The Money Habit Your Childhood Gave You

Why do you think it's so difficult for our internal experience to match our external experience?

I get out of school and so what, what did I want to do? I wanted to make a shit ton of money. Like, how can I make money is all I— I mean, I swear, like, that's all I cared about. Why do I have imposter syndrome and like this lack of, this like lack of full confidence in myself that I felt discarded by one of the two people who's supposed to love you more than anything in the world? Your parents. And for that reason, I needed to find ways to make myself feel that I was better than other people. That's where the judgment came.

Chris Gerbais is an entrepreneur and financial services professional with over a decade of experience building and advising businesses. He spent years running his own practice and working within larger firms. Driven to create a more modern, client-first approach to financial advice, Chris partnered with his friend and mentor Mark to co-found Five Oceans. Outside Outside of work, he enjoys surfing, golfing, and Brazilian jiu-jitsu.

Part of the massive anxiety and fear that I have about money is because I connected money being the reason that I didn't get to have a dad.

These fears aren't rational.

Right.

Easy to say until your nervous system gets triggered and goes into high alarm. Well, because our brains are pattern-matching machines, right? So you have these patterns imprinted upon you in childhood. And now our brains scan for threats. Over time, how does that start to re-pattern? How does that start to shift your relationship with self?

There was this exercise that we did that I did with Alexis, and it was, why are we the way we are with money today?

Take me a little deeper into that. Where do you think that starts to form? Welcome to Money Stories, where we have conversations with founders about money, meaning, and what makes a truly rich life. Today I'm joined by my dear friend Chris Gervais, who is an Unbreakable Wealth Community member, but more importantly, founder of FiveOcean Advisory, where he works with founders, high-net-worth founders, and on wealth strategy and beyond, which we can get into. But I'm really excited for this conversation, Chris, because you and I share such an overlap in philosophy. We think about things a lot in the same way. And so I'm going to start this show from a little different perspective than I normally do. Right now, you're very objectively successful on paper. Your firm is growing, you're making more money than you ever have, maybe not still feeling as successful as you might look on paper. And this is true for me as well, right? This is something that I help people with day in and day out. You know, wealth is what you help people with day in and day out. Why do you think it's so difficult for our internal experience to match our external experience?

You know, I can, I can share my experience, um, and I think I, I just have to imagine it's some version of that for everybody, which is that we have, uh, money stories. I mean, this, this podcast is perfect. I've been such a fan of your work because I've been into this for you know, a long time, um, 10, 15 years now. So my version of it is that I had some serious— or I have is the more accurate way to, to say it— some serious traumas from when I was a kid, and those still affect me today. I mean, I think that's a big part of it, and I'm happy to get into more details, but I think everybody has some version of that. So much of our who we are on the inside is developed at an early age, and you know, you know, you know just as well as anybody, it's not easy to, to, to break through those things. Um, even harder is to have the breakthroughs and just like remain broken through indefinitely. Like, that doesn't happen in my experience. Um, it's a, it's an ongoing process. So in this case, uh, you, you talked about feeling, not feeling as successful as, as maybe on paper. I'm guilty of the same human tendencies I think a lot of people are— comparison mode. I have serious fear and anxiety about money that I've done a lot of work on to figure out, you know, one, that I have it, and two, why that still shows up. Just because my income is higher, my net worth is higher, my lifestyle looks maybe a little bit fancier, those fears, anxieties have not gone away, unfortunately. I I really wish they did, but so far they haven't.

Yeah. And, you know, in many ways, this is the reason that I, that I do what I do is because this has also been a lifelong struggle for me, is I know intellectually the right things to do from a tactical money perspective. I know intellectually that my experience is not marrying up you know, between internal and external. And it's still a struggle. I think it's just so fascinating to spend so much time and dedicate myself fully to this work for so long. And yet still I find myself doing things. And here's also the big difference for me is I catch it quicker. And I remember the right answer and I return to presence and I remember that it's not a story. And maybe that's the whole game.

[Speaker] I think that's right. I think the game is to catch it sooner, having the awareness. And sometimes, you know what? I'm a big fan of having other people that can help catch it for you too. You know, having coaches or other people in your life. I think that we, even though we're, you know, in a lot of ways a traditional wealth management firm, right? Managing assets and advising on all the things, tax, insurance, I don't have to tell you. I think that we, through different processes we've implemented, we can help point out to people when they might not have the awareness themselves that, you know, they're, they're back in that money story and to help them live in a more intentional way. But, but yeah, having the awareness, being able to catch it sooner. Again, I just don't think— like, I personally had some pretty big breakthroughs about 11, 12 years ago now. And it's an ongoing, never-ending process. Like, I don't think there's this, this word transformation. It's a tough one for me. You know, transparently, it's a tough one for me because I think you can have breakthroughs in awareness, but I think that it's a constant working on for the rest of time. It's not a one-time, a one-and-done situation.

Yeah, I mean, that marries up with the model that I teach, which is awareness, insight, action, and integration. So awareness being what we're talking about. Okay, I'm having an outsized reaction to this scenario. Insight. Okay, I know where it came from. This thing happened in my childhood. This triggers my lack of safety. But I think a lot of us get stuck at insight, and I think that's why—

I was just gonna say that. Yeah, insight's not that easy.

Totally.

Insight is scary, takes a lot of work. Like, you got to be willing to go to some places that you might not have been before.

Absolutely. But as you get that insight, as you start to figure this out, now what? And it's that action. Okay, I've got to take this action over and over this corrective action, come back to presence, make a better decision. If you do that enough times over time, you start to integrate. But I teach it as a loop because even beyond integration, you still have to remain vigilant for it showing up again. And that's what, that's what we're saying here is that, yeah, the goal isn't necessarily to heal, it's just to become better at going around the loop. Yes. And improving our processes in hopes of eventually improving the outcome.

Totally agree. And look, I think we're talking, we're talking pretty, pretty high level here. Let's, let's kind of bring it, bring it down into some, some real life experience or stories if you want.

Yeah, tell me.

So look, for me, when I was 4 years old, it was me. My next youngest brother was 2, and my mom was pregnant with 2 more boys. And the day that she came home from the hospital with my twin brothers, my dad was already gone. He left our family and he wasn't even at the birth of my twin brothers. And so my mom had 4 boys, 4 years old and younger. And I grew up, make a long story short, and by the way, like I've cried telling these stories like a lot of times. Come on, that's what we do here. I may do that here, but I've really been psyching myself out to maybe not do that. Although, whatever, we'll see what happens. And to make a long story short, I associated— so I grew up without a dad. I mean, and my mom never remarried. My mom never had another boyfriend. She does now, decades later. But like growing up, I just, you know, just didn't have a dad. And that sucked. And it still sucks today. And it's going to suck for the rest of my life. I have two sons now, and it's like the— it's the most important thing to me to be a great dad for them. And I'll tell you, one really strange experience is to actually be envious of my own kids because there's some really cool dad shit, dad experiences that I'm literally never going to have. Bringing it back to money is I eventually came to connect that part of the massive anxiety and fear that I have about money is because I connected money being the reason that I didn't get to have a dad. Now, as an adult with more life experience, hopefully a little more wisdom, a little more perspective, do I think money was the only reason? No. But at some point in my life, I made that connection and I haven't been able to, to, to unmake it.

Can you just take me a little deeper into that?

Sure.

How did that manifest? How does you know, growing up without a dad, where do you think that starts to form this association with money and not having a dad?

When my mom brought my twin brothers home from the hospital, I remember sitting on our staircase. I was like, I was almost 5 now. It's one of the first memories I have. I remember our house being like pretty empty. But my aunt had flown in from Michigan to be there to help because my dad wasn't— my dad had already taken off. My mom's having 2 more kids. Mom's on the way home from the hospital. I don't know why I remember this, but I remember like our cupboards being empty, our fridge being empty. And I've even— I even at one point, like as an adult, asked my aunt about this just to make sure I wasn't like making shit up in my own head. And she was like, she told me, she goes, "Christopher, like there was no food in your house. I was so, you know, concerned." And I also like really wanna preface any of these stories with my mom is literally the hero of my life. You know, she gave us everything that she could. And I don't feel like I missed out on so much shit, but having a dad was kind of a big one.

Yeah.

So, You know, my mom, like, we're extremely close. I love her to death. And she, she, she, you know, saved my life, gave me it and saved it. But basically from, from there on, I, yeah, I had, I had like 4 or 5 other like, like very clear, vivid traumatic experiences that involved my dad fighting with my mom over money. Really bad, big fights. But But also just some other, you know, everything from my mom, you know, bless her, but had me serve my dad with divorce papers. And like, that was like a terrible experience. I had to sit in a courtroom when my dad asked the judge for a paternity test, which he was basically just trying to delay the whole court system because he owed my mom so much child support. He didn't help financially. And so we were always— I remember going, driving into the ghetto like 2 or 3 times, a young kid with my mom, to chase my dad down for money. So you asked a question about like, how does it manifest with money specifically? It felt like all of it was about money. And again, now, like when I say maybe it wasn't, I feel like there was some mental illness going on there. My dad had a whole— my dad's an immigrant from Spain. He had his own shit that I didn't even learn about. I traveled to Spain. I wrote a letter to my grandmother saying, I'm your American grandson. I want to come meet you and spend some time. And I learned some things about my dad. He had his own shit with his relationship with his parents. I found out was extremely cold and whatever. Like, I've learned some stuff. But when you're 5, 6, 7, 8, 9, 10 years old, that's when I linked it. You know, I think somewhere physiologically with money and the lack thereof. And I blamed all of the hard shit that, you know, we went through as kids on money. So hopefully I answer your question.

Yeah, no, I mean, thank you for sharing that, that insight. It's, it's clearly not easy to go back to those places. And so I just want to honor that. But if you could distill maybe the belief about money or the specific money story that that left you with, that those childhood experiences— could, could you do that?

I think it's that I'm deep down, I'm afraid of losing my family if I don't have money and provide. That's what I think, you know. Again, I've done a lot of work. I'm not just coming up with this right now.

Yeah.

Um, but that's what I've That's what I've distilled it down to. Now, I know, like, to your point, like, I know that's not fucking true. Even recently had some, you know, fear and anxiety about money pop up, like, more so than it has in, I don't know, in the last several years. And had some really great conversations with my wife, and she and the boys wrote something to me like, you know, you're an amazing dad and we love you so much. You're doing a great job. Wrote a little note. And like that, in that moment, reading that, like, just my heart exploded. And I remembered that your kids don't give a fuck about money. They care about you being around and loving them. And I was like, oh, oh yeah, I needed that in that moment. And it just, it was like an instantaneous rehealing, at least for a while.

Yeah, I think that's, I think that's exactly how it works, right? Um, because you've pinpointed a couple important things. Number one, these fears aren't rational, right? Easy to say until your nervous system gets triggered and goes into high alarm. You can't just be like, oh, that's not real, right? Because your felt experience, you're going back to those childhood wounds. Your nervous system is going back to those childhood There's a lot going on underneath the hood.

It's the nervous system, man. Like, it's hard to control the nervous system.

Yeah, well, because our brains are pattern matching machines, right? So you, you have these patterns imprinted upon you in childhood, and now our brains scan for threats, waiting to confirm that that pattern is activated again. And that's how our brain— it's a comparison tool. Yeah, right. And so when external circumstances present that look like that same. And, you know, yeah, your circumstances are wildly different now, but that core fear still imprints and it's still real.

I'll share another one with you just really quickly.

It doesn't have to be quick.

I know, because you and I both know other people that, you know, these stories are— when you see enough, it's like there's a lot of same stories that, you know, they're unique, but Yeah, but it's all the same. Yes. But another thing that I have put together is that pertains to entrepreneurship. So one thing I knew about my dad is that he was a serial failed entrepreneur. So he was always broke. But I knew from whatever, like I'd hear from my mom or learned something from time to time about some other business that he started and then failed and then started and then failed, etc. Uh, the person in my family who had money, who I thought was like the wealthiest person in the world, was my grandfather, and he was a professor at a university. And so, um, that whole idea that like the person that has their life together was a good father and has a great family and is now traveling he did the stable thing, like the stable thing. Entrepreneurship has created a lot of pain and chaos and suffering in my family. And so that's another thing that's tough for me now because I'm an entrepreneur, but I'm scared shitless of like, yeah, that nervous system will still take over. I'm like, am I built for this? Am I built for this? Like, does that make sense?

It makes total sense. And so when this starts to surface, what do you do in that moment? What do you do when you go, am I really built for this? How do you navigate that?

One of the things that I've been able to do is, is really just turn to my family, like my, my specifically my wife and my kids, whether that's like going down and sitting next to one of them and playing playing with them or walking downstairs and grabbing one of them and hugging them, kiss them all over the place. Like, just that can get me out of it pretty quickly. Like, to really what I'm doing is realizing how lucky and grateful that I am to have this thing that I always wanted. I always dreamt about having a family like mine, and I have it. And so remembering that in those moments is what is what I do. That's my go-to number one tactic.

Yeah. Yeah, I mean, what I'm hearing is returning to presence.

Yeah.

Right? Because when our nervous system gets triggered, we're either living in the past or we're living in the future. Right? And in that moment, you're breaking that living in the past loop and just returning to what's true right now. Does that feel right?

It does. You just put words on, you know, that is practically what I do, but you just put words on what, what is, what that's at, what's actually happening there. Yeah, I'm being, going back to the present of what I have right now and then specifically even putting my hands on it.

You've got a really tough childhood, right? You, these money stories are hardwired. Grow up without a dad. How do you start to unwind this or even become aware of it in the first place? Can you kind of take me through your journey?

Yeah, sure. So, um, I got really fucking responsible at a really young age. And so what I personally turned to do— now, my brothers, not— they, they didn't necessarily do that. We're all so different. What I did is I became a hardcore rule follower. Like, I was gonna— I was gonna get good grades, never get in trouble, and go to college, and, you know, That's what my grandfather did. And that was the guy like that I wanted to be like, because he again had stability in the family and all that. And so I did that. And I also turned to sports hardcore. So I played football and baseball from early on all the way through. I played both sports in college, like my whole life. Just a whole other thing not to harp on about. My dad's never seen me play a game of anything in my life. And now I get to coach, like I'm coach of my kids' T-ball, like all that, all that what can sound like really cheesy, like, dude, it is like my, it's my heart, man.

I don't know.

I'm living that fucking dream and it feels so good. I gotta tell you. But I turned to sports hardcore. That taught me a lot of lessons about life, discipline, overcoming hard stuff, especially football. I was undersized. Like it was, you know, it was just, it was really good for me. Sometimes I say sports became my father in a lot of ways, just teaching life lessons. And then I get out of school. And so what did I want to do? I wanted to make a shit ton of money. Like, how can I make money is all I— I mean, I swear, like, that's all I cared about too. It was bad. But I also know that that's not abnormal for young men to—

Especially growing up in LA.

—care a lot about making money. Yeah, yeah, exactly. So Another thing, when I went to college, it was kind of the— going to college was the first time I was surrounded with a lot of people that grew up with a lot of means. And that was really good for me because I was like, oh, shit, this is kind of nice. I like this. So I get out of college, though. My first real job was at an investment banking firm. I didn't, I don't even think I knew what investment banking was. I just knew, like, I heard you could make a lot of money doing it. I was just kind of all, almost all through my 20s going through the motions of, you know, working hard, trying to work my way up in, in a career, having, I would say, you know, moderate success. I was relatively speaking, like, successful. Um, but it was in, sorry, let me pause you there.

Yeah. When was the first time you felt successful?

Hmm. The first time I felt really successful was not that long ago. And I'm 45 years old. I have a successful business. Like, it's almost like a pinch me, like to even say that confidently. And in the back of my mind, it can all fall apart at any moment and all that. But I think probably about 5 years ago. Is there a moment? You know what? I also want to— I also want to— I also want to take that back a little bit. And I got to— because for me, and this is a perfect example, when you ask that question, I immediately think financially successful. Just like, that was my— that's my automatic response. But I've had some other experiences where I felt like really successful in life. Let me try to answer your question about a moment financially successful. I think, look, I mean, within the last few years, I've purchased a home in a beautiful neighborhood and have provided this really, you know, nice upbringing for my kids. My son goes to private school, like all those things. Like, yeah, I feel That feels successful. I didn't even know anyone that went to a private school my entire life. So for me, I will say all that feels financially successful. Now, the real shit though is sitting inside said house at Christmas time, the first Christmas we were in there, and we were all just like watching a movie, but like my wife and the baby and my older son, and I had this moment. I looked around, I was like, oh my God. Like the warm, loving feeling just overcame my body and I just felt bliss. And like I said earlier, like it was just the thing that I always dreamt about and it was happening in that moment. I was able to actually be present in that. And that's happened to me a few times, even on the baseball field coaching my son, that happened once too.

So back to investment banking, you're going through the motions. Yeah, yeah. You're moderately successful. Yeah. Sounds like you don't feel successful yet, but no, moderately successful going through investment banking. Take me back to those days.

What was that like? Well, again, I was looking back. I know, I know. I was just going through the motions. I was partying like, you know, like I was in my 20s. I was in my 20s, but I was working hard and, you know, really responsible at work. Eventually, I knew I didn't have any passion for the type of investment banking I was doing. So I kind of had a quarter-life crisis. And just to keep it on career for a moment, I end up at a big bank as a financial advisor. This is my first delve into the world of financial advice and wealth management and all that. And again, first few years of that, I'm kind of just going through the motions of life. Worth, I think, worth doing in this moment is fast forwarding to 2013. So this is where things really changed for me. Do you mind if I just fast forward to 2013? Send it, bro. The other stuff's boring anyways, dude. Yeah, take me to 2013. Yeah, 2013 sounds pivotal. I'm ready. Yeah. So, so, so one of my best wide receivers in college was a guy named Lewis Howes. A lot of people have heard of him. Social media world, right? Um, he was my roommate my senior year. We were like dynamic duo on the football field. He had moved to LA. He invites me up to LA to hang out. We have a great time, great weekend. He tells me, you should come do this leadership workshop that I recently did. It was awesome. I think you'd love it. Him being one of my best friends and, uh, and a successful entrepreneur, I was, no-brainer, of course. When is it? I'll be there. So I went to it. Well, what it really was was a deep dive, hardcore, experiential emotional intelligence workshop. And it was, it was pretty hardcore. I mean, it was, it was nutty in a lot of ways. If you went all into it, which I did, the experiences, the way that the entire program was set up, you were given a path to go deep. And that, that experience, which was a multi-month experience, like really for the first time got me to have awareness. I think this is where your question originated, or one of your questions at least, like when, when did I start connecting this stuff? That workshop was the interruption that made me go, oh shit, this is why, this is why I have like some self-love, self-confidence issues. Like Yeah, I didn't have a dad. That sucks. And that can fuck you up in a lot of ways. I never even thought about that. I just charged through life like I didn't care that I didn't have a dad. Not that I didn't care, but I felt like if I— yeah, if I worried, if I was a victim, you know, because of that, I was going to be held back by that. So I just charged forward. But in that workshop, I really started to understand some of my core wounds. And then I could— awareness started, and then I began to be able to do the work to start overcoming them. And worth noting, in that workshop, there was another person who was going deep as well. She also had some serious dad issues, and we connected over that. And that person and I just celebrated our 10-year wedding anniversary.

Personal development is a great place to meet a partner. I happen to share a similar story.

It was for me, that's for sure.

But I want to go back to that workshop if we can. You, you go in almost totally unaware, or at least, uh, uh, not looking at all of this stuff yet, right? For sure. It's sort of been locked up inside. I'd say totally unaware.

That's fair. Yeah.

As you start to dive in and go deep for the first time, what's that experience like? Going like, oh man, maybe, maybe this costs me more than I thought. Maybe this is holding me back, or What was that like?

I mean, convulsive crying, like convulsing and crying and having a physiological experience. But the truth is, is that what it was like was amazing. It was freeing in a major way. It felt like nothing I'd ever felt before. It felt like the same way, um, I've, you know, a ton of friends that have done psychedelics. I haven't, at least not yet, but it felt like the same thing, um, I've heard a lot of my friends describe through, um, you know, plant medicine experiences, things like that. So it felt— having those realizations and then, um, really being able to embrace what's possible for me now having this awareness And being able to break through it felt like just pure, pure love.

And do you remember specifically what some of the key realizations were from that workshop?

Well, yeah, I mean, for me it was, why do I have imposter syndrome and like this lack of, this like lack of full confidence in myself? Why am I— there was, there was also, you know, I'm asking myself like, why am I so judgmental? I was, I was a judgmental person. My friends and family, maybe my family would have said that. I don't think my friends would have because it wasn't like necessarily outwardly, it was just, it was on the inside. And what I, what I put together was that I felt discarded by one of the two people who's supposed to love you more than anything in the world, your parents. I felt discarded by my dad. And for that reason, I needed to find ways to make myself feel that I was better than other people. That's where the judgment came, being judgmental. I felt like I was less than again, because if one of, one of the two people who's supposed to love you more than anybody doesn't, or at least doesn't show it, it made me feel, yeah, made me feel like a, like an inferior person. You know, how I related was there was like all this stuff that I viewed as like really good shit, like a loving family and like life experiences that people have, whether on their own or with their families. I felt like that just wasn't for me. Like, like the universe didn't have that in my deck of cards. That's what it felt like. It felt like that just, that good life wasn't for someone like me. And, and it was, I connected that I had come to that belief system because I was, you know, because I was discarded by my dad. That's what I really connected in, in that, in that experience.

I think what's important to point out here, at least what I'm getting out of this, right, is going in, you're afraid almost to look at any of these experiences because that might make you a victim. Mm-hmm. But then in looking at them, it was actually the opposite, right? It's empowering. You're now starting to see how these stories are holding you back. So how does that start to translate into your life from there?

Ooh, that's a good question. I want to put one caveat on like the— I was not looking at these things because I was afraid. I think more accurately, I just, I had no clue. I was just completely unaware, just like floating through life without any awareness. It wasn't like, oh, there's stuff I really need to work on. I'll get to it at some point when I can overcome the fear. No, like I was literally clueless about it. Yeah. So just wanted to point that out. Now, to answer your question, so what does life look like after that? I marry the girl of my dreams. I mean, the girl of my dreams that I, that I, in the previous Chris would have been like, not even going to bother because way out of my league. No shot. Wouldn't even have thought about trying to, you know, I married that girl. I had— I got the confidence for the first time to start my own company. I wouldn't have done that without that shot in my arm at that time. I know I wouldn't have. So I moved to LA, get married, and start a business all in like 12-month period as a result of this newfound confidence and love for myself. So, like, things changed quite a bit, pretty fast.

Yes. Sounds like you took that experience and went right to action.

I did. I did. I did.

And over time, how does that start to re-pattern?

How does that start to shift your relationship with self? Re-pattern is in, like, when I was talking about earlier, it's not transformation one time and then— Yeah, yeah. I mean, first few years in the marriage, Alexis and I are fighting over money. Not like crazy hardcore fights that I experienced a few times. Fighting over money with my spouse is right up there with like worst nightmares, right? Like the thing I want to avoid more than anything in the world. And so I was very sensitive to that. And it was, look, I'm not going to accept that as part of this relationship. And we were going to do whatever we need to do to not let this be a part of our relationship. So marriage counseling and talking about money. I was at the time, because I've, as I said, I've been so interested in this stuff for a long time. I was at the time in a financial therapy, like master certificate program, because I was just interested in it, studying. Reading books about financial therapy, which was a pretty new field even at that time, 10, 12, 13 years ago. And there was this exercise that we did that I did with Alexis. And it was, the point of the exercise was to get to why do we believe, why are we the way we are with money today? And it was basically a, like a lifetime line, but it was money. It was, a timeline of best experiences associated with money and worst experiences associated with money. You go through and you put some words, titles, and some descriptions. And we both did that and shared it with each other. And it created a new level of empathy and compassion for the other person. It was like, okay, I understand way more now why you're reacting like this. You understand way more now why I'm reacting like the way I am. Now we can start overcoming this. So yeah, you asked how does it start reemerging? Like, I remember that it's just a few years later, you know, having some arguments with Alexis about money, but I refuse to— like I said, we just had our 10-year wedding anniversary and we have not— fighting over money has not been a thing, a part of our relationship. But that hasn't happened by itself or on accident. That's taken a lot of work.

Yeah, this is such a, a salient point, I think, when it comes to relationships, right? Is, um, the, the way I view things is there's two entities. There's you and her, and you both have to work on being separate whole people. And then there's the third entity, which is the relationship. So you've got your own internal battle with money, she's got hers, and you just did this exercise to see where that's coming from. And now in, in that third entity, the relationship itself, you and her may not be completely resolved, but at least you can be resolved in relation to each other, or, or the best you can. I mean, am I— is that making sense? Is that kind of how it's—

yeah, I mean, I totally agree that two people have to be happy, whole people on their own before they even have any remote shot at being successful in a relationship, in my personal opinion. Um, but yeah, I mean, doing that The doing the work, whether it was that exercise or counseling, increasing the compassion and empathy for the other person, all that. Yeah, I mean, I think it's completely necessary. The other option is just to kind of ignore it forever. And like, that doesn't seem like a recipe for success. At some point, high likelihood things will boil over, right?

In my experience, yeah, that seems to be a pretty fair assessment. So, so from there, what's the path to Five Oceans and what does it look like today?

Yeah. So I started to give you— I mean, this really puts into perspective that shot in the arm that I got from doing that deep work, that emotional intelligence workshop. It was very strong because I started a wealth management practice with no clients and no assets. You shouldn't do that. That's not a great idea. The traditional path to having your own wealth management firm, start at a household name, develop a book of clients, spin out, start your own thing, take your clients with you. That's what I believe is and would've been the easier path. I didn't do that. I was like, I could take on the world. So it was tough, but I did it. Just a lot of hardcore, You know, the hustling was trying to add value for people as much as I possibly could. I was saying yes to everything and everybody. If the second someone said, I've been wanting to learn more about investing, or I could use some help, would you mind, like, could we have coffee or something? Sometimes like, yes, yes, yes. And I was just giving advice for free anywhere I could. And eventually some of those people became clients. Several of those people became best friends and clients. Several of those people were like me, although as an entrepreneur, more successful at the time. They were young, ambitious entrepreneurs. So eventually these people were now best friends, clients, and wealthy. And so my business, I got to kind of, I got to grow up, you know, with them. Eventually I was sort of forced into needing to learn how to advise the ultra-high net worth because again, never even knew a single person that was ultra-high net worth, you know, until I got into college and some of those, you know, friends, families or whatever. But I certainly didn't have experience with that level of wealth. But my clients allowed me to learn and I did. I did the, you know, 10,000 hours on the phone with CPAs and estate planning attorneys asking a bazillion questions. And they all were happy to give me their time and answer all my questions because I had a bunch of clients to refer them to and, uh, or for to refer to them. My business grew and, um, I first launched that in 2015. In 2020, I came together with my now business partner and started Five Oceans. And, and our idea was I don't want this to be a pitch for Five Oceans. That's not the point of this interview. But my partner and I both are like, look, I knew more than anyone. Like, I'm almost afraid, like, all this wealth management shit. But like, we knew that so much of the knowledge and the technical stuff, if not, let me just say, all of it is a commodity. It really is. I mean, in 2026, more than ever before, right? Even the most advanced strategies these are not secret strategies that are not out there on ChatGPT or that any advisor could figure it out. We both believe that we're already adding a lot of value for our clients in the life planning, life strategy, in the psychological, emotional parts of those relationships. And so because we were both on the same page about that, we started Five Oceans. We have this whole, a life strategy piece of our business. We have a full-time life strategist on staff and, you know, like getting someone to optimize their financial plan, that in and of itself, number one, isn't really that exciting to me. Like that can be done. That should be a no-brainer. Like an advisor needs to be able to do that. Like that's table stakes. Helping people live more intentional, happy, fulfilled lives. That's, that's what we're in it for. I think that's what anyone wants to be doing with their lives, right? So that's how Five Oceans came about.

This is where you and I have so much overlap because I think most high net worth, high performing founders start with the wrong question, which is how do I optimize my finances? And I think there's a first principles question that sits underneath that, which is, Optimize for what? Like, what are we actually doing here? And I think you have to get really clear about your values, the life that you actually want to build. And once you get clear on that, right, what is the life that I want to live? And more importantly, who do I want to be in that life? Yeah. Now we can start answering financial optimization questions because it's a matter of allocating resources at that point.

You can't do the financial thing without doing the other part first. And the human tendency is, if at least if you're like you and me, we'll spend 99% of our energy on figuring out the optimizing of the financial stuff and very little time on the other thing. But it, it should be flipped. It literally should be flipped on its head and should be the other way around. But that's just not how we do it as society. And that's, you know, we're You and I are doing work to help people try to realize that and then actually do it. 'Cause you're exactly right. Why are you optimizing in the first place? Such a big question. I wanna make a point in that, in this whole, why are you optimizing? Another big piece of it is what is enough? I mean, that question alone is like a, that's a killer question. What is enough for you? Okay. And here's where, here's what we've distilled it down to. If the answer of why you're building wealth, why you're building your business, why you're optimizing your financial plan, the obvious human answer is, I don't— to get it, to get it as big as possible. I mean, isn't that what we're all doing here? Like, to build as much as possible. Big problem with that: as much as possible is not a quantifiable number. You can't quantify it. So now your goal, you, you're literally Aiming at something that's not quantifiable, that is a recipe for disaster. That is not a recipe for happiness or feeling like you've accomplished enough. Enough is quantifiable. Now you can turn your goal into something that is quantifiable and it is achievable so you can actually achieve it. But doing the work to figure out what's enough, that's hard. And Doing that work as a busy entrepreneur in your 30s or 40s with young kids and life happening and making that a priority is even harder, but it is absolutely imperative. We all need to be doing that work.

I'm shouting from the mount— you're screaming my message right now.

I mean, I couldn't agree more. That's why we're instantaneous homies almost.

But to take that step further, right? Doing it in your 30s and 40s when you have young kids, that's the most important time to do that. Because if you can quantify how much is enough, right, now you can avoid the traps. And by traps, here's what I mean, right? Everybody knows money can't buy happiness. That is, that is absolutely true. But it can buy a lack of unhappiness. And I think you and I would both agree, for me, one of the paramount, like, like most glaring ways to be unhappy is to wake up when my kids are leaving for college and realize I sacrificed my time with them trying to get money.

And so many people do it, but they're doing it for their kids. Yeah, that's the mind-blowing part.

That's the, that's the biggest lie we tell ourselves.

It's the biggest lie. That's, that's tough, man. I'm, I'm here, like, I, I will not let that happen to any of my clients because I will fucking tell them to their face you're doing it for your kids, you're full of shit. That's not what's happening. But, but that is it. It is, it is a common, it is a common thing. Everything I do, I do it for my family. And it's bullshit. It's tough, man. Like, it's, it's, uh, it's tough. It's, um, you can relate, you can relate this too with the utility of money. Like, like spending I actually, one of the biggest, believe it or not, like one of the biggest values I think I bring to clients is you might, it might not even sound valuable, but I'm convinced that it is, is getting them to spend more money even when their expenses are high. But when they have young kids, like when you can either spend this money now when you have young kids and you have this one opportunity and It's an amazing time to use your money, or you can turn it into more money down the road when your kids are out of the house and you're retired and it's you and your spouse and you're trying to figure out the next place you're going to travel to. And it's like, let's use the resources we have to optimize our life experience. Again, not just to optimize building the biggest thing over time.

So— Yeah, I mean, one of my universal rules is you can always get more money. You can never get more time. Right? And if you think about it, right, there was a point in your life where all you wanted was what you exactly what you have right now. Yeah. And there will be a point in the future someday when all you want is to come back to the days that you're living right now.

That's what they say, man.

That's what they say. Right? And so, yeah, helping people inhabit that present moment, right? And use money to create a fulfilling life, I think is, is, uh, it's why I do what I do. I know it's why you do what you do. So you work with high net worth founders, right? Let's, let's just say a 40, 45-year-old guy like us walks in your office working his ass off, right? The cracks are starting to show at home. He asked you how to optimize his finances. What do you tell that guy?

The first thing I'm going to do is ask him a million questions about his life. But I'm also going to ask him to rate his level of satisfaction in specifically for us, 5 different areas. I know you have your own framework that's very similar, but finances, career, relationships, fun, and health. With the answers to those questions, and then also why, now we have a baseline of where the, where those cracks are. And now we can begin to, if we're going to, we're going to optimize your money. I, we need to know the answers to those questions because we're going to use your money to optimize your life. Okay. We're not going to use your money to optimize the biggest portfolio we can possibly build over time. We could do that. That's not, that's not valuable. Now we can begin to allocate resources to improve the scores. Wherever they need to be improved. With founders, a lot of times too, this other aspect is at that, if they're, you said a guy comes in and there's some cracks, you know what most of the time that person is looking to do? They're looking to get out of their business. Yeah. That feels like the easiest, quickest path to like solving all the problems. And that's an interesting thing too, because if you get desperate enough and you wait long enough, you're likely not to have an optimized exit because you're going to be rushed through it. You're— you don't have time to get the business prepared the way it should be to get the highest multiple and all that stuff. So that's like another piece of the dynamic.

My favorite question there is, are you selling because your business is optimized for exit and you've grown it as far as you want or can, or are you selling because you're tired?

I almost— I don't know if I've ever seen the first one when I'm talking to people, right? I'm serious. Like, I have to really think about that one. It's usually I'm selling— tired would be one crack. It's like there's some— it's due to some— there's some cracks. Yeah. In the life. And, you know, depending on the situation, I really try to get them to think seriously about, but what if you took the time and made the effort to change some things in the business? Yeah. What could that open up for you and maybe not mean that you have to sell?

And then how do you help people answer the question of how much is enough? Because I have my process. I'm curious what yours looks like.

So there's two parts to it. There's the first part is going through an ideal life vision process. The second part, and our life strategist runs that process. She has a master's in spiritual psychology. She also has an MBA from UCLA Anderson. So kind of, you know, she She's well-versed and experienced in business and money, but also in spirit, spirituality. So the second part though, then, is now ideal life vision, then matched up with your financial structure to support that ideal life vision. And for that, which you're already aware of, we use a liabilities-driven asset allocation model to basically quantify the cost of all of your future liabilities, which is a terrible finance way to say to finance your ideal life and all the costs that are associated with it. And then we begin to say, okay, great, like, here's the cost of your ideal life. We could literally put an exact number on it. Now, it's exact for now, today, in this moment. We all know that your life is going to evolve and your ideal life vision is going to evolve, and therefore the financial structure has got to evolve along, right? With it. And then here's all the, you know, assets, both current and future, that you have to fund that ideal life. And you're either on track or off. And if you're off, now you have levers you can pull. And it's as simple as that. Or you can just keep moving forward without awareness of any of it. That's another option. But yeah, I'm being facetious, but of course I find value in doing the work.

No, I mean, I think the point that you're making here cannot be overstated, which is there is a number and it is knowable because almost everybody says they don't know the number or they pick a round number, right? I need $1 million or $10 million or $100 million or a billion.

The old back of the envelope math. Totally.

But there is a number and it's essentially how much does your ideal life cost? And then what's the gap, right? And now that's, I think, where values become so important. Because if I know what I value, now I can look at those trade-offs. Yeah. Okay, can I reduce my lifestyle and reduce that, that enough number? Or is it worth it to continue working and continue trading my time to try and get there at some point? And what am I— and what am I giving up to do that?

And now you're making clear decisions based on things that, that you know, and you're doing it with intention and, and awareness. Which is the best place to be making big decisions.

Totally right. And, and, you know, back to that, that original example. Yeah, the right answer might be sell today, but it might be, hey, if I work for 2 more years, I can sell for 2 to 5 times more than I have right now, and then I can spend the rest of my life traveling with my family or whatever it is. So there, there are times where it makes sense to continue down the path, right? But it's that, it's that intentionality, I think, that you're speaking to that really is important is what are the trade-offs? Let's name them clearly, and now we can make informed decisions.

Absolutely. And then another part of it is, you know, and you've had a lot of guests on this podcast that are way wealthier than I am and that have had the big exit experiences, right? So they, they can all speak to it better than I can and from a place that I haven't been. But I've seen and been a part of a lot of these big exit experiences, right? Whether it's clients or friends. And I'll never forget the first time, this was the first time that I was like, whoa, I did not really get it. This is several years ago now, but I was invited to a dinner and it was a bunch of really successful founders. I remember thinking like back to self-worth, I was like, I do not belong. I am the outlier in the room. I do not belong in this room. That's what I was, you know, telling myself on the inside. But I guess that's another story. But that dinner, everybody went around talking about how they're doing and how life has been post-exit. And I know that you're surrounded with a lot of people that you're close with that have had that experience. And every single one of them talked about going into depression after they sold. And when I say every single one, I'm talking every one of them. And I was like, wow, I I hadn't been around a ton of people who had exited, you know, 8 and 9-figure businesses until that dinner was the first time. The point is that that being such a common experience, I'm such a big proponent of, and I really try to push people like you do all, there's a lot of work that you can do before you exit that isn't just working on the business. It's what are your identities outside of the business? You might have to actually create them because you— there's probably a likelihood that you actually don't have them, but you can start building those. What are you going to post-exit as opposed to— for most people, it's like, I just want to get this thing off my hands and my life's going to open up. And that sounds logical, but then you get there and now you have like a lot of hard work to do because you can only travel around the world so many times before you're like, all right, sense of accomplishment, sense of purpose, all those things. So again, there's all that psychological, emotional work to be done pre-exit as well. So I mean, yeah, pre-exit. So I mean, that's a lot. Like, I get it. It's a lot.

It's a lot, but so necessary. Shifting gears back to my favorite question on this podcast. What does wealth mean to you now?

The easiest answer for me, it's one of my favorite stories because it's like one of them. It's just one of the most amazing feelings I've ever had in my life. I was coaching my son in T-ball again, something I dreamt about forever. When I first agreed to coach T-ball, I was at the coaches meeting and there all these guys were like, oh man, Coaching T-ball, I did that. It's like babysitting. Like, it's kind of a drag. Don't worry though, like, in a few years it's going to get a lot more fun. And, uh, and then I get into it and I'm like, I, I'm having like, I fucking love this. I did not have that experience. I was living the dream. We're playing a game, my son comes up to bat, and I'm the coach that's setting the tee on the— or the ball on the tee and getting the kids set up, every, every player. My son comes up and he just stands there in the batter's box, bat's down and just staring at me. I go, okay, buddy, time to hit, get ready and put the ball on the tee. And he just doesn't move. But he's looking at me in my eyes and it got awkward. And I'm like, buddy, what's wrong, dude? It's your time to hit. And he Dude, he looked at me and he— what— he took a couple steps toward me and he goes, "I love you, Daddy," and hugged me. And I was like— I felt like I was in heaven in that moment. I'm not even just saying that. Like, that's what wealth feels like to me. Sometimes I get lost in the fear and anxiety of money, and I can do that pretty easily. Because I'm human and I'm always going to be trying, you know, overcoming the stuff that, you know, those core wounds we talked about. But my best self remembers that that's what true wealth is for me. It's those moments. That's it. Simple as that.

Chris, what a beautiful way to end an amazing conversation. Thank you so much for showing up, giving us all of yourself here today. If people are interested, where can they find you and where can they check out what you're up to?

I mean, I haven't traditionally been active on the socials, but I am on Instagram. Chris Gearbays, just my name. FiveOceansAdvisors.com is our website. I think I'll just leave it at that, really. Thank you so much for having me. I hope to bring value, hopefully. Hopefully I did. But in either way, I love all the work that you're doing. I love having conversations like this. I could talk about this stuff all day. I just hope it's helpful for other people.

I can guarantee you that it will be that. And I appreciate you, man. Thanks for showing up.

Thank you.