved you a big failure, and what would a failure have cost in your world in real estate investing? Like it can cost a lot of money, right? Anyone who’s investing, whether it’s a business or in real estate, or whatever, shortcuts can save you money? And it’s hard to quantify that.
Greg Lyons  18:01
That’s what the VIP ticket is. That’s what guys trip is. And that’s what masterminds are. They’re the cheat codes. And you just get to skip so many steps, because you’re learning from the best.
Tim Lyons  18:14
The best quote I heard was, you’re collapsing decades into days. Right? And that might be an exaggeration, right. But I mean, it’s true. That certainly helped Greg, and I do what we did in such a short amount of time, kind of, I want to make a pivot real quick, because this is called the passive income brothers podcast. And we do talk a lot about real estate and passive income here and everything. You know, what’s so fascinating to me is that your story is literally the same exact blueprint as so many real estate entrepreneurs that we have heard, right? The old adage of, you know, go to school, get good grades, get a good job, climb the corporate ladder, work hard, put in the hours, get the promotion, get the title. And I think we all have this like idea of success in our heads. And I don’t know what it is the way that we’re kind of, I don’t know how you were brought up, but we’re still kind of doing the same kind of thing. And to me, early on success was a nice car, nice house, sitting on a beach, you know, drinking a Mai Tai or something like that, right. And what we learn as we get a little older is that it’s the journey, and it’s not the destination. And it’s, you know, I just heard a great podcast on end my left this week. And the three questions that Brendon Burchard asks himself every day was, did I live? Did I love and did I matter? And when you look at life, through that lens through that frame, right, it changes everything, right? And I think that’s the epiphany a lot of real estate investors have is look, I’m doing this thing where I’m climbing the corporate ladder, I got my ladder against the wrong building, I need to either build my own ladder or put it against a different building. So can you kind of just like, you know, take us through that little journey. Right. And maybe just comment on what I just talked about?
Kyle Depiesse  19:52
Well, I think my instance, I don’t know enough about yours, but I’m going to assume it’s similar. I got to this point where I had to ask myself, do I want to keep doing what I’m doing? Or do I want to do something different? Like, you know, it’s an aha moment? And it’s one of those things where, okay, I’m in corporate America for, you know, 13 ish years at this point, I’m in my mid 30s. Do I want to continue to do that? Because I know what that’s been like. And I know the trade offs and sacrifices that I had to make in order to get where I got like, do I want to keep doing that? And the answer was no. And maybe it was for you too, because I just can’t see myself doing this anymore. And then I said, Well, okay, well, listen, we look at entrepreneurship, what’s the worst that could happen? Well, I could just go back into corporate America and get a job. And then it’s like, holy crap, I’m living my worst case scenario. And so anyone who’s listening is like, what’s the worst that could happen? Plan out pencil out, you know, the next couple years or 10 years? And what would that life look like for you? Okay, now, real estate investing is the vehicle right to get you there? But what’s the worst that could happen? Like, what if it doesn’t work? What if you take a swing? What if you take a lot of swings, and it doesn’t work, you’re gonna end up back where you are. So really, you’re living the worst case scenario? So why don’t you do something different? And I think to me, you know, I just kind of hit that moment. And it was like, why not? Like, why don’t we do it, but you have to kind of drive the truck back a little bit, my wife and I have done a really good job with our finances. So we built a little bit of a runway. So you might be listening to this, and you’re like, Okay, Kyle, I get it, I’m gonna quit tomorrow, I would encourage you not to do that, I would encourage you to build a plan. And that might take a little bit, but you’ve got a runway, you’ve got a little bit of support. And then you don’t have to operate out of this massive sense of like scarcity. And if I don’t do something today, like there’s no food on the table, like, let’s be smart about it, let’s build a plan. Let’s save up some money. And then let’s go do it. And maybe that’s your story, too. But my overall comments on that were just, I had this aha moment, I wasn’t gonna keep doing what I was doing for 13 years, I’m not going to keep doing it. What’s the worst that could happen? That was the moment that got me moving in this direction?
Greg Lyons  22:06
Yeah, you know, we help our investors kind of build that runway along the way, investing in multifamily self storage, you know, stop building up that monthly or quarterly income and do a deal or two and have some of the whole thing. So we totally get that. But what’s interesting for you, and maybe for others out there is you went from the title and have any of VP of whatever, to stay at home dad. And that is really hard for some men in particular, to kind of come to grips with because I think you stayed home for like, first five years or whatever. And when you go to the cocktail party, you go to the wherever, inevitably, it always comes up, hey, what do you do? What do you do for it? And I’m not the VP over at Target anymore on the stay at home dad? And that is hard. So can you kind of walk through, you know, kinda how that affected you and how that brought you to guys trip? And how that caused you to kind of look inside and say, you know, how do I take my situation? And keep building?
Kyle Depiesse  23:16
Yeah, and you mentioned it, you get into a situation where you don’t know someone and in America, like, that’s what we do, like when the first few questions is what do you do for work? So, you know, I’m a stay at home dad, y’all can picture this scenario. I’m at a party and the guys end up just kind of congregating. You know, and yeah, you know, the question gets to me, and it’s like, Hey, Kyle, so what do you do when it’s like, oh, gosh, like, you know, here we go, I’m gonna get one of two responses. One is, oh, man, that’s really cool. Like, I wish I could spend more time with my kids. And then the other response, which is overwhelmingly what most people would do is they get incredibly awkward, and the whole energy gets really awkward. And then they try to move on from me and or that topic really, really quick. So that forced me into this space of thinking about why do I get that way? Like? What does it mean to be rich in life? To me, I define that as I’m rich in my relationships, family, son, wife, friends, business partners, I’m rich in moments and memories and experiences. And if I look at like the balance sheet of my life, we should put a lot of weight to that. But unfortunately, in culture in society, the weight goes towards money, titles, all those things, and I don’t disagree. That’s important, like money is a tool that is all a tool to get you different things, but it’s not everything. And so for me, I’ve been putting so much weight on that my identity was wrapped up in my work. I think a lot of guys probably go through that that’s where the ego comes in. So there had to be some sort of a death of my ego and an execution of the ego in order for this other beautiful version of what is a rich life look like to actually come through and so that’s, that’s what it was like, I wish I can tell you, Greg, like it happened overnight, but it certainly did not. And I also had to take a step back and look like I’m holding these trips for people. And these guys who are crushing it at work are telling me and confiding me, like, Hey, man, I put work in front of being a good dad for a decade or a decade and a half. And I am embarrassed about that. I can’t change that now. But I can change the future. And I was like, cool, I’ve got this opportunity with this infant and toddler at home where I get to pour so much into him. So many seeds get sewn into him. And that is just a beautiful thing. So I’m kind of seeing like, both sides of this thing, I get to have guys that around me super successful, confide in telling me like, Hey, I’m struggling, like being a father and the husband I want to be. But then I’m in the social environments, and most people don’t seem to care about it, like externally. So like, this is kind of strange. So I just had this beautiful, different perspective, I think, than most people had.
Tim Lyons  25:55
You know, I love that. I just love that because I’m actually going to segue right into your last podcast. And I just wasn’t to it yet, the day or today, I can’t remember when I listened to it. But you said you’re on a golf course with a couple of guys that are in Pinehurst, North Carolina, and they were super successful. You know, the guy had a balance sheet with a bunch of zeros on and, and it given today’s fear and uncertainty and everything else out there, the conversation naturally went towards economics and the economy and real estate. And you mentioned that, like, you know, you felt like you couldn’t contribute, or you couldn’t contribute on that level. And like, you know, wondering, like, Am I good enough? Am I qualified enough? And I think a lot of us have that. I know that I have that, right? I mean, for the longest time, I’m Tim, the firefighter Tim, the ER nurse now I’m Tim, the private equity guy, like they’re just like, it’s kind of crazy how that happens, right? And like, you know, am I uniquely qualified to help people and investing and support them on their journey, and you can fight it in the guy playing golf on the golf course, hey, you know, you told them what you were feeling. And the guy said something to you, like, Dude, you have totally changed my life and what you’re doing the guy’s trip and everything. And like, you kind of had to hear that, right? You know, for the ego and stuff like that. So I just love hearing that. Because to bring it back to investing in the passive income brothers, right? Like, sometimes, like we don’t know, out there, like, what’s the right thing to do? Who should I call? Who should I surround myself with? Am I rolling in the right direction, like, you know, and I think guys trip is amazing. So I want to be mindful of your time. And maybe you could just share with us one cool trip that you’ve done with guys trip. So just give everybody a little bit of a flavor out there of what they could maybe expect? Because I know there’s gonna be people out there who want to reach out to you after we have this show.
Kyle Depiesse  27:41
You know, this was the toughest question I get asked, because I have yet to we’ve done over 10 of them. I’ve yet to repeat a single trip. And every trip is unique because of what we do. But every trip is unique because of who is there. And it’s hard because each group tends to take on this own personality. But man, like from a pure activity standpoint? Well, gosh, I’m a golfer, so I only use the Pinehurst one, but I’ll go a different route. We went dogsledding in the Boundary Waters of Minnesota and Canada in 2020. And it was cool, because I never like I didn’t think that was a thing. Like I heard of the idea rod, and I heard you know, in Alaska, and that’s cool. Like you can do, but you can really ride behind the sled dogs. And that’s the thing. You know, we did a woodfired sauna, we chained sod into the ice to do the polar plunging. And it was just raw man, it was just out in nature. And there’s something I think for guys to return to like a sense of like, there’s a little bit of discomfort there. It’s cold outside. You got to toughen up, man. Like there’s something to that, that is just kind of fun. And just guys being guys drinking bourbon over a campfire outside. And so I think, and maybe that’s because it’s my personality. You see me in a really short beard right now. But usually my wife gives me the permission to grow my beard out in the winter. And winter starts like November for us and it ends in April. So I get a pretty good beard going. But I love like all things outdoors, all things adventure, being in nature. So I would probably say dog sledding. But honestly, every trip has been so unique. Every trip is so different because the guys show up with an open mind and open heart. And they’re willing to allow me to curate a container where they don’t even know what we’re doing sometimes. And there is one element every single trip where I am curating something that no one in the group has ever done before. Because as men, we can stop peacocking and say, Hey, look at how good I am at this. No, you’re not mad like no one’s good at it. You’ve never done it before. So we’re all going to look like idiots. So let’s just get over that right away so that we can just move on and start making meaningful relationships. So it’s a tough one, but from an activity standpoint, man, I love the dog sledding, dude,
Greg Lyons  29:59
I love that. Well, you know, Tim in the spirit of an open mind, Kyle, I personally think I would have thrived a little bit better at the golf outing, rather than the dog sledding outing. I’m just throwing it out there. And for the people that know me, they’re all shaking their head. Yes. They’re all laughing or they’re driving their car off the road. laughing so hard. So anyway,
Kyle Depiesse  30:19
are you a golfer? Give me the thing behind this here. Well, no, I
Greg Lyons  30:22
can play golf at all. I mean, I do play golf. I’m not very good. Yeah, I wouldn’t call myself a dog whisperer. Okay, so you know, okay, come on, knock
Tim Lyons  30:34
my house, you can barely come in my house with my 30 pound dog. So dog
Greg Lyons  30:38
whispering and sleeping outside. It’s just it’s just, I don’t know, maybe I need a guy’s trip. Hey,
Kyle Depiesse  30:44
it’s all about that’s the thing. Like, it’s all about getting out of your comfort zone. I think it’s cliche to say like, Oh, you got to growth happens outside your comfort zone. Okay, dude, let’s see you show up, then, like, let’s see you put your money where your mouth is? Yeah, it might be a little bit of a discomfort. But that’s where the magic is, man. And so if you can curate that for people invite them to step in, and they trust you that you’re going to put together something that’s pretty cool. Pure magic happens in every single trip, there’s been an unexpected ounce of magic. I can’t even explain how it happened. What happened, but when people show up and are like, Alright, man kind of surrendering to this. Let’s go. It’s beautiful, man. It’s really cool. That’s
Tim Lyons  31:25
awesome. Kyle, at the time that this time, I kind of want to trudge through the last three questions, so we can be mindful of your time. The first one, I really am interested to hear this, from your perspective, you have shared with us that you’re a passive real estate investor, or you have been in the past. So right now, there’s fear uncertainty, we just went through the midterm election. People don’t know exactly what to do, right? I mean, it’s a little bit of a crazy time. So Greg, and I find ourselves talking to investors, especially like first time investors out there. And they’ll say something just like Tim, Greg, isn’t investing in real estate too risky. And I just was curious, you know, if somebody were to ask you that question, how would you respond?
Kyle Depiesse  32:06
There’s risk everywhere. I mean, you show me an investment that there’s no risk in but provides a good return. I’m all over it. But there’s risk everywhere. People always will need a place to live in, we’ve made a commitment, we make x, we know how much every year we’re going to invest. We just have our investment philosophy, and we’re sticking to it, we’re sticking to it in the good times. We’re sticking to it in the bad times when we feel a bit uncomfortable, or we have some fear. But ask yourself like, why is there fear? Where’s that coming from? Who are the outside voices that you’re listening to? who’s influencing that fear? Do they have any sort of way to benefit or take advantage of that fear? I think you have to be really careful who you’re listening to, especially in times of fear. And you have to understand what’s my investment, objective and philosophy. And let’s make an agreement in good times what we’re going to do in bad times, so when bad times happen, we aren’t afraid of it. We’ve already agreed to our philosophy. And we know our objectives. We have the right partners like you guys do that are handling things for us. Because in my instance, I’m trying to build a brand and I am not trying to be the one to go out there and get my lumps right now by investing in real estate. I’m going to find the guys who are the pros out there experts that are good at it, they have a track record at it. And I’m going to find the right jockeys, and I’m going to work with them because I don’t want to take those losses on my own. I’m going to work with guys and gals that know what they’re doing. I trust them. I don’t know if I’m answering your question correctly if I’m going off onto a tangent, but that’s how I
Tim Lyons  33:38
keep going doing great. Yeah.
Kyle Depiesse  33:42
When I went I didn’t even tell it. I don’t tell people this, but I have my series seven and 66 financial advising licenses, because when I was a stay at home dad, I was like, Man, I love finance. I love the markets, I just want to learn. And I don’t know, there’s risk everywhere. And we have to be comfortable investing in all sorts of different environment. You can’t just sit on the sidelines, like there’s always an excuse to sit on the sidelines. But I think it’s really important to just know what you’re getting into before it happens. And just being prepared for all the things. Yeah, that
Greg Lyons  34:10
is so interesting, dude, I
Tim Lyons  34:12
love that. And just to stack on top, there was a speaker at this conference, we went to this weekend, right? And he said some wisdom. We were at the top of the market. Everyone’s like, you know what, everything’s expensive. I’m gonna wait till there’s a correction, right? And then there’s a correction and everyone’s like, Dude, you see the blood on the street, like, This is crazy. I’m so scared. I’m not doing anything. I’m holding on to cash. I’m gonna wait until things start improving. And then things improve to the point where you’re like, Dude, I missed a great opportunity. Right? So like, when you view it through that lens, there’s always a deal to be had people make money in the good times and the bad right. So great answer, Greg. Go ahead. But the second question, yeah,
Greg Lyons  34:48
I think you and your wife hit a correctly when it comes to investing. You have your thesis already completed right? And whatever your thesis is, it’s good times or bad. times, you know, and your thesis is someone needs a place to live all the time, and that’s multifamily. If your thesis is people love washing their cars in good times and bad, buy a car wash, you know, invest in a car. Yeah, whatever that is that you want to do. And you feel so strongly about it. And some people, it’s the stock market, dollar cost averaging, I’m gonna invest this much per month no matter what’s going on. It’s finding that thesis and being comfortable with it. And the good times or bad I thought that was it was one of the best answers ever we’ve ever had to that question. Second question is a little bit different from our standard it’s going to do to Jim Rohn quotes. And I think with you, Kyle, your mindset of having so many different experiences is really important. And not only in your experience, but what’s going on. Now, Tim mentioned the midterm elections on certainly the stock market, high interest rates. And Jim Rohn said one time, every day stand guard at the door of your mind. And I think that’s really important. I think someone like you can really expound upon that, quote.
Kyle Depiesse  36:07
Usually, you hear the other Jim Rohn, quote, you know, it’s your that you’re the average of the five people you spend most of your time with, I like this one. And I think, discipline, I think mental training is all a part of everything. And if you could have a strong mind, because you will be tempted, you will listen to these outside influences. And you will say, like, maybe I shouldn’t be doing this right now. And if you do that, if you don’t have a strong mind, if you don’t have discipline, you’re going to ride the waves whenever the waves come up, and the waves will be every single day. But you have to be willing to stand in the face of adversity sometimes and say yourself, no, I’ve been whether you’re an entrepreneur, investor, a W two, it doesn’t matter. You gotta have some discipline, some conviction and a strong mind, because you will get challenged. And when you get challenged, you want to be able to stand firm and strong because most people will fall down. This is how you get ahead in life is standing strong in the face of storms and adversity. And you do that through a strong mind through strong convictions and training yourself, like I did was that 75 Heart program, like I’ve done different things like this, I’ve trained and I did an Ironman in 2018. And like, it was good, it was really good for the physical health, that Ironman, but mentally, it was the best I can do hard things. And when you train yourself to be in that mindset and that mentality, because as an entrepreneur, man, like and you guys would probably agree, I’ve been punched in the face so many times. And if you are weak in terms of your mindset, you’re just going to give up and you can’t be and so that’s why I think it’s really important because you will face adversity. So it’s a matter of standing or falling up
Tim Lyons  37:46
that. Kyle, I figured the Jim Rohn quote of you are the average of the five people you spend the most time with was too much of a layup for you. So we’re going to bypass that one. But there is another one, there is another one that says the formal education will make you a living and a self education can make you a fortune.
Kyle Depiesse  38:05
I think one of the things when you get in masterminds and you get in groups that you have to prepare for, is you’ll talk to 10 people, and you will have 10 different answers on how you’re supposed to be running and operating your business. And I think you have to be true and authentic to yourself because there is no like there’s playbooks on how to win and be successful. And we can learn that. But there’s also something to figuring it out on your own. And like I said, I never intended for this to be guys trip, I just did something I took action. I learned from it. And I went back at it, I got kicked down, I learned from it, and I went back at it. Now what if I was just following a playbook on what someone else wrote and told me what to do. It wouldn’t be authentic to me, I wouldn’t have the passion that I have for my brand and my business because that comes through when it comes out of what this brand has become. And so I think you need to learn yourself also taking in some input from others, but yeah, self education. I’ve learned so much about business life, but probably most importantly myself in the last three years because of building this thing. As a way I have through just learning failing and failing forward.
Tim Lyons  39:20
Dude, Kyle, that was awesome, man. Really, I mean, I just so grateful that you’ve made time to come onto the show it’s not usual to have somebody that has like a brand and success mindset just kind of go back and forth. But um, so I think it’s good to take a step back every once in a while instead of just grinding on real estate topics because this is I feel like it’s a clickable to a lot of people and I know when I first heard your story, it literally hit me like a freight train. So how can people find out more about guys trip and about you and your podcast? Give a shout out to all that stuff?
Kyle Depiesse  39:54
Yeah, so guys Don’t go I have no idea where that goes. But guys trip dot c he’ll, that’s probably the best way I’ve got all of next year’s trips that are out there available, implementing a new way to reach guys through another model called guy Saturday. So we take a four hour chunk of time on a Saturday, we do the same things help guys connect, learn and grow, and have a good time. So we’re entering new markets in 2023 on that, so maybe you’ll be in one of the markets that we’re testing. In, then I’m on Instagram, probably the most is just Kyle underscore dahlias. And then the podcast is reaching beyond just today. As of when we’re recording this I released episode 211. So we’ve been at it for a little over two and a half years almost so similar. Do you guys guess conversations on there? I do short form, as you alluded to earlier on. But yeah, I’m pretty responsive. I love to connect with people. I know that there’s social media can be this thing that drags people into this vacuum of scrolling and mindless stuff. But I love to connect with people on social media. So if that’s you, you’re just wanting to say hey, I’d love to have a chat. The best way is through Instagram. Kyle, thank
Tim Lyons  41:01
you so much, man. Again, I’m grateful for your guidance and your story and coming on and sharing it with everybody. So that’s it for the passive income brothers this week. We look forward to serving you again next week. Appreciate it. Thank you for listening to another episode of the passive income brothers podcast. We would be grateful for your support of our podcast by giving our show a five star rating and review and subscribing to our show on your favorite podcast platform. Don’t forget to take inspired action after listening to this show, so that you can start building out your passive income streams. Finally, head on over to cityside to connect with us and find out more information about how to get started passively investing in real estate