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Matt
This is an iHeart podcast. Guaranteed Human. Every small business owner has that one moment that could have broken them. But remarkably, it didn't. Hi, I'm Ben Walter, CEO of Chase for Business and on season three of the Unshakeables, my co host Kathleen Griffith and I are bringing you more incredible stories of overcoming the impossible. We're really proud to share that the Unshakeables is nominated for Best Branded podcast at the 2026 iHeart PodC podcast Awards. Listen to the Unshakeables wherever you get your podcasts and learn more@chase.com podcast JPMorgan Chase Bank NA member FDIC copyright 20 and 26 JP Morgan Chase Co. Indeed sponsored jobs get you quality candidates when you need them most. Spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results when you need the right person to cut through the chaos. This is a job for indeed.
Joel
Sponsored Check and listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves. Indeed.com podcast terms and conditions apply. Need to hire. This is a job for Indeed.
Matt
Sponsored Jobs Struggling to see up close make it visible with viz. VIZ is a once daily prescription eye drop to treat blurry near vision for up to 10 hours. The most common side effects that may be experienced while using VIZ include eye irritation, temporary dim or dark vision, headaches, and eye red. Talk to an eye doctor to learn if VIZ is right for you.
Joel
Learn more@viz.com welcome to how to Money. I'm Joel.
Matt
I am Matt.
Joel
Today we're talking AI money impacts side hustle, salad days and sill and SA.
Matt
You know what buddy, this is our Friday flight and we're going to get to the top. Headlines from this past week, how they impact you as an individual. And you've got something here about Rivian which I know you're not actually interested in purchasing because you're very happy with your forerunner.
Joel
Not anymore. I think I I mentioned which they
Matt
they actually look similar. You know, like the general body shape. I saw Rivian pass me this morning and it's got like a smaller back like the little hatch, little little tailgate which is pretty. I don't know in my mind that's reminiscent of. I guess maybe it's some of the like the older forerunners not unlike yours.
Joel
Well the other the thing about four Runners is like the style has barely changed over the past like 30 years. So you're like what? When people see my forerunner, they're like, that looks like it's like five years old. I'm like, yeah, it's 20. But it. Just because the body style has so little.
Matt
Yeah, it's the 2006.
Joel
Yeah.
Matt
That's crazy.
Joel
I know. That's crazy. I know. It's in great shape, which is. Well, it's also just nice when the body style changes so little. And so it's really hard to put a finger on exactly when it was made.
Matt
But no, folks see my 06 Odyssey and they're like, is that a new. No, I don't have an Odyssey. Got a 2012 Odyssey.
Joel
But still, those have changed a little more. But although the body style on those hasn't changed significantly.
Matt
Not a ton. But you go back, I don't even know if they existed back in 06, but I guarantee you the Toyota Sienna's
Joel
Honda Odyssey, we had an 06 Odyssey.
Matt
I'm just saying. I guarantee that they did not look like the new ones today. The new ones today look significantly different.
Joel
My 06 Odyssey was like powder blue and had a very different body style
Matt
than that was an 06 as well.
Joel
That was an 06 too. Nice. Yeah, yeah. And it was a great ride.
Matt
What's crazy is seeing, I guess like the late 90s Sienna's or Odysseys, like, you don't see too many of them on the road now because, I mean, let's face it there, that's just really, really old. And they're so small. That's what blows my mind, seeing them. Oh, yes, it is crazy how just how much bigger they've gotten over time.
Joel
I remember my friend's mom had like a Ford minivan and I. I remember what they looked like, but I don't
Matt
remember if they were like the wedge. It's like straight from the road and it. Yeah, it's a straight line from the front bumper to the hood to the windshield.
Joel
The wind star, aerosol star or something.
Matt
Yeah, exactly. So funny.
Joel
Mini pin talk right off the gate.
Matt
So we gotta stop it with the
Joel
dad talk here, old man. So Rivian, I'm no longer interested. Oh yeah, Rivian, the R2 still like. Oh, yeah, I'm excited about it. It's coming down the pike. I think it's about to start hitting stores. I think people can now pre orders have been open for a long time, but I think people can actually buy them shortly. And I think it's awesome. Like the idea of a moderately priced electric suv, that's pretty cool. Is exciting to me. But something you got to take in mind and we talked about the total cost of ownership, how important that is when you're buying a car. Last week, because gas prices. Right. Still a big topic of conversation. But often we over index for gas
Matt
prices and maybe less so after 400 million barrels of oil were released.
Joel
We'll see how. How much that impacts prices at the pump.
Matt
That'll get us to April.
Joel
But okay, so if you are driving a Rivian right now, you're probably like haha Al Fox to everybody. I'm saving on, on gas and gas. The higher gas prices go, the better you feel as an electric. Electric car driver. But they're also incredibly expensive to repair. And so listener Adam sent over. Oh yeah, the video. Did you watch that?
Matt
Yeah, well, I kind of skimmed it,
Joel
how expensive skimmed it is to repair. And this is something we've talked about too. When a battery gets damaged or something like that on a Tesla or an electric car, it can. This is why it can dramatically increase the cost of repair, which is why insurance costs so much more. So for so many electric vehicles, that video was like enlightening.
Matt
It had something. Yeah, it was like something like $40,000. And it was just this one panel that was dented, but it had something to do with the fact that they were all connected or something like they had to replace so much of the vehicle and take it apart. And then in the. The real hero that video was. It's. It's got what, it's an acronym. It's like dentless or no, paintless dent repair or something like that. That's like the real takeaway is just like, what is this magic that they're doing in these body shops where it's paintless? So they literally are just undenting a dent, which I'm like, how.
Joel
How's.
Matt
How do they do that even possible? Something I need to consider, I guess, if and when we dent our. Our van. But because they showed the before, the after, and I'm like, oh, it looks really good. But then how does it not. How does the paint not flake off? I don't know at some point because like if there's a dentist. The bond between the paint and the metal, this is where my mind goes. It goes to like the.
Joel
The chemistry of it all.
Matt
Mechanical sort of aspects of how like there's no way this is gonna last over the course of years. Cause I could just see that section where they undented it. That paint kind of flaking off or something.
Joel
At some point I could too.
Matt
But yeah, newer vehicles, I think what you're getting at as well, though, is the fact that especially for something brand new like that, there aren't. I don't know, there's just less normal parts. It's not a streamlined procedure as to how it is that you can repair some of these vehicles as opp. Something that's been around for. Not just a manufacturer that's been around for decades and hundreds of years, but even certain body styles, like your. Like the Forerunner.
Joel
Right.
Matt
Like it's standard parts. Like it is not some sort of special order that needs to take place when it comes to making a repair on that thing. It's.
Joel
Yeah. I gotta put a new standard issue blower motor in our Odyssey because the heating and cooling is like, it's intermittent on. So like, we'll turn it on and it just won't come on. And then it'll come on later. And I think it's a motor issue. And I'm like. I'm not worried about that. It's not gonna. I know it's not gonna be. It's not gonna be super cheap, but
Matt
it's not gonna be the special order
Joel
part, nearly as expensive as it might be on a fancier, newer ride. So this is just another one downside.
Matt
If you're part of the cutting edge. If you're an early adopter, man.
Joel
I think there's just so many more reasons to kind of drive somewhat older vehicles at least. Because part of that's just repair costs
Matt
and the tried and true, the tested.
Joel
Yep.
Matt
All right, let's keep moving. Let's talk about. Let's shift gears. Talk about credit cards, man. Cause there is another premium credit card that just dropped. We've talked. Some of these cards are costing basically like 700 bucks. The Amex Platinum.
Joel
895 maybe.
Matt
Is it 900?
Joel
I think so.
Matt
Oh, my gosh.
Joel
Yeah. So this is.
Matt
That makes this one not cheap by comparison sound as bad. I'm talking about the Robin Hood Platinum card. It's got an annual fee of $695. And here's one reason where it might be great. The fact that you get 10% back, 10% cash back, not only on hotels, but on car rentals. And they are going. And I think you're gonna push back and you're gonna be like, nobody should
Joel
have the stupid card. Not nobody, but if you're someone who uses hotels and cars, if you're traveling all the time.
Matt
Yeah.
Joel
So that's a huge perk.
Matt
Absolutely. Absolutely. And so, like, you see the big price tag and there can be an immediate pushback of like that is so ridiculous. But I quickly ran some just back of a napkin kind of math and if you like I don't travel for work. You know, we just sit here, I walk. Me traveling to work is like, oh, I walked to the office today instead of riding my bike.
Joel
Yeah, that's shaking things up for you.
Matt
Yeah. But for some folks, I mean like, you know folks who travel like not multiple times a month, but even weekly. And for those types of folks and I again, so I quickly did the math. It would take one trip a month where you're spending two nights in a hotel plus a car rental. That would be more than enough to earn back that annual fee of $695. And then after that you're just making bank. So I don't know, when you see a car that has a cash back on a certain category like that, that's something to pay attention to. Like that is where it's sort of like the.
Joel
Because on top of that, if you're traveling like that, you probably take flights and you probably eat out more. Other aspects, 5% cash back on both of those categories. So if you are one of those people who this card is targeting, I think it can make a whole lot of, a whole lot of sense and you might balk at that initial price tag. But when you look at those numbers, I actually in some ways I like how straightfor part of the card is right the 10% on this and 5% on this and you're like okay, that's pretty good. That's a solid rate of return on
Matt
and it's fairly transparent. And I'll try to do some of the math and figure out whether or not this is a game that you want to play because that's what it ultimately comes down to. Because even like we always talk about, we'll often mention the Amex Blue Blue Cash preferred.
Joel
Preferred.
Matt
Yeah. My mind immediately went to the platinum,
Joel
the $95 annual fee on the yeah.
Matt
And again you got to run the numbers and is that a game that you want to play? And for a lot of folks, just because it's universal expense, it's kind of a no brainer if you have the
Joel
same back on Groceries is like it's pretty great. It's like it's better than any other card that exists.
Matt
Exactly.
Joel
And we all, we, we even get groceries.
Matt
But even still is that a game you want to play for the. In, in this case it seems like a low hurdle when it comes to groceries. But for other folks who are traveling a lot to them, that's a low hurdle. Like, that's an easy bar for them to, to be able to achieve.
Joel
I guess I get annoyed at. And we've talked about this kind of the coupon book is Asian of credit cards and the way they slice and dice some of these rewards. And so in the marketing, it's like, hey, you get 250 bucks worth of free doordash. And it's like, oh man, that's like, you know, over a third of the annual fee. That's, that's great. Like, if I can get 250 bucks worth of free doordash, I'll sign up for that. But of course, in the fine print, the credit comes in $10 increments on orders of $50 or more. So you're like, okay, if I order doordash now I'm just going to be ordering doordash even more.
Matt
Now you're making me order doordash in order to get my. Right, get my money's worth.
Joel
And I'm just going to be wasting more money buying food that gets delivered to me, which is not terribly helpful. I do think that the other Robinhood card that exists, the one that you got, the 3% cash back is across
Matt
the board, is one that makes sense
Joel
for a whole lot more people. Yeah, this one is probably going to be highly selective for like heavy, heavy travelers.
Matt
The heavy travelers for sure. Let's talk about AI Joel, because it might make mortgage underwriting a whole lot quicker.
Joel
Right.
Matt
So instead of this being like a three week process, a new partnership between Better and OpenAI, they are promising to dramatically reduce the time to less than 1 minute, 60 seconds or less. Gone in 60 seconds is your money and your ability. Well, I guess you're trying to buy
Joel
the house, but do people know about that movie anymore?
Matt
You know, I don't think so. That was like late 90s, wasn't it?
Joel
It was good.
Matt
1999 dropped, but I don't think it
Joel
stood the test of time.
Matt
Well, what's funny is it was a remake even then. Did you know that like there was like a six 1960s version of the movie?
Joel
Some.
Matt
Maybe in 2030 there'll be another version that's released that our kids will know about. I'm sure there will be, but so I mentioned that the fact that you can get underwritten in less than a minute, that's actually not an edge case. The average case would take something like two minutes, which is also significantly less time than three weeks. So we'll see if this actually works. It Might not do a great job, I'm thinking with some of the less straightforward applicants. I'm thinking about myself here. Not very, just I'll say I'm an atypical borrower.
Joel
At least historically people have called you atypical, Matt.
Matt
And I mean you just think about underwriting. It's a high stakes decision. So I think it'll be interesting to follow because as AI helps lenders reduce the friction of home lending, it'll get not just faster, it's going to get more affordable. The high cost of buying a home, that's been something that we've been hoping that technology would help to solve for quite a while here and better. They're on the cutting edge here with open AI, so we'll see if them combining forces, we'll see if competition, if this ends up leading to real benefits for consumers out there who are looking to purchase a home.
Joel
Yeah, I agree. I mean it's. If I was better, I would want to test this out thoroughly and I would, I would want to have like real human beings like vetting every single instance for every approval that automatically is getting under quite some time to see what the error rate might be.
Matt
For one year everybody's employed the robots and the people. Exactly.
Joel
But AI still has issues. Of course there's promise in something like this, but then there are significant risks or there are, I guess just ways that AI is still fairly ineffective. And so the New York Times profiled the risks of using AI to help you out with your taxes. Their pithy takeaway. And I think this is quite accurate. They said the world's smartest technology is no match for the US tax code. I mean, the smartest people in the world, we do have a very complicated tax code. You can't contain the multitudes of the US tax code in your brain. So there's just even people we know who are great at taxes, Matt, they really know what they're talking about. There's still a lot of information they can't fully process. AI is getting better fast, but this is no surprise, right? The New York Times found that miscalculations abounded when using any of the major AI chatbots, often leading people to over or underpay their taxes not by just a little bit, but by thousands of dollars. I think the average, it was off by an average of like 2000 bucks when they ran a bunch of scenarios. So yeah, you can get like a good idea of a particular tax law via an AI search. These days, if you're like, tell me more about the Earned income tax credit. Right. Like the. The AI can spit out. I think a decent, a decent diatribe for you, but AI is still weak in the area of complex information gathering and putting together all the pieces if you put in all your information. And of course, the US Tax code is just insanely complex and AI remains at least a little confused by it. Maybe not forever, maybe not even for long, but at least for now, I
Matt
do think that improvements will be on the way. Right. Just like the errors that you're seeing with the sites that are being vibe coded as far as. Oh yeah, these sites are down more. There are bugs that are arising and they're having to.
Joel
Wasn't that what happened with Amazon? Amazon had. Their main site was down. AWS was down for a little bit
Matt
because of what to do with that. So will it improve over time? I do think so, but I don't think we're there yet when it comes to tax law. Some of the different particulars that are working their way through the system. Actually think about the no tax on overtime, right? Like that was part of President Trump's campaign and it was of course instituted into law. But the devil is in the details, man. The fine print is quite extensive when it comes to all the ins and outs there as far as what qualifies as overtime, because the messaging definitely made it sound like anytime anybody out there work more than 40 hours a week tax free, go ahead and just stick that money right in your pocket.
Joel
Right?
Matt
But not all overtime pay is exempt from federal taxation. Much of the pay that qualifies is still subject to state and payroll taxes. It's still confusing some tax professionals out there, as well as individuals who are filing their taxes. So, yeah, it's no wonder that AI is also having a difficult time sort of parsing the details and how this is playing out in real life.
Joel
I was talking to a buddy this week and he works a job where he does get a lot of overtime and he gets paid in the traditional time and a half fashion. And that's, I think, the hoop that you need to jump through in order to be able to get that portion of your pay exempt from federal taxation. And so he's going to be sitting on like a pretty sweet gold mine of not paying federal income tax on all that overtime pay. But yeah, it has to. You got to know the details. And the details are same with the no tax on tips. Like, you have to know what the details are because not all tips count as tips. And what's your overall AGI, because you still might not qualify for no tax on tips if you're making too much. Since we're talking AI, Matt, some workers are finding that the infusion of AI into their jobs is causing their workload to pile up. Like they're kind of feeling burned out. They're being told that they need to be more productive. And, hey, this AI tool is supposed to help you out with that, so do more, be better. It is making them more productive, but it's also leading to a lot of. A lot of frustration. And I think it's one of the things that's leading people to start their own business in greater numbers, whether it's a side hustle that's easier to launch, because AI can then help you vibe code that website like you're talking about, for a physical business. Right.
Matt
While the site still remains up before it crashes.
Joel
Before it crashes.
Matt
But then you can.
Joel
And then you can use AI to fix it.
Matt
Yeah. Then dig your way out.
Joel
That's right. So. And we had friends who have, like, built websites from scratch via AI tools. And I haven't messed with it, but it's. Man, the website looks really good. It looks. It looks super usable for being something that. And I talked to someone else who said a website I made that took. Took me years to build, I think it'd take me a couple weeks now at most, which is really impressive. So these. These tools really are helping people find a way to. To launch their own thing and to, you know, be able to use those apps to start making a profit on. On a. On a business that they're launching. AI is leading to layoffs at some firms, but simultaneously to a dramatic rise in entrepreneurship. So, you know, starting your own thing, it's. It's not for everyone. Not everyone wants to launch their own business, but for many, it might be the perfect reaction to a tight labor market and to the reality that technology is. Is making this easier than ever before. It makes me think of when we talked with John Mackey, the CEO, former CEO of Whole Foods. And one, just an interesting story. One of my favorite interviews we've done. But two, we talked about, hey, is it easier or harder to start a business now than it was when you started your business? And he was like, oh, my gosh, it's so much easier now. And then think about, this was really before AI was much of a thing or was something that every day folks were using. I think if we had him back on, he would say, yeah, it's even easier now than ever before. I think people are figuring that Out. And yeah, you can either take the, you know, be working somewhere and be forced to work turn, have an even greater output because of AI's abilities or you can say, you know, I'm going to use AI on my own to launch my own thing. It'll make that, it'll grease the wheels even more for that.
Matt
Yeah. I do wonder if that has like his response there, if that had more to do with just his life experience. And once you are in the know and figure out how things work a little bit, you feel empowered to be able to continue to do, to continue to do the thing. Right. Like for you that would be the equivalent of running. Because right now you're like, it's so easy to run. You just go out and do it. Right. But for you, prior to having done that, I think it would have seemed like a pretty tall hurdle. But. And yeah, so is it a mindset thing? But I'm sure it also does have a lot to do with the technology that exists and the fact that more people are less loyal to the specific companies are with. Right. So there's a mindset shift in what it looks like to start a business where it looks, oh, you're just a sole proprietor, you're out there doing your own thing as opposed to, you know, feeling like you have to be locked in with a specific company for your entire life.
Joel
I do think it's a lot easier to find your audience. There are more tools at your disposal to help you run your business. Like there's.
Matt
It seems like that on the surface, but at the same time. So it's easier to find your audience. But then there's just as many other folks who are also trying to launch their own thing. So the noise is just incredible.
Joel
That's true too.
Matt
Right. And so like be able to cut through.
Joel
Exactly.
Matt
So like it's again everything that we come across, every tool, AI, it's a double edged sword. So in some ways it's easier, in some ways it's harder. That's why like folks who are talking about that, taking the more of the doomerism approach towards the AI where it's just like it's going to replace everything. I'm like, well, I don't know, I don't think that's true. Because it's a tool, it is a multiplier and if you want to do good with this tool, then you have the ability to do that. It's not this inherently evil thing. It's also not this inherently righteous thing either. Right. Like it's, it's like money. It's, you know, not inherently good or bad, but. Okay, we're talking about starting your own business. I saw in that article too. I wanted to share this. That new business formation, it's the highest that has been second only to July of 2020, which is crazy. That's so mind blowing that so many folks see an opportunity right now and it's not that far from new business formation back then. And so it makes me kind of question, like, is, are things really that nuts like they were back then? Because I look back to 2020, I'm like, oh my gosh, I feel like things were so crazy. But evidently a lot of people see, at least when it comes to the business world, things do look as maybe unstable as things did. But, you know, as things looked back then, perhaps.
Joel
But yeah, and it probably sounds ridiculous to a lot of people who enjoy working for someone else. And entrepreneurship feels a little scary to be like, go start your own thing. Yeah. But I think, like, why would I. A lot of people are seeing that there is a greater ability and they're having more comfort level. Like being an entrepreneur, I think doesn't look, it doesn't have to look like starting some publicly traded company. It can be a business that you run from your home so much easier than ever before.
Matt
Or even like going finding some local real estate, commercial real estate, and like signing a lease and putting down a whole lot of money, like dumping a
Joel
whole lot of capital.
Matt
Yeah, there's, there's a wide range of it. And a lot, a lot of times it starts just from side hustling. So apparently 56% of Gen Z has a side hustle these days. This is according to a new Harris poll. And I think side hustles, right? So like some people, like you're saying, Joel, they love their job, but other people are like, little unsure. And for those folks, I think it can make sense if you're just not too keen on the future of your job. Maybe you're not sure how long you can count on that position still being there. It can certainly give you like a creative outlet, Right. Where it feels a bit more fulfilling. Plus the chance to build something more meaningful that could one day turn into an actual business. Right. Because we delineate the difference between sort of hustling a little bit on the side or gigging on the side as opposed to starting your own business. There's a difference there, but. And of course the extra income that can help you to reach your financial goals faster. But it's just so Hard to sustain a full time job in addition to a side hustle, you know, gigging on the side indefinitely. I think there are times to pursue balance and then there are also times to front load the sacrifice within reason. So for a lot of folks, I think they find a little more of that energy and the ability to pull all nighters and to expose themselves psychologically to the risk that's inherent with starting your own business when they're younger and when you've got fewer mouths to feed. Yeah. Not that you can't do that when
Joel
you've got a family, but I mean you and I started did it when we had a family, but I love that. I think most people should at some point try something at least just as a creative outlet and to see what sticks and don't put too much pressure on yourself. Don't feel like you got to work 30 hours a week to get this side hustle off the ground. That's the great thing. If you have a traditional job, you can put in as much or as little effort as you want and you can dial it back or dial it up, depending on how people are responding to the business that you've launched. I'm curious too, Matt. I just want to hear from how to money listeners. If you are currently engaged in a side hustle, what are you doing? How's it going? Email us howtomoneypodmail.com Give some folks ideas. Yeah, I just want to know and like maybe we'll talk about them in future episodes.
Matt
But yeah, it's always cool to hear what individuals are doing 100%.
Joel
And I feel like we get even just in regular listener questions. People will say stuff like, yeah, I make this and such in my normal job. I make a little bit extra money doing something on the side. And so they'll just. I love it when I hear that. It sounds like it's just something for fun to bring in some extra dollars. And that's a great way to think
Matt
about, especially something that could lead to again, a fully fledged business. Right. There's a difference between pursuing something like that and closing Waymo doors, which is truly something that some people are doing. They're getting requests to be like, oh yeah, the Waymo passenger didn't shut the door. In the door or in the Waymo, the robot can't drive because the door's ajar.
Joel
That the car can drive itself, but it can't close its own doors.
Matt
But again, that's adorable. Yeah, don't count on that because of course they're going to say, oh yeah, if you don't close the door, you're going to get docked or we're going to charge you or we're going to
Joel
reduce your positive feedback or something.
Matt
I don't know. There is a way around it. They'll figure it out.
Joel
Yep. But don't forget about the lowly side hustle. I think it doesn't make sense for everyone, but it definitely makes sense for some people at certain times. We got more to get to, including we're going to take the New York Times to task for a really dumb article about retirements and we're going to talk about kind of the headwinds facing real estate investors as well right now. We'll get to that and more right after this. Man, We've hired some great folks to work behind the scenes with us at how to Money over the years. If you're a small business, you know this the right hire can make or break things for you. Hoping the right people see your job. Posting is not the best growth strategy. So when the pressure's on and you need the right hire, this is a job for Sponsored Jobs.
Matt
That's right, Indeed Sponsored Jobs gets you quality candidates when you need them the Most. Join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. Spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results when
Joel
you need the right person to cut through the chaos. This is a job for Indeed Sponsored Jobs and listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com podcast just go to Indeed.com podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com podcast terms and conditions apply. Need to hire. This is a job for Indeed Sponsored
Matt
Jobs struggling to see up close. Make it visible with viz. VIZ is a once daily prescription eye drop to treat blurry near vision for up to 10 hours. The most common side effects that may be experienced while using VIZ include eye irritation, temporary dim or dark vision, headaches, and eye redness. Talk to an eye doctor to learn if VIZ is right for you. Learn more@viz.com I find it fascinating that in our modern world, most knowledge workers today likely spend the vast majority of their day writing emails, regardless of the industry they're in. Which drives home the point that we need to be thinking clearly and communicating confidently. And especially given the age of AI sounding rushed or generic, it's just not going to Cut it. Grammarly gives you one place to think, write and finish your work where you already write. It'll help you to sound natural and engaging.
Joel
Get your ideas down faster and move from draft to done with less friction. Use AI chat to brainstorm ideas. Outline a solid draft and then refine it with context aware suggestions that fit what you're working on. 90% of professionals say Grammarly has saved them time writing and editing their work. Simplify complex ideas so your message lands clearly and quickly. 93% of users report that Grammarly helps them get more work done in a
Matt
world of generic AI. Don't sound like everyone else. With Grammarly you never will. Download Grammarly for free@Grammarly.com that's Grammarly.com
Joel
alright
Matt
buddy, we are back for the break. It's time now for the ludicrous headline of the week. And this is from the Times. Headline reads the fantasy of a comfy retirement has always been a mirage, Joel. Didn't you know that? Give up hope all ye who enter here.
Joel
I just saw the headline. I rolled my eyes so hard, man. I don't think I ever rolled my eyes harder in my life.
Matt
Like the fact is, and I think people know what the gist of the article was, right? Like they're talking about just the dour outlook the Americans have about their ability to retire with any level of comfort at all. And it was just tough to read. She, she found one Gen Z who said he hopes that global warming or war actually takes him out because he's not going to be able to save enough to actually like live a comfortable life in retirement.
Joel
Can you imagine like having like saying that out loud to somebody?
Matt
It's just silly and it's like you're going to find people like that, right? Like that's the thing. If you are looking for someone who has that kind of outlook on life, like you are going to be able to find that person. And so to be, I don't know, to present that as a credible sort of attitude that a majority of Americans have. That's the part that to me feels like fear mongering going for the headlines. It honestly, it feels so disempowering. Which is maybe that's what rubs up against us the most. When we saw that, it was the fact that that is all we try to do is empower folks and to provide people with the tools as opposed to being like, well no one even knows what an IRA is like. What's the point in even having that as an option for folks? We don't need more education. That's not gonna be what cuts it. According to her tip. I wasn't a fan of it.
Joel
That policy changes can't help more people save for retirement. That more educational opportunities and creating personal finance courses in high schools, which is happening more and more across the country. More than half of states now offer that. That those aren't all good things. I think they are. I think in tandem. When you think about where retirement benefits that come from the government are compared to where they were 100 years ago, there's a lot more coverage. I think for the average person to be able to retire even if they haven't saved a dime and not be destitute. I just think, man, it's just really shocking to see a story like this. What was even funnier to me was the story next to it was about dog grooming and how much money people are paying to have their pets groomed. $1,000 for a dog grooming session. So people can afford to pay $1,000 for dog grooming, but they can't afford to save for their own retirement. And so it just felt like speaking out of both sides of your mouth. From the New York Times.
Matt
Well, yeah, I mean, that's what you get with a large media company. Right. Like if you got folks who are on this end of the spectrum and you got other folks who are like on the what, you know, they're the ones talking about dog grooming and how much you should be spending on your pets.
Joel
And I also don't want to sound like an idiot completely not understanding that affordability is an issue that a lot of people face. Student loans are obviously a massive problem for some people. It. It is of course, really hard to save for retirement. It takes a long time to overcome maybe some of the hurdles that are in your way that you didn't erect yourself. I get that. We also talk. It's. It's really important to us to talk to people on the show who have done it, who have overcome hurdles, who can show the way like makes you think of when we had hope from under the median. Matt Episode 1034 how much did she.
Matt
She never made more than. How much?
Joel
$40,000 a year. That's $40,000 a year. And they have like a paid off house. They've saved incredibly well for their financially retirement. Yeah. And like it's.
Matt
It is totally possible.
Joel
So the comfy. The mirage of a comfy retirement. I'm just like, come on, man, like, do better.
Matt
Yep. And I think it's important too to keep Like a proper perspective. Because if you look at the percentage of Americans who are actually so like someone would push back and say like, well dude, hope that's like a one off case. And that's also like the same when it comes to someone who's like really struggling. And I certainly feel for those folks and I think there's a certain responsibility that we should feel as individuals to look after the folks who are in our immediate, in our actual communities. But when you really zoom out and look at the percentage of Americans who are living in poverty, it is, it has significantly gone down. I mean in recent years it's gone down. But even like from like the 1950s, man, like it is, we are in such a better position. And unfortunately there's folks who are sharing their opinions and are making it sound like it's the worst it's ever been.
Joel
Well, and you and I have talked about the shrinking middle class. Why is the middle class like not as robust as it used to be? It's because we have more people, a higher percentage of Americans in the upper class. Right. So that's actually been growing. That's where more of the middle class is going is into the upper class. So there are issues in this country. Right, for sure. And our politicians are not always making it better or offering ideal solutions. But just to make it sound like there's no real individual agency to save enough to have a solid retirement over the course of a 30 plus year working career, 40 year working career. That's just absurd.
Matt
Yeah, and one of the approaches we needed to take is just a smart and simple investing approach in order for I think individuals to be able to responsibly shoulder that load as individuals. But I will say it's getting harder given what's being offered to everyday investors. BlackRock, they are saying that index funds aren't enough for, for wannabe retirees. So we're kind of connecting these two stories here. What we need is their private funds and actively managed assets inside our retirement accounts.
Joel
Thanks BlackRock.
Matt
Yeah, this is a literal quote from BlackRock's head of retirement. There needs to be an evolution away from index investing because the markets are evolving. And he says with a need for more oversight, which I don't like because for the, I mean the average investor out there, what they need are more of their dollars invested in index funds.
Joel
That couldn't be a self serving quote at all, could it Matt? Yeah, of course.
Matt
These are funds that they make more money on. Right. And so I guess I was starting to hedge a little bit because on one hand, I think the typical American who needs to be investing more, who needs to be empowered to shoulder more of that burden, they most definitely need to be investing in index funds. But like at the same time, the people who are listening to like the head of BlackRock, these aren't people who have never heard of index funds, IRAs, you know what I'm saying?
Joel
These are more sophisticated investors or they
Matt
think they're more sophisticated or they're folks who think they need a more sophisticated solution. Do they? No. But also, can they go out there and spend a little bit more on some of these funds that probably won't deliver better results? Sure, sure you can. And that might make you feel better like so there's a different product that you're gaining when you spend more of your investment dollars via expense ratios on products that make you feel a little fancier.
Joel
I think you get too sophisticated for your own Good.
Matt
Oh, absolutely. 100%.
Joel
I got the basics down now, so time for me to move on to level two investing. Level three investing.
Matt
Oh, I just got the raise. Time to let's take it to the next level.
Joel
And so we're a little behind.
Matt
How can we juice the returns?
Joel
And I'm not saying that there's no other smart way to invest aside from index fund. I think there are other smart ways to invest. But when we start to think we have that complexity, adding more and more complexity is going to provide better returns and is going to just help us maybe meet our goals much faster than otherwise than we otherwise would. If we were to stick with a super basic approach that often ends up not being the case. And we report stories on here all the time of people trying to get super sophisticated with their investments, whether it's investing in some sort of online real estate firm or alternative investments. The way that looks on the home screen of that website, man, makes it look like the best thing since sliced bread. Then a lot of people get left out in the lurch, sometimes losing a lot of the capital, if not all the capital they put into that deal or just experiencing more meager returns, higher fees than they were told on the front end. It makes me think about Robinhood just launched a private equity fund and you don't need it. We're long term investors and this is a short term example, but that fund fell 11% in the first day of trading. Matt, you think your, your post Iran War 3% drop of your index fund stinks? They're just, that was over the course of a week and a half. This is 11% in one day. There are just a lot of ways, bad ways that you could choose to invest that could create more shocks to your portfolio that we want you to avoid. And the abnormally high fees that these funds charge, guess what? The fee gets levied no matter how the fund performs. So if your fund underperforms and you're paying higher fees, then that's like, that's a double whammy.
Matt
And also, just stay away from IPOs. Generally speaking. I don't think we've addressed that specifically because I think listeners know that they're like, no, Matt, Joel, they're not going to like it me. They're not going to like me asking about an initial public offering. But Joe, we don't talk nearly as much about becoming a landlord these days either. It's not that you can't succeed, but it has just gotten a whole lot harder right now because of the state of the market. Folks who have been in the industry for years are having a hard time making deals work. Certainly folks who are just brand new to the scene.
Joel
Right.
Matt
Like all the noobs out there, they're facing significantly bigger headwinds. I think generally speaking, our previous advice is still accurate, but it's just really hard to apply it right now. And Business Insider, they highlighted some of the increasing problems that landlords are facing. We're talking about higher vacancy rates, we're seeing evictions on the rise. Just the cost of fixing and maintenance and repairs is pretty dang high. And so landlords are having to endure some real strain in order to enjoy these long term gains that, you know, hopefully you'll be able to experience like that pot of gold at the end of the rainbow at some point. But it's just a heads up, a warning to make sure that you have the know how, make sure you have the cash to be able to navigate some of these more difficult months and honestly, not beyond months, like even years that real estate can experience. Right. And so it's not, it's not for the faint of heart, I guess is what I want to say.
Joel
It makes me think if you were like taught to box Matt, and then they tied your left arm behind your back, like there's still that knowledge still comes in handy. But you're still a whole lot more likely to get smacked around in the ring if you can only use one of your hands to guard yourself. Right? To fight on the offensive. And I just think that there's not for everyone but in a lot of real estate deals that are happening right now for Individuals for bigger companies, like, because of the headwinds, it feels like going into a boxing ring with just one arm tied behind your back. So you have to be, you have to be ready for the other. But in 2000, in 2011, it was like having a third arm. Right? Like, that was like, that was like wind at your back. And I've never seen anybody with a third arm. But like, I would imagine it'd be a great boxer if you were born with an abnormal appendage.
Matt
I feel like the first guy that you fought in Mike Tyson's Punch Out.
Joel
Right, Right.
Matt
Glass Joe.
Joel
That's right. Yeah.
Matt
Those llama ones, like anybody can get past the first level.
Joel
That's right.
Matt
It's a little bit tougher the further you 100%.
Joel
Maybe one. And maybe the winds are starting to change. Right. Because on a positive note, for landlords, it looks like some cities where rents were like kind of crashing, they're starting to see prices tick up again. Moderate and tick up. So like in Austin where builders were throwing up apartments like it was their job because it is their job, but they were just like. And they were tossing up apartments like crazy.
Matt
They were in fact being paid to do that.
Joel
They were, they were. Well, rents were dropping dramatically because of overbuilding, but builders were like, oh, we don't stop building apartments because rents are going down. And now population has continued to increase in Austin. So we're finally getting to a point of where after three years of filing rents stable or slightly rising prices in the rent space looks like it's going to happen in 2026. Yeah. And this also, Matt, proves the age old economic reality that supply and demand still work. Supply and demand. Undefeated, baby. And so if you're a renter in a Sunbelt City newly built apartments, they're still offering a free month, maybe a free two months if you move. Like, there's still some deals to be had out there, but those offers are likely to get less generous as we reach kind of more equilibrium status in some of these markets.
Matt
That's right, Joel. We've got a couple follow ups here. There's two timely stories that we should mention. Let's talk about tariffs. After the ruling against Trump's illegal tariffs, tariff refunds are now on the way. So Customs and border Patrol, they say that a system will be in place in about 45 days from now. Costco, they have already said that they're going to use these refunds that they're going to receive from the government in order to lower prices for their consumers, which I love. I'm gonna totally be looking out for the things I stock up on, you know, and look for.
Joel
I love that too.
Matt
What is the limit per customer? Say I'm just grab that many.
Joel
I love that too. Did you see though that one customer is suing Costco because he wants Costco to pass on the refund, the tariff refund, directly to. Directly to all consumers. Which just sounds like a huge pain in the butt for Costco. So yeah. Bake it into lower prices.
Matt
Well, I mean, yeah, it makes me think about even just on customers on an individual level who themselves paid an expensive tariff. Right. Like if it was something that you received from another country. Because how the heck is that gonna work? It is unclear. It's a massive mess. That being said, there are people who are talking about it. So if there is a way for individuals to file for tariff refunds, if that comes along, we'll be sure to mention it. As of now, there is not anything like that. Which is why that guy was looking to sue the nearest thing he could sue, which for him I guess was Costco.
Joel
I mean stupid. Do your thing, man. Go for it. Student loan forgiveness is taxable again, not for folks who hit public service loan forgiveness, but for anyone who reaches forgiveness under income based repayment plans. And obviously it's a beautiful thing to have the rest of your student loan balancer given, but the tax bill that comes along with it, you remember it was eradicated between the years of 2021 and 2025. It was kind of a post Covid measurement, but that has now expired. So it's really important for all student loan borrowers to know that who are like start prepping, inching closer towards forgiveness. The average forgiven balance amount, I didn't know this. Is close to $60,000, which means your tax bill could be 10,000 to $15,000. So it's awesome to get that wiped off the books. But then you have to be ready come April of like a really high tax bill that maybe you weren't prepared for it.
Matt
It's a ticking tax time bomb that's going to hit people about this time next year.
Joel
Yeah.
Matt
And don't say we didn't warn you. So you got it. Truly. I mean you got about 12 months. Try to figure out how much it is that you're going to owe. And I think there's other steps you can take too to kind of offset that potential tax bill because it's being, it's being taxed as ordinary income. And so your ability as an individual to reduce your taxable income by charitable giving. For instance, maybe last year you're like, you know, we set some money aside, but standard deduction is so dang high.
Joel
So you.
Matt
I don't. That's not a great reason to not give. But if you're looking at it from a tax perspective and you're sitting on that cash, oh, maybe you make that happen this year. Oh, maybe you up your pre tax giving towards retirement accounts. There are different ways to make sure that you're avoiding getting bumped up into that next tax bracket to where you have the cash on hand to be able to pay that tax when it's due.
Joel
Start planning for it. Alright, that's gonna do it for this episode. Matt, we have resources up on the website howtomoney.com, good stuff. So if you haven't checked that out, please do. And if you have, yeah, we got questions.
Matt
We got lots of stuff for you over there.
Joel
Lots of good stuff. If you have a money question we want to hear from you, just go to howtomoney.com ask record it on the voicemail your phone because guess what? On Monday we're going to have an episode that's dedicated to answering your questions. If you want your question answered, please holler at us. Yeah boy.
Matt
That's going to be it.
Joel
All right buddy. Until next time. Best friend out.
Matt
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Joel
Guaranteed Human.
Date: March 13, 2026
Hosts: Joel & Matt
In this engaging Friday Flight, Joel and Matt cut through the week’s money headlines to help everyday folks make smarter financial moves. The hosts tackle the promises and pitfalls of AI in personal finance, the proliferation of premium credit cards, the surge in side hustles (especially among Gen Z), and growing pessimism about retirement. As always, they share personal anecdotes, challenge fear-mongering media narratives, and empower listeners with practical, jargon-free advice.
Segment: 04:13 – 07:48
“If you’re part of the cutting edge—an early adopter—man, there’s just so many more reasons to kind of drive somewhat older vehicles... repair costs and the tried and true, the tested.”
—Joel (07:50)
Segment: 08:02 – 11:53
“I like how straightforward part of the card is… 10% on this and 5% on this—that’s a solid rate of return. But is that a game you want to play?”
—Matt (10:13)
Segment: 11:53 – 13:54
“AI might make mortgage underwriting a whole lot quicker… but I’d want real human beings vetting every single instance for a while.”
—Joel (13:35)
Segment: 13:54 – 16:51
“The world’s smartest technology is no match for the US tax code.”
—Joel (14:04, quoting NYT)
Segment: 17:01 – 22:58
“It’s easier to find your audience, more tools to help you run your business… But the noise is incredible, so being able to cut through it is harder too.”
—Matt (21:06)
Segment: 22:58 – 26:13
“Don’t put too much pressure on yourself… That’s the great thing—if you have a traditional job, you can put in as much or as little effort as you want.”
—Joel (24:29)
Segment: 29:09 – 34:33
“To present that as a credible attitude of the majority… that feels like fear mongering… All we try to do is empower folks.”
—Matt (30:04)
“The comfy—‘mirage’—of a comfy retirement. I’m just like, come on, man. Do better.”
—Joel (32:59)
Segment: 34:33 – 38:39
“You get too sophisticated for your own good.”
—Joel (36:25)
Segment: 38:39 – 42:02
Segment: 42:02 – 44:24
“It’s a ticking tax time bomb for next year… Don’t say we didn’t warn you.”
—Matt (44:19)
“Every tool—AI—it’s a double-edged sword… It’s a multiplier. If you want to do good with this tool, you can. It’s not inherently evil or righteous.”
—Matt (21:17)
“More people are in the upper class. The middle class is shrinking because it’s going up, not down.”
—Joel (33:50)
| Segment | Timestamps (approx.) | |-----------------------------------------------|-------------------------| | Electric vehicle cost pitfalls | 04:13 – 07:48 | | Premium credit cards debate | 08:02 – 11:53 | | AI in Mortgages & Taxes | 11:53 – 16:51 | | AI’s work impact & entrepreneurship | 17:01 – 22:58 | | Gen Z & side hustles | 22:58 – 26:13 | | Ludicrous Headline of the Week: Retirement | 29:09 – 34:33 | | BlackRock on “evolving” investments | 34:33 – 38:39 | | Landlord headwinds, supply & demand | 38:39 – 42:02 | | Tariff refunds & Costco | 42:02 – 43:28 | | Student loan forgiveness tax returns | 43:28 – 44:24 | | Quotes, wrap up, call for listener side gigs | 24:29, 32:59, 36:25 |
For more resources, side hustle ideas, or to submit your own money question, visit howtomoney.com.