The Success Architect
Success doesn’t happen by accident — it’s designed, built, and reinforced brick-by-brick. On The Success Architect, builder and business strategist, Jake Lewendal brings a craftsman’s mindset to personal growth, wealth, and high-performance leadership.
With raw honesty and practical frameworks, Jake breaks down the systems, habits, and decision-making principles that separate the overwhelmed from the unstoppable. From building multi-million-dollar companies to coaching ambitious people, Jake’s philosophy is simple: success is a structure, and every person can learn to build it.
Each episode blends actionable strategy with real-world conversations featuring high-impact, career-driven entrepreneurs and operators who are building lives of purpose, discipline, and momentum.
This is for the ones who build. The ones who take responsibility. The ones who know they’re meant for more — and are ready to architect a life of depth, strength, and true success.
The Success Architect
What You Tolerate, You Authorize
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Jake Lewendal was twenty-six years old when an employee sat him down and told him something no one else ever had: he didn't do what he said he was going to do. And the employee was right. In this episode, Jake goes back to that moment — a career conversation on a bar patio that turned into the most honest feedback he'd ever received — and traces how a habit of overpromising quietly ran through his whole life, not just his business.
Jake doesn't soften it. He admits he made promises to employees and friends because it felt good to say yes in the moment, then let something else "come up" every time. He's candid about the version of the story that would look better — that he was making noble sacrifices for a growing company — and rejects it outright: at the time, he was simply on the grind, and he refuses to backdate a better excuse than the one that's true.
The episode turns from confession to method: how a self-described people-pleaser actually broke the habit — not through willpower or a moment of revelation, but through logistics. Jake explains how he learned to let his calendar say no for him until the reps built the character shift he couldn't will into existence.
What started as a hard truth from a young employee became a pillar of how Jake runs his company today: do what you say you're going to do. He closes by returning to that moment on the patio — and the realization that the one person who told him the truth almost certainly wasn't the only one who'd noticed.
Welcome to the Success Architect, where we don't just build homes, we build legacies. I'm your host, Jake Lewendal, custom home builder and coach. Each week, I sit down with builders and entrepreneurs who are ready to 10x their business, their health, and their mindset. This is where blueprints become breakthroughs. Let's get to work. Alright, this one is called What You Tolerate, You Authorize. And this one has another cold open. I was 26 year old when an employee sat me down and told me that I don't do what I say I'm going to do. And he was absolutely right. It's been 12 or 15 years since I was told this. And I still think about it today. And it's so interesting because this employee of mine, he was wise beyond his years. He was a couple years older than I was. I don't think he really had any idea what he was doing, but he actually changed the entire way I run my company and the entire way that I run my life. When I was 26 years old, it was my first, I guess it was my second company, but it was my first building company. And I ran mostly the office and administration and sales side. I was running a real estate business alongside of this. So I ran all the office, I ran the administration, I did all the books, all that stuff. And my partner, my father-in-law, you probably heard about in a past episode, ran most of the on-site staff. And what was kind of shitty and is my fault and kind of a conversation for another time is that I wanted to be more involved in the field. I wanted to have more input. I had knowledge there, and really I kind of felt shunned out of that side of the business, which is a story on its own and is my fault because I was very passive about it and I allowed it to happen. But this was somewhat of an issue. And I wanted it to change. So things that happened where I felt like I could be a little bit more a part of that side of the business was when I would talk to our employees who are out in the field. And one way that I felt like I could be a little more part of the business was if I went out and helped them do X, if they had something in the day, if they had a question that I could help with. And I found myself promising a lot of things that I didn't follow through on. I would promise that I would make a call to get them something, or I promise that I would actually show up to help them with something. And at the time, I did it a lot because it felt really good to say it. Like, yeah, I'm gonna be there. I will help you. It felt great in the moment. But again, not an excuse. I was running a real estate company as well, alongside this business, this building business, and something would always come up. And I was young, was not that smart. And a lot of the times, like I would just bail and I wouldn't even call them. It would be something small enough that it wasn't really gonna change their day. And uh, but I just straight up wasn't showing up when I said I was going to. Actually, really great dude. He stuck with us. He was with us probably for four or uh maybe four years in the business. And uh I had gone to talk with Zach about some things for the employees, how he could grow in the company specifically, and benefits that we were talking about for the employees, and he had some opinions and he wanted to tell me about them. So it was it was kind of it was a career conversation for him, and it was meant to be a great conversation. We were actually at the bar across from Hawthorne School downtown in Bozeman on the upper patio, and I remember even like we were sitting at the little bar area that faces Hawthorne, and Zach looks at me and he goes, Hey, can I give you some feedback? I was like, Yeah, absolutely. Like, sure, I'm really great at taking feedback. And he goes, you know, the other employees see it too. He goes, but you don't do what you say you're gonna do. And I was absolutely stunned. And I and I said, What? Like, I I mean, I was I was stunned because like I was indoctrinated growing up with like you don't lie, you tell the truth, like you do what you say you're gonna do. You show up when you say you're gonna show up. Not doing that is lying. And being told that by this guy, like it just blew my mind. And he kept going after that. I don't know, I don't know what the look on my face was, but he kept going. He was like, You're constantly saying that you're gonna do something for us, or you'll show up and help us something. He was like, You've done it to me multiple times, and a bunch of the other guys have mentioned that you've done the same thing. And like it stung so bad. And he goes, you know, hey, this is not like he goes, I'm just letting you know it's actually not a big deal because, like I said, every single one of these things was a small thing. But he was like, I just want to let you know. It was a complete freaking kick in the nuts. And now, luckily sooner than now, I looked back on it and I was so thankful that he was honest with me. I don't know if Zach actually still lives in Bozeman, but like he was one of the most honest guys and also very direct guys that that I've ever met. He was very quiet, but he was very direct. He said how, said what he was thinking, and I am so thankful that he did and gave me that honest feedback. And it was just so interesting that he was like, hey, you know, it's not a big deal. I just wanted to let you know. But that like was that's the part that got me. Like it wasn't even, he wasn't being rude, it wasn't a confrontation, and he wasn't even mad. He was just quietly adjusting me. And I don't even know if he knew he was doing it, but it stuck with me. From then on, I started seeing it in a lot of places, and it's not comfortable to say this because it's it probably lost me friends. Like I did it a lot across my whole life. I I said yes to going to dinner with friends when I was younger. And this is this is like I can remember back to doing this with friends from when I was like maybe 19, 20 years old. Uh, I I was working a lot, I had an entrepreneurial mindset, but I would say yes to going to dinner with going to dinner with friends, and then I would bail five minutes before um with employees. I would do it on occasion. And the interesting thing though was that I almost never did this in the real estate business. I only did it in the building business, and the building business at the time was not my main income producer. And that was a real thing. The fact that it was not the main place where money was coming from. It was a smaller business, and I found myself essentially lying to others and lying to myself in that business more often than the one that made money. And what's kind of shitty is like I started to hear it from people close to me. My sister, I think I even had a couple of my parents' friends tell me that I only show up when money is involved. And what sucks is that from the outside that's exactly what it looked like. The pattern that I found, though, was that I never heard that statement from someone who owned a business. I heard it from some family members, not my parents, interestingly, and they own businesses. I heard it from a couple employees, and I heard it from some friends. None of them were in the process of building something. And please understand this is not an excuse. It's just a pattern that I started to see and I want to call out. I hear, and I'm sure you guys have heard on a lot of Instagram memes, podcasts, everywhere, that entrepreneurs and people, anybody who's building something, you don't have to be an entrepreneur, you can be an entrepreneur, like anyone who is building anything will go through stages in their life, and unfortunately, they will probably lose friends and lose relationships as they grow. This can happen with money, which is what I'm talking about here. This can also happen with personal growth. And that's why I'm saying this is not just for entrepreneurs, this is for every single person in the world. When we start to grow personally, let's take, for example, in our body, maybe. Maybe we have friends who are not super fit and don't like to get out and do activities outside. And one day, let's say I decide that I want to get fit, that I'm sick of being too tired to go on a hike, or sick of only making it a mile on the hike and have to turn around. And I start to make some changes in my life. But my friend group doesn't make those changes. Most likely I'm gonna go through a lot of scrutiny with that friend group to the point that it's possible I may even lose those friends. And that is growth. And I'm not saying that happens every time. I'm not saying that this, that every human acts that way. It's just a pattern that I have seen throughout life that does not only uh focus on money. Now, that being said, when it comes back to where I was and the fact that I was not doing what I said I was going to do, let's be really honest, I was not making noble sacrifices. I guess I had other families who relied on me in our business. You know, actually, I think our construction business employed seven guys at that time. So their families did rely on us to have work, to have all this stuff. But those little white lives did not seem to change anything. And so I kept doing them. But I was on the grind. I happened to be focusing where the money was taking me, and that was the real estate business at the time, and that's just the truth. So, what could I have done better? I could have communicated, I could have been honest. And at that time, I was a people pleaser and I hated hard conversations, especially more like personal ones. I was able to have hard conversations in real estate. I was able to have hard conversations about money with people who I didn't really know. But when it came to people who I cared about, who were a piece of my life in some way beyond maybe meeting them, you know, two weeks ago and doing a business deal with them or a real estate deal with them where we only know each other for 45 days, I had trouble with the confrontation. And so I'd tell them what they wanted to hear to their face, and then I wouldn't show up. So what's different now? Today, at the moment, there are arguably more, but between 10 and 12 families that depend on this business to be run well, to be successful, and to continue to pay them. And there's real weight. And that does make decisions harder. That makes no something that has to be said on occasion, but something that I do better now is saying it on the front end and actually communicating it. Now that is not an excuse, and I'm not backdating that excuse for that time in my life, because at that time I was saying yes to people's faces, and then just not showing up. So where's the pattern? Where's the habit? And how did I break it? So, first I'm gonna talk about more the logistical way of breaking this habit, and then I can talk about more of the internal way that I broke this habit. Hold here for one moment. Okay, go back to the section about the habit. So let's talk about the habit and how I broke the habit. Now there's a pattern underneath all of this. And for me, it was that I wanted to be liked. I was a yes man, I was a people pleaser. And that's how it first started. Once I slowly started to move out of that, at least just a little bit, I actually started to think that I could fit it all in. And I wasn't lying to people because I became cognizant of this issue, especially after Zach called me out on it. And but did it change my habits? Unfortunately, not a hundred percent. It made me very aware of it, but I started then saying yes, actually thinking I could fit it all into my calendar. And I did for a while. I was young then, I did not have kids. I I mean, this actually happened, I think, before I was married, um, or right after I was married. And I actually thought I could fit it all in. And the interesting part is that second one, fitting it all in, has followed me until recently. I can run it a hundred percent. And yes, does it take away my home life, other parts of my life a hundred percent? But I always was a yes man and wanted to fit it all in, and that is my flaw, being a yes man. Not being willing to say no when everything in me knows the answer is no. And like, so simple. I was literally watching a bluey episode with my daughter the other day, and the mom says, Does your outside voice say yes when your inside voice means no? And that's who I used to be. Is my inside voice being saying? No, but I would say yes on the outside because I wanted to be liked. And I took me a long time to get sick of my own behavior. Like that turns into not a scheduling problem, that turns into a character problem very quickly, and that's what it was. It was a character problem. And so fixing the character flaw is a much bigger undertaking than fixing the scheduling flaw. And the hard part is when someone gets called out on this, just like saying that I'm gonna change it doesn't mean it'll actually change. So, what did change it for me? What actually modified my habit? For me, it was Warrior Week. Now, I'm gonna do a whole episode on Warrior Week and what I learned here. But the point is, is that I was looking for a hundred percent character inversion. I was sick of my own shit. I was sick of how I was acting, and I was sick of how I was treating other people. And I was looking to find the side of me that could actually say on the outside what I was feeling on the inside. Now, for the guy who doesn't exactly want to go to Warrior Week, which in the episode where I talk about Warrior Week, I'm not gonna give away enough because sometimes when I tell too much, people don't want to go. And I would highly recommend that program to almost any man out there. It's amazing. But let's say if someone needs a way to start logistically changing the yes man behavior instead of changing the character first, we can change the logistics because willpower is not going to fix this issue. Logistics actually can help start to fix this issue. And the easiest thing is actually stop before you say yes. When someone asks me something now, I literally live and die by my calendar. And it took me a hell of a long time to actually work in, work into living and dying by my calendar. And it's one of the best things that's ever happened to me because the calendar doesn't lie. I mean, math, numbers, like they don't lie. Time doesn't lie. So actually stop, look at your calendar. And then a great thing is that you can blame your calendar. Say no because you genuinely can't fit it in. And that's a logistical issue, and you can be honest about it. And you can let the calendar be the bad guy while you work on building that muscle in your character and actually using your internal no and saying it out loud. Now, I mean, why does it work? Because when I've talked about unconscious programming in this podcast just a little bit. And interestingly enough, logistics and doing something over and over again actually starts changing our unconscious. The logistics can actually start to change our character because we're getting reps saying no. And it gets easier and easier every time. So where am I now in life? First question is, is can I fit it in? And if the answer is yes, then the second question is, do I want to fit it in? And that is a very new thing for me that I have just started to figure out is only fitting in what I want to fit in. Not just what will fit in. Men, you know as well as I do, sometimes the only way we actually change something is the logistical route. And the reason I'm talking to men is because I'll be honest, it seems to me that women are much better at these character changes than men are. Maybe that's an unfair statement, but sometimes it's way easier to use the logistics in order to start making a character change. There's no feeling in it. And that's how a lot of us are wired. We get worried that if we say no, we're gonna hurt someone's feelings. But if we fall into a system, then sometimes the revelation of the character change shows up by itself. For me, I couldn't say no. So I started to let my calendar say it for me, and the reps started to work. So, what has this become for me? Doing what I say I'm gonna do has become a pillar in my company. It's literally a part of our core values in our company because it is so freaking important. And it's taken me years of self-reflection and years of practicing to learn to say no. And I still fuck it up sometimes. There's actually like my family is one place where I'm terrible at saying no, but I've started to get a lot better at it. Like, there's places in my life where I know it is very hard for me to say no, so I specifically focus on it when I know that time is coming. But what this gave me, and what this multi, multi, multi-year lesson has given me, is that I see it everywhere. When someone says yes and they don't show up, it's so glaringly obvious to me instantly. And to me, maybe it's a little unfair, is I see it as a character flaw because that's what it is. And granted, some people screw up, it's okay if we screw up, but if we do it multiple times, it's a character flaw and it's something that needs to be called out and worked on. How do I handle it when I see it, especially in my company? First time is empathy. Usually, even the second or third time, I still have empathy for it and I mention it. But at some point, it can only go so far. People who don't do what they say they're going to do not get to stay in my circle, and that's just how it is. It is an absolutely a character issue, but the great thing is that's a changeable one, and I'm proof of that. If there's someone who is willing to work on that, then there is room for them in my circle. But if they're not willing to work on it, then they do not get to be here and around in my circle. Everyone in momentum, I want them to be living the identity of momentum. One foot in, one foot out is not okay here. And not in my circle, not in my company, not in my family. Like everyone around me needs to be on the other side of the fence and do what they say they're going to do. And that is not only is it easy to spot, but that is just a fact, and that's how we all get along, and that's how we all help each other. And that's the whole point of it. Now, I could have stayed on the path of this bullshit of saying yes when I actually mean no, but I didn't. I took a stance and I'm absolutely still taking it. If Zach walked into my office right now, I would give him a massive handshake and hug and thank him for calling me out. Because up until that point, I could not believe I had not been called out by somebody else. Somebody way closer to me absolutely should have called me out, and they didn't. Now, after Zach, I actually did get called out a couple times by a couple people, specifically friends. And that one hurt, but that's just how it was. I had no idea that one sentence, one question, one little piece of feedback was going to change my life. But I'm so glad that an honest guy was being honest about something that was bothering him. Granted, he was one of the only ones who told me, but I know that he wasn't the only one who noticed it. Thanks for tuning in to the Success Architect. If today's episode helped you lay a stronger foundation for your business or your life, subscribe and share it with someone ready to do the same with theirs. You can follow me, Jake Lewendah, on social for daily tips on health, wealth, and building success that lasts. Until next time, keep designing, keep building, and keep leveling up.