A Paradigm Shift to Wealth Creation with Kaitlyn Carlson


I am so happy to have Kaitlyn Carlson on today.  Kaitlyn is a wealth planning expert and the Founder and CEO of Theory Planning Partners.  Theory’s focus is on wealth creation for female entrepreneurs and they achieve their clients goals through collaboration, transparency, empowerment and objectivity.

In this episode we will cover:

  • Assets under management
  • Flat Fee Model
  • Balance Sheet – the holistic approach

You can find Kaitlyn’s website here or find her on Instagram @theoryplanningpartners.


Legalpreneur LIVE tickets are now available!  We may be a company founded on legal protection, but Legalpreneur LIVE is all about business and personal growth with your  tribe of business besties.  Use code LPLIVE50 for 50% off your ticket through June.

Now is a great time to join the Legalpreneur Membership! Get in now before prices go up in the spring. Learn more here.



Andrea’s Instagram 

Legalpreneur Instagram 








The Legalpreneur Podcast is advertising/marketing material. It is not legal advice. Please consult with your attorney on these topics. Copyright Legalpreneur Inc 2022



Episode 188: A Paradigm Shift to Wealth Creation with Kaitlyn Carlson

Andrea: [00:00:03] Welcome to the Legalpreneur Podcast. I’m your host, Andrea Sager, founder and CEO of Legalpreneur, Inc. As a serial entrepreneur and someone that works exclusively with small business owners legally protecting their business, I’m dedicated to covering common legal issues faced by business owners, providing you with the business knowledge you need to catapult your businesses growth and showing you just how some of the world’s most elite entrepreneurs have handled these legal and business issues themselves in true attorney fashion. The information in this episode is not legal advice. This is for informational purposes only, and you should always consult with your attorney before implementing any of the information in the show. Legalpreneur alive. You guys, we have a special offer for the rest of the month of June. 50% off of general and VIP tickets. Plus, you guys, so many people are like, what’s the number one draw? And besides the fact that we have Allie Webb, founder of Drybar, Danielle Canty, co-founder of Boss, Babe and Pauleanna Reid, and so many other speakers. You guys free child care. And we just started really like telling people cause I was like, oh, like, of course it’s going to be included. And so many people are blown away by the fact that we’re going to have free childcare.  I’m like, Hey, my kids are coming. I want everybody else to be able to bring their kids. I don’t I don’t want anybody to not come because they don’t know what to do with their children. Hey, I want my kids to see me at work. If you want to bring your kids and let them see you at work, bring them like, let’s do this. So use code LPI Live five zero. 50% off general and VIP tickets. Vip So many perks. But number one is the VIP mixer with all of our speakers and you guys, you’re going to get free breakfast, you get lunch like it’s all included. Get there, get your ticket. Phoenix, Arizona, October 5th to seventh. I’ll see you there.

Andrea: [00:01:59] Hey there. Welcome back to another episode of the Legalpreneur Podcast. Today’s guest is a wealth creation expert, Caitlin Carlson of Theory Planning Partners. I am so pumped to hear from her because I love talking about money. It is something really deep on my mind lately. Going through my divorce and basically being depleted to nothing. I am rebuilding, so I’m excited for Caitlin to be here and for you guys to hear from her and learn from her. So, Caitlin, thank you for being here.

Kaitlyn: [00:02:32] Thanks for having me, Andrea. I’ve been looking forward to this podcast for probably two months now.

Andrea: [00:02:38] Yeah, me too. And I know you have, like, changed directions, ideas so much. So get us started. Give us your background. How did you get to where you are today?

Kaitlyn: [00:02:51] Oh, my goodness. Yes, I have had to let go of perfectionism in a big way. So my background let’s see. I guess we can go all the way back to the fact that I am a native Bostonian. So I was born in Massachusetts and grew up playing ice hockey and that took me all the way through college. So I played ice hockey in college and I always had an interest in finance. My grandfather bought me my first stock when I was eight years old. It was one share of Disney.  And I remember him saying that that one share would make money. And I and I said to him, how will I make money if I’m not working? And he said, Well, and so that whole idea of your money making money for you was planted in my mind pretty early. But at the time I was really disappointed that I didn’t get something tangible for my birthday. So it’s funny how at the time my grandfather probably didn’t know whether it landed with me or not, but lo and behold, it definitely did. It stuck with me and through compound interest is worth a lot more than $38 now. So that planted the seed in my head for an interest in finance, and my dad was also in finance. I saw myself going into that field, but when I got to college, I was I thought I was going to major in Econ, but I ended up being far more fascinated by psychology. And so I majored in psychology. And shortly after college I went right into the finance field. And so I started an asset management with a mutual fund company called Putnam Investments. And Putnam sold mutual funds through financial advisors. And so I learned what financial advisors did.

Kaitlyn: [00:04:40] And financial advisors work with families, individuals and business owners to essentially manage their money. When I learned about that potential career path, I thought, what a great combination between my interest and finance and my interest in psychology. Because as we all know, money, money is far more emotional than it may appear at first. So yeah, once I learned what Financial Advisor said, I kind of had my eye on switching from asset management, which is one small sleeve within finance into wealth management. And my husband was offered a job opportunity to move down to Louisiana. And so when we made that move, we actually started at the same company. And when we made that move, I switched from asset management and to wealth management. And so I went into a two year program. It was called the Wealth Planning Analyst Program with UBS Financial Services, and I was very intentional about choosing UBS. They were a highly reputable firm. They were the largest wealth management firm in the world. And they capped the. The amount of advisers they had at 7000. So I liked that there was a bit of exclusivity to it and I knew I was going to get a high caliber education there.

Kaitlyn: [00:05:57] And the thing that really pulled me in was they were going to pay for my CFP, my certified financial planning designation, and that it was very important to me to get as much education as I could while I was learning on the job. And so in that role as a planner, I worked with over 300 clients. Many of them were small business owners. I covered four states by myself. So Louisiana, Arkansas, Mississippi and Alabama, which as a girl from the Northeast, you can imagine that was just quite an education in and of itself. I definitely understand that there are like multiple countries in one country. And so but I love like business owners really stood out to me is just a fun group to work with. And so I did that for two years and then I myself ended up becoming an advisor and that’s when I moved more into the private wealth world. So I ended up working with the 1% of the 1% and got exposed to pretty much the wealthiest families in America and what they do with their money and how they protect it and sustain it. And also the mistakes that they make. 

Andrea: [00:07:16] Oh, God, I would love to have like, a whole another episode just hearing about, like, horror stories, but also, like, the exciting stuff.

Kaitlyn: [00:07:24] Yeah, I know. We should have started, like, amongst the planners and advisors, like a gossip column or something, because the stories are endless.

Andrea: [00:07:33] Oh, my gosh. Epic.

Kaitlyn: [00:07:35] Yeah. So, yeah, that really fueled my my passion for working with business owners. Unfortunately, while I was at UBS, I had to deal with a lot of sexual harassment, and that was exhausting. I was sexually harassed my very first week there by a 68 year old advisor.

Andrea: [00:07:54] Oh, my gosh. I’m so sorry you had to go through that.

Kaitlyn: [00:07:59] You know, it’s it’s part of my story. I ended up filing six sexual harassment claims in three years. And it was just an exhausting it became like a second job. So I had to that was a big part of me leaving UBS, certainly a part of me getting out of the South. I just couldn’t do it there anymore. So we moved back up to the northeast. I joined a private wealth team up here for a short period of time. But honestly, with all the experiences I had been through there, it was just too toxic for me to stay. I ended up leaving and co-founding a firm with a former colleague. That’s when I got my CPA designation, my certified exit planning advisor designation. But again, the majority of people that were exiting their businesses were middle aged men, and I just couldn’t do it anymore. I was so sick of I was so sick of prospecting middle aged men. So after a lot of refractory reflection and my husband pointing out to me that I really should just follow what I’m passionate about, I realized that female entrepreneurs were really the thing that I was passionate about in the fact that of those 300 clients, I never worked with a self-made woman. So that was something. Yeah, it was pretty remarkable when I looked back on it. It’s a big driver. Behind my mission with theory is women just don’t have access to the same network or the same level of advice or the same sophisticated conversations that men do. So theories mission is a lot about bringing. You know, with the expertise that I learned in the private wealth world to women who are making more money than they’ve ever made before and want to know how to steward that wealth.

Andrea: [00:09:51] Mm hmm. So explain how exactly you work with clients in theory.

Kaitlyn: [00:09:58] So that’s a great question. Well, being an entrepreneur is certainly been a lot of trial and error. One thing that’s really different about theory is we do not charge based on assets under management. So.

Andrea: [00:10:12] And can you explain that really quickly for people like the different structures and explain exactly charging based on assets under management? I know what it means, but I know I didn’t know what that meant for a really long time. And so I know it’d be really helpful to get all these explanations for the audience.

Kaitlyn: [00:10:29] Yes. So I found that to be one of the biggest problems with wealth management, particularly when it came to serving business owners. So the assets under management model is essentially if you have $1,000,000 in liquid assets, meaning that it’s essentially in cash and you give that to me to manage for you, I invest it for you, I charge you typically 1%. So I would make $10,000 a year off of managing your million dollars. Now, the problem with that is the majority of business owners, 80% or more of their net worth is wrapped up in their business. So they end up getting severely underserved until they have some sort of liquidity event like selling their business. And I always felt like this, even the even in the private wealth world, it was like no one really cared about them. And then when there was a hint of an exit, it was like wealth managers were like sharks on bait, like swirling around them. And I just felt like this is so wrong because there are so many wealth building opportunities along the way for entrepreneurs. But because wealth managers don’t get paid based on anything other than assets under management, they’re not really motivated to care about servicing you to the highest degree or helping you all that much until you have liquidity for them to manage. So when I left the wealth management world, or I guess the corporate world, that was something I was very intentional about, was I wanted to be able to charge a flat fee. And business owners love having the predictability of a flat fee. You know, you build it into your expenses.

Kaitlyn: [00:12:16] And and I wanted to be able to provide them with the white glove service that I was used to providing these ultra high net worth clients. I mean, it’s like counterintuitive in the sense that like all the good secrets and support get reserved for the people that already have the most money and the people that need access to that sophisticated advice the most are the people that are trying to build that wealth, not the people that already have it. So that was something I was very intentional about, and I’m certainly in the minority of my industry for switching to a flat fee model, and it’s just because the assets under management model is so lucrative. And the other thing is with assets under management, it gets deducted right from your investment account so the client doesn’t see the fee come out, whereas when you charge a flat fee, we send an invoice every month or every quarter. So you are seeing the fee. So advisors are very reluctant to switch because it’s almost like it gets taken out and no one notices. So there’s not a big insight and it goes up with the market. So if your account grows from 1 million to 1.5 million and I’m charging 1% now, I’d be making 15,000 for not really having to do much versus 10,000. I don’t know if the industry will ever change, but it’s going to be really hard to get advisors to step off of that model because it’s lucrative. And and truthfully, there’s a lot of mystery behind it. And advisors don’t hear about clients complaining about that. So.

Andrea: [00:13:56] Yeah. I feel like it’s the same with lawyers as far as switching from the hourly model to the flat fee model. I’ve always done flat fees and attorneys love the hourly model, even though clients don’t. And I 100%. There are situations where it does not make sense to do a flat fee model. It’s just not possible. But especially when you’re doing transactional work with trademarks or something that is very repetitive, I think it is very it makes a lot of sense to do flat fees.

Kaitlyn: [00:14:31] So I love flat fee because the hourly honestly gives me anxiety.

Andrea: [00:14:37] Yeah. Like you want to have a conversation with your attorney and it’s like, oh, my gosh, how much is this conversation costing me?

Kaitlyn: [00:14:43] Yes. Like, you’re not even paying attention because you’re like, what? How many minutes have gone by?

Andrea: [00:14:48] Exactly. Yeah. That’s all you’re worried about. And with flat fees, it’s like, okay, you don’t have to worry about that. Like, it’s all included. Yeah, right. I’m a huge proponent of flat fees and I think it’s very similar to you doing flat fees versus assets under management.

Kaitlyn: [00:15:03] Well, to answer your original question, so in addition to the flat fee model, the other thing that makes us very unique as we work exclusively with female entrepreneurs and typically when you’re going to need us is when you are starting to make more money than you’ve ever made before. And what we do that’s different is we take a holistic approach to your balance sheet as a business owner. And by that I mean when I’m looking at your net worth as a business owner, your business is likely going to be the largest line item on your net worth statement. So it’s incredibly important to me and to everyone at theory that we’re optimizing the value of that business. And that was something else that was never done in the wealth management world. The business was largely ignored on the balance sheet, but we take a very vested interest in making sure that the company is running as financially healthy as possible, because if you’re optimizing the value of your company, you’re then optimizing the value of your net worth and then not only optimizing the value of their business, but are there other wealth building opportunities outside of the business that we can be taking advantage of? So we work around the periphery as well to make sure that we’re like maximizing retirement accounts or I’m sure this is big in your world, Andrea, but asset protection, if you’re starting to build a really valuable company, then that’s when we need to start bringing in like estate planning attorneys and making sure, like making sure, okay, you’ve built this really valuable business. Now, how do we protect it? And if you’re good, then you think about that from day one. So that’s why we need you. Yeah.

Andrea: [00:16:48] Yes. No, I love that. Always protect your assets, especially your intellectual property. That’s probably your business is most valuable asset. That’s what that’s what I like to tell a lot of people.

Kaitlyn: [00:16:59] Absolutely. I’ve seen it firsthand on valuations. It’s so true.

Andrea: [00:17:04] Yeah. So if somebody, let’s say a female entrepreneur, just starts rolling in the dough, most money they’ve ever made, they have no idea what to even begin doing. Where like, what’s the first step? Even if they’re like, I don’t even know if I’m at the point to hire a wealth. Management. Manager. What do they do?

Kaitlyn: [00:17:28] I think that’s one of the most common myths or mistakes. So we also don’t have any sort of asset minimum. It’s more about what once you start having that thought in your mind, it means you should start taking action on this. And so we help female entrepreneurs build out their financial team. I call it their success team. So your success team should and this is something that I’ve learned over the last two years is. Typically an outsourced CFO or CFO will be integral to the success of your company. So what I’m finding is incredibly valuable is having someone do evaluation on the business, having an outsource CFO or some type of financial strategist, because most people that start up businesses are more of the visionaries than the CFO type role. But you need that information and that strategy to make educated decisions. So a CFO would be helpful. A CPA. Now, all of these people need to be talking and communicating effectively. That’s the whole thing. So getting people on your success team, CFO, CPA one would be us. So the financial advisor, financial planner, the corporate attorney, potentially estate planning attorney, if you’re above the estate tax threshold, are getting close to it, potentially an insurance person to make sure that you’re protected both business insurance and life insurance, disability and then like home and auto, that kind of stuff. We again, we’re looking at the entire picture.

Kaitlyn: [00:19:11] So we’re kind of like quarterbacking this process and pulling in the people that we need at the time for the task that needs to get done. So that’s kind of like your core team. And then if you want to build to sell, eventually you’re going to need to have that corporate attorney come back in and potentially even hire an investment banker. And then that’s when you might need to add a couple other people, potentially a consultant. We really take that quarterbacking position because business owners have become successful for their zone of genius and they’re not equipped to typically they’re not equipped to handle the byproduct of their success. So you have a lot of people going to the business owner saying, oh, like, well, do you want to do this? And they’re like, I don’t know, you’re the expert. I thought I hired you for that. And then they’re the ones coordinating because they have a financial advisor saying, Oh, we’ll talk to your CPA about it. And it’s like, Well, the last thing that a business owner has is time to be the go between. So we really try to take over that project management role to make sure that everyone is coordinating cohesively and also that it’s going towards a larger long term plan versus making these siloed, potentially short term decisions.

Andrea: [00:20:26] Yeah. And would you say there’s a certain number where it makes sense to like if somebody literally has no savings, they have no cash? Like, does it still make sense to bring you in or somebody like you in? Or should they at least have like money in a 401. K or an IRA? Like, where do they get started?

Kaitlyn: [00:20:46] That’s a great question. So they don’t need to have any savings yet. It’s more about where is the revenue of the company going? I would say the one thing that I’ve discovered, like I mentioned in the past two years, is you should be in a position to hire an outsource CFO and a CPA before me, because those are two people that I need on my team to be able to coordinate with, to figure out, what are we doing? Are we setting up a company for one K plan or are we setting up a solo for one K plan? Like what’s what’s the big plan here? So if you’re starting to get into high six, seven figures and you’re starting to think about building out a team, I’m finding that. Really once you get over into seven figures is when having building out that that team makes a lot of sense. And then the other thing is, one new client said this recently. She was like, I feel like I’m about to be holding this together with tape and glue and I don’t want to feel that way. So if you feel like you’re holding your financial picture together with tape and glue, then that’s a good indication that, I mean, at the very least, start reaching out to these individuals or or feel free to reach out to theory because we’ll be able to tell you whether it’s too early or whether we think it’s about time that you should start hiring somebody. Because the really important thing is, regardless of whether you’re building a company to sell it or you’re building more of a lifestyle brand, you want to have a really solid foundation. And the younger you can do it, the better. Because especially when it comes to things like investing, I mean, time is your greatest asset.

Andrea: [00:22:25] Oh, yeah. That is something that I’ve been learning and I’m trying to get started. Like for the kid, my kids exactly like time is on your side, get started as early as possible. So I’m currently working on that with the kids, especially now that my divorce is final.

Kaitlyn: [00:22:42] So yeah, I love it. I mean, teaching your kids is that goes all the way back to my grandfather buying me that chair. You know, they’re they’re such sponges at that age, probably more than you even realize. And plan planting those seeds of positive financial habits can make a huge difference.

Andrea: [00:23:00] So I’m very curious about the nuts and bolts of how your grandfather bought this stock when you were eight. So. Did he buy this because E-Trade wasn’t around? These online trading platforms weren’t around. So I’m. Genuinely curious. How did he buy it and how do you how would you access it today?

Kaitlyn: [00:23:24] So that’s a really funny question because so he bought it in an account which is a custodial account for children. And so my dad was the custodian on it and I was the beneficiary. Now, when you turn 18, it’s 18 or 21 for Aetna, as they always forget. But by the time that I rolled around to like actually putting it into my own name, I think I was 27 and I think I was married. So this is typically what happens with this is like you forgot about it and it’s way past. Yeah. So he bought it for me in a custodial account. Now it took forever to try to track the cost basis of it because it was a physical share and they didn’t track cost basis back then. So I have a physical share of Disney that was like in a blue. It was in a blue bin in my parents basement, buried away somewhere. And that’s largely how it was for a really long time. It was pretty manual until, you know, mid 2000. So he bought me that one share and it was on a dividend reinvestment plan. So the dividends that I would get from that share would then go towards buying more shares. And so eventually it turned into, I think, 45 shares. The cost of Disney stock or the price, I should say, of Disney stock went from $38 to $140. So not only am I buying more shares, but the value of my shares is going up. And so that’s what really creates the compound interest. But now, I mean, it is so much easier. Like you can just create a custodial account on fidelity and it’s like a couple of clicks of a button or we clear through Schwab like, you can do it on Schwab too. But yeah, back in the day it was extremely manual and when we had to move it from the Ummah account into my own, since I was an adult, into my own individual brokerage account, it was like this hellish process for four months to try to get it all set up. So it’s far easier to manage.

Andrea: [00:25:31] Yeah, but that’s, that is really cool because I remember as a kid when my mom, she would always tell me she’s like, Oh, I want to buy start buying you stocks. I’m like, What? Like, what the hell is this? What do you mean? Like? And I didn’t get it. And she actually didn’t explain it to me. She didn’t explain, like, get your money to work for you and. Not saying, even if she did, it would have changed. But I that’s I just want to get my kids started early and I want to get them because right now I think they see, oh, mommy works. Mommy travels a lot for work. And I want them to realize you don’t have to always travel. You don’t have to always work to make money.

Kaitlyn: [00:26:16] Yes. Yeah. No, it’s. I mean, I think that was the biggest transition from people often ask me like, what’s a wealthy mindset? And I mean, I grew up middle class, so it was like, you go to work and you get a paycheck and, you know, a pension or like you save into a41k. But especially for business owners, there’s such an incredible opportunity to build wealth. And I often saw and say that wealth is built through concentration and preserved through diversification. So I mean, a lot of business owners end up becoming really wealthy and a lot of their wealth as concentrated in their business. And then when they’re able to sell it, then that’s really I mean, there’s two ways to go about it. Like you can build it to sell where it’s pretty much locked in your business and then you have a liquidity event and you unlock it. Now, having said that, 80% of businesses that are put up for sale do not sell. So you have to be you have to run your company as a best in class company to be in that 20% to sell. The other option is you can run more of a lifestyle business where it provides you with a nice lifestyle and good cash flow. But you have to be disciplined about building your financial independence or your nest egg away from the company so that you can eventually walk away from the company. That was the biggest mistake that I found business owners made over and over and over again. I mean, after working with 300 clients, I think I said it four dozen times, like you just you haven’t saved enough to be able to walk away from this company. And when you’re 65, you not want to be hearing that.

Andrea: [00:28:00] Oh, that’s the worst.

Kaitlyn: [00:28:02] Yeah, that’s the one one piece of wisdom I would impart on everyone is if you’re building more of a lifestyle business, even if you’re not, even if you’re building to sell, you need to start thinking pretty early about how to build financial independence away from the company. And that’s where we come in, because we’ll tell you what that number is that you need to be reaching for.

Andrea: [00:28:24] Kaitlin, you are such a wealth of knowledge.

Kaitlyn: [00:28:28] Thanks for that, ton, andrea.

Andrea: [00:28:30] I like. I would sit here all day and just talk to you about this stuff. But I know the listeners are like, okay, I just want to go ahead and just call Caitlin. So call Kaitlyn.

Kaitlyn: [00:28:44] Yeah, please.

Andrea: [00:28:45] She will get you started. But before we leave. I ask all my guests the same question What is your number one business tip? It doesn’t have to be even wealth related. Whatever your number one business tip. What is it?

Kaitlyn: [00:29:02] My number one business tip. Is. I just talked about this, but it’s begin with an end in mind. And I know that’s I wish I could think of like a cooler one, but really beginning with the end in mind is so important. And realistically, it might take you a year or two to figure out what that end looks like. But the earlier you can think about what you’re building towards, the more successful you’ll be.

Andrea: [00:29:31] And I love how you just broke it down as far as, hey, you’re going to build to sell, or you’re going to have a lifestyle business. That’s one of the main things you have to have in mind, like what is your end goal?

Kaitlyn: [00:29:42] Yes. And I think that is kind of it takes the first year or two to figure out like what’s going on here. And one of my building towards the sooner you allow yourself to get that answer, the better. How’s that?

Andrea: [00:29:56] Caitlin, thank you so much. Let the audience know where they can find you online and we’ll put everything in the show notes, you guys, and seriously reach out to her sooner than later.

Kaitlyn: [00:30:06] Sure. Yeah. So feel free to reach out. My website is theoryplanning.com and I just fired up my Instagram again, which is at theoryplanningpartners. So feel free to DM me there or reach out on my website. Very accessible.

Andrea: [00:30:24] Kaitlyn, thank you so, so much.

Andrea: [00:30:26] Thanks for having me, Andrea.

Andrea: [00:30:30] Here at Legalpreneur, we’re committed to providing a supportive legal community for all business owners. I know how scary the legal stuff can be. If you found this information helpful, I would be so grateful if you could share it with the fellow business owner. And quite frankly, it doesn’t cost anything to rate, review or subscribe to the show. Your support helps me reach more listeners, which allows me to support more business owners in their entrepreneurial journey. Have any questions or comments about the show? Feel free to drop me a line on Instagram, I promise. I read all of the messages and comments and if you want to be a guest on the show or know someone that would make a great guest, simply fill out our application form and a team member will reach out if we think it’s a good fit. I’ll see you in the next episode.