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Joe
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Doug
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Robert Farrington
We heard you.
Doug
Nine years of bring back the snack.
Robert Farrington
Wrap and you've won. But maybe you should have asked for more. Say hello to the Hot honey snack wrap. Now you've really won. Go to McDonald's and get it while you can.
OG
They're dogs and they're playing poker.
Doug
Live from Joe's mom's basement, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor, Doug, and what tax software should you use to complete your 2026 taxes? We'll dive into all of your options on today's show with some help from Robert Farrington from the College Investor. In our headline segment, are we witnessing the great precious metals and crypto collapse? Was the drop a couple of weeks ago just a hiccup or should you run for safer pastures? And that's not all. I'm also going to lay some of my heart stopping trivia. Anya. And now two guys who are to personal finance what Bon Jovi is to rock and roll past their prime, but somehow bachelorette parties in Nashville still talk about him.
Joe
Well, wait a minute.
Doug
Joe and. Oh.
Joe
I don't know that that's fair, Doug. I think Jon Bon Jovi's got a lot going on still. Hey, everybody.
Doug
But I mean, let's be honest, the guy is. I mean, he's just not the same anymore much.
Joe
You think so? I don't know. I saw him all over the super bowl stuff.
OG
He was in one ad.
Joe
Oh, no, no. Then he was down on the sideline. They showed him on the sideline because.
OG
He was in the ad. They have to put all that together.
Joe
They got to do all.
OG
All the stuff. Contractually obligated screen time.
Joe
How much do you think. Do you think State Farm paid Jon Bon Jovi more or us more? When we were advisors? Probably us.
OG
It was the other way around. Bon Jovi paid State Farm.
Joe
Hey, I really want to be in your head. Can I, Can I, Can I get it on that? It is stuff to wonder here. Ten days after the Super Bowl. Much better than wondering about that game. Not that it was exciting for about three minutes.
OG
I Thought it was a great game. Yeah, well, defensive battle, I liked it.
Doug
I think real like people who are hardcore football fans, they appreciate that. But the casual observer you want to.
OG
See, you want it to be like 68, 67 with a game winning safety. I know.
Joe
People are like, hey, why are you bringing up a thing that happened 10 days ago? Well, because one of the big points we're going to make today, in the second half of today's show, we're going to talk about the meltdown that happened in precious metals and crypto a few weeks ago. I like waiting a little bit to see, you know, how's the dust going to settle before we kind of do the play by play. So we're going to dive into that later on. But first let's man for all of you, and this is most people now, now that Texas have been so simplified, you're wondering which of these many software options should I use? And that's when Robert Farrington enters from the College Investor. He's also our partner when it comes to our college guide. But today he's partnering with us because as those of you that have been with us for a number of years know, they just dive in deep every year and it's amazing all the work they do to put together this guide of which software is best for this occasion, which one's best for that type of person. So if you're an investor, you want to use this one. If you have student loans, you want to use a different one. If you maybe can free file, there's a third one you might want to use. We'll go over what they looked at in all of their research. So just an action packed show today.
OG
OG can we.
Joe
Yeah, we are going to get on with it. But first we got a couple sponsors who help us keep on keeping on. You pay nothing for this Goodness. In fact, Doug Stack of Benjamin show always free, worth every penny. We're going to more, more of that coming up. So we're going to hear from the sponsors and then Robert Farrington from the College Investor, a fantastic website that does tons of research every year into what they found to be the best, best tax options for you when it comes to the stuff you use to prep your taxes. We're going to dive into all things tax software with him in just a moment. And we're super happy he's back in the basement. Robert Farrington joins us. How are you man?
Robert Farrington
I'm doing well. How are you doing well?
Joe
I'm doing better now that I'm about to know what software I need to use. I know that you and our good friend Eric Rosenberg who joined us last year, you guys as a team just really dive into this in a way that I couldn't even, I can't even imagine the work that goes into this every stinking year.
Robert Farrington
Robert, you mean you don't like filing mock tax returns across a dozen software programs? Like, come on, that's the best thing to do in November and December. What are you talking about?
Joe
I feel like for this you guys are like our version of Consumer Reports. Like Consumer Reports on best software.
Robert Farrington
You're not going to find me installing a dishwasher in my family room to try it. But I'll, I'll test the tax software out. Let's do it.
Joe
If it's a financial thing, maybe 529 plans, you'll do that. But not dishwashers. Let's start here. Because last year there was an overthrow of the king or the queen. We had one winner year after year after year that was best overall. But last year you guys said that was no longer the case and finally the king was overthrown and that that company was Free Tax usa. That was your champion last year for the first time. Let's just cut to the chase, Robert. Is Free Tax USA your overall champion in 2026 for our 2025 Texas as well?
Robert Farrington
Yeah. FreeTax USA is where it's at. It's our overall pick for the best tax software. Covers the most robust circumstances. It's a good just all around pick. And it is free federally. I always joke because the name kind of throws you for a curveball if you live in one of the 37 plus states that require a state tax return, aka most states. Yeah. But for you lucky Floridians and Texans, like it is free because you don't have a state tax return.
Joe
It is funny. Free tax USA *. But even without the asterisk, what is it about Free Tax USA that overall just makes it the grand.
Robert Farrington
Champion? Price comes down to a big part of it because you have to remember filing your tax return is literally data entry. And Free Tax USA makes that data entry easy, especially for most circumstances. Filing a W2 entering a few 1099, so easy to do. And it's free. And then the state is 1599 each. But even that is lower than pretty much every other competitor out there. And because it handles all those situations so well at a great price point, that's why we put it as our overall.
Joe
Pick. But that doesn't mean. And let's be clear here. People might be either watching the video or if you're listening to the podcast, you're like, okay, this is it, that's it. That doesn't mean it's necessarily right for.
Robert Farrington
You. Robert the big thing with tax returns is that everyone has so many unique situations. So while Free Tax USA is the good all around pick, you might not be an all around situation. You might be a heavy stock investor, lots of crypto trades. You might be a landlord, you might qualify for free federal and free state with some of these other programs if you have a very simple tax situation like just a W2. So there are more options out there. If you have some other situations you want to think about, we're going.
Joe
To walk through just a couple of others that you have. Overall, this is the champion. Until last year, you've got the runner up as the bajillion pound gorilla. Turbotax. Turbotax better this year, worse this year, more of the.
Robert Farrington
Same. You know, TurboTax is more of the same. They've just been rebranding a lot of their offerings and they are, I don't know if you saw this, they have launched physical offices. So TurboTax is really diving in in the head to head competition with H and R Block and some of the other ones. And I want to say they started with 30 or 40 physical branches this year in a lot of the major cities. They have a flagship store in soho, which if there's any New York stackers here, I'd love to see a picture of it because I have not seen it yet. But you know, they are going all in on this multichannel where you can start online and if you hit a road bump you can call, you could get virtual support or you could go into the store and get a real person to talk to. Which it's kind of interesting in this age of AI that real humans are really the focus of these.
Joe
Brands. But you've talked about that before. AI, especially when it comes to doing your taxes, could be a big.
Robert Farrington
Mistake. Huge mistake, because it just gets so much wrong in personal finances. One thing that I struggles with is all the state rules. Like I can't even get down the state rules and I'm a human. Every state's got its own little wonky local tax, state tax, what qualifies, what does, what matches. It's a.
Joe
Mess. But speaking of hdr, Block, that is your second overall runner up.
Robert Farrington
Again. They have the great multifunnel experience. So they've done this for years now where they offer Very robust support from real tax professionals. You can go to a store, you can drop off your returns at a store, you can upload files online. Just so many multiple ways to get help and assistance if you need it. Both of those options, TurboTax and HR Brock, you are paying the premium as a result of being able to access those services. But they are there if you think that's something that you.
Joe
Need. Does Eastern Our Block still have the big hang up that you guys had in the past, which is that you really aren't sure how much you're going to pay them until you go all the way down the rabbit hole? Or did they fix that.
Robert Farrington
Loop? Both TurboTax and H& R Block have gotten a lot more transparent in their pricing. However, Americans still aren't transparent on what tax forms they need when they start the process. So let's be honest, a lot of people don't necessarily know what you need when you start. You just start answering all the questions you're going through and then you suddenly discover yourself getting into a higher tier that you didn't realize was there. So going back to our overall pick, you don't have that with Free Tax usa. It is all free federally. So that's a very nice thing.
Joe
You'Re saying with these runner ups though, the problem might not be them, it might actually be.
Robert Farrington
You. It might be you just because you don't know what you need. And I find that with just a lot of Americans, taxes are a foreign language to a lot of people. So they might not understand that you have to file this form to claim that deduction. And that might be a deluxe or a professional version.
Joe
Right? We're skimming the surface here. Stackers. I'm going to link to the full deep dive in our show notes@stacking benjamin.com so you can go right to the college investor and get the best software because you're definitely going to want to dig in more. But I'm reading down through your piece and I see free filing and I'm like, okay, well the overall winner is Free Tax usa. It's got free in the title. So duh, this is going to be the winner in free filing. But it's not, it's not the winner. If you're somebody that can free file, you nailed.
Robert Farrington
It. So Cash App Taxes is our overall winner for free filing because they come in just ahead of Free Tax USA and they offer free federal and free.
Joe
State. So truly qualified.
Robert Farrington
Free. You got it. If you qualify to use it, it is truly free. And what I Say qualify. I just mean that you don't have unique tab situations. For example, they only let you file taxes in one state. So if you file taxes in two states and you might say, robert, what do you mean? Well, I know a lot of New Yorkers in New Jersey, folks that are crossing that bridge every day and you gotta file one and the other and get that washed out. And this happens in a lot of places. So if you need to file multiple state returns, it's not gonna be free for you. It doesn't even work for you. There's other situations as well, like if you have a K1, different things like that, where it doesn't work for you as well. So, so it's not all end all be all for everybody. There are limitations. And so that's why we put it in this category of free tax software. It is free for those that can use it and it's a great.
Joe
Tool. Some of these apps and Cash App is one of them, they have an add on called Audit Defense. What is, what is Audit Defense? Does that mean they stand by it if you get.
Robert Farrington
Audited? Yeah. So that means if you get a letter from the IRS and you need assistance with that letter, they will have tax professionals and attorneys there that can help you respond to those.
Joe
Letters.
Robert Farrington
Sweet. Provide that response to them. I know getting a letter from the IRS can be scary and that's what that upsell is.
Joe
For. They're owned by Square. Square is in a company that's known for losing money. How do they make money if they're doing all this stuff for free?
Robert Farrington
Robert? Well, they're trying to get you into their banking products so you don't have to use Cash App banking. But their goal is of course that you do use Cash App banking and use Cash App overall because they are trying to get you into their financial services platform. Now you can link your own bank account. When you do this tax return, you don't have to, you do have to sign up for a Cash App account though to use it, but you don't have to use their banking. But of course they are highly encouraging for you to use.
Joe
It. I would imagine they make it really easy for.
Robert Farrington
You. Yes, they definitely.
Joe
Do. Speaking of your runner up is another free filing that really want you to use their stuff.
Robert Farrington
Too. Yeah. So Chime is, I don't know, Cash App's one of their top competitors online. And last year, by the way.
Joe
I don't remember Chime, you're completely.
Robert Farrington
Right. So last year was their first year and we didn't Put them on the list last year because we're like, let's see how year one goes. And they got a lot of great reviews. People really enjoyed the platform and so this year we are putting them on the runner up. If you use Chime Banking or are curious about it, it's so similar to what you get with Cash app. It's still very robust. You can do a lot of things. It has some uploads. You can upload your W2, your 1099, but again it doesn't allow multiple states, can't file non resident tax returns, a few tax credits. You can't claim things like that that are limited. But if you don't have any of those limitations, it's a great.
Joe
Choice. It's interesting, Chime is this company that now has been around for probably a decade and they just seem to do things well. Like they, they tackle something and they do it well. And I feel like they don't do it until they do it well. That' endorsement of Chime, but just from afar, Robert, it just seems like that company just does a lot of cool.
Robert Farrington
Stuff. Yeah, I've seen that too. And I was a little scared when they launched their tax software because I remember when Credit Karma launched for the first time and it was like a derailing train of just terribleness. And it took them about two or three years to break sort out all the kinks and Chime came out of the gate with a really great product and not very many issues at all that I saw. And this year another great.
Joe
Product. So it is funny. I'm laughing, by the way. Not because it's funny, because if you were on that train, it wasn't.
Robert Farrington
Good. It was not.
Joe
Funny. Laughing because you can't cry. Well, I guess I could cry. Let's go to Student loan for student loan borrowers. Your winner here is Tax.
Robert Farrington
Layer. Tax Layer. I'm putting them up to like the number three biggest player in the space. Now. It used to be TurboTax H&R block and like TaxAct. But tax acts kind of fallen off and Tax Layer has just consistently improved their product year after year after year. And what I love about Tax Slayer is they have a classic tier and it has everything you could ever want in the product at the classic tier. So if you need to itemize, if you need to claim deductions that would raise you up into a deluxe tier at like a turbotax or an H and R Block. Well, you should just choose Tax Slayer because you're going to get all the same Stuff a great experience for a little bit less.
Joe
Money. It's interesting, last year Eric joined us and was really, I mean he talks so lovingly about tax layer. I was surprised that it wasn't your pick overall. Like it's that.
Robert Farrington
Close. They're just building a great tool out there. It's just, it's very hard to pass up free. Like it's. I just can't do, I can't give up free yet. I'm.
Joe
Sorry. I mean we've always said here that, listen, if you've got two competing products and one costs less than the other, then why would I pay more? It just, it doesn't make.
Robert Farrington
Sense. It doesn't make sense. But they have a great product so at their classic tier for like $22. So it's a little bit more includes all the forms. And tax Slayer's business model is that you actually only upsell for support. You get all the forms, you get all the things. At that 22.99, you're only paying extras for extra professional assistance if you need.
Joe
It. And again, most of us don't know if we need it until we, we need.
Robert Farrington
It.
Joe
Sure. H and R block number two. We talked about H and R block earlier. Cash App is here too. Why do you like Cash App specifically for people with student.
Robert Farrington
Loans? Because it is free. But again, when you start getting student loan interest, deduction, other things, we also find that those same individuals start running up against other things that might disqualify them from using Cash App taxes because they might have more unique situations. It might be a side hustler, small business owner. And that's where you probably want something a little more robust than what Cash App taxes is offering. But if you're just a 22 year old graduate and all, you got student loan interest and a W2 job. Cash app tax is a great choice if you don't have anything complicated to add into the.
Joe
Situation. Our goal here is to stack $100 bills and if you're doing that well, you're investing. So let's move into best tax software for investors. Your winner is the bajillion pound.
Robert Farrington
Gorilla. Still, turbotax is a great choice for investors because the one thing that TurboTax does that basically nobody else does is they have all the integrations. They have built that network that can import all of your brokerage statements into their software. And why we love it for investors is if you are a WallStreetBets stock trader, you love to do all the trades, pulling all that stuff in can save you a lot of time and effort. And so yes, you are paying a higher price point but the savings in your time and energy and effort can go just. It makes up for.
Joe
It. You and I have had a conversation before and we did a Friday fintech roundtable with some fintech founders talking about this problem that companies are starting to push back. Robert, about hooking things up easily. So JP Morgan is one of them that's really starting to push Capital One. Starting to push. Are we going to see in future years that hooking your stuff up to these third party tech software programs become more of a bear than they are.
Robert Farrington
Today? I don't know. But I do worry that it's going to become more expensive. I can't imagine that they're going to take the offering away. But building that out for consumers costs money. I don't think a lot of people realize that like every plaid connection or every data connection you're making to these banks and brokerages, these companies are paying for it. They're paying like a nickel a connection and account. And if you start connecting 10 accounts, it's like 50 cents a month per user times a million users. It really starts adding.
Joe
Up. Holy.
Robert Farrington
Crap. You start realizing why these aggregators like Monarch Money and others are charging monthly fees like they have to. It's either you're the customer and they're going to load you with ads and upsells and other things or they have to charge you because all these banks are charging them for that.
Joe
Access. It doesn't surprise me then if the bajillion pound gorilla Intuit is your first choice with TurboTax for investors. Well then certainly another company with a ton of infrastructure and one that's been around forever H and R blocks the runner up. That seems to. That's makes sense to me. You got.
Robert Farrington
It? Yep. Same deal. They have the imports, they make it very easy. And again this is really. If you need to import those transactions, if you don't, if you just have some basic, you know, 1099B with just one long term gain and it is reported to the IRS and you got just one box there, you don't need to use these tools. These tools are really handy though when you're trying to have an 8949 with like line after line after line of trades that need to be.
Joe
Reported. Crypto can be a bear, especially if you're buying it a little bit at a time because you're buying, you know, 1/100th of a coin for our crypto Fans out there, where should they go to get their taxes.
Robert Farrington
Done? It's the same 100 pound gorilla. It's TurboTax again. They have the best integrations. They link with Coinbase and some of the other major exchanges. They also allow you to upload a spreadsheet to create your Form 8949. So if you have a bunch of DEFI transactions that are just there, you can export them to a spreadsh sheet and create the tax forms you need. That can go a very long way. And I want every stacker to remember that this is the first year that we're getting the new 1099 DA. A digital asset 1099. So if you do have any trades on a centralized exchange, you're going to get that tax form and the IRS is now going to start correlating those things. So make sure you're reporting that stuff.
Joe
Accurately. It seems like five years later than it should have.
Robert Farrington
Been. You know, it's also. I find it very messy. I think a lot of those 1099DAs are not gonna be accurate because let's just say that you did stuff off a centralized exchange and you transferred into an exchange. If you didn't go into your Coinbase account and mark it as a transfer, it's gonna show up on your 1099 as a full gross proceed sale. And so you need to be very mindful about it because a lot of people that are in the crypto space actually only use their exchanges as on ramps and ramps. They're not using Coinbase as their main trading platforms. They're jumping over and doing DEFI stuff or staking or who knows what else. And then when they want the cash, they're bringing it back onto the exchange. You need to go onto the exchange and clear those out or else it's going to get reported and you're going to have a tax.
Joe
Headache. Well, they're not just doing that because of the fact that it allows you to do some of these other things that you talk about. It also seems to me to be safer just not to leave money there. I mean, all the reports we've had before where people have had money stolen while it's just sitting.
Robert Farrington
There. Joe's a crypto bull. I didn't realize it. Decentralized.
Joe
Currencies. Yeah, we just do so many stories about people getting ripped off in.
Robert Farrington
Crypto. It is, and it really goes down to that security. But like all that trading stuff happens off the exchange for a lot of these like meme coins and different.
Joe
Things. God, and then I imagine, then I loaded in just to make the trade and they go, oh, yeah, this, this is found money. So it's all, oh my.
Robert Farrington
Goodness.
Joe
Yep. If you're a landlord. If you're a landlord, what are we.
Robert Farrington
Using? I love Taxslayer. You know, we've tried some different picks here in the past, but Taxslayer, again, because you get that classic tier at 2299, it gives you all the forms you need. You can do the depreciation schedules, you can do what you have to do there for your Schedule E at that lower price point. And even if you need professional assistance and you need to upgrade, you're still cheaper than all the other platforms, even paying for those upsells. So taxlayer is a great choice for.
Joe
Landlords. I remember last year, Eric telling us, Robert, that this is really where Tax Slayer.
Robert Farrington
Shines. Yeah, it's a great tool because it is as good as all these big ones. Except the price point is just a fraction of the.
Joe
Price. There is where it is. Now, if you have a side hustle that isn't real estate, you've got a winner here. If I've got this side business, what am I.
Robert Farrington
Using? You got Cash App Taxes is a great choice for the basic side hustles. So if you just have a little bit of income, you just drove for doordash or Uber Eats and you want to, you still qualify for free. Check out Cash App taxes. But if you do need a little bit more, if you need to build out like the full schedule C and you have a lot of stuff that you want to input, check out that tax layer. Again, Tax layer is a great choice because again, you get everything at 22 bucks for it versus all the other ones like TurboTax and H& R block. You're suddenly in the self employed highest tier. You know you're going to be paying $100 plus for your taxes. You don't really need to pay that.
Joe
Much. A lot of people when they first start a side hustle, they forget, right, that I got to keep track of this stuff throughout the year. And then they're sitting there with markers that are four different colors and this make it up with what, their mileage? I'm not advocating this. I'm just telling you what I've seen people do. All right. Yeah, it's ugly when you start your side hustle. Some people, you know, they finally figured out that they should use QuickBooks 0 FreshBooks. You really give some good advice here. At this point in your piece about you know, maybe it's not about just filing time. Maybe there's some cool things you should be using to track mileage, to track your expenses. What do you guys.
Robert Farrington
Use? Yeah, so if you one, instead of highlighting everything and trying to do it at the last minute, keep track of everything as you're going. Start with so much easier. Makes it so much easier. If you're driving though, let's say you're doing one of these driving side hustles, delivery, food, whatever. Everlance is a cool tool because you could start your job, stop your job. It uses gps, tracks all your mileage there. And I believe it actually links up to one of the main apps out there. That way you have all your mileage tracked. Because one thing I've learned is that a lot of side hustlers, they go to file their taxes and they forget their deductions. So they'll say, like, I made twelve hundred dollars driving for Uber last year. But then you're paying taxes on the full $1200. But you need to deduct your mileage and you need to deduct any other expenses you might have. Did you buy a cell phone, any of that stuff? Because you probably didn't profit $1200. You probably profited half that or less after your expenses. And you don't want to be paying more taxes than you legally have.
Joe
To. This is a big problem for me. When I started my first business was that I did not understand any of what you just said, and I ended up paying a ton more in tax than I should have just because of my lack of understanding that. Speaking of that, because of that, Robert, I might need pros to step in, right? There are some people, especially when you start getting into small business. I own several rental properties. It just My taxes get more complicated. Maybe I'm in multiple states like you were talking about. If I need to have some pros help me through this, who's your winner.
Robert Farrington
There? Yeah. So Free Tax USA has an upsell, right? So it's free federally, but you can get Pro support for 4.99. So $45, which is probably the cheapest level of pro support that you're gonna see out there with great tax software that goes along with it. And then we also go to Tax Slayer Premium, Especially if you are a small business owner, their small business tier, which is a support tier, because remember, 22 ducks, you get the full thing. But you can upgrade to their small business tier. You get everything. And they have small business experts that can walk you step by step through These expense questions, and that's what they.
Joe
Do. Is it at this point, though, where you think people maybe are better served to find somebody locally that you can just look across the table.
Robert Farrington
At? It really depends on the person and what you're doing. I think if your business is starting to grow and you're having these questions, I think it could be very helpful to sit down with a professional to at least get organized and understand what you should be tracking. I think it's important to remember that filing your taxes is basically data entry. It is not going to help you save money on your tax return or anything. It is basically a report card of what you did last year. But there is tax planning, and this is where you can meet down with an accountant or a CPA and learn what you're supposed to do so that you know what to track, you know what to deduct, you know what accounts to do so that you set yourself up for when the data entry actually.
Joe
Happens. That's what really serves me, is I've got a person I sit down with once a month. We take care of it. My tax planning, when I have new ideas, when we have new income streams, we start planning around what we're going to do all year long. And of course, as you can imagine, Robert, that's a bunch more expensive. But I also have to tell you that when January hits, it's done. It is. It is done. I file my taxes so early every year because the fact I have that person in my corner. But I'm so glad we have you in our corner. By the way. That's not it. You go into if somebody needs a tax refund loan, if somebody has a true small business, not just a side hustle, what they should use. You walk through best tax liability calculators. If you're a NFT or a crypto trader, you dive into each of these companies and how each of them work and really get more granular about what you can expect from all of all this software. I just. It's exhausting talking about it. Robert. Again, like I said at the top of this, I don't know how you guys did it, but great job as.
Robert Farrington
Always. I appreciate it. I mean, we actually start this back in the end of October every single year, because that's when these companies start launching their stuff. And we get in there and dive in and start making. Bob Vance from the office is our mock tax return. Every year we start making Vance refrigeration tax.
Joe
Returns. That's fabulous. Bob gets a.
Robert Farrington
Workout. Yeah, he does. He Files a lot of tax returns every year. I hope the IRS doesn't catch.
Joe
On. We'll link to the piece@stacking benjamin.com or you can go directly to the collegeinvestor.com this time of year, Robert always has it right on the front page. You've got the website right there that you could just clink.
Robert Farrington
Through. Thanks so.
Joe
Much. Clink through. Clink, Clink through. I don't know where clink through comes from. You can also click through. Or you can click through. Robert, thanks for helping our stackers again this year. I really appreciate.
Robert Farrington
It. Definitely. Thanks for having me. I'm Rocky Lalvani, the profit answer man. And when I'm not helping small businesses stack Benjamins for themselves, I'm stacking Benjamins for.
Doug
Myself. Hey there, stackers. I'm Joe's mom's neighbor, Doug, and on this crazy holiday calendar Joe's mom got me, it says that it's thumb appreciation day. Man, if it weren't for my thumbs, I don't know where I'd be. Maybe like just an ape. Oh, they. They got thumbs.
Robert Farrington
Too. All.
Doug
Right. Maybe I'd be like a raccoon or something. Well, all right, fine. My bad. Probably it's just time for me to stop. But when I think of all the help my thumbs have been all these years, I mean, they've really opened some doors for me. Pause for laughter. Today's also the birthday of Queen Mary the First who lived from 1516 to 1558, just a few short years before Joe. No, Mary shares an unfair, unfortunate nickname with a drink. Lots of bars, restaurants and brunch lovin tailgaters have stirred up for friends. So today's question. What's the name of Mary's drink? I'll be back right after I find out who was queen after Mary. Sounds like this lady didn't have much of a sense of humor. Hey there, stackers. I'm guy who loves just about everybody. And also guy who's a better bartender than Isaac from the Love Boat. Look it up, kids. Joe's mom's neighbor Doug. That'd be a fun retirement job, wouldn't it? I mean, making drinks for all your friends. So many drinks with so many great names. But one classic is a nickname shared with Queen Mary the first named Bloody Mary for her intolerance towards non Catholics, many of whom she had burned at the stake. It seems unlikely name a drink after her. And yet a tomato juice based drink with celery universally loved by brunching soccer moms and college football Tailgaters also goes by the same name. Hey, Ma, on my next one, how about you spill a little vodka in the.
Joe
Glass?
Doug
Geez. And now two guys who share a name with one of America's founders. Maybe a little more savory Joe and.
Joe
Og. That is quite the story when you look up where the name of the drink came from. Like, I don't.
Doug
Know. No, you wouldn't drink so many of.
Joe
Them. No, no, we want nothing to do that. By the way, you asked the question, Doug, who was the queen right after Mary died? And it was Queen Elizabeth the First we were talking about on our trivia just.
Robert Farrington
Recently. That's.
Joe
Right. Now you know the rest of the.
Doug
Story. The rest of the.
Joe
Story. Look that one up, kids as well while you're looking it up. Big thanks to Robert for stopping by. And just the work they put into that, guys, is just unbelievable. The huge amount that goes into helping you decide which software is best. And so big thanks to them for doing it because, man, we didn't want to do that research. They seriously dive in. Let's. Speaking of dive in, let's dive into a headline. Hello.
OG
Darlings. And now it's time for your favorite part of the show, our stacking Benjamin's.
Joe
Headlines. Well, a couple weeks ago we had a big old meltdown in the precious metals markets as we saw silver lead the way and then gold and then of course crypto as well drop tumultuously. Gold saw its biggest daily drop since the early 1980s. Silver went down more than 25% when this all came to pass. Initially, the volatility came alongside a wider stock market sell off where the major averages all lower. After President Trump selected Kevin Warsh as the next Federal Reserve chair, the nomination appeared to ease concerns about the central bank's independence, given Warsh's historically hawkish stance. When you read about, quote, what the market thought, oh gee, which always makes me laugh because the market never thinks one thing. But all of the news organizations talking about the market liked the fact that war seems to be a good pick for our next Fed chair. But clearly the markets decided that holding all of these metals might not be something that we would need as much of. I mean, this was huge volatility when we look at since the 1980s. OG Any insight into why we saw these just gigantic seismic moves in precious metals and in.
OG
Crypto? No, no insight whatsoever. Because ultimately prices of things that don't produce any value are going to be much more volatile than things that have earnings that are tied to them and produce Economic output, obviously, gold and silver for the last, what, maybe two years or so, maybe two and a half years, have been on a pretty gigantic tear. I'd love to have Len's take on this because I know he's been a silver guy for finally with winning 72 years. He's like, I told you guys, okay, I think this is true for any asset class that you catch wind of and find out the results of in the back end. And what I mean by that is, you go like, whoa, GameStop's up 3,000%. Like, what the heck? How come I don't have any GameStop? Or Gold's up this big number, silver's up this big number, or whatever. How did I not get in that on that? And you just have to go back to what it does and what it suits your portfolio as to begin with. You know, if you didn't own silver as a diversifier in the last 15 years, going up to the ticket window, going like, well, I need silver as a diversifier is just completely lying to yourself as to what you want to have it for. Because you're just going. You just see the price. Because for 15 years it was at 20 bucks an ounce. Never once did you think, I should have this as a diversifier because I like to not make money for 20 years. You gotta be true as to why you're attracted to something. The reason you're attracted to something is because all of a sudden it looks cool. All of a sudden it's up a whole bunch. I never thought about owning GameStop ever. And then I saw it was up like a bajillion percent, I was like, well, I mean, maybe I should own GameStop. What do I know, you know what I.
Joe
Mean? A certain amount of.
OG
Fomo. Why do I want to own it? Well, because it looks like it's, you know, whatever. Same thing with Bitcoin, same thing with silver. And even with the volatility, I think the volatility is one story, which is what did it go from 115 an ounce on silver down to 75 in a nanosecond? Which isn't the interesting story that I found, by the way. Interesting story that I found was the guy who put 35 million of his own money against a loan of 200 million the day before and bet against.
Joe
Silver. A leveraged.
OG
Bet. He put $200 million on a bet that silver was going to go down roughly 12 hours before it went down 30%. Eh, I don't know. Does that pass the sniff test? No, it does not might be.
Joe
A little market manipulation going on there, you think? Or just somebody who might know a little something, something about who the next Fed chair would.
OG
Be. Or it's like the guy who made a $50,000 bet on Poly markets that Maduro was going to be arrested sometime this month. Like literally three hours before he got.
Joe
Arrested. So.
OG
Weird. Listen, I'm all for if that was like an Air Force pilot or a Delta guy on the helicopter going, guys, you want to see how to make some money? Watch this. I'm all for that. Like, I'm good with that because, you know, we don't pay our service members.
Joe
Anywhere. A little overtime pay, little overtime.
OG
Pay, a little something for the effort, you know, as they say, say, I'm good with that. Some Wall street dude that's friends of a friend that can borrow $200 million against his 30 million to go make a free 60. Seems a little, seems a little silly to me. But volatility, I think is one story which goes to show literally how volatile any one asset class is. There's plenty of people, Len, I think would be one of these guys who are still sitting on a big gain on the value of their silver investments. There's a whole bunch of people that bought at $110 a share that are now sitting at a 30% loss on their silver. So you have to remember, whether it's gold, silver, bitcoin, or an individual stock or an individual country, anytime you narrow your investment thesis to one specific idea, you increase the range of returns by an order of magnitude. So when you think like, oh, the only thing I can invest in is this, you are narrowing your focus to that one particular thing. Your range of returns is going to be wildly all over the place, which can be good. You can get a wild return on the upside, or you can get a wild return on the downside, but you're going to get a wild.
Robert Farrington
Ride. One.
Joe
Way. This goes back og to a couple weeks ago when we were talking about thinking in terms of probability, right? And I think what you're talking about is I can say I'm investing in mid cap stocks or I can reduce that to the tech sector. The probability is going to swing much, much more just going tech stocks versus mid cap stocks. But then if I just say Nvidia, it's going to be even wider. Like who knows what new news Nvidia is going to come out with tomorrow, we have no idea. Or competitive news like we saw with the Chinese company that came out, you know, and surprised everybody one morning with hey, guess what, we can cut them off at the knees. We don't have any idea. Strategists said gold and silver's epic rally was due for a pullback. The higher metals rise, the more likely 2026 will mark enduring price peaks, notably for silver. If history is a guide, Mike Magloney, senior commodity strategist at Bloomberg, wrote. And then he said there are always sound fundamental reasons for rallies. But when prices rise as rapidly as they have in metals and deficits can shift fast, he added, meaning the further this stuff goes up, the easier it is to poke a pin in it and it just comes back to.
OG
Reality. Listen, the easiest way that I can think about this is it's like pulling a rubber band. The further back that you pull a rubber band, the more it's going to spring in the other direction. It's a good analogy for when things don't go well. You know, think about COVID in 2020 when in 17 trading days the market was down 34% and we're like that's a pretty big pullback in a really short period of time. It stands to reason and this is what happened. Although it's not predictive in nature, just logically can make sense. That's kind of a knee jerk reaction and then we'll find where it should be after more data comes out. I think it's true for like I said, any asset class that you narrow your focus into, you're going to start seeing increase volatility if you just pay attention to that asset class, you.
Joe
Know, with the relative long term calming feature that gold can have on a portfolio. Stacker Dave in the that's a.
OG
Funny way of putting it. Doesn't do anything for 30 years but go.
Joe
Ahead. Stacker Dave in the basement Facebook group asked the question which is people see these long time sits and they go hey maybe I should have some gold as part of my emergency fund. And then I brought up the fact that gold on a daily basis incredibly volatile. In fact I had it put up in front of me that I've quoted long time financial writer Walter Upgrade is saying it's eight times more volatile. That is a true quote. Walter Upgrade did say that. I've quoted Walter before but even without this time we will see on a daily basis 3, 4x. I don't know if it's 8. I haven't taken the time to look at what is generally 0 to 5% of any average portfolio to look into it. But you don't want imagine if somebody had gold is Their emergency fund. And then the day after this happened, I needed to sell it off to buy a new vacuum cleaner or whatever, whatever the deal, whatever the deal might be to get a car repair done. And my gold dropped through the floor. So I think that there's a big difference between daily volatility and what it does over long, long, long periods of time. The other thing that I found fascinating about this OG was I had heard from you the story of the guy with a big silver bet. So I went looking and I found on TikTok a video of Peter Lynch. The Peter lynch, the guy that ran Fidelity Magellan that did phenomenal when he ran it. Peter lynch talking about this. Let's listen to what he said about silver during this volatile couple of.
Peter Lynch (AI voice)
Days. Listen to me very carefully. While you were sleeping on Friday, JP Morgan closed their entire short position in silver at the exact market bottom. And they are laughing at you right now. I am not making this up. I am not exaggerating. I am showing you with numbers and timestamps how the largest banks on planet Earth just executed the most perfectly timed trade in 44 years. $3 trillion evaporated in 24 hours. Silver crashed 35%. Gold fell 12%. Mining stocks got obliterated. And you were told it was because of Kevin Warsh. That is a lie. Fast forward to 2011. After the 2008 financial crisis, people lost faith in banks. They piled into gold and silver. Silver went from $18 to $49. What did the CME do? They raised margin requirements five times in two weeks. Leveraged traders got flushed out. Silver crashed almost 50%. December 2025, silver hit an all time high of $84. The CME raised margin requirements twice during thin holiday trading. Silver crashed 13%. I told you about that. I made a video. I said this was.
Robert Farrington
Engineered. And.
Joe
Now. And he goes on with this.
OG
OG and it sounds like so much AI. I don't, I don't know that. I mean you have like a check mark next to that guy's name to know that it really was Peter.
Joe
Lynch. Let me tell you what's amazing about this was that I saw that video and I was incredibly interested to hear somebody like Peter lynch going into all of these specific times and all this specific stuff. And then I clicked on this guy who has 8, 200 followers, the finance guy who posted this. I don't know what his agenda is. And then you look further into this video and Peter lynch said nothing. Peter lynch never said anything. This is a hundred percent AI, okay? This is a Hundred.
OG
Percent. My BS detection went really high. Like, he started, like, the timing on it was a little.
Joe
Off. But what's amazing about that OG is I believe that's because you do this every day and, and you're like, I don't.
OG
Know. Plus, wouldn't Peter lynch, like, seriously be like 90 something right.
Joe
Now? I know the average person is gonna see just go, oh, yeah. This looks like Peter lynch in his prime, by the way. Yeah, looks like the old Peter Lynch. But it is so frustrating that something like this happens. And when's the time when you're going to make a mistake, guys? You're going to make a mistake when all of a sudden stuff's being pulled out all around you and you're going to start going to places like this finance. The finance guy and his Peter lynch video. And by the way, not the only Peter lynch video he's posted. And he's not the only one OG posting videos of Peter lynch commentating about things going on in the stock market that aren't true. It's.
OG
Ugly. So all of that, there's no JP Morgan, short position, CME margin. Blah, blah, blah, blah, blah, blah, blah.
Joe
Blah. Smoke, meat, mirrors, dogs, meet ponies. Ugly, Ugly.
OG
Ugliness. I mean, that's not to say some of that's not true. I mean, maybe J.P. morgan did close a short position 100. Maybe they. Yeah.
Joe
Whatever. What's the best lie you can tell? Right? The best lie you can tell is one that's 97% true and it's that.
OG
3%. Oh, God. Yeah. We are so.
Joe
Screwed. Yep. People taking advantage of people not knowing any better. Watch out for AI people. It's ugly. All right. I will link to this, by the.
OG
Way. I don't do a lot of social, as you guys know, but when I see that stuff I file. I. I do like the, like, complain button every time. Every.
Peter Lynch (AI voice)
Time. Not.
OG
That. Like, it's my little like. Like I've been chewing some gum and the dam's about to break and I'm like putting my little piece of gum in the one, like, leaky section. That's all I can do. Like, I'm.
Joe
Just. And then, you know what's frustrating, OG Then the powers that be do exactly with this video what they do with our show when there's an AI show spoofing our show right now. You know what they do?
OG
Nothing. Not our.
Joe
Problem.
OG
Nothing. We love the.
Joe
Clicks. Even though, even though Spotify and Apple. It says right on your stuff that if it's AI generated, you're Getting the boot. Show us Boot. This AI show calling itself Stacking Benjamins. It's incredible. Anyway, not that I have an ax to grind on this.
OG
Topic. No.
Doug
It'S. It's.
Joe
Legit. It is legit. It's. It's so frustrating. We'll link to this in our show notes@stacking benjamin.com. and I'll also link to that video so you can.
OG
See. Imagine if one day somebody sends us a letter and says, I was really surprised to learn that you guys decided to go all in on whatever, horrified. And we're going, what the hell is this person talking? Based on your recommendation. I mean, I bought into the apartment complex like you said. I mean, you guys are putting your money there. I mean, it was good, but, you know, whatever the hell happened to my $10,000, you know, or like.
Joe
Whatever. Yeah.
OG
Right.
Joe
Like. Oh.
OG
Don'T. That kind of happened to Paula a little.
Joe
Bit. Right. She gets spoofed on. She's been spoofed on social media two or three.
OG
Times. Yeah. I remember she posted something that was like, I will never ask you for money or to invest side by side with me on anything. So maybe we should say that very publicly. We will never do that. We will never ask you to invest in a venture that we're doing together. That's not a thing that we will do or have done.
Doug
Ever. We really almost never give specific investment advice on a spec, you know, I mean, commodity.
OG
Short. Short silver. I mean, obviously.
Joe
That'S. You wonder who the guy was that leveraged that bet the day.
OG
Before. It's a baller move, man. I. I mean, I respect it. I think it's total BS. But to put 30 mil of your own money, I mean, is that a YOLO trade? Is that like. Do you think.
Joe
That'S. They called.
OG
It. He had gone from a hundred down to thirty. Was like, this is my final.
Joe
Hurrah. Yeah. Either way, your money's not going to matter.
OG
Right. Or is this a slush fund of like 30 mil that's left over? Like, Like. Yeah, I mean, let's short. You know.
Doug
What? I got an.
OG
Idea. Let's borrow 7x and short 200 million against our 30. I think it's going to go down tomorrow. Oh, wink, wink.
Joe
Wink. Bam. Couldn't have called it better. Doug, let's wander out on the back porch because we've got a couple things here. Please join me if you're around Omaha on Friday, and I know, by the way, Saturday and Sunday, the. The 1% better conference still has some tickets left. And we'll link to it on our Show Notes page. But on Friday we'll be doing a meetup at omaha stacking benjamin.com meetup to come join us. And two weeks later I'll be in Seattle with our Benjamin's After Dark group hanging out at Capitol Hill Elysian Brewing. That starts at 6:30. That is going to be on March. Let me get the date. That'll be March 5th that I will be there. So come join me and all your Seattle stacker friends from the bad meetup.
Doug
Group. Will you be drinking Duncan coffee while you're there.
Joe
Joe? Well the it appears that since Seattle won that the Boston group is going to have to have.
Doug
Starbucks. Oh, is that the way it worked?
Joe
Okay. Yes. So the deal was was if the Patriots won, the bad group in Seattle was going to have to take a picture of them drinking Duncan coffee. Of course. Big Boston brand and then the opposite. So Boston, their first meetup coming up March 11th. They're going to be having to hold up at their very first meeting. Everybody's gonna have some Starbucks as the Seahawks brought it home. But anyway, for all of our meetup groups around the country stacking Benjamins.com bad for Benjamin's after Dark. For more on my stops in both Seattle and in Omaha stackingbenjamins.com meetup a couple other things by the way, we're going to be doing a live show. More on this coming up next week live show in Texarkana. But how about that does that Is that.
Doug
Wild?
Joe
Wow. It's incredible. We'll be at Texas A M, a joint project with Texas A M in front of students and community members. So if you're anywhere close to our hometown of Texarkana, come see us. And our amazing special guest Paula Pant will be here for this joint Stacky Benjamin slash Afford Anything episode. Also meetups coming up in New York City and Charlotte, North Carolina. So New York City can tell you we got that happening. Plus our Tucson group getting going. Two groups in Minnesota. Just a lot of fun around the.
Doug
Country. It's.
Joe
Happening. It is happening. It's rolling, man. Hope to see a lot of you in the next few months as I travel around the country. Right now though, we're traveling to the end of the show where we ask Doug what should be on our to do list today, my.
Doug
Friend. Well Joe, first, take some advice from our tax software segment. Don't settle for the best overall software. Find the one that's right for you. In fact, do that with all of your financial advice. Second gold and silver pullbacks. That's how these markets operate. But the big lesson, if you're going to become a famous bartender, you need to have a drink named after you. All I can come up with is Doug's dump Truck. I need some help. Stackers. Let's hear what you got on Facebook. Doug's dump Truck. I mean, it's got a ring to it.
Joe
Right? That sounds like a hangover. Like I am going to have the biggest.
Doug
Hangover. Oh, I've got a dump truck on.
Robert Farrington
Me.
Doug
Thanks. Thanks to Robert Farrington from the College Investor for joining us today. You'll find the entire gift guide to tax software@thecollegeinvestor.com we'll also include links in our show notes@stackingbenjamins.com this show is the property of SP Podcast, LLC, Copyright 2026 and is created by Joe Salcehei. You'll find out about our awesome team@stackingbenjamins.com along with the show notes and how you can find us on YouTube and all the usual social media. Social media spots. Come say hello and oh yeah, before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug. And we'll see you next time back here at the Stacking Benjamin.
Joe
Show. Sa. Time for a quick roll call. As many of these as we can do in two.
Doug
Minutes. How about that on my reviews of things I've watched.
Joe
Recently. Yes, because you've watched a lot of.
Doug
Stuff. I have. So whenever I put these lists together, I start to get worried about myself. Like, God, I need to pick.
Joe
Up a book or you need a.
Doug
Friend. I do, I do. I've actually read quite a few books recently and also managed to watch all this. So here we go. The Pit season two. I like it better than season one. I think they're trying to force topics less. It's just good er room drama and not so much trying to fit every social, you know, major hot button topic into the plot line. So I like season two.
Joe
Better. I did hear at a party, by the way, last week about the guy that had a four hour.
Doug
Problem. Oh, yeah.
Joe
Right. A guy with a. Yeah. Which if it makes it to.
OG
A party you go to.
Joe
Joe, it is. My wife is in the medical field. So the stuff that, you know, clears the hurdle of things to talk about in polite company was but yes.
Doug
The crazy rashes that woman must have seen at.
Joe
Parties. Oh.
Doug
Man. Landman. Season two, horrible television show. Amazing Billy Bob Thornton.
Joe
Monologues. All I hear about is how much people like it. Though I was sitting next to somebody at dinner on Friday who talked to you guys. Both shaking your.
Doug
Head. Now, as a construct of a storyline, it's a train wreck. It's a complete mash pile. Mosh.
OG
Pile. They rushed it. Plot lines, for some reason, I don't know what they did, but they did it bad.
Joe
Yeah. We got 45 seconds.
Doug
Doug. Now, because you got. You give me these time limits and then you chime in with your.
Joe
Own. We can do the rest. I just said, how many are we going to get through in two minutes? I didn't say we had to stop. We can do another one. Another.
Robert Farrington
Time.
Joe
Time. Now we're down to 30 seconds because you complained about it. What's up.
Doug
Next? The rip. Really fun ride. Lots of good twists near the end. Other than a completely implausible chase scene, really fun movie to watch. Would.
Joe
Recommend. What's the rip on Netflix. It's on Netflix. I haven't even. I mean, but I love the way you skipped down because you knew the next one on the list I comment on, so you moved down to one that I wouldn't comment on. And that's gonna do it for today. That was two.
OG
Minutes. Two minutes sure seems like a long time when Doug's involved, doesn't.
Doug
It? Live from Joe's mom's basement, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor, Doug. And what tax wear. Geez. Doug.
Joe
Talks. Tax.
Doug
Wear. Tax wear. What underwear should you be? 3, 2.
Episode: Best Tax Software for 2026 (And Handling Market Drops) SB1805
Date: February 18, 2026
Guests: Robert Farrington (The College Investor)
Hosts: Joe Saul-Sehy, OG
Tone: Fun, approachable, conversational
This episode dives deep into two hot personal finance topics for early 2026:
The playful banter and lighthearted segments typical of Stacking Benjamins are preserved, but the core of the episode is a practical, expert-backed breakdown on tax prep solutions and some valuable reality checks for investors.
"You mean you don't like filing mock tax returns across a dozen software programs? Like, come on, that's the best thing to do in November and December." – Robert [05:44]
[06:48]
"Is FreeTax USA your overall champion in 2026?" – Joe
"Yeah, FreeTax USA is where it's at. It's our overall pick for the best tax software. Covers the most robust circumstances. It's a good just all-around pick." – Robert [06:48]
"While FreeTax USA is the good all-around pick, you might not be an all-around situation." – Robert [08:09]
[08:41-10:12]
"You can start online...call...get virtual support, or...go into the store and get a real person to talk to." – Robert [09:13]
[12:13]
Cash App Taxes
"They're trying to get you into their banking products...of course they are highly encouraging for you to use it." – Robert [14:18]
"Chime came out of the gate with a really great product and not very many issues at all that I saw." – Robert [15:34]
[16:14–18:39]
"Every stacker...this is the first year that we're getting the new 1099 DA...make sure you're reporting that stuff accurately." – Robert [22:05]
"If you’re driving...Everlance is a cool tool...tracks all your mileage." – Robert [25:51]
[27:25]
"Filing your taxes is basically data entry...But there is tax planning, and this is where you can meet with an accountant or CPA..." – Robert [28:09]
[34:06] Headline Segment
Joe and OG recount a recent historic drop in precious metals and crypto:
"Prices of things that don't produce any value are going to be much more volatile..." – OG [35:31]
"The reason you're attracted to something is because all of a sudden it looks cool. All of a sudden it's up a whole bunch." – OG [37:27]
"You don't want...if somebody had gold as their emergency fund...and then my gold dropped through the floor." – Joe [42:18]
[43:51ff]
"Watch out for AI people. It's ugly." – Joe [47:16]
"We will never ask you to invest in a venture that we're doing together. That's not a thing that we will do or have done." – OG [49:18]
For more lighthearted financial wisdom, tax guidance, and a break from financial doomscrolling, catch the next episode in Joe’s mom’s basement!