Live from Joe’s mom’s basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What’s the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride?
Joe Saul-Sehy and OG are joined by Robert Farrington from The College Investor to break down the tax software landscape without the marketing fluff. Because if you’re our Stacker avatar, you don’t want hype. You want something that works, doesn’t overcharge you, and doesn’t suddenly upsell you because you clicked the wrong box.
Then in the headline segment, the crew digs into the sharp pullback in precious metals and crypto. Is this the beginning of something bigger? A buying opportunity? Or just another reminder that chasing shiny objects (literally shiny in gold’s case) can make your portfolio feel like a roller coaster?
As always, Doug brings trivia, there’s some basement banter, and the team separates smart strategy from financial fashion trends.
Choosing the Right Tax Software (Without Overpaying):
• Why FreeTaxUSA might be the best overall value for most Stackers
• When TurboTax or H&R Block make sense and when you’re just paying for bells and whistles
• The pros and limitations of truly free options like Cash App Taxes and Chime
• Why TaxSlayer can be a solid choice for student loan borrowers, landlords, and side hustlers
• What investors and crypto traders need to know about brokerage imports and the new 1099-DA form
• Why filing taxes is mostly data entry and where real tax planning can make a difference
• Simple tools to track mileage, expenses, and side hustle income without losing your mind
Bottom line: the best software isn’t universal. It’s the one that fits your situation without surprise fees.
Gold, Silver, and Crypto: What the Drop Means:
• Why assets without earnings (like gold and many cryptocurrencies) can swing wildly
• The danger of investing based on FOMO instead of a plan
• How concentration risk increases the range of possible outcomes, both good and bad
• Why short term volatility doesn’t automatically change a long term strategy
• The risks of misinformation, including AI generated financial advice that isn’t real
OG walks through how disciplined investors think during volatile moments: zoom out, revisit your allocation, and stick to your strategy instead of reacting emotionally.
The Big Takeaway:
Whether you’re picking tax software or deciding what to do during a market drop, the lesson is the same. Choose tools that fit your life. Build a plan before the chaos hits. Don’t let headlines or shiny objects hijack your strategy.
This Episode Is For You If:
• You’re trying to pick tax software without getting ripped off
• Markets are making you nervous and you’re not sure if you should do something
• You want to understand what’s happening with gold and crypto without the hype
• You’re looking for calm, practical guidance during a chaotic time
• You believe steady wealth beats chasing shiny things
Let’s Hear From You:
What tax software are you using this year and why? When markets get volatile, what helps you stay disciplined? Share your thoughts in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid an expensive mistake.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Our Mentor: Robert Farrington
Big thanks to Robert Farrington for joining us today. To learn more about Robert, visit The College Investor | Navigating Money And Education.
Our Headline
Doug’s Trivia
In honor of the birthday of Queen Mary I (1516 to 1558), who had an unfortunate nickname that’s also the name of a classic brunch cocktail, what is the name of Mary’s drink?
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Other Mentions
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Written by: Kevin Bailey
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Episode transcript
[00:00:00] opener: They’re dogs and they’re playing poker. Ah. [00:00:15] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. [00:00:30] Doug: Am 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? [00:00:49] Doug: 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 gonna lay some of my heart stopping trivia on ya. 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 ’em. [00:01:10] Doug: Well, wait a minute. It’s Joe and oh, [00:01:18] Joe: I don’t know that. That’s fair, Doug. I think, uh, John Bon Jovi’s got a lot going on still. Hey, everybody happy he is, but I mean, look, [00:01:25] Doug: let’s be honest. The guy is, I mean, he’s just not the same anymore much. [00:01:30] Joe: You think so? I dunno. I saw him all over the, uh, super Bowl stuff. [00:01:35] OG: He was in one ad. [00:01:37] Joe: Oh, no, no, no. Then he was down on the sideline. [00:01:39] Joe: They showed him on the sideline. Well, ’cause he [00:01:40] OG: was in the ad. They have to put all that together. [00:01:43] Joe: They gotta do all, all the stuff. [00:01:44] OG: Contractually obligated. Screen time. [00:01:47] Joe: How much do you think do, do you think State Farm paid, uh, John Bon Jovi more or us more when we were advisors? Probably us. [00:01:54] OG: It was the other way around. [00:01:55] OG: Bon Jovi paid safe. [00:01:57] Joe: He, John Biden. Show me. Hey, I really wanna be in your head. Can I, can I, can I get it on that? It is stuff to wonder here, uh, 10 days after the Super Bowl. Much better than wondering about that game. Not that it was exciting for about three minutes. [00:02:13] OG: I thought that was a great game. Yeah. [00:02:14] Doug: Well, [00:02:15] OG: defensive battle. I liked it. [00:02:17] Doug: I think real like people who are hardcore football fans, they appreciate that, but the casual observer, you wanna see all [00:02:23] OG: that. You want it to be like 68, 67 with a game winning safety. I know [00:02:31] Joe: people are like, Hey, why are you bringing up a thing that happened 10 days ago? [00:02:34] Joe: Well, because. One of the big points we’re gonna make today in the second half of today’s show, we’re gonna talk about the meltdown that happened in precious metals in crypto a few weeks ago. I like waiting a little bit to see, you know, how’s the dust gonna settle before we kind of do the play by play? [00:02:49] Joe: So we’re gonna dive into that later on. But first. And for all of you, and this is most people now, now that, um, Texas has 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. [00:03:17] Joe: They just dive in deep every year and uh, 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 wanna use this one. If you have student loans, you wanna use a different one. If you maybe can free file, there’s a third one you might wanna use. [00:03:37] Joe: We’ll go over what they looked at in all of their research. So just an action packed show today, og. [00:03:45] OG: Can’t we? [00:03:46] Joe: Yeah, we are gonna get on with it, but first we got a couple of sponsors who help us keep on keeping on you. Pay nothing for this goodness. In fact, Doug Stack a Benjamin Show always free worth every penny. [00:03:59] Joe: We’re going to more, more of that coming up. You’re killing me. So we’re gonna 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 tax options for you when it comes to the stuff you use to prep your taxes. [00:04:22] Joe: We’re gonna dive into all things tech software with him in just a moment. [00:04:34] Joe: And we’re super happy. He’s back in the basement. Robert Farrington joins us. How are you man? [00:04:38] Robert: I’m doing well. How are you? Doing [00:04:40] Joe: well. 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. [00:04:57] Joe: I, I can’t even imagine the work that goes into this every stinking year. Robert, [00:05:01] 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? [00:05:11] Joe: I feel like for this, you guys are like our version of Consumer Reports, like consumer reports on best software. [00:05:18] Robert: You’re not gonna find me installing a dishwasher in my family room to try it, but I’ll, I’ll test the tech software out. Let’s do it. [00:05:25] Joe: If it’s a financial thing, maybe 5 29 plans, you’ll do that, but not dishwashers. Let’s start here, because last year there was a overthrow of the king or the queen. We had one winner year after year after year. [00:05:41] Joe: That was best over 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 taxes as well. [00:06:05] Robert: Yeah. Free tax. USA is is where it’s at. It’s our overall pick for the best tech 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 curve ball. If you live in one of the 37 plus states that require a state tax return, it’s not free. [00:06:27] Robert: Most [00:06:27] Joe: states. [00:06:28] Robert: Yeah. But for you, lucky Floridians and Texans like it is free. ’cause you don’t have a state tax return. [00:06:35] Joe: It is funny, free tax, USA asterisk, but even without the asterisk, what is it about free tax USA that overall just makes it the, the grand champion [00:06:45] Robert: 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. [00:06:55] Robert: Filing a W2, entering a few 10 90 nines. 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 pick. [00:07:15] Joe: 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. [00:07:23] Joe: That’s it. That doesn’t mean it’s necessarily right for you, Robert. [00:07:27] 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 in 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. [00:07:52] Robert: So there are more options out there if you have some other situations you wanna think about. [00:07:57] Joe: We’re gonna 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. [00:08:11] Joe: More the same. You know, [00:08:13] Robert: 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 wanna say they started with 30 or 40 physical branches this year. [00:08:33] Robert: 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 ’cause I have not seen it yet. But, uh, you know, they are going all in on this multi-channel where you can start online and if you hit a road bump, you can call, you can get virtual support. [00:08:51] Robert: 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 brands. [00:09:01] Joe: But you’ve talked about that before. Ai, especially when it comes to doing your taxes, could be a big mistake. [00:09:07] Robert: Huge mistake, because it just gets so much wrong in personal finances. [00:09:11] Robert: One thing that AI 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 mess. [00:09:25] Joe: But speaking of HR Block, that is your second overall runner up. [00:09:29] Robert: Again, they have the great multi funnel experience, so they’ve done this for years now. [00:09:33] Robert: 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, turbot taxation, are 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 need. [00:09:58] Joe: Does HR Block still have the big hangup that you guys had in the past, which is that? You really aren’t sure how much you’re gonna pay them until you go all the way down the rabbit hole, or did they fix that loop? [00:10:09] Robert: Both TurboTax and h and R Block have gotten a lot more transparent in their pricing. [00:10:14] Robert: 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. [00:10:34] Robert: So going back to our overall pick, you don’t have that with a, uh, free tax, USA, it is all free federally. So that’s a very nice thing [00:10:42] Joe: you’re saying with these runner ups though, the problem might not be them, it might actually be you. [00:10:47] Robert: It might be you just ’cause 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, right. [00:11:02] Joe: We’re skimming the surface here, stackers. I’m gonna link to the full deep dive in our show notes at Stacking Benjamins dot com so you can go right to the college investor and get the best software because you’re definitely gonna wanna 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 text USA. [00:11:20] Joe: It’s got free in the title, so duh. This is gonna be the winner in free filing, but it’s not. It’s not the winner. If you’re somebody that can free file. [00:11:29] Robert: You nailed 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 state. [00:11:40] Robert: Ah, so truly you qualify is [00:11:41] Joe: free. [00:11:42] Robert: You got it. If you qualify to use it, it is truly free. And when I say qualify, I just mean that you don’t have unique tax 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. [00:12:05] Robert: And this happens in a lot of places. So, uh, 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 K one, different things like that where it doesn’t work for you as well. So it’s not all end all be all for everybody. [00:12:22] Robert: There are limitations and so that’s why we put it in this category of free tax software. I mean, it is free for those that can use it and it’s a great tool. [00:12:30] Joe: Some of these uh, 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 audited? [00:12:40] Robert: Yeah. So that means if you get a, a letter from the IRS and you need assistance with that letter, they will have, uh, tax professionals and attorneys there that can help you respond to those letters. Sweet. Uh, provide that response to ’em. I know getting a letter from the IRS can be scary and, uh, that’s what that upsell is for. [00:12:58] Joe: They’re owned by Square. Square isn’t a company that’s known for losing money. How do they make money if they’re doing all this stuff for free, Robert? [00:13:06] 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. [00:13:22] Robert: Now you can link your own bank account when you do this tax return that 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 it. [00:13:35] Joe: I would imagine they make it really easy for you. [00:13:37] Robert: Yes, they definitely do. [00:13:39] Joe: Speaking of your runner up is another free filing that really wants you to use their stuff too. [00:13:46] Robert: Yeah, so Chime is, I don’t know, cash App’s, one of their top competitors online. And last year, year, this is this, by the [00:13:53] Joe: way. I don’t remember. Chime. [00:13:54] Robert: You’re completely right. So last year was their first year. [00:13:57] Robert: Oh. And we didn’t put ’em on the list last year ’cause 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. Uh, if you use chime banking or curious about it. It’s so similar to what you get with Cash App, it’s still very robust. [00:14:17] Robert: You can do a lot of things. It has some uploads. You can upload your W2, your 10 99, 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 choice. [00:14:33] Joe: It’s interesting. [00:14:34] Joe: 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’s not an endorsement of Chime. But just from afar, Robert, it just seems like that company just does a lot of cool stuff. [00:14:51] Robert: Yeah, I’ve seen that too. And uh, 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 ’em about two or three years to break, sort out all the kinks and Chime came out of the gate. [00:15:10] Robert: With a really great product and not very many issues at all that I saw. And this year another great product. So [00:15:16] Joe: it’s, it, it, it is funny. I’m laughing by the way, not because it’s funny ’cause if you were on that train it wasn’t good. It was not funny. Laughing. ’cause you can’t cry. Uh, well, I guess I could cry. [00:15:26] Joe: Uh, let’s go to student loan. For student loan borrowers. Your winner here is Tax layer. [00:15:32] Robert: Tax layer. I’m putting ’em up to like the number three biggest player in the space now. It used to be TurboTax, h and r Block and like Tax Act, but tax ACT’s kind of fallen off and Tax Layer has just consistently improved their product year after year after year. [00:15:46] Robert: And what I love about Tax Layer is they have a classic tier and it has everything you could ever want. 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 HR block, well you should just choose Tax Slayer ’cause you’re gonna get all the same stuff. [00:16:07] Robert: A great experience for a little bit less money. [00:16:10] Joe: It’s interesting. Last year Eric joined us and, uh, was really, I mean, he talked so lovingly about tax layer. I was surprised that it wasn’t your pick overall. Like it’s that close. [00:16:21] Robert: They are just building a great tool out there. It’s just, it’s very hard to pass up free. [00:16:26] Robert: Like I, it’s, yeah, I just can’t do, I can’t give up free yet. I’m sorry. [00:16:30] Joe: 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? They, it just, it doesn’t make sense. [00:16:39] Robert: It doesn’t make sense. But they have a great product. So at their classic tier for like $22. [00:16:45] Robert: So it’s a little bit more, but it includes all the forms and tax layer’s. Business model is that you actually only upsell for support. Uh, 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 it. [00:17:01] Joe: And again, most of us don’t know if we need it until we. [00:17:05] Joe: We need it. [00:17:05] Robert: Sure. [00:17:06] Joe: HR Block number two. We talked about HR Block earlier. Cash app is here too. Why do you like Cash App? Specifically for people with student loans? [00:17:14] Robert: 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. [00:17:29] Robert: 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 taxes is a great choice If you don’t have anything complicated to add into the situation. [00:17:46] Joe: Our goal here is to stack a hundred dollars 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 gorilla. Still, [00:17:56] Robert: 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. [00:18:05] Robert: 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 Wall Street Bets 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 it. [00:18:28] Joe: You and I have had a conversation before and we did a Friday FinTech, uh, 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. Mm-hmm. [00:18:48] Joe: Starting to push. Are we gonna see in future years that hooking your stuff up to these third party tech software programs become more of a bear than they are today? [00:18:59] Robert: I don’t know, but I do worry that it’s gonna become more expensive. I can’t imagine that they’re gonna take the offering away, but, uh, building that out for consumers costs money. [00:19:08] Robert: 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, an account, and if you start connecting 10 accounts, it’s like 50 cents a month per user, times a million users. [00:19:24] Robert: It really starts adding up, scale up. [00:19:26] Joe: Holy crap. [00:19:27] Robert: 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 gonna load you with ads and upsells and other things, or they have to charge you because all these banks are charging them for that access. [00:19:44] Joe: It doesn’t surprise me. Then if the bajillion pound gorilla into it is your first choice with TurboTax for investors, well then certainly another company with a ton of infrastructure and one that’s been around for every h and r blocks the runner up that seems to. That just makes sense to me. [00:20:01] Robert: Yep. Same deal. [00:20:02] Robert: 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, uh, you know, 10 99 B 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. [00:20:19] Robert: These tools are really handy though when you’re trying to have an 89 49 with like line after line after line of trades that need to be reported. [00:20:27] Joe: Crypto can be a bear, especially if you’re buying it a little bit at a time. ’cause you’re buying, you know, one, 100th of a, of, of a coin. Um, for our crypto fans out there, where should they go to get their taxes done? [00:20:40] Robert: It’s the same 100 pound gorilla. It’s, uh, 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, 89 49. So if you have a bunch of Defi transactions that are just there, you can export ’em to a spreadsheet and create the tax forms you need. [00:21:01] Robert: 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 10 99 da, the digital asset, 10 99. So if you do have any trades on a centralized exchange, you’re gonna get that tax form and the IRS is now gonna start correlating those things. So make sure you’re reporting that stuff accurately. [00:21:24] Joe: It seems like five years later than it should have been. [00:21:27] Robert: You know, it’s also, I find it very messy. I think a lot of those 10 99 das 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 market as a transfer, it’s gonna show up on your 10 99 as a full gross proceed sale. [00:21:49] Robert: Oh. 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 off-ramps. Sure. 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. [00:22:06] Robert: 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 gonna get reported and you’re gonna have a tax headache. [00:22:16] Joe: 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. [00:22:20] Joe: 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 there. [00:22:29] Robert: Joe’s a crypto bull. I didn’t realize it. Decentralized currencies. Yay. [00:22:34] Joe: We just do so many stories about people getting ripped off in crypto. [00:22:38] Robert: It is, and it, 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 things. So, [00:22:47] Joe: got it. And then I imagine then I load it in just to make the trade and they go, oh yeah, this, this is found money. So it’s all, oh my goodness. [00:22:54] Robert: Yep. [00:22:54] Joe: If you’re a landlord. If you’re a landlord, what are we using? [00:22:58] Robert: I love Tax layer. You know, we’ve tried some different picks here in the past, but tax layer again, because you get that classic tier at 22.99, 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. [00:23:15] Robert: 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 tax layer is a great choice for landlords. [00:23:25] Joe: I remember last year Eric telling us, Robert, that this is really where Tax Slayer shines. [00:23:30] Robert: 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 price. [00:23:39] Joe: 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 using? [00:23:49] Robert: 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. [00:24:03] Robert: But if you do need a little bit more, if you need to build out like, uh, the, the full Schedule C and you have a lot of stuff that you wanna 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 HR Block, you’re suddenly in the self-employed highest tier, you know you’re gonna be paying a hundred dollars plus for your taxes. [00:24:28] Robert: You don’t really need to pay that much. [00:24:30] Joe: A lot of people when they first start a side hustle, they forget, right? That I gotta keep track of this stuff throughout the year, and then they’re sitting there with markers that are four different colors. This. To make it up with what their mileage. I’m not advocating this, I’m just telling you what I’ve seen people do. [00:24:47] Joe: All right. [00:24:47] Robert: Yeah. [00:24:47] Joe: It’s ugly when you start your side hustle. Some people, you know, they finally figured out that they should use QuickBooks Zero 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. [00:25:07] Joe: What do you guys use? [00:25:09] Robert: 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 a spreadsheet. It makes it so much [00:25:17] Joe: easier. [00:25:18] Robert: 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. [00:25:25] Robert: 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, uh, 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. [00:25:44] Robert: So they’ll say like, I made $1,200 driving for Uber last year. But then you’re paying taxes on the full $1,200, 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 $1,200. You probably profited half that or less. [00:26:04] Joe: Yeah, [00:26:04] Robert: after your expenses. And you don’t wanna be paying more taxes than you legally have to. [00:26:09] Joe: 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. [00:26:21] Joe: 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. [00:26:40] Joe: Who’s your winner there? [00:26:42] Robert: 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, um, 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, they’re small business. [00:27:04] Robert: Tier, which is a, a support tier. ’cause 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 do. [00:27:18] Joe: 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 at? [00:27:26] Robert: 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. [00:27:44] Robert: It is not gonna help you save money on your tax, soft 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 happens. [00:28:11] Joe: 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 gonna do all year long. And of course, as you can imagine, Robert, that’s a bunch more expensive. [00:28:27] Joe: But I also have to tell you that when January hits, it’s done. It is, it is done. I filed my taxes so early every year because the fact I have that person in my corner. But, uh, I’m so glad we have you in our corner. And 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. [00:28:54] Joe: 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. [00:29:11] Joe: Great job as always. [00:29:13] Robert: 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, uh, making, uh, Bob Vance from the office is our mock tax return. Every year we start making Vance refrigeration, uh, tax returns. [00:29:34] Joe: That’s fabulous. Bob gets a workout. [00:29:36] Robert: Yeah, he does. He files a lot of tax returns every year. I hope the IRS doesn’t catch on. [00:29:41] Joe: We’ll link to the piece at uh, stacky Benjamins dot com or you can go directly to the college investor.com this time of year. Robert always has it right on the front page. You’ve got a, the website right there that you could just clink through. [00:29:51] Robert: Thanks so much. [00:29:52] Joe: Clink through. [00:29:53] Robert: Clink [00:29:53] Joe: 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 it. [00:30:01] Robert: Definitely. Thanks for having me. [00:30:04] opener: I am Rocky Ani, the Profit Answer man. And when I’m not helping small businesses stack Benjamins for themselves, I’m Stacking Benjamins for myself. [00:30:18] Doug: 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. They’d be like just an eight. Oh, they, they got thumbs too? Uh uh. All right. Maybe I’d be a, like a raccoon or something. [00:30:37] Joe: Well, [00:30:38] Doug: 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 up some doors for me. Pause for laughter. Today’s also the birthday of Queen Mary, the first who lived from 1516 to 1558 just to. Few short years before Joe. [00:31:02] Doug: No. Mary shares an unfortunate nickname with a drink. Lots of bars, restaurants, and brunch. Love and 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. [00:31:32] Doug: 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. [00:31:59] Doug: It seems unlikely we’d 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 glass. Geez. And now two guys who share a name with one of America’s founders, maybe a little more savory, Joe and og. [00:32:29] Joe: That is quite the story. When you look up where the name of the drink came from, like I don’t, no, no. [00:32:36] Doug: You wouldn’t drink so many of them. [00:32:37] Joe: No, no. We want nothing to do with that. By the way, you asked the question, Doug, who was the queen right after Mary died. It was Queen Elizabeth the first we were talking about on our trivia just recently. [00:32:52] Robert: That’s right. [00:32:52] Joe: Now you know the rest of the story. [00:32:54] Doug: The rest of the story. [00:32:56] Joe: 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 passed. [00:33:12] Joe: And so big thanks to them for doing it. ’cause man, we didn’t wanna do that research. They seriously dive in. Let’s, uh, speaking of dive in, let’s dive into a headline. [00:33:22] headlines: Hello Doling. And now it’s time for your favor. Part of the show our was Stacking Benjamin’s headlines. [00:33:29] Joe: Well, uh, a couple weeks ago we had a big old meltdown. [00:33:33] Joe: In the precious metals markets as we saw silver lead the way, and then gold, and then of course crypto as well drop tumultuous gold saw its biggest daily drop since the early 1980s. Silver went out 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. [00:33:58] Joe: After President Trump selected Kevin Walsh as the next Federal Reserve chair. The nomination appeared to ease concerns about the central bank’s independence, given war’s, historically hawkish stance when you read about quote, what the market thought, og, which always makes me laugh ’cause the market never thinks one thing. [00:34:17] Joe: But all of the news organizations talking about the market liked the fact that wars seems to be a good pick for our next, uh, 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 crypto? [00:34:49] OG: No, no insight whatsoever because ultimately. Prices of things that don’t produce any value are gonna 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. [00:35:17] OG: I’d love to have len’s take on this. Because I know he’s been a silver guy for about that. He’s [00:35:22] Joe: finally, finally, with [00:35:23] OG: winning 72 years, he’s like, I told you guys like, okay, I think this is true for any asset class that you catch wind of and and find out the results of in the back end. And what I mean by that is you go like, whoa, GameStop’s up 3000%. [00:35:42] OG: 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 like 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 and going like, well, I need silver as a diversifier. [00:36:08] OG: It’s just completely lying to yourself as to what you want to have it for, because you’re just going, you just see the price. 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. [00:36:29] OG: 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, 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 mean? [00:36:43] OG: A certain amount of fomo. Why do I wanna own it? Well, because it looks like it’s, you know, whatever. Same thing with Bitcoin, same thing with, you know, silver. And even with the volatility, I think, I think the volatility’s one story, which is, you know, what did it go from 115 an ounce on silver down to like 75 in a nanosecond? [00:37:02] OG: 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 silver [00:37:14] Joe: a leveraged bet. [00:37:16] OG: He put $200 million on a bet that silver was gonna go down roughly 12 hours before it went down 30%. [00:37:27] OG: Eh, I don’t know. Does that ask the sniff test? No, it does not. [00:37:35] Joe: Might be a little market manipulation going on there, you think? Or, or just somebody who might know a little something, something about who the next Fed chair would be. Or [00:37:42] OG: it’s like the guy who made a $50,000 bet on poly markets that Maduro was gonna be arrested sometime this month, like literally three hours before he got arrested. [00:37:53] Joe: So weird. [00:37:53] OG: Listen, I’m all for, if that was like an Air Force pilot or a Delta guy, I’m the helicopter going, guys, you wanna 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 anywhere here a a little [00:38:08] Joe: overtime pay a little overtime. [00:38:10] OG: Yeah, a little something for the effort. You know, as they say. I’m good with that. Some Wall Street dude that’s friends of a friend, you know, that can borrow $200 million against his 30 million. You know, 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 one asset class is. [00:38:33] OG: 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. [00:38:56] OG: 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 gonna be wildly all over the place. [00:39:17] OG: 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 gonna get a wild ride one way or [00:39:25] Joe: the other. 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. [00:39:36] Joe: The probability is gonna swing much, much more just going tech stocks versus mid cap stocks. But then if I just say Nvidia. It’s gonna be even wider. Like who knows what new news NVIDIA’s gonna 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? [00:39:57] Joe: We can cut ’em off at the knees. We don’t have any idea. Uh, strategists said, gold and silver’s epic rally was due for a pullback. The higher medals rise, the more likely 2026 will mark enduring price peaks, notably for silver if history is a guide. Mike Magone, senior commodity strategist at Bloomberg wrote, and then he said, there are always sound fundamental reasons for rallies, but when prices rises rapidly as they have metals, deficits can shift fast. [00:40:24] Joe: 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 reality. [00:40:31] OG: 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 gonna spring in the other direction. [00:40:41] OG: It’s a good analogy for when things don’t go well. You know, think about COVID VID 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, like that’s kind of a knee jerk reaction, and then we’ll find where it should be after more data comes out. [00:41:10] OG: You know, I think it’s true for, like I said, any asset class that you narrow your focus into, you’re gonna start seeing increased volatility if you just pay attention to that asset class. [00:41:22] Joe: With the relative long term. Calming feature that gold can have on a portfolio. Stacker Dave in [00:41:30] OG: the, that’s, that’s a funny way of putting it. [00:41:32] OG: Doesn’t do anything for 30 years, but go ahead, [00:41:34] Joe: stacker Dave in the basement Facebook group asked the question, which is, people see these. Long time sits and they go, Hey, uh, 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. [00:41:51] Joe: In fact, I, uh, had it, uh, put up in front of me that I’ve quoted, uh, long time financial writer Walter up grave is saying it’s eight times more volatile. That is a true quote. Walter up Grape did say that I’ve quoted Walter before, but even without this time, we will see on a daily basis, three four x. I don’t know if it’s eight. [00:42:11] Joe: I haven’t taken the time to look at what is generally zero to 5% of any average portfolio to look into it, but you don’t want, imagine if somebody at gold is their emergency fund. 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. [00:42:34] Joe: 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. [00:42:55] Joe: 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 days. [00:43:10] TikTok: 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%. [00:43:37] TikTok: 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. [00:44:00] TikTok: Leverage 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 engineered and now, [00:44:18] Joe: and he goes on with this og and [00:44:20] OG: it sounds like so much ai. [00:44:22] OG: I don’t, I don’t know that. I mean, do you have like a check mark next to that guy’s name to know that it really was Peter Lynch? [00:44:29] Joe: 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. [00:44:45] Joe: And then I clicked on this guy who is 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. [00:45:02] OG: Okay? [00:45:03] Joe: This is a hundred percent. I [00:45:04] OG: would say my BS detection went really high, like he started, wow. [00:45:07] OG: Like the timing on it was a little off, [00:45:09] Joe: but what’s amazing about that OG is I believe that’s because you do this every day. And you’re like, well, I, I don’t know. [00:45:18] OG: Plus, wouldn’t Peter Lynch like seriously be like 90 something right now? [00:45:21] Joe: I know the average person is gonna see this and just go, oh yeah, this looks like Peter Lynch in his prime, by the way. [00:45:29] OG: Yeah. [00:45:29] Joe: Looks like the old Peter Lynch. But it is so frustrating that something like this happens. And when’s the time when you’re gonna make a mistake, guys? You’re gonna make a mistake when all of a sudden stuff’s being pulled out all around you, and you’re gonna start. Going to places like this finance, the finance guy, and his Peter Lynch video. [00:45:50] Joe: And, uh, 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 ugly. [00:46:04] OG: Yeah. So all of that, the, there’s no JP Morgan short position, CME margin, blah, blah, blah, blah, blah, blah, blah, blah. [00:46:11] Joe: Smoke meet mirrors. Dogs. Meat ponies. Ugly, ugly uglies. I mean, [00:46:17] OG: that’s not to say that some of that’s not true. I mean, maybe JP Morgan did close a short position [00:46:22] Joe: a hundred percent. [00:46:23] OG: Maybe they, [00:46:23] Joe: yeah, [00:46:23] OG: whatever. Who [00:46:24] Joe: knows what, what’s the best lie you can tell, right? The best lie you can tell is one that’s 97% true. [00:46:29] Joe: And it’s that 3%. [00:46:31] OG: Oh God, yeah. We are so screwed. [00:46:33] Joe: Yep. People taking advantage of people not knowing any better. Watch out for AI people. It’s ugly. All right. Uh, I will link to this and show notes. [00:46:41] OG: By the way, I don’t do a lot of social, as you guys know, but when I see that stuff I file, I I, I do like the like complain button [00:46:49] Joe: every time. [00:46:50] OG: Every time. Not 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 just little thing. Andthen
[00:47:02] OG: you know [00:47:03] Joe: what’s frustrating OG Then the powers that be do exactly with this video. [00:47:08] Joe: What they do with our show when there’s an AI show, spoofing our show right now. You know what they do? Nothing. [00:47:13] OG: Not our problem. [00:47:15] Joe: Nothing. [00:47:15] OG: We love the cliques. [00:47:17] Joe: Even though, even though Spotify and Apple, it says right on your stuff that if it’s AI generated you, you’re getting the boot show us boot, this AI show calling itself Stacking Benjamins. [00:47:30] Joe: It’s incredible. Anyway, not that I have an ax to grind on this topic. [00:47:34] OG: No, it’s, it’s legit. [00:47:36] Joe: It is legit. It’s, it’s so frustrating. We’ll link to this in our show notes at stack of Benjamins dot com and I’ll also link to that video so you can see. [00:47:44] OG: Can you imagine if one day. Somebody sends us a letter and says, I was really surprised to learn that you guys, uh. [00:47:50] OG: Decided to go all in on whatever, [00:47:53] Joe: horrified, [00:47:54] OG: and then 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. [00:48:07] OG: Or like whatever. [00:48:07] Joe: Yeah. [00:48:08] OG: Right. [00:48:08] Joe: Oh, don’t, [00:48:09] OG: that kinda happened to Paula a little bit, right? It [00:48:11] Joe: did. Did she have, she gets spoofed on, she’s been spoofed on social media two or three times. [00:48:15] OG: 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. [00:48:22] OG: So maybe we should say that very publicly. We will never do that. We will never ask you to invest in a, uh, venture that we’re doing together. That’s not a thing that we will do or have done. [00:48:35] Doug: We really almost never give specific investment advice on a spec. You know, I mean, commodity, it’s [00:48:42] OG: short, silver. [00:48:43] Joe: I mean, [00:48:44] OG: obviously that’s, [00:48:46] Joe: you wonder who the guy was that that leveraged that bet the day before. [00:48:51] OG: 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 a, do you think that’s, [00:49:03] Joe: they called it. [00:49:04] OG: He had gone from a hundred down to 30 was like, this is my final hurrah. [00:49:07] Joe: Yeah. Either way your money’s not gonna matter, right? [00:49:09] OG: Or is this a slush fund of like 30 mil that has left over? Like, yeah, I mean, let’s short, you know what? I got an idea. Let’s borrow seven x and uh, short 200 million against our 30. I think it’s gonna go down tomorrow. Oh, wink, wink, wink. [00:49:22] Joe: Bam. Couldn’t have called it better. Doug, let’s wander out on the back porch ’cause we’ve got a couple things here. [00:49:30] Joe: Please join me if you’re around Omaha on Friday, Omaha 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 Benjamins dot com slash meetup to come join us and two weeks later, I’ll be in Seattle with our Benjamin’s after Dart group hanging out at Capitol Hill, Elysian Brewing. [00:49:56] Joe: That starts at six 30. Uh, that is going to be on March. Let me get the date. That’ll be March, uh, fifth that I will be there. So come join me and all your Seattle stacker friends from the Bad Meetup group. [00:50:09] Doug: Will you be drinking Dunkin Coffee while you’re there, Joe? [00:50:12] Joe: Well, the, it appears that since Seattle won that the Boston group is going to have to have Starbucks. [00:50:21] Doug: Oh, is that the way it worked? Okay. [00:50:23] Joe: 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 Dunkin coffee, of course, big Boston brand, and then. The opposite. So Boston, their first meetup coming up March 11th, they’re going to be, um, having to hold up at their very first meeting. [00:50:45] Joe: Everybody’s gonna have some Starbucks as, uh, the Seahawks brought it home. But anyway, for all of our meetup groups around the country, stacky Benjamins dot com slash bd for Benjamins after dark. For more on my stops in both Seattle and in Omaha, uh, Stacking Benjamins dot com slash. Meetup. A couple other things. [00:51:06] Joe: By the way, we’re gonna be doing a live show more on this coming up next week. Live show in Texarkana. What, how about that? Does that, is that wild? [00:51:15] Doug: Wow. [00:51:15] Joe: It’s, it’s incredible. We’ll be at Texas a and m, a joint project with Texas a and m in front of, uh, students and community members. So if you’re anywhere close to our hometown of Texarkana, come see us and our amazing special guest. [00:51:29] Joe: 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 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 country. [00:51:49] Doug: It’s happening. [00:51:50] Joe: It is happening. It’s roll it 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 friend. [00:52:02] Doug: Well, Joe first take some advice from our tax software segment. [00:52:06] Doug: 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 gonna become a famous bartender, you need to have a drink named after you. All I can come up with is Doug’s dump truck. [00:52:29] Doug: I need some help stackers. Let’s hear what you got on Facebook. Doug’s dump truck. I mean, he’s got a ring to it. Right. [00:52:38] Joe: That sounds like a hangover. Like I am gonna have the biggest hangover. [00:52:43] Doug: Oh, I’ve got a dump truck on me. Thanks. Thanks to Robert Farrington from the College Investor for joining us today. [00:52:50] Doug: You’ll find the entire guide to tax software@thecollegeinvestor.com. We’ll also include links in our show notes at Stacking Benjamins dot com. This show is the Property of SP podcast LLC, copyright 2026, and is created by Joe Saul-Sehy. You’ll find out about our awesome team at Stacking Benjamins dot com. [00:53:12] Doug: Along with the show notes and how you can find us on YouTube and all the usual 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. [00:53:34] Doug: I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time. Back here at the Stacking Benjamin Show. [00:54:33] Joe: It’s time for a quick roll call. As many of these as we can do in two minutes. How about that? [00:54:41] Doug: On my reviews of things I’ve watched recently. [00:54:43] Joe: Yes, because you’ve watched a lot of stuff. [00:54:46] Doug: I have. [00:54:46] Joe: So [00:54:47] Doug: whenever I put these lists together, I start to get worried about myself. Like, God, I need to pick up a book. [00:54:52] Joe: You do or you need a friend? [00:54:54] Doug: 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. [00:55:17] Doug: So I like season two better. [00:55:19] Joe: I did hear at a party, by the way, last week about the guy that had a four hour problem. [00:55:25] Doug: Oh yeah. Right. [00:55:27] Joe: A guy with a, yeah. Which, uh, if it makes it to a party, a party she go [00:55:31] OG: to. Joe, does Cheryl know [00:55:34] 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, uh, but yes, the guy was [00:55:42] Doug: the crazy rashes that woman must have seen at parties. [00:55:45] Joe: Oh man. [00:55:46] Doug: Landman season two horrible television show. Amazing. Billy Bob Thornton monologues. [00:55:53] Joe: 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 are both shaking your head now [00:56:00] Doug: as a construct of a storyline. It’s a train wreck. It’s a complete mash pile. [00:56:07] Doug: Mosh pile. It’s like they rushed it. Plot lines [00:56:09] OG: for some reason. I don’t know what they did, but they did it bad. Yeah, [00:56:13] Joe: we got 45 seconds, Doug. [00:56:15] Doug: No bullshit because you guys, you give me these time limits and then you chime in with your own thought. Thoughts. We [00:56:20] Joe: could do the rest. I just said, how many are we gonna get through in two minutes? [00:56:24] Joe: I didn’t say we had to stop. We can do another one another time. Now we’re down to 30 seconds. ’cause you complained about it. What’s up next? Ha [00:56:31] Doug: the rip. Really fun ride. Uh, lots of good twists near the end, other than a completely implausible chase scene. Really fun movie to watch. Would recommend [00:56:42] Joe: the rip. [00:56:42] Joe: What’s the rip on [00:56:43] OG: Netflix? [00:56:45] Joe: It’s on it. Netflix. I haven’t even, I’ve, but I love the way you skip 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 minutes. [00:57:00] OG: Two minutes. Sure. Seems like a long time when Doug’s involved. [00:57:02] OG: Doesn’t it [00:57:05] 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 wear she, Doug [00:57:14] Joe: talks tax wear. Tax wear. [00:57:16] Doug: What underwear should you be? 3, 2, 1.
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