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Matt
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Joel
I'm Joel.
Matt
And I am Matt.
Joel
Today we're answering your listener question.
Matt
That's right everyone. Listener questions on the way. We hope everyone had a fantastic weekend and that you are ready to buckle in with us here at the beginning of this week with listener questions.
Joel
If you're not more than 48 inches tall, you will not be allowed to ride.
Matt
You cannot ride the how to money train.
Joel
You see the disappointment on my kids face when they face that. I think they're all basically, well, I don't know, the six year old maybe not quite tall enough to ride some.
Matt
Of the last time you went to Six Flags or something.
Joel
It's been a while.
Matt
Joe Gorey. No, it's been a while.
Joel
I just remember the look on their faces when they're like wait, I can't.
Matt
Ride after waiting in line for the scorcher or something like that. And you're like, oh, it's actually too short.
Joel
Well, and well then sometimes they're like, actually, that's good. I was a little scared. So they're thankful they couldn't ride.
Matt
What you don't want is for there to be some teenager who's just like, ah, it doesn't matter, they can ride.
Joel
And you're like, actually, you sure about that?
Matt
Okay, I am changing my mind now. And we are no longer going to visit this establishment because I value our safety when it comes to these carnival rides on steroids. But Joel, we're going to hear from the richest how to money podcast listener I think of all time. I'm actually really excited.
Joel
Did Warren finally reach out to us?
Matt
But someone else, another listener is wanting to know what he should do with higher healthcare premiums. And someone else he's considering long term disability, whether or not he's a good candidate for that. Plus other questions during our episode today, buddy.
Joel
All right, looking forward to it. I came across this article about economists saying, hey, you know what? For kids who are dropping out in certain school districts, maybe the best way to get them to finish their degree, their high school degree in particular, is to pay them to stay in school. And I think that. Isn't that just so novel? I mean, I think there have been.
Matt
That's totally the economist's answer to an issue with education. I feel like, you know, this reminds me of. So one of the charities that I donate to that's a part of GiveWell, it's new incentives, which is where they provide cash payments for parents who bring their kids to get these shots and to get these different vitamin, what are they called? Not injections. Like supplements. Yeah, supplements. In order for them to develop properly. Because they don't understand that, oh, these things are necessary. And so but what they do understand is that, oh, if I receive money, then that's a good thing.
Joel
So, yeah, they show up. So it sounds like you'd probably be in favor of this, especially in like, places where you see reduced graduation statistics. Right.
Matt
What do you think? Or like, do you think this is a good idea?
Joel
I guess I'm kind of mixed on it, but I do think, I mean, I think it could even like perpetuate a problem where kids are like, yeah, I'm failing on purpose so I can get paid to stay kind of thing. There's certainly that possibility. But I do think when we incentivize the behavior we want to see, and particularly when you look at the numbers of at least getting a high school diploma, people are much more successful when they have a high school degree than if they, than if they don't matriculate.
Matt
I agree. Like, it does not surprise me that this might work. I think the bigger question then though is, is this the best way to encourage kids to stay in school? Because it's.
Joel
You'd rather have like a mascot that's just pointing the finger and be like, stay in school kids maybe, or like scared straight, but it's like the dare, but for staying in school.
Matt
Yeah, no, like it. What I don't like is that it makes it a completely financial, like, it makes it a transactional sort of a financial transaction, I guess, as opposed to like the higher calling of explaining to kids what staying in school allow, like provides for you. Not just from a financial standpoint like that. Yes, most definitely is important. And they need to know that, hey, if you stay in high school, this is what you're likely to earn. This is how much more you're likely to earn if you graduate with a high school diploma. Oh, if you then make it to a four year degree, a four year college and then graduate with your bachelor's degree, this is how much more you're likely to make. Like, that is important information. But even that, there's still, it still feels transactional as opposed to trying to. And this is a much harder argument to make, but I think one that is worth making in the United States, which is, hey, we need to convince kids and make them aware of who they are becoming by staying in school. Right, like this. And this is ultimately going to turn into like a classical education kind of argument. But like the things like if you make it about the money, then going to school is purely in order to satisfy your desire to make money at some point as opposed to recognizing who you are becoming by putting yourself under a teacher who's excited about a subject matter, who can teach you about some of these great books about kids who are learning the, you know, the true good, beautiful things out there. Like that is a harder, again, a harder argument, but I think a much higher call. And this is also where I think it is a little bit different from other countries where there is not as much knowledge when it comes to health preventative steps that families can take when it comes to supplements.
Joel
Right.
Matt
Because there is just a communication breakdown.
Joel
Everybody listening to a podcast knows about AG1 already.
Matt
You know, that's true in the States there's enough conversation around that. But I feel like it's also when it comes to education, there is an education problem with education. People need to be informed as to why it is we're going to school. It's not just to be able to be able to graduate and make money. It's about some of these higher, bigger, beautiful things that kids are learning and ultimately becoming.
Joel
I think you're also getting at something, too, where we just need to make school better, more interesting, attract better teachers. And part of what's happening right now is an exodus of great teachers from the profession. And, gosh, this feels like kind of a sidewinder topic for us a little bit. But I think the more we make school a place where kids are excited to be, the less we'll have to, like, pay them to stay in it. It's like, hey, stay in this thing that you hate because the education isn't great, or you don't feel like you're enthusiastic about learning. Maybe you actually change the front end of that equation to make it more exciting to be in school and to learn.
Matt
And I think what you're.
Joel
There's a lot of teachers, by the way, who listen to this podcast who are doing just that in their classrooms.
Matt
Oh, absolute. Sure. They would also agree that, like, well, we're not paid enough. And so it's hard to get excited about the subject matter when we are barely scraping by. It's hard to get excited when I'm teaching in a district or a school where maybe the, you know, the families aren't necessarily bought in as well. But what I was going to say was, I think what you're also maybe saying. You're not suggesting, like, there should be more games and let's make this more attractive on the surface, like screens.
Joel
No, no.
Matt
As opposed to finding, again, like, anchoring what it is the kids are learning about to sort of some of these bigger, more ultimate truths, which is like. That's why I said there's, like, an education problem, I think, with education, because it's difficult to communicate that well to families when it doesn't feel like they've got a whole lot of time to pay attention to something like that. I'm sure you.
Joel
Same with me. And most of our listeners could point to at least a teacher or two who had just a significant impact on our lives, especially maybe in a subject matter we were curious about but felt a little dense in. And they just, like, lifted the veil from our eyes, and we're like, oh, my gosh, I get Shakespeare now. This is cool. And so, yeah, great teachers, I think, is a. It's a big part of that.
Matt
Yeah, I will say, too. I mean, so both Joel and I are fans of classical education to one degree or another. We have varying degrees of involvement. But if you are, if you got questions for us, hit us up. This is something we love to talk about when we're not talking about personal finance.
Joel
That's true.
Matt
Oddly enough. I think a lot might surprise a lot of folks. But yeah, email us.
Joel
So it's on the Comeback too. All right, let's mention the beer we're having on today's episode, Matt. This is called Shift. It's by Incendiary Brewing.
Matt
Experimental Shift.
Joel
Experimental Shift.
Matt
Missed the small type thing.
Joel
Well, the purple kind of blended in. My eyes are getting old. We'll give our thoughts on this one at the end of the episode. If you have a money question, please send it our way. Just record a voice memo on the app of your phone. Send it over to us via email. How to moneypodmail.com say your name at the beginning. We like to hear who we're getting the question from. And Matt, let's get to our first question. You said this was from the richest how to money listener ever. It sure is. Let's hear this question.
Podcast Announcer
Hey Matt, Joel, My name is Chris. I wanted to submit this for my husband and our family to prepare for his company selling. And I'm just going to throw out a number of 300 million net after taxes. I'm just assuming at this point. But if you could help us prepare for what we should do with that type of money. We are putting some money obviously into investments, but beyond that we really don't know what to do. We've really just had money in the company and to set ourselves up for the future. That's where we're investing. But for income still coming in and money to be able to use until we hit retirement, we're not sure what to do. We obviously need money for paying for our own insurance now. Things like paying for vehicles, paying for insurance for the vehicles, just everyday living. So if you have any advice on kind of what the best route to go is for just passive income because I don't think either one of us is necessarily going to want to work after this. Possibly something. But yeah, we would love your advice so much on this. It's kind of scary to be done doing something that you know you're good at for years and yeah, taking a whole new route for context, we are in our early 30s so we do have a ways to go until we get our insurance later on in quote unquote retirement age. Thank you so much. Love your guys show. You guys have helped us out so much over the years. So thank you for everything you do for people. And for all your advice, cheers.
Joel
Today's the day Matt became a financial advisor and started charging a 1% assets under management fee.
Matt
Holy cow. This is insane. Yeah, I'm almost speechless as to how it is we should respond to listener Chris here.
Joel
And the 300 million thing sounded slightly theoretical, but also probably in the ballpark of what they're going to be dealing with. And yeah, yeah, let's be honest.
Matt
I mean, so much money.
Joel
Anything cow. I know, like, we'll do our best to answer this question, but also we're just going to kind of offer some general rules of thumb because, I mean, yeah, there's, there's a lot of detail you can and should get into at some point.
Matt
I mean, I feel like we should readily admit too that this is a level of wealth that very few people come in possession of, nor is it, I don't know, do the same rules apply. I guess we'll kind of figure this out as, as we get to this answer. But I wanted to first start off by saying that, Chris, the fact that you reached out to us, like, there is an immense amount of trust. I feel like even by emailing us, and I mean, I would speak for myself, but I think I'm speaking for both of us, that we are honored that you would even want to hear our opinion as to what you should do with this, with this sum of money. And so to that end, I would say the first thing that I would make sure to do is to not post this on social media.
Joel
Yeah.
Matt
Like, I would be extremely careful as to who it is that you're telling about this.
Joel
It's kind of like winning the lotto and telling everybody, you know, and like that can just do things to relationships that you wanna avoid.
Matt
Yeah, absolutely. But that being said, you reached out to us and you told us and so I don't know, I feel like there is a level of trust that you've endowed upon us and I'm thankful for that.
Joel
She mentioned in her email, I think her started this company when he was 15. So this is also something people might be like, oh man, must be nice. But also it's many, many. It's like almost 20 years of incredibly hard work building this business to get to this point still, most people who build a business are not going to experience an exit like this. But I mean, $300 million post taxes is what she said. I think one first thing I want to mention is they should probably be working with an experienced CPA who has done like business exit work.
Matt
Yep.
Joel
Like, because, yeah, 300 million post taxes. Incredible. But just make sure also that you have somebody who's got their eye on the ball when it comes to taxation. You don't want to kind of get caught unaware.
Matt
Yeah, yeah, yeah. And not, not just a cpa, I would even say like an experienced high net worth tax attorney, like somebody who can help you to preserve this amount of, of money that you find yourselves in possession of. But like, and I think what they might help you to do as well is just to not make any rash moves. I think for you, for you and your husband, your family, taking like a cooling off period would be really wise. I think it, you know, it's easy to feel like you should have a perfect plan right out of the gate right after the sale. But it's, I think it's not unlike the death of a loved one. Right. Like sometimes you might be too emotional to assess what is going to be best for you in the moment. What I'm getting at though is that you don't want to like put this money in like your small local bank. Like you want to be looking to national like big time, well recognized banks that aren't going to be failing with this sum of money that they might have on hand. And actually it might be worth looking at. There's a company, Intrafy, and they use these protocols, these systems that funnel all of your money to not just one bank, but to hundreds of banks in one fell swoop. Basically, like you open a single account, but then those funds are divided out into amounts below $250,000 because that's the FDIC insured amount.
Joel
So essentially the biggest risk essentially of like taking this all one sum, one lump sum and even putting in one of our favorite online banks. That's, that's awesome. I guess unless something happens to the financial system, the bank goes bust.
Matt
Yeah.
Joel
And the government says, oh well, every dollar you had above 250 grand, sorry, you don't get to, you don't get to keep that. That vanished.
Matt
Not likely to happen. But that's, that's the reality that you're dealing with. With this amount of money on hand.
Joel
What you're referring to through Intravi is called Sedars. We'll put a link to that in the show notes. But that is a way where you can, in one fell swoop, it feels like opening one account, but you get one statement while your money is dispersed around to a bunch of different banks, ensuring that every dollar remains FDIC insured.
Matt
Again, preserving the money and having it to Remain. I feel like that is your number one goal right now with this. And again, going back to like getting an experienced CPA or a tax attorney. Like, you need to be putting together a team of folks who understands the ins and outs here to help you to essentially create like this. It's like you are creating a house, like a structure, like you're creating a wealth architecture. And someone who is experienced can help you to put something like that together in order to serve you and your family for the long haul.
Joel
Which makes you think if you don't have a financial planner, that's something worth considering. We'll talk more about that in a second. But I think even before that, Matt, thinking about goals and dreams is a really important part of what you do in the aftermath of a business exit too. Like Kris mentioned, they've got kids. What do you want for your kids? You might want to have an estate attorney as part of your team because you're talking about planning for the future. That might be another person who you bring on to your, your team to manage this money effectively and to help.
Matt
You make sure, yeah, totally worth paying all the professionals who are at the top of their game. When again, when we're talking about the.
Joel
Sum of money, you obviously don't want the money to stay in cash for too long. Ultimately you're going to want to have different buckets, a few years worth that stays in cash or cash equivalents that you can safely withdraw from. You're going to want to have other money that you're willing to take risk with in the market in order to grow it. Probably another bucket that's thinking about the long term future, like goals for kids or bigger philanthropic efforts which you might want to participate in. You can work through those things with your team. But I think starting to think about goals and hopes and what you want to accomplish with this money, it's really important to have those discussions. Yeah.
Matt
And I'm sure you've been, you might be saying, yeah, we've had some conversations like that, but I bet they have. I bet they're gonna look different now. Let's just be honest. I think aside from some of these, like really large goals and sort of like the kind of legacy you might want to leave, I think it's worth thinking through, like what you want your ideal life to look like for you and your family today. Like, you know, I think it sounds like it might be easy to just bag work altogether. But again, with your husband, man, I'm guessing he's really driven and I'm guessing he has worked really hard for years, if not decades. And I think going from, you know, pedal to the metal and all of a sudden bagging work, kicking back, I think someone with that kind of drive might go a little crazy not having something like that that you are excited about.
Joel
And so going from nose to the grindstone to pina coladas can create like some depression or. Yeah, I would just think that would be a tough mental thing to go through.
Matt
I think it could, yeah, it could lead to some issues. And so yeah, thinking through what you want your days to look like, like your months and even from year to year with your kids, just what some of the different phases of life might look like. And actually in your email you mentioned something about buying property. I think some of these thoughts, if this is something that you're interested in and excited about, makes a ton of sense in particular again because it gives you an outlet of how it is that you're going to be spending your time that way. Again you're not going from, you know, 100 miles per hour down to zero.
Joel
I think just like with folks who have a lot less money but they're interested in trying things out as well, it's important to like dip your toe in. Right. So for instance, Chris, her and her family, they're going to have yacht level money now but instead of just like buying a yacht, they might say well let me just rent one for a month or something.
Matt
A yacht is much more affordable than purchasing one. I've never done this myself. Yeah, this is not within my depth of understanding some of the things you have to pay attention to when you're renting a yacht.
Joel
But you got to think that there's similar to renting an RV or something like that before you go all in and just buy a brand new one. Yeah, that, that, that mitigates I think a lot of potential harm that you could do to yourself by buying the thing and then not using it. So just want to throw that out there. Let's also talk about passive income. That was one of Chris's main questions. There's just no need to over complicate things. I don't think on this front. I mean since you're, you're coast fire on steroids, I'm assuming I don't know all your expenses, but I'm assuming that this amount makes you, that yes, you wouldn't have to invest anymore. Right. Like still you want the nest egg to grow for future spending, future giving, all that kind of stuff. Like there's no, no Reason just to sit on it. I think a rough rule of thumb is that you can spend something like 4 1/2% of the balance every year and still never run out of money. That's like $13.5 million annually.
Matt
Yeah. Where that money invested in the market.
Joel
So not sure what your spending habits are, but that's probably far more than you need. You might hear about annuities as part of planning. Most are probably not worth considering and the bulk of the money should probably be in like growth and long term buckets with just enough cash to cover current flexibility and some of the like. If you're going to buy properties, some of that, you don't want to invest it and then pull it out when the market's down. In order to make that property purchase, you might want to keep that in short to medium term buckets. She mentioned insurance too, Matt. It's a good idea to increase your coverage. You might for instance, want a larger umbrella insurance policy. Just more personal protection.
Matt
That's right. And I think she was, was she asking about having to like buy their own cars now? Like maybe before they had company cars and their insurance was covered also by the company. Like yeah, that's not a problem anymore. Yeah, like yes, you do have to pay your own premiums now. But, but paying premiums on insurance is an expense I would gladly pay with this amount of money because again, the name of the game now is for the most part about protection and preservation of that money. And to that extent I would find.
Joel
Finding joy without letting it overwhelm you too.
Matt
Yeah. Gosh, this is such a big question, a big conversation to have. I feel like we're not even really touching on the joy. Bottom line. Like you have the money on hand now, right? I feel like finding the joy, like that's a conversation that's great to have with folks who are in pursuit of money as to whether or not that's going to bring about lasting happiness. But the fact is you got the money. And so let's just make sure that it doesn't slip through your fingers like water. But I want you to find an advisor to work with. And one of the things you mentioned in your email was not wanting to become a lottery winner, which I totally get. That is a real risk. A massive just cash influx can seem like a blessing, but it can quickly feel like a burden. And man, if it was me, I'd be careful who I'm telling about it. But having a trusted advisor could provide you with a sounding board, someone to also discuss those hopes and dreams with. So you can just take a more dialed in approach to your money, to your investments and yeah, how much you can actually regularly tap while continuing to grow that nest egg for future goals that you might have. And we've mentioned them before, but wealth ramp an incredible resource. Fiduciary. Yeah, you want to talk about a fiduciary advisor, Chris. But like man, you, I hate to say this but like you are such a target now and you need like fiduciary everything now. You know, you need like fiduciary friends, fiduciary family, which hopefully is maybe a bit redundant to say that. Right.
Joel
Sign a contract and buy.
Matt
Hopefully your family wants the best for you anyway. But things get weird when you're talking about such a large sum of money.
Joel
Yeah, yeah. I mean it really. Anytime you look at athletes, like or just entertainers, people who get rich and then their money can get between friendships. And so part of that is keeping it on the DL. Another part is just having a philosophy about how you handle money with the people you love around you. And yeah, I mean I think that's one of the things I heard Mr. Wonderful being interviewed, Matt, the guy from Shark Tank, and he just talked about how that's like the hardest part of having a lot of money is people come to you out of the woodwork. They're wanting to bor. They want you to invest in their startup, whatever it is. And so yeah, the less you advertise your newfound wealth, the better. But yeah, finding a top notch financial advisor I think is really important, not just finding an advisor.
Matt
Right.
Joel
And that's where wealth ramp comes in. We'll link to that in the show notes. Yep. All right, we've got more to get to on this episode. We'll talk about healthcare costs, a lot of how to money listeners dealing with much higher healthcare costs in 2026. We'll get to a question on that. Talk about rental properties after this.
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Joel
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Matt
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Joel
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Matt
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Matt
All right, buddy, we are back for the break. We'll get to a classic 401k match question here in a second, but let's now hear from a listener who is Mandy struggling to accept the fact that he might be paying so much money to go towards his health insurance.
Ad Voice
Hey, Joel and Matt, this is Josh From Franklin, N.C. about two hours north of you guys. I was reaching out. I'm just looking for another trusted opinion. I have spent about a month now researching different options, and I don't feel like I am confident in any decision that I'm coming up with. My wife is a stay at home mom with our two girls, and she has used the healthcare marketplace, but with the recent subsidy changes, her healthcare is looking to go up about threefold. So we have been researching the health sharing plans like you guys have discussed previously, like, better share. We're looking at the healthcare marketplace and our different options there. We've also discussed just coming out of pocket using fqhc, our local community hospitals, nonprofit hospitals, asking for cash prices and just paying out of our emergency fund and HSA funds. The only problem there is it worries me if something catastrophic happens. And I'm a little worried about the health sharing plans because of the. The fact that there aren't necessarily any regulations. But I just wanted to reach out to you guys since you. Since you have different opinions and you have experience, you can share. And I'm hoping you guys might help point me in the right direction and hope all is well. Joel, keep logging those miles. If you'd like to come up in March and run the Asheville Marathon, just let me know. Thank you, guys. Thank you so much for your time.
Matt
Bye. I'm offended, Joel. I run sometimes. You do?
Joel
You're very fast.
Matt
Rarely do I run. Not nearly as much as you.
Joel
Well, should I run the actual marathon?
Matt
I don't know.
Joel
Sounds like a good one.
Matt
If you're gonna run a marathon, I mean, there's gotta be awesome breweries along the way, right? Like, I think you would have to go.
Joel
My time would definitely be slower.
Matt
You'd have to. The fact that this is just a really long, fun run as opposed to I'm going To set a pr. Yeah, you can't be entering into that race with that kind of headspace.
Joel
Or maybe I have six Pierce and set a pr and that's more power to you, man. The best PR you can set.
Matt
That'd be amazing.
Joel
Well, Josh, appreciate your question. You're obviously not alone in being essentially assaulted by higher healthcare prices. This is something we've documented on the show for sure. People are scrambling as subsidies decline. Price shock is setting in for a lot of folks. Some people have enough wiggle room, right, to absorb those higher premiums in their lives, but many don't. Especially when you're talking about as significant of increases as we're seeing. Matt, some people are going from, oh, yeah, I was paying $300 a month and now it's looking like I got to pay like 7 or $800 a month in premiums. That's before. That's before you get to. Right. Actually going to the doctor. Some people are saying, you know what, I'm just going to cancel health insurance altogether. I'm going to see what happens. Throw caution in the wind. Others are opting for health sharing. So this question is becoming more common. And while it might not be ideal, the lack of regulation, especially surrounding health sharing companies, a lot of folks I think are going to find they don't really have another better choice.
Matt
Yeah, no, I don't think there's really an ideal solution for most folks. Josh, you are right. Both of us, both Joel and his family, my family, we are both on health sharing plans. And not because it's like the greatest thing since sliced bread, but because it just offers the best balance, I think, of affordability, married and coupled with coverage. And so our annual premiums. And technically they're not premiums because this is not health insurance. I think it's technically called like a household portion or household share. But those quote unquote premiums are far less than they would be if we were to get a plan on the exchange. Our family pays something like a little over $4,000. And the last time I checked, we'd be paying in like the mid 20 something thousand dollars range just for family health insurance coverage.
Joel
That's like, that's table stakes too. Like I said, that's like before going to the doctor. So you're saying, okay, just from a 20, 26 perspective, can we afford $22,000, $23,000 more money, dude. And so much. I think most people, including ourselves, are gonna be like, ah, no, we can't. We can't do that. Yeah.
Matt
And I will say our families are mostly healthy, so our healthcare spending beyond that, it's been pretty reasonable. But still there is a degree of risk, of additional risk that we're taking that we're shouldering ourselves in order to get these savings. I think not everyone who's listening is going to agree that the trade off is worth it, but for us it's the right move.
Joel
It makes me think of what deductible you keep on your home insurance. Let's say similar. I'm taking on a much higher risk by having the percentage based deductible and I've gotten bit in the butt by that in the past. But I'm hoping that and all the statistics would show that I am likely to benefit from it over time. But for a lot of people, they're like, I just, I can't stomach it or I don't have the savings to actually back me up in case that something were to happen in my house. So that is an important thing to take into consideration. And Josh mentioned asking local hospitals for cash prices. That's great. That's certainly part of the repertoire you're going to want to instill if you go with health sharing.
Matt
I love that.
Joel
Yeah, if you kick health insurance to the curb, you'd want to do the same. But of course that's like the riskiest endeavor you can make. But as he alluded to specifically, like catastrophic injury or a big old diagnosis, that is the main reason to have some type of coverage that goes just beyond the cash that you have in savings. That's the whole reason we use health sharing companies. Yeah, yeah.
Matt
It acts as like this backstop in case the worst were to happen.
Joel
And it's not like with health sharing, you're getting substantially discounted doctor visits like you do a traditional insurance. There is no like super duper low co pay. Right. Most of the time. So health sharing really only makes sense, I think for mostly healthy folks and families who really are attempting to protect against worst case scenarios. Also, I would say get familiar with the fine print about what is and isn't covered. And this varies from different health sharing companies to another. Preventative care, routine care, dental and vision and more are often excluded from the share amounts. So you're talking about having to pay for those out of pocket before you even get to the point where you're submitting bills for sharing. And just for people who have a really low income, don't forget about Medicaid if your income allows you to qualify.
Matt
Yeah, yeah, you mentioned some of the details. Keep in mind too. So we are specifically with Medishare, which has been great, but there are certain requirements that they institute because it is a faith based health sharing plan. And some of all the, all of the original health sharing plans were faith based, which is a part of how they were able to get costs so low. Though that being said, there are also for all the folks out there who aren't interested in something that's faith based, there are a number of different secular health sharing plans as well. Sedera is I think the first one and it's been around, I think the longest. But there's a new one evidently that's kicking butt too. Zion, have you heard of this one? No, but evidently it's pretty great as well. So there are options out there that don't have as restrictive requirements as some of the more faith based health sharing plans. And so those are options for a lot of folks out there too.
Joel
The other thing I tell people when they ask about health sharing, from my experience, Matt, is I've barely kicked the tires, to be honest. Even though we've been on Medicare for a long time, we've not had a major enough healthcare expense where we're running over essentially our deductible, the household portion you mentioned. So like, will it pay out in the event of an emergency? Like from what I've read and seen, like, I'm pretty sure they will if we follow the rules.
Matt
Yeah. And anecdotally, like, that is a risk too. We've got friends who have hit like, who approached it more as traditional health insurance and set their it is ahp, annual household portion. And they had that set pretty low. And it's like, all right, we gotta rebuild the Achilles tendon that I blew out. The girls need to get their adenoids removed. These are specific examples from a specific family that I'm thinking of. And they had zero issues. So granted, that's anecdotal, but that's how it works.
Joel
Yep. We mentioned also the lack of regulation as a downside of health sharing. But it's also, that's why traditional health insurance is superior, essentially because they're going to, they're going to pay out, right? Like, well, I say that they should pay out. Right. It's also the reason though that they can exist and the costs are so much lower.
Matt
So it's that health sharing doesn't have the regulations placed upon it.
Joel
Yes, it's the heaps of.
Matt
You can't technically call it health insurance.
Joel
Right.
Matt
There's no regulations, but that's a part of why it's so affordable.
Joel
It's kind of like a swim at your own risk zone and no lifeguard on duty. Right. But it's the heaps of red tape that are just a part of the reason we're in the conundrum that we're in to begin with. I remember back in the day, Matt, healthcare was essentially regulated by the states. A lot of our younger listeners won't remember this, right.
Matt
But way back when I was 22.
Joel
It was uphill to school both ways, guys too, and a lot of people really could get a policy on the open market. I was able to when I was young, starting my first job, I was part time, didn't have access to health care to buy my own policy on the market for like 100, 110 bucks a month, something like that. And while government involvement and rules have made it easier for people, especially with pre existing conditions, to get coverage, more rules have created an environment of rising prices for everyone, including healthy young people. So I guess when it comes down to it, it's like you need the great job with the health, great healthcare benefits. We're only more tied to health coverage from employers than ever before, which is not the best thing for the dynamism of our country either.
Matt
That's true and I'm going to try to stay as apolitical as possible here. But I think a lot of folks have seen the chart that shows the prices of certain goods and services over like the past number of decades. And what are the services, Joel, that lead the pack that are at the top of the chart?
Joel
Healthcare and college tuition.
Matt
It's healthcare. I love this because they're all h, it's healthcare, it's higher ed and it's housing. And what we're talking about here is to the extent that the government gets involved, we see prices go up. And why is that? It's almost as if there is less incentive for these sectors to innovate or to keep prices low when there are in some cases direct subsidies being paid or just the risk being offloaded these industries by the government saying I got your back. I'm specifically talking about housing. Well, same thing with federal student loans as well. And what do you see at the opposite end of that chart? Electronics. You see televisions have decreased so much in price, like toys. Electronics. Cell phone. Cell phone service. You see the sectors and the industries that have been allowed to innovate on their own without government involvement because they're trying to win over as many customers as possible. And what that also means though, is that you get products that are so much better than they were 10, 20 years ago. And I don't think the same can be said for some of the, I don't know, some of the healthcare services, higher ed housing. I don't know. I guess there's an argument to be made there that the US is certainly leading the pack when it comes to health innovations in health care.
Joel
You could point to lasik though, as being essentially outside of the traditional healthcare system. You've seen advances, you've seen price decreases, you've seen a lot of competition in that space, and we don't have much of that in most of the healthcare system.
Matt
Yeah. It's almost as if these industries have been de. Incentivized to be competitive and to. Yeah, what, woo customers over to what it is that they're offering.
Joel
And I don't know what the overall solution is. I don't know that there is one solution. But right now it's kind of as a how to money listener, it's like doing the best you can in an environment that's like fraught with peril. Yeah. So, Josh, I. I don't know. We would say there are a lot of good reasons to choose health sharing plans if you're kind of find yourself in a position of mostly being healthy and having savings on hand. It's not for everyone, though. All right, let's get to another question, Matt. Let's talk about rental properties and how to make sure you're not putting yourself at risk when you own them.
Ad Voice
Hey, Matt and Joel, this is Andy from Utah. I've got a question about rental property liability. We have a duplex and a single family home currently set up as long term rentals and another single family home under renovation that we're hoping to have ready to go in the next couple of months. We own these properties outright, no mortgages, and they're fully insured. I'm wondering, with all of your properties, do you hold each one in an individual llc, have a single LLC for all the properties, or just keep them under your personal names? I've heard recommendations that you need to hold each one in an individual llc, but I'm wondering if that would actually hold any legal protection in the event of a lawsuit. What do you think? Thank you for being open and helpful as we all come up with strange questions from our individual experiences. Have a great day.
Matt
Joel, do you think we should have gone with the Stranger Things theme for the ask howto money questions? Did you watch any of the later seasons?
Joel
No. Yeah, I Just I kind of lost interest. I love the first season, first and second. And then it just got a little.
Matt
Too, a little too weird. Little.
Joel
I'm a little sensi. Matt.
Matt
Yeah. I forget which season it was where it turned a bit more horror.
Joel
Yeah. Well season I did watch some of season four and I was just like, yeah, it was too much.
Matt
When they're getting elevated. Yeah, elevated. What do you call it? Like levitated.
Joel
Yeah, a little creepy.
Matt
That's when it got freaky.
Joel
I hate horror stuff, man. I just can't.
Matt
That's when it took a turn towards the horror as opposed to the nostalgia. The 80s ride your bikes around the neighborhood.
Joel
The mystery, the.
Matt
Yeah. Ham radio. It's like, oh, I can get behind all that.
Joel
I don't want to see. I know some people, bones break, kept on loving it, but not me. Okay, let's get to Andy's question and yeah, please do by the way, record your strange questions, send them our way. We love to hear money questions and we love to hear your weird ones if you got them. And that's just recording that voice memo by the way And Andy's question. Man, this, this is an important question for landlords. The more you build wealth and the more liability you take on, the more you want to consider how to protect that wealth. It's kind of a success tax of sorts, but one you're going to gladly fork over money for because it's creating essentially a floor underneath you that you can't. That's going to protect you from sinking into the abyss. Ideally we'd be funneling all our extra money into income producing assets. But some of it is truly best spent ensuring that we're not left destitute. This is where insurance products come in. They make sense, right, where life insurance, so our family isn't left us to long term disability insurance so that if we lose our job, which we're actually going to talk about in just a little bit so that we're not left without any income at all. And the same is true for landlords as well. It's important to be cognizant of those things.
Matt
That's right, yeah. And there are multiple approaches though that you could take. Andy putting each property in an individual llc. It's seen as the most like bulletproof, buttoned up approach. But it's also not a surefire way to get full protection.
Joel
It's.
Matt
It references this classic case. I think it was in New York City where a cab owner, he had multiple cars and so he put each cab, each car in its own LLC as to be able to basically protect and shield all the other cabs from any liability where one of his drivers to hit somebody. And it held up. There's like this classic Supreme Court case where in fact the corporate veil. It held. That's what it's called basically. So the corporate veil, but which is.
Joel
Funny just to think about each car being its own little business. Yeah.
Matt
I mean, how ahead of its time was it? Is that not exactly how Uber's function today? But by doing that, it's going to ensure that if you are part of, let's say, a contentious lawsuit from a tenant, that you're not putting your, not only your other properties, but specifically your personal property at risk. But it also adds complexity. And one argument that we've heard against putting a property that's been in your name into an LLC is that it can trigger the due on sale clause. It's not common, but if you transfer legal ownership of the property, there's a chance that your lender is going to enforce that clause. It's not super common for that to happen, but it is possible. It's something that it's a risk worth knowing and it's something that keeps folks that keeps those properties in their, in their name.
Joel
Yeah, I remember having, in addition to.
Matt
Those low rates, mortgage rates that they were able to secure as individuals, I.
Joel
Remember having lawyer friends frighten me into the idea of putting my properties into individual llc because that was a real possibility looming over my head. And I was like, yeah, not going to do that then the way you're talking about it. But it also does appear like that is not something that happens regularly. But I think that's probably the reason that I haven't put any of my properties into an individual llc. But Andy also said he owns his properties free and clear. You're not dealing with a lender, so this isn't something that's over your head. Matt, we have debt on our properties because it's low interest rate debt. We're happy to keep it around while putting our money in other places. But an LLC makes a ton of sense in your case if the cost is reasonable. Talk about the success tax. Depending on where you live, you could find that the LLC is either fairly inexpensive or incredibly costly. You won't be surprised to hear this, but if you live in California, you can be talking about much higher fees essentially for having an LLC on your property. So I think it's like 800 to $1,000 a year. That's expensive, but it's so Much less in many other states like Utah, which is where Andy lives. I think it's like 50 to 100 bucks a year.
Matt
That's so much better.
Joel
That's right. So an llc. I love that, especially since you own these properties outright, could be just a brilliant move for you.
Matt
Yeah, brilliant, but also not bulletproof. I said that earlier, right. About it being bulletproof. It's not fully foolproof because there are different things that would allow the piercing of the corporate veil. For instance, if you commingle funds, if it's not held entirely separate, if there's negligence, like it doesn't matter if it's in its own llc, they can still come after you. And so let's talk about, Joel, what you and I prefer, what we have done, which is an umbrella policy, and simply put, like a 1 million or a 2 million dollar umbrella policy, it can give you just peace of mind, give you some holistic coverage for a whole lot less money, a whole lot less complexity as well. And the chances of you being sued for a bunch more than that, actually, I guess you can get sued for however much you want, but the chances of you getting a judgment get placed against you is pretty small beyond that 1 or 2 million, I think. And so, I mean, it's my belief that this is the best route for most landlords to go. If you're smaller mom and pop landlords like us, it's a different story though, if you have a whole lot more properties on hand and a lot of different real estate professionals out there. If you head over to biggerpockets or even our buddy Chad Carson, they talk about this as you ramp up, as you start taking on more bigger complexes like apartment complexes and things like that, they encourage more clumping. Right. And so it's just like, okay, we're going to have all these properties in this LLC. I guess if it's one that's really high $, where you're dealing with a whole lot of folks, that might be one where you consider placing that within its own llc. But it's something that you can ramp up. And if you are just a mom and pop landlord as an individual, I would certainly be looking more to the umbrella coverage first before considering more complexity with the additional LLCs.
Joel
Yeah, for sure. All right, we got more questions to get to, including one about what to do if your employer drops their 401k match. We'll get to that and more right after this.
Matt
All right, buddy, we are back from the break. It is now time for the Facebook question of the Week, which is from Tyler this week. And he writes, my previous employer gave me a 100% match on up to 6% of my 401k contribution and it was wonderful. I left them a few years back for another company. By the way, I'm much happier at my new job. However, my new employer offered 4.5% match and they just announced a drop to 3.5%. So first question, has anyone else seen decreases in their 401k match for next year? It's the first time I've taken a match decrease in my career. Second question, with this change where you invest your retirement dollars at all? Given this news, I'm now getting almost half the match I used to at my previous employer. What you think, Joel?
Joel
Always crappy to have a perk reduced like that, especially taken away.
Matt
It hurts. It hurts more.
Joel
I think it's going to obviously hurt even more. Specifically for how the money listeners who are just like I'm gung ho about investing more, getting the full match and growing my, growing my net worth and to see be like, oh man, there's like 3 or 4% less at my disposal from my employer that I can take advantage of. That sucks. That's hard to stomach I think especially for people who think the way we do. I mean, I think one of the things that Tyler mentioned is that he likes his job. I think that's great. I think enjoying your work is better than having a killer match. Still, it's nice to have both. But we are seeing more generous employers dial back a bit on 401 contributions. Tyler's not alone in this. I do think that's important to note. Don't assume that everybody's doing it, but also don't assume that you're the only one. We've seen some employers, I've got a friend, Matt who was telling me that his match was eliminated altogether. Yeah, that's even tougher to stomach, particularly in industries that are having a tougher time in this economy. I think we're seeing it more on that front. Which changes the calculation for individual investors about where and how much they stick into that tax advantaged retirement account.
Matt
Yeah. So if you were to not get any match, that makes the Roth IRA a better first option in most cases. I think getting a reduced match can mean just dialing back a bit on those 401 contributions so that you at least get the full match. But then putting more of your money inside that Roth instead I think is a good option. If you're not maxing out your Roth Ira, I think that would be your best reaction. And I'm assuming like his second question was, you know, does this change where you invest? I'm assuming that's what he's talking about. Like what account?
Joel
Not individual funds or anything.
Matt
There's a part of me that wonders though, if he. Because he says where I'm like, wait a minute, are you talking about the. I wonder. And I don't think this is the case. But if there's at all any doubt, Tyler, as to the future of your company based on. You shouldn't really be investing your retirement dollars within your company stock to begin with. Like, yes, if there's a discount, get the discount. Hang on to it as long as you need to.
Joel
Espp. Yeah.
Matt
But then beyond that, you unload those and then move to a fully S&P 500 diversified index fund or a total stock. A total stock market index.
Joel
I don't think that's what he's getting at either.
Matt
I don't think so. But if it is, I wanted to throw that out.
Joel
Now is definitely the time to reconsider. And the last thing I want to mention is to not forget about your hsa if you have access to one. Oh, yeah, it's just the best account from a tax perspective. If you're maxing your Roth, if you're getting the full match, your HSA should be the account you prioritize next before you stick more into your 401k above and beyond that reduced match amount. The HSA is just, man, the idea of never paying tax on the money that goes in, never paying tax on it when it comes out hard to beat, and being able to grow it by investing it in the meantime, it's. Yeah, it's hard to beat. So why? It's one of our favorite retirement accounts. So Tyler, make sure to check that one out. All right, let's get to a question from Anonymous. Who says I need to purchase a long term disability policy and a life insurance policy. Any recommendations for finding the right policy? Are brokers a good option?
Matt
Ooh, I like brokers. But Mr. Or Ms. Anonymous, I'm glad you are asking this question because long term disability insurance is underrated. We talk regularly about term life, rightly so. But long term disability is a worthwhile consideration as well. But it's not even on most folks radar when the stats show that one in four folks will be unable to work for at least three months at some point during their working life. So you think through how much money you could potentially blow through and you're taking on a pretty big risk. And so if you are dependent on your income and most folks are having long term disability is going to provide some real financial relief if you were to be out of work for an extended period of time. So yeah, this is just putting this on the radar for more folks out there who have not ever considered long term disability.
Joel
Most people think, oh, I got a short term disability policy through my work, I'll be just fine. And that can be helpful. But it's not enough. Right. If you're out of work for an extended period of time. So I think, yeah, your message is don't sleep on long term disability. It's worth considering, it's worth shopping around for. But it's also not cheap. A lot of folks are going to find it.
Matt
That's the biggest downside, man.
Joel
Yeah, like maybe saving up additional money in saving is better for them than having a long term disability policy and taking on kind of that risk. Because you're talking about forking over between 1 and 3% of your annual salary for one of these policies. Start looking, see if maybe your employer offers a discounted policy. The downside though of that is it doesn't go with you if you leave. Policygenius is a great place to check as well. You mentioned getting a life insurance policy, a term life insurance policy through a site like policygenius. That's a great place to look. And contact a local broker too. Right. Shop around because you're likely to find that prices vary wildly. So yeah, check the big sites, check with the local broker and just see where you can get the best product for the best price.
Matt
Yep. Have you ever had a long term disability, Joel?
Joel
I haven't.
Matt
Yeah.
Joel
I'm more a fan of self insuring and so I think I'm more willing.
Matt
To take that risk myself. And the biggest hurdle is that that is just the price point when you're socking away thousands of dollars every year. Like I would rather take that money, pay myself and increase my emergency fund. Right. So maybe you're thinking I've got three to six months. All right, well maybe for you, if you are thinking, well, shoot, maybe long term disability is something I should consider. Maybe for you that means your emergency fund looking more like 9 to 12 months worth of living expenses. And that's literally what Kate and I did a number of years ago. So back when I was a full time photographer, I don't know if I've ever shared this story, Joel, but when I was a full time photographer, I had something going on with my eye, which is. You're thinking, oh, yeah, that's probably pretty.
Joel
Bad if you're a photographer.
Matt
And that's what, better than your pointer finger, I guess. I don't know. You can switch fingers. You only have two eyes. But that's when we said, you know what, maybe we'll kind of ramp up how much money we have on hand. That was a risk that, again, that we were willing to. To take. But that's one of the first times that got me thinking about maybe things go south here. We certainly want to make sure that we are prepared. But your family situation also has something to do with it, because in my case, I had a wife, a partner, who would very gladly work if I was not able to. I don't know about gladly, but she'd be willing to step up and while.
Joel
You sat there and watched sports with your one good eye.
Matt
Yeah. Work some extra hours if. If she needed to. But if you're flying solo and it just comes down to you and your income. Yeah, that's another consideration as well. There's just a number of different factors here that go into whether or not this is a risk that you can take when.
Joel
If you start shopping for a policy. It's also really, really important to look at the fine print. Like, does your policy adjust for inflation? Does the policy kick in if you can't do your own specific job, or if you can't do any job, what percentage of your pay will it cover? Is it like 50% of pay? 70%? How long would the payout last? Right. If you became disabled? Is this a cap after five years or something like that? Can the premiums increase? Like, these are all the sorts of questions you want to be asking and comparing policies against each other if you're looking to get one. It's not just all about getting the lowest possible premium price. Right? Because if the coverage is too flimsy and it's not doing what you need it to do, then it's not worth the price. Even if it's a cheaper price. That's right.
Matt
So we hope that helps. Joel, let's get back to the beer that you and I enjoyed during this episode, which was an experimental shift. This is a New England ipa, a beer by Incendiary Brewing, donated to the show by Headmaster Brewer. Actually, I don't know if he's the headmaster, but he's the owner or he started the brewery.
Joel
Sounds like he's the head of a school too, huh?
Matt
Head of a school.
Joel
Headmaster.
Matt
That's what they call.
Joel
Right.
Matt
Wait What'd I say? Did I say headmaster or head brewer?
Joel
Headmaster. Oh, he's the head brewer and the master of his own domain.
Matt
I'm thinking about Hogwarts or something over here.
Joel
This.
Matt
So he explained that every month with this beer, they rotate the hops and they do something different. And so that's why this is an experimental ipa.
Joel
Well, makes me want to try more of them.
Matt
Yeah.
Joel
Because I'll be honest.
Ad Voice
Yeah.
Matt
What'd you think? This is great.
Joel
Like, I think I like whatever experimental hops at least were in this one. It has some tropical notes, but in the right way. Not these, like, overly, like, fake juicy tones. It just tasted like the hops, whatever hops are being used in the making of this beer shone through incredibly well. Yeah, it was not overly sweet or fruity. So to me, the fact that, like, hoppy in the best way. Not obliteratingly bitter, not overly sweet. Well balanced. Well balanced. Love this one.
Matt
Yeah, you said fruitiness. I almost picked up, like, a muscadine, like, hoppy hoppiness to it, like, along with, like, the vegeta vegetal notes. But, yeah, I don't know. I kept coming back to Muscadine, but you could tell this was a bigger. A bigger ipa. It was a bit boozy, had a lot of flavor packed in it, but. But really good. And I'm glad that you and I got to share one today, my friend.
Joel
Same here, pal.
Matt
All right, let's wrap it. You can find our show notes up on the website@howtomoney.com that's going to be it for this episode. So until next time, Best friends out. Best friends out.
Podcast Announcer
This is an iHeart podcast. Guaranteed Human.
In this “Ask HTM” episode (#1090), hosts Joel and Matt answer a diverse set of listener questions that range from practical strategies to manage surging healthcare premiums and properly insuring rental properties, to purchasing long-term disability insurance and the challenges (and opportunities) faced when suddenly coming into a nine-figure fortune. Throughout, they reinforce their mission: providing unbiased, jargon-free guidance to help listeners make thoughtful money moves, no matter their situation.
[10:16 – 24:28]
[25:50 – 37:31]
[38:02 – 45:33]
[45:49 – 49:49]
[49:49 – 54:09]
$300 Million Windfall – Planning & Passive Income: [10:16 – 24:28]
Healthcare Premiums Rising – Insurance vs. Health Sharing: [25:50 – 37:31]
Rental Property Liability – LLCs vs Umbrella Policy: [38:02 – 45:33]
401(k) Match Decreases – Where to Prioritize Retirement Savings: [45:49 – 49:49]
Long Term Disability & Life Insurance: [49:49 – 54:09]
Casual, approachable, peppered with humor and relatable anecdotes (beer reviews, family life, pop culture references). Advice is actionable, candid, and delivered with humility—especially when tackling a question as extreme as managing $300 million.
For listeners in a hurry:
This episode covers high-stakes money moves (for both everyday folks and the ultra-wealthy) with grounded, judgement-free advice on navigating big financial transitions, market realities, and systemic challenges like healthcare access. Listeners walk away with practical next steps tailored to wildly different circumstances—from cash-strapped homeschooling families to accidental decamillionaires.