The Best Tax Prep Software of 2025 (SB1655)

Summary

The Stacking Benjamins Show - Episode: "The Best Tax Prep Software of 2025 (SB1655)"

Release Date: March 12, 2025
Hosts: Joe Saul-Sehy, OG
Guest: Eric Rosenberg from The College Investor
Podcast Network: Cumulus Podcast Network

---

Introduction

In this episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and OG delve into the realm of tax preparation software, aiming to guide listeners through the myriad of options available in 2025. Joined by Eric Rosenberg from The College Investor, the trio provides expert insights to help listeners choose the best tax software tailored to their individual financial situations.

---

Tax Preparation Software: Navigating the Options

Guest Introduction: Eric Rosenberg

Eric Rosenberg, a seasoned analyst from The College Investor, spearheads the discussion on tax software. With extensive experience in financial research, Eric brings a nuanced perspective to the table.

Choosing Between Software and Professionals

Eric begins by addressing a fundamental question: "Who should use tax software versus who should employ a professional accountant?" [12:17]

Eric Rosenberg: "If you're comfortable using a computer, navigating online banking, and handling emails, most modern tax software can work for you. However, if you're not tech-savvy or have highly complex financial situations, consulting an in-person accountant might be the better route."

Best Overall Tax Software: FreeTax USA

Challenging the long-standing dominance of TurboTax, Eric introduces FreeTax USA as the top choice for 2025. This software stands out for its affordability and transparency.

Eric Rosenberg: "We picked FreeTax USA as our top overall. While it's not entirely free for everyone, it's significantly cheaper than TurboTax and offers excellent value for those with straightforward tax situations."

TurboTax: Still a Top Contender but with Caveats

Despite the introduction of new competitors, TurboTax remains a prominent player. However, Eric points out issues related to pricing transparency.

Eric Rosenberg: "TurboTax offers a slick, user-friendly experience with features like automatic imports from banks and investment firms. However, their pricing can be unclear, often leading to unexpected fees at the end of the filing process."

Runner-Up: H&R Block

H&R Block secures the second spot, praised for its balance between ease of use and cost-effectiveness. It also offers unique features like PDF imports, enhancing its functionality.

Eric Rosenberg: "H&R Block is nearly as easy to use as TurboTax but typically costs a bit less. They also allow users to drag and drop PDFs from investment companies, which many competitors don't offer."

Special Mention: TaxSlayer and CashApp Taxes

• TaxSlayer is highlighted for specific user groups like landlords, offering reasonable pricing and robust features tailored to real estate investors.

• CashApp Taxes emerges as a favorite for side hustlers due to its affordability and essential features without the premium price tag.

Eric Rosenberg: "For landlords, TaxSlayer provides optimized tools to handle property-related deductions effectively. Meanwhile, CashApp Taxes is ideal for side hustlers who need to manage multiple income streams without incurring high costs."

Crypto and Complex Tax Situations

For crypto enthusiasts and active traders, traditional tax software might fall short. Eric recommends specialized crypto tax software like Koinly and CoinTracker to handle the intricacies of cryptocurrency transactions.

Eric Rosenberg: "If you're deep into crypto trading with numerous transactions, using intermediaries like Koinly can simplify the process. These tools generate the necessary tax forms that can then be imported into your main tax software."

Notable Quotes:

• Joe Saul-Sehy [08:38]: "If you’re a stacking Benjamin’s 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."
• Eric Rosenberg [15:09]: "FreeTax USA is a great choice if you have relatively straightforward taxes and want to do it the cheapest way possible while still paying for a more premium service."

---

Headlines: The US Stock Market's Big Problem

Transitioning from tax software, the hosts discuss a concerning headline from the Wall Street Journal by Spencer Jacob, titled "Stocks have a big expensive problem."

Key Points:

• The US stock market, representing a mere 25% of the global economy and 4% of the world’s population, dominates two-thirds of the global stock market value.
• Historically, there has been a high correlation (0.83) between the S&P 500 and the MSCI EAFE index of non-US developed stocks. However, this correlation has plummeted to 0.54 over the past 100 trading days.
• This breakdown in correlation may signal an impending investment upheaval, potentially leading to poor returns for large US stocks in the coming years.

Discussion Insights:

• OG [50:10]: "Over the past three whole months, your long-term decision making should be based on the last 100 trading days."
• Joe Saul-Sehy [52:05]: "We’ve seen stock market declines and increased volatility. The hard part is trying to guess when the overperformance ends and when the next rotation begins."

Investment Strategies:

• Diversification remains crucial. Relying solely on large US tech stocks, despite their recent success, may not be sustainable.
• Sector rotation is inevitable, where underperforming sectors catch up, emphasizing the importance of a balanced portfolio.

OG [54:32]: "The best course of action is to be diversified, rebalance on your birthday once a year, and don’t pay attention to it. Life will go on, and you’ll be all right."

Notable Quotes:

• Joe Saul-Sehy [55:19]: "The predicted annual return for US large growth stocks is 1.8%, which would be negative after inflation. Non-US developed markets are expected to return 10%, and emerging markets value at 10.5%."

---

Other Segments

Trivia with Doug

Doug adds a light-hearted trivia segment, engaging listeners with interesting facts and humorous interactions:

Doug [38:43]: "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."

TikTok Minute: Crypto Rug Pulls

The hosts showcase a TikTok-style segment highlighting the dangers of crypto rug pulls—schemes where creators scam investors by creating trendy meme coins and abruptly selling their holdings for profit.

TikTok Video Segment [56:21]: Explains how rug pullers use trending news and memes to pump up meme coins, attracting unsuspecting investors who then face significant losses.

Joe Saul-Sehy [57:53]: "It's really sad. People are losing tons of cash because there's professionals behind these scams."

---

Listener Stories and Community Engagement

Listener Story: Manoj’s Dryer Purchase

Joe shares a heartwarming story from listener Manoj, a retired dental hygienist who found a used dryer through Nextdoor and discovered it was owned by a fellow Stacking Benjamins meetup attendee, Sterling Cog. This incident underscores the community-driven spirit of the podcast.

Doug [59:22]: "We are getting people together at our meetups. People Helping People, making the friendships blossom, and stackers saving stackers money."

---

Conclusion

The episode wraps up with key takeaways and actionable advice:

1. Choose Tax Software Based on Your Situation: Evaluate your financial complexity and tech-savviness before selecting a tax preparation tool.
2. Beware of Crypto Scams: Stay informed about the tactics used in crypto rug pulls to protect your investments.
3. Diversify Your Investment Portfolio: Avoid over-reliance on any single market or sector to mitigate potential risks.

Doug [62:17]: "Choose tax software based on your situation, not based on commercials or on which one you think might be best. And be cautious of crypto rug pulls—they’re making millions at your expense."

Final Words:

Joe encourages listeners to visit StackingBenjamins.com for detailed show notes and resources, including Eric Rosenberg’s tax guide.

Joe Saul-Sehy [63:49]: "Before making any financial decisions, speak with a real financial advisor. This show is for entertainment purposes only."

---

Notable Quotes with Timestamps:

• Eric Rosenberg [12:17]: "If you're comfortable using a computer, most modern tax software can work for you."
• Eric Rosenberg [15:09]: "FreeTax USA is a great choice if you have relatively straightforward taxes."
• OG [50:10]: "Over the past three whole months, your long-term decision making should be based on the last 100 trading days."
• Joe Saul-Sehy [52:05]: "The hard part is trying to guess when the overperformance ends and when the next rotation begins."
• Joe Saul-Sehy [55:19]: "The predicted annual return for US large growth stocks is 1.8%."
• Eric Rosenberg [17:52]: "Free Tax USA feels easier to remember and is a good choice if you have relatively straightforward taxes."
• OG [57:25]: "Rug Pull is a powerful but simple way scams are executed in crypto."

---

For more insights and detailed discussions from this episode, visit StackingBenjamins.com and explore their comprehensive tax guide tailored to help you navigate tax season with ease.

Transcript

[Joe Saul-Sehy]

Small business owners. State Farm's there with small business insurance to fit your specific needs. Whether you're starting a new venture or growing an existing one, State Farm helps you choose the right coverage to protect what matters most. Working with a local State Farm agent helps you understand your coverage options, offering local support to help you achieve your goals. Focus on turning your passion into a thriving business, knowing your insurance can change as your business grows. State Stay Farm here to help you succeed with your business. Like a good neighbor, Stay Farm is there stackers. Are you working on your debt plan and you're trying to lower your interest rates? Navy Federal Credit Union is offering a 0% intro APR on credit card balance transfers for 12 months and get 250 when you spend 2500 dollars in your first 90 days on a cash rewards or cash rewards plus credit card. Navy Federal.org our members are the mission Navy Federals insured by NCUA after the intro rate expires, variable APRs are 14.9% to 18% based on credit worthiness. Rates are subject to change. ATM fees for cash advances are up to $1 at non Navy Federal ATMs.

[OG]

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, nobody will ever point to these two clowns and say, this was how you should have been stacking Benjamins.

[Doug]

Live from Joe's mom's basement, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor Doug, and 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.

[Joe Saul-Sehy]

I love the guy that stops the open partway through to pat himself on the back. Man, I got that.

[Doug]

I've rehearsed and I rehearsed and I rehearsed like yes, you're so good.

[Joe Saul-Sehy]

You're so good. You're so good.

[Doug]

Don't you worry, listener, because today we're going to 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. 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. Here I am patting myself in the back again. 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 Jo and. Oh, jj.

[Joe Saul-Sehy]

I love that when the bank account stops them from laughing like, oh, hey.

[OG]

Oh, wait a minute.

[Joe Saul-Sehy]

Hold on. Hey, everybody. Welcome to eight digits in the bank account. For the Win podcast, I'm Joe Salsihai.

[Doug]

Wait a minute.

[OG]

Little light of that.

[Doug]

Yeah, that would be good.

[OG]

Does that include the decimal point?

[Joe Saul-Sehy]

A decimal point in six places behind it.

[OG]

Still pretty good, honestly.

[Joe Saul-Sehy]

Hey, 10 bucks is 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.

[OG]

We're playing it for you here again today.

[Joe Saul-Sehy]

We're just gonna hit. Just play that again. 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 heated battle. Every year for countless years, it's been, hey, just do TurboTax. Just, just do TurboTax. So does TurboTax hang on to the.

[OG]

Crown last year fast, my friend.

[Joe Saul-Sehy]

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 going to dive into that today, but first, let's meet the team OG how are you doing on this fine Wednesday?

[OG]

It's happy to be here.

[Joe Saul-Sehy]

You and I, we had a high winds recently and you took a nice video of all the stuff that was under. Under your rooftop. No longer under your rooftop.

[OG]

Like you had a bunch, including my rooftop. Yeah, your.

[Joe Saul-Sehy]

Your backyard was. Was a little messed up. How. How high did the winds get by you?

[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.

[Joe Saul-Sehy]

I think.

[OG]

No, the 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 we got to go swimming. I got to go swimming. It was not. The pool was not warm enough to go swimming. But people tell me cold plunges are good things. So I cold plunged myself into the pool to get all my stuff.

[Joe Saul-Sehy]

Just to get all your stuff out of the pool?

[OG]

Yeah, it was awesome. Thankfully, my son helped and he's a little bit of an engineer, so he was like, hold on, dad. Before you slow down Marine. Before we just go charging into battle, 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 way to get some of this out without having to get wet first. And I'm like okay, cool. So he fashioned a little grappling hook type device and we dragged a bunch of stuff out of the pool without having to get wet. So that was nice too.

[Joe Saul-Sehy]

But then he just went in for fun at the end. Get the gold plunge.

[OG]

I didn't 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 degrees. I don't.

[Eric Rosenberg]

It's the health benefit.

[OG]

Like well what is heart attack?

[Joe Saul-Sehy]

I don't think the point of it is that. It's. Wow, this is great. I love icy cold water. That's not the point, is it?

[OG]

I mean, I think so. Yeah. Some health benefits of some kind.

[Doug]

It reduces your overall inflammation in your system.

[OG]

Oh, that's what they say.

[Doug]

It's an anti inflammation thing which leads to lots of other stuff.

[OG]

I'm Pretty sure a 150 rate heart rate would increase inflammation and stress and all manner of stuff. But I don't know.

[Joe Saul-Sehy]

One more thing to talk about before we get to our big stuff today, which is that Big ten tournament starting now. So I got the Sparty mug all ready to go, ready for my team.

[Doug]

We're recording this ahead of time and it hasn't started yet. 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, ain't nobody beating them. They put 100 spot on a team with two first round draft picks on Rutgers on Ruck. 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 100 spot on them.

[Joe Saul-Sehy]

Isn't it? While how Rutgers athletics now in football and in basketball. Just, just not the team that was there when they entered the Big ten.

[Doug]

Thank you. Big Ten money, bank account.

[Joe Saul-Sehy]

Well, we got a great show. We're gonna talk.

[OG]

Hold on, hold on, hold on. What's their record?

[Doug]

Oh the record. That's what I'm saying. Their record belies their talent and their basketball team. I Think they were as of last night, I think they were 14 and 15. They had a rough.

[OG]

So they're basically like all, there's no change.

[Doug]

Well, they used to be a lot worse than that.

[Joe Saul-Sehy]

They used to be a lot worse.

[Doug]

Before they were in the Big Ten in both football and basketball. They got a great football.

[OG]

We're 500.

[Joe Saul-Sehy]

And when they started the Big Ten. Oh, man.

[Doug]

But they have two. Every consensus, like every analyst says two of their guys are going first round.

[OG]

All right, we'll see.

[Doug]

So they got talent.

[Joe Saul-Sehy]

Well, going first round when it comes to tech software is the college investor.

[OG]

Going first round in my book, number number one.

[Doug]

I appreciate that OG but Joe's segue was that was pro level stuff. Joe, I got to pay you your dues there.

[Joe Saul-Sehy]

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? 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, cheapest. Exactly. Eric Rosenberg's been with that team for a long time. Eric and I go way, way back. We've served on not only on Plutus.

[Doug]

Foundation, but also prison chain gangs together.

[Joe Saul-Sehy]

On Plutus found panels, not to mention the. 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 going to 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. You don't pay a dime for this. Goodness. We're going to say hello to them and then we are diving into your best, your worst, your ugliest tax software that can really take a toll on you. I mean, between minimum payments and interest rates, it's really stressful and at times it feels, and I've been here like you just can't get ahead. Well, Navy Federal Credit Union understands debt's a huge stressor and they're here to help. Navy Federal Credit Union has all the financial tools and resources you need to dominate debt. Right now, Navy Federal Credit Union is offering a 0% intro APR on credit card balance transfers for 12 months. Here's the way. Use that stackers. First of all, you create your debt payoff strategy. You figure out exactly how that's going to help you. Because a 0% transfer for 12 months can save you a ton, but make that work for you. Plus you can get $250 when you spend 20$500 in your first 90 days on a cash rewards or cash rewards plus credit card again needs to be part of the overall plan. Don't let debt drag you down. Visit navy federal.org to start dominating debt today. Navy Federal Credit Union Our members are the mission Navy Federals insured by NCUA after the intro rate expires. Variable APRs are 14.9% to 18% based on creditworthiness. Rates are subject to change. ATM fees for cash advances are up to $1 at non Navy Federal ATMs. Small business owners State Farms there with small business insurance to fit your specific needs. Whether you're starting a new venture or growing an existing one, State Farm helps you choose the right coverage to protect what matters most. Working with a local State Farm agent helps you understand your coverage options, offering local support to help you achieve your goals. Focus on turning your passion into a thriving business, knowing your insurance can change as your business grows. Stay Farm here to help you succeed with your business like a good neighbor. State Farm is there and I'm super happy he's here with us getting the band back together. Eric Rosenberg from the college Investors here. How are you, man?

[Eric Rosenberg]

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.

[Joe Saul-Sehy]

Yeah, what a flex. Just super, super flex. Three quarters of the people are just raising their fist, you know.

[Eric Rosenberg]

But remember all of you people that it costs a lot to live here.

[Joe Saul-Sehy]

That is true. Yes. I'm paying for California. The land ain't cheap.

[Eric Rosenberg]

Yeah, the sunshine Tax.

[Joe Saul-Sehy]

Well, speaking of tax, that's the bummer about why we're talking to you is this tax time. We're going to talk over the next several minutes about all the different types of filers. We're going to talk about people that should be doing free filing. We're talking about for entrepreneurs, people that have crypto investors, all different types of people. But let's start off with just the overall winners. You, Eric, took a deep dive like you guys at the College Investor do every year. And really the difference in software, let's, let's start here. Who should use software versus who should use a pro? Or are those two continuing to kind of meld together?

[Eric Rosenberg]

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. In general, I'd say most people, if you're comfortable using a computer, if you can do online banking and email, 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.

[Joe Saul-Sehy]

Probably could be okay, yeah, maybe if.

[Eric Rosenberg]

You'Re talking to your grandparents or your parents, they, I don't know how old you are. And they, 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 with the in person accountant. When we get into people with more complex taxes as we'll dive into some of these tax apps, most of them can handle even the most complex things. 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 your money, 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, personal finance is personal. It's up to you how you want to spend your money. For me, I think one of these apps that's more affordable is totally good, it's totally sufficient. And if you're a stacking Benjamin's 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.

[Joe Saul-Sehy]

Well, and what's wild about these online options, Eric, you guys point out they get better every year, but there's a portion of our audience that is listening going, okay, just tell me which one's best. 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 fabric than just one size fits all.

[Eric Rosenberg]

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 college investors. 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 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 and really anywhere, 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.

[Joe Saul-Sehy]

All the years you and I and Robert and I have been doing this, TurboTax has been the number one, the granddaddy, but also the best. Even though last year Robert had a bunch of consternation and problems with TurboTax that have continued. He also said that 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?

[Eric Rosenberg]

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. TurboTax does make that the easiest. But 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's something at College Investor and anyone I work with. When you go into an experience, you want to know what you're going to pay up front. And you know, we're stuck with like the phone companies that you sign up and you know, they say it's going to be 49.99amonth, but then there's like $800 in fees on the end. With tax software it shouldn't be that way. Well, with any product really it shouldn't be that way. But with tax software, when you sign up, you might click a link that says start here for free and then you get through all the buttons and at the end it's like you owe $189. We don't like that kind of surprise.

[Joe Saul-Sehy]

So Turbotech 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 going to have to pay for this. And now you've already invested a bunch of time and energy. I mean, you kind of feel like a prisoner, right?

[Eric Rosenberg]

So that's why we have a new best overall, 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 based on price and quality, 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. They're one of the big ones. The only thing that I really don't like is that they have Free in the name because it's not really free. They're going to charge you something, but it's a heck of a lot less than TurboTax for the average person. The only person who will be able to truly use Free Tax USA for free is someone who doesn't have a state return.

[Joe Saul-Sehy]

Right? That'll be me in Texas, right?

[Eric Rosenberg]

Lucky you. No state income tax down there. But they get you somehow, the property taxes and sales taxes, right? They get us all somehow.

[Joe Saul-Sehy]

Yeah, but you guys wrote you can upgrade to get technical support with the app for $8. 7, 99 and support from a tax professional at $40. 39.99.

[Eric Rosenberg]

Yeah, and if you do that through something like TurboTax or H& R Block or Tax act, there are three of the big incumbents in the industry. You're going to 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 someone who has maybe a bank account, interest and an investment account and a kid or two, maybe a house, what you'll pay with Free Tax 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, which most of us are not, 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 going to be that significant. 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.

[Joe Saul-Sehy]

That is the max.

[Eric Rosenberg]

So it doesn't mean 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. So that's why we picked Free Tax USA this year. The company owns multiple brands. I think Taxhawk 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 Free Tax USA feels easier to remember. But it's a good, good choice if you have relatively straightforward taxes and you want to do it the cheapest way possible while still paying for a more premium service. That's our top pick.

[Joe Saul-Sehy]

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 when it comes to TurboTax, the number two pick, Eric, that really is the difference is that all that stuff can be imported. So back to what you said originally, TurboTax. Second, because of the slickness of what.

[Eric Rosenberg]

You get, I'm assuming 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 want to do it myself. I want to use TurboTax because it's the big one. I said, great. And at the end when the bill popped up, I didn't think I paid, would 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. 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, it's easy to make that mistake. That's really the big drawback 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. 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.

[Joe Saul-Sehy]

Yeah. It's really up to the user. Right. Why is H and R Block your second runner up?

[OG]

Yeah.

[Eric Rosenberg]

So H and R Block has just about all of the same bells and whistles as you get from TurboTax. It's typically a tidbit cheaper, 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. You can just download the PDF, drop it into the H and R Block website and it'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.

[Joe Saul-Sehy]

That'S a great one.

[Eric Rosenberg]

You should do that. I can read your PDFs now. There's no reason a software company shouldn't be able to implement that. But surprisingly the ones that really do it are TurboTax and H& 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's on the edge of do I go with an in person accountant or do I do it myself? 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 it's 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 Turbo Tax and actually Taxact just launched one of these this year. You can pay extra to have help from a CPA or a tax professional. Licensed tax professional. Not always a cpa, but they're always licensed.

[Joe Saul-Sehy]

Sure. Like an enrolled agent.

[Eric Rosenberg]

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 forgot the exact term, what they call it. Basically hand off your entire tax return. So you just upload all your files, drop them in an 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, maybe you're not the grandparent who's afraid of computers, but you're the, the parent that's on the edge. 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 want to do it yourself or pay someone. This is really, I think, the best starting place for that audience.

[Joe Saul-Sehy]

What was 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. 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? And then second, if it's not Free Tax usa, which app should those people use?

[Eric Rosenberg]

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. There's also an IRS free file program you can go to. 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 because then you're gonna have to retype all your information later and it's a big hassle. 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 Now. Cash App. You guys probably know from Cash App you can use to send people money. It's like Venmo or PayPal. It's owned by Square or Block Inc. Net is their company name. They're the payment processor. You know, the little squares that you use to pay for 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. 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, it's not the best choice. 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, 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 have two state returns to file that you wouldn't qualify. And that's for any two state situation. If you are average though, if you've lived in the same state all year and have pretty typical taxes, you can use it. It doesn't cost anything. A new one to me this year that is also totally free is Chime taxes. Chime is the bank account provider.

[Joe Saul-Sehy]

Yeah, right.

[Eric Rosenberg]

Free free checking and savings and the credit card that has no interest or fees pretty much. There's always asterisks, pretty much. But typical users, not going to 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. If you like Chime or if you are interested, that's another route to get totally free tax filing.

[Joe Saul-Sehy]

Well, I know that historically like IRS free file and get your refund, these have 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. You're not going to go to these other places and be able to file for free, right?

[Eric Rosenberg]

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. Which is pretty sweet. Who doesn't like having more money?

[Joe Saul-Sehy]

Well, here's one that our mutual friend 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 collegeinvestor.com so number one, a lot of student loan borrowers. But actually what I was referring to is this winner. He really likes TaxSlayer in a lot of ways. Eric.

[Eric Rosenberg]

Yeah, so Tax Layer is a standout for a handful of reasons. They for me for a lot of years were kind of the big number four. So the big three were always TurboTax, H&R block and TaxAct and tax layer. I started to notice maybe a decade ago. I think the first place that it really caught my eye was on Reddit. I was, I'm a Reddit guy. I won't tell you my username because that's what Reddit's all about, right. And I was cruising the personal finance and tax subreddits 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. It's a lot cheaper than the bigger competitors and it works just as well. 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 TaxAct. So it's quality wise, worth being in the top three, four or five options. But the pricing is a little better. So that's a reason. We 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 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.

[Joe Saul-Sehy]

If I am an investor and I've got maybe lots of different stock positions, what's my best choice for filing?

[Eric Rosenberg]

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 a lot of transactions. So if you have a lot of investments in general but you're not buying and selling a lot, 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 see, you, Schwab, Fidelity, Chase, any of the big brokerages, you type in your information and your login information, it will automatically download all of your transactions.

[Joe Saul-Sehy]

It's that import feature that wins the day.

[Eric Rosenberg]

It's just if you're an active trader and you have a thousand trades over the year with just about everyone else other than probably H and R Block, you're going to be sitting there typing in a thousand transactions. And if you are the kind of person who's trading that much, spending, you know, two or three days, typing in line by line, every trade is probably a deal breaker for that crowd. It's probably worth paying $100 more, $150 more to just click and import.

[Joe Saul-Sehy]

Do they win for crypto as well?

[Eric Rosenberg]

Yeah. So with crypto it gets a little more complicated, 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 it right into TurboTax or H& R Block or most of the others. But if you are a crypto nerd 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. You'll need an intermediary crypto tax software. There's two that I really like. One is called Koinly 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, they connect to almost every exchange, hundreds of them with APIs if they're available. So you might need to be a little bit more techy. But you're probably not doing crypto through all these exchanges if you're not already a little more techy. So if you're that person, you have a lot of crypto stuff going on, you're probably going to need to pay additionally for something like cointracker or coinly, and they will create the forms that you can then import into TurboTax or another app.

[Joe Saul-Sehy]

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 real estate landlord. Which one of these programs do I turn to first?

[Eric Rosenberg]

Yeah, so we pick Tax Slayer for landlords. The pricing is reasonable. We were already talking about reasons we like Tax Slayer 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 something like QuickBooks or Xero or whatever you use. There's lots of specific apps just for landlords. 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 is a great place to pick up and get your stuff all entered and get an accurate tax return.

[Joe Saul-Sehy]

And what's amazing to me, and it felt a little random as I was reading through these, 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?

[Eric Rosenberg]

So for landlords, depreciation is going to be really important. We pick Cash App Taxes for side Hustlers as a favorite. And 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. But the typical side hustler, maybe you're an Uber driver or a doordasher, or you sell some trinkets at a local farmer's market or artworks on Etsy, 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. 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. 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 want to spend an extra $120 on your taxes when you could do it for free even if it takes a few more minutes.

[Joe Saul-Sehy]

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 kind of like you flipped because then, then you've got tax layer as the runner up. So it sounds like if you're somebody that has the side hustle of real estate or any other side hustle, those are your two go tos. Like those are text layer and cash app.

[Eric Rosenberg]

Unless you like one of our top overall picks more.

[Joe Saul-Sehy]

Absolutely. Now let's say then, Eric, that I want to work with a human, but I want to do it directly through the computer. You guys looked at that category?

[Eric Rosenberg]

Yeah. So for virtual tax prep, that's what we called it, 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 when we were all stuck at home, they were pretty innovative. They were basically the zoom of tax prep at the time. They were, because 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. So that's why we picked them. They were really a leader in 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 modest upgrade and work with someone and have a video meeting just like you're watching us here on, on YouTube.

[Joe Saul-Sehy]

Right. And that's, you know, for people that need that extra, I don't know, 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.

[Eric Rosenberg]

Yeah.

[Joe Saul-Sehy]

Every year these are our most popular show notes stackers. So head to stackingbenjamins.com and you'll find the show notes for today's episode. But if you want to go directly, there's, I think you guys, 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.

[Eric Rosenberg]

Yeah. If you Google or whatever search engine you like, if you duck, duck go it. Is that a verb now? If you duck, duck go it, you can type in the college investor best tech software and it'll come up towards the top.

[Joe Saul-Sehy]

And I should even laugh because I use Bing and everybody makes fun of me for Bing.

[Eric Rosenberg]

Yeah, I don't Bing, but I do duck.

[Joe Saul-Sehy]

Duck.

[Eric Rosenberg]

Go some. I've been de googling my life a bit, trying to get a little more privacy focused. And one way I'm doing that is I don't only use Google to search now.

[Joe Saul-Sehy]

Well, and it's funny, I use Bing because they pay me for search. Like, I end up getting some money for search. Like, what's, what's, what's wrong with that?

[Eric Rosenberg]

Are those two cents every couple of days adds up. Over 20 years, you're going to make $100.

[Joe Saul-Sehy]

Oh, it totally is. It's not. It literally is like $35 a year. But hey, you know, like, you, you and I, I think search way more than the average person. Right? We're constantly on there. Eric, man, thanks for helping our stackers navigate tax day again. I super appreciate you and the whole team over there at the College investor.

[Eric Rosenberg]

Yeah, thanks for having me back on the show. And if you want to connect with me directly, go to eric.money in your browser. No dot com. Just eric dot money. And I'd love to connect with you.

[Joe Saul-Sehy]

And we'll have Eric's go to link on our show notes as well, everybody.

[Eric Rosenberg]

Bye bye.

[Doug]

Hey there, Staggers. 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 at 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. How about a trivia question? What book will 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.

[Joe Saul-Sehy]

Today's show sponsored by Strawberry Me Stackers. All right, everybody, let's talk careers. You know, you work hard, you bring in a paycheck, maybe even contribute to your 401k. Like a responsible adult gold star for you. But here's the thing. Making money is great, but making the right moves to actually grow your career and earn more, are you doing that because, let's be honest, hoping your boss finally notices you and hands you a raise. That is not a plan. That is a gamble. And unless you're the type of person who gets excited about betting their retirement on meme stocks, you probably Want a better strategy? I certainly do. I have a coach, Mary Lou, that I meet with every Monday morning. And Mary Lou and I lay out my week. We talk about doing the things that are important to my family, that are important for my health and the things that are important for financial literacy and stacking Benjamins and the intersection of all those things. And that's where Strawberry Me career coaching can help you. They'll match you with a certified career coach, somebody who knows how to help you get ahead. Like my coach helps me negotiate better pay and actually make smart money moves. So you're not leaving money on the table. You've heard me talk about this before. The key is to have people around you, smart people around you who hold you accountable to getting those things you say that you want for yourself. If you're anything like me, you've been meaning to quote, update your resume for like the last five years. I remember what Mary Lou said. Are we going to keep talking about this book or you finally going to write it? And I'm very proud of Stacked. But without Murray Lu, I would have never had Stacked. Your career is your biggest financial asset. It's time to start treating in that way. When I started treating it that way. Things change. It can be the same for you. So here's the deal. Go to Strawberry Me. It's Strawberry Me stacking and you'll claim your 50 credit that strawberry Me stacking because maximizing your earnings is just as important as maximizing your investments. Strawberry Me does not facilitate or provide healthcare services. Please consult with a healthcare professional. But guys, let's get smart people around us, shall we?

[OG]

I can say to my new Samsung Galaxy S25 Ultra, hey, find a keto friendly restaurant nearby and text it to Beth and Steve. And it does without me lifting a finger so I can get in more.

[Eric Rosenberg]

Squats anywhere I can.

[OG]

1, 2, 3. Will that be cash or credit?

[Joe Saul-Sehy]

Credit.

[OG]

4 Galaxy S25 Ultra the AI companion that does the heavy lifting.

[Eric Rosenberg]

So you can do you get [e-mail] compatible with select apps.

[OG]

Requires Google Gemini account. Results may vary based on input. Check responses for accuracy. Your data is like gold to hackers. They're selling your passwords, bank details and private messages.

[Eric Rosenberg]

McAfee helps stop them.

[OG]

Secure VPN keeps your online activity private. AI powered text scam detector spots phishing attempts instantly.

[Joe Saul-Sehy]

And with award winning antivirus you get.

[OG]

Top tier hacker protection. Plus you'll get up to $2 million in identity theft coverage. All for just $39.99 for your first year visit McAfee.com, cancel anytime terms apply.

[Doug]

Hey there, Stackers. I'm guy who loves funny hats and guy who likes to be here. Oh, I like it a lot. Joe's mom's neighbor, Doug. I've been kind of misquoting lines from a best selling 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. 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 Dreisel. 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.

[Joe Saul-Sehy]

Oh, come on.

[Doug]

Joe and OG oh, should have seen.

[Joe Saul-Sehy]

That one coming from a mile away.

[Doug]

That's a high compliment. It's as good as I can make it. Thing One and Thing Two.

[Joe Saul-Sehy]

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 thought it'd be fun if you're a twin, to wear a Thing 1, Thing 2 T shirt. Neither would I want anything to do with that. They were like, nope, we're doing it. So Cheryl and I bought them.

[Doug]

Nobody wants to be Thing Two. That's the dumb one.

[Joe Saul-Sehy]

Well, Thing Two is kind of the crappy one, right? The crappy one? No, no.

[OG]

Down to 12. Doug.

[Doug]

It'S just your age is eroding by the minute.

[Joe Saul-Sehy]

I shouldn't have had coffee before we did that. Big thanks to Eric Rosen.

[OG]

Coffee was the problem.

[Joe Saul-Sehy]

Yeah. There's a new sheriff in town. OG Free Tax usa.

[OG]

Free Tax usa. Yeah. Why is it so difficult to have pricing upfront?

[Joe Saul-Sehy]

Like, just don't understand either.

[OG]

Tell me. Just tell me what you're going to tell me and then tell me. And then tell me what you told me. Like, make it really simple. It doesn't have to be complicated.

[Joe Saul-Sehy]

It is interesting how we kind of think of this as one size fits. All right? And as Eric explained, it truly is, isn't. If you're somebody that really, really wants the help of an enrolled agent, H R Block has done the best job of putting those together, their enrolled agent community and the ease of the software. 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're looking for.

[OG]

Yeah. Pretty quickly you get to. And then you should just have a CPA that does them.

[Joe Saul-Sehy]

Yeah.

[OG]

There's a pretty quick acceleration from, you know, and then maybe it drops off. Right. Like during different seasons of your life. Just out of 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, rmd, maybe back to.

[Joe Saul-Sehy]

Right back to the software.

[OG]

Software. Yeah.

[Joe Saul-Sehy]

But I think certainly if you're somebody that is going to do what Grant Sabatier suggested on Monday, which is you're going to go into entrepreneurship, that business starts to grow. Oh, gee, there's so many opportunities. There's so many tax planning opportunities. I think that having those smart people in your corner pays for itself, to your point, very quickly.

[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 cash flow planning, your tax planning, payroll savings, investing, like all that sort of stuff dovetails together. 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. And if you over contribute 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 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. 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 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 going to all play together to make good Decisions, you know, leading into your tax filing season of, of early 26.

[Joe Saul-Sehy]

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 going to be in the first place?

[OG]

Yeah.

[Joe Saul-Sehy]

Is it going to 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 tech software with a pro, like, I already know where these pieces fit and that I have have a fit.

[OG]

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 20, 25 right now, and you're thinking tax planning for this tax year 25, and you know, hey, there's no chance I'm going to be taking anything other than standard deduction. 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 a receipt of this. I know I'm not using this in the future. I know I'm not going to 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, now versus I'm planning on making a big donation this year. Now I need to see how that factors into my tax deductions and my 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, 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.

[Joe Saul-Sehy]

And both ways a big win.

[OG]

Yeah, absolutely.

[Joe Saul-Sehy]

Both ways a big win. Big thanks to Eric for hanging out we got an interesting headline today. Hello darlings.

[Eric Rosenberg]

And now it's time for your favorite.

[OG]

Part of the show, our stacking Benjamin's headlines.

[Joe Saul-Sehy]

Our headline comes to us from the Wall Street Journal. This is written by Spencer Jacob. Stocks have a big expensive problem. Spencer writes. He says strange times are afoot in the investing world. Your portfolio probably isn't ready for them. The US Stock market is the big dog of 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, Clifford at two thirds of the global market value that outweighs America's 1/4 of the world's economy and 4% of the world's population. But the US tail has usually wagged the global dog. Recently though, that relationship has broken down. Could signal an investing upheaval and very poor returns for big US stocks in coming years. Analysts at Data Trek Research note that the usual correlation between the main US benchmark, the S&P 500, and the MSCI EAFE, which is an index of non US developed stocks, has historically been a very high 0.83. Over the past 100 days it's been 0.54. And he talks about, oh gee, how that is bigger than it sounds.

[OG]

Over the past three whole months, your long term decision making should be based on the last 100 trading days.

[Joe Saul-Sehy]

We've seen stock market declines OG we've.

[OG]

Seen some increased volatility.

[Joe Saul-Sehy]

Yeah, what's going on here?

[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. 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. 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 going to be happen. 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 might have been international or small companies. And you're back to where you want to be.

[Joe Saul-Sehy]

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 the hell knows, 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. 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 want to play the sector game. You don't want to 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, 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.

[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.

[Joe Saul-Sehy]

Years, two and a half, That's a very long decline.

[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 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. It's already been 15 months since his second car accident. You know, it's like it's. Time is just 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 rearview mirror, it's not that long ago. But there's no way to know when is the top and when is the bottom. 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. You'll be all right.

[Joe Saul-Sehy]

Yeah. This wouldn't be a media piece without predictions in an OG which always make me laugh because they're always wrong. However, what is interesting is this group of research affiliates looked at valuations and their prediction, which is not worth the paper it's written on. But I do find this interesting. We talk about rotation and buy and hold and don't be a sector investor. 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 u. S. Developed markets, 10% topping that emerging markets, emerging markets value specifically at 10 and a half. Is any of that worth anything? No, but it does go back to what we've been talking about, this reversion of the mean and don't do the bet. Don't bet.

[OG]

I mean, it's just a rubber band snaps in one direction, comes back the other man.

[Joe Saul-Sehy]

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 sharing some brilliance or air quotes Brilliance. Today I'm going straight up. YouTube video, though. This is not a short. This is a YouTube video that I found. Yeah, you think we're gonna hear brilliance or air quotes Brilliance, since we're talking.

[OG]

About taxes, I'm gonna. I'm gonna err on the side of this is. This is gonna be great. Yeah. Whoa, hot take.

[Joe Saul-Sehy]

Well, this is. This one actually is not going to be about taxes. I'm going to go with the theme that Spencer Jacob was on, the Wall Street Journal writer 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. This YouTube creator is instructing people on how to make a bunch of money with crypto meme coins.

[E]

Rug 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 sols for the initial pump. Here's how it works with a real life example, Binance's 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 sols in one purchase. Because of this large buy, the coin got a king of the hill spot and free advertising on the main page. Random unsuspecting traders saw the coin associated with trending news and 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 Raydium, but instead it was dumped, earning its creator 7.6 Sol or $1,000 in just one minute. 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 this simple tact. Be careful and always check coins for obvious rug pull signs. Subscribe if you found this useful Not.

[OG]

A person that is 100% some crappy AI generated BS commentary.

[Doug]

That AI invented several words for that piece I've never heard before.

[OG]

I didn't.

[Joe Saul-Sehy]

Well, I don't care about any of that.

[OG]

What I care about creator. It's not a creator, it's a computer program.

[Joe Saul-Sehy]

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.

[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 going to keep putting Money in my 401k in my Roth and my brokerage account, I'm making money in other people's stupidity.

[Joe Saul-Sehy]

I love the idea of making money off other people's greed. I mean, I love what that thing said about there's several red flags and people are so excited about the new meme coin that they just jump in thinking that all this excitement equals some big gains. There's huge red flags all over these projects. And yet how many times have we reported on stories where people just lose their ass on the latest coin? You know, it's funny. You can't even find the Haktua girl now. You can't find her. She's. I went looking for her podcast, man. She is gone. Like, she is gone.

[OG]

Well, yeah, she got like a hundred million dollars. She scammed everybody out a bunch of.

[Joe Saul-Sehy]

Money since the Rug Pull. Right?

[OG]

Changed her name.

[Joe Saul-Sehy]

So disturbing.

[OG]

Rug Pull Girl.

[Joe Saul-Sehy]

So disturbing. When you see people that are looking for the shortcut and end up losing tons of cash again because there's professional.

[OG]

Too much 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 them to go away?

[Joe Saul-Sehy]

Please, God, go away.

[OG]

Yeah.

[Joe Saul-Sehy]

Well, it's a great story. I don't know. 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. All right, let's go out to the back porch and find out what's going on our community before we say goodbye. Doug, what do we got on tap today?

[Doug]

We had. This was a fun one. And I know that you're familiar with this, Joe, but I'm going to 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.

[Joe Saul-Sehy]

It's so funny. Hey, Doug, let me throw it to you so you can throw back to me.

[Doug]

Yeah.

[Joe Saul-Sehy]

Yeah. Watch this tennis match here. Yeah, I did. I got a great note from our friend Manoj. 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. I believe they went to one in Portugal and 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 needed 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. Did you attend the stacking Benjamin's meetup? And he said, yes. And it was our mutual friend Sterling Cog. We're getting people together at our meetups. People Helping people, making the friendships blossom. And stacker saving stackers money. That is so funny.

[Doug]

I want to know more about the dryer. Like manaj, like let everybody know in the basement. Did the dryer work? Is it. Did he leave the lint in it? Did he clean out the lint catch before you bought it?

[Joe Saul-Sehy]

All Doug wants for you is to hang Sterling out to dry.

[Doug]

I mean, or she could be like, oh, it was sterling clean. It was amazing. And I got a great deal on it. And in fact, Sterling just gave it to me for free since we were both stackers. We don't know. I just need more to this story.

[Joe Saul-Sehy]

That's what should have happened. Sterling, you should have given it to her for free. I mean, really, once you knew that it was manoa, she should have given it to her for free.

[Doug]

Stacking Benjamin's way. We give the show to you for free. So you should give your dryer away for free.

[Joe Saul-Sehy]

Follow our lead. Thanks for the note, Manoj, and it was great hearing from you again 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 met at a microbrewery that was a former bank. And there's a room you can have your meetup in. That's the bank vault room, which is pretty cool. We didn't do our meetup there, but maybe we will this time. Stay tuned. If you don't get the 201, you want to make sure you get that so you know where our next meetup is going to be. All right, Doug, I think that's going to do it for today. Thank you everybody for hanging out with us. 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 do the top three. What are the three things maybe we should have put on our to do list during today's episode?

[Doug]

Well, Joe, first, take some advice from Eric Rosenberg. 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 Seuss book. Like, how come I've never read this goodness before? 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 worse to live by right there. We just did that, didn't we? Of course we did.

[Joe Saul-Sehy]

Yeah.

[Doug]

Thanks to Eric Rosenberg from the College Investor for joining us. You'll find the College Investors tax guide atthecollege investor.com or we'll have a link in our show notes. 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 stackingbenjamins.com taxguide for details. This show is the property of SB Podcasts, LLC, Copyright 2025, and is created by J. Joe Saul Sehi. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello.

[Joe Saul-Sehy]

Oh, yeah.

[Doug]

And before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug. And we'll see you next time back here at the Stacking Benjamin Show. Sa.

[OG]

Don'T do a lot of movies, don't have a lot of time, but happened to catch this one on Apple tv. Plus, is that the correct, I think.

[Joe Saul-Sehy]

So phraseology for what that is pay for version?

[OG]

My oldest wasn't feeling very well. The other one was on, you know, staying at somebody else's house. Listen, Caroline were, I don't know, doing something. So, anyways, we sat and watched this movie called the Gorge on Apple tv. Plus.

[Joe Saul-Sehy]

I have new orders that require.

[Eric Rosenberg]

Me to go dark for at least.

[Joe Saul-Sehy]

A year, maybe more.

[Eric Rosenberg]

A special assignment in an undisclosed location.

[E]

As an elite sniper. Are you presently under any private or military contract?

[Eric Rosenberg]

No, there's not a lot of reasons.

[Joe Saul-Sehy]

For me right now. What if I gave you a reason?

[OG]

There she is.

[Eric Rosenberg]

West tower observation post. Your home for the next 365 days. There is no outside communication here.

[Joe Saul-Sehy]

What's that on the other side?

[Eric Rosenberg]

That is east tower. Contact with the other side is strictly forbidden.

[Doug]

So what's the mission? To keep people from going in the gorge?

[Eric Rosenberg]

No, you need to stop what's in.

[E]

The gorge from coming out.

[Doug]

What the hell is that?

[Eric Rosenberg]

The gorge is the door to hell. And we're standing guard at the gate.

[OG]

So that's the intro part of the show.

[Doug]

Miles Teller sounds like a laugh a minute.

[Joe Saul-Sehy]

Wow.

[OG]

It sounds a little bit more intense than it is. It's PG13, so there's not too much. The three major actors in this movie. Sigourney Weaver, probably the biggest name. Miles Teller most people are familiar with, and Anya Taylor Joy is the other lead actress actor in this movie. 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 going to anyway. 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 it's the gateway to.

[Joe Saul-Sehy]

Hello? Gee, I heard the trailer. It's the gateway to hell.

[OG]

It is the gateway to hell. Interesting twist. Something happens, they find themselves in the gorge. So they, they have to escape. And kind of, kind of an interesting twist on what actually it is. You know, thumb three and a half ways up. I mean, fun popcorn movie three and a half ways. Yeah, three and a half ways like that. Like not all the way.

[Doug]

You're pointing at like a 45 degree, maybe 60 degree angle. Okay.

[OG]

Like 70, 80% good popcorn movie. PG 13. Not a ton of blood and guts. Kind of fun because they all have machine guns, they jump out of airplanes, sniper shots, whatnot. Little love story in there and, and chaos. So kind of fun.

[Doug]

This is a love story between Miles Teller and Sigourney Weaver.

[OG]

No, no.

[Doug]

Could be like a, a May December kind of thing.

[OG]

No, she's the one that gives him the assignment.

[Doug]

Okay.

[OG]

Pretty simple to follow this along. The roadmap is pretty well worn on this type of storyline. But if you're bored on a Tuesday afternoon and you don't have anything else going on, flip it on Apple tv.

[Doug]

If you want twists and turns and stuff you just don't see coming. Love is Blind Season eight, baby.

[OG]

Ooh, that is right up your alley.

[Doug]

Oh yeah, that's hard hitting stuff.

[OG]

But I liked it. Alex liked it. Fun to watch a little zombie ish.

[Joe Saul-Sehy]

You know, it sounds fun. Sounds like a campy ish, fun movie.

[OG]

I mean, as fun as machine guns shooting zombies, trying to escape from the gorge.

[Joe Saul-Sehy]

Exactly what you're looking for.

[OG]

There's lots of explosions, there's sniper shots.

[Joe Saul-Sehy]

Who knew you'd like that one. Yeah, you're playing against your type.

[OG]

The opening scene is a sniper shot and. And then jumping out of airplanes. And you know what?

[Joe Saul-Sehy]

Did you start crying, like, 25 seconds in?

[Doug]

Were you crying out of joy?

[OG]

No. So 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.

[Doug]

You ever. 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 Primeval? The Dark.

[OG]

So you asked me this, generally speaking, every four to seven days.

[Eric Rosenberg]

Yes.

[OG]

And I have not, because don't have a lot of time.

[Doug]

It's my subtle way of saying, watch it, damn it, because you will like it.

[OG]

I will for sure.

[Joe Saul-Sehy]

Maybe season two, the Night Agent. It was really good. Season two.

[OG]

Oh, you know, I started watching that. 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.

[Joe Saul-Sehy]

No, season one, he works in the basement of the White House, and he's got to monitor this phone that doesn't ring.

[OG]

Yeah. And then it rings, and it's something about a bomb in a train or something, right?

[Joe Saul-Sehy]

No, it's these people call in, and there's.

[OG]

That's right.

[Joe Saul-Sehy]

And there's people at their house, and they got to try to get them.

[OG]

I started watching some of that. Is it good?

[Joe Saul-Sehy]

Yeah. Doug didn't like season one. I like season one a lot. And then season two, I thought was even better than season one. I very much enjoyed season two.