Embracing Humility, Vulnerability, and Balance

Tim Ludwig: Chris, thanks for joining me today. I’m super excited to have the conversation with you, and we’ve got a really strong friendship, and I think this is going to be a fun way to deepen that and for me to learn more about you, and then we can take it offline and you can learn more about me. 

Chris Powers: Tim, I hold you in the highest of regards. I think you know how I feel about you, and so being on here today with you is a real treat, and I’m excited for our conversation. 

Tim Ludwig: Yeah, let’s jump in. I think the way that I was thinking about this was really mapping it out over a few time periods that I want to make sure we cover in this conversation, and I sort of mapped it to your chronological age at different points. And so, starting with when you were seven is the first time I want to talk to you about in your life, but before we get there, maybe you could set the stage by telling me just about what life was like before that point. 

Chris Powers: Yeah, I was born in El Paso, Texas, along the border. I am fortunate to have two incredible parents and a sister. My mom was from El Paso, my dad is from the Northeast. He took a flyer, and his roommate was from El Paso, and took a clerkship, he was in law school in El Paso, came down from the Northeast, always wanted to check out Texas, ended up meeting my mom on a blind date and ended up staying in El Paso. So born and raised there. I’ve lived in Texas really my whole life. My dad was a lawyer for many years. We’ll talk about what happened when I was seven, which has a little bit to do with my dad’s career, but he was a lawyer when I was born. My mom, like I said, kind of lived in El Paso. She stayed at home with us. And then I have a sister that’s three years younger. And I’ve got nothing but great memories about the early part of my life. My grandparents lived around the corner. Again, my family had been there for multiple generations, so we kind of knew everybody. And El Paso’s a very- it’s a big city, but it’s a small town feel. And so, as far back as I can remember- And one thing I’ve realized as like I dig back in the past, I don’t remember things like some people do. Some people remember like acute things about the very early years of their life. There’re some things I remember, but I’m probably not the best guest that remembers super acute things. I just remember a good time, not a lot of stress, everything seemed relatively easy. I had two parents that loved me, and El Paso was a great place to grow up.

Tim Ludwig: Yeah, it sounds really idyllic. And on the memory thing, it’s funny, I remember all sorts of random trivia. There’re other people that remember every bit of a movie, or they can remember places and names or foods that they’ve eaten or things like that. I have terrible memory for all of that. Random trivia is the stuff that sort of sticks with me, and everything else is just kind of a hazy blur. 

Chris Powers: I’m like you. I remember the weirdest things, and then I won’t remember things that I should remember. My buddy knows every line from every movie he’s ever watched. I can’t tell you one line from any movie I’ve ever watched. 

Tim Ludwig: Same, same. It’s funny. So, El Paso, Texas, this nice idyllic existence, your dad’s a lawyer, and then when you’re seven, he sort of turns over the apple cart with the family. 

Chris Powers: Yeah, so, you never realize how crazy this is until you’re of age, and I’m actually 37 today, he was 37 at the time. He came home and basically told my family that he wanted to leave being a partner at a law firm and go back to undergrad to get his pre-med requisites and go to medical school to eventually become a doctor. And so, one, that’s just really a weird career path. And as I was growing up, I remember people telling me that all the time, like nobody ever does this. But now that I am- like I can’t imagine under any circumstance stopping everything I’m doing right now to go to medical school at this point in my career. So, he was married. He was a partner at a law firm. The world was his oyster. He had two young kids, I would have been seven, my sister would have been four, and he came back and said that’s what he was going to do. And so, these were amazing years in my life, but as I look back at who I am today and a lot of the good and some of the things I want to change about myself, I think they were born out of this. And what I mean by that is a few things. One, going back to medical school is a very taxing event, and you make no money and you’re never around. And so, you don’t do this for money. Let’s start there. You do this to follow a dream. And my dad would tell you it was the best decision he ever made because you only live one life, and he looked at this kind of like Bezos talks about, making decisions that you would regret when you were 80. If my dad were around today, I think he would have put that in the I would definitely regret never having done this, and I’m only going to live once. But it was a huge sacrifice. It brought its own set of challenges into the family. And so, at seven years old, he quit being a lawyer, spent a year at UTEP getting his prerequisites, and then when I was- later that year, we moved to Lubbock, Texas, and he enrolled in medical school. And so, again, I just put myself in his shoes – 37, 38, Harvard Law student, very well accomplished, and there he is with a bunch of 22-year-old kids that just got out of college starting medical school, and he’d spend the next four years kind of with them. And there’s whole stories about how he was like a father figure to a lot of people. But what that did was, it’s an interesting dichotomy when you spend your life, call it middle class El Paso, we didn’t have a ton, but we didn’t want for anything, and then you make a purposeful decision to have nothing for a long stream of time. In fact, you’re taking on debt as you take on medical loans. But our network was kind of- this was in the mid-90s, right before the stock market took off. So, all my dad’s lawyer friends that were in their late 30s, things were going well, the economy was heating up, they were buying a beach house. All the while, our family was living in a little two-bedroom, one-bathroom next to Texas Tech, like economically going two separate directions by choice. And so, I think it was like formative where I started to have these first inklings of like, oh, the reason why we’re not able to go on vacation or eat out to dinner was like an economic choice. At least that’s how I interpreted a lot of things. And then my mother, who’s a saint, like I think it takes a really special person to let your husband follow his dreams, uproot your life where you’ve lived forever, to make no money, and for her sake as a spouse, my dad, you’re on call a lot, you’re not around a lot. So it’s like a triple whammy, no money, treated kind of poorly, and never at home. That’s the medical school way. She would just kind of remind me that you don’t have to take this path. You can be an entrepreneur, you can make your own money, you shouldn’t depend on other people, they might treat you poorly. I think she would say these things out of frustration. My parents had a great relationship, very loving, but I think it was her almost remorse for the situation my dad was in, and she would just tell me from a young age, you don’t have to do this. And so, I think for the sake of this podcast and in our conversations, it was a formative stretch of years in my life where I think I started building the muscle of I’m going to be an entrepreneur, I’m going to be self-sufficient, I’m going to make my own money, I’m not going to depend on anybody. And of course, that’s come with a lot of good. We can talk about the challenges that come with that mentality, which there’s always a good and a bad to everything. But those were the first years of my life that- and I think the other part, I think it’s crucial, and you kind of brought this out of me, I think, when we were talking, you also kind of build a little chip on your shoulder because the network that you’ve grown up around that are all going on vacations, that are all going out to dinner, that are all doing all these things, it’s not that they’re better than us, but it was weird as a young kid to be like, well, we used to do that with them, but now we can’t. And we can’t because we made this decision. It’s not like my dad lost his job. And so that’s just a lot to process. And if my sister listens to this, which she might, and she would say this, I took the approach of I’m going to make it happen. My sister’s been plagued by the opposite. She’s very fearful of money and losing it. And so, it’s had two opposite effects, but we both trace it back to those years. 

Tim Ludwig: Was everybody shocked and surprised when your dad came home and said, I’m leaving law and I’m going to enroll in med school? Or there had been conversations leading up to that, I’m not really feeling it in law anymore, I think I might want to think about doing something else? Or was it just like he kept it all in his head and then it came out as this declarative statement that, honey, we’re moving to Lubbock?

Chris Powers: My mom could probably answer that better. To my understanding and I’ve never heard otherwise, it was a pretty big shock. Now I’m sure my dad had voiced over time to my mom, I’d always loved to be a doctor. My dad would say the only reason I became a lawyer is because my dad was a lawyer, and that’s a lot of the reasons why people choose their careers. So he probably had rumblings, but I do remember the broader friends and family being totally shocked by the decision. So my mom would probably say she probably knew about it a little further in advance. I remember them sitting us down at some point and trying to explain it. Again, I was seven, my sister was three. The truth is, I loved those years. Like, we lived in Lubbock, Texas. I played tons of sports. That’s all we did. I didn’t really think much of it, but there were seeds sown at an early age. And so, I don’t know, I think the one thing, and I kind of said it, is he was very keen on like I’m going to live- I only live once, and he was in a fortunate position to do this. And I think you see it, Tim, I probably see it. There’s a lot of people that get jammed up in a career that they otherwise don’t want to have, but because of circumstances, or maybe it’s their monthly financial situation, they’re already spending a lot, they’re kind of trapped into a career. And he just was like, I’m not going to do this, I’m not going to miss this opportunity. 

Tim Ludwig: Yeah, that’s really brave, and there’s obviously a lot of lessons that a child can draw from that. Some of the financial ones you sort of internalized and they showed up more later. I think even the example of living your one single life in the way that fulfills you the most is a lesson that must have resonated really deeply in a lot of ways. In its own way, it’s very entrepreneurial to be in the W2 career, partner at a law firm, and to do this huge pivot to take an enormous risk. I think that’s what entrepreneurship is about, like sort of charting your own course and taking risks like that. And he didn’t do it to start a business, he did it to change his entire profession at great personal sacrifice and a significant chunk of time that otherwise would have been peak earning years to provide financial security for his family and so many trade-offs involved in having the courage to do that. And behind I think almost every successful person that’s fortunate enough to also have a strong relationship, somebody really strong behind him supporting him even if frustration did leak out sometimes. There’s no way I’m sure that he could have done that without the support of your mom. 

Chris Powers: Oh, 100%. My mom was, like I said, she’s a saint for doing it. No, but I think you’re right. And I think there’s a book I’m reading right now called The Second Mountain by David Brooks, and I think my dad would just say he wanted to do something of service, and so being a doctor was his way of- and for whatever reason, that was definitely his second mountain, was this outlook on life, like, am what I’m doing really going to be fulfilling? Is it going to be more than just being a lawyer? And to him, being a lawyer just was not very fulfilling. And so, anyway, it was a really interesting setup to the beginning of my life that I think had a lot of ramifications on the the path that I’ve chosen in my life since. 

Tim Ludwig: Yeah, I’m almost ready to jump to the next age here, but before we do, talking about like beginning to plant the seeds of entrepreneurship, it was in this period, I think from 7 to 16 or so, is when your dad was in med school and becoming a doctor, so basically all of your adolescence and through high school and somewhere in there you got the idea to sell some golf clubs on eBay, right? That was sort of the first hustle that I’m going to do this and make some money. 

Chris Powers: Yeah, it’s like I tell some people, like today the day and age, these 16-year-olds are coming up with AI apps and all this crazy stuff, but back then, so much of the benefit of what we went through was like it just taught me the value of a dollar, it taught me the power- like I had to work- if I wanted something, I had to work to get it because there just was no money. It wasn’t like a gimmick my parents were putting me through or something like that, we can talk about that later. But so just very early on, it was very obvious that if I wanted a new baseball bat or I wanted a new baseball glove or I wanted whatever, I had to earn it, whether it was chores or something. And so one of my first businesses I started was, I was a golfer, was just buying used golf clubs and selling them on eBay and making a margin. And this was the early days of eBay when it was still kind of the wild west. And I would go to the club and the club would always have like lost and founds. And after a certain amount of time, those clubs were kind of deemed lost. You could buy them from the club, they’d give them to you. I’d go to players on my golf team and see if- almost do it on consignment. It’s like, I’ll sell it for you and I’ll take a cut. And that was a start. And then I had a lawn mowing business and car washing. And I say business, I mean, it was me. But I would go around the neighborhood. But I was just kind of hustling from like beginning of high school. And at the time, I really didn’t think of myself as an entrepreneur. Just maybe I had an appetite for wanting too much stuff, and so I was like I got to- 

Tim Ludwig: You just needed money. 

Chris Powers: I just needed money. I mean, there’s no other way about it. I was not thinking about it as like I’m a businessman. I just wanted stuff. 

Tim Ludwig: Yeah. Was that the same when you got to college and bought your first real estate property? Was that just about making money too, or did something flip at that point, you said, no, I’m a businessperson, I want to be starting and running businesses?

Chris Powers: So, by the time I got there, I had a couple mentors. So the answer’s like a little yes, a little no. So, by the time I got to college- I went to TCU, I was on a partial scholarship, my grandfather was helping me out. So, I had school paid for. I didn’t really have to- I don’t want to sit here and say it was to pay school bills. But after that, I didn’t really have a lot. I was going to get a few hundred bucks a month of allowance. And TCU is an amazing school, and there was a lot of people there that were from families with much greater means. And so I’m pretty observant. It didn’t take me but a week to figure out, oh shoot, if I’m going on spring break, or if I’m going to be able to go to the bar more than once a week or once a month, or if I want to eat meals out, I need to actually make some more money. And getting an $8 an hour job at the rec center is not going to be the ticket. I need to make something more substantial than that. And so, from that perspective, it was about making money. Now, I did start having the ideas, like I think, again, this is in hindsight, of I had two mentors that were in real estate, and the idea of being an entrepreneur was becoming more real. I had had an internship in high school where I worked for somebody, and even at that early of an age, I could get the urge that I wasn’t going to make the greatest employee. Again, I’m kind of flushing these out now. I don’t think I was exactly thinking this. But so, I saw an opportunity to start a business, but it was really at the time out of a need for- some people say like find a need in the market and serve your customers really well and start a business. I think my answer was my need was money and I was going to do something that I could do relatively well that had a good margin if done well and I’d figure out how to treat the customer well after that. And that’s when I started buying rental houses. 

Tim Ludwig: Got it, yeah. I mean, easy way to start. All right, so let’s fast forward to out of college and you’re 25. You’d already had some success in real estate, were starting to get a little traction there it seems like, and you’re on a good trajectory. But as life often does, it had other plans for you, and relating to your dad again, there was a significant trauma in your family. 

Chris Powers: Yeah, so this was another big one. So, I woke up. The actual 12-year anniversary was Memorial Day, well, the day of his accident, so it’s a couple days ago. I woke up that morning, I was at a friend’s ranch celebrating Memorial Day, and I woke up at 5.30 in the morning, wasn’t supposed to go home till the next day, but I had this weird feeling that morning, and I drove, I literally woke up at 5.30. There were probably 20 of us down at my buddy’s ranch. Again, I wasn’t even supposed to go home that day. We weren’t leaving till the next day. At 5.36 in the morning, I just woke up and said, I’m leaving. I had no reason why, don’t really know why. Got back to Fort Worth and went back to bed, was just going to- Again, I really wish I could tell you other than like something moved in me that I’ve just got to go home. I wasn’t having a bad time. It was all my best friends. So anyway, I get home, wake up, and my mom called me and she said- my dad rode bicycles, kind of like Lance Armstrong or like a professional would ride. He rode all over the country in races. That was kind of his hobby. And she said, dad’s been in an accident and he’s in the hospital, or he’s being flighted to the hospital right now, but I think he’s fine, and I’ll call you once we get to the hospital. And the reason why I didn’t panic is because two years earlier while I was still in college, I had gotten the same call, but at that time my mom was in major panic. Like I thought my dad had passed away then. And the next thing I do, I get a FaceTime call, and it’s my dad laughing in the hospital with a broken arm. And I’m like, you guys, whatever. Well, when my mom called me this time, it was like super peaceful. She’s like, dad’s been in an accident, I’ll call you when I get to the hospital. And there was the colonial PGA golf tournament going on in Fort Worth. And so, I remember telling my mom, hey, I might actually go out and watch golf today. Should I still go or should I stay at the house and wait? And she goes, no, go to the golf tournament. We’ll call you when we get to the hospital. Long story short, pulling into the golf tournament, my mom calls. She’s like, I think it’s a lot more serious. You should probably come home. And by the time I landed in El Paso later that afternoon, my dad’s friend picked me up, his best friend in the world who was riding with him that day, and I don’t know, there’s those moments in life where you can see the look in somebody’s eyes, and you don’t have to say much more. And he basically just said, we need to get to the hospital. I don’t know if your dad will be alive by the time we get there. And that’s when your whole world kind of changes. So he was in the ICU for 30 days, and then he passed away. And so very traumatic, 30 days out of left field. And so I think as it relates to a transition podcast, one, really had to grow up. That was the first- To be honest with you, I used to actually, growing up, think sometimes like nothing bad’s really ever happened to me. I would actually have those moments where it’s like I’d see all this bad stuff happening and that was the first time that I can really remember something so dramatic. And I’ve been so fortunate that it wasn’t until I was 25 that something like that happened. And I hate any time I hear something happening to somebody else. But that was the first time I looked at God and was like, why are you doing this to me? And anyway, I think the- 

Tim Ludwig: And there’s nothing you can do to prepare yourself for something like that. 

Chris Powers: Nothing. I mean, I had literally talked to him, he was healthy, he was- I mean, he was 57 years old. The sad part is he had become a doctor, he had just started his practice, he was starting to thrive, like all the things that we had been doing all these years. And yeah, there’s nothing you can do to prepare. I mean, in hindsight, I guess there is, but you don’t want to live life like tomorrow’s- any accident can happen. A lot of lessons learned out of this whole thing. So I had to grow up very, very quickly. I had to become like a father-type figure to my sister and a husband-like figure to my mother, but also be their brother and also be their son. I had to wind down a medical practice, which in Texas, you can’t really sell an OBGYN clinic, so that took two years of learning. I met my wife, who I just celebrated 10 years with, I literally met her a week before my dad’s accident. She met my family at my dad’s funeral. It was the first time she was introduced to my family. So that was going on. She was a saint. So, I had this awesome lady that had come into my life while at the same time balancing here. My business was starting to take off. I think being totally honest, I never dealt with it. Instead, I buried it. I didn’t lean into it. I mourned for a whole 24 hours, and then I kind of kicked into gear of like I’ve got to take action. I got to start taking care of my mom, taking care of my sister, dating this wonderful woman. My business was starting to really take off at that time and I’d already started raising money. I just had a lot of demands. And so, I suppressed it, and I’m sure you have follow-up questions that I’d be delighted to answer. But it wasn’t until, I told you we celebrated 12 years, I don’t think I came up for air to realize what had actually happened until about three years ago. There’s been a series of great things I’ve probably done and a series of really stupid decisions I’ve made over the last 12 years. I can’t blame it on my dad’s death. That’s not- But I think one thing you kind of learn as you snap out of it is when you bury a lot of trauma and never quite deal with it, you might think it’s over, but it just kind of finds its way back to the surface. And if I just look at the pattern of how I reacted to it and the next few years that happened, rather than slow down, it’s like life started speeding up really quickly and you’re not dealing with things. And so that was another… 

Tim Ludwig: I wonder, in the time when your dad died, especially starting a new significant relationship, and I think anybody that’s had a relationship knows the butterflies in the stomach and the excitement around that, and just the depth and degree of emotions in that moment must have been so overwhelming. Processing this cataclysmic event with your dad and the loss of him, this brand new relationship that I’m sure you were really excited about, and then the excitement of the business growing, and now this new sense of responsibility that you carry for your family members, packing all of that into a very small window of time just seems like system overload to me. 

Chris Powers: It definitely was. And again, there’s some things- I outworked myself for many years and went on overdrive, and I have a big energy level and a big battery level, but when it runs out, it runs out. You’re right about balancing the relationship with who would become my wife. Again, I just- I did this chart not too long ago, it’s like a life map, and you grade different years of your life. And I’ve only had one zero in my life, and that was when my dad died. And that is at the exact same time I also met my wife. And I rebounded pretty quickly out of there. She was a huge part of that next couple years for me. But I also give her, I mean, I give her a ton of credit. She just met me at a very interesting time in my life, and she rode through it, she was so graceful in there the whole time. I wish I could say I would have done that for somebody else. I mean, that’s a pretty chaotic time to introduce yourself into somebody’s life and hang around. It would have been very easy for her to say, call me once the dust settles. And she definitely did not do that and I’m grateful. 

Tim Ludwig: Chris, I’m curious, you talked about you just buried a lot of the emotions related to your dad’s passing and providing the support for your family. I’m curious what you think your mom and sister would have said you were like then. I mean, they were going through their own grieving process, but you’re trying to show up for them. Do you think that they were like, man, Chris doesn’t seem to be dealing with this or just thankful that you were showing up for them? Or what do you think their lens on you was at that time? 

Chris Powers: All the above. So, I remember, I don’t know if I’m ashamed to say this, it’s just like reality. First of all, my dad was like the center of our orbit, like he was the rock of the family. I mean, he was. So, losing him to my mom and my sister was cataclysmic. I mean, there was no worse situation on the planet for both of them than what happened. And it took them many, many years. I mean, to this day, 12 years later, my mom’s still never been on a date, not interested, she’s still in love. My sister’s still- I mean, she’ll cry about him every time she talks about him. She was his biggest fan. But I remember, I think the part that I said I was like, I’m not ashamed to say, it’s just after several years, I was also the one that was like y’all need to move on with life. Like, we have to pick ourselves up and move on, all to, in the rear-view mirror, realize that my day was coming, it just wasn’t going to happen for more years. I had thought I was not over it, it wasn’t over it, like I missed my dad, I wanted him back, but I didn’t want our family to be defined by my dad’s death. It’s kind of where I was coming from. So, I think they would have said, they definitely would have said I didn’t mourn. I think they would say I did everything I could to kind of make sure that they felt secure, financially, emotionally, that things would be taken care of. We’d figure out things with the court and the will, and we’d figure out how to wind this thing down. Like you guys focus on grieving and I’ll take care of business. That was kind of my way of showing that I was in it. And yeah, I think they’d know now and I’ve been vocal about it, three or four years ago, I don’t know a date, but it finally started dawning on me that like it was all real. 

Tim Ludwig: Yeah. My best friend passed away after I think we were 19, and I remember getting the phone call in the morning and just the utter disbelief and shock. And it’s been 12 years with you and your dad. I remember as far as like 20 plus years later, still having very vivid dreams about him that would just come out of nowhere or things that would just remind me, when those relationships are that important to you, it lingers probably forever, would be my guess. 

Chris Powers: Like my sister will often say, I don’t want to forget. And I haven’t forgotten. I’ve got a lot of great memories. But after 12 years, one of the greatest things I saved was a voicemail that he left me, and then I have an email that he wrote me, which you know about. But that’s one of the good things about having a podcast, Tim, if there’s any lightheartedness to this. Our voices are going to haunt our kids well after we’re gone. They’re going to be able to listen to hours of us talking. 

Tim Ludwig: I think about that. I think it’s part of the legacy that I’m going to be able to provide and that you’re going to be able to provide for your family. It’s actually pretty magical. And I’ll just say, your dad also, obviously I never met him, but as a father, he’s been an inspiration to me through you in at least a couple of meaningful ways that you shared a long time ago online about this little card that you had that had a handwritten note from him etched into it. And I thought that was just the most miraculous idea. And so, I went out and I found a vendor and I wrote something to both my kids and I had it put on this little metal card and I gave it to each of them and I said you just keep this. There it is. Yeah, you’re holding it up right now and showing it. Yeah. And just knowing that he did that touched me so deeply that I wanted to give the same opportunity to my kids to have something like that as a keepsake from me. And then the other thing more recently, that email you were just talking about which you also shared was just beautiful. I mean, it showed so much about his character as a person and as a father and what a role model. And so, like the legacy that he left, I mean, you got to experience him for 25 years. I’ve got two little snippets, but they were deeply impactful to me. 

Chris Powers: Well, that means a lot. He was an incredible guy and I think one of the best things I could do to honor him is try and be as good of a person as I can be. And he’s in me, and he’s a huge part of my life even today even though he’s not here. I think it’s one of the best things you can leave your kids is no doubt what you would do in any situation long after you’re gone. I can’t imagine thinking, I wonder what my dad would say, and then being like, well, I don’t know if he would say that. It’s so crystal clear, the decisions he would have made. And that’s sometimes haunting because I don’t live up to them. I’m like, dang it. 

Tim Ludwig: Between the age of 25 and the age we’ll talk about next, you were having a lot of professional success. Your relationship with your now wife was building, you started to have kids in that era. I think, before we get to sort of 32, 33, which is the next jumping off point, the question I wanted to sort of interject here before we go to you as a 32 year old is what were you like during those years? And I’ll preface this by saying that I’ve heard other friends of yours describe you in this era, a couple of words that came up were intense and mercurial. 

Chris Powers: What’s mercurial?

Tim Ludwig: So sort of like runs hot and cold. Like he’s sort of a tempest in a bottle. Like if you’re on his wavelength, like it’s all smooth sailing, but as soon as you start to deviate, boy, like you can get sort of cross with him and just be on different planes really quickly. But intensity was probably the thing that I heard most frequently. 

Chris Powers: Yeah, I mean, I think I can’t really say it any better than they said it, and that’s how I made them feel. I think one of my superpowers is if I’m on something, I can get everybody on board. And the downside of that is when I’m not on something, I can’t really fake it very well. 

Tim Ludwig: When you’re getting people on board, is that charisma? Is that willpower? Is that like- where does that inner part come from that leads other people in your direction? 

Chris Powers: I think it’s all the above. I think it’s charisma, it’s willpower, it’s a desire to never give up. And again, when it’s something that I’m really focused on and something that I had my eyes set on, I just felt like everybody in the world should be on that journey too. And like I’ve been told my whole life, if it’s not something I’m interested in, I have a very hard time faking that I’m interested in it or care to be there. And that’s not good. Trust me, I want to work on that, and I have worked on that. 

Tim Ludwig: How is it that not good? 

Chris Powers: Well, just, you can come off to people as not caring. I mean, you can just come off as insensitive. You can come off as- like my wife will sometimes say to me, she’s like, you can be looking at me, pretending to listen, it’s just you and I in the room, I’m talking, and I’ll ask you at the end what I just said, and you don’t even know I was talking to you, but I appear as if I am. And my teachers have told my parents that since I was a very young kid, that if I lose my attention on something or I’m not really interested in it, I have a very hard time staying engaged with it for long periods of time. That’s not good because the world isn’t about me, and that’s something I’ve had to learn in another transition. So in a lot of those years, it’s like I was on a mission to build a really big company, to make a lot of money, to be an entrepreneur superstar, to be all the things, and everything I just said was a me, me, me story. Now, I don’t think I treated people poorly, or I wasn’t a mean person. Now, I think people would say intense, probably tough to work with, had very high expectations, not a lot of grace, not a lot of slack if we screwed up. I was willing to work 16 hours a day, 20 hours a day, so I couldn’t understand why everybody else wasn’t as enthusiastic to do so. So I think probably a little misunderstood, always with good intentions, but that can, again, looking at it from the outside, I can see where the word’s intense. I will say- 

Tim Ludwig: Yeah, I think it sounds like a double-edged coin. On the one hand, there’s all the negative attributes, but when you bring the intensity, it’s also focus. When you are interested in something, there’s like a laser beam, I’m sure, shooting out of both your eyeballs that is pulling you forward, like a tractor beam to the destination, and people also rally around that. Like, that’s motivating and energizing to people, to see somebody that’s so committed to achieving something. 

Chris Powers: For sure. And like I said, I can get people rallied around an idea very, very quickly. And I don’t know, my whole life, like I’ve just never really- and this is something I want to change, but I’m also comfortable in my own skin, it’s just like who I am, I love to have fun, but also, it’s probably why we like going to Capitol Camp and doing things like this, I’m not interested in a bunch of chit-chat small talk. And I don’t know if that’s a good thing or a bad thing. I would much rather, maybe on the intensity side, get into a real- people would say like, man, it’s probably why I do a podcast. I can have some real serious conversations. Like, I’m interested in getting to the root of whatever we’re talking about and hanging out around there than just kind of glossing over life and talking about the latest score, the last sports game, and what we’re doing this summer. I want to know more about you and your life and what drives you. And some people would be like, oh, here comes- And my dad was that way in some degrees. My dad, people would joke like, if he sat you down and you were going to talk to him, you were going to talk about stuff you probably haven’t talked about in a long time, and he didn’t know any other way. And so, look, if you want to go talk about what happened at the Mavs game last night for an hour, I’m not your guy. If you want to talk about how the Mavericks were built and how they became a dynasty and why they’re great, I’m probably your guy. But if we’re just going to talk about last night’s game, I’m just not that guy. And some people would say an intense person would be not interested in talking about stuff like that. Now, I think the learnings from that are it’s not about me. And if the person that’s in front of me wants to talk about that, I can meet them where they’re at and I can be interested in it because they’re interested in it. It doesn’t- my life doesn’t have to be about everything I’m interested in. And so, yeah. 

Tim Ludwig: That’s an evolution for you. From your 20s into your early 30s, it was all the things you talked about a few minutes ago, which is like I want to build a huge business, I want to make a lot of money, I want to be- it was the me, me, me, I, I, I kind of internal talk. And that’s probably a good segue. That was working really well for the goals that you had set out, but at the same time, you’re building a family, you’re trying to, I don’t know, maybe not trying to be there for them as much as you should have been. There’re personal health aspects to all this. You can’t just be one dimensional and live a healthy, fulfilling life, I think, at least not for very long. And when you were 32ish, call it 32 to 33, there was a wake up call, right? 

Chris Powers: Yeah, there was. So, there was a lot of wake-up calls. So, I’ll preface this, and I think I speak for a lot of entrepreneurs, there’s a reason why entrepreneurs tend to have these type of, I wouldn’t call them crises, but if you’re ambitious about something, there’s something else that’s probably going to suffer. If you’re giving too much to one thing, you’re not giving enough to the other. If you’re watering too much of one plant, the other plants- whatever the metaphor is you want to use. And so, for the most part, I run with a lot of entrepreneurs. I’ve been around the scene for quite a while. At this point, it’s like I can’t think of one person that willfully neglects their family, that knows they’re doing it and is like I’m comfortable doing that. What most would say is like, I’m just providing for my family, or I love what I do. It’s usually not a malicious attempt, but what you end up finding a lot of the times is like, yeah, you’re not home a lot. You’re in a world where a lot of times you’re being told yes all day, and the first person to tell you no is your spouse, but you’ve been out working all day, so that’s not going to go over well. You start having kids, and you’re not there a bunch, but it’s okay because you’re providing. It’s all these things. And so, for me, I think it was a combination of two things. It was a combination of a lot. I finally started to become very fatigued and didn’t really know it. And so around 32, 33, I’ve said this before, my marriage was at an all-time low. I was on the verge of a possible divorce. I had been battling some addiction issues that were tied to work and knew that wasn’t good, but I had thought it would help me work harder. And I wasn’t happy showing up to work anymore. And so my personal life was kind of imploding. My business was taking off and was like soaring at this point. The whole world kind of thought I had it buttoned up and together. And I was just kind of melting inside. And even at the time, I didn’t fully recognize what was going on, but knew it was the first time in my life I was like, man, I am not a happy camper and I’m not making good decisions anymore, at least not healthy decisions, good long-term decisions. Maybe for the business I made some good ones, but everything else was just subpar at best. And again, I said I wasn’t happy at work. And so, I was like, well, I’m CEO. Again, I just couldn’t figure out why this company that I had founded early on was no longer energizing me. And I went to hire a coach and was like, I’m going to become the- I figured all my problems would be solved if I just became a better CEO, not like go home and work on the marriage and like whatever. And I remember it took me, I joke, I think it took me three months to say it, but I think I knew in three days that I shouldn’t have been the CEO of the company anymore. The skills required to take the business where it deserved to go and what was best for the company and not best for me was for me to move out of that role and my partner to move into that role. And that was a critical step that happened then. I cleaned my act up. I think, again, everybody, entrepreneur types tend to be addicted to something or multiple things. That’s what makes them successful and good is the willingness to grind. Sometimes your addictions can get into stuff you’re not proud of. I cleaned myself up there, got very healthy, and then looked at what is the most important relationship in my life, my marriage, and said, I have to rebuild this. And so, it was all these events. It was like, as I look back, it was all these things kind of landing at once. And it happened, I’m 37 now, I want to say I was 32, 33 years old as this was all taking place. And you’re kind of… 

Tim Ludwig: What’s the first domino that tipped with like the realization that you weren’t going to be CEO? Did that set off this chain of other ones? Like I’m going to get my physical health back under order. I’m going to work on my marriage. I’m going to try and reframe what it means to be a father. Or was it all at once and just a light bulb moment? 

Chris Powers: It’s a little blurry because it really was all at once. I think it was a series of things. So it was the addiction and having to overcome that and I was professionally treated to do so and did that whole thing. That was one moment where I was like, I remember being there realizing like I cannot believe this is where I’ve gotten myself to. And again, when your business is killing it, you’re just willing to overlook a lot of really red alarms. And I remember showing up to the clinic and thinking, man, I’ll be the only one here. And you look around, you’re like, oh, there’s a bunch of other high powered business people here. It turns out I’m not the only one doing it. And that was a huge sign. But it was my marriage. I mean, I can’t stress enough when you’re not living at your house, when you have kids, and I was just not willing to lose it. And I knew I was the problem. Like, that was the hardest part. The hardest part of any transition to a better you, I guess, is realizing you’re the primary issue you’re going to have to work on. And you can go for a while pointing at everybody else and thinking it’s everybody else that has to change around you, but eventually you run out of excuses. And I think I was met in that moment. My faith has become very important to me. I think for me, starting to read the Bible and surrounding myself with some people that pushed me to that, I didn’t have to read much of the Bible before I realized really quickly, oh wow, well, one, I’m like a broken sinner, but two, most of the issues that I’m facing right now are all self-inflicted. It’s from having a bad heart. It’s from having my ambitions focused on the wrong things. And I think I was met in that moment with like the path of I’m going to double down on the mistakes that got me here and think I can kind of dig my way out of this, or I can finally admit I probably need to reset and relook at my life and what’s driving it and all the things. And so, it wasn’t one moment, it was a series of moments. 

Tim Ludwig: When you flipped the switch there and you find that level of humility and you sort of remove the victimhood and say like I have to be accountable for my life, it has got to be one of the hardest reframings that a human can go through because we’re- all of our ego is working against that. Like, we’re the last person that we want to point the finger at, and to get to the place where you feel like either there’s no other choice, or you’re comfortable making it depending on how you got there, the end result is the same, that it requires tremendous humility, and it’s remarkable in my opinion. 

Chris Powers: Pride and ego will take you longer than you ever want to go and keep you there longer than you ever want to stay. They’re the most powerful forces on the planet because the hardest person- the amount of grace that we give to ourself is infinitely more than what we would be willing to extend to other people in most cases. 

Tim Ludwig: When you went through all that, obviously it saved your marriage and changed your relationship with your family members, but how much of a spillover effect has there been to other relationships? Are you able to bring that same, it’s both humility but it’s also vulnerability, it’s being more authentically you and open and being willing to not just be the headline of Chris Powers but the authentic human of Chris Powers? 

Chris Powers: Yeah, so I think naturally, I’m still who I am. I’m still wired the same way. But I have a new lens on things. And so, the one good news is this isn’t something, there is no finish, the finish line of this journey ends the day I meet my maker. I’m not going to like win this game. This is a day-by-day decision for me because my natural instincts are still, it’s not that I don’t want to be an entrepreneur, it’s not that I don’t want to win, it’s not that I don’t want to do excellent things, but why I’m doing them has changed. I understand the consequences now, which I never understood before, so that’s very fresh to me. And I think, again, you’d have to ask other people, and you might still say, Chris, I’ve gotten to know you pretty well, you’re still pretty damn intense, I think I’ve softened up infinitely from who the Chris Powers you would have met 25 years ago, or at 25 years old. Now, that might still be more intense than most people you know, but I know for certain it’s not who you would have met. And look, having three young kids will do that to you. But the same things that you do to rebuild a marriage you do to rebuild friendships, or even if you don’t have to rebuild the friendship, at least you still treat people that same way, which is, it’s just great. It’s just giving them the benefit of the doubt more than you ever would. And really, for me, it all boils down to this, maybe not all, but this is the thing I think about often. And I talked about this on stage, I think, at Capital Camp the other day. When your expectations for life are so high, the only thing you can really do is be disappointed every day. Because most things in life never actually are as good as you think they’re going to be, but they’re also not as bad as you think they’re going to be. And so I look at that period of my life, the bar was set so high, the reason I was capable of doing that, Tim, is because the bar I had set for myself was so high and unachievable that I was very comfortable setting that, even if it was lower than the bar I set for myself, it was still much higher than what anybody could ever do. And so, nobody in my life at that time- and again, I want to say, I had a lot of great friends, we had a lot of fun, this wasn’t necessarily a dark period. But for people that were in my life that I needed to perform, they would tell you I was exhausting and I was very intense because the problem was even when they did meet my expectations, I just moved the goalpost up further. And my dream was so big that even celebrating a win that to everybody else seemed like a big victory, to me, I had already predestined that thing to happen, so there is no need to celebrate yet. We’re not at the end. And so I don’t know if I answered your question, but I think when I said it all wraps up, it’s like you have to wake up and go, look, it’s okay to lower expectations. It’s an easier life for me, for everybody else. These are fake expectations in a lot of regards. Like, they’re made up. 

Tim Ludwig: Yeah. People won’t be able to see this, but I was nodding my head vigorously as you were talking through that whole thing. One last part I want to talk about in this epic of your journey is your partnership with Jason. When you decided that you weren’t the right CEO, he became the guy, and that’s a really important and I know special relationship, and so I’d just like to hear two minutes on that. 

Chris Powers: Yeah. Jason is such a blessing to me. He is a blessing to Fort Capital. He’s just an incredible guy for a lot of reasons, and it’s not just because he’s a great operator. I met him 10 years ago. We immediately became fast friends, started doing deals together, built trust before we ever decided to work together officially. And he’s just a guy that’s always put the company ahead of himself. He’s spent a ton of hours building the business and probably, he’s 10 years older, I would say having a better capacity to work on things that maybe he didn’t want to work on. And really, when it came time to deciding if I should be CEO, it was so obvious. The truth is, I mean, if we had a whole podcast just to talk about this transition out of CEO, he had been the operating CEO, if you just look at day-to-day activities, well before we actually announced it. It wasn’t- the truth is, like we joke, it’s not like his whole job title changed, or his job description. We just changed titles. And since he took over, the company has 5Xed. It’s become an infinitely better company. I never in my wildest dreams could have thought we’d be here, and I know I wasn’t capable of doing that. And he’s just very loyal. We’ve been through our ups and downs together. Every good partnership has. We’ve always gotten better for it. Our relationship today, I’d say, is as strong as it’s ever been. Yeah, I tell people all the time, I sometimes get a lot of the credit, just that’s how things work. Sometimes that’s just kind of my role, but I try and do my best to say all the credit to the team, any credit I get, the team should get more and really Jason. I mean, he doesn’t ask for notoriety. He’s not at it for himself. But I mean, the guy really, just getting straight down to business, is a business operational wizard, and he’s just somebody I really respect, and I hope we’ll work together for a long time. I’m sure we will. 

Tim Ludwig: Yeah, well, and it’s clear that your trust in him and his abilities has freed you up to look at life in a different way and to focus on different things, your podcast, your family, organizing events. Like it’s freed you up to pursue other passions that probably would have been dormant for a long, long time that are still additive to Fort in many ways still, but also, I think probably pretty enriching to you as a human being also.

Chris Powers: Yeah, again, I look at the last four years of having the opportunity to kind of rebuild some of the things I missed out on early in my career at home, and I couldn’t have done that without Jason. I don’t even think he fully understands that gift that he gave me. It was never like intended, but it just is what happened. And look, I would say on all that if we ever do a round two of this, I think I’m in a phase right now where, look, I’m 37 years old. I love building things. I want to get back in the saddle to some degree. And I think the next transition won’t necessarily, I’m not saying it’s back into business, but I’m in a season right now where I think I’m looking for what my second mountain to climb will be. And I’m sure Jason will be a part of that in some regard. I don’t know what it’ll be, but that’s kind of where I’m at right now is what’s the next thing I can tackle and hopefully go into this one with a lot more humility and perspective than maybe the first run. 

Tim Ludwig: Yeah, well, that was where I was going to take the conversation. You beat me to it. It’s sort of a nice bookend on all of this, given that you’re 37 now, the same age that your dad was, as you mentioned at the beginning, when he decided to leave law and go into medicine. And there’s some poignancy to that, I think. And I think one of the things that I was reflecting on our conversations leading up to today that is staggering to me is how much you have packed into your 37 years so far. I mean, it’s not- and I don’t just mean from a business perspective or from an activity perspective, but even emotionally. Like your journey emotionally and with self-awareness and maturity has been, it takes many people a whole lifetime plus, I think, to go through what you’ve done, and not to say that that’s easy or a journey that you would have chosen if you had the ability to look through a crystal ball, but like, holy smokes, if that’s the first 37 years, like the next 37 are going to be bangers. 

Chris Powers: I hope so. I am an old soul. I think I’ve always kind of been that way. I think when you’re moving fast through life too, like my wife will sometimes joke, for every one year a normal person lives, you kind of live three. And so it’s like dog years. I just get older. I hang out with a lot of people that are a lot older than me. I just naturally have gravitated in some regards. But yeah, I’ve packed in a lot. I’m grateful for it. I’ve lived an incredible life. I’ve had a ton of great experiences. I’ve had challenges. I wouldn’t really change anything, to be honest with you. Everything, I told you, happened for a reason. But you’re right, I’m very excited about the rest of my life. I honestly wish I could sit here and tell you I knew, had it mapped out perfectly, but I’m very excited about it. 

Tim Ludwig: You wouldn’t want that, that takes all the fun out of it. 

Chris Powers: I know. But that’s what I’m going to be- I know we’ll get to spend time together a few more times this year. That’s kind of where my head’s at right now, like, what is the next big mountain that I want to go climb? And again, reading that book, The Second Mountain by David Brooks has really got me going too. So, we’ll see what’s next.

Tim Ludwig: I have one final question for you. Given everything about your life’s journey so far, what aspect of it has been most surprising to you? 

Chris Powers: The first thing that comes to mind, I’m so surprised and so fortunate and grateful, my whole life is characterized by, they’ve just mostly been men, it just is what it is, a bunch of men, much older than I am, that really cared about me and my well-being at different stages of my life. And really, even at times when I didn’t really realize what was even happening in the moment, even taking it for granted, like I just thought everybody had these great mentors that told them, do this, not that, even when I wasn’t listening. And when I say took care of me, they took care of me when I wasn’t listening. Like they didn’t really give up. It wasn’t like a test. It was just- And so if I go throughout my whole life, there’s so many men I could have talked about today. But I think I’m just surprised, maybe it’s just, every step along the way, there’s been somebody that cared way more about me than I probably cared about myself or had something to offer me that has made my life infinitely better. And I sometimes don’t know why that has happened. I’m very, very fortunate. And I try not to take it for granted anymore. 

Tim Ludwig: I’d say you’re fortunate, but you’re also deserving. I think the people that have come into your life in that way are there for a reason, as you said before, and they see something in you, sometimes maybe when you didn’t want to see it or weren’t able to see it. But I mean, there’s a good heart in that body of yours, Chris, and I think that resonates for anybody that’s paying attention. 

Chris Powers: I really appreciate it. That means a lot. And you’re one of those people. I mean, I’ve collected these gems of people. Twitter and podcasting and everything else has expanded my network outside. And I’m like, look, Tim, we got 30, 40 more years together. That’s pretty awesome. 

Tim Ludwig: Yeah, I agree. Well, let’s end there. That’s a great stopping point, I think. 

Chris Powers: Thanks, Tim. 

Tim Ludwig: If you enjoyed today’s episode, you can find transcripts and show notes at transitionspodcast.com. Please also feel free to share this episode on your favorite podcast player with friends and colleagues who might share an interest in exploring the most critical moments from the lives of today’s business leaders.