Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you’re a side hustler, crypto investor, or just looking for a free filing solution.
- Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year.
- H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to.
- Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions.
- Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table.
- Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix.
Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations.
If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Wednesday Mentor: Eric Rosenberg
Big thanks to Eric Rosenberg for joining us today. To learn more about Eric, visit Eric Rosenberg | The College Investor. See Eric’s list of the best tax preparation software for 2025 by visiting Best Tax Software 2025 [Awards And Comparisons].
Our Headline
- Stocks Have a Big, Expensive Problem (Wall Street Journal)
Doug’s Trivia
- What book was released on today’s date WAY back in 1957.
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Other Mentions
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Tune in on Friday when we’re talking places where we KNOW we’re overpaying…how do we make a better plan and save some Benjamins?
Written by: Kevin Bailey
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Episode transcript
[00:00:00] bit: At some point far in the future, historians will probably ask, what was daily life like in the early 21st century? Well, one thing we know for sure I. Nobody will ever point to these two clowns and say, this was how you should have been Stacking Benjamins [00:00:24] Doug: live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. [00:00:39] I am Joe’s mom’s neighbor. Duggan, we have a phrase here, riffing off Game of Thrones. Tax day is coming, but don’t you worry one little bit. I think I nailed that, didn’t I? But don’t you worry one little bit. I love the guy that stops the open partway through to pat himself on the back. I’m, man, I got that. [00:00:57] Me. I’ve rehearsed and I rehearsed and I rehearsed. I’m like, yes, you’re kidding. You’re so good. You’re so good. Don’t you worry, listener, because today we’re gonna dive into all the good, bad, and ugly when it comes to software programs with a man from the team that did the research. So you don’t have to. [00:01:15] From the college investor, Eric Rosenberg, in our headlines, wall Street Journal writer Spencer Jacobs says that stocks have a big expensive problem. Do we agree? We’ll share and. Help you navigate your portfolio and of course I’ll swoop in with some incredible trivia There I am patting myself in the back again. [00:01:35] That’s sure. To amaze your friends. And now here are two guys who believe the only thing better than a good laugh is a better bank account. It’s Joe and Oh cha cha. [00:01:51] Joe: I love that when the bank account stops him from laughing, like, oh hey. Oh, wait a minute. Hold on. Hey everybody, welcome to uh, eight digits in the bank account for the WIN podcast. I’m Joe Sal. See, hi. Wait a minute. [00:02:04] OG: Little light of that. Yeah, that would be good. Does that include the decimal point? [00:02:08] Joe: A decimal point in six places behind it? [00:02:11] OG: Still pretty good, honestly. [00:02:14] Joe: Hey, 10 bucks. It’s 10 bucks, right? Oh, we get a great show today. In fact, last year one of our top rated videos over on our YouTube page was this interview a year ago where we dive into the college investor. [00:02:28] OG: We’re playing it for you here again today. Yes. And see, [00:02:32] Joe: we’re just gonna hit, just play that again. [00:02:35] Uh, every year, the college investor team, they dive into all the tax softwares that are available, and this gets to be og more of a heat of battle every year for. Countless years. It’s been, Hey, just do TurboTax. Just, just do TurboTax. So does TurboTax hang onto the Crown last year? Not so [00:02:51] OG: fast, my friend. [00:02:53] Joe: Maybe, maybe not. Last year, Robert Farrington was here and they said TurboTax was their most recommended, but some of these other software programs every year closing that gap. So what’s your best choice? We’re gonna dive into that today, but first, let’s meet the team. Og, how are you doing on this fine Wednesday? [00:03:10] OG: Just happy to be here. [00:03:12] Joe: And I, we had high winds recently, and you took a nice video of all the stuff that was under, under your rooftop, no longer under your rooftop. Like you had a bunch of, including my [00:03:24] OG: rooftop. [00:03:25] Joe: Yeah, your, your backyard was, uh, was a little messed up. How, how high did the winds get by you? [00:03:31] OG: Well, I have a weather station, but the power went out, so based on my weather station, 14 miles an hour, but I think it was a little higher than that, I think. No, the, um, by the kids’ school, there’s a small little airport right next to it and they measured 82 of a wind gust. It flipped a bunch of airplanes over, but, um, um, we have to go swimming. [00:03:49] I got to go swimming. It, uh, was not, the pool was not warm enough to go swimming, but uh, people tell me cold plunges are good things, so I cold plunged myself into the pool to get all my stuff out. Just [00:04:01] Joe: to get all your stuff out of the pool. Yeah, [00:04:04] OG: it was awesome. Thankfully my son helped and, uh, he’s a little bit of an engineer, so he was like, hold on, dad, before you slow down Marine before we just, you know, go charging into battle. [00:04:15] Why don’t we make a plan first? And I’m like, plan is get stuff out of pool. I eat crayon. And he’s like, hold on, I think we might be able to fashion a, a, a, a way to get some of this out without having to get wet first. And I’m like, okay, cool. So he fashioned a little, uh, grappling hook type device and uh, we dragged a bunch of stuff outta the pool without having to get wet. [00:04:35] So that was nice too. But then you just went in for fun [00:04:38] Joe: at the end to get the gold plunge. I, I didn’t [00:04:40] OG: know. That’s not my favorite. I, I don’t know how people do that. I try it in 60 degree water and I’m like, this is awful. I, I don’t know who in their right mind would do it with 40 degree. I, I don’t, it’s a health benefit, like, well what is heart attack? [00:04:53] I don’t think the point [00:04:54] Joe: of it is that it’s, wow, this is great. I love icy cold water. That’s not the point, is it? [00:05:00] OG: I mean, I think so, yeah, some health benefits of some kind. [00:05:05] Doug: It reduces your overall inflammation in your system. That’s what they say. It’s an anti-inflammation thing, which leads to lots of other stuff. [00:05:11] I’m pretty [00:05:11] OG: sure 150 rate heart rate would increase inflammation and stress and all manner of stuff. But, um, I don’t know, [00:05:20] Joe: one more thing to talk about before we get to our big stuff today, which is that, uh, big 10 tournament starting now. So I got the Sparty mug all ready to go, ready for my [00:05:31] Doug: team. Wow. Well, we’re recording this ahead of time and, uh, it hasn’t started yet and I think you have reason to be optimistic, Joe, but if last night’s beat down of Rutgers by Purdue is any indication if that Purdue team shows up. [00:05:46] Ain’t nobody beating them. They put a hundred spot on a team with two first round draft picks on Rutgers. On Rutgers. I mean, Rutgers is like Rutgers. They have two first round NBA draft picks. I mean, they have the potential to be a great team. And we put a hundred spot on ’em. Is [00:05:59] Joe: it Wow. How Rutgers athletics now in football and in basketball? [00:06:03] Just, just not the team that was there when they entered the Big 10. Thank you. Big 10 Money Bank account. [00:06:10] OG: Uh, [00:06:11] Doug: well we got a [00:06:11] OG: great show, show. We’re gonna talk, let wait. Hold on, hold on, hold on. What’s their record? [00:06:15] Doug: Oh, the record. That’s what I’m saying. Their record belies their talent and their basketball team. [00:06:19] I think they were, uh, as of last night, I think they were 14 and 15, they had a roughly five money. So they’re basically like all, there’s no change. They used to be a lot worse than that. They used to be a lot worse than that before they were in the Big 10 in both football and basketball. They got a great football question. [00:06:32] We are [00:06:32] Joe: 500 and when they started the Big 10, oh man. [00:06:35] Doug: But they have two every consensus, like every analyst says two of their guys are going first round. All right, we’ll see. So they got talent. [00:06:42] Joe: Well going first round when it comes to tech software is the college investor that’s going [00:06:47] Doug: first round in my book. [00:06:48] Oh number, no, sorry, number, number one. And I appreciate that og, but Joe’s segue was that was pro level stuff, Joe. Um, I gotta pay you your dues there. [00:06:56] Joe: Number one, when it comes to tax software is the college investor. Every year they dig into what’s the stuff you should use, what shouldn’t you use? What’s the good, bad and ugly of all of these different tax platforms? [00:07:09] How do you choose the right one? Turns out it isn’t just going with my buddy uses it. There’s a lot to know. Eric Rosenberg, his cheapest. Exactly. Eric Rosenberg’s been with that team for a long time. Eric and I go way, way back. We’ve, uh, served on not only on Plutus Foundation, but also prison chain gangs together on Plutus Foundation panels. [00:07:31] Uh, not to mention the, uh, the chain gangs. Eric wrote the majority of this piece, but man, they all, the, the whole college investor team gets involved in just a second. We’re gonna say hi to Eric and to tax softwares. But before we get there, we’ve got a couple sponsors that make sure that we can keep on keeping on. [00:07:48] You don’t pay a dime for this goodness. We’re gonna say hello to them and then we are diving into your best, your worst, your ugliest tax software. [00:08:07] And I am super happy he’s here with us getting the band back together. Eric Rosenberg from the college investors here. How are you man? [00:08:13] Eric: I am doing great. I’m happy to be here. It’s a beautiful California day, having grown up in Colorado. It’s really cold this time of year, and I’m in a t-shirt. [00:08:23] Joe: Yeah, what a flex. [00:08:24] Just super, super flex. [00:08:26] Eric: Three quarters of the people are just raising their fist, you know? But remember all of you people that it costs a lot to live here. That is true. Yes. I’m paying for it. Yeah. Cal, [00:08:35] Joe: California, the land ain’t cheap. Oh yeah. It’s the sunshine tax. Well, speaking of tax, that’s the bummer about why we’re talking to you is this tax time. [00:08:44] We’re gonna talk over the next several minutes about all the different types of filers. Uh, we’re gonna talk about people that should be doing free filing. We’re gonna talk about for entrepreneurs, people that have crypto investors, all different types of people. But let’s start off with just the overall winners. [00:09:00] You, Eric, took a deep dive like you guys at the college investor do every year. And really the difference is software. Let’s, let’s start here. Who should use software versus who should use a pro or, or are those two continuing to kind of meld together? [00:09:16] Eric: That’s a great question. So the tax software, most of them now have upgrades where you can work with a pro through the software, but you’ll of course pay extra for that. [00:09:27] In general, I’d say most people, if you’re comfortable using a computer, if you can do online banking and email and you know the basics, you could probably navigate most modern web software. If you are someone who doesn’t like computers, and I’m guessing if you’re listening to a podcast, you’re probably more comfortable with computers probably gonna be okay. [00:09:49] Yeah. Maybe if you’re talking to your grandparents or your parents, they, I don’t know how old you are and they’re, if they’re the kind of person who like can’t deal with logins and just has trouble navigating the web in general, probably still better to go, uh, with the in-person accountant. When we get into people with more complex taxes, um, as we’ll dive into some of these tax apps, most of them can handle even the most complex things. [00:10:15] Like I’m a business owner, I could use just about any tax software on this list. I can deal with mortgages, investments including crypto child tax credits, like just about anything that the average person would have all the tax software can handle. But if you have enough money and you just don’t really want to do it, you know, it’s, it’s your money. [00:10:35] You might find it just so frustrating to sit down and type your stuff in for an hour or two that it’s worth paying someone and that’s okay. You know, it’s it personal. Finance is personal. It’s up to you how you wanna spend your money. For me, I think one of these apps that’s more affordable is totally good. [00:10:50] It’s totally sufficient. And if you’re a Stacking Benjamins listener, you’re probably in tune with your money more than the average person. So you’re probably best suited to go with an online option. [00:11:01] Joe: Well, and what’s wild about these online options, Eric, you guys point out. They get better every year, but there’s a, a portion of our audience that is listening going, okay, just tell me which one’s best. [00:11:10] Like, I don’t want the preview, but, but best you guys know more than it best is in the eyes of the beholder. This is a little bit more of a fine, uh, fabric than just one size fits all. [00:11:21] Eric: Yeah. So I’d say the best is best for your style and what you need. If for you best means easiest, it might be worth paying a little bit more for something that’s a little easier for, um, college investors. [00:11:36] If you’re a younger person and you would rather save the money and you don’t mind spending a few more minutes, the best option might be a cheaper one, and that’s not quite as slick. And that’s how we actually broke down our top options this year for the first year in. As long as I’ve been doing this with the college investor, really anywhere. [00:11:53] We knocked down the 800 pound gorilla in the industry from the top spot because of that cost. But we also said it’s a good choice if you just want the easiest and kind of the best experience and don’t mind paying more for it. [00:12:08] Joe: All the years, you and I and Robert and I ha have been doing this, TurboTax has been the number one, the the granddaddy, but also the best. [00:12:18] Even though last year Robert had a bunch of consternation and problems with TurboTax that have continued. He also said that I. You guys at the college investor, really it was a knockdown drag out about which one was the best? TurboTax still on top, just overall this year. Is that the number one choice? [00:12:34] Eric: Last year I went to bat for TurboTax still. I said I think it’s the best because if you want the easiest and the slickest experience, TurboTax offers that. It has the automatic imports from most banks and investment companies. And if you’re like me and you have several investment accounts and a handful of trades here and there, you don’t want to type any of that in. [00:12:56] TurboTax does make that the easiest. But uh, to Robert’s point this year, I actually gave in to his consternation and we took them out of the number one spot because they’re not as clear and upfront on pricing. And that’s something we value, that, that’s something at college investor and anyone I work with, uh, when you go into an experience, you want to know what you’re going to pay upfront. [00:13:17] And, you know, we’re stuck with like the phone companies that you sign up and, you know, they say it’s gonna be 49 99 a month, but then there’s like $800 in fees on the end, right. Um, with, uh, tax software. It shouldn’t be that way. Well, with any product really, it shouldn’t be that way. Uh, but with tax software, and when you sign up, you might click a link that says, start here for free. [00:13:37] And then you get through all the buttons, and at the end it’s like you owe $189. Uh, we don’t like that kind of surprise. [00:13:42] Joe: So Turbo Tech still hasn’t gotten rid of that. Then they still, you, you go in, you input all your stuff, you’ve no idea what the end result is. It’s only Eric when you push the button at the end that you find out how much you’re gonna have to pay for this. [00:13:56] And now you’ve already invested a bunch of time and energy. I mean, you, you kind of feel like a prisoner, [00:14:01] Eric: right? So that’s why we have a new best overall our, our winner this year. It kind of surprised me when I started thinking through and saying, do I really want to pick someone that’s not TurboTax? Then who is that going to be for a long time, the runner up I’d say was h and r block, and I think they’re probably the second easiest if ease of use is your goal, but be based on price and quality. [00:14:23] If you want to balance out and find the best overall value, we picked free tax, USA, so a lot of you might not be as familiar with them. Um, they’re one of the big ones. The only thing that I really don’t like is that they have free in the name ’cause it’s not really free. Uh, they’re gonna charge you something, but it’s a heck of a lot less than TurboTax for the average person. [00:14:43] The only person who will be able to truly use free tax USA for free is someone who doesn’t have a state return. Right. That’ll be me in Texas. Right. Lucky you. No state income tax down there. But they get you somehow, you know the property taxes and sales taxes. Right. They get us all somehow. [00:15:00] Joe: Yeah. But you guys wrote, you can upgrade to get technical support with the app for $8 7 99. [00:15:05] Right. And support from a tax professional at $40 39.99. [00:15:09] Eric: Yeah. And if you do that through. Something like TurboTax or h and r Block or Tax Act, there are three of the big incumbents in the industry. You’re gonna pay a lot more typically to get individual support. And even if you don’t need that support, if you’re just comparing apples to apples, let’s say you have kind of typical taxes of, uh, someone who has maybe a bank account interest and an investment account, and, uh, a kid or two, maybe a house. [00:15:37] What you’ll pay with free taxi USA is just so much less, and unless you are an ultra active trader. Who has lots and lots and lots of line items to type in, uh, which most of us are not, uh, most of us shouldn’t be. But unless you have a ton of tax forms and a ton of trades, the time difference isn’t gonna be that significant. [00:15:58] And with any tax software, your result should be the same at the end. When they’re using the same math, the same calculations, they all have a maximum refund guarantee because they give you the refund you’re supposed to have. That is the maximum refund. If you have an accurate refund, that is your maximum refund. [00:16:13] That [00:16:13] Joe: is [00:16:14] Eric: the maximum. So it doesn’t matter which one you use, it’s how much time you’re going to have to put in, how much effort you’re going to have to put in and what it costs. And for my 2 cents, I’d rather pay a lot less. Uh, so that’s why we picked free Tax USA this year. The company owns multiple brands. [00:16:29] I think Tax Hawk is one of them. I forgot what the other is. They actually use the exact same software and pricing on all of their brands, but, uh, free tax USA feels easier to remember, but it’s a good choice if you have relatively straightforward taxes and you want to do it the cheapest way possible, we’ll still paying for a more premium service. [00:16:49] That’s, uh, that’s our top pick. [00:16:51] Joe: Yeah. You write that it doesn’t include the option to import tax data from banks and brokerage firms. You must manually type in tax form details. It’s still easy to use, very good for the cost. It sounds like, uh, when it comes to TurboTax, the number two pick, Eric, that really is the difference is that all that stuff can be imported. [00:17:08] So back to what you said originally, TurboTax second because of the slickness of what you get. I, I’m assuming [00:17:14] Eric: there’s so many upsells throughout. And I actually sat down with a family member who had always taken her taxes to an accountant and said, I wanna do ’em myself. I wanna use TurboTax. ’cause it’s the big one. [00:17:24] I said, great. And at the end when the bill popped, it’s like, I didn’t think I paid. We’d have to pay this. I didn’t think I checked this. There’s just so many upsells and easy ways to say, oh, I’ll pay extra for support that you might not actually need. Or she didn’t realize she was clicking to upgrade for paid support, but she did. [00:17:41] Oh, no. Um, so then when it came time to pay, they’re like, you ordered paid support and she never used it. If she got tricked and she’s not a dumb person, um, it’s easy to make that mistake. That’s really the big drawback, uh, is pricing transparency and it just costs more. But if you just want the fastest, easiest with the slickest online experience, everything, it looks nice on the page. [00:18:05] The help sections are really easy to navigate. TurboTax does do that. Probably still better than anyone, but is it worth paying such a premium for and dealing with questions and ambiguity on cost? We didn’t think so this year. [00:18:21] Joe: Yeah, it’s really up to the user. Right. Uh, why is HR block your second runner up? [00:18:26] Eric: Yeah, so HR Block has just about all of the same bells and whistles as you get from TurboTax. It’s, uh, typically a tidbit cheaper, um, not significant. They don’t have quite the same level of import integrations, but for the places you can’t import, you can usually drag and drop a PDF that you get from your, let’s say your investment company. [00:18:48] You can just download the PDF, drop it into the h and r block website. Oh, cool. And they’ll read it for you and parse all the information and fill the form, which most of them don’t. I think if anyone from the tax companies are listening and you want a differentiator, the next time I do this, that’s a great one. [00:19:04] You should do that. Like AI can read your PDFs now. Um, there’s no reason a software companies shouldn’t be able to implement that, but surprisingly, the ones that really do it are TurboTax and h and r Block and the others. It’s a pretty big step down in what you’ll get from that. Another reason I like h and r Block for some people is if you are kind of uncertain about if you will need help, if you’re that person that that’s on the edge of, do I go with a per in-person accountant or do I do it myself? [00:19:34] H and r Block has locations all over the country and they make it really easy to convert. So let’s say you’re halfway through your taxes and you’re like, oh, I’m done. Throw your hands up. I just can’t deal with the rest. You can convert to an in-person experience and drive over to the office and just pick up where you left off, and with most of the others, like TurboTax and actually tax, tax, just launch one of these. [00:19:56] This year you can pay extra to have help from a. CPA or a a tax professional, licensed tax professional. Not always a CPA, but they’re always licensed. Sure. Like an enrolled agent. Yeah, exactly. An enrolled agent or a CPA. It’s usually one of the two. You can upgrade with TurboTax, you can upgrade to, I, I forgot the exact term, what they call it, basically hand off your entire tax return. [00:20:20] So you just upload all your files, drop ’em in a online folder, and they will parse out all the details for you. But for each level of service, you’ll pay more remember? Yeah. But yeah, h and r block, I like for that. You know, if you’re the, uh. Maybe you’re not the grandparent who’s afraid of computers, but you’re the, uh, the parent that’s on the edge. [00:20:38] I don’t know why I’m using that as an age or, you know, there’s young people who don’t like computers either. Let’s say you’re just the person who’s on the edge of if you wanna do it yourself or pay someone. ’cause it’s really, I think, the best starting place for that audience. [00:20:52] Joe: Well, it’s funny to me when I was reading your piece, Eric, is that, so then I scroll down and I start looking at the individual categories that you have, because while those are your overarching, Hey, you know, any, any person you are, those are good choices. [00:21:06] But if you’re this particular person, use these. I was surprised that in your very first category, best free tax filing software, I would think that free tax USA that won the overall would win that. But you’re like, no. If you’re somebody that qualifies for free filing. It’s a different winner. First of all, how do you know if you qualify to file for free? [00:21:28] And then second, if it’s not free tax, USA, which app should those people use? [00:21:33] Eric: Just about every tax software has a free tier. That’s not universal, but it’s the majority. And the free tier is usually pretty limited. It’s based on your annual income and which tax forms you have. One of the most generous free tiers among premium tax software is probably h and r Block. [00:21:53] There’s also an IRS free file program. You can go to, uh, most of the tax software providers participate, but it’s important to note if you start through the IRS free file portal, you can’t convert to a paid app. So if you are on the fence, don’t start that way. ’cause then you’re gonna have to retype all your information later and it’s a big hassle. [00:22:16] I’d start by looking at free as your priority. I’d actually skip most of the paid programs because there are a couple that are truly actually 100% free. And the one that we picked here as our winner for this year is Cash App Taxes. Or Cash App. You guys probably know from Cash App you can use to send people money and it’s like Venmo or PayPal. [00:22:38] It’s owned by Square uh, or Block Ink Net is their company name. They’re the payment processor, you know the little squares that you use to pay for, uh, the food trucks and stuff like that. Coffee shops. So they own that. They actually got it from Credit Karma. When Credit Karma sold to Intuit that owns TurboTax, part of the deal was that that spun off and Square bought it. [00:23:01] So cash app taxes 100% free. There is no way to pay for anything. They just don’t have it built in. It’s free no matter what. But with that, you don’t really get much support beyond their. Help section. So if you can’t figure it out through Googling and reading their help section, that’s not the best choice. [00:23:20] And there are a handful of situations, it’s pretty limited that they don’t support. The most noteworthy is if you have to file in multiple states. So if you live in Kansas City, Kansas and work in Kansas City, Missouri, and you need to do two state returns because of that, that might be an example. Or if you move sometime in the year, um, if you decide that you can’t handle this beautiful California weather and you need to go move to Minnesota in the middle of the year and you’ve have two state returns to file that you wouldn’t qualify, and that’s for any two state situation. [00:23:49] If you are average though, if you’ve lived in the same state all year and have pretty. Typical taxes, you could use it and it doesn’t cost anything. Um, a new one to me this year that is also totally free is Chime taxes. Uh, chime is the bank account provider. Yeah, right. Um, they’re like fee free checking and savings. [00:24:09] And the credit card that has no interest or fees, uh, pretty much. Um, there’s always asterisk pretty much, but typical user’s not gonna pay any fees from Chime. They’re awesome in that way. They have a free tax filing app. I mean, you have to be a Chime customer to get access and it’s all through their mobile app. [00:24:25] If you like Chime or if you are interested, that’s another route to get totally free tax filing. [00:24:30] Joe: Well, I know that historically like IRS free file and get your refund. These have, uh, income limits. My understanding is Cash App was one of the first ones that had no income limit. I mean, I mean, seriously when you said everybody can use it, it’s kind of one of a kind. [00:24:45] You’re not gonna go to these other places and be able to file for free. [00:24:49] Eric: Yeah, they were the first one that, back then it was called Credit Karma Tax Now Cash App taxes. It was the first one that I know of that just said, do your taxes for free online. Uh, which is pretty sweet. Who doesn’t like having more money? [00:25:01] Joe: Well, here’s one that our mutual fund, uh, or Robert Farrington, I remember really, really had a lot of appreciation for, and that was a student loan borrowers. The name of your site is college investor.com. So, so number one, a lot of student loan borrowers, but actually what I was referring to is this winner. [00:25:19] He really likes tax layer in a lot of ways, Eric. [00:25:22] Eric: Yeah, so tax layer is a standout for a handful of reasons. They, for me, for a lot of years, were kind of the, the big number four. So the big three were always. TurboTax H and r Block and Tax Act and tax Layer. I started to notice maybe a decade ago, and I think the first place that it really caught my eye was on Reddit. [00:25:43] I was, I’m, I’m a Reddit guy. I won’t tell you my username because that’s what Reddit’s all about, right? And I was, uh, cruising the personal finance and tax sub Reddits because that’s what all the cool kids do. People were talking about how they do their taxes, and I kept seeing people say they actually really like tax layer. [00:26:00] Uh, it’s a lot cheaper than the bigger competitors, and it works just as well. Um, so the price as it’s gotten more popular over the years has crept up a bit, but it’s still cheaper than something like TurboTax. I’d say it works just as well as something like Tax Act. Um, so it’s. Quality wise, worth being in the top three, four, or five options, but the pricing is a little better. [00:26:24] So that’s a reason we, uh, have been a fan there and they keep making it better. They keep improving it. They do have some of the PDF imports, like we talked about. Uh, you can get from h and r Block. It’s not quite as robust as what you get from h and r Block, but it’s better than most of the others. It’s definitely one we can get behind and say, if it looks like it would fit your needs, it’s worth checking out. [00:26:46] Joe: If I am an investor and I’ve got maybe lots of different stock positions, what’s my best choice for filing? [00:26:54] Eric: Yeah. So if you have a lot of trades, I’d say there’s a different answer. If you have a lot of investments versus if you have a lot of transactions. So if you have a lot of investments in general, but you’re not buying and selling a lot. [00:27:09] Any of them really could do the job pretty well. But if you have a lot of transactions, so you’re an active trader, TurboTax is still the easiest. As I mentioned earlier, you can type in your, let’s say you Schwab, fidelity, oh, chase, any of the big brokerages. You type in your information and your login information. [00:27:28] It will automatically download all of your transactions and it’s that import feature that wins the day. It’s just if you’re an active trader and you have a thousand trades over the year. Yeah, with just about everyone else other than probably h and r Block, you’re gonna be sitting there typing in a thousand transactions. [00:27:45] And if you are the kind of person who’s trading that much, spending, you know, two, three days typing in line by line, every trade is probably a deal breaker for that crowd. It’s probably worth paying a hundred dollars more, $150 more to just click and import. Do they win [00:27:59] Joe: for [00:28:00] Eric: crypto as [00:28:00] Joe: well? [00:28:01] Eric: Yeah, so with crypto it gets a little more complicated. [00:28:04] A little more nuanced. So if you only use something like Coinbase, Coinbase will give you a tax report. You can use that. You can import right into TurboTax or H and r Block or most of the others. But if you are a crypto owner like me, and you have your own hardware wallets or software wallets, or use multiple exchanges, you usually can’t just import all of that into something like TurboTax. [00:28:29] You’ll need an intermediary crypto tax software. Hmm. There’s two that I really like. One is called Coly, K-O-I-N-L-Y, and one is called Coin Tracker. So with those you link your hardware, wallet address, your software wallet, whatever wallets you’re using, whatever exchanges. Um, they connect to almost every exchange, hundreds of them with APIs. [00:28:49] They’re available. So you might need to be a little bit more techie, but you’re probably not doing crypto through all these exchanges if you’re not already a little more techie. So if you’re that person, you have a lot of crypto stuff going on, you’re probably gonna need to pay additionally for something like Coin Tracker or Coin Lee, and they will create the forms that you can then import into TurboTax or another app. [00:29:13] Joe: Boy, I know what a beast that can be, and to have some software and programs that can clean that up for me could be a lifesaver. Let’s say that I’m in real estate and I’m a buy and hold, uh, real estate landlord. Which one of these programs do I turn to first? [00:29:28] Eric: Yeah, so we picked tax layer for landlords, the pricing’s reasonable. [00:29:31] We were already talking about reasons we like tax layer, and it’s pretty well optimized for landlords. And once you get past, let’s assume you’re doing business accounting for your landlord business. Maybe you use something like QuickBooks or Zero or whatever you use. There’s lots of specific apps just for landlords. [00:29:51] At the end of the year, you should have a pretty good idea of what you made your p and l. That should all be together. If you come into doing your taxes with that information handy, then tax layer’s a great place to pick up and get your stuff all entered and get an accurate tax return. [00:30:07] Joe: And what’s amazing to me, and it felt a little random as I was reading through these. [00:30:11] You know, up until now, besides free, we haven’t mentioned cash app taxes, but here, cash app taxes is again, Eric, just because, and I think it’s specifically because they have this cool depreciation calculator that they use. Am I right there? [00:30:28] Eric: Uh, so, well for landlords, depreciation’s going to be really important. [00:30:32] We picked cash app taxes for side hustlers as a favorite. Um, the reason we did that is when you’re a side hustler, you might have multiple business entities or multiple Schedule Cs if you want to get into the nitty gritty. Me, I’m a business nerd, so I have an S corporation and all of my side hustles kind of funnel through that S corporation. [00:30:52] But the typical side hustler may be you’re an Uber driver or a door dasher, or you sell some, um. Trinkets at a local farmer’s market or a artworks on Etsy. There’s, there can be lots of different places you do this and as your side hustles get more numerous or complicated, you’ll start to pay a lot more with the turbo taxes and h and r blocks, where cash app taxes, uh, chances are, if you’re a serial side hustler, you’re the kind of person who’s trying to make more money and spend less money. [00:31:25] That’s part of why I think that’s a standout there is just, it’s the cost. Again, if you’re side hustling, trying to pay off credit card debt or side hustling, trying to save up a down payment, you don’t wanna spend an extra $120 on your taxes when you could do it for free, even if it takes a few more minutes. [00:31:39] Joe: Well, I guess that was my point, is that you’ve got Cash App as the runner up for landlords, and then to your point for side hustlers, you’ve got Cash app as number one and it’s kinda like you flipped because then, then you’ve got tax layer as the runner up. So it, it sounds like if you’re somebody that I. [00:31:55] Has the side hustle of real estate or any other side hustle. Those are your two go-tos. Like those are Yeah. Yeah. Tax layer and uh, and cash app. Unless you like one of our top overall picks more. Absolutely. Now let’s say then, Eric, that I wanna work with a human, but I want to do it directly through the computer. [00:32:13] You guys looked at that category. [00:32:15] Eric: Yeah. So for virtual tax prep, that’s what we called it. Uh, we picked h and r Block. Where that kind of came from was during Covid. People weren’t going into h and r block locations because, you know, COVID. So, uh, when we were all stuck at home, they were pretty innovative. [00:32:30] They were basically the zoom of tax prep at the time they were, ’cause they had that infrastructure and so many people around the country, they were able to just turn on their computers and say, all right, we’ll sit down with you. You can be at your desk at home, I’ll be at my desk in the office. We don’t have to worry about coughing and breathing on each other and we can do our taxes together or do your taxes. [00:32:51] Uh, so that’s why we picked them. They were really a leader in, um. Getting in-person tax help during covid, and they didn’t drop the ball there, they just kept that level of support available going forward. Just like you could switch and pull the lever and go into an h and r block, you can pay for a, a modest upgrade and work with someone and have a video meeting just like you’re watching us here on, on YouTube. [00:33:14] Right? [00:33:16] Joe: And that’s, you know, for people that need that extra, I don’t know, uh, layer of confidence, you know, that not only is do I have the app, but I have this person who can assure me that I’m doing it right. I think for, for somebody there, that could be a huge, huge, huge service. Yeah. Every year these are our most popular show notes, stackers. [00:33:36] So head to Stacking Benjamins dot com and you’ll find the show notes for today’s episode. But if you want to go directly there, I think you guys, I. I would imagine, Eric, there’s no way you don’t have your piece here pinned to the front page probably for the next month and a half. [00:33:52] Eric: Yeah, if you Google or uh, whatever search engine you like, if you DuckDuckGo it, is that a verb? [00:33:57] Now if you DuckDuckGo it, you can type in the college investor best tax software and it’ll come up towards the top. [00:34:04] Joe: And I shouldn’t even laugh ’cause I use Bing and everybody makes fun of me for Bing. [00:34:07] Eric: Yeah. I, I don’t bing, but I do duck, duck go some, I’ve been de googling my life a bit. Um, trying to, yeah, get a little more privacy focused. [00:34:14] And one way I’m doing that is I don’t only use Google to search now. [00:34:17] Joe: Well and it’s funny, I use Bing ’cause they pay me for search. Like I end up getting some money for search. Like what’s, what’s, what’s wrong with that? And those [00:34:25] Eric: 2 cents every couple days adds up. You over 20 years you’re gonna make a hundred dollars. [00:34:30] Oh it [00:34:30] Joe: totally is. It’s not much. It literally is like $35 a year. But hey, you know, and, and like you, you and I, I think search way more than the average person, right? We’re Oh yeah. Constantly on there. Eric Mann, thanks for helping our stackers navigate tax day. Again, I super appreciate you and the whole team over there at the college investor. [00:34:47] Eric: Yeah, thanks for having me back on the show. And uh, if you want to connect with me directly, go to eric.money in your browser no.com just Eric, do money and I’d love to connect with you [00:34:56] Joe: and we will have Eric’s go to link on our show notes as well. Everybody. Bye-Bye. [00:35:06] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and welcome to our world famous trivia segment. I created it with a lot of good tricks. I will show them to you. Your mother will not mind it all. If I do, as Joe’s mom always says, it’s fun to have fun, but you have to know how. So let me teach you a little fun. [00:35:24] How about a trivia question? What book was released on today’s date way back in 1957? And until I get back, you’re going to sit, sit, sit, sit. And you might not like it. Not one little bit. [00:35:48] Hey there, stackers. I’m guy who loves funny hats and guy who likes to be here. Oh, I like it a lot. Joe. Mom’s neighbor, Doug. I’ve been kind of misquoting lines from a bestselling book released way back in 1957. It’s a great book to read. When the sun does not shine, it is too wet to play, so you sit in the house, all that cold, cold, wet day. [00:36:09] What book is it? Of course, it’s maybe the greatest hit of the Man they call Dr. Seuss, the Cat in the Hat. Theodore Dral. That’s his real name. I think. Just a little extra trivia for you there. And now back to the two guys I like to refer to as thing one and thing two. Oh, come on, Joe and og. Oh, should have seen that one coming from a mile away. [00:36:34] That’s a high compliment. It’s as good as I can make it. Thing one and thing two. [00:36:38] Joe: I tried to get our twins. We were at Universal Studios and they had those T-shirts thing one and thing two. So I tried to have my twin. I I, I thought it’d be fun if you’re a twin to wear a thing, one thing, two T-shirt. [00:36:48] Neither one ’em want anything to do with that. They were like, Nope, we’re not doing it. So Cheryl and I bought ’em. [00:36:54] Doug: Nobody [00:36:54] Joe: wants to be thing [00:36:55] Doug: two. That’s the dumb one. Well, thing two’s kinda the crappy one, right? The crappy one? No, no. [00:37:04] OG: Down to 12, Doug. [00:37:08] Doug: It’s just your, your age is eroding by the minute. I shouldn’t have had coffee before we did that. Big [00:37:15] Joe: things to Eric Rose. Yeah, coffee was the [00:37:16] OG: problem. [00:37:16] Joe: Yeah. There’s a new sheriff in town, og free tax. USA [00:37:21] OG: free tax. USA. Yeah. Why? Why is it so difficult to have pricing upfront? Like, I don’t understand either. [00:37:27] Just tell me, just tell me what you’re gonna tell me and then tell me I. Then tell me what you told me. Like, make it really simple. It doesn’t have to be complicated. [00:37:36] Joe: It is interesting how we, we kind of think of this as one size fits all. Right? And as Eric explained, it truly isn’t. If you’re somebody that really, really wants the help of an enrolled agent, h and r Block has done the best job of putting those together, their enrolled agent community, and the ease of the software. [00:37:57] Uh, if you’re somebody that is eligible to free file, if you’re somebody that buys a lot of crypto, like you’re gonna, if you’re somebody who’s a real estate investor, don’t just go with, oh, this is the quote. Best, there’s, there truly is a best for you in your situation, depending on who you are and what you, what you’re looking for. [00:38:13] OG: Yeah. Pretty quickly you get to, and then you should just have a CPA that does them. Yeah. There’s a pretty quick acceleration from, you know, and then maybe it drops off, right? Like during different seasons of your life, just outta college first job. Okay, cool. Real estate investor, three kids, multiple different stock award options and you know, stock trading and crypto and all the things CPA, and then retiree pension, social security, little bit of dividends. [00:38:49] RMD, maybe back to right. Back to the software. Software, yeah. [00:38:53] Joe: But I think certainly if you’re somebody that is gonna do what Grant Seba suggested on Monday, which is you’re gonna go into entrepreneurship, that business starts to grow. Oh gee, there’s so many opportunities. There’s so many tax planning opportunities. [00:39:06] I think that having those smart people in your corner pays for itself, to your point, very quickly. [00:39:11] OG: It really does because it’s not even, and it’s hard to predict that stuff in advance. It’s more like what happens when you don’t have that synergy between your cashflow planning, your tax planning. Payroll, all savings, investing, like all that sort of stuff dovetails together. [00:39:28] And if you make one mistake in one place, it snowballs into other areas. You know, it’s like if you make a mistake in your payroll calculations or your CPA is not involved in the decision of how much you should pay yourself versus your S-corp filing of how much money you should take as dividends, well that affects how much money you can save in your workplace plan. [00:39:50] And if you over contribut in your workplace plan and that person’s not talking to the CPA or the payroll people, you know, there’s like all those things work together and, um, require some forethought. You know, like you were saying about the tax guide, it’s like tax preparation happens now, but also tax planning for 25 is happening now. [00:40:09] If you get to the end of March or April 15th and you’re like, oh, thank God I don’t have to worry about taxes again until next April. Yeah. I kind of think you’re doing it the wrong way. I think. I feel free to take May off and June off. But by July or August you might be looking at your tax planning for the rest of 25 and start thinking about how, you know, how this stuff’s gonna all play together to, to make good decisions. [00:40:31] You know, leading into your tax filing season of, of early 26. [00:40:36] Joe: Yeah. You’re not waiting till the end of the year to do your year end stuff. You’re thinking what’s the impact of that gonna be in the first place? [00:40:42] bit: Yeah. [00:40:42] Joe: It has to be, is it gonna be worth my time, my energy, and exactly how can I do these things in a tax efficient way ahead of time so that when I get the puzzle pieces together in February and I’m trying to figure them out in March with this tax software with a pro, like I already know where these pieces fit and that I have, have a fit to [00:41:02] OG: it. [00:41:02] Well, we were talking on Monday about tax deductions and some of it was, you know, a little silly, but for example, if you knew going into your tax filing season, so it’s 2025 right now and you’re thinking tax planning for this tax year 25 and you know. Hey, there’s no chance I’m gonna be taking anything other than standard deduction. [00:41:22] I don’t donate tens of thousands of dollars a year to charity. My mortgage interest or my property taxes don’t kick me Above 29,000, how much stress does that take off? You’re recording. You just go, I donate my money. I don’t have to keep, I don’t have to keep a receipt of this. I know I’m not using this in the future. [00:41:40] I know I’m not gonna benefit from keeping this one slip of paper from, you know, from this donation thing that I did for $35. Just, you know, that in advance. That’s great. This is one less thing to worry about, right? I take the standard deduction. I don’t have to worry. You know, I now, versus I’m planning on making a big donation this year. [00:41:59] Now I need to see how that factors into my. Tax deductions, am I recording? And where the best places are to donate money from and all that other sort of stuff. That’s a whole different thing. But it’s not just, it’s not just making good decisions in terms of planning, but also like how that dovetails into record keeping and you know, the stress of all of this stuff. [00:42:19] Like just going, I don’t have to care about this. It’s like the HSA thing. People say there’s two sides to that story, right? Like, save up your HSA or freaking use it all. So you don’t have to worry about keeping track of saving it up. Like just use it one less thing to worry about. [00:42:32] Joe: And both ways, a big win. [00:42:34] Yeah, absolutely. Both ways. A big win. Uh, big thanks to Eric for hanging out. We got an interesting headline today. [00:42:41] headlines: Hello darlings. And now it’s time for your favorite part of the show, our Stacking Benjamins headlines. [00:42:48] Joe: Our headline comes to us from the Wall Street Journal. This is written by Spencer Jacob. [00:42:52] Stocks have a big expensive problem. Spencer writes, he says, strange times are a foot in the investing world. Your portfolio probably isn’t ready for them. The US stock market is the big dog, the global stock market, and recently it’s taken on Clifford Proportions talking about, it’s so funny, we’re talking about kids books in the trivia, big Red Dog, Clifford, at two thirds of the global market value that outweighs America’s one quarter of the world’s economy and 4% of the world’s population, but the US tail has usually wagged the global dog. [00:43:21] Recently though that relationship has broken down could signal an investing upheaval. I. And very poor returns for big US stocks in coming years. Analyst at Data Trek research note that the usual correlation between the main US benchmark, the SP 500 and the M-S-C-I-E-A-F-E, which is an index of non-US developed stocks, has historically been a very high 0.83. [00:43:42] Over the past 100 days. It’s been 0.54. And he talks about OG how that is bigger than it sounds over [00:43:49] OG: the past three whole months. Your long-term decision making should be based on the last a hundred trading days. [00:43:55] Joe: We’ve seen, uh, stock market declines, og we’ve seen, uh, yeah, [00:43:59] OG: some increased volatility. [00:44:00] Joe: Yeah. [00:44:01] What’s going on here? [00:44:02] OG: Oh, wouldn’t I like to know? I mean, at the end of the day when you look at your. Investment allocation, you have to be okay with allocating to outside countries. And I think what his point here is, is that the US in particular large tech companies have done so well for so long. And I almost think that there might be a generation of investors now who think that the only place to put money is the s and p because they don’t have any experience of any other asset class beating the s and p, whether it’s small US companies or international or emerging market. [00:44:40] And of course we know over long periods of time that can’t be the case. If big tech companies or big large US stocks have done well for a period of time, that doesn’t mean they always will. And that doesn’t mean all of your money should be in that you have to have some money in small companies or some money in value companies or some money in non-US companies or emerging markets. [00:45:01] And, and I think it makes sense if you look at kind of historical stuff that. Over performance is followed by periods of time of underperformance. The hard part about all of this is of course, trying to guess when that over performance ends and when does the next rotation into whatever that’s gonna be happen. [00:45:21] And do you guess, right, or do you just choose to be invested in all of the things all of the time and then you don’t have to worry about it? You know, rebalance, part of your portfolio went up last year. Large US tech companies did. Again, you sell that at a profit, you rebalance it into the things that didn’t do as well last year. [00:45:40] Might’ve been international or small companies, and you’re back to where you wanna be. [00:45:44] Joe: The piece of this that I always find interesting too is when we go into any type of decline, and like you, I’m not predicting whether this is a long-term decline, just a short little three month. Who, who the hell knows? [00:45:55] Yeah. No, nobody ever knows. But when, when, when we go into declines, og, if they do end up being long-term declines, the asset classes that led just previously to the decline are not the asset classes that get us out of it. In other words, we see a sector rotation, right? We see this very natural changeover from the things that led before and every single time. [00:46:17] By the way, what leads us to that quote bubble is the fact that that one part of the market just got way overheated and then it takes them a while to regain their footing, whatever sector that is, while everybody else gets it together. And I, and I think by the way, that’s a reason why you don’t wanna play the sector game. [00:46:35] You don’t wanna play the sector game because you will have these prolonged periods of horrible times while a whole sector gets its collective crap together. Figures out how to innovate more, or in this case, maybe how to use AI better, or whatever it might be. It’s really tough to buy and hold when you’re a sector better. [00:46:53] OG: Well, I mean, there’s two competing things here. One is the phrase more money’s been lost preparing for the next recession than in actually any of the recessions. And one of the things you said a little bit ago, which was kind of interesting, was like, if we have a long-term decline, which by the way would be defined as what, two years? [00:47:11] You know? Yeah. Two and a half. It’s [00:47:12] Joe: like a, that’s a very long decline. [00:47:14] OG: That’s an insanely long time. And by the way, it’s like a drop in the bucket. You know, like two years ago, my, my kid was in a car accident in Jan. Like he wrecked his car in January, right? Oh, no, it was January of last year. I thought it was January of this year. [00:47:28] It’s already been 15 months since his, you know, second car accident. You know, it’s like, it, it’s time is just, you know, a construct I guess. I don’t know. But at the end of the day, even long term is not that long, right? Two years seems like a long time when you’re in it, but in, in the rear view mirror, it’s not that long ago, but there’s no way to know when is the top and when is the bottom. [00:47:51] We just don’t have any idea, to your point about sectors, Joe, when are we in a prolonged decline? When are we just in a little blip? And the best course of action always across the board is just be diversified, rebalance on your birthday once a year, and don’t pay attention to it, and life will go on. [00:48:11] You’ll be all right. [00:48:11] Joe: Yeah. This wouldn’t be a media piece without predictions in it, og, which always make me laugh because they’re always wrong. However, what What is interesting is this group of research affiliates looked at valuations and their prediction, which is not worth the papers written on, but I do find this interesting. [00:48:29] We talk about rotation and buy and hold and don’t be a sector investor. Mm-hmm. The predicted return for us large growth stocks, according to them. Is 1.8% over the next decade, which would be negative after inflation. Spencer writes the expected annual return for non-US developed markets, 10% topping that emerging markets, emerging markets value, specifically at 10 and a half. [00:48:51] Is any of that worth anything? No, but it does go back to what we’ve been talking about, this reversion to the mean and don’t do the bet. Yeah, don’t bet. [00:48:59] OG: I mean, it’s just a rubber band snaps in one direction, comes back the other [00:49:03] Joe: man. Speaking of not betting time for our TikTok minute, this is a part of the show where we shine a light on a creator who’s either, uh, sharing some brilliance or air quotes, brilliance. [00:49:11] Today I’m going straight up YouTube video, though. This is not a short. Mm-hmm. This is a YouTube video that I found. Yeah. Uh, you think we’re gonna hear brilliance or air quotes? Brilliance. [00:49:22] OG: Since we’re talking about taxes, I’m gonna, I’m gonna err on the side of, uh, this is, uh, this is gonna be great. Yeah. [00:49:29] Whoa. Be hot. [00:49:31] Joe: Whoa. Hot take. Well, this coming in, this, this one actually is not going to be about taxes. Ah, I’m gonna go with the theme that Spencer Jacob was on the Wall Street Journal writer. Mm-hmm. Who’s also been on the show before. By the way, Spencer talking about investing and some people always looking for the hot, hot thing. [00:49:48] aftershow: Mm-hmm. [00:49:48] Joe: This, uh, YouTube creator is instructing people on how to make a bunch of money with. Crypto, oh boy. Meme coins. [00:50:01] tiktok: Drug pull is powerful, but still so simple that I can explain it to you in under a minute. To pull it off, you need two things. Some fresh trending news or a meme and solves for the initial pump. [00:50:10] Here’s how it works. With a real life example. Binance is official Twitter account, posted a photo of their dog within minutes. A rug puller created a meme coin based on that photo and bought 75% of the coin supply, paying 70 saws in one purchase because of this large, buy the coin, got a king of the hill spot and free advertising on the main page. [00:50:28] Random unsuspecting traders saw the coin associated with trending news in an almost completed bonding curve, driven by greed. They bought the coin without checking for obvious red flags. As a result, shortly after its creation, the coin was almost sent to radium, but instead it was dumped earning its creator, 7.6 Saul or $1,000 In just one minute. [00:50:47] The same time you spent watching this video, I checked his profile and found that he had previously created dozens of coins using the same method, making hundreds of thousands of dollars. He and others like him are still making millions with the simple tactic, so be careful and always check coins for obvious rug pull signs, subscribe if you found this useful. [00:51:04] OG: Such is not a person that is 100% some crappy AI generated BS commentary, and that [00:51:11] Doug: AI invented several words for that piece. Yeah, I’ve never heard before. [00:51:15] OG: I [00:51:15] Doug: didn’t. Well, I don’t care about any of that. What [00:51:18] Joe: I [00:51:18] OG: care about. You say creator. It’s not a creator. It’s a computer program. [00:51:22] Joe: And what disturbs me is the number of people that are watching these rug pull videos the way to make money OG is on other people’s stupidity according to whoever’s behind this video. [00:51:33] OG: Is that any different than investing continuously when the market’s going down and half the world is losing their minds, and you’re just like, I’m just gonna keep putting money in my 401k and my Roth and my brokerage account. I’m making money on other people’s stupidity. [00:51:47] Joe: I love the idea of making money off other people’s greed. [00:51:50] I mean, I, I love what that, that that thing said about, that’s several red flags and people are so excited about the new meme coin that they just mm-hmm. Jump in thinking that all this excitement equals some big gains. There’s huge red flags all over these projects. And yet how, how many times have we reported on stories where people just lose their ass on the latest coin? [00:52:10] You know what’s funny? You can’t even find the Tua girl now. You can’t find her. She’s, I went looking for her podcast man. She is gone. Like she is [00:52:19] OG: gone. Yeah, she got like a hundred million dollars. She scammed everybody out a bunch of money ever since [00:52:23] Joe: the the rug pull, right? Changed her name. So disturbing rug pull girl. [00:52:27] So disturbing when you see people that are looking for the shortcut and end up losing tons of cash again because there’s professionals up there, is it too much [00:52:35] OG: to ask for people who have all these meme coins that just go belly up and is it just too much to ask for all of ’em to go away? [00:52:41] Joe: Please God, go away. [00:52:42] Yeah, well it’s a great story. I dunno. Gives us fodder for the show. Here’s some more idiots that got scammed again when it was right, right in front of you the whole time. Very sad. Alright, let’s go out to the back porch, uh, and find out what’s going on in our community before we say goodbye. Doug, uh, what do we got on tap today? [00:53:02] Doug: We had, this was a fun one, and I know that, uh, you’re familiar with this, Joe, but I’m gonna toss this back to you now that we’re on the back porch because you told me about a great note you received. I thought it was a great story and we should talk about it here on the back porch while we’re drinking our cocktails. [00:53:17] Joe: It’s so funny. Hey, Doug, let me throw it to you so you can throw it back to me. Yeah, yeah. Watch this, uh, tennis match here. Yeah, I did. I got a great note from our friend, uh, Minosh. Uh, she is a recently retired dental hygienist. I met her and her awesome husband at the Las Vegas Meetup in November. By the way, they went to one of the Chautauqua events that are big in the financial community. [00:53:40] I believe they went to one in Portugal and, um, spent a lot of time with Doc G. But she said she wanted to share a small world incident that happened after the Las Vegas meetup. She said, long story short, I need a new dryer. Thought I’d try looking at nextdoor. Found the perfect used one. Went to pick it up, met the man and I’m like, you look familiar. [00:54:02] Did you attend the Stacking Benjamins meetup? And he said, yes. And it was our mutual friend, Sterling. COG. We’re getting people together at our meetups, people up on people making the, the the friendships blossom and stackers saving stackers money. That is so funny. [00:54:19] Doug: I wanna know more about the dryer, like menache, like let everybody know in the basement did, did the dryer work, is it, did he leave the lint in it? [00:54:28] Yeah. Did he clean out the, the lint catch before you bought it? All Doug wants for [00:54:31] Joe: you is to hang Sterling [00:54:32] Doug: out to dry. Well, I mean, or she could be like, oh, it was sterling clean. It was, it was amazing and I got a great deal on it. And in fact, Sterling just gave it to me for free since we wrote stackers. [00:54:45] We don’t know. I just need more to this story. That’s [00:54:48] Joe: what should have happened. Sterling. You should have given it to her for free. I mean really once, you know, knew that it was Mano, she should have given it to her for free [00:54:54] Doug: Stacking Benjamin’s way. We give the show to you for free. So you should give your dryer away for free. [00:55:00] Joe: Follow our lead. Thanks for the note, minosh. And it was, uh, great hearing from you again and, and meetups. I think my next meetup may be in Boston. My daughter is graduating. I would love to have a meetup in Boston again, while I’m there. See those Boston people? We, we met at a microbrewery that was a former bank and there’s a room you can have your meetup in. [00:55:21] That’s the bank vault room, which is pretty cool. We didn’t do our meetup there, but, uh, but maybe we will this time. Uh, stay tuned. If you don’t get the 2 0 1, you wanna make sure you get that so you know where our next meetup’s gonna be. All right, Doug, I think that’s gonna do it for today. Thank you everybody for hanging out with us. [00:55:37] Thanks to Eric Rosenberg for going over all the tech software options and OG for slapping people around when it comes to this playing these sector bets and craziness. Doug, let’s, uh, do the top three. What are the three things maybe we should have? Put on our to-do list during today’s episode. [00:55:57] Doug: Well, Joe, first take some advice from Eric Rosenberg. [00:56:00] Choose tax software based on your situation, not based on commercials or on which one you think might be best. Second, that new crypto coin rug pull is now a way people are making money and they’re doing it at your expense. But the big lesson, wow, there’s so much great advice in this Seus book. Like how come I’ve never read this goodness before? [00:56:24] Listen to this one. I know it is wet and the sun is not sunny, but we can have lots of good fun. That is funny. I mean, that’s just. It’s worse to live by right there. We just did that, didn’t we? Of course we did. Yeah. Thanks to Eric Rosenberg from the College Investor for joining us. You’ll find the College Investors Tax guide@thecollegeinvestor.com, or we’ll have a link in our show notes. [00:56:50] Speaking of tax software, tax planning doesn’t just happen in March and April. It’s all year long. That’s where our tax guide comes in. You buy it once and it’s yours forever. Head to Stacking Benjamins dot com slash tax guide for details. This show is the property of SB Podcast, LLL c, copyright 2025, and is created by Joe Saul-Sehy. [00:57:14] Joe Ganson help from a few of our neighborhood friends. You’ll find out about our awesome team at Stacking Benjamins dot com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. Oh yeah, and before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. [00:57:36] 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, Duggan. We’ll see you next time back here at the Stacking Benjamin Show. [00:58:41] aftershow: Don’t do a lot of [00:58:42] OG: movies, don’t have a lot of time, but, um, happened to catch this one on Apple TV plus. Is that the correct? I think so. Phraseology, yeah, for what that is sounds right. The pay [00:58:50] Joe: for [00:58:50] OG: version. My oldest wasn’t feeling very well. The other one was on, you know, staying at somebody else’s house. [00:58:55] Listen, Caroline, were I. I don’t know, doing something. So anyways, we sat and watched this movie called The Gorge on Apple tv. Plus [00:59:11] trailer: I have new orders that require me to go dark for at least a year, maybe more. A special assignment in an undisclosed location [00:59:24] as an elite sniper. Are you presently under any private or military contract? [00:59:29] Doug: No, there’s not a lot of reasons for me right now. [00:59:34] trailer: What if I gave you a reason? [00:59:40] There she is. West Tower Observation. Post your home for the next 365 days. There is no outside communication here. What’s that? On the other side? That is East Tower. Contact with the other side is strictly forbidden. So what’s the mission to keep people from going in the gorge? No, you need to stop what’s in the gorge from coming out. [01:00:06] What the hell is that? The gorge is the door to hell and we are standing God at the gate. [01:00:14] OG: So that’s the, uh, intro part of the show. Miles Teller. Sounds like a laugh a minute. Yeah. Wow. It sounds a little bit more intense than it is. It’s PG 13, so there’s not too much. The three major actors in this movie, Sigourney Weaver, probably the biggest name, miles Teller, most people familiar with, and Anya Taylor Joy is the other lead actress actor in this movie. [01:00:38] And those two are on opposite sides of this big gorge that’s kind of covered in smog. And you’re not supposed to have contact with the other side, but boy meets girl and. Boy does what boy does to meet girl in person, you know, like pretty girl over there. I know I’m not supposed to talk to her, but I’m gonna anyway. [01:00:57] And so they start communicating back and forth. One thing leads to another, something bad happens. You get a pretty clear sense early on like what the gorge is about. And [01:01:07] Joe: it’s the gateway to hell. Ochi, I heard the trailer. It’s the gateway to hell. It’s the [01:01:10] OG: gateway to hell. Interesting twist. Something happens, they find themselves in the gorge so they uh, they have to escape. [01:01:17] And um, kind of uh, kind of an interesting twist on what actually it is. You know, thumb, three and a half ways up. I mean, fun popcorn movie. [01:01:28] Doug: Three and a half ways. [01:01:30] OG: Yeah, three and a half ways like that. Like not all the way up. So [01:01:33] Doug: you’re pointing at like a 45 degree, maybe 60 degree angle. [01:01:35] OG: Yeah. Okay. Like 70, 80% good popcorn movie. [01:01:38] PG 13. Not a ton of blood and guts kind of fun. ’cause they all machine guns, they jump outta airplanes, sniper shots, whatnot. A little love story in there and, uh, and chaos. So kind of fun. [01:01:52] Doug: Is the love story between Miles Toler and Sagourney Weaver? [01:01:55] OG: No. [01:01:56] Doug: No. Could be like a, a may December kind of thing. [01:01:59] OG: No, she’s the one that gives him the assignment. [01:02:01] Okay. Pretty simple to, to follow this along. You know, the, the roadmap is pretty well worn on this type of storyline, but, um, you know, if you’re bored on a Tuesday afternoon and you don’t have anything else going on, flip it on Apple tv. Plus [01:02:15] Doug: if you want twists and turns and stuff, you just don’t see coming. [01:02:19] Love is Blind. Season eight, baby. Oh, that is right up your alley. Oh, yeah. That’s hard hitting stuff, [01:02:27] OG: but I liked it. Alex liked it. Fun to watch. A little zombie ish. You know, [01:02:32] Joe: it sounds fun. Sounds like a campy ish fun movie. [01:02:35] OG: I mean, as fun as machine guns, shooting zombies, trying to escape from the gorge. [01:02:39] Could be. That’s exactly what you’re looking for. There’s lots of explosions. There’s sniper shots. Wow. Who [01:02:43] Joe: knew you’d like that one? Yeah. You’re playing against your [01:02:46] OG: type. The opening scene is a sniper shot and, and then jumping out of airplanes and you know, what [01:02:53] Joe: did you start crying like 25 seconds in? [01:02:55] Were you crying out of [01:02:56] OG: joy? No. This is so, so wonderful. No, I was just like, let’s watch this. This looks like my kind of movie. Protecting the World from the Gorge. Let’s get it. Did you [01:03:04] Doug: ever, I, I can’t remember, I think I’ve asked you this, but I don’t remember your answer. Did you ever watch the show that Joe and I both thought was right up your alley called American Prime Evil, the Dark Western Western? [01:03:15] So [01:03:15] OG: you asked me this, generally speaking, every four to seven days. Yes. And I have not because so don’t have a lot of time. [01:03:23] Doug: It’s my subtle way of saying Watch it. Damn it. Because you will like it. [01:03:27] OG: I will [01:03:28] Joe: for sure. [01:03:28] OG: Maybe [01:03:28] Joe: season two. The night agent was really good. Season two. [01:03:32] OG: Oh, you know, I started watching that. [01:03:33] That’s the one with the, it starts out where there’s a bomb on a train. Right. Like season one is, he’s like, uh, no. [01:03:39] Joe: Season one, he works in the basement of the White House and he’s gotta monitor this phone that doesn’t ring. Yeah. So, and then it [01:03:44] OG: rings and it’s something about a bomb and a train or something, [01:03:47] Joe: right? [01:03:47] No, it’s these, uh, people call in and there’s, uh, that’s right. And there’s people at their house and they gotta try and get them. [01:03:54] OG: I started watching some of that. Is it good? [01:03:55] Joe: Yeah. Doug didn’t like season one. I like season one a lot. And then, uh, season two I thought was even better than season one. Uh, I’ve, I’ve very much enjoyed season two.
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