Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you'll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.
Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Why Your Business Still Feels Like a Full-Time Job with Kenneth Kollasch
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Your business can’t keep running on instinct, caffeine, and chaos forever and if you’re feeling that strain right now, this conversation is for you. We sit down with Kenneth Kollasch, a certified business coach, third-generation entrepreneur, former franchise operator, and pastor, to talk about what it actually takes to grow a small business without surrendering your sanity.
We start with the surprising leadership lessons that show up long before you ever hire your first employee: the dinner table mindset of an entrepreneur family, the pressure and possibility that come with it, and how high-level soccer builds humility that most owners don’t learn until much later. Kenneth shares the moment his grandfather asked one simple question that changed everything, turning a near-pro soccer path into a values-driven choice about family, presence, and long-term purpose.
Then we get practical. Kenneth explains why doubling revenue doesn’t have to mean doubling your hours, and why “more volume” is usually the wrong answer when you’re already overwhelmed. We dig into the Small Business Flight Plan approach: diagnosing what’s real (not just what you feel), identifying win points to double down on, and fixing the pain points that quietly wreck marketing, sales, retention, and cash flow. If you’re a solopreneur, running a mom-and-pop shop, or building a small team, you’ll leave with a clearer framework for business systems, sustainable growth, and burnout prevention.
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Learn more about Kenneth: https://kennethcoaches.com/free
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Dinner Table Business Mindset
SPEAKER_00But uh one of my favorite things about growing up in a business owner household, which is something I talk to with clients today, is the dinner table. And it's one of my favorite memories of meeting my parents' consultants that they would bring in or having clients or even just the general topic of conversation just being about what we were wanting to achieve with our life. And it was just very intentional at the dinner table. And I loved like business was kind of the talk and not like SpongeBob or you know cartoons that I was interested in at the time. So yeah, growing up, it was very it opened my mind and it really opened my belief to what was possible. And I think that's my favorite thing about business owners and how they affect their kids. Of course, there's plenty of things I could say that I had to overcome and maybe weren't things I kept after I grew up. But uh yeah, it was a very unique way of growing up, that's for sure.
SPEAKER_01Welcome back to Plan Like a Boss. I'm your host, Tanya Lawson. And if you're a small business owner going crazy in the mom and pop stage of your business, you are going to love this episode. Today I'm here with Kenneth Culash, a certified business coach, third generation entrepreneur, former franchise operator, and pastor who knows exactly how exhausting it is to run a business on instinct, caffeine, and chaos. Through his 12-month program, The Small Business Flight Plan, Kenneth helps entrepreneurs install six proven systems and over 30 frameworks to finally enjoy the rewards they set out for. Time, money, and freedom. Kenneth, welcome to the show. I'm so happy to have you.
SPEAKER_00Yes, thank you, thank you. It's gonna be a great episode. I can already tell.
SPEAKER_01I I think so too. So start out by telling us your story because you have a very interesting story. Tell us how you got here.
SPEAKER_00Well, uh, they can stay subscribed if they think it really is interesting by the end. But yes, the story is essentially this. I am a third-generation entrepreneur. My grandpa came over from Mexico, and um, I love my grandparents and my parents. They've been amazing influences. They actually got me into soccer, hence the Mexico connection. And so my first path was pursuing professional soccer, and then I turned on uh uh that contract to uh be a stay-in-the-family business, marry my wife. We've been married 11 years as of four days ago, so fun times. And um from there, yeah, I was in the franchise world, the ballarm dance world for 14 years and uh started my first company in 2017 and haven't looked back. I've been consulting since then and officially uh became a certified business coach in my own agency just a couple of years ago.
SPEAKER_01Wow. That that's quite quite a feat, like from professional soccer to dance to you know, business. It's a lot. I love it. I love it. I think it's fabulous, and I think each of those probably affected the way you're able to react to things and run things in your discipline. Now, you spoke you're a third generation entrepreneur and your grandfather immigrated from Mexico. So you're a second generation child of immigrants.
SPEAKER_00Yes.
SPEAKER_01I th I think that will have something to do too with it too. But how did growing up in that kind of household differ from, say, your friends whose whose parents just, you know, worked for somebody else?
SPEAKER_00Yeah. Well, it was it was very different, I will put it that way. Um, and in in a way like everybody that has a, and we all do, a unique childhood, growing up experience going through school. Mine, I would say the most unique aspect of it was that I was raised with you can do anything, put you can do anything you put your mind to, you can accomplish all the dreams that you have, you know, that you set out for. And so it was a very hope and an inspirational kind of upbringing. And then there's, of course, some of the pressures of being successful, doing things faster than we did, doing things bigger than we did. Um, so that it's beautiful in both regards, you know, some points of contention as I was growing up. But uh, one of my favorite things about growing up in a business owner household, which is something I talk to with clients today, is the dinner table. And it's one of my favorite memories of meeting my parents' consultants that they would bring in or having clients or even just the general topic of conversation, just being about what we were wanting to achieve with our life. And it was just very intentional at the dinner table. And I loved like business was kind of the talk and not like SpongeBob or, you know, cartoons that I was interested in at the time. So yeah, growing up, it was very uh it opened my mind and it really opened my belief to what was possible. And I think that's my favorite thing about business owners and and how they affect their kids. Of course, there's plenty of things I could say that um I had to overcome and maybe weren't things I kept after I grew up. But uh, yeah, it was a very unique way of growing up, that's for sure.
SPEAKER_01No, I understand. My my dad was also an entrepreneur. And when I would go to friends' houses, money talk at the dinner table was completely off limits. I grew up in the South. I'm I'm in Tennessee, and and that was just that's not polite. We don't talk about money.
SPEAKER_00That's right.
SPEAKER_01But but we had a different experience at my house, and I'm guessing you did too.
From Soccer To Humility
SPEAKER_00A hundred percent. And and it's so funny. After, you know, we you know, you become teenagers and you you for some reason hate everything that's you know that you grew up with. But I remember a certain point where we were just like, can we please talk about something other than the cool new idea offer you had or the new pricing structure you're gonna roll out, or you know, this one amazing client and how much they love us. Like, we know, we know. But it's so funny, like that has shaped to your point earlier, that has shaped so much of I think why I care and love so much the work that I do now, because it is like, it's almost like I'm going back in time and I'm like using some of these stories and some of these things that at the time I despised, but now I'm like, wow, this is my parents were amazing. I should have listened a little more when I was at the dinner table. But yeah, so true. There are topics that came up around our dinner table that I know for a fact would never come up at my my friends' houses.
SPEAKER_01For sure, for sure. Now, you said you started pursuing professional soccer. How has that affected your career? Because I would imagine the discipline that it takes in that is going to affect you as a business owner.
SPEAKER_00Yeah, I think uh to your point that you made earlier as well. I mean, everything has a is a cause and effect, you know, and professional athletics for me, my grandpa, like I mentioned, is from Mexico City. He was my hero growing up, still is my hero today. We just went to a World Cup match um here in the States last month on Father's Day. So just the athletic world was what I grew up in and it's what I aspired to. I never planned on going to college. I said, if anything, I'm gonna be a professional soccer player or own a business. And um, and the the things that I didn't realize until after I got out of soccer that actually apply to literally things that I talk about with clients nowadays is what you talked about. It's not just the discipline, which I think the the main thing everyone goes to, but it's the ability to work with people and the ability to understand that my flaws affect everyone around me and my my inadequacies. What athletics did for me, soccer specifically, is it introduced humility way early on in my life. Whereas I know for some people that I've not only coached in my business coaching agency, but even friends and family and as a pastor, people I've met along the way, sometimes we just don't have an opportunity till later on in life to really experience the hard truth of humility. And I think that's the biggest asset that I gained from soccer was I ironically, you know, like, yes, there was a lot of accomplishments there, but humility is actually what I think I gained most from being in that environment for so long.
SPEAKER_01I love that. And you're so true. Um, as you know, professional musician here, lots of humility in music school through auditions and everything. And I think maybe that is something I I have a stack of rejection letters. Well, if I kept them, that would be this long. Yeah, right. But I think that humility, I think maybe it's even a little easier to stomach when you're younger, when you're a teen and in your early 20s, because you still have this I can do anything attitude that as you get older, if you've not really truly experienced failure, it hits a lot harder.
SPEAKER_00So true. And I think you're in that stage where maybe, and I know I can already hear some listeners out there that are kind of like, I don't think that's true. And let me position it this way the I think earlier on in our life we are far more open to humility or moments of humbling. The way we react to it is probably the worst. Um, but I think it's actually it's actually accessible for us earlier on, more accessible. But you're right, later on, we may have a more polite or PC or mature way, so to speak, on the surface level of responding to moments where we could be humbled. But I think we're less accessible, we're less open to actually being humbled. So even though it may look a little more polite on the surface, I think you're totally right. Our humility uh is far more accessible as a teen or as a young adult than it is when you're a seasoned veteran in your career or you have you've had your business for 10 years. And although you may respond more maturely, you're actually not maturing as uh in the aspect of humility or as open to it in those seasons.
SPEAKER_01Yes, I love that's so true. So, so true. Now, what now I have let's rewind because you had mentioned that you weren't gonna go to college, you were going to do a professional soccer or own your business. Did you go to college?
SPEAKER_00I did not. I stuck to my guns. Um, no, so funny story, this is hilarious. Uh maybe somebody out there can relate to this. I um I had a teacher and I was a senior in high school. I had done decent grades, you know, like average. And um, then when I was a senior, uh actually halfway through my junior year, I decided I started getting, you know, soccer opportunities. I had gone to Spain and the Netherlands to play some tournaments and just had gotten some opportunities that I started to
Skipping College And Learning Fast
SPEAKER_00realize, oh, I'm actually not gonna have to go to college if I don't want to, and started to get the chip on my shoulder and all that. And so I started to disregard school and getting get get like failing grades. And and my mom would always say, Kenneth, are you gonna are you gonna graduate? I just need you to graduate. You know, we need the GED. Um, and what's so funny is yes, I when I was going through school my senior year, I had a teacher that challenged me and said, Well, you'll never amount to anything. You know, the typical kind of like, you, you're just, you know, you're just a meathead, knows how to kick a ball and run around, but this is the real work in here. You should, you know, prepare for college because that's what's really gonna, you know, help you in life. And I got straight A's that semester, and then I went back to my normal routine just in spite to spite her. And it was so immature of me. But yes, I stuck to my guns. I didn't go to college probably because I didn't have the grades for it at that point. But I also had um I what I was looking for from soccer, I would need to go overseas for. And what I had access to with my family and the businesses we owned um was a better entry point into the marketplace than going to school and getting a hunting license that I call a degree. So yeah, no, I I ended up sticking to my guns and it, you know, it has its pros and cons.
SPEAKER_01No, no, I understand. My my dad didn't go to college either. As a matter of fact, he um had a GED. He had to drop out of school in eighth grade to actually get a job and help support his family. Wow. So so yeah, it was a different, totally different time period. Um but but yeah, I I think that's great. I think that's amazing. And I think it there's something to be said for college. I mean, I have three degrees, ten years. Yeah I finally paid off the student loans to to to prove it. Wow, well done. I I think there's something to to be said that it's not necessary for everyone. If you're gonna be a doctor, yeah, you need to go to college. But you can learn a lot, a lot more from just rolling up your sleeves and getting in the muck.
SPEAKER_00Yeah, and somebody that's that's as somebody that's hired, you know, people of all ages now for a decade, it's it's so true that there are aspects and there are positions and there are certain roles that absolutely scholastic education is necessary. Then there's other roles that the education is actually more valuable when it's kinesthetic or it's on uh hands-on or done with you, or it's just a different type of learning that is actually more beneficial than a scholastic, read a book, memorize something. So yeah, it is definitely industry and role specific. And I I'm not against colleges in any way, shape, or form either. But from my own journey, um, it's it's funny how it's I've been I've done all right without one. And so um, yeah, it's it's teach his own. Teach his own.
SPEAKER_01Absolutely, absolutely. Now, what made you decide, okay, soccer, we're we're gonna, we're
The Grandfather Question That Changed Everything
SPEAKER_01gonna leave soccer and we're gonna move into business.
SPEAKER_00So I'll take you back to I was at a MLS soccer game. I had just gotten a I had just gotten from the the connection I had. He was a college coach and his name was Adam, and he was working with me one-on-one because I refused to play at his college because I was wanting to go overseas. And he was training me one-on-one, and he connected me in the 2014 World Cup year, right before that. He had gotten the contract for me, and I was, you know, green light, green light to go to Brazil. And I'm at this MLS game, I'd taken my grandpa there, and we're sitting, you know, one row behind the players, and it's just the best time ever. Our team wins the game. We go to this Mexican restaurant right afterwards across the street, and I tell my grandpa the news. I'm like, grandpa, I finally did it. I had gotten injured a few years before. I worked my way back. I'm gonna play professional soccer. Like everything that I've that we've been talking about since I was three years old, like it's happening. And I remember him looking across the table, eating tamales. I remember him looking across the table and asking me, Kenneth, is that what you really want? And I was literally shocked. Like I was floored because I thought he was gonna cheer and we were gonna like take pictures with the whole restaurant, and it was just gonna be this, you know, uh cinematic moment. And um, I was so so floored. And I said, What do you mean? And he was like, We've always talked about, you know, this girl that you're, you know, you're engaged to, you want to be like a present dad and a present husband, and you want to be there for them. Do you realize that soccer? I mean, you're gonna be gone for 15 years, man. Like if you have a great career, you'll have the yes, resources will be there, but like you're gonna be gone or hurt or injured. And what are you gonna be like afterward? And you just helped me realize like what I really wanted. And so what really made me go from soccer back to staying stateside, marrying my wife, and um working in the family business and going the business dance route was all due to my my hero, my my hero at the time that really helped me realize like what I really wanted could be found in other vehicles. And maybe what I really wanted wasn't actually attainable in what I literally had worked for for 15 years. So um I uh it's one of the core principles I have is always have somebody there that's willing to tell you the truth. Hey, aka why I'm a coach, but um, always have someone in your life that'll that's willing to do that, even in your most excitable moments and your most climactic moments, still willing to tell you the truth. So true. So very true.
SPEAKER_01Now, let's talk just a little bit.
Doubling Growth Without Hustle
SPEAKER_01We're gonna move into hustle culture. Because your program, you promise owners that they're gonna double their business. In our current very anti-hustle culture world. Well, that's not true. There's still a lot of hustle culture out there. But doubling can sound like a threat to our sanity. How do we separate business growth from working twice as hard? Because over here on Playing Like the Boss, Playing Like a Boss, we are totally anti-hustle culture. I like to consider myself the anti-Alex Hermosy. No bro marketing over here, no working 24-7. How do we separate business growth from working twice as hard?
SPEAKER_00Yeah, well, fun fun fact, I actually I remember earlier on I had applied for a home hormosy job, and it was the opposite of what my ethos was. I was like, please, dear God, no, this is not. And it and it's not what I have.
SPEAKER_01The studio editor also applied to work for the hermoses. So yes.
SPEAKER_00Really? There you go. There you go. Uh and yes, and there is success to be found in the literal opposite paradigm. So what I will say is so for my, it's so true that um we want the results of X, Y, or Z. Most people, it is doubling their business. You know, we always think if I were to be, if I were to have everything I wanted, I'd be twice as rich, or I'd have twice as many clients, or I'd have twice as twice as uh um, you know, uh prime primo clients. You know, my client actual quality would be double what it currently is. And how we get there, or I should say this, why we want to get there or what we want to achieve isn't normally the problem. Sometimes it's exaggerated and you need to like cool your jets and come back to reality. But for most people, it's realistic, you know, to double their business. But how they get there is normally uh, like to your point, it is hustle, it is volume, it is um essentially taking what's already not working well, or in terms of your stress levels like driving you crazy. Take what you're doing that's driving you crazy, and let's just do more of that. And volume is not the solution to most people's destination goals. So, yes, with my small business flight plan, it is far more about um optimizing and actually sometimes revolutionizing their actual business systems from leadership and sales and marketing all the way to the way they do productivity management and cash flow maintenance. Literally, we reinvent and revolutionize their business systems so that way the business itself is what's improving, not necessarily um the their personal volume and the metrics and the I've got to stay up late and wake up early. And um, so we solve a lot of the quantity problems by introducing better quality into the actual way that they operate their business.
SPEAKER_01Got it, got it. Yes, 100% for sure. I hustled my way into burnout and and then later cancer. And let me tell you, we we don't do that anymore. Man, it's awful. Um now we've we've touched on soccer, we've touched on business, you're also a pastor. How does your faith and your pastoral background shape how you view business and how you work with people?
SPEAKER_00Yeah, well, it is uh it is one of the things that I struggle with for the longest period of time. You know, I am an all-in kind of person. Uh, I think every entrepreneur can relate to that at least a little bit. And for me, I remember going between, you know, my business career and then I would go and, you know, jump headfirst into what I call the professional
Faith Values And Self Sabotage
SPEAKER_00Christian world. You know, I'm a professional Christian. Basically, I, you know, I'm on staff in some kind of church. And um I just I there were things that I absolutely loved about being a pastor, the ability to uh affect the, the, the core aspect of people's lives and the goodness that that would bring for them. But then I also saw, you know, amazing things happening from in the business side of things were people's resources and their stress levels and the way that they um hoped and dreamed for their family and their life. That was improving and that was so amazing. And so for me, the things that were a part of the pastoral world that I loved and the, of course, the natural upbringing and the experiences that I had in the business world, um, that's what led me to doing what I do now, the business consulting. Because I feel like it's the perfect mixture of I, of course, get to help people understand how to grow their business better without necessarily going crazy and losing their sanity. But also on the pastoral side of it, what I love in the business coaching that I get to bring from there is the fact that someone's business can only succeed as much as their own personal, um, their own personal ethos will will allow them to. I've seen so many businesses that are successful and then the owner self-sabotages because of things that you're talking about on this show, like burnout and and hustle culture and really just sacrificing their value system for growth in their business. So I love bringing the personal, uh, spiritual, the emotional and mental development side to the owner or to the specific leadership team, the individuals, so that way they themselves are better people to build a better business.
SPEAKER_01Love that. Yes. And sometimes it's hard. Sometimes it's hard. I I am I'm incredibly religious. And even yesterday, I was working on some stuff and in the middle of it, and I was like, no, I need to finish this. I'm like, no, you're gonna stop, you're gonna put this down, you're gonna go to adoration because today is your day to go to adoration. Go. And and I did, and it was so worth it because it just it totally recentered me.
SPEAKER_00Yeah.
SPEAKER_01Now, let's say that you are working with a a solopreneur or an entrepreneur with a very small team that wants to expand their business. Um, how do you approach coaching someone like that?
SPEAKER_00Yeah. So I would say most people uh in that stage, I consider them still in the startup phase. Basically, if you're anything under 200,000, 150,000, even if you've been in business five years, I still consider that the ramp up, the startup phase. Um and for most startups, what the what what we mainly will do is what we do with a lot of um established companies as well. Uh the best place to start is always knowing where you're at. And it's not just uh, I'll put it this way most solopreneurs and most startups, they're very instinctual. A lot of the way that they make decisions about their business is feeling oriented. Well, I feel like we're getting a lot of great leads, or I feel like the client's doing really well, or I feel like our retention rates are great, or our conversion rates are, you know, so on and so forth. We got a great offer. Um, but actually ignoring the ability for you to measure and track and actually analyze real data, that is normally the starting place where we help them create a diagnostic system where they can actually have real feedback on what's going on in their business, not just how they feel about it or what you know their gut says, although there's value to that. And then the second stage is of course identifying their biggest um their biggest. Biggest win points and then their biggest pain points. And when I say win points, I mean if there's something that's
Coaching Framework For Small Teams
SPEAKER_00going really well and it's like a strength or a key point in their business that is attracting more clients or making the client value, lifetime value bigger, greater, longer. Um, those things we want to double down on. Like if I knew that, you know, the the ball was going to land on 15 red every time, I would just keep doubling down. Like let's let's keep rack racking this thing up. Um, so we want to double down on their wins and we identify that first because normally those are the easiest to find and they're uh the safest emotionally to start with. And then of course we get to the pain points where it's like, okay, these things are actually undermining your success. They're making people want to quit your services, they're making people want to not, you know, uh start your service to begin with. And so then at that point, we help them actually address the things that are either missing or they're intentionally ruining the customer experience or ruining their lead generation, all those kinds of kinds of things. So we go from diagnostic stage to addressing their wins and then improving their pain points. And those are the three main phases that get them, when they when they've gone through those three, it gets them out of the startup phase where they're passing that 100,000 for the first time or they're finally hiring their first few um managers or their tenth employee. They're getting out of that small team solopreneur stage.
SPEAKER_01Got it. Yeah, and I love how you you brought up the feels. I feel this, I feel that. And I think that comes from as an entrepreneur, we become very attached to our business. It is our baby. And you're right, that intuition is important, but the numbers don't lie. But sometimes actually putting those numbers on paper or in a system and looking at them, that's scary. Because it shows you what's not working, and you don't want to see that. You want to just look at all the sunshine and roses. Like you said when you were playing soccer, you know, you you get humbled very quickly that way. And and it's hard. It's very hard. So I love that you you start by attacking their wins. You know, I'm I'm a I'm a teacher, I a music teacher. And a lot of times with my students, especially the young ones, we we struggle with how to give feedback. And uh one student I loved him, we we worked so hard on the compliment sandwich. Something nice. Oh, yes. Insert the criticism, follow up with something nice. And I feel like that's what you're doing. And you're it's it's like a different version of the compliment sandwich. This is what we're winning on. Let's double down on. Yeah, let's look at this. I love that. That's fabulous.
SPEAKER_00So true.
SPEAKER_01Now, if you could go back to your younger self when you're first starting out, you're deciding, am I gonna go, you know, soccer or am I gonna go business? Because there are a lot of people out there listening right now who who may be struggling with something like that, but maybe not professional soccer, but maybe it's like, do I do I go into corporate or do I really want to get out on my own? What is one piece of advice that you think you would give your old self?
SPEAKER_00My gosh, what is it? What is it, Tanya? I have no idea. No, I I I I have often often, I will just say this, I have res I resonate and I have also battled with returning to my past success. And I think um, you know, from my perspective, God takes us through the seasons at the right time, even if they don't feel like the most comfortable thing in the moment, you know, the the the wilderness had its purpose, the promised land has its purpose, the the dry sea, crossing the Red Sea has its purpose. You know, there's moments in time that feel like it's out of order. And so I I would say if I gave myself advice back in the day, not that I regret um most of the decisions that I made along the way, um, but I think the advice I would give myself, even though I did this a little bit, I could have done this so much more and it would have saved me so much pain. And and then the ruminating and staying, you know, and not being able to sleep because I'm just, you know, there's that core decision I keep second guessing myself. I would have leaned so much heavier into the one or two people that I trust, like my grandpa or my wife, or I've I've always also had, you know, business mentors and coaches
Advice On Big Life Decisions
SPEAKER_00along the way. And I would have, I would have leaned way more into people like that than just, again, trust in the field. Well, I just I feel like I was better at that. And it's really my insecurity getting the better of my emotions. And um, I would have leaned into people that didn't have the insecurity that I had or didn't have the emotional um connection to the situation like I did. And I would have leaned more into people like that, whether they were older or younger, but just the people that I could trust to give me a real, um, a real perspective from the outside that I could, you know, incorporate into my decision making. That would have definitely helped me out when I was younger.
SPEAKER_01That is that's really profound. That's really beautiful. Because you're right, especially all of us when we're younger, we we think we can do it all. And we forget that they're the older people, and they may not even be that much older, they've done it already. Yeah. And they can offer a wealth of advice. So I love that. So how can listeners find you if if they're interested in your systems or your your compliment sandwich coaching business? I I just renamed it for you, by the way.
SPEAKER_00There we go, there we go. From now on, it is the compliment sandwich coaching. Um, yeah, no, I've made it really easy. You go to Kenneth Coaches.com slash free, and I literally have a whole resource market, a free resource market that if you want to generate your first hundred thousand or your next hundred thousand, it is over a dozen free resources that I honestly don't make any money from. So it's some of them are third party, some of them are mine. And um you go to Kennethcoaches.com slash free. You're gonna throw in your email and you're gonna get access to all of it. You can download all of it right from uh KennethCoaches.com slash free.
SPEAKER_01Uh thank you so much. We will make sure to put that in the show notes. So listen to what Kenneth said and and really bring from the story. Yes, you need to trust your intuition, but you also need to rely on people you trust. So make sure you're thinking about that before your next big business decision. And until next time, keep planning like a boss.