The 3 Financial Mistakes Ambitious Founders Make

Are you making great money… but still not building real wealth? You’re not alone.

In this episode, I chat with Kaitlyn Carlson, former Wall Street wealth manager and founder of Theory Planning Partners, who helps 7-figure female entrepreneurs build financial legacies—not just businesses.

This isn’t your typical finance convo. We’re breaking down:

✨ Why high income doesn’t equal financial freedom

✨ Mindset blocks that keep you stuck, even at 7 figures

✨ How childhood money dynamics impact your business

✨ Why you need a wealth team, not just a bookkeeper

Kaitlyn shares practical strategies and powerful shifts to help you move from hustle to legacy—and finally keep more of what you earn.

Whether you’re making $500K or $5M, this conversation will help you rethink how you lead, earn, and build a future on your terms.

Click play to hear all of this and:

[03:44] Why most 7-figure entrepreneurs focus on income but ignore long-term wealth

[08:19] The financial wake-up call that led Kaitlyn to serve female founders

[11:11] How childhood experiences shape your financial mindset

[16:05] The key differences between an income strategy and a wealth strategy

[23:45] Why building wealth requires a team (and not just a bookkeeper!)

[29:32] How to evaluate if your business is scalable, sellable, or sustainable

[37:51] The mental shift that changes everything: from “I have enough” to “I’m enough”

Listen to Related Episodes:

• Tax Secrets Every Entrepreneur Should Know with Karlton Dennis
• 8 Mindset Shifts to Transform Your Relationship with Money
• Wealth Building Strategies: How to Budget, Invest, and Raise Your Prices

Connect With Kaitlyn Carlson:

Instagram: https://www.instagram.com/theoryplanningpartners

Facebook: https://www.facebook.com/profile.php?id=100090129347132

Website: https://theoryplanning.com/

📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader: https://jasminestar.com/newsletter 📧

For full show notes, visit jasminestar.com/podcast/episode620

Transcript

Jasmine Star 00:00:00  Welcome to the Jasmine Star Show. Just before the cameras turned on, we realized that somewhere behind the scenes, we've calculated the archive. And this is episode 620. And I couldn't be more excited and honored to have a conversation about my favorite thing. Money. Today we're going to be having a conversation around the differences between making money, aka riches and turning it into wealth. The difference is between how we look at money and the potential for it, and how to strategically use your money to build something that's bigger than you, that gives you options, that allows you to step into the things that you want to when you want to do it. And I'm speaking this as like a first person narrative. I had a conversation with our guest today and we immediately hopped on. It was we made an introduction. It took us a couple of months to get together, and the minute we got onto the zoom call, within five minutes, I was about to, like, braid her hair right? Kit in her yearbook, send her friendship bracelet and say, like, pack me up in your bags.

Jasmine Star 00:00:54  We're going to be friends for life. I actually was almost this close to her spooning her and said, you. I will put you in my pocket. You cannot leave me for the rest of my life. And then all of a sudden I decided instead to ask her on my podcast and share her brilliance with you. Welcome to the show, Caitlin Carson.

Kaitlyn Carlson 00:01:08  Thank you. I also have you here. That was quite the introduction. Well, good.

Jasmine Star 00:01:11  It would be quite the introduction if it wasn't entirely true, because it's now it's a series of facts.

Kaitlyn Carlson 00:01:15  Yes.

Jasmine Star 00:01:16  You're incredible.

Kaitlyn Carlson 00:01:17  Thank you.

Jasmine Star 00:01:17  Thank you for being here. And let's keep the main thing. The main thing. I love when people have optionality. And optionality was explained to me, is you're not forced to do something. You get to choose to do something. But so many of us are forced into doing something because we don't have options. We go to the job that we know, we stay in the house, that we know we date the same person that we know.

Jasmine Star 00:01:39  And a tool that I've learned as I've gotten older and as my business has gotten bigger, is that optionality comes when we have made strategic decisions at one point in our life to pursue a different result. One example would be I didn't start with money. I didn't grow up with money. I created a business that slowly over time. Like my first was like my dream was I could make $10,000 a month. My life would change. And then it turned into, if I could make $100,000 a month, my life would change. We did $1 million in a year. My life would change if we did $1 million in a month. And then with every subsequent milestone, it didn't ever seem like enough. It just seemed like I had to work more to get more. And then I meet people like you who opened my mind and say, hey, Jasmine, it seems like you're climbing a ladder and you're acquiring stuff and your lifestyle gets nicer and the cars you get nicer and the trips get nicer. But are you working to stay on the treadmill? And you and I had a conversation, and that's where I want to start this conversation.

Jasmine Star 00:02:38  And that is first things first, somebody is watching. What is your belief around money and turning it into wealth? They're listening right now. They're like, I'm not sure I want to listen. Let's give them a little amuse bouche around what they can expect.

Kaitlyn Carlson 00:02:51  Okay. The example that comes to mind immediately is the Range Rover. So when I started theory and I first started getting into the online space, for some reason, the big thing was everybody wanted a Range Rover. And I remember giving this example that if you had a great launch and you made $100,000 and you really wanted a Range Rover, took that $100,000 to the car dealership, you bought the Range Rover right then and there. You would end the life of that dollar if you took that same $100,000, invested it in a portfolio, and use the income off of that portfolio to pay the finance payments for that Range Rover, you could end up buying Range Rovers for life rather than just buying that one Range Rover. That regenerative framework is the bedrock of wealth creation.

Kaitlyn Carlson 00:03:46  And that is not something that is taught to us in our education system. But it is vital to Understanding how, just like the soil, if you give to the soil, the soil gives back to you. It's the same thing with money.

Jasmine Star 00:04:02  Okay, so what I heard was I'm going to buy a Range Rover as the rest of my life, because the conversations that I have with you. Thank you. But at the same time, in all in all seriousness, you know, I started my business and I started my career not ever really knowing what it could turn into. And so I think that I became very much like a statistic of the things that you talk about. So I come from a first generation family. We didn't have much at all. And so when you come in to money, it's a it's a language that nobody in my lineage has ever spoken. And so you're kind of like self servicing. Like, what do I do with money? How do I invest money? And I think that if I look back and I, I would say if I was kind to myself, good job you did the best you could with what you had.

Jasmine Star 00:04:43  But generally there was so many lacking points. So what I want to do is I want to have a conversation around wherever somebody is right now, whatever age they are. If you are making money in your business, not. I'm trying to get it off the ground. This is for somebody who has a little bit of money in their business. What are the three common mistakes that I want to go through? So a lot of people listening. We have a six figure founder, seven figure founder, eight figure founder. It's like, what are the common mistakes that people who are building that upper six figure life, what are those three common mistakes? Seven figure. What are those three common mistakes and eight figure because you you work with this wide gamut, mostly seven and eight, but the gamut of like, how do we get past that next thing and build towards optionality.

Kaitlyn Carlson 00:05:21  So what you're describing is, is the fact that you're not operating off of a holistic vision, right? It's so entrepreneurs especially, but everybody, most people live their life putting one foot in front of the other, right? And not really looking up.

Kaitlyn Carlson 00:05:38  The important thing that we need to do is take a step back and think about, what do I want my life to look like when I am lying on my deathbed? I want to be thinking, wow, that was beautiful. I did everything I came here to do and I did it my way so often. Were so busy that we never take the time to step back and ask what we really want our life to look like, so we need to start with that. And the greatest thing about that exercise is that it's free and you can do it at any time. And there's so much information that lives in that vision. And so when I describe the wealth creation journey, I often describe it like we're going to be hiking and descending a mountain together over the course of your lifetime. In order to go on that journey together, we need to answer three questions. Where do we know? Where do we want to go and how do we want to get there? No matter where you are, whether you're at six, seven, or eight figures, those are the basic questions that everybody should be asking.

Kaitlyn Carlson 00:06:45  So where are we now? From a wealth perspective, we need to set up base camp right and figure out like where are we starting from? So in terms of wealth, that's figuring out what is my net worth statement, what are my assets minus my liabilities, that's going to give me my net worth. The second piece is cash flow. What does it cost for me to live my lifestyle? Is it $10,000 a month? Is it $20,000 a month? Is it $40,000 a month? I can tell you 99% of people come into us not really knowing what the answer is to that question.

Jasmine Star 00:07:19  And I want to pause here just for a point of clarification, is like the vast majority of people who are coming to you already have seven and eight figure businesses. So you're saying that 90% of these people who built these massive, successful, statistically near impossible businesses don't know what the monthly expenses are?

Kaitlyn Carlson 00:07:35  Yes.

Jasmine Star 00:07:36  And so if somebody's listening and they're probably like, well, I'm not sure I know what mine are.

Jasmine Star 00:07:40  First up, what do they do?

Kaitlyn Carlson 00:07:43  Go to your credit card statements. Look at there's actually a great app called monarch. Monarch is so eye opening. Just link your credit cards, link your checking account and look at what is that total coming out to. I am even guilty of this. As you know, I have three kids under five. I thought we were living off of $16,000 a month, but we had had two more kids since the last time I did that exercise. We were actually living off of $22,000 a month. But life is moving so fast, right? Like and changing diapers. You got to get them into daycare and running the business like life moves quickly. And so I even had to come back into integrity with taking the time to be like, wait, what? Are we spending a month? Because we've had two more kids, right? So taking the time to actually like sit down and figure out what does it cost us to live our lifestyle and what are we spending money on? And are we spending money in alignment with our values, or are we filling voids?

Jasmine Star 00:08:42  Ooh, okay.

Jasmine Star 00:08:43  Story time. You had mentioned monarch and I love that. I love it here again. Here again. It's my parents balanced a checkbook. And I remember as a child being at a financial planning seminar for my parents, and they were very much in debt, and they made people who were in debt stand up and cut their credit cards in front of like, a glass container. So I saw my parents cut their credit cards, and then they they lived in cash in envelopes, and they would put out what they pay for rent and what they pay for gas. And if you went through your gas money in the envelope, then we were taking the bus like it was that gnarly. So here I am, years decades later, and it's 2022, and my husband and I sit down with a journal very much like this, and we sat down. And we don't use credit cards, just generally. So we sat down with our bank statements, him on his laptop, me and my laptop. It's a Friday.

Jasmine Star 00:09:33  We're supposed to get a date night. Okay, this is not the precursor to a good day. Let me just.

Kaitlyn Carlson 00:09:37  Tell.

Jasmine Star 00:09:37  You. So we sit down and we're going through everything, cataloging everything manually by hand. Caitlin. And we did it for the previous three months, three completed months. And what we realized was that we were overspending in some categories that were crazy food expenditures, livestock just to the wind, two sheets to the wind. And that to me was the biggest eye opening thing because I had realized that I was spending in a void whenever I felt like there wasn't enough story I told myself is like, I'm gonna shop, I'm gonna fill it. And if I go back to my childhood, it was like, oh, we couldn't have that. So then now I just like shop, I buy, I do all the things. And that was a big turning point. And so I just kind of wanted to share that, because if somebody is looking right now and they're like, oh, monarch feels intimidating, or there's this, it's like, if you keep your head in this and it will stay in the sand and having a conversation with you, it's just been like a total up level for me and really having to go deep.

Jasmine Star 00:10:33  It's like, how much are you going to save? How much are you going to invest? So the three questions that you had asked, where are we now? Where do we want to go from here and how do we get there? That is for the six figure founder, the seven figure founder and the eight figure founder. So as somebody is getting a successful business, what are the common mistakes when they're coming to you? And you said 90% of the people don't know how much they're spending on a monthly basis. That's one mistake. What are other ones that we can like hold a magnifying glass to ourselves?

Kaitlyn Carlson 00:11:03  Another one is letting time pass and saying, I'll get to that, I'll get to that. And just thinking, oh, the one of the biggest things that I see is people say like, well, I just don't have money to invest. Well, you're not going to have money to invest if you don't go through this exercise and find out what is that number that I what is my financial freedom number? What is the amount that I need to?

Jasmine Star 00:11:27  So just make sure you're on the same page when you say what's my financial freedom number? That's a language that was really foreign to me.

Jasmine Star 00:11:32  When you say, what's my financial freedom number? What do you mean?

Kaitlyn Carlson 00:11:34  Great question. So I did this when theory was making $0.

Jasmine Star 00:11:40  Hold on. We should talk about theory.

Multiple Speakers 00:11:41  I'm a professional podcast host.

Jasmine Star 00:11:43  Let's talk about theory. We're going to get to theory the business of your business. But let's set the context of why you're a gangster.

Kaitlyn Carlson 00:11:48  Oh, I'm a gangster. So I my background is in private wealth management. So I worked with the ultra high net worth families in this country for. I've been in finance for 15 years. Wealth management for ten. I was one of the youngest private wealth advisors at UBS Financial Services. And during that time, there were two things that I did not see while I was there. I worked with over 300 clients. Not one of them was a woman. The other thing that I didn't see before I was in private wealth, I was in Wealth Management America. So you were working with just everyday Americans trying to retire over and over and over again.

Kaitlyn Carlson 00:12:26  I would see business owners come in and I would be having to give them bad news, whether they had to work another 20 years or double the value of their business, or in some cases, like triggered by a health event. I'd be telling them I'm sorry. You're used to living off of 400,000, but you're only going to be able to live off of 90. And I kept having this conversation over and over and over again, and I was like, why is this happening? And when I realized it was because of the compensation model. So the traditional wealth management model is called an asset center management model, meaning that Jasmine, if you give me $1 million, I charge you 1%. I make $10,000 a year off of your million dollars. Your money grows with the markets. My income grows. It's a very lucrative model. And you don't feel it because I take the fee directly from the portfolio. So that model neglects business owners, because most business owners don't have lump sums of liquidity sitting around until they have an exit.

Kaitlyn Carlson 00:13:28  Well, eight out of ten entrepreneurs never exit. So that model severely under serves the business owner demographic, and I wanted to do something about that. I wanted to empower women, and I wanted to give business owners access to the service and strategy and support. I was giving $100 million clients because I knew these are ambitious people. They just don't have access to the support. So I created theory on two words. I wanted every client to have an advocate and a protector. And so with theory, I had to think very differently about the comp model. So we run a flat monthly retainer, and we specialize in working with predominantly seven and eight figure female entrepreneurs.

Jasmine Star 00:14:13  Well, thank you for that amazing clarification. Now that brings us to the point of 90% of the people who come in very successful, statistically atypical level entrepreneur. They have what it takes. They just don't know the pieces that come together. So 90% of them don't know how much they make in a month, and then they don't know what their financial freedom number is.

Jasmine Star 00:14:36  And when you describe financial freedom what is that?

Kaitlyn Carlson 00:14:39  So this is where we get to that second question. Where are we going? Most entrepreneurs never take a step back to really dream and ask themselves, like, what do I want my life to look like? Because the business, there's usually so much going on with the business and you're so focused on growth that it's that hamster wheel, right? It's like there's a fire. It feels like a really good excuse to just focus on the short term and just like revenue this year. But at the end of the day, like your life is for you to live what you want your life to look like. And I like to say work optional because everyone that comes to us loves what they do for a living. But going back to what you were saying about having options, wealth is the luxury of choice. Yes it is. It is luxurious. Wealth is the luxury of choice. It is the luxury of being able to walk away from the business when you want to, for whatever reason, you want to take a sabbatical.

Kaitlyn Carlson 00:15:35  You want to retire? Do you want to exit? It takes time to position you to have those choices. So we need to get really clear on when do you want work to become optional versus necessary. But what are other goals? Do you want.

Jasmine Star 00:15:52  To be like, let's break this down. Like, this is just what I do. I feel like I'm the voice of the audience because I'm like, I'm a special snowflake. I don't understand a lot of things at first go around, so work optional. If I say okay for the sake of conversation, I'm 25 years old and I want to stop working when I'm 35. I know people are like, I know I'm not 25, okay, let me just live. So I want to stop working when I'm 35. Then you would say you have ten years to save up a certain amount of money, so that at 35, should you decide to retire or not, you have that option. So work optional is I have decided I would like to now do people come in and say it's work optional when I make this amount or is it work optional by an age? What do you see the most of?

Kaitlyn Carlson 00:16:28  It's a combination.

Kaitlyn Carlson 00:16:30  Okay. so because when you become work optional, it means that your assets have replaced your need to work. So the income that you're receiving from your assets have replaced your need to run a company or have any sort of income, because the income that's being generated from your assets is, is replacing your need to work on it. So if you are 25 year old and you're coming to me and you're saying I want to be work optional by age 35, my first question to you is, well, how much do you spend a month? Because at the very least, you're going to want a continuation of lifestyle, right? So if you spend $20,000 a month, we're going to run the numbers for okay, how can Jazmin be work optional by age 35 spending $20,000 a month? That's going to come back and be a certain portfolio size. So let's say it's $4 million. Okay. Jasmine has ten years to accumulate a $4 million portfolio. Is she going to do that through saving and investing regularly. Is she going to do that through an exit? Okay, well, you add 30% taxes.

Kaitlyn Carlson 00:17:33  On top of that, she's going to have to sell for 6 or $7 million. What's the company valued at currently? Is it valued at two? All right. Well, we have ten years to grow the value of the company from 2 to 7. That level of context, nearly every entrepreneur is missing that context. Yep. I mean, that's what we provide.

Jasmine Star 00:17:53  100%, which is why I felt like this is why I wanted this conversation, because you get the luxury of speaking to 0.7 percent of any woman in business will build a business over seven figures. We're not talking about profit, we're just talking about overall revenue. I know, so you're talking your total addressable market is 0.7% of all entrepreneurs. This podcast serves a lot more than that. So even if people are not there, how can you answer the same questions that Caitlyn is asking those of people with larger businesses? Because we can all duplicate this model in different ways. Now, first mistake is not knowing how much they make per month.

Jasmine Star 00:18:27  The second mistake is not understanding or knowing what has to be in place in order for it to be work optional. And the third mistake common mistakes we see.

Kaitlyn Carlson 00:18:34  Another common mistake, I would say, is a lot of people think that a bookkeeper and a CFO is the same thing, and it's not.

Jasmine Star 00:18:42  Oh, we talked about this. Okay, say more about this.

Kaitlyn Carlson 00:18:44  This is good. So if people are not quite ready for theory, I say hire a good CFO because a CFO is responsible for overseeing the financial health and growth of the company. You need that position first. Well, it's a little bit of chicken and egg because on the personal side, you need to know what the business needs to do for you. So I'll use myself as an example. I started theory I'm making $0, but I went, you know, you could just go to NerdWallet and just type in, I want to be financially independent or retire by age 60, spending $30,000 a month for me. I ran that calculation and it told me I was going to have to save $13,000 a month.

Kaitlyn Carlson 00:19:25  Save and invest $13,000 a month. So I was very clear from day one of running theory, this business needs to give me $13,000 a month to save and invest.

Jasmine Star 00:19:35  Like beyond your living expenses.

Kaitlyn Carlson 00:19:37  And my living expenses. But what does that inform my pricing structure? The number of clients I take on, what I do and what I don't do, because I have that number in the back of my mind that is my North Star. Doesn't mean I'm going to hit it tomorrow, right? But it is a North Star that informs so many of my other decisions. So when I hired my CFO, I said, I need to cover my living expenses, and I need $13,000 a month to be going into my investment portfolio. Now, theory has taken many iterations since I started it. When I started it, I just had this little dream that I was going to be a solopreneur and just have 40 clients. Now we have a team of nine people, so obviously that has changed. But what has not changed? Being financially independent at age 60.

Kaitlyn Carlson 00:20:26  Spending $30,000 a month. So I go to Matt and I say, okay, I'm not a solopreneur anymore. And now I'm running a company with a team of nine people. But that North Star is the same, and he helps me translate. What does the business need to do to achieve that North star?

Jasmine Star 00:20:42  Okay. So I want to I want to go back and it's understanding how much we are spending every month to live and be very real with that. Understanding the the number we would have to be able to meet in order to be work optional by a certain age or within a certain timeframe.

Kaitlyn Carlson 00:20:59  Yes.

Jasmine Star 00:21:00  And number three, making sure that you have a team not just a bookkeeper but a CFO. So I had no idea when we really started scaling the business, getting into the digital space. So when I was a solopreneur photographer, we had run multiple seven figure, but it was just my husband and myself. Like, we were fine with the bookkeeper. We were fine with somebody filing our taxes.

Jasmine Star 00:21:19  Then we get into the online space and things just grew really fast. We met with the CFO. He came on board and we did not know how good we had it. I just thought was like, this is what everybody does. And then he sold his book of business, and as he sold his book of business, I realized that the company that had bought his business were bookkeepers, very good at what they did? Bookkeepers, they were not CFOs. And so we went through a whole year and a half of waiting to be like, well, once they understand our business, then we're going to go back to what we used to get, okay? Once we pay more, then we go back to what we used to get. And we just had this like wake up. Like we're never going to get that because they're two entirely separate things. And so for us moving into 2026 and getting a CFO going back to we have a bookkeeper. We have a CFO. We're talking to a tax strategist.

Jasmine Star 00:22:04  And for those of you guys who are interested, had a great conversation with Carlton Dennis. Be sure to check that out. We'll link it in the show notes. Now we're here at this conversation. And this is a conversation that JD and I have. I know that it sounds awful, and I don't want to actually say it because I think that people are going to have an opinion online. And then I just realized, well, I don't care about their opinion. It's my life. And I'm sitting here with a brilliant person who could speak directly to it. So we bought this house. It was a complete fixer upper and we poured money into it and I love it. Caitlin, the day I walked into this house and I walked through it, I cried and it was beautiful and it felt like a deep breath of air. And that same day I told my husband, I see us listing the house. And he was shocked. And he's like, are you not happy? What happened? I was like, no, it's everything because it's everything we wanted and I can't tell you.

Jasmine Star 00:22:55  I know we're listing the house like it's in me. I already know I am so happy. I have no ambitions to move right now. But there's a knowing in me, I know it, I feel it. And he said, okay, when I hear you talk after our conversation, the first thing that came up was like, well, how do I figure out my work option number? How do I figure out what we're going to need? Because I can tell you, if all things stayed equal and we saved if Luna wants to go to college. If Luna would. If we want to travel twice a year, if we want to do all these things and we come up with that number and then we change a house, that's a big change, a very big change. And I know how much we would need liquid because I love I know it's disgusting. I love a little chaos, I love building, I love tearing down, I love designing. It's like if it's not chaotic, I don't know what I'm doing with my life.

Jasmine Star 00:23:36  So it's like, I want a new project. Like I already envision what the house looks like. I can see it, and my husband's like, do you know how much liquid we need for building that? I was like, I know, but we'll just find another fixer upper. So all of that to say, I know our number is changing. What do we do in the meantime?

Kaitlyn Carlson 00:23:51  Right. So that's a good example of you have your peaks of the mountains, right. There's there's multiple and and I always say like between your personal life and the business and legislation, you're it's always fluid, it's always changing. And that's why we are like your Sherpa on this journey. So what you're telling us is, okay, a peak has changed. And so we're going to change our path. And our job is to provide the context and be a sounding board to help you do that in the smartest, most effective way possible.

Jasmine Star 00:24:21  Can I tell you what comes up for me? What is? I'm so.

Kaitlyn Carlson 00:24:23  Happy.

Jasmine Star 00:24:24  That I would have somebody as a sounding board. And then there's a part of me that feels like that's like a little bit of a constraint, because you would be forcing me to make a decision like Jasmine. You sell the house. And what this means is you either work another four years or you find a way to increase revenue so that your owners pull every year turns in to be a different number. And then I'd be like, oh, that's too much trust in the business. Do I want to work another four years? Like, I don't like to make decisions. I'm just like to like, let it be. And I think that what I've needed in my life are those constraints, what the trade offs is. Are you willing to work more or radically change your income to get the outcome that you desire? And sometimes I don't know if I really want to say I want to work more or I want to live on this, right.

Kaitlyn Carlson 00:25:05  Or introduce more time. So in terms of like a goal.

Kaitlyn Carlson 00:25:10  So when we're talking about like work optional for example. So you can push out the time frame, right? Or you can decrease the lifestyle or you can save more. So there's you have choices. That's why we call it modeling. Yeah. We're going to model different things. So you can see how you feel in different scenarios. That's all we're doing is we're contextualizing for you. But ultimately yes, previously you haven't been presented with those trade offs. So you don't really know how you feel. You know how when you ask someone a question and you already know the answer, and then they give you the other answer and you're like, that just affirmed that I want this answer. Yes. We're kind of doing that for you. Yeah. You know. Right. But when you knowledge is power. So when you have that information you can make an informed decision.

Jasmine Star 00:26:00  So I have like a just like flash fire questions I was going to do sometimes I do like I start with a game and it's like under 60s answer these six questions.

Jasmine Star 00:26:09  And I just felt like your whole vibe and energy, I'm like, we're not playing the game like that is out of alignment. I could just feel it. So I was like, okay, we're going to can the game don't need to do that. But I actually want to answer these questions cause I feel like it would drill down for somebody who's listening to contextualize it for them. So I don't want somebody to be like, well, that's nice to have. I'm nowhere near that. Well, right. But many of us were always in the position until we were there. How do we best prepare, even if we're not at the precipice of being able to work with somebody like theory. So true or false, if your business is profitable, you're automatically building personal wealth.

Kaitlyn Carlson 00:26:39  False.

Jasmine Star 00:26:40  Okay. Explain.

Kaitlyn Carlson 00:26:41  You need to take a $5 a job because it's human nature that if you don't give dollars a job, they will be spent.

Jasmine Star 00:26:47  So when you say give dollars a job, explain it to me like I'm five.

Kaitlyn Carlson 00:26:51  So let's say that you're it's great that you're profitable. Like a lot of I did notice when I first got into this space. Kind of like the vanity metrics, right? It's like people talk about revenue, but revenue really does not matter. Profitability matters. So what are we doing with that profitability? How is it helping us reach our goals. How is it helping us further our mission? Again, it's kind of this balance between the CFO and us. If there's a game plan and a roadmap, we're very clear on, okay, the business made $500,000 of profitability this year, and it's going here, here and here. That's because there was a plan in place before the 500,000 was.

Jasmine Star 00:27:34  Given the dollars.

Kaitlyn Carlson 00:27:34  A job. Yes. That's those dollars are going to be going towards things. That's actually what I see people miss the most is just the execution. Right. So we and it's funny because we see this with clients. The clients that are on a monthly savings cadence are building wealth faster and smoother than the people who say, well, let me see how the year goes.

Kaitlyn Carlson 00:27:57  And then I'll and then I'll dump money into my portfolio.

Jasmine Star 00:28:01  What's a general rule of thumb like for somebody who's listening? And maybe they're not at the 7 or 8 figure mark? A general rule of thumb, percentage wise, how much does somebody be saving so that they have a pathway to wealth.

Kaitlyn Carlson 00:28:09  I mean, automating is certainly like that's one of the best things that you can do.

Jasmine Star 00:28:15  Is a general rule of thumb for percentage wise, like 2% every month, 10% every month. And I know it's different for everybody because most people are living paycheck to paycheck. But if there's like a way for you to say, can you live a little bit less and be able to put 3% every single month automated? Have you seen like a general rule of thumb or just be like, whatever you can, however you can.

Kaitlyn Carlson 00:28:32  It's it's a little bit of like, whatever you can, however you can. Yeah. I mean, if you could do like 5%, that could be meaningful over time, like when I so I just paid off my student loans last month.

Kaitlyn Carlson 00:28:43  I paid them off 13 years early. Congrats. Thank you. And I took a three pronged approach. So even though I had $200,000 of student debt, I was still I was an employee at the time. So I did a 401 K, I contributed 5% of my salary to my 41K, because there was a 5% match with the company, I put 5% into my savings account and then I paid down my student loans. I did that for eight years, basically. Like 22 to 30. By the time I was, I was actually 29. But by the time I was 29, that's when Covid hit. I had $70,000 in my for one day. I had $30,000 in my savings account, and my husband had built $100,000 in his 401 K. So because we had been doing the slow and steady three pronged approach, we had built up assets by the time Covid rolled around. Well, Covid comes, they roll out the CARES act. They say you can access your for one K without taking the 10% penalty.

Kaitlyn Carlson 00:29:41  You can take up to $100,000 loan against your 401 K. So that's what we did. So rather than paying Navy at 8% on $180,000, we I liquidated my retirement account. Part of the reason why I did that is because it was the only time I was going to avoid the 10% penalty, and I was shifting from being an employee to being a business owner. This is.

Jasmine Star 00:30:04  Crazy. I didn't know this part of the story. It's freaking brilliant.

Kaitlyn Carlson 00:30:07  So I knew being a business owner was going to open me up to massive wealth creation vehicles in terms of like retirement savings, like solo for one case or defined benefit plans or like cash balance plans. So I was like, it's fine, I'll take the hit now. I'll avoid the 10% penalty. So I took the 70,000 out of my 401 K, liquidated. Most of our savings, paid off 100 or sorry, paid off 80. And then my husband took a loan against his 401 K and paid off the other 100. So we paid off $180,000 to Navy INT, which we were paying 8%, and with A41K loan you pay yourself the interest so rather.

Jasmine Star 00:30:47  Than it.

Kaitlyn Carlson 00:30:47  Out. So rather than paying deviant 8% interest, we were paying ourselves four and a quarter on $100,000. Oh my god. So we did the boring thing, right for eight years. Just like save and invest, save and invest, pay down the debt. But then Covid comes. That's a wealth building opportunity.

Jasmine Star 00:31:05  And you couldn't forecast it, but you just somebody had told me just yesterday. The quote I heard is you're not responsible for the abundance, but you're responsible for the preparation. Yes. And so you just prepared for the moment. So you had the option to do something that you wouldn't have if you had not made those small step blind, those small blinds. Like, it's going to happen. It's going to. That's amazing. Yeah. I hope that people hear that and they listen and they say, okay, that's the thing I'm going to do before I get to these big, massive things. Those are gonna be things. Okay. So, yeah. How much money should an entrepreneur have before considering to work with financial planner?

Kaitlyn Carlson 00:31:38  That's a tricky one.

Kaitlyn Carlson 00:31:39  I mean, for theory, we have people come to us. Who did you say? How much should they have saved?

Jasmine Star 00:31:45  How much should they? Should an entrepreneur have before considering working with the financial planner for us?

Kaitlyn Carlson 00:31:50  $0. That's a huge thing that makes us different as we charge the flat monthly retainer. So it doesn't matter. But the traditional model, would you?

Jasmine Star 00:31:58  Okay. But like you have a flat monthly retainer and let's just say I'm not going to give like a number, but let's just say for math's sake it's $5,000 a month. Let's just say it's $5,000 a month. Somebody has a 5000. But they, you know, on a quarterly basis have 5000. So they have 20,000 at the end of the year. Are you still taking them as a client. Does it really make sense for theory.

Kaitlyn Carlson 00:32:20  Our fees 1500 a month. So I would say to feel good about that energetic exchange. We like to see people able to put at least 30 to $50,000 a year towards their financial goals.

Kaitlyn Carlson 00:32:31  That would be a good fit for theory.

Jasmine Star 00:32:32  That's great. And so when you are in so for people who are listening, this is really just all I wanted to do is to go back and say, at what point in your journey, if you had heard something that you would be able to say, okay, that's the bull's eye. I didn't even know what I was like saving for or aiming for. So had I heard this a decade ago, I would have. I think my life would have been really, really, really different because I think that the way that the model is built is built for somebody like me at that time. And so I made a lot of circular patterns until I came and found you and your perspective. Okay, so should your business be your biggest retirement plan?

Kaitlyn Carlson 00:33:06  Absolutely not.

Jasmine Star 00:33:07  Okay.

Kaitlyn Carlson 00:33:07  Explain that. Okay, so the cornerstone of wealth preservation is diversification. So money is created through concentration. It's preserved through diversification. For entrepreneurs they start off concentrated in their business.

Kaitlyn Carlson 00:33:27  And that's great because concentration leads to the outsized return. Right. Like high risk high reward that is good for a certain period of time. And that's where you can get that outsized return. But over time, we need to start to diversify away from the business, because it's okay to be living and dying by business performance for the first five, even ten years. It's not okay to be living and dying by business performance. 30, 40 years into business ownership.

Jasmine Star 00:33:57  I wish that ten years ago somebody would have said that. I think that alone is so profound because, I mean, here again, don't have a history with money, have never started a business. You come into money, you think that it's going to be good and up and down, and then you just continue doing it until you don't. And then I thought to myself, well, that's not going to work. That's not going to work. So.

Kaitlyn Carlson 00:34:18  Right.

Jasmine Star 00:34:18  Part of the reason why I wanted to have this conversation was people are watching and listening, and they want to know how they turned their money into wealth.

Jasmine Star 00:34:25  What are the small things they could start doing? And obviously, you have built a model that's built for specific, ambitious women who have a successful business. Okay, we're moving in that direction, but I want to go back and talk a little bit about the why and then the business of your business. So this podcast is literally I just loved I could talk about business all day, every day and twice on Sunday. So let's talk about the structure of your business. And then we'll go back and talk about. But why why was it created this way? Because I felt like that was super fascinating. So the structure of your business, you said you have nine people, so you sit at the top and then you have planners with their own book of clients.

Kaitlyn Carlson 00:35:00  So they don't necessarily have their own book of clients because we all share the clients. Okay. But one concept that was I feel like I intuited, but then it was just affirmed by a friend of mine, Sarah Casey Tengri. She's a nervous system regulation coach or guide.

Kaitlyn Carlson 00:35:19  She talked about the Sanskriti model, where it was scientifically proven that if a baby had parents who were supported by two layers of support, the baby's nervous system would be regulated. And I not only want to positively impact female entrepreneurs, but I also want to create a culture where women can thrive, whether they want to be mothers or not. And so theory works in this model where we deliver white glove service. Our advisors work with only 40 families, which is very rare. That's like a very private wealth model. Most advisors work with like 150 to 300 clients. So each advisor is the primary on 40 households. So they're the lead. And then they have a co-lead who is also familiar with their 40 households. And then that co-lead is a lead on 40. And then they have a co-lead for their 40. So it's this model where like, you can truly go on vacation, you can truly go on maternity leave. We have an advisor on maternity leave right now. I have two other advisors stepping in to support her households so she can truly feel like she can step away and rest and rejuvenate.

Kaitlyn Carlson 00:36:32  That was the culture that I wanted to build, is like, when you're away, you're truly away. You're not checking your phone every two seconds.

Jasmine Star 00:36:39  And so your clients come in and your business scales when you have your advisors. And so you know that when you're going to go into like a growth season or there's like a big wave that you have your advisors built set up, that there is a web of support with each other. And so you've built this and you've stepped into that. But why did you leave UBS? What happened? And then why did you decide to make a decision when all systems go. Point you you're on a very successful track. Like what happens for you to say, this is where I stop and a new part of me begins?

Kaitlyn Carlson 00:37:11  Well, the candid answer is I had this conscious thought that if I wanted to be successful in private wealth, I was going to have to sacrifice my safety. And I mean, I, I was sexually harassed. Starting my first week in private wealth, I was asked to take my clothes off in front of a 68 year old advisor.

Kaitlyn Carlson 00:37:31  So that was my first week in private wealth and it didn't get better. After that, I ended up. Fortunately, he was my boyfriend at the time. He encouraged me to come forward with a claim, and I did. And fortunately UBS ended up firing that advisor. But it was pretty relentless to be. You know, I was in my mid 20s and I'm surrounded by men and I'm prospecting men because who has private wealth? Men, men have private wealth. And I ended up submitting six claims in three years. The, the first one that was the most jarring because it was so unexpected. But about a year after and I went through that experience and they fired the advisor and I just stayed quiet about it for a year, because I didn't want to get a reputation for being difficult to work with. And I mean, you know, this about me, that I was an ice hockey player. So, like, I grew up in a boys locker room. I grew up with boys, like spitting where I sat.

Kaitlyn Carlson 00:38:31  So it wasn't that I was not used to being around men or being tough, but this was different. It was like exploitative and explicit and so demeaning. So I went through that experience, and then I didn't say anything for a year, because I didn't want to get a reputation for being difficult to work with. But then a year later, an assistant came to my office on a Friday afternoon and she closed the door to my office and she said, hey, I heard you were the advisor that filed the complaint that got that advisor fired. And she said, I'll never be able to thank you enough because he tortured me for years. And after she said that to me, I realized, like, this isn't just about me. This is about all women protecting all women because there are younger women coming in after me. And that assistant was 20 years older than me. So I ended up filing the rest of the complaints. And then I became a private wealth advisor, and I had a business partner who knew everything I had been through, and he still physically assaulted me on three different business trips.

Kaitlyn Carlson 00:39:39  And after the third business trip, I came home to my husband and I was like, I just can't do this anymore. So that's when we were living in New Orleans and we ended up moving back up to Boston, and UBS was pretty good about it. Like, I went to them and I said, you're going to pay for us to move home. You're going to pay for me to get on a new private wealth team. You're going to give me a raise. But like, honestly, I was just a shell of myself after all those experiences and what I had been through. And I did end up joining a private wealth team in the Boston office, but it felt like putting a Band-Aid on a bullet wound, to be honest. And fortunately, that that team actually ended up leaving UBS like three months after I joined them. And they went independent, but they opened an office on the other side of Boston, and that was like an impossible commute for me. But it got me out of UBS, which I really needed.

Kaitlyn Carlson 00:40:36  Like I was like really suffering there. But when we made that transition, it caused me to take a step back and like, really take a hard look at the industry It'd be like, is this what I really want to do? Because all the passion had just been stripped out of it for me, and I truly did not feel safe. I did not feel like I could. I felt like I was going to have to sacrifice my safety to be successful in that environment. And my husband was like, well, do you think if you changed who you did this for, that your passion would come back? And I said, maybe. And he was like, well, I've noticed that you love following female entrepreneurs. Like, do you think there's something that you could do with that? And then I started listing out, like, here's all the things that's wrong with the model and how it works today. And he was like, well, do you think you could create a solution to that? And so I did okay.

Multiple Speakers 00:41:36  It's like, I just want this.

Jasmine Star 00:41:37  Like the crowd was wild. Okay. And so Brené Brown calls it gold plated grit. Years later, you could look back at that and say that was a very difficult thing. And we look and none of us will have an understanding of the pain that you had gone through and the fear that you dwelled in. And then the voice, the courage to use your voice to speak up for other people who didn't have that, and to be the quote unquote, very successful, but very difficult one to work with. We will never understand any of that. And then we hear this big, bold, courageous decision you made to God on your own to serve a market. And you knew it was wrong. And you said, I can fill that gap. And we hear this and we're like, hell yes she can. Let's go. But like, now let's get to the real, real. You say, I think I can. Here's how the model is broken.

Jasmine Star 00:42:23  And then you're like, I'm in business. How do you start getting clients? Like, what does that journey look like? Because making a declaration and then making it successful are two very different things.

Kaitlyn Carlson 00:42:33  Yeah. I mean, this is kind of crazy to say, but I didn't even know if I could if this business was viable because I didn't even know if there were female entrepreneurs out there. I mean, like you said, point 7%. The only female entrepreneurs I knew were Sarah Blakely and Jessica Alba. If you're in private wealth, those are pretty much the only two that you know. So I just spent the first 18 months of theory just looking for.

Jasmine Star 00:42:58  So what do you do? Like, let's get, like, nitty gritty. What are you. I mean, what are you on LinkedIn? Instagram, or are you searching?

Kaitlyn Carlson 00:43:04  I've always been highly relational, and I knew I had this, like, wealth of expertise, and I wanted.

Jasmine Star 00:43:11  Was that pun intended?

Kaitlyn Carlson 00:43:13  No.

Multiple Speakers 00:43:14  I love it, though.

Multiple Speakers 00:43:15  Okay. Go on. Sorry.

Kaitlyn Carlson 00:43:17  And I knew I could educate. I knew I had my knowledge, right. Like, my knowledge was my big thing. So I actually started with podcasts. I took a leap of faith and I hired a podcast booking agency. And that was great because it gave me a lot of practice telling the story and explaining these concepts. The also thing that it was a huge disconnect for me was like, how little the layperson knew. Yes, it took me a long time to understand how much the general population does not know about wealth building. And so podcasts. Our industry is so nebulous and so intimidating, and so podcasts gave me great practice explaining concepts in a digestible way. So I started with the podcasts, and then I actually used my intuition. I did join an online mastermind, and in that mastermind I identified my ideal client avatar, like literally a person. I was like, this is my girl and she is still a client today. Oh, and we've helped.

Kaitlyn Carlson 00:44:21  We've helped her build multiple seven figures net worth. She got a multi seven figure offer on her company this year, which she turned down because her company is so well run that she can get distributions off of it without really requiring much of her time at all, but she knew exactly what she needed to get for an offer because she has her financial plan.

Jasmine Star 00:44:47  Oh that's amazing. So you get on podcast. You hire. So I'm looking this just as like from a marketing perspective, you have an idea, you build the business, you know the offer, but you're not exactly quite sure who that is because you don't know how big the market is and you don't actually know how to tap into this market, because it's really hard to find. And like, absolutely. It absolutely is hard to find. So then you get in podcast networks and then you join a mastermind where there's seven figure founders are you meet somebody who say, I can build my model after this person. You secure her as a client.

Jasmine Star 00:45:18  You now have since helped her get like eight figures for a sale that she chose. I don't really need because the business is printing me money and I don't have to do much. And then from there, how did it expand? In same ways if you just going out and networking and meeting people?

Kaitlyn Carlson 00:45:31  Pretty much. Yeah. So theory I mean I've never posted on Instagram, I don't have a podcast, I don't have an email list. All I have focused on is relationship building and educating.

Jasmine Star 00:45:43  Wow, this is like Fight Club.

Multiple Speakers 00:45:45  Like oh my gosh.

Kaitlyn Carlson 00:45:46  But that feels aligned for me. So I'm A13 projector for human design. So I love intimacy. Like I love one on one conversations. I love presenting to a small group of entrepreneurs. I love getting live feedback. So I built theory in a way that aligns with my blueprint.

Jasmine Star 00:46:06  And on the back of that, knowing who you are and the type of business you want to build, you can still have like intimacy, like with your advisors, and then your business continues to grow.

Jasmine Star 00:46:15  Yes, as a result of that.

Kaitlyn Carlson 00:46:16  And one thing that's really important is right now. So we have a little over 60 clients. My goal right now is to grow to 120 clients with my existing team. I do not have to grow beyond that if I don't want to. And I'm so clear on that because of my financial plan and the amount of discernment that gives me in terms of what I say yes to, what I say no to, and where I spend my time like it's invaluable.

Jasmine Star 00:46:45  And who you say yes.

Kaitlyn Carlson 00:46:46  To.

Jasmine Star 00:46:46  Yes, you get to handpick your clients. Yes, that is a place of power.

Kaitlyn Carlson 00:46:50  Yes.

Jasmine Star 00:46:50  And so now that you have built the business you started and you're like, okay, if I could just get these many, like if I could just have 20 clients. And now you've expanded far beyond that. And your team. Does that change anything about what you see your future to be? Or has the future always been the future? And now you get to do it with like a small group of people at your side? By your teammates, I mean.

Kaitlyn Carlson 00:47:09  I definitely think Tracy Litt has a great quote. She says expansion happens at the speed of safety. And I totally get that because especially as I was like healing from everything I went through in private wealth, I kept my vision really small. And then I started to grow. And then I was like, well, maybe I could have a team. Right now, I want to be realistic about the fact that I'm very like goal oriented. So I want to focus on this goal of getting to 120 clients and then seeing how it feels. One thing that feels very natural for me is I do feel that I am here to mentor. And so my focus right now is transferring how I think to the team, not what to do, but how I think because I want them to advise the way that I advise. Right. I'm moving into that leadership era, which is super exciting for me, and that feels very natural for me. But that took a while because a lot of my ego was wrapped up in, oh, my value is in my skill set in what I do.

Kaitlyn Carlson 00:48:15  So I had to go through a lot of mental work to, oh no, it's actually my leadership and the systems and the framework that I've built. Like that's the value. The value is not me, the value is the framework and the results that it's getting for clients.

Jasmine Star 00:48:31  Can we go back to how we started the conversation? And you had said the three most important questions that we have to ask ourselves is six, seven and eight figure founders is where are we now? Where do we go and how do we get there? So you had said, where are we now? 60 clients. Where do we want to go? 120. So my question to you as we close is how are you going to get there? Like I want you to point to the stands like Babe Ruth, be like, this is it. This is how I see it. Are you there yet? Are you okay sharing that?

Kaitlyn Carlson 00:48:58  Yeah. So, I mean, I have my 2026 calendar built out already, so I'm a part of three groups, three networking groups.

Kaitlyn Carlson 00:49:09  And two of those groups have two events this year and another group has one. And then there's like another dinner that I'm doing in Atlanta. So that's 5 or 6 events that I'm going to go to.

Jasmine Star 00:49:24  In 8 or 10 clients. I had a girl.

Kaitlyn Carlson 00:49:27  So simple gives me gives me the time to work out and spend time with my kids. Just enjoy life.

Jasmine Star 00:49:35  And maybe this podcast. Maybe ten, 8.

Multiple Speakers 00:49:37  Or 10 out of ten.

Jasmine Star 00:49:39  Caitlin, I want people like one of the things I was really impressed is I was like, okay, so talk to me about all of your avenues, what you want people to do. Like Jasmine, I have a one page website. If people want to chat and figure out if they're a fit, if you just go and book a call, where do they go? How do they book a call? Give us give us the details.

Kaitlyn Carlson 00:49:55  Yeah. So that is correct. It's a one page website. It's theory. Theory planning comm. There's a link at the bottom to book a call with me, and I'm happy to chat to give you a gut check on where you're at in your journey and see whether it's a good fit for theory now or, I mean, I love to leave people with something, right? So if if you book a call with me, I will tell you, you know what the next best step is?

Jasmine Star 00:50:21  I absolutely love that.

Jasmine Star 00:50:22  And enlightened in full candor, I don't have a vested interest in how her business grows. If her business grows, it's like high fiving all the way around. Because when Caitlin wins, the clients win. And if you become a client like this is the ultimate goal is how do we all collectively move upwards together? How do we create momentum? And so I brought Caitlin here because I wish that I had this conversation with Caitlin a decade ago. And because I can't. The best thing I can do is to put somebody else who's a decade prior to where I am now to build out. And so the lessons have always been for me. I made a promise to God. Whatever I learned, I'm going to share it. And so this is me taking those lessons, putting them out there. And so I hope that in the future we can look back at this day and be like, wow, Jasmine, you were dreaming a little too small. You were dreaming a little too small. So thank you for just being an expander, an opener, and giving people hope.

Jasmine Star 00:51:08  But then concrete steps. These are simple things we could start doing. So you had mentioned Nerd Wallet. You would also mention monarch and you would also mention theory planning. Thank you.

Multiple Speakers 00:51:18  Thank you thank you so much I appreciate you.

Kaitlyn Carlson 00:51:21  Thanks for.

Multiple Speakers 00:51:21  Listening. Ladies and gentlemen.

Jasmine Star 00:51:22  Thank you for watching and listening to The Jasmine Star Show. Caitlin Carlson, you're the best.

Kaitlyn Carlson 00:51:25  Thanks, Jasmine.