Tax season is here, and if you're like most people, you probably just want to get it over with. But I want to show you how to actually get value out of it. So today, I'll quickly walk through why paying taxes with a credit card can be an incredible way to rack up points or even make money.

Then I want to run through a ton of actionable hacks from the past few weeks, from teaching my kids to make serious money reselling gift cards and using card-linked offers, to a massive sign-up bonus, to stacking deals to get up to 30% off a Peloton, to sharing how changing the currency or location on your browser can actually save you a ton.

And finally, given the current market climate, I want to go deep on how I'm thinking about investing right now after we've all seen the S&P 500 drop 10% in two days. This episode's a little bit of an experiment in last-minute production, but it is also packed with a ton of tactics and practical takeaways.

So if you enjoy it, please share it with a friend or leave a comment or review. And if you want to keep upgrading your life, money, and travel, click follow or subscribe. First, I want to talk about taxes, which I know is really timely, but specifically paying your taxes by credit card, because I think it's a really interesting opportunity.

And given that taxes are due in a few days, I thought it would be great to get this out quickly. Apologies for the voice. I'm a little hoarse, maybe getting sick, but didn't have time to wait, because I know this is happening soon and some things have changed. So first off, taxes are not necessarily due.

You can file an extension, but your payments are due by April 15 or whatever day that gets slightly adjusted to every year based on the calendar and weekends. However, just to be clear, there are some safe harbor rules, so you can avoid paying penalties by paying at least 90% of what you owe this year or 100% of what you owed the prior year.

So keep that in mind. Make sure you make your payments on time. But I wanted to talk about making payments by credit card, because I think it's a really great opportunity. Now, this is a little bit of a different kind of episode. It is much more off the cuff.

In fact, I came up with the idea to put it out a few hours ago. I'm recording it just a few days before it comes out. Would love feedback on what this kind of off the cuff, little bit of a grab bag episode as we progress. What do you think?

Feel free to send me an email, a DM on social or anything like that. First off, why would you want to pay your taxes by credit card? Because it is not free. There are fees. And the way I think about it is there's really only one reason, and that's that you're getting a positive ROI.

Now, those fees range from as low as 1.75% all the way up to around 3%. We'll talk about that a little more, which means you need to be using a credit card that earns more than that for it to make sense. And I would argue a lot more than that, or at least a decent amount more than that, unless you're just interested in buying points.

Now, that might be a thing you are interested in. There's no easy way to buy transferable points from most of the different banks out there. So, this could be an opportunity to buy some transferable points, but I think the really interesting opportunity is when you can use this to kind of earn more value than what you're paying.

And that could even be a spread on cash back. Or if there's a signup bonus you're interested in, but it requires a high amount of minimum spend, but the ROI on that signup bonus is really high, this could be an opportunity to do that. So, let's talk a little bit about the mechanics.

So, there are two providers right now that are directly easy to make credit card payments. I'll talk about a few other options, Pay1040 and ACI. Pay1040 is 1.75% for consumer and small business cards, 2.89% for commercial credit and debit. Then ACI is 1.85 and 2.95. So, in general, I would always be using Pay1040 unless you need to make more payments than you can make through Pay1040.

And one thing is if you're noticing you are using a business card and it's showing up as 2.89%, double check if you use PayPal as the form of payment, if you can get that payment fee to show up as 1.75 or 1.85%. I think that's a good wrapper if you want to avoid the higher fee.

So, if we're going to use the barrier as 1.75%, you can see a lot of circumstances where paying a credit card could make a lot of sense or even be profitable, right? If you had a 2% cashback card, it would be profitable. If you had a 2X points card where you get at least one cent of value, you could see that being better.

If you have a card that earns even more than that, if you had the US Bank Smartly card earning 4%, or if you had a card earning a signup bonus where you were going to get 100,000 points, obviously those cases all make sense as well. So, first, make sure you know that you're going to get more value than this.

Then, consider whether it makes sense. Now, these fees that I just mentioned are all for federal payments. Each state has their own rates and fees, so take a look into that specifically. As for how many payments you can make, technically, you're only supposed to be able to make two payments per tax period per type of payment.

Meaning, if you have quarterly estimates and annual taxes, you could make two payments for each of those. From my experience and a lot of other people's experiences, that limit is actually set up on a per processor level, and the IRS doesn't seem to have a problem with you making two payments with Pay1040, two payments with ACI.

You can also make payments in each person's name if you're filing jointly. They don't always get combined, and you may need to call the IRS to get them combined, but that is another option if you wanted to double the number of payments you want. Finally, if you want to make even more payments, there are services like Plastique and Melio, which I'll link to in the show notes, that have much higher fees, closer to 3%, but they would allow you to make more payments.

And potentially, there might be some taxes that you can't make payments through the two main providers that those would allow you to make. Now, personal tax payment fees, those credit card fees, are not deductions, but if you are making business tax payments, they are. So especially if you owe any business-related taxes, the fact that the credit card fee is a deductible business expense makes this even a better deal for businesses.

Now, if you want to go check all these payments you've made and make sure they show up, you can log into your tax account. You should be able to see all your payment histories. Another interesting thing, I can't promise the timeline by which this happens, but the IRS does say that overpayments will be refunded unless you owe a debt on your account.

So I have heard people making payments beyond what they owe, and waiting and filing and getting a refund. But I have also heard of people, myself included, who have waited many months sometimes for those refunds. So definitely keep that in mind. Make sure you have a plan to pay off that credit card before you're expecting a refund to come in time for that bill to be due.

So in general, this is a great opportunity, I think, for sign-up bonuses. Looking at a card, if you search around online, there are some cards that will even give you virtual card numbers, so you can use them right away. I've used almost all the tax payments we make at a minimum as an opportunity to make a small spread.

I've talked recently about how we have a few different Bank of America cards. We've done the Platinum Honors track, which allows most of those cards to earn 2.625%. So at a minimum, if I'm going to owe the IRS money, I could take the 2.625%, subtract the 1.75% fee, and I'm making about 0.875% spread.

Now, if you owe the IRS $500, it might not be worth your time. If you owe the IRS $100,000, and you have the credit limit across a few cards to support that, or you can pay it off over a few months when you're able to pay that card off and then make separate payments, could be really interesting.

So keep that in mind. Wanted to share this with everyone quickly because I think people often overlook the opportunity this presents to accelerate earnings on bonuses or even just earn some points, especially if you have an interesting card that earns 2 points per dollar on everything like the Capital One Venture or VentureX cards.

Now, to highlight an example of how great an opportunity a sign-up bonus could be relative to the fees for paying your taxes, I'm going to talk about a sign-up bonus that just came out this week, in fact, two days ago, for one of my favorite travel cards of 100,000 points after spending $5,000 in three months.

And this is a card that earns transferable points. If you go to allthehacks.com slash cards, you'll see it at the top of the list. I'll link to it in the show notes. But think about the cost to put that $5,000 spend, even if you didn't have it, would be about $87.50 if you were paying 1.75% in fees.

So you might think, okay, well, if I'm just earning one point per dollar, maybe that's not worth it because those points might only be worth $50 or $60. I'm going to pay $87 in fees. However, because there's a 100,000 point sign-up bonus, this looks very, very different. So worst case, I think you could use that sign-up bonus in the travel portal.

And this card makes those travel redemptions worth 1.25 cents. And so 1.25 cents times 100,000 points is $1,250. So if you're getting $1,250 to spend $5,000, that's a 25% effective cashback rate. Now, would I want to take a 25% effective cashback rate at a cost of 1.75%? Absolutely. Now, if you can naturally spend that $5,000 in three months, you might not even need to do taxes to take advantage of this bonus.

And that's probably one of the reasons that this 100,000 point sign-up bonus, at least in the points and miles world, is a bonus people have been waiting for because it's one of the best. You can transfer those points lots of places, which I think highlights how much better that bonus could be.

So for example, I've used these points to go to Hyatt. I've used these points to go to different airlines, where the end value ends up not being 1.25 cents per point, but 2 cents per point or more, which would make 100,000 points worth $2,000 or more. So if you're going to earn back $2,000 of value for spending $5,000, that's a 40% return.

And so I would challenge anyone who's eligible for this bonus, which does require not having the card currently, though if you have it, you can downgrade it to another no annual fee version of a card at this bank. And you can't have gotten this bonus in the last four years.

But the card has a reasonable $95 annual fee, a $50 credit that you can use for travel stays to offset that. I think it's a really great opportunity if you're eligible and you're interested in more points. There's a link in the show notes to a post about the card and the offer.

It's at the top of the best cards page. And as I always say, using those links on our site, it's a great way to support us. Thank you in advance. But if you find a deal elsewhere, always, anytime you're on our site, make sure you find the best deal.

We try to put the best deals, but if they're not there, go get the best deal. You definitely won't hurt my feelings. In the case of this card, I don't think there's a better offer anywhere else. But I just want to flag that if there is a great offer on our site, it means a lot when you use it.

Thank you so much. This episode is brought to you by FACET. Finding good and actionable financial advice is not easy, especially if you want it to come from someone who's acting in your best interest. So let me save you some time because when I shut down my financial planning firm a few years ago, we did a ton of research on who to recommend to our clients, and we landed on FACET.

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So head on over to chrishutchins.com slash FACET, F-A-C-E-T, to learn more about which membership option is best for you. That's chrishutchins.com slash FACET. This episode is brought to you by Viori, which is amazing because they are one of only the few brands I wear almost every single day. I've got a shirt on, I've got the core shorts on.

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That's V-U-O-R-I. Again, that's chrishutchins.com slash Viori to discover the versatility of Viori clothing. Exclusions apply. Visit the website for full terms and conditions and find the link in the description. So next, I want to jump into a bunch of great travel and savings hacks that I've come across recently that I really think you all could benefit from.

There are some referral links or discounts that I'll mention. I'll put them all in the show notes. Some of the times those benefit me because they're my referral link. In a few cases, I found a better deal than my referral link and I'll share that instead. That said, none of those brands have paid for me to talk about them.

So I just want to be really clear on what is and isn't an ad. If you do hear an ad in this episode, which you will, it always starts with this episode is brought to you by. Those are our sponsors. For what it's worth, almost all of those sponsors are brands that I love and most of those relationships came from me reaching out to them after I wanted to work with those products and services because I loved them.

But those are the ads and those are very different from if I want to share a product or service I love and include a promo code I found online or my referral link. That's just purely me sharing the things I love. So first off, we recently came back from a trip to Colorado and just a few things happened that I thought were interesting.

One, I've started using the Flighty app almost exclusively as the way I manage all of my travel plans with flights. And the coolest thing happened because Flighty is monitoring all the inbound aircraft and everything. I got an alert one hour before departure that they estimated that my departure would be pushed back by 15 or 20 minutes and it took a full 40 minutes before the airline actually pushed back the departure to the exact time that Flighty was estimating they would.

Now, it's no surprise that with all the data they have, they've probably learned, hmm, when inbound aircrafts on this airline are delayed by this much at this airport, it results in a delayed departure time of this. So, loved being able to get that notification early. Now, obviously, if your flight is delayed or you think there's an estimated delay, that doesn't give you free reign to show up at the gate when that new departure time is announced because airlines can pull those up.

So, I would always keep an eye on maybe the airline app or if you're near the gate, just double check that the flight's not leaving early. Obviously, if you're keeping an eye on where the plane is and the plane hasn't even landed, you're pretty safe. But just want to say don't 100% rely on any app telling you you've got an extra 30 minutes unless you're really, really confident.

Second, we were in the Denver airport and we used this lounge that United opened called the Club Fly Lounge. And it's not really a lounge. There wasn't really more than a couple places to sit. It was more of a grab and go with a barista making coffees and matchas and whatnot and then fridges and snack counters.

And it was just such a great experience, especially with two young kids, to be able to walk in, grab a handful of snacks, not feeling like I was not supposed to do it. You know, if you've gone into an airport lounge, you're like, Oh, here's some extra fruit. Let's hide it in my jacket.

You know, let's put it in a purse. In this case, that was exactly what it was designed for. We walked in, we stocked up on snacks, we walked out. We had those snacks on the plane. Kids had food to eat. It was great. I really would love to see more lounges doing that.

I think Delta is experimenting with one of those lounges somewhere. And I know United has a few. Can't wait to see more of those. And then last, we thought we were going to go to the Capital One Lounge, but we didn't have time. But I noticed in the app that there was a really long waitlist.

And you can join that waitlist in advance. So if you're flying anywhere and there's a Capital One Lounge and you want to join, you could join that waitlist as soon as you're on the ground. You could probably even join it from the air based on how long you think it'll be till you can go.

And then they give you 10 minutes to enter. So just something to keep in mind there. Next, I want to talk about Amex Member Week, which was super underwhelming with one exception. And it was a great opportunity to make a little bit of money and teach my kids a lesson.

And I thought it'd be fun to give a really concrete example on how some of these card-linked offers can add a ton of value. So the specific offer at hand was a $50 off $200 offer at Lowe's. Now, we're not in the middle of a renovation. We're not doing a lot of projects.

Saving $50 at Lowe's was not something I needed. And so normally, I would just completely ignore the offer. But Lowe's does offer the ability to buy gift cards. So I thought about the ROI, and it didn't end up being high enough that it was worth my time to necessarily leave work and go do this.

But I was talking to my kids, and I was thinking, well, do you guys want to go to the park right now and let off some steam there? Or do you want to go on an adventure where we can make money, and then you guys can decide what to do with it?

So I'll walk you through the deal and how it was a really great opportunity for them. So buying $200 worth of gift cards, for us, a lot of the best value gift cards were already sold out. I think other people got the same memo. So we ended up buying $200 Dick's Sporting Good gift cards, and we got $50 off.

So out the gate, you're getting 25% back. Now, we couldn't resell those gift cards at face value. So the $200 Dick's Sporting Good gift cards, we were able to sell for $0.88 on the dollar for $176. We took a 12% loss. And then because you can't choose which credit card you use, right?

You have to use the card that is linked to the offer. The points we earned on that was only about 1.5%. So if you take 25% gain plus 1.5% gain from the points minus 12% on the loss, we had about a 14% profit doing this, which meant that if we were spending $200, we were making $28.

Except because I use the Card Pointers extension, because I have Card Pointers Pro, which I'll put a link to in the show notes if you want 30% off. You can activate offers on multiple cards at once. And that's important because if you logged into your portal for your Amex account and you activated it on one card, you wouldn't have it on the other card.

So you might see that you have the offer, but when you go to add it, it usually only adds to one. But if you manage to hit Amex's servers at the exact same time for all your cards, which is what the Card Pointers extension does, then you would have that offer multiple times.

So we had that offer six times, so we ended up with $168 of profit from a trip to Lowe's. Now, do you want to take time out of your day to drive to Lowe's for $168? That is a very personal question and how you value your time. And I could argue that on some days, yes.

And on some days, maybe no. But do I want to take my kids on an adventure that allows them to own the process, understand how this works, and make $168, and then get to have a conversation about what to do with it? Absolutely. So we decided to take some of it and go buy ice cream.

My kids were kind enough to agree that they were so happy with how much money they had. They bought mommy and daddy ice cream, which was a really fun experience. And then we took their bank account and we said, let's put some of it there and we'll save some for the future.

And then we even took some of it and we decided to make a small donation. So we got to split it up and help them see the different ways they can use their money for different causes. It was a really great learning experience. But the high level is when you see these offers, definitely consider whether there are hidden opportunities within those offers beyond what you see at face value.

And here's a great example of another one that was a surprising last minute purchase. So my wife and I have been thinking about getting a Peloton treadmill for a while. We've had a bike. We've really enjoyed it. We've used the app for runs and we've been running a lot more.

And lately it's either been dark outside early in the morning or kids are napping so we can't go on a run around the neighborhood and we've wanted a Peloton treadmill. Now, we've been looking on Facebook Marketplace for a long time and Craigslist. And other than a bunch of scams that I've found, we have not been able to find one for a reasonable price.

And mostly not an unreasonable price either. They just seem to be very hard to come by. The retail price for a Peloton tread is $3,000 and we've seen them for maybe $2,600, $2,500, but nothing really less than that. Now, if you factor in the sales tax in California, that's an even better deal.

But even those are quite a drive, hour, hour and a half away from where we are. And then I got this email that the Peloton partnership with one of the credit cards I have was extended and is going to continue offering 10x points on Peloton purchases. So I thought, okay, well, those points when redeemed in the travel portal at a minimum are worth one and a half cents.

Now, I usually get more value than that, but that means that the Peloton was 15% off. Now, that's not bad, but I was starting to think, is there any cashback portal options? So I went to cashback monitor and I looked and I noticed that Rakuten was currently doing 2% back.

And if you link your Rakuten account to your Amex account, you can get 2x points. But that wasn't that exciting. I decided I wanted to wait for a better deal. And so I went into this app that I've recently found called SaveWise, which has a ton of features, some of which are overlapping with card pointers and some of which are overlapping with cashback monitor, which basically, they're a directory of all the different ways you can earn cashback, but they will also auto-activate some of the offers that are card-linked offers.

But the really cool thing they do, and I'll put a link in the show notes to what I think is a discount on the pro version for SaveWise, is they set alerts on cashback so that you can get it alerted if Rakuten's offers go up. So for example, I looked at the history.

So another cool thing they do is they show the offer history. Pro account goes up to, I think, 9 months. And I noticed that Peloton has been as high as 6% back on Rakuten, which is 6x Amex points, which is pretty exciting. So I thought, okay, if it can get up to 6x again, that would probably be enough for me to pull the trigger.

So we sat, we set up the alert, and then the next day, I got an alert that on Kudos, which is another cashback platform I've talked about before, you could get 12% back on Peloton. So now I'm thinking, wow, my card earning from the Peloton partnership is 15% off.

Kudos is 12% off. I think we should do this. We had no intention that day of buying the Peloton Tread. But at 27% off, it seemed like we had to go ahead and just do it. And so I start checking out. Everything's going fine. And then I get to the final checkout screen on Peloton.

And there were two things that made me think, could this get better? So there was a promo code field. And then there was a payment box that said, do you want to pay by gift cards? So naturally, my first step is go see if there's anywhere on the internet I can buy Peloton gift cards at a discount.

There was not. I couldn't find them. But worth a try. Next was promo codes. I started searching around. And I knew that there was a Peloton referral code where you get $100 off. And if I give you that referral code, I would also get $100. So I thought about sharing that all with you, except the $100 you get is off accessories.

And the $100 I get is off accessories. And I don't know. I don't need any more accessories. And then I found the World of Hyatt partnership with Peloton page. And there's a $100 discount that works on the bike, works on the tread, works on the row. And that seemed much more exciting.

So instead of sharing my referral code, I will share a link in the show notes to the Hyatt discount page where you can get $100 off, which depending on what you're buying, a bike would be equivalent of about 7%. The tread was about 3%. Now, all of a sudden, I was stacking my $100 off, my 10x points, which I valued at 15% off, my 12% off from kudos to get all the way to about 30% off.

Now, I did the math on what we were going to end up paying with 30% off. And I'm not ready to do this for a living. But that final price is low enough, based on my experience monitoring Facebook Marketplace, monitoring Craigslist, that I am almost 100% certain, especially because all of the Peloton treads I've seen out there, and this is probably true of bikes and bike pluses, are all usually one to two years used.

If I were to market that I could sell your brand new, just opened, still under a one-year warranty Peloton for 30% off, I think I could make a business flipping Peloton. So if you have these offers and you can stack them and you want to, I bet you could make $300 or $400 for every Peloton you flipped.

Now, I think the points earning opportunity for 10x is capped at 50,000 points. So there is some ceiling to what you could do here. But I think that it's at least worth exploring if you want a little side hustle and you want a little fun. But it's even more worth exploring if you want a Peloton.

So I'll put my links for SaveWise and Kudos and the World of Hyatt discount all in the show notes. I think the Kudos link is for $20 off. So I don't know what that would add, maybe 1% additional to all of this. But I thought that was kind of cool.

And if you're in the market for a Peloton, hopefully this helps you push you over the edge to make it a little bit more affordable. This episode is brought to you by Gelt. Now, when it comes to building wealth, taxes are such a big part of the strategy. And as tax time gets closer, getting prepared now is so important.

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A couple other things that happen. One, I noticed there was a discount for the hiking app AllTrails, and so I put that in the newsletter. But as I was reading the comments on Doctor of Credit, I noticed that everyone in the comments said, this is a terrible deal. Yes, AllTrails might normally be $50.

Yes, it's on sale for $20. But don't forget that their pricing is country-specific. So if you're currently traveling in India, you could get AllTrails for much less than $20. I think it was something like $5 or $6. And people are like, and also, did you know that you can use a VPN to see that?

And it just got me thinking, I didn't actually do this on the Peloton, but should I be using a VPN to basically not just sometimes price shop flights, which I've done in the past, but also to go and price shop anything I'm buying to see if the price is better.

And so that's something I'm going to add to my routine of all of the things I do before I'm shopping online because I thought it was pretty cool. And the VPN I use for all this is NordVPN. They have been a sponsor in the past. They aren't anymore. But I do think that they still have a discount that's pretty compelling.

If you go to the link in the show notes, I think it's also on our deals page. And I ended up picking NordVPN after a very detailed, thorough read of a Reddit post where it seemed like every single VPN software was compared on 10s or 20 verticals of features.

And I've been very happy using it. I don't think it's necessary for security. But I do love that if I were shopping for a flight within a region like Southeast Asia, I'd be able to use a VPN to mimic that. I also, there are a lot of times where credit card offers, especially with Amex, are kind of location or regionally specific.

So I've used it for those purposes. So usually it's a deal seeking tool, not a security tool. But in a similar vein to getting different prices based on what country you're in, getting different prices based on what currency you pay for is something that I came across twice this week.

So first on the Icon Pass, if you're looking for Ski Pass, they've gone on sale for next year. You know, we're more of an epic pass in terms of where we go. But the Icon Pass has a little drop down on the top of the page where you can choose to pay in US dollars or Canadian dollars.

And so if you choose Canadian dollars, the price goes down, depending on exchange rates, anywhere from 100 to more than $100. And so easy way to save on the Icon Pass is use a card with no foreign transaction fees, buy it in Canadian dollars. Similarly, I was helping a friend buy a ticket on the Eurostar train between London and Paris.

And the price of that ticket was about 5% cheaper buying it in euros than buying it in US dollars. So reminder, anytime you're buying something that is offered in multiple currencies, double check that it's not much, much cheaper in that other currency. For example, anytime you're overseas with using Uber, there's actually an option in the Uber app that they recently defaulted to one that is not in your favor, where they default price everything in dollars and do a conversion rate for you that's less favorable.

So you have to go in there and say, actually, always price in the local currency, and you will save money doing that. So definitely go into that Uber app and make that change. Unless you have a credit card that doesn't offer foreign transaction fees for free and charges you 3%, then it might not make sense.

However, one thing to keep in mind is that as of recording this, which is April 4th, 2025, some of those currency rates are changing drastically. And I actually wonder if that Icon Pass discount has gone down even further than when I first checked it. Because as almost all of you will know, and who knows what happens in the next three or four days between recording this and it coming out, but the US stock market is quite a bit down, over 10% in the last two days.

And I just thought I'd want to share a little bit about how I think about this situation. We talk about markets, we talk about investing, we talk about money. But usually timely things don't necessarily fit in because I'm recording this podcast days or weeks or sometimes even months in advance.

But with this experiment right now, I'm recording it a couple days in advance. And I thought it could be a good opportunity to share how I think about situations like what's going on right now in the markets. not from a political standpoint, but from a financial standpoint and an investment standpoint.

And the funny thing is, first off, I'm not really thinking about it a lot. Now, obviously, I don't like headlines of the market crashing. I'd rather the market be up 10% or 20%. However, one of the principles I adhere to is that all of the money that I have invested in the stock market is money that has at least a five-year horizon.

So if I have money that I need for a down payment, a tuition payment, anything really that I'm going to spend in the next five years, I keep that money in cash and not just 0% cash, but cash in a bank account or money market fund or treasuries that are earning hopefully over 4%.

And that means that unless the market doesn't recover over the next five years, it being down 10% right now or 20% or 30% or whatever that number ends up being doesn't have a huge impact on my life other than whatever emotional toll I let it take on me while it's happening.

And if you look at the data on what happens in the stock market over a period of, you know, one to 30 years, you see that the longer period you look at, the less likely a down trend in the market is. And so there's this great chart from Ben Carlson's blog, which I'm looking at right now, and I'll put up on the screen if you're watching on video or I'll link in the show notes.

And it basically looks at returns for the S&P 500 from 1993 forward in a increment of everywhere from one to 31 years. And what you'll notice is that if you look one year forward, there's six years where the market was negative. That makes sense. And the further you go down, there's less and less number of years that are negative to the point that by the time you get to a 11-year horizon, there was not an 11-year window starting from 1993 forward where the market was down.

And if you go to five years, there was not a year looking five years out that the market was down more than 2%. So this gives me a lot of comfort knowing that if I don't need this money for five plus years, there has not been a time in the past.

Now, we could make all the speculation about whether now is different than the past, but there has not been a time, at least according to this chart, since 1993, where the market stayed down 10% over a five-year window. In fact, the same is true over four years. It didn't happen.

You'd have to go to a three-year window to see a double-digit decline at any point in time since 1993. And once you get, like I said, to five years, it's pretty hard to find a decline lower than 2%. So I just try to accept that that's what happened in history.

That's probably, not certainly, but probably what's going to happen going forward. And so, yeah, it sucks and it burns to see the market down. But maybe on the flip side, it's a buying opportunity. Maybe any of the money that I have in cash that I also don't need for five years, maybe now would be a good time to put that money in the market.

I try not to keep too much cash on the sidelines, but every now and then, you know, it ends up happening. And honestly, right now is a time where over the next few months, I will probably take all the cash that we have that's not invested. Some of it because we managed to move 401ks from one provider to another.

And as modern as society is, the only way we could do that was by mailing a check, which meant we had to sell all of our holdings, mail a check. They got deposited and they didn't get automatically invested. And I've been trying to figure out when to do that, mostly out of just finding the time to do it.

Now seems like a pretty great time, right? Market's down 10%. Everything's on sale. Honestly, my only fear is that the market will go down even more and I will have missed an opportunity to buy even cheaper. And so the way I think about those things is I just try to come up with a plan.

So right now, I'm thinking my plan is deploy a third of the cash I have now, a third of the cash I have in a month, and a third in two months. And the reason I don't put it all in at once is like I said, I don't want the market to correct even more and feel like I missed that opportunity.

That said, if I were to put a third of the cash that I have in the market now, and the market were to drop another 20%, I'd probably pull that timeline up and put the rest of it in at 20% down beyond what we're at today. And if it drops further, I could live with that.

But I think it's important when you're thinking about these things to come up with a plan instead of just try to trust your gut each day because it'll always feel hard every day. Now, one thing I'm absolutely not doing is selling. Do I think the market could go down 20%?

I think it's really possible. I don't know, right? Like I have no idea. If there's anything I know that's certain, it's that I don't know, but it's possible that it will go down another 20%. Will I have benefited if I sold everything now, let the market drop 20% and put money back in?

Absolutely. Do I think there's any chance at all that if I took my money out now and the market dropped 20% that I would be able to time the bottom? Absolutely not. There would be nothing harder for me than to see the market down 30% and think this is the bottom with my entire portfolio.

It would just be so hard. The whole theory of catching a falling knife is very hard, though I guess in reality, it'd probably be easier to catch the knife than it would be to time the bottom of the market. And deciding to rebuy is such a hard thing that I'm just like Nick Majuli said in the interview we had a couple of years ago, which I will link to in the show notes.

It's just keep buying. And that's the strategy. And so that's the strategy I have adhered to. It's worked well. From data standpoint, it's also worked well, not just for me, but for anyone who holds for a long horizon. Historically, it has worked well. One other thing that I'm thankful for right now is that I have done a little bit of diversification.

Our portfolio is not entirely in the United States. We have a few international index funds and the international markets are down less than the US markets. Now, over the last, I think, five or 10 years, that hasn't been the case. And I've honestly been wondering whether I should have had an even simpler portfolio of just 100% US total stock market, VTI.

And when I talked with JL Collins last year, and we debated that specific topic on whether you need international exposure, I was almost convinced that it would make sense. But all the data, looking at correlations, looking at historical performance, would argue that the diversification of adding international two-year US exposure pushes you further out the efficient frontier and has better risk-adjusted returns.

So I didn't make any changes. And the current situation is a great example that you never know what the future holds. And diversification can be really powerful, both in stocks, bonds, and cash, as well as US international or other asset classes like real estate. So one thing that I am considering right now, and that I think some people could, just like I did during the pandemic, is when the market's down a significant amount, it is a good time to consider tax loss harvesting.

And the way that works is, if you sell a stock that you bought, and you sell it at a loss, you can take that loss and offset either other gains you have that year, or income up to $3,000. So if you have some losses in your portfolio right now, because I mean, I guess practically, if you made any purchase of most stocks or index funds in the last year, there's a pretty good chance that that current position is down.

So if you were invested in the total stock market, VTI, Vanguard's index fund, and you sold that, you could buy something similar like Schwab's US Broad Market Index Fund. And you'd maintain your exposure to that same asset class. But you would be able to capture those losses and use them this year to offset other capital gains or up to $3,000 of income.

So if you live in California, offsetting income tax, depending on your tax bracket, or probably true of New York and many other states, could be really meaningful. And certainly would be better than the 20% capital gains you'd pay if you were to hold that for a lot longer and pay capital gains tax.

So offsetting income is really interesting, though limited to $3,000 a year. Now, because I'm using Wealthfront, I don't actually think about any of this. It's all automated happening in the background. You know, it's one of the things I'm really thankful for is during the pandemic, the market was down.

No one knew if it was going to keep going or if it was going to stop. Do I tax loss harvest now? Do I wait? And my portfolio was totally automated. I didn't even look at it. But I ended the year with a bunch of harvested losses, which was not good from the perspective of losses mean the portfolio is down, but great from the perspective of the market recovered.

And so I was never unexposed to the market. I didn't miss all the gains that came after the losses, but I did capture those losses and I've used them for other gains to offset over the years since that happened. And so if you want to check out Wealthfront, it's a product I use.

They're not a sponsor of the show. I've got a referral link to get your first $5,000 managed free, but it's basically an automated investment portfolio. They'll help you figure out a portfolio that's globally diversified, all low-cost, low-fee index funds, and then they'll just automatically rebalance and tax loss harvest it.

I did work there. I am a shareholder of the company from working there. Huge fan of the product. And, you know, the majority of our net worth is sitting in our Wealthfront account. So that's how I'm thinking about the current market. That's a lot of what has been on my mind the last few days, some of the deals I found.

I hope this episode was interesting and helpful. Please send me a note. Let me know what you think. Should I do more episodes like this or not? Your feedback is greatly appreciated. You can send it to podcast at allthehacks.com. You can find me on socials. You can use the contact form on the website.

That is it for this week. I will see you next week.