12 Days of Giving: Day #4 – From W-2 to Freedom: Unleashing the Power of a Sole Proprietorship

Join Stoy Hall and Dominique Henderson in this impactful episode as they unravel a client’s journey to financial empowerment. Discover the true essence of financial planning, extending beyond numbers to life-changing transformations.

🚀 Episode Highlights:

The power of client stories in financial planning.
Balancing W-2 jobs and side businesses.
The role of time and options in building true wealth.

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Episode Transcript:

Stoy Hall, CFP®:
0:00

Happy holidays, everybody. Another episode of 12 days of giving with my man, Dom. You guys have had him. You’ve heard him a lot on the pod and I will continue to do but I am so grateful for him as a human. As a friend and what he’s done in the 23 years that he’s had his wealth management firm, as we were just chopping up about that. So with that, though, it’s all about the client and a client story. And that way you can relate to it and be like, Hey, you know what? That’s me. And they’re successful. I think I just need to reach out to someone. So Dom, without further ado, why don’t you give us your client’s story, a little background of them, and we’ll get through it. Oh first of

Dominique Henderson, CFP®:
0:37

all, I have to give honor where honor’s due. Thank you for this platform, Stoy. And I’ve enjoyed getting to know you over the years and what you’re trying to do here and applaud it. Definitely. I will say this one thing before I get started. I think, and I said this on a previous podcast, I said to you, the greatest compliment a client will ever pay me. After working with me is to no longer identify themselves by what they do, but what they’ve been able to become by working with me. And I think that’s a good segue for setting this up. Let’s call him Mr. And Mrs. X. Came to me about three, four years ago. It was actually around this time. So it’s about four years ago. And this is the reason why I always tell financial advisors to build your own sales funnel and build your own email list. Because I, at the time had an offer about how do you pay less in taxes. And it was, I think I had something really cute, like how to cover your assets, something like that. And so she goes through the quiz. This is X goes through the quiz and downloads the guy and she downloads the guide after she takes the quiz because she really feel like she’s paying too much and we set up a call and so we set up the call and her situation is this such so she’s been in academia for a while at the university level and she’s got a really good program through academia so much so that she’s got. The 403B type of deal and the 457 that she’s contributing to and the employer has too. So she’s done really well. At the end of the day, it’s not about the money though, as we always know. And so when we got into the conversation, I started asking some of these why questions because I’m really curious and I’m like, so why are we even talking then? It sounds like everything’s good. You pay a little bit too much in taxes dah. But the deal is. At the end of the day, her job, her W 2, it’s ran its course. She’s done all she thinks she can do, and now it’s getting to the point where it’s getting on her nerves. And on the side, she has a sole proprietorship that she really loves. Gets to set her own hours, and I was like what if we could get you to a point where you could make the decision to leave the W 2, and just do the sole proprietorship whenever you want to? Why don’t we answer the questions? If you have enough money, her Mr. X was, 10 years or senior and he’s already retired, already got his pension. He just fixes houses and does whatever he wants to do. And, but she was feeling and I want your, for your listener to know like the psyche and the ethos that she was in when we met is she was really stressed. She was really anxious. She just, yeah. To be accumulating all this money and thinking you’re doing a good job and talking to your friends about it and just not really sure yourself and not really certain yourself. It does something to you. And fast forward about 12 months or so into that situation. And the reason why I know it was Mr X’s birthday. They were getting ready to go to a baseball game and we always. Her and I most of the time talked uh, I would say 80 percent of the time, but for this particular time, he came in and he was like, yep, I don’t want to interrupt. Just want to let you know that the time you’ve been working with my wife. I’ve noticed a drastic change in her. She’s, she seems like she’s lighter. She’s more fun to be around. I don’t know if I’m paraphrasing. I don’t know if he said that, but it’s she’s not as stressed. She’s not as anxious and it’s I think it’s as a result of the work you guys have been doing together. So I just want to let, I appreciate what you’re doing. And I was like. Thank you, man. I really appreciate that. That’s, nobody’s ever said that to me. And he was like, all right, deuces. And yeah, I’ll do whatever still. And that’s what it’s about story. It’s those, it’s that type of transformation that I actually try to get financial advisors to envision when they’re working with me, like whether it’s an advisor development or coaching or firm launches or whatever, because that’s what you want to try to codify and replicate. The products and the services and the AUM and the data and all that kind of stuff, it’ll come. It’s part of it. How do you affect the type of transformation people are looking for? That is intangible. Dude, I might have added more years to her life. I don’t know. So she gets to enjoy relationships longer in time, which is the greatest currency.

Stoy Hall, CFP®:
5:01

So what? I just got the chills from all that too, because you had the husband come in who usually isn’t involved to say something that he saw and there’s no value to that. That is, there’s no, you don’t know the ROI on that. Like you said, you could have added years to her life. You literally have no idea. Yeah. But everyone says that’s not a financial planner’s role. There’s no dollars involved with that. So why don’t you talk us through yeah, we’re not therapists but what is our duty and our role in that situation?

Dominique Henderson, CFP®:
5:33

Dude, I’m reminded of a scripture. I don’t know exactly the address of this and I need to do it, but it’s like Jesus said, where your treasure is, your heart will be also right. So when you think about treasure, you think about like money, I think people think about, and that’s easy in this conversation, but. Treasure, like wherever I value things, wherever I place my value, my emotions will follow. So if I’m stressed about money, then, then that you’re going to see that manifest in different ways. And it could be my career. It could be my kids. It could be whatever your treasure is. The fact of the matter is your mind will and your emotions will follow that. And so in your particular question Yeah, I am not a therapist. I’m not, but since this particular person, this client and a lot of clients for that, when we’re talking about human capital that we trade for financial capital, let’s call it money. That’s, that’s my skills. It’s my reputational capital. It’s all this stuff that I built up that makes me who I am. And therefore, I care a lot about it. Now, here’s the issue because of how financial education and literacy is disseminated in this country they’re, there’s a population of the haves and the have nots at varying levels of information. And I, what I think. Although there’s varying levels of information, the level of stress and anxiety from my work in 23 years of doing this has been pretty consistent. It has the same effect on everybody. And I think our jobs as financial professionals is to help people navigate that. And it may look like planning, it may look like wealth management, it may look like tax planning, it may look like retirement. There’s a variety of things you can slap on this as far as labels and different ways you can charge for your services and whatnot. But at the end of the day, I like to say financial planning is no less than or no more than how do I take my unlimited choices? And take my limited time and money and spread those across those unlimited choices. That’s what it’s about. It’s figuring out that equation for that particular people set

Stoy Hall, CFP®:
7:43

set of people you’re working with. Yeah, and I talk about this a lot and ultimately what my clients want to know, am I good? And do you got my back? I love that, right? Sure, am I good to buy a car? Am I good to hit this goal? Am I good? Whatever it is, they just want to know, am I good? And if I’m not, do you got my back to make sure we can get through this? And that’s what we do. It’s, yes, numbers are numbers. We can play with that all day. But you is what we’re focused on. So from the emotional side of someone there’s a lot of people stuck. I don’t want to say stuck. Maybe that’s not the right term, but a lot of people in W 2 jobs right now that either have a side gig or thought about a side gig it’s been a huge proponent since the pandemic started of people wanting to launch businesses. What do you, how do you have that conversation with someone who either has one or has the idea of one that is in this W 2 there’s only so much time in the day. What did you, and how did you help her through that real transition mentally of saying, I should focus on this thing.

Dominique Henderson, CFP®:
8:46

Yeah. So here’s where expertise comes in because you can’t fake it. I just, a little bit of my background, I spent six years on a muni bond desk building cashflow and portfolios from, let’s call it six to 8 percent cashflow per year, cash on cash portfolios for six years. That’s just what I did. And I saw a lot of cases, so I know how to take somebody who’s a million dollars and produce 60 grand a year or 50 grand a year in income, like spendable income, like they can count on it every month for a check. And so that helped because I said, um, you realize, and this is, if financial advisors are listening, like this is, I guess a one on one lesson, if you realize what the components of total return are, which change in price. I bought it at eight, it goes to 10. I bought it at eight, it goes to six. The actual dividends or income that those assets produce is the second component. And then we have the compound interest is what you do with that, typically hopefully reinvest. So there’s three components. If you take away the first one, I still have two thirds of the formula left and that’s what I can control. With putting dividend paying assets inside of a portfolio, a high cash flow of paying assets. So that’s what we eventually did. And I modeled a couple of those things for her. And I was like, okay, you’re spending X amount. The assets you already have will produce Y. It’s not that much variance for, because the variance is actually the cost of you going to the W2 every day. That’s what you need to think about it. And she was like, Oh, I didn’t, I was like, yeah. And you already have your side business, which makes up for more than the variance. What are we doing here now? Great. That math was easy enough to come to, but like the mental process of accepting that factual evidence and actually going, okay, I’m going to make a decision. Which looks like retirement and in her case in the next 6 months but it took a lot. I told you I’ve been working with him for 4 years and I’ve been telling her this since almost day 1 with the beginning with, the actual financial plan showed that variance, but it was just like, But, it’s like anything else right in life that we. We see the facts, we see all the evidence presented in front of us. And we go, yeah, something in my brain that just says right now, I can’t do that. Like how long did you think about launching a podcast before you actually launched a podcast? Probably about two years. Yeah. So there you go. It’s not always just a factual thing. There’s a lot of considerations and that’s fine. But at the end of the day, I think to your point, like real simply, you can just, do something like I did is Hey, you’re spending this. yoU’re spending X you’re getting paid this from your assets that you’ve built up all these years. Wait, what time do you want? When do you want to start spending this stuff? And then, just showing them some examples of that. That’s one way. So I use my expertise.

Stoy Hall, CFP®:
11:37

Yeah. And that’s what literally you answered. You answered the first question. Am I good? She wanted to know, am I good? You answered it. But it takes time and time is the actual value that we can provide. And what I mean by that is obviously we can give time back or allude and be more efficient. But the other part of it is. Your journey and wealth is a journey. It is not a, we hand you a financial plan and it’s over. It is not one thing you do it and you’re good in life. It’s like a lifestyle of diet. It’s a lifestyle spiritually. It is a lifestyle change or. Additation to your to have a well journey and I want people to understand it takes time like time. It takes a long time to be either good at something, follow through with it or to see the fruit of your labor. I just think in this society and hopefully it’s getting to that. We just. Want to get rich quick. We just want to do these things quickly. And that’s not life. That’s not right.

Dominique Henderson, CFP®:
12:39

No, there’s not too many things I can think about that are drive through experiences that are lasting. With, I think with the, all the work begins after the financial plan, that’s when life happens. You set that expectation. I think I’ve, I might not be the best salesperson or the sharpest tool in the shed. I just, I think I asked really good questions because I’m curious about getting to what is actually their problem. Like I’ve talked about my three question framework, where it’s you’re asking why three times because. The first why is what they think you want to hear the third why is um, how they actually feel right in that second, why it can be a lot of things, but you want to get to what they feel, what they really feel. Because just because somebody wants to have 8 million in their bank account or whatever their number is that our industry hyper focuses on what’s your number, what’s your numbers. What is that number going to be used for? I can tell you right now in 23 years to do this, I know there’s plenty of studies like, and I know that there’s the bottom half or whatever you want to call it of people that don’t retire with enough, but there’s plenty of people that do retire with enough and they never spend it all. So that means their number was wrong too. So at the end of the day, you’re like. Not that I want to leave here perfectly zero. It’s just that people leave here typically with way more money than what they could have spent. And so it’s not, that’s not the, that’s not what it is. It’s what is that money intended to do? What is it designed to do? Is it designed to give me more time back, right? Buy my time back so I can spend more time with family, developing relationships. Doing things I want to do that kind of stuff. And that’s what it usually boils down to. And you got to get, sometimes you got to dig a little because of all the programming that has happened in our society that don’t allow people to actually be who they’re supposed to be. Like we’re human beings, not human doings. And the layers in the program and get us to thinking that we’re human doings versus human beings. And

Stoy Hall, CFP®:
14:34

what you just described there is my definition of true wealth. And that is happiness, being able to give back friends, family, relationships, that’s wealth. The dollar is not wealth. I don’t care what our society says, media, everyone says the wealthiest people in the world. The wealthiest people in the world that I know, I met in Tanzania sweeping mud floors back in 2011. They’re well, way more wealthy than any actual rich person I’ve ever met in my life. And they don’t have anything. They don’t have a hundredth of what any of us have here in America. And so what you just described as true wealth, people want to figure that out. That is what makes them feel good. It might be a number tied to it if they want to, but it really has nothing to do with that number and what you alluded to, you’ve seen people too much money and not enough money. How many people have you seen that had the perfect

Dominique Henderson, CFP®:
15:25

amount of money? Yeah, I know Chris Rock said this years ago being interviewed by Oprah and she’s like, how would you define wealth? It was something like that. And he said, having options. And I was like, that’s a beautiful definition having options, whether that looks like time options. If you want to make it really temporal, what I buy what I consume down here, or more permanent what I’m able to give away the impact I’m able to build right now. So that after I’m long gone. There’s generations of people talking about me, this depends on how you’re made up depending on how you answer that deal. But it is options. I was just

Stoy Hall, CFP®:
16:04

thinking about that options to options in who you’re around, who you’re with friends. Family, like that’s deep. Ooh, I like that one. I like that. Okay. Chris. Okay.

Dominique Henderson, CFP®:
16:19

Pre slap Chris.

Stoy Hall, CFP®:
16:24

Oh, that’s funny. Oh, that is, that’s good. That’s good. So we’ve got someone in this avatar, if you will, their W 2 potential side business, have a side business. What would you say to them to take that next step? To move forward, whether it’s working with someone or whatever, what is that thing that you think they need to do to take that next step?

Dominique Henderson, CFP®:
16:46

Yeah, I’ll make this one real simple and maybe we can riff off of it, but go see somebody that knows more than you, financial professional wise you’re probably doing pretty good if you’ve been able to. Navigate expertise on a W 2 that pays reasonably well and pop off something else because that takes fortitude and, so if you’re there, like you you’re no dummy. I think it’s like. What’s the Mark Twain quote? It’s it’s not what you don’t know that gets you in trouble, it’s what you think you know for sure that just isn’t true. So don’t fall into that trap. Go hire a coach or a financial advisor or somebody to take you to the next level because you don’t already know. And here’s the deal, what you probably realize if you’re juggling those two things is time is your most precious quality quality, and you can’t produce more than that. So why not hire somebody that knows more than you, leverage what they know. By paying them to me. That’s a no

Stoy Hall, CFP®:
17:40

brainer. Oh, absolutely. I could not agree more With that and that’s yeah a coach a consultant put a title on them I don’t really matter find someone that you can trust that can see things that you can’t see And start to push you to a different level. That’s what you need

Dominique Henderson, CFP®:
17:58

and that well Let me just interject cuz I eat my own cooking So I have a CPA my family has a CPA like and I refer a lot of business to him for my wealth management Dude, I know how to file tax returns. Is that the best use of my time? Absolutely not. I gladly write that three grand check for my S corps and I gladly write that because he does a good job and I don’t have to think about it. Same thing with my my business coach. I can produce content. I could do all this kind of stuff, but like, how do I get that angle where somebody is looking at it with their perspective and going, Dom, you’re doing this really well, but there’s this last 5 percent or even last 1%. That’s going to take you to the next level that you need to consider. That’s what I pay those people for. So yeah, I’m, I couldn’t be a coach and I don’t think I could be a good coach or consultant without eating my own cooking. It’s like that, that four star Michelin chef that doesn’t eat his own cooking. What’s wrong? What’s wrong with it?

Stoy Hall, CFP®:
18:57

Isn’t it? Wait, time out. You cooked it. You don’t eat it? You

Dominique Henderson, CFP®:
19:01

didn’t taste it? I’m scared. Scared is the right word. I’m so scared.

Stoy Hall, CFP®:
19:08

I love it. And everyone listening, reach out to Dom, reach out to me. If we’re not your fit, then we know people who are. That is something that I know we’re online with is being together as professionals. So when we do have a client come to the table and they don’t fit. Our makeup in our firm, we got team behind us that does right. I can go and say, Hey, no, you need to work with Dom. Like this. This is it. He’s your guy or the Rolodex that we have, that we’ve vetted out and that we trust and we have years of relationships with, yeah, let us help you find that as well. It’s, it could be daunting to go out there and try to Google search a financial advisor and planner.

Dominique Henderson, CFP®:
19:46

Even if you say financial advisor near me, because we know, I know specifically that there’s a lot of financial advisors that pay a lot of money to get that be the first research result on that, that has nothing to do with their expertise. It just means that they were able to write the check at that particular time.

Stoy Hall, CFP®:
20:05

Yes. And also don’t be afraid to go outside of where you’re locally at too. Yeah. Now and nowadays, and this is why I love the pandemic part is it took us, our industry virtual, it took us to a different level to reach more people. And so don’t be afraid to look around now. That’d be my tidbit to couple off of you as well. Hey, I appreciate you. Happy holidays. Yeah. Enjoy. And we’ll get you back here the start of the year as well. Yeah.

Dominique Henderson, CFP®:
20:32

You too, man. Stay warm. The

Black Mammoth:
20:47

proceeding program was sponsored by black mammoth. Any awards, rankings, or recognition by unaffiliated third parties or publications are in no way indicative of the advisor’s, future performance, or any individual client’s investment success. No award ranking or recognition should be construed as a current or past endorsement of black mammoth. Information regarding specific awards, rankings, or recognitions is available on the Black Mammoth website, www.blackmammoth.com. All investment strategies have the potential for profit or loss. Investment strategies such as asset allocation, diversification, or rebalancing do not assure or guarantee better performance, and cannot eliminate the risk of investment losses. There are no guarantees that a portfolio employing these or any other strategy will outperform a portfolio that does not engage in such strategies. This broadcast should not be construed by any client or prospective client as a solicitation to affect or attempt to affect transactions and securities or the rendering of personalized investment advice due to various factors including changing market conditions. The information discussed in this broadcast may no longer be reflective of current positions or recommendations. While information presented is believed to be factual and up to date, Black Mammoth do not guarantee its accuracy, and it should not be regarded as a complete analysis of the subjects discussed. The tax and the state planning information discussed is general in nature, and is provided for informational purposes only, and should not be construed as legal or tax advice. Listeners should consult an attorney or tax professional regarding their specific legal or tax situation. Past performance is not indicative of future results.

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