Ask HTM - Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement #1066

Summary

How To Money – Episode #1066: Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement

Date: November 24, 2025
Hosts: Joel & Matt
Podcast: How to Money (iHeartPodcasts)

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Episode Overview

In this “Ask HTM” episode, best friends and co-hosts Joel and Matt tackle a new round of listener questions. They focus on three main topics:

• The ethics and financial implications of getting a “free” roof through insurance
• Rebalancing investment portfolios away from tech/AI in light of industry trends and personal risk
• Understanding and maximizing Health Reimbursement Arrangements (HRAs) versus HSAs

The episode blends practical financial guidance, ethical considerations, and a healthy dose of the hosts’ characteristic banter—plus, impromptu discussions about mustaches and bourbon barrel–aged beer for good measure.

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Key Discussion Points & Insights

1. The “Free” Roof via Insurance Claim — Ethics & Consequences

Listener Question

Tim from Illinois asks about companies offering “free roofs” after storms—should you take advantage since everyone’s rates go up anyway, or is it unethical?

Discussion Highlights

• Pervasiveness of Offers: Both hosts receive frequent unsolicited texts/flyers from roofing companies promising insurance-funded replacements.
• Ethical Dilemma:
  • Filing a dubious claim is likened to taking shampoo bottles from hotels: just because you can, doesn't mean you should.
  • Joel: “Would you feel OK knowing you got a new roof even though you didn’t have real damage? It feels like cheating.” [13:10]
  • Matt: “If everyone does it, it leads to higher rates for all. It's why we can't have nice things.” [14:28]
• Quality Risks:
  • Many companies are “fly by night” operations chasing insurance payouts with little accountability.
  • These companies may provide shoddy work—less incentive for quality since they don’t rely on long-term local reputation.
• Financial Consequences:
  • Filing a claim you don’t really need will increase both deductibles and future premiums (affecting your Clue Report and ability to shop insurers).
  • “If you truly experienced hail damage and you need to file a claim, do it. But if it’s a bogus claim just to get a new roof, don’t.” – Joel [14:10]
• Personal Responsibility & Collective Action:
  • The tendency toward “lawfare” and gaming the system is contrasted with simply doing the right thing.
• Big Takeaway:
  • Only file an insurance claim for genuine damage—financial and ethical consequences make “gaming” the system a losing proposition.

Key Quotes

• “This is why we can’t have nice things.” — Matt [14:28]
• “Just because everyone else is jumping off a bridge, doesn’t mean you should do it too.” — Joel [12:15]

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2. Investing: Rebalancing Away from Tech/AI & International Diversification

Listener Question

Steve is in “Coast FI” and wonders about shifting new investments away from tech/AI-heavy funds (e.g., VTSAX/US markets). Is he overthinking the AI bubble, or is it smart risk management?

Discussion Highlights

• Current Situation:
  • Steve and wife maximize their retirement contributions early each year. He’s concerned about forced, early retirement if AI wipes out his business and is wary of an “AI bubble” in market performance.
• Not Market Timing:
  • Matt clarifies: “This isn’t knee-jerk market timing. Steve’s risk profile is genuinely changing as he gets nearer to wealth preservation.” [38:31]
• Diversification Strategies:
  • Recommends gradually shifting new investment dollars (not selling everything at once) into value or international funds to balance tech/AI exposure.
  • “Slowly, gently moving the rudder as opposed to jerking the wheel.” — Matt [39:23]
• Emotional Clarity:
  • Visualize your portfolio after a 30% drop or gain to assess your risk tolerance.
  • “Doing these thought exercises could be really beneficial… not just imagining the win, but the loss.” — Joel [43:02]
• Cash Reserves:
  • As retirement approaches (planned or unplanned), holding extra cash is wise to avoid drawing on your portfolio in a downturn.
• Bottom Line:
  • Given Steve's risk of earlier-than-expected retirement and tech concentration, it is sensible to rebalance toward less tech-centric, more international and value funds over time.

Key Quotes & Moments

• “Your goal isn’t to maximize returns as much as possible; it’s to be prepared for upcoming changes.” — Joel [41:12]
• “The risk tolerance part is super important, and this is why it’s such a personal decision.” — Matt [41:28]
• “If things go poorly, you might be in business longer. If things go well, you’re ready for early retirement.” — Matt [37:12]

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3. Rothification & Retirement Account Strategies

Listener Question

Vicki from Ohio, making ~$69K/year, maxes out her HSA & Roth IRA. She wants to know about converting a 401(k) to Roth to further “Rothify” her savings.

Discussion Highlights

• Kudos:
  • Both hosts celebrate how much Vicki sets aside: “You are a total boss!” — Joel [21:58]
• 401(k) Roth Conversion:
  • Check for Roth 401(k) Option First: ~90% of employers now offer it—use this if available.
  • If Not: May be eligible to roll over traditional 401(k) funds to a Roth, depending on plan rules (look up “in-service rollovers”). Be mindful of the tax hit!
• Tax Consequences & Timing:
  • Carefully plan Roth conversions to manage the tax bill, possibly spread conversions over several years.
  • Consider waiting until income drops (e.g. after retiring) for more favorable conversion rates.
• Taxable Brokerage Accounts:
  • If all tax-advantaged accounts are maxed, investing via a taxable account is still worthwhile.
• Catch-Up Contributions:
  • Reminder for older listeners: additional contributions allowed after age 50.

Notable Quotes

• “If you can do a Roth 401k, that’s the simplest path forward.” — Matt [25:28]
• “Just know you are not getting a deduction for your 401k contributions if you convert.” — Matt [27:09]

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4. Understanding Health Reimbursement Arrangements (HRAs)

Listener Question

Angela asks why HRAs aren’t discussed more on the show, and how they compare to HSAs.

Discussion Highlights

• Scarcity: HRAs are less common than HSAs or 401(k)s, so rarely mentioned.
• How HRAs Work:
  • Fully funded by the employer for employee healthcare expenses; employees submit receipts for reimbursement.
  • Money belongs to employer and may not be portable if you leave or unused by year-end.
• Can You Combine with HSA?
  • Sometimes, but depends on HRA version (“limited purpose” HRAs work with HSAs; standard HRAs generally don’t).
• Maximize the Perk:
  • Use up available HRA dollars before year-end or prior to leaving a job.
  • If both options are available, weigh employer generosity and your personal/family needs.

Notable Quotes

• “If you have a really generous employer offering a substantial reimbursement for you every year, that's a pretty sweet perk that I'd want to take full advantage of.” — Joel [55:43]

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5. Bank Switching for Higher Yield Savings

Listener Question

Jordan wonders about chasing higher yields by moving money between online banks as rates change.

Discussion Highlights

• Host Experience:
  • Matt has been with Ally for nearly 20 years; both appreciate great customer service and features.
• Soft-Switching as a Middle Ground:
  • Moving a portion of your savings (not all your banking) to a higher-rate account can make sense (“soft-switching”) rather than going through the hassle of a full switch for marginal gains.
• Consider the Actual Benefit:
  • For a difference of 0.5% APY on $20k, the upside is limited; balance the hassle with the real reward.
• Pro-Tip:
  • “Not an irreversible decision. Give it a shot, see if it feels worth it. If not—you can undo it.” — Matt [50:54]

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Fun & Notable Moments

• Banter on Facial Hair:
  • The duo spent the first few minutes riffing on growing (or not growing) mustaches and receiving compliments—or spousal pushback. [02:00–03:30]
• Beer Review:
  • Shared a “Bourbon Barrel Aged Imperial Stout Vintage Ale” by Kirkland Signature/Deschutes. Both were surprised by its quality, calling it “high-quality, with unique holiday spices, perfect for Thanksgiving.” [57:38–59:44]
• Pop Culture & LOTR:
  • Jokes about AI companies naming themselves after Tolkien fantasy objects (“Palantir, Anduril”) and whether they understood the original message. [05:10–05:42]
• Good-Humored Age References:
  • “You made yourself sound old yet again, Joel.” — Matt [24:40]
• Celebrity Nicknames:
  • Listener Jordan refers to the hosts as “Mole” and “Jat,” to their amusement. [48:24–48:39]

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Important Timestamps

• 06:54 – Introduction to listener questions
• 07:52–17:10 – Roof insurance claims: Ethics and consequences
• 20:54–30:42 – Rothification of retirement savings
• 31:04–43:39 – Portfolio rebalancing away from tech/AI, hedging, and diversification
• 52:15–56:10 – Health Reimbursement Arrangements (HRAs) explained and compared to HSAs
• 57:38–59:44 – Kirkland Signature Vintage Ale Beer Review

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Summary Table: Pros & Cons of Key Topics

| Topic | Pros | Cons | |-----------------|---------------------------------------------------------|-------------------------------------------------------------| | "Free" Roof Claim | Save money on roof, common industry practice | Unethical if not warranted, raises rates, affects insurability | | Rebalancing Portfolio | Reduces risk, aligns with real-life changes | May miss out on tech gains, more complicated than "set and forget" | | HRAs | Employer-funded, tax-free, low-effort for employee | Not portable, less flexible vs. HSAs, less common/offered | | Bank Hopping | Higher yield possible | Time-consuming, often small gains unless a lot of cash | | Roth Conversions| Tax-free retirement withdrawals | Tax implications in conversion year, must plan timing carefully |

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Final Thoughts

This episode is a classic “How to Money” showcase—straightforward, practical money advice filtered through both financial and ethical lenses, always encouraging listeners to take the responsible, long view. The hosts combine real-life anecdotes, transparent opinions, and guest references to give their answers texture and relatability, with lots of humor throughout.

Hosts’ Core Message:
Make financial choices that serve your whole self—not just your wallet, but your community, your conscience, your future security, and your sense of peace.

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Further Resources:

• EconTalk episode on the ethics of frugality: Shampoo bottles at hotels ([09:02–10:33])
• Interview with Joe Davis (Vanguard): The impact of AI and risk tolerance ([34:13–35:43]; see show notes for link)
• Visualizing risk tolerance technique: “Imagine your portfolio down 30%” — [41:28–43:39]

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Transcript

[A]

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[B]

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Hear that? That's what it sounds like when you.

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Plant more trees than you harvest. Work done by thousands of working forest.

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So do what you need to do, work how you need to work. Sweat moves you forward. Degree is here to make sure that it doesn't hold you back. Degree here for sweat.

[B]

Welcome to how to Money. I'm Joel.

[A]

I'm Matt.

[B]

And today we're answering your listener question.

[A]

Your mustache, by the way, buddy, is looking quite fine. Well, I think we've not talked. Have we not talked about it on the show? I don't think we have.

[B]

Might have mentioned it.

[A]

Maybe early on we joked about it, but it's like full on legit. Well, oh, we did joke about it early on because you're.

[B]

It was a joke in the beginning.

[A]

It looked like a joke. No, it's like, it's just. It's like as thick as your hair up top. And I'm not disparaging either.

[B]

My thinning hair looks great with my not so great mustache.

[A]

With a thin mustache as well. No. How long are you planning to keep.

[B]

It, by the way? I don't know. I'm kind of. I feel like it's one of Our friends recently. One of our mutual friends recently said, you look more like yourself now with that mustache. And I thought that was the highest compliment.

[A]

Honestly. It means that you've gotten used to it. That's what that means.

[B]

And I was like. But I think it was the first time he'd seen me with it. Oh, really? Yeah. And so I was like, all right, if you feel that way and this is your first or second time seeing me, but I think I'm starting to enjoy it. I like me with a mustache better than me without.

[A]

Okay.

[B]

So maybe I'll keep it around for a while.

[A]

So, not to make things about me, do you think I should grow mine out and then we can have dueling. Not dueling mustache, but, like, coordinated sparring mustaches.

[B]

I thought it looked good. It was just that all of your family hated it.

[A]

That's the thing. I even mentioned that to Kate because.

[B]

Was it.

[A]

Maybe it was at Halloween. We're hanging out with some friends. We had a little party, right? And we were talking about it, and they were like, saw pictures. They're like, oh, no, that's decent. And I mentioned it to Kate. She's like, I don't care what they think. What about what I think we should probably move on. Can't just talk about mustaches. I don't think I'm gonna grow mine out.

[B]

By the way, this is literally my first foray into facial hair. It's great. It's going well. I think it's solid, man. I'll keep it around.

[A]

But no, this is another glorious Monday where we're going to tackle some listener questions, buddy. We're going to talk about how there's no such thing as a free roof. You thought I was going to say lunch, didn't you? There's no such thing as a free roof.

[B]

This is an interesting. There's no such thing as a cheap lunch if you bring leftovers.

[A]

That's true. It's another glorious day of eating leftovers as well today.

[B]

Coming up, mine were inferior leftovers today, but still leftovers.

[A]

Another listener. Well, he's worried about AI putting him out of work soon, so he wants to know what he should be doing about that. We're also going to talk about health reimbursement arrangements, which sounds so sketchy. Sounds so. It sounds not legit. Right? It's an arrangement, Joel. It's an. It sounds so informal. That's the problem.

[B]

That's true.

[A]

When you say an arrangement, it just sounds like something that you don't have written down on paper. But that's not the case.

[B]

I'm highly suspicious.

[A]

That's not the case with this one, though. But, yeah, open enrollment. It's still open, so we'll get to that one.

[B]

Plus my question. I'm thinking maybe he needs to go unplug all the machines to run all the AIs. Maybe this is the way around it to kill it in its infancy.

[A]

Oh, yeah.

[B]

Just a thought.

[A]

Okay.

[B]

Go into the heart of Mordor and eliminate the AI.

[A]

Oh, the two towers rubbing off on. How did you just finish?

[B]

So good.

[A]

Yeah.

[B]

Now I'm waiting on the third book.

[A]

Are you gonna immediately start Return of the King?

[B]

Well, I'm waiting for the library to say that I can have it. When they do, I'll read it.

[A]

I'm pumped for you, man. This is a series that I haven't touched in decades, but I'm looking forward.

[B]

To definitely worth revisiting.

[A]

Oh, yeah, I can't. I can't wait to. Well, I want to redo. I want to revisit it with the kids.

[B]

Oh, speaking of AI, you know what it reminds me of? There's, like, many names that are mentioned. The name of a certain object. And there's AI companies named after these objects in Lord of the Rings. There's Andoril, and there is.

[A]

These are defense. Defense contracts.

[B]

Defense contract. Yeah, yeah, yeah, yeah, yeah. So I just.

[A]

I'm like Palantir.

[B]

But I think some of those companies missed the part of the point of.

[A]

The book, it being like more of the.

[B]

There's some highly relational, beautiful moments in the book, and I'm like, oh, these are like defense. They, like, picked out a cute name, but I think it's just, like, a.

[A]

Nerdy way for some of these guys to have maybe signaled to some of the other fans of LOTR that, hey, we're on the same page here when it comes to some of the. Fan. Not fan. I was about to say fanfic. Some of the different stories that we've enjoyed over our lives.

[B]

I just wonder if they fully internalized it in the way Tolkien wanted them to, you know? Yeah, I don't know. Maybe we should move on, though.

[A]

Maybe we should have named our company instead of.

[B]

We should have after.

[A]

After a Tolkien S. Gollum Incorporated.

[B]

That's a hard set of names.

[A]

Schmeagle, llc. No. Let's get to our beer that you and I are going to share today. This is a bourbon barrel Aged Imperial Stout vintage ale by Kirkland Signature.

[B]

Ooh.

[A]

And technically, it's got the Kirkland Sig label on it. But this is a beer by Deschutes. But you can't buy that.

[B]

Deschutes, right?

[A]

Like I don't think so. Literally. Kirkland Sig's beer.

[B]

I love a co branded beer like this and to be honest, many of the Kirkland signature beers have left me wanting and in fact they've been downright not very good. And so I'm really excited to dive into this one. This is a specialty beer they've made. So we'll give our thoughts at the end of the episode. All right, so let's get into listener questions, Matt. And by the way, if you have a question for us, we want to hear it. Just go to howtomoney.com ask or if you want to skip the reading part, just go to the voice memo app of your phone, turn it, press the record button, say your name and what your question is and then email it to us. It won't take long and we'll hopefully take it next week on the show. We'd love to hear from you. All right, let's get to a question. This one is specifically about insurance and I don't know, maybe pulling the wool over your insurance company's eyes. Hey Matt and Joel, this is Tim from Mount Prospect, Illinois. I greatly appreciate all the financial and non financial advice you guys have given over the years. I can honestly say that I am.

[A]

Living an all around healthier lifestyle thanks.

[B]

To you guys bringing up books like the 8080 Marriage and Born to Run.

[C]

My question for you guys today is.

[B]

In regards to these companies going around our neighborhood handing out flyers advertising that they can help you get a free.

[C]

Roof through insurance due to wind and hail damage.

[B]

On the other side of this coin, insurance companies are saying that premiums are going up because of the increase they are seeing in paying out these types of claims. This led to a friendly debate with.

[A]

One of my buddies. We would you enlist one of these.

[B]

Companies since you are already paying higher premiums as a result of others doing.

[A]

It or would you pay for the.

[B]

New roof yourself so you are not contributing to the problem. I look forward to hearing your guys thoughts. Thank you.

[A]

Joel, you know exactly what Tim's talking about. You get these texts as well, right?

[B]

Oh yeah.

[A]

And so I just, I just pulled up my phone.

[B]

Sometimes it's legitimately people just knocking on your door or leaving a flyer in your mailbox too.

[A]

I get more often than not texts like maybe I'll get like two a year as far as folks coming by. But more than off, like more often than not they're texts. And literally in the past month, I just looked. I've had four people reach out and they say, hey, we've got a crew in the area, or we've got an inspector. We'd love to swing by and see if there's any damage to your roof. I don't like it.

[B]

Well, it's about to be five because I'm going to text you later.

[A]

Okay.

[B]

And be like, I'm about the roof. Yeah. It's funny, I had a friend growing up and his dad would do this, but not the fly by night kind of thing. He would literally go to areas that experienced storm damage with this company. And that was his job. Like to go to the part of the country that had just recently experienced some sort of natural disaster and then, you know, work to get quotes for people to get things fixed, which makes sense. We haven't had a natural disaster in our area, Matt. This is not. There was no tornado that just ripped through our neighborhoods causing dam or hailstorm causing damage. And so this is one of those things where, yeah, the question is partly financial, but it's also moral. Right. And this actually reminds me of a recent Econ Talk podcast, one of my favorite podcasts. It's been around for like 20 years, but the conversation was about Roberts. Oh, yeah, he's awesome. And so this one was the shampoo bottles in hotels. And it sounds like the most random conversation, but why is it that we think it's fine to take small 3 ounce bottles of shampoo home with us, but now that hotels have largely migrated to using the bigger wall mounted bottles.

[A]

Which I love.

[B]

Which is great. Probably makes sense from a money saving perspective for them too.

[A]

The pump, you just. But then you don't get to take.

[B]

It home with you. Right. Which I think some people like. The guy that was being interviewed has apparently a treasure trove of these three ounce shampoo bottles. And he loves them. I hate them. They're so hard to get the shampoo out.

[A]

It's why I like the pump.

[B]

It's like the old ketchup bottles.

[A]

Yeah. Trying to get the ketchup out, but even tinier. Yeah, Yeah. I don't like.

[B]

So. But of course, we wouldn't dream of putting the full size bottle in our suitcase. Right? Sure, that'd be cheap. Yeah, exactly. And I think this is a point I get arrested. The whole conversation centered around this point where money saving maneuvers are acceptable, like putting more Money in your 401k to reduce income, and then maybe where others cross the line, like hiding income or lying to reduce your taxable income. And some things are literally just like, could get you in legal hot water. But others are just, we find them repulsive or we know that if our neighbor told us about it, they, that we would be like, oh, dude, I don't know man, that's pretty ridiculous. Like nobody does that. Why would you do that? Yeah, maybe you can get away with it, but it doesn't make it right.

[A]

Yeah, I mean, I think everyone has a different line, which is a part of what makes the frugal versus cheap question so interesting. But I do think that there's always a window of acceptability, like where the vast majority of folks can at least understand why someone would come to that conclusion. That being said, we wouldn't be able to use this method to file a claim with a clear conscience. First of all, many of the companies that do business in this way are fly by night.

[C]

Right.

[A]

And so I think that the chances are that the job is done well, that they do a good job is pretty slim.

[B]

The kind of companies that would try to get you to file a claim for damage that wasn't actually done to your roof or are likely going to be the companies who don't take as much care when they're repairing or replacing your roof.

[A]

I was suspect that they would be a high quality company putting doing it properly. And I think the primary thing is they're just looking for the paycheck from the insurance company.

[B]

Right?

[A]

Like they're waiting on that fat check and then they're moving on as quickly as they can. And so part of that is because.

[B]

They'Re not maybe an actual company who does business in your community, who thrives or at least exists on good reviews from people who live in the community. Right. And if they are more of a fly by night company, that's not what they care about. And if they don't care about community reputation, then it probably means they're not as beholden to how you think of them, which could mean inferior service, the.

[A]

Incentives aren't aligned for them to do a good job. They're literally there to get the project started, to get the check, and then they move on.

[B]

And typically these companies can find something to report that justifies a new roof. Right. But does it really feel like the right thing to do to get them up on the roof to file a report that might or might not pass muster with the insurance company? As my mom would say, Matt, if everyone was going to jump off a bridge, would you do it too? Did your mom ever say Anything like that to you?

[A]

No. And I literally jumped off bridges.

[B]

So the answer for Matt was yes, but she.

[A]

She didn't know I was jumping off the bridges. And it was into a river and. And we would check out the. Actually, we didn't check out the river before we jumped into it.

[B]

That's.

[A]

That's my biggest regret. Looking back. We could have really messed ourselves up.

[B]

Really could have messed up. You always. Yeah.

[A]

You always got to. If you're going to do this, kids.

[B]

Go in the water first.

[A]

Always check the water. Always make sure there's no.

[B]

Yeah.

[A]

Check the depth, make sure there's no trees down there.

[B]

Let's assume there's no water below. Especially if people are jumping off the bridge. Like you're not going to follow them to their demise because everybody's doing it. And I think I was. That was my mom's point. Although you. He might not have understood it. Yeah, it sounds like fun. You lived in my house growing up. But even if, let's say this roofer was to do a top notch job giving you a fantastic roof to enjoy for decades to come, you still pay a deductible, which is far less than the cost of the new roof. But that will also increase your insurance premiums for years to come and your ability to switch insurers to save. Because that claim goes on your Clue report. And that Clue report is kind of behind the scenes that when you say, hey, I'm trying to go from State Farm to Liberty Mutual, Liberty Mutual says, hey, well, you filed that claim with State Farm for the roof. So we're either going to charge you more or not accept you. So that could prevent you from saving money in the future. But I think, really, Matt, you agree with this too. Is my guess is that the most important thing at the heart of this question is it feels like cheating your insurance company. It reminds me of the stories of people just massively abusing Costco's return policy. Hey, I got these tires four years ago. They're bald as a mother now. But I'm going to return them because your return policy says that I can. And everybody who has any sort of conscience or like moral care or qualm, Decency. Decency is going to say, yeah, I don't do that. We don't do that. That's ridiculous. That's abusive of a company that is actually great and offers. Offers a solid product at a reasonable price. So I think if you truly experienced hail damage and you need to file a claim, do it. But if it's a Bogus claim in an attempt to get a new roof that you don't deserve, that you don't need, that isn't truly damaged. Don't do it.

[A]

Yeah. This is why we can't have nice things. That's the phrase that comes to mind when I hear this.

[B]

Right.

[A]

Because people are abusing the system, even though technically speaking it might be allowable. But unfortunately, it's just the tendency of society to be moving in this more lawfare sort of direction where things are contested as opposed to just having character, like doing the right thing. And also, I don't want it to make it sound like that we're like running Tim through the ringer here. Like, truly, if there is damage that has been afflicted upon your roof, then like, yeah, like Joel said, that is totally something that you can do. But there's a difference between, like, the heart of the law and like the. The letter of the law, basically.

[B]

Yeah. And then the heart of the law or that you're getting at here is.

[A]

Not like every time something happens to your roof that you are entitled to a new roof, basically.

[B]

Yeah, well, again, yeah, it's this collective action problem where if everybody does it, it's going to lead to higher insurance rates across the board, but it's also going to lead to higher insurance rates for Tim or for his friend. He said this was a conversation with his friend. One of you two, whoever does this is going to see increased premiums, you know, for themselves as well. Totally, yeah.

[A]

It's costing all of us money. And I totally get the impulse to, you know, take the smooth talking rover up the inspector, take them up on their, hey, let me hop up there. I'll take a look around, see what's going on. But you know, I think some folks unwittingly file a claim, they move forward. But this is ultimately why we're seeing rates rise across the board for all of us. But one thing to keep in mind, know that insurance companies, they have gotten wise to this game and they are pushing back a bit more forcefully now. So even still, despite the allure of a quote unquote free roof, I think it's ethically dubious. And on top of that, aside from the ethics, the. From a financial standpoint, it could end up coming back and biting you in the butt.

[B]

And the reason, I think the roof part, if so, is a big part of this, Matt, is because roofs are expensive. Like the idea, depending on the size of your roof and what material you're using, I think at this point, $10,000 would be cheap for a roof. Right? And I haven't replaced a roof in the last few years, but like, could be, especially if you have a, a big house covering a lot of square footage, you could be talking about twenty plus thousand dollars to replace a roof. And so this feels so enticing, like, oh, this is a 20 to 30 year product that's going to, it's going to last that long. Yes, I know I'm going to have to replace it soon, but man, if I can get the insurance company to take this headache off my hands for me, that's a lot of money I'm going to save. So it's appealing from that perspective, but it's one of those things as a homeowner that you have to be budgeting for along the way is the replacement of those more expensive systems of your home, the roof, the H Vac, stuff like that. So yeah, well, nobody wants to fork over the money. That's kind of part of what comes along with buying that home in the first place.

[A]

You got to set up that sinking fund. But Joel, we got more to get to. We're going to hear from a listener and he thinks that AI is going to run him out of business. We'll get to that and more right after this.

[B]

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[A]

It makes me think you mentioned kids, Joel. I might be done having kids at this point, but my friends, my neighbor aren't. I've got family members who have a fresh baby at home as well and it is such an amazing season of life. But those changes should also bring about a reassessment of whether or not you've got your estate planning ducks all in a row. Trust and will makes it simple and straightforward. Their easy to use website is simple to navigate and plus all your information, all your documents, they are securely stored with bank level encryption.

[B]

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[A]

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[B]

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[A]

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[B]

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[B]

All right, we're back from the break. Got more of your questions to get to Matt. Let's take a question now from a listener who wants to rothify more of.

[A]

Her money Hi, Matt and Joel.

[B]

This is Vicki from Ohio.

[A]

I'm an average earner, around 69,000 a year. I max out my HSA and my Roth every year. I wanted to know if I can put money into my 401k at work and transfer it over, do a Roth conversion to my Roth. Thank you for your help. I really enjoy your show. I've learned so much. Bye. All right, Vicki, first off, can I just say that you are a total boss. The fact that you are. She's got an annual income of around $70,000 and she's maxing out her Roth, Ira and her HSA. And she didn't mention the family. So I'm assuming that she's talking about the single version of the HSA for an individual as opposed to a family that's over $11,000, which is not easy in total. Yeah, that's not easy to do with 70,000. $70,000 income. And so, Matt, so much Riz, as.

[B]

The kids would say. Matt.

[A]

Yeah, I don't know. I think that was.

[B]

I like to use those terms, really, 20, 24 inappropriately, just to make myself sound even older, actually, which is what.

[A]

It in fact does.

[B]

That's my favorite thing to do. So now that people know I'm truly middle aged. But yeah, no, for real, like maxing out both those retirement accounts on that salary is incredible.

[A]

It's really impressive and it just adds. I hope it's encouraging for a lot of folks who hear this. They hear that and they're like, oh, man, that's about what I make, actually. Oh, wow, that's possible. She's doing it. She's been doing it. And on top of that, she's looking to do even more.

[B]

It makes me think of my conversation not too long ago with Hope from under the median. And their family has essentially made average of $40,000 for their entire working lives. And she talks about how they were able to buy a home in cash and pay off a home quickly. Like they just. All the things that they were able to do and that's such an inspiring episode because of their attention to detail and frugality. Not everybody wants to go out there and find a job that's incredibly stressful, that's going to pay them 150 grand a year. Because let's be honest, sometimes the more money you make, it means the more you have to trade off living your life. And so Vicky is. I don't know what she's doing, whether she loves her job or not, but I will say she's from A numbers.

[A]

Standpoint, she's doing a great job. Totally crushing it.

[B]

Yes.

[A]

It does make me think, too, she's from. She said she's from Ohio and Ohio has a lower cost of living rate. Whatever. It has an actual lower cost of living compared to the rest of the country. So I don't know what city she's in, but that's something else too, that maybe there's a quick takeaway here for folks to hear that and think that's it would be impossible for me to set aside that amount of money where I live. Well, yeah, you could also. I'm not saying completely uproot your life, but there are certain things that you have control over and I think it's worth considering cost of living. And maybe Vicki actually, like, lives out in the country, so she's not even in a city. Right. And so she's.

[B]

Maybe for her, this is easy. This is cake. I also think there's something about Midwestern values, and I don't know, maybe that sounds ridiculous, but I do think frugality is kind of like baked into the cake of how Midwesterners function, at least on average. Right. As like a looking from the outsiders. As someone who's visited regularly places like Ohio and Wisconsin, the people I meet there, frugality seems to be less like, dorky. It's more just kind of, oh, this is normal. Where if you live in la, it's like frugality. It's for losers.

[C]

Yeah.

[B]

And so I think there is something to that. Where. If you live in a place where all the heartlanders people don't care if you're wearing a Kirkland signature sweatshirt and jeans versus they better not, because we're.

[A]

Over here drinking Kirkland Sig beer.

[B]

I know, but, like, you're not getting into that in the club in West Hollywood or something like that. So I don't know, maybe it's easier to pull off in Ohio as well for that reason.

[A]

You've made yourself sound old yet again, Josh.

[B]

I know. I'm really good at that.

[A]

You fit your quota for this, for the show.

[B]

Oh, there's more to come. So the accessibility that Vicki's going to have. Right. Is going to help her out, too, if she's attempting to retire early. I don't know if she is, but the HSA and the Roth ira, those are very flexible accounts. But she's looking to do even more, which, of course, we love. And the first thing to note, by the way, is that you. You might not have to do a Roth conversion. Many employers offer a Roth 401k option. Vicki. So that's worth looking into that. I think last I read, something like 90% of employers make a Roth 401k option available. So it's getting pretty ubiquitous at this point, which means you wouldn't have to do anything other than just contribute directly to that account. And you probably should do that if it's available to you.

[A]

Right.

[B]

If you were making like $300,000 a year, we'd probably say stick with the traditional 401k. But given your income level, I think Roth everything is a totally fine, potentially an awesome approach. So if There's a Roth 401K available where you work. I don't know, Matt, I'd be, I'd be strongly considering that.

[A]

Yeah.

[B]

Yeah.

[A]

So check with your, with H R or look into your benefits to see if that's something you can do. Right. Directly contributing to that Roth 401k, that would be the simplest path forward, although it wouldn't help you if you were looking to be able to draw down on some of those contributions if you're looking to retire early. But let's assume, though that your employer does not offer a Roth 401K. And let's just say you want to get more money into your actual Roth ira. To your specific question, the answer is yes. If your company allows in service rollovers, you're allowed to contribute Money to your 401k. And by the way, I hope you're getting a match for doing so, for contributing to that 401. But then you would do a direct rollover of $401 to an IRA. But that is big if, though. And I'll say if you're with a low cost brokerage, a low cost provider, it certainly makes sense to keep it with that company, keep it under the, the same umbrella, essentially. But then what you're able to do is convert the traditional IRA dollars into Roth dollars. It's a few steps, but you can potentially, like Joel said, Rothify those dollars. Do keep in mind that you're going to be paying tax on this. Right. And so it sounds like this is something you're looking to do moving forward. It's not like you've got $75,000 worth of 401k contributions sitting there to where you'd be stuck with a big old fat tax bill all in a singular year.

[B]

But if she does, if you do.

[A]

Keep that in mind, you're going to.

[B]

Have a big old tax bill.

[A]

But just know moving forward that you are not getting a deduction for those 401 contributions.

[B]

Yeah, yeah. I think that's really important thing to mention.

[A]

And taxes are a big consideration when you are looking to change the tax. What is it?

[B]

The tax character of these dollars. Yeah. And when and how much. Like those are really. Those are really important questions. And the truth is, if there is a big lump sum in there, that would push you to think through that in a more holistic way about a gradual way perhaps. Yeah, maybe I do this over the course of a number of years instead of doing this in one fell swoop. And actually, I don't know, maybe because I'm still making money and I think I'll make less money once I retire, maybe it makes sense to actually hold off on some of those recharacterizations from traditional to Roth until I look like I'm making less money to the irs. Right. Because I am, because I'm not working anymore. And that is often a great time. Makes me think of that conversation with Cody Garrett. That's worth listening to as well. Talking about when you turn money that you've invested from traditional into Roth. I think it's really important to think through that so you can pay less tax overall on those dollars over time. We should also mention that so much depends on your current tax bracket and your likely tax bracket in retirement because Roth isn't always a slam dunk, especially on the 401 side. I think the Roth IRA, if your income allows, makes sense for almost everybody pretty much all the time. Roth IRAs are great, but if you think your income is going to increase quite a bit, I think it sways things in favor of the Roth even more. If you're like, hey, I'm making 70 grand now, but I see this path, I'm probably going to be increasing my income significantly. That makes time of the essence to get money into the Roth as many dollars as you can get into the Roth vehicles. Now if your income is going to go up, then I think it's a beautiful thing, a valiant attempt to try to get as much as you can in if you think your income is going to decline, like let's say you are going to retire soon and it's going to go down in a big way. Well, it does the opposite. I think it incentivizes putting money into traditional vehicles, traditional 401, traditional IRA. Don't forget that once you reach the age of 50, you're going to be eligible for catch up contributions. This means you can contribute an extra $1,000 straight into your Roth IRA. At that point in time. And you can put extra into the 401k or Roth 401k if you find you have that available. So take note of that.

[A]

You seen the. Vicky's old, Joel.

[B]

I don't know how old she is. I know I'm old. I know I'm getting closer to that.

[A]

Jill's looking ahead. He's like, ooh, catch up. Contributions, baby.

[B]

That's the only sexy thing about turning 50, in my opinion. Right. Or.

[A]

I don't know.

[B]

I think actually.

[A]

I think there's plenty of great things about turning 50. I'm actually looking even more great. Gray hair in the mustache.

[B]

Oh, yeah, it's coming. But, yeah, being 41 has been surprisingly pleasant. And so I actually. Actually I'm not nervous about aging. And I guess the last thing I would suggest for Vicki is to not forget about taxable brokerage accounts. Because if you're like, oh, man, they don't offer the Roth 401. Well, taxable brokerage accounts are another great way to invest. Yes, you're going to pay tax on the gains, and you're not getting the same tax break that you are for contributing to a traditional account right now or a Roth account in the future where you don't pay tax on the earnings. But that's still a great account if you have more money you want to invest and you don't have access to some of these other great accounts. Or you're kind of capped essentially by the contribution limits.

[A]

Yeah, yeah, you'd be artificially capped if you were to have stopped investing at that point, as opposed to saying, oh, I'll just invest like a normal person in a less tax advantaged way. Joel, let's now hear from another listener. This is a listener who doesn't want to go all in with voo. He doesn't want to go with an S and P ETF all the way. He's looking to diversify. This is a question from listener Steve.

[C]

Hey, Matt and Joel. My wife and I are currently in MoneyGear 7 and assuming nothing changes in my current business, we have already reached Coast Fi. We both max out our 401ks and Roth IRAs on January 1st each year and we dollar cost average into a brokerage account every month. So if nothing changes, we should easily be fully fire in five to 10 years. I'm currently 45 and own my own business, but I'm guessing I have four, five years tops before AI puts me out of a job, forcing me into FI whether I'm ready or not. It's not the worst thing, but I'd hate to have to start drawing down funds to live off of if we're in a recession. My plan thus far has always been to invest solely in VT Sachs, which is a total stock market fund, since I theoretically won't need the funds for at least a decade. But now that I see the strong potential of being forced into retirement early by AI, I'm wondering if I shouldn't be a bit more conservative. On top of this, I'm increasingly concerned that we're in an AI bubble with much of the gains in the market tied to those AI companies. So if AI keeps growing, it puts me out of work. But if it's actually all smoke and the bubble bursts, it cuts into my portfolio. So my question is, would it make sense to start shifting future stock purchases into something more like Vanguard's Value Index Fund? When I look at the holdings, VT Sachs is 38% tech, where VVIAX is only 7.5% tech. So much lower on the tech. My thinking is this would keep me aggressively in the market, but would start diversifying my portfolio away from being so tech heavy. Furthermore, I keep losing faith in the future stability of the US for all sorts of reasons. So I'm also considering diversifying a percentage into Vanguard's Total International Stock Index to protect against the potential of future US instability. I get that this all sounds like timing the market and it complicates things way beyond just dumping everything into VT Sachs. But being at coast fi, I'm willing to trade some of that upside for a bit more peace of mind. All that being said, would shifting to something closer to 50% total stock market, 25% growth, 25% international make sense in my situation? Or am I just overthinking things way more than I need to? Thanks guys.

[B]

Oh, Steve. Oh Steve.

[A]

Do you think he's overthinking it?

[B]

I don't think he's overthinking it. I think he's put a lot of thought into this and I think it's admirable that he's considering not just doom and gloom headlines about what AI could do to the job market or will do to specific sectors, but he's really thinking through long term ramifications of what it means for his particular job, his overall portfolio. This is not a knee jerk reaction when he mentioned not wanting the time to market. That's not the vibe I get.

[A]

No, this isn't, Steve. This isn't a timing thing. But I will say I There is a part of a very Small part of me that does think he's over indexing the whole AI thing because of the fact that it is going to impact him, specifically with his ability to continue his business. And I totally.

[B]

And in some ways you have to. I totally feel that in some ways you have to because it's almost like owning a bunch of company stock in the company you work for and you're like, you're over indexed to this thing, man. And so if you're bread and butter, if your income comes from AI, you might want to not have as much of your investment portfolio tied up in artificial intelligence. So I think that is also another factor on the table. I love this question. And by the way, Steve, I'm not sure if you had a chance to listen to my interview with Vanguard's Joe Davis that came out recently. I think it would be particularly helpful for you. He's put a lot of thought and methodology into what happens if AI crushes or if it's kind of a lackluster and it doesn't really do everything that Sam Altman and those bros are saying it's going to do. He also factored in other major trends into his analysis. And so I get that the bubble talk can be disconcerting, but I think Joe's work can offer some encouragement to stay the course. Which doesn't mean we don't think you should make any changes, but I do think it at least provides. And by the way, email me, I'll send you his book. I've got an extra copy if you want it.

[A]

Oh yeah, yeah, coming into view.

[B]

Yeah, coming into view.

[A]

The title of the book for everyone else who we will not send an extra copy to.

[B]

Only sending one to Steve.

[A]

If he emails, just email us, we'll hook you up.

[B]

But yeah, I think that that's, that was just like an important conversation because I think it's on the minds of a lot of people. Like how is AI going to impact not just my profession potentially, but also like the, the investments that I hold as well.

[A]

Yeah, yeah. And Steve, he's in money gear seven. But that doesn't mean that you are fully financially independent or even that you want to quit working.

[C]

Right.

[A]

Doesn't sound like you have any real debt that's weighing you down. You've been doing a really good job investing as well. Right. Like you are fully funding your accounts at the beginning of the year. So you are paying attention to three.

[B]

Out of four years. He is a man after your own heart.

[A]

Oh my gosh.

[B]

In that regard, I love that you love a January 1st full fund.

[A]

Pull the trigger. Make it happen. Yeah. Being in that position is going to give you a lot of cushion and flexibility. But still, retirement isn't always something that we choose to do.

[B]

Right.

[A]

And my guess is that you could still use some of your skills in other ways if AI were to crush your small business. But that being said, you may not want to do those things and you may not have to if you've built up a large enough nest egg and it's. It's well, diversified.

[B]

Yeah.

[A]

Steve kind of points to the fact that he's kind of in this weird situation where, like, AI is bad for business, but it's good for. Good for portfolio. As he's looking at his nest egg, I kind of think he's in the perfect position. Right. Because, like, you are perfectly hedged to a certain extent because you're diversified in that way at least. Because, yeah, he's worried about the portion of his overall portfolio being intact. And if it takes off, well, guess what? You can afford to retire early, but if it doesn't and it does pop, turns out you're in business for another 10, 20 years, perhaps.

[B]

No, but I think that's what he's saying too, though, is like, actually, if the bubble bursts, I'm impacted. He thinks, yeah, maybe you're right. Maybe that keeps his business around longer.

[A]

Yeah, that's it.

[B]

But maybe it doesn't.

[A]

I think he said it as, like, a negative in that, like, well, it's just an awkward position. But actually, I sort of see that as a good thing because if it does well, well, you got a little bit of that. If it does poorly. Okay, well, you got a little bit.

[B]

Of that as well. That might be a good point, but the heart of Steve's question is about his portfolio allocation. And VT Sachs. VT Sachs and Chill can be kind of a great strategy for a lot of investors. VT Sachs, by the way, if you're listening and you're like, what is that? It is a Vanguard etf, Total Stock Market etf. And it is incredibly inexpensive. And so that is like one of the funds that's highly recommended. Matt, your equivalent. Oh, that's the mutual fund. The ETF is Voo. Right.

[A]

Well, Voo is the S&P.

[B]

Okay, so then Vti. Vti, that's right.

[A]

So Vti, total Vanguard's total stock market ETF.

[B]

So Vti is the ETF version of VT Sachs. So that simplicity is crucial. It's certainly not the right mix for everyone. Right. Your timeline, your individual investor timeline. Is crucial. The reality is that Steve might, he might need to start tapping those funds in half a decade. I lean here towards Steve's line of thinking, Matt. He's not making this knee jerk decision based on headlines. His risk profile truly is changing and he is getting closer to the wealth preservation stage of his life.

[A]

That's a kind way of saying he's getting older.

[B]

Well, that. But he's also much younger than most people who are going to be tapping their retirement fronts because it doesn't sound like he's anywhere close to traditional retirement age. He is just getting closer to saying I'm financially independent and I might not be working anymore. And because of that he's going to want to stay heavily weighted towards stocks still because he is young. But not being as tech and as US centric would de risk things for him given kind of where things stand in his personal situation.

[A]

Yeah. Not being quite as exposed. One of the other things that Steve mentioned was not selling his current holdings but, but buying those other funds with new investment dollars, which I think is a really smart way to rebalance. That's actually something that Joe mentioned in that interview, Joe Joel, when you talked with him, that it's like slowly, gently moving the rudder as opposed to jerking the wheel to one side and then.

[B]

You fishtail and crash. A lot of people want to go sell positions and buy positions and Joe's thing was like just ease into it slowly. Buy the new position and you'll rebalance over time.

[A]

Exactly. Increasing exposure every month with those new investments means that over the next few years you're going to be changing your investment mix in a meaningful way without some of those substantial changes. Now that actually could be more headline driven perhaps with it being more in the news lately.

[B]

Yeah. Steve, he's still looking at low cost Vanguard funds, which is brilliant. Of course he mentioned he's experiencing less growth by potentially making these changes. That might be true, it might not be. Recent history would say that you're stupid to opt for less tech exposure. It would be like, no, no, no. The fact that you're not invested solely in the Mag 7 means you're a moron. Right. But that could change quickly. Right. And it's really hard to know when or how or if that's actually going to come to pass. And so your goal at this point in your money progress in your journey isn't to maximize returns as much as possible, it's to be prepared for upcoming changes. Matt, you mentioned the term hedging. It's to be hedged to make sure that you're not exposed on the underside. You have this soft underbelly because you didn't take into account changes in investor sentiment that could negatively impact you if you were all in on one, on one fund. And so know what you're after, make changes for that reason. It's going to help ensure that you don't kick yourself for missing out on higher returns if that's what comes to pass. Because you might be like, dang it, I did the wrong thing. And no, just because you didn't get higher returns doesn't mean you did the wrong thing. You could have still easily done the right thing for yourself, for your own risk tolerance, given what's happening in your life and the potential loss of your business.

[A]

Yeah, the risk tolerance part of it is super important, and this is why this is such a personal decision. One of the other things Joe Davis talked about in that interview, Joel, that you had with him, we'll make sure to link to that one in the show notes for this episode. But he talked about that thought exercise of imagining your portfolio down 30%.

[B]

So good.

[A]

Which I've never done that. And so I actually, as I was.

[B]

Sitting there editing a Cold sweat.

[A]

No, but as I was listening, as I was editing that episode, I hopped on over to my Excel, pulled up all my investments, and I did a times 1.3 and did a 30% up. And so you were like, that was the fun side of things.

[B]

What if 20 million became 14 million?

[A]

Oh, that's the 30% drop. But he said to do both, which was an enlightening exercise, because I was like, oh, wow, holy cow. If the market does go up 30% over the next couple years, it would be shocking to see what that would grow to. In a similar way. That was the fun side of it. The not so fun, the more painful exercise that is also probably more important is to see that drop and to kind of feel that to see that number within your framework, in my case, over there on Excel, and to think, okay, yeah, this is the price of admission. It could. This could very easily happen. Do I have what it takes to see this thing out were that to happen over the next couple years? So I think in a similar way, whatever it takes for you to kind of visualize yourself in that position, Steve, is what I would recommend that would help you.

[B]

Then if it does come to pass, you're like, I already went through. I've been here before. Exactly. Yeah.

[A]

Folks talk about visualizing victory, right? Like, literally go through the steps, creating new habits. Right. Like a lot of times talk about, okay, imagine waking up the next morning. Imagine putting your shoes on, going for the run. Not to make this all about you and running, Joel, but imagine being handed the trophy or the medal after, after running your marathon.

[B]

They do hand out obscene medals sometimes. I hate those medals. I do.

[A]

But I think doing some of these thought exercises could be really beneficial.

[B]

But not just the victory one, the defeat one, too. What happens? Oh, yeah, yeah. If, like, there's market decline, that's the more important one.

[A]

Hopefully the fun, positive one is just for kicks and to think, oh, wow, but don't count on that. Right? Like, that is the if things like you can't count on the best case scenario, unfolding something else as you are potentially getting closer to retirement, stocking up on cash, having more cash in your savings account so that it gives you a bit more flexibility were you to enter into those retirement years a little bit sooner without having to draw down on your retirement nest egg in a down market where you'd be hit with that sequence of returns.

[B]

Risk maybe diversifying with those new investment dollars, stocking up on cash over the next five years in anticipation of this potential happening of becoming obsolete, essentially your small business. And that, I think, will give you enough diversification from a cash and stocks perspective to weather a storm and feel like you're doing it in the right way. You got plenty of time to play in here. That's right. All right, we got more to get to Matt, including a retirement account. I don't know if we've ever discussed it, if we ever talked about it on the show before. We'll get to that question and another one right after this.

[A]

Having worked as a professional photographer, I might be a touch biased, Joel, but I love that I can relive my favorite memories and holiday traditions. And with an aura frame, I can do that every day. My favorite memories are just the variety of different experiences we've had over the years as a family. Like running the Thanksgiving Day half marathon, a staining rib roast at Christmas, or even the time we went to the beach on New Year's Day.

[B]

Yeah, man. Aura frames are an excellent way to keep those memories front and center. Plus, you can preload photos onto an aura frame before it ships, and you can keep adding them from anywhere, anytime. You can also share photos and videos effortlessly straight from your phone all year long. You can't wrap togetherness, but you can frame it.

[A]

And for a limited time, visit auraframes.com and get $45 off Aura's best selling Carver mat frames named number one by Wirecutter by using promo code howtomoney at checkout. That's a U R A frames.com promo code howtomoney. This exclusive black Friday Cyber Monday deal is their best of the year, so order now before it ends. Support the show by mentioning us at checkout. Terms and conditions apply. This message is sponsored by Navy Federal Credit Union. As the holiday season rolls around, Navy Federal knows that you strive to do everything you can to bring cheer and joy to your loved ones. And as a credit union dedicated to serving all veterans, active duty and their families, they understand that every little bit counts.

[B]

That's why for a limited time, you could earn a $250 cash bonus when you spend 25 dol $500 with Navy Federal's cash rewards and cash rewards plus cards in the first 90 days. But the giving doesn't stop there. You could also earn up to 2% unlimited cash back with these cards. So saving up for whatever the season brings just got a little easier.

[A]

Givejoy. Get joy. Join now@navy federal.org @navy federal Credit Union. The members are the mission. Navy Federal is insured by NCUA. Visit Navy federal.org cashrewards for details. Cash back terms and conditions apply. Offer ends January 1, 2026. Hey y', all, it's Joel and Matt from how to Money. Joel, you were just out in Seattle recently, weren't you?

[B]

Yeah, man, it was amazing. I went for one of the most glorious runs of my life along the waterfront. It had everything you could ask for. Crisp air, mountain views, fairies gliding across the water. Beautiful.

[A]

I love it, man. Yeah, for us, our road trip through.

[B]

Charlottesville was a highlight.

[A]

We actually splurged on a custom built Airbnb and it was well worth it. The house had these unique touches. Poured concrete counter there in the kitchen with a built in drying rack. Super functional. It even inspired some ideas for our house.

[B]

Oh. Plus, with a kitchen like that, you save money eating out.

[A]

Yes, exactly. That's what struck me. What seems normal to a homeowner. It can be the thing that makes a guest trip really special.

[B]

Which is why hosting makes sense, right? Travelers are looking for those authentic, memorable spaces. And if you don't have time to manage all that well, Airbnb's co host feature makes it easy. A local co host can help with everything from creating the listing to keeping your place running smooth.

[A]

Yeah. So while you are off making your travel memories, your home could be helping someone else make theirs. Find a co [e-mail] host alright, buddy. We are back from the break. Let's now hear from a listener who is considering hopping banks. Hey, Matt and Joel. Joel and Matt. Mole Jack. You guys are awesome. My name is Jordan, longtime listener really since you guys debuted in 2018 and I just have a question. I have a high yield savings account with Ally and the rate has shifted down from the fours into the threes. And I was just wondering, you know, what your thoughts are on moving large amounts of money into other high yield savings accounts offering better rates. You know, you can play the credit card rewards game. Do we play the high yield savings account rewards game in terms of interest and things like that? How does that work? What are you guys thoughts on that? All right, thanks Matt.

[B]

What you think about our celebrity nickname?

[A]

Which one do you prefer?

[B]

Mole or Jat Snow? Brangelina.

[A]

That's all I can think of. Tomcat was Tom Cruise.

[B]

And why do ours have to be so bad?

[A]

Katie Holmes. I don't know.

[B]

I'm okay with it.

[A]

Ours could be way cooler.

[B]

We'll just let it die now. Just call us the boys as people do. Well, let's. Jordan's question. Ally as one of the best online banks, you've been with Ally for a really, really long time. Well, how long do you know?

[A]

10Th decade. Oh, I might be closer to 20 years, dude. I mean it feels like it's been forever. It feels like I've always been with Ally.

[B]

I'm like at the age where I underestimate how long things have been. I'm like, wait, that was 20 years ago.

[A]

Now we're measuring things by decades again.

[B]

I'm old. But Ally has great customer service, as you know, Matt. They got a great interface, extra perks. I like the way they do savings buckets. They've got no penalty CDs, which we think is cool. They've got competitive interest rates in the market. Why would you consider leaving a bank like that, Jordan? Just to get a slightly better rate on savings? I don't know. I probably wouldn't make this move. I think the exception would be if you were doing something known as soft switching, which Matt, you and I talked recently on a Friday flight. Like if you're funneling a bulk of your savings into an account that's paying more, let's say with like Betterment or cit, who are paying some top notch rates right now while you're still keeping Ally kind of at the center of your personal banking orbit. I think it, I think it can make sense. But if you play the sign up for better Rates game on repeat. And you're moving everything over and trying to do everything under a new bank that you, you know, switching your bill pay, all that kind of stuff. Boy, that sounds exhausting after a while, doesn't it, Matt? Sure.

[A]

It depends on the stage of life that Jordan is in. He sounds like he's got a bit more energy though.

[B]

Right.

[A]

And so typically when you're younger, you've got more time on your hands and maybe less money and so your no stone goes unturned when it comes to optimizing. And Max, I don't know, I'm just throwing that out there.

[B]

I still remember sign up bonuses for. I would win every single one.

[A]

Every single one.

[B]

Yeah, I opened one up at Chase and I had to go into a physical branch to do it. And I think it was like 300 bucks.

[A]

You're like, what is this, 2010?

[B]

I know it was probably. And there were all these hoops to jump through. And I remember at the end of the day being like that $300 was not worth the effort.

[A]

Well, that's. Honestly, I think that's a good lesson to learn, Jordan, like, if this sounds appealing to you, give it a shot. Because this isn't like a irreversible decision. Like, give it a shot.

[B]

See how it feels.

[A]

See if you think it's worth it. Especially if you're talking about the soft switching, like you're talking about Joel, where you're putting a portion of your money, like the portion of your emergency fund that you know you're not going to touch. Let's say you've got a solid six plus months worth of living expenses. Okay.

[B]

Yeah.

[A]

Move that over there and then you can just learn and say, huh, was that worth it? And if not, you can just undo it. Right. Like this is one of those two way doors where it's easy to walk back and no harm, no foul.

[B]

If it's the soft switching, then where you have both bank accounts are kept alive and they're connected, you could transfer money back and forth within a couple of days. And so I have multiple bank accounts. If you're doing that and you're like, this is the place where I keep the bulk of my savings and this is the place where I operate my day to day. Great. Why not have a relationship with two banks? But really, when it comes down to it, if you're talking about switching all the way and abandoning Ally, opening up this new bank account because they're paying half a percent more, and let's say you've got $20,000 in savings. Well, how much is that actually going to move the needle? I would want to know that before I moved all the way over. And so, yeah, this sort of soft switching two bank thing makes more sense to me than going all the way in and ditching your current bank for a new one that pays a slightly higher rate. But yeah, I guess if you have a ton of cash on hand, Matt, the benefit is more substantial. But even still play the both bank game.

[A]

Totally. All right. The Facebook question of the week comes from Angela, and she wrote, I frequently hear the guys extol the great benefits of an hsa. Up till now, I have always had my employer's HRA plan with open enrollment. I was wondering the pros and the cons of the two. Also kind of curious why I never hear Matt and Joel reference an HRA in general. I'm a newer listener, so I apologize if I have simply missed this discussion. You have not missed the discussion, Angela.

[B]

She also not something we've talked about. What she did miss is that we go by Mole or Jack now. So, Angela, let's get that right.

[A]

Or the boys. The fellas. Yeah. No, I will say, Angela, thank you so much for being a new listener. And the hra. Why don't we mention it? Well, it's because it's a much rarer perk than the other main retirement accounts that get discussed frequently. IRAs, they are fairly ubiquitous. Same thing with 401s with HSAs as well. But HRAs are far less common. And so for those who don't know, it is a health reimbursement arrangement. Thus, again, the casual nature of the arrangement. This is something that we've talked about, but it's a real thing. Again, but some companies offer this as a way to help employees fund healthcare expenses. And it's something that your bot, like your company, they fully fund.

[B]

They fully.

[A]

They contribute to. It's not something that you can do.

[B]

You don't need to do anything.

[A]

Yeah, yeah.

[B]

It's just a benefit. You have to use the money.

[A]

Yeah, that's true.

[B]

Yeah.

[A]

And you just submit your receipts, your expenses, to be reimbursed from this account. And it's pretty nice if this is something that you have at your disposal.

[B]

Yeah, yeah, exactly. But you're right. I mean, like, the reason we don't talk about it is just because so few people have access to one. And I'm glad you're bringing it up, because for people that do, especially this time of year, just recognize that. Yeah. Your employer might offer you free money for healthcare expenses you might incur and you might have to do less saving on your. Or it might even mean that you can contribute more to an HSA for future healthcare costs. But we'll get into that too here. You might not be to.

[C]

Able.

[B]

Able to do both. So there's really not much for you to do except use the funds in the HRA that your employer provides if you have them, because your employer owns those funds. And if you don't use them in a given year or if you leave the company, you lose access to those funds. So maybe you schedule an elective surgery or something because you realize you're not going to fully utilize your HRA dollars if not, or you bump up a medical procedure into the current year to fully exhaust those funds when you might have waited another year. Those are just kind of thoughts on how you might utilize the HRA to its full potential. But kind of. You kind of hinted at the question, Angela, can you use an HSA and an HRA at the same time? Potentially. You know, you can't have the traditional HRA we were just talking about, but there are other versions of the hra. So this is not, this does not come out without its complications. If you have a limited purpose hra, you can use an HSA at the same time. And if that's the case, we would say use them both. But if you have access to one of these, the full HRA version and not the kind of light limited version, then you cannot simultaneously have both. So which one's better probably depends on how much your employer contributes to the hra. But if you have a really generous employer offering a substantial reimbursement for you every year, that's a pretty sweet perk that I'd want to take full advantage of.

[A]

Certainly something to keep in mind, like if, especially if you're weighing another job, like, this is a sweet perk, this is a sweet benefit that you have and make sure to count that into the total compensation package that you're being offered.

[B]

I mean, it can be five grand in free money towards healthcare. And you're like, well, I get paid 70 grand a year. I want to go get take this job that pays 75. Not really.

[A]

You get paid 75 plus.

[B]

Exactly.

[A]

Mentioned the match. And, and I'm not saying you should stay there at whatever company you're at, Angela, but something to consider.

[B]

And those dollars don't get taxed either. Sweet. From by the, the government doesn't tax them for the employer. You don't get taxed for Using them. So they're tax tax free money towards healthcare expenses. All right, Matt, let's get back to the beer. This one that we enjoyed on this episode was a vintage ale, a bourbon barrel aged Imperial stout by. It was Kirkland Signature, but brewed by Deschutes Brewery out of Oregon, who seems like they teamed up and they're making a lot of beers for Costco's private label.

[C]

Now.

[A]

Is that where Costco. Where's Costco based?

[B]

Washington. Kirkland, Washington. So it's like, right there. Yeah. They're not too far, I guess, bordering.

[A]

Is that why it's called Kirkland Sig because it's based out of the same town?

[B]

Kirkland, Washington. Oh, very cool.

[A]

Yeah, I didn't know that. You probably bet you learned that during that episode of Acquire.

[B]

Probably. I'm sure I did, but I have a.

[A]

Wait, is it called Acquired or Acquired? Yeah, I'm thinking of the board games.

[B]

I mean, that's still one of the best episodes of Acquired. The Costco one.

[A]

Yeah.

[B]

But one of my family members actually got to tour the. And I was like, dude, last time I was in Seattle, he was telling me about his tour of the headquarters. Headquarters of Costco. And I guess it's pretty Spartan, so it's. Which you would expect. You would expect that from Costco.

[A]

It kind of feels like that aisle, like that hallway on the way to the bathroom at Costco. That's just kind of like.

[B]

That's exactly right.

[A]

Does anybody ever walk over here?

[B]

Right. And you see the employee break room over there off to your left? Yeah.

[A]

Just looks like an extension of the warehouse.

[B]

I know. So I'm a little jealous, though. And I don't know, hopefully.

[C]

That's funny.

[B]

Someday he can give me the hookup and I can check out Costco HQ as well. But thoughts on this beer?

[A]

It was really good, man. That bourbon barrel, I mean, that's the first thing. Like, we poured it and I gave it a little sniff. You could totally pick up on that on the nose. But it wasn't overly boozy. It was just nice and oaky, which is hard for me to not be happy with a beer that doesn't have a strong oak presence. Yeah, that's like one of my favorite flavor profiles in any. Almost any beer. Like, I love it in a stout, and I really like it in sours as well.

[B]

So I'd say it's hard for you not to be happy in general, my friend.

[A]

Oh, yeah?

[B]

Yeah.

[A]

Am I a fairly positive guy?

[B]

I think so.

[A]

Okay. Yeah, I can be moody Sometimes you've seen me be moody before. What'd you think about it, though?

[B]

Dude, I loved this beer. And to be honest, like I said, I have not enjoyed many of the Kirkland signature beers in the past. This beer was excellent. Like, it was truly fantastic. Although I would maybe quibble with the definition of this as an imperial stout. It.

[A]

It wasn't.

[B]

Yeah.

[A]

Wasn't stout territory.

[B]

Was it Scotch ale or quad kind of vibes going on. Some of those dark fruit vibes, maybe like fig and raisin notes. But this is so high quality and it had kind of some of those unique holiday spices going on. Almost like the St. Bernard is Christmas ale.

[A]

Yeah. Which is one of my gonna say.

[B]

That favorite beers to drink this time of year.

[A]

And I was like, totally getting you in the mood for Thanksgiving coming up later this week.

[B]

100%, man. I was like, this is the perfect beer to drink this, this time of year. So if you totally agree, can find the vintage ale at your local Costco. Buy it. Maybe buy a couple.

[A]

Have we ever gotten it in the past? Have we picked it up? I want to say we have.

[B]

Maybe. I'm trying to think. They used to carry Cheme Blue.

[A]

Oh, that's what I'm thinking of.

[B]

And that's what I would get at Costco menu.

[C]

Yep, yep, yep.

[B]

Because that similar kind of, you know, fall partnership. I wonder if this is the first.

[A]

Year that they've done this partnership with Deschutes. But I think it, like, it's labeled a stout, but it is not super thick and stouty. Like it is lighter in body, which honestly, this time of year I'm looking for a little bit like, I want that darker flavor and those notes, those spicy notes, but without, you know, you don't want to get completely filled up as people are passing around pumpkin and pecan pie.

[C]

Sure.

[B]

So to me, this was.

[A]

This is perfect.

[B]

Better than I thought it would be and well worth buying.

[A]

Pleasantly surprised. I will actually, next time I go to Costco, I'm gonna look for this and pick up a couple bottles for the holiday season.

[B]

The value excellent too.

[A]

Nice.

[B]

So all right, that's going to do it for this one. We appreciate you listening. You can find links to some of the resources we mentioned up on our [e-mail] there's also literally a resources page on our site. So if you're like, I heard the boys mention something or I've heard them mention that a couple of times. It probably lives on the resource page.

[A]

I heard you redact the boys.

[B]

The boys Matt or no? What JAT and mole. So yeah, you can check that out. There's plenty of stuff, good stuff up there on our website at how to Munch.

[A]

That's right, buddy. But that is going to do it for this episode. So until next time, best friends out. Best friends out.

[B]

Honestly, Honestly, Honestly, no one wants to think about hiv, but there are things that everyone can do to help prevent it. Things like prep. PREP stands for Pre Exposure Prophylaxis, and it means routinely taking prescription medicine before.

[A]

You'Re exposed to HIV to help reduce.

[B]

Your chances of getting it. Prep can be about 99% effective when taken as prescribed. It doesn't protect against other STIs, though, so be sure to use condoms and other healthy sex practices. Ask a healthcare provider about all your prevention Options and visit findoutaboutprep.com to learn more. Sponsored by Gilead.

[A]

Okay, only 10 more presents to wrap. You're almost at the finish line, but first.

[B]

There the last one.

[A]

Enjoy a Coca Cola for a pause that refreshes. Hey, it's Ryan Seacrest for Albertsons N Safeway. Flu season is here and our pharmacies have you covered with a free flu.

[B]

Shot with most most insurance plans. Plus it's cough and cold season and now through December 2nd. Stock up on all the season's essentials and get ready for relief with discounts on items like Mucinex Cold and Flu Kickstart, Mucinex, Fast Max Products, Vicks Dayquil and nyquil Combo Pack. Alka Seltzer plus also Airborne and afrin offers end December 2nd. Restrictions apply and offers may vary by location. Visit Albertsons or Safeway.com for more details.

[A]

This is an iHeart podcast.