Let’s be honest: taxes feel like that thing you’re supposed to understand but somehow never learned, and now you’re too embarrassed to ask.
Joe Saul-Sehy, OG, and Neighbor Doug welcome Hannah Cole—artist-turned-tax-pro and author of the brand-new book Taxes for Humans—to finally explain taxes in language that doesn’t require a CPA license to understand. Hannah’s built her career translating tax code for freelancers, side hustlers, and small business owners who just want to know what they can deduct, what’ll get them audited, and how to stop drowning in shoebox receipts.
She breaks down the real difference between a legitimate business expense and wishful thinking, how to track startup costs without losing your mind, and why the bookkeeping system that works is the one you’ll actually use (spoiler: it doesn’t have to be fancy). Whether you’re launching a side gig, running a creative business, or just trying to keep the IRS from ruining your holiday season, Hannah’s got the roadmap.
Then Joe and OG shift gears to tackle the “AI bubble” conversation everyone’s having—is this tech hype justified, or are we watching 1999 all over again? They break down how to think about market froth without panicking, why smart investors don’t build their strategy around TikTok prophets predicting doom, and how to prepare your portfolio for volatility without making fear-based moves.
Plus: Doug delivers trivia about Richard Pryor’s Blazing Saddles days, because even tax talk deserves a palate cleanser.
What You’ll Walk Away With:
- Tax basics explained in actual human language (finally)—what counts as a deduction and what’s just wishful thinking
- How to set up simple, sustainable bookkeeping systems for side gigs or small businesses that you’ll actually maintain
- The smartest way to track startup expenses without drowning in receipts or spreadsheets
- Why the IRS isn’t as scary as you think when you’ve got your basics covered
- How to think about AI market hype without getting swept up in either the euphoria or the panic
- Smart strategies for preparing your portfolio for volatility without making emotion-driven decisions
- Why the right tax and investing systems buy you back time, creativity, and peace of mind
This Episode Is For You If:
- You’ve been winging it on taxes and know you’re probably missing deductions (or making mistakes)
- You run a side hustle but have no idea what you can actually write off
- Tax season makes you anxious because you’re never sure if you’re doing it right
- You’re hearing AI bubble talk everywhere and wondering if you should be worried about your investments
- You want systems that are simple enough to actually follow, not perfect enough to abandon by February
Before You Hit Play, Think About This:
What’s the tax mistake you wish you could warn your younger self about? Drop it in the comments—we’re all learning here, and sometimes the best lessons come from what we got wrong the first time.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Monday Mentor: Hannah Cole
Big thanks to Hannah Cole for joining us today. To learn more about Hannah and listen to her podcast, visit sunlighttax.com. Grab yourself a copy of her book Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Our TikTok Minute
Our Headline
- The ‘First Year of Retirement’ Rule (Kiplinger)
Doug’s Trivia
- What film did Richard Pryor co-write and star in with Mel Brooks that’s ranked #8 on the AFI’s list of greatest comedy films?
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Other Mentions
- Startup Expenses: A Perk for Your New Business (Sunlight Tax Podcast)
- Get your Free Visual Guide to Tax Deductions (Sunlight Tax)
- Benjamins After Dark (BAD) meetup groups
- Personal Finance Guides to Help You Make Smarter Money Moves
Join Us Wednesday
Morgan Housel will teach you the art of spending money.
Written by: Tina Ichenberg
Miss our last show? Listen here: Board Games That Make You Smarter With Money (Without Feeling Like School) SB1767
Episode Transcript:
Joe: Happy Cyber Monday. Guys. I’m surprised I could get you on the microphone when there’s
Doug: deals galore online. Yeah, I, who knows, like when are we supposed to jump on the Black Friday stuff or wait for the Cyber Monday stuff? I just can’t handle all of this uncertainty. Just tell me when I’m supposed to buy stuff.
Joe: It sounds like it’s all the time. It’s like they say here in Texarkana all y’all, it’s all y’all
Doug: time. And remember back like three weeks ago when the early Black Friday deals were getting released in the beginning of November. Like this is out of control.
Joe: It’s gonna be July next year. They’re gonna have Right.
Doug: Black
Joe: Friday in July. Exactly.
Doug: Yeah. But I, Amazon kind of does that.
Joe: I thought I’d celebrate the start of December for our every Monday Salute to the Troops by, uh, bringing out my Christmas mug, which I always thought was really neat. But there’s just something a little weird and creepy about drinking outta Santa’s pants.
Like, just for people, for people that can’t see my mug, it is Santa’s pants. I’m drinking outta Santa’s pants. I dunno what that means. I don’t know what it says.
Doug: That just made me laugh, like, real laughter.
Joe: Let’s raise our mugs, guys. Earn this place. Let’s raise, let’s raise Santa’s ass. It’s OG doesn’t even know what to do.
It’s like I got no idea’s. Shaking
Doug: his head in grins on.
Joe: Be on behalf of the men and women. At Navy Federal Credit Union who serve our veterans and our active duty troops and the men and women making podcast in mom’s basement, we wanna salute those troops and those veterans thanks to the veterans for your service.
Thanks to the troops for keeping us safe. Another big holiday weekend. This time we were out playing. Let’s go stack some Benjamins together now.
Doug: Thanks everybody. Cheers. My mug’s Christmasy. Looking until you realize it’s from a distillery, which is still Christmasy.
Joe: Yeah, that’s Cheer baby still is right there.
If you gotta be around the in-laws, why not get the distillery involved? All right, let’s do it. Here we go.
Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamins Show.
I am Joe’s mom’s neighbor, Doug, and does all that complex tax advice just confuse you. Do you wish there was a primer on taxes? That’s right. I said primer. Primer. No, it’s primer. We’ve gone over this already. Well sit right down, og, because on today’s show we welcome the woman who’s. Gonna share some tax tips for regular humans.
Anna Cole in our headline segment, Peter Thiel sold all of his Nvidia stock in the third quarter. Does that mean the AI bubble burst is happening? It’s happening. Plus we’ll share a TikTok minute Sure. To fill you with dread, and then I’ll counter it with some uplifting and heartwarming trivia. And now two guys.
Who are the first people you think of when you think uplifting and heartwarming just ahead of Mother Theresa. I don’t. It’s Joe and OG.
Don’t think of og. And I just slightly ahead of Mother Teresa. Not ahead of mother. I mean, you come into mind eventually, but it’s a long way after Mother Teresa.
bit: For the record. Um, I don’t know if chat GPT is wrong on this or if Doug is wrong on this. It’s a 50 50 shot here, but just for the record chat, GPT 5.1, uh, does suggest that primer is the correct usage in primer.
In what context? A basic booklet of instructions or a short introduction to a topic and chat. GT is saying Prime is primer. Primer Short eye is used. When you mean paint or a base layer chat, g PT is a hundred
Doug: percent reversed. A
bit: hundred percent wrong. Okay. All right. Yes. Well, I’ll just, I’ll have a word with Sam later and uh, we’ll fix that.
I find it hard to believe that Chad, GB t’s wrong with anything, but okay. Yeah. Right. Welcome. Right. To
Joe: Shockingly, shockingly, AI is wrong. Again, when you ask it a question, I
bit: honestly wonder if it’s ai, but it said it was on 60 minutes and maybe we’ll share it. I don’t know if we got time today. Maybe we’ll share it on Wednesday.
This, uh. What just happened? Do you hear Santa’s pants just bubble? Did you just snort into Santa’s pants?
Doug: That’s what that was. Santa’s pants just bubbled
bit: did. Somebody just did, does Santa’s pants sharp while you were drinking out of them?
Joe: I reached, I was taking a drink and I reached the part where it goes down into his leg and so it
bit: Santa just sharded while you were drinking out of his pants.
Okay.
Doug: Another high end highbrow moment from Stacking Benjamins. Wow. But 60 minutes. Anyways,
bit: I’ve got, I got a great thing from 60 minutes, uh, a little piece that maybe we can share later, maybe later this week. I don’t almost see.
Joe: Well, I gotta tell you something that is fun today that we will 100% share, and that is the gift of Hannah Cole.
She is going to talk to us about taxes for humans, you know, oh gee. Often we talk about Roth conversion strategies, the triple tax treatment of HSAs. And you and I both know there’s stackers out there that are like I was when I began at this. Like, what the hell are you talking about? I have no idea how this tax thing even works.
So we’re going to go back to the drawing board. We’re gonna take this foundation down to the studs as they say, and, uh, yeah, yeah. Here. Oh wait,
bit: different meaning Hannah. Lemme chat. GPT that one real quick.
Joe: Hannah Cole is gonna help us with that today, and I can’t wait for that because I know that when somebody finally sat down with me to talk to me about how the tax code actually worked, we literally OG just went through the two pages of the 10 40.
And then I, I knew the difference between a deduction and a tax credit.
OG: Yeah.
Joe: At first, I thought they were just kind of the same thing, but with different names, you know? Okay. It’s a deduction or it’s a credit. No, no, no, no, no. A deduction is fine. That’s good. A credit. Whole different level of good. So if you’re like, I was, we got you covered today, stackers, because nothing you need to know more for Yearend tax planning than just how this whole thing works.
So Hannah Cole joining us today. Before we say hello to Hannah, we’ve got a couple sponsors that help us keep on keeping on. We’re gonna hear from them and then taxes for humans with our friend Hannah Cole.
Hey, let’s talk not taxes, 2 0 1 or 3 0 1 or 4 0 1. Let’s talk about taxes for actual humans and the perfect woman to do that on the perfect day to talk about taxes. Cyber Monday. Hannah Cole’s here. How are you?
Hannah: I’m so good, Joe. Thanks for having me. Great to be here.
Joe: Well, I’m glad that you could be here and help our stackers with taxes 1 0 1 because all of our stackers tell us, Hannah, they wanna start a side hustle.
They wanna maybe make some extra income or maybe they’re entrepreneurs. And the thing that you know as well as anybody knows is the tax code really kinda, we hear all these things, the taxes are tough and evil and wild and impenetrable. Tell us that’s not the case.
Hannah: It’s not the case. And in fact, it’s so wonderful to realize if you.
A person who’s trying to start a side hustle that the tax code is really there for you. Like there is no better place to get easy access to the benefits of being a business than the US tax code. So even when you start something teeny tiny nights and weekends in your garage, you still count to get all the benefits of being a US business, which is pretty awesome.
Joe: So, stackers, I know we told you this in the intro to Hannah’s segment, but even if you’re not thinking about starting a business today, right now, you’re gonna wanna listen to this. You’re gonna wanna mark this episode, you’re gonna wanna come back to it ’cause we’re gonna dive in to that. And if you’re not starting a business, we’re just gonna talk a little taxes 1 0 1 for the next, uh, 20, 25 minutes.
You know, the reason I like talking to you about this stuff, Hannah, is that you and I have this shared background. I was somebody who is an English major, who I don’t think anybody would’ve thought that I’d end up being a finance guy like you of all people. You were the same. You were somebody who, what’d your parents say to you?
Hannah: Oh, you mean my dad’s accountant? Oh, it was your dad’s accountant. I thought it was your
Joe: dad. It was your dad’s accountant. Oh
Hannah: my. My parents were very encouraging to, I wanna give credit to them. My dad’s accountant said to me when I sat down across from him for the first time to do my taxes as a professional artist, when are you gonna get a real job?
Joe: Oh my God. Boy, that’s encouraging.
Hannah: I was like, you’re looking at it.
Joe: Maybe I thought it was your dad instead of your dad’s accountant. Because my, a wonderful man, but actually said to me after three years as a financial planner, so this financial planning thing, you think you’re gonna stick with it or you think it’s gonna.
It’s like, yeah, I think maybe, I think it’s going okay, dad, I think we’re gonna be,
Hannah: yeah. Well you showed him, didn’t you?
Joe: I think we’re, I think we’re gonna be fine. Well, no, the answer is no. I didn’t stick with it. I went onto podcasting at 40 years old, so, but when I made that transition, Hannah, I went from owning a franchise, so being kind of a quasi self-employed person, uhhuh to being fully self-employed then.
And I started out writing financial stuff for people. One of the first people I wrote for was this wonderful woman, Miata, aoga, and Miata, her job and her mission is to empower artists. She’s in Los Angeles. She has found that lots of artists, artistic people think, well, I’m supposed to be bad with money.
Money’s the devil. I’m not good with money. Like there is this Yeah. Stereotype among artists that you even talk about in your book. That’s not true at all.
Hannah: Yeah, it’s not true at all. I mean, the fact is that artists, frankly, because they have to be, they are so resourceful. I mean, you’d be hard pressed to find somebody who can make magic happen on a shoestring, which isn’t actually, you can make more magic when you’re beyond the shoestring.
But I mean, artists are so fired up and creative about what they wanna get done, you know, like a project. And they will just go get whatever resources they need, fill whatever holes, get whatever education in order to make some magical project happen. So I think artists, and I, I say this because I am one and because my community are creative, people we’re incredible.
We’re real like doers and, um, we make things that are invisible to people suddenly become real. I think it’s kind of magical. I think it’s amazing. And yeah, we get kind of fed this line that we’re bad at money. You know, as soon as you start to believe that yourself. You can make it come true. So it’s really important I think, that we realize like, oh, this is just another skill and I’m good at getting new skills.
Joe: And you say like any other skill when we start out. I mean, it truly is our mindset that matters.
Hannah: Yeah. I mean, if you tell yourself you’re terrible at something, there’s really good evidence. I say this, I have two daughters. Um, the math teachers are always giving this research like, do not tell them how terrible you are at math.
Do not tell them that girls struggle with math. Because if you reinforce a stereotype, even if your daughter’s about to crush it on this math exam, if you remind of a stereotype about girls in math right before she goes into the test, she’ll actually perform worse than she would have so that you actually, it actually really does matter tangibly that you remind people of how good they are.
Before they go out and try to do a thing. So I kind of carry that into the tax world too. I think it’s, it’s just as important that people are like, oh yeah, right. I’m like pretty good at learning new stuff.
Joe: But it’s funny, on Friday we did our annual board game episode Uhhuh, so I teach people board games all the time.
I will tell you the biggest problem is people tell themselves ahead of time, I’m not gonna get it. You can see them shut down immediately, like, I’m not gonna get it. I’m like, no, no, don’t try to get all of it right now. Just tell yourself that you are able to understand and if you can tell yourself that you can understand some simple rules, then you’re gonna be just fine.
I feel like taxes are kind of the same. When somebody sat me down with the 10 40 Hannah and literally went through it, we’ll go through a little bit of this today, but when somebody sat me down and told me how things were different. I didn’t have to be good at taxes. I just had to be confident that I can learn.
Hannah: Yeah, that’s all it is. You don’t have to memorize the internal revenue code. Nobody does.
Joe: And as proof, what I love is that Hannah is the smartest person I know at taxes. And what was funny was you were nice enough to help some of our stackers that are in our meetup groups around the country and to do this great event for them.
And you even had to stop as the expert and look it up and you’re like, yeah. ’cause it changes every year. Like I always think that same thing. Google is for the little things, right? Yeah. I don’t need to know the little things. If I know the high concept, then I’m gonna be good. So let’s start out then with this.
I want to help people do better with taxes. If you’re thinking about the side hustle, or even if you’re not, you have a whole section of your new book about what the tax form, the tax return is actually for.
Hannah: Mm-hmm.
Joe: Let’s just do complete 1 0 1. What’s the tax return for.
Hannah: I love this, and this actually will touch on a reason that a lot of people tell themselves they’re bad at taxes.
Part of why I like to teach this is it shows you. Oh, that thing that you don’t know the answer to, that’s ’cause you don’t have a crystal ball and having that particular answer you think you’re bad for not having is ’cause no one has it. Basically we live in a system, it’s called a pay as you go tax system.
Meaning, and this makes a lot of sense when you think about what creating policy looks like. You have to pay your taxes as you go throughout the year. Anybody who’s an employee, this is easy, right? You fill out one form with the employer that sets up withholding, so then your employer is taking out your Medicare and Social Security and your federal and state income taxes from every single paycheck.
So you are filling your tax bucket all throughout the year, even though you’ve done that and it’s relatively accurate, you know, you could have, um, hit your head right before you filled out that form and been a little off on the numbers and that’s fine. Or you could have just not known the future and not known that you were gonna be employee of the year and get a massive bonus at the end, and that in fact, your tax rate would be higher than you thought it would.
That’s the thing about life. We don’t have a crystal ball. We don’t know what’s coming. But when you’re self-employed, you don’t have anybody withholding taxes automatically through the year. So that’s when we engage this other system called estimated quarterly taxes. For that, it’s a manual way of breaking up a large tax bill and paying it, you know, one quarter at a time.
That’s far less frequent than every single pay period. So you can still feel like you’re kind of behind a little bit, or like the bill is big, but it’s smaller than a full annual tax bill. But the thing is, when you’re paying in your taxes throughout the year. You are estimating based on what you think your income will be for the year, and you don’t get to know the answer to how much to the dollar income you made for the year till the year’s over.
And for that reason, we file a tax return. The whole point of filing a tax return is to reconcile the estimates that we were paying in throughout the current year with the actual, once we can do the math, once the year is over, once there is an actual total. I think a lot of people feel like, oh, I’m bad with money.
I’m broken. I can’t believe I’m missed backwards in taxes. ’cause they don’t know the answer in the middle of the year when no one knows the answer. So I think that’s the little like mind trick that is important to understand. That is the purpose of a tax return. It’s the reconciliation times where you settle up and make change.
Joe: It is important even if you’re a W2 employee. It’s important. It just is taken largely out of your hands. I mean, if you get a big bonus, maybe on December 31st, it could change everything. Or if Yeah. You know, some big, uh, inheritance or something happens where your income changes, it could change even for those people.
It’s just if when you’re self-employed, you’re gonna see it a lot more.
Hannah: Yeah, absolutely. Plus, when you’re self-employed, you can be even more in the dark than when you’re getting a paycheck because when you’re self-employed, and this is the good thing, but it also causes people to not know what their income, their taxable income is.
You get to take deductions. So if you are self-employed, you get business deductions, this is amazing. But if you’re not doing bookkeeping on a somewhat regular basis, you don’t know what your taxable income even is. So estimating what your taxes are is impossible if you’re not tracking the deductions that you get to take against that income.
Joe: I love the way you phrase that because what that implies is something I’m gonna wanna talk about here, which is it implies that we’re gonna need to set up some systems, and if we set up systems, then we can get around a lot of these scary thoughts in our head about how am I gonna do these quarterly things?
I mean, keep up. What if I owe a lot more money than I thought? Like systems stackers I think can solve all of this. What are some of the deductions? ’cause you’re like, oh my goodness, businesses can deduct so many different things. This is so cool, and it is very, you know, it’s cool. I know it’s cool, but somebody’s sitting there in the heaven started a side hustle.
What are the things that they can do that a regular person can’t do? What are these deductions all about? And by the way, as I even asked that question, for people that haven’t started a side hustle, but they’ve watched good tv, they’ve heard of these things called Writeoffs from the character David and Schitz Creek.
Let’s listen to David talking to his dad about the nature of being in business.
bit: What’s, what’s this looks expensive. Uh, this is some new betting David did. Didn’t I just tell you to save your money? Uh, yeah. I am testing this out for the stores. So work is paying for it. Work is paying for your bedding. I was gonna leave, but now I don’t want to.
So what is that? Is that a new lamp? Yeah. I’m thinking of bringing Homeware, um, into the store. So that’s a write-off. That’s a write-off. Yeah. Do you even know what a write-off is? Uh, yeah. It’s when you buy something for your business and the government pays you back for it. Oh, and who pays for it? Nobody.
You write it off. Who writes it off? I don’t know. The gover, the write-off people. What? Why are we having this conversation
Joe: tell us that David’s right and the write-off people are helping us when we go into our side hustle. Hannah,
Hannah: I knew it was gonna be bad. I love it. Yeah. The government doesn’t pay for your lamp straight up, but Oh, one star to you.
One star to you. Yeah, I do. I do think there’s a lot of press about write-offs that is, uh, it’s good to check with a tax professional every once in a while to be sure that your write-offs are legit.
Joe: The poor lady. By the way, I don’t want to do too much of a spoiler for people. I haven’t seen it. The poor lady goes outta business because of David’s write-offs.
Hannah: It makes sense. That makes sense.
Joe: But how does it really work when I buy stuff as a business expense? Tell me how that works.
Hannah: Basically, the US government is encouraging you to grow your business and they encourage, one of the ways they incentivize that. Is that they say, Hey, if you are paying for things that are investments in your business that are ordinary and necessary, those are IRS words, ordinary and necessary expenses of running your business are deductible.
So effectively, if I earn a thousand dollars from Sunlight Tax, but I spend a hundred dollars on a microphone for the Sunlight Tax Podcast, and I spend $30 a month for, oh, I just made the math complicated. I have a monthly software fee and I have a home office, and I have other expenses, then that will come off that a thousand dollars of income that I have from Sunlight Tax.
In other words. The microphone, the monthly software fee, those are actually subtracted from my taxable income so that my taxable income, what I pay taxes on, is just what I keep. It’s just the profit for my business and not the full gross income. So it’s a huge tax savings, and especially when you begin your business, it’s especially wonderful because expenses always come before profit does.
And so it’s really good to know that that starting clock comes way sooner than most people expect. But yes, you’ve gotta be tracking your deductions and you have to do a little bit of bookkeeping and tracking in order to be able to take those deductions. And Joe, if it’s all right, I have a resource for your stackers if they’re sweet, interested.
OG: Yeah.
Hannah: I have a visual guide to business deductions, so if you’re interested, you can find that on my website. Sunlight tax.com/deductions guide. I realized that in the podcast, you cannot see what I’m holding up, but it’s a rainbow colored chart with three columns and the two main columns. Basically. One column shows what you call the thing you’re spending money on in your business, in your gig, in your side hustle.
The second column shows what the IRS calls that thing. So it just draws a line from one to the other. So you can see, oh, oh, like a paid Facebook ad that would be advertising. I suppose that one’s probably more obvious, but it shows you just where they go. Like, where does business coaching go? Where does a.
Membership community I pay money for to kind of learn about this thing. Where does that go? That’s a really valuable resource. And maybe we can link to that in the show notes as well. Yeah, sure
Joe: will. And what strikes me is, of course you’re an artist. ’cause it looks very pretty.
OG: So much prettier
Joe: than Stacking Benjamins stuff does.
OG: We’re not,
Joe: is we, we, we don’t have the rainbow of colors as we go down stackers. You have to go to Sunlight Tax to get that stuff. You know, you were talking about deductions. Mm-hmm. And people like me, when I started out, I’d hear the word deductions and I heard that was really good from people like you, Hannah.
But then I’d hear the word credit sounds like different words, same thing. What’s the difference between a deduction and a credit?
Hannah: Those are quite different. They’re both good. But it’s basically what’s the strength of the good? A deduction is lower strength. A credit is super strength. A deduction is something that subtracts.
Off of your taxable income. So it lowers the amount of your income that’s subject to tax and that is going to lower your taxes. A credit is a dollar for dollar reduction of tax, you know, the child tax credit or the saver’s credit, which is one that you get when you are a lower income person and you put money into a retirement account like an IRA, those will dollar for dollar reduce your tax bill.
So they’re really strong and really powerful. Depending on what your tax rate is, it could be four or five times more money that you get from a tax credit than from a tax deduction. But both do lower your taxes.
Joe: But if somebody tells you that you can go look for tax credits when you’re doing a home renovation or a something, I mean, this is a big thing to not ignore.
Hannah: It’s very worthwhile. Tax credits are super valuable.
Joe: Yeah, but what’s funny is we even missed deductions because we’re not bookkeeping. Let’s do kind of bookkeeping 1 0 1. So I’m setting up my side hustle here. During the holidays, I got a little bit of time off, right? Mm-hmm. So I’m just rolling into my new business.
How do I make sure that I’m keeping track of all my business expenses? Well,
Hannah: the very best thing that you can do is to just open a separate bank account for your gig, for your side hustle. It doesn’t actually even have to be what the bank would call a business bank account. It can be what the bank calls a personal account.
It just needs to be a separate account that you treat as your business account. So you’re gonna deposit the income from your business into that account and you’re gonna make all your expenses from that account. You can also, if you want the, you know, amazing points, credit card points from a corporate card, you can, you can get like a business credit card.
Joe: Can you also there just use, I know there’s business credit cards, but could I also use just a separate personal card and call it my business card?
Hannah: You sure could. Yeah, that would be totally fine. So really for your record keeping, it’s the separation that is important.
Joe: Okay.
Hannah: And you are the expert on credit cards and which is the best one?
I’m not that person, but
Joe: you know,
Hannah: that’s because
Joe: I tried ’em all back in the day. Hannah.
Hannah: I got, uh oh,
Joe: I got really good. You’ll hear my interview on Hannah show about that. But anyway, yeah.
Hannah: Now we have some stories about debt and credit. That’s right.
Joe: Yeah.
Hannah: So the business cards, basically, if you think about it, like businesses just spend so much money because they have a tax advantage to all of the expenses that they are paying money for.
So business credit cards tend to give you pretty good perks. Mine gives me triple points on all the advertising that I pay for and also triple points on business travel, which is kind of great.
OG: Yeah, that’s cool. Um,
Hannah: but anyway, that’s,
OG: yeah,
Hannah: consulted credit card expert for those. But the point is the separation.
And so if you have a separate business bank account and all your income from the business goes in there and all your expenses come out of there, think about what that bank statement is now doing for you. Now. It’s a record that actually captures everything coming into and going out of your business. So now from there, that’s kind of your starting point for bookkeeping.
Now you can sort. That expense was, you know, home office expense. That expense was supplies, that expense was professional development.
Joe: Do you have a system then? So I can see easily then all my money goes in there, all the expenses come out of there. And so I’ve got this easy record of, of where I stand at any point in time.
So from there I can kind of figure out how much money to send in to the government on a quarterly basis. Is there a way, do you have a system of how you kind of separate that money out for people that are afraid that they might get behind?
Hannah: What I see a lot is that people will take step one and they will set money aside for taxes.
Sometimes even in its own separate account, but they actually don’t pay it quarterly. They wait, they still wait all the way until the next tax return is due April 15th. Once your side hustle is big enough to be generating income, substantial income, you get to a point where you’re required to pay your taxes quarterly.
This is really important to know as your business grows, it’s not typically a concern when it’s teeny tiny or like relatively small and proportion to a day job, but once it becomes a higher percentage of your overall taxable income, you don’t have enough withholding available to you to be able to pay your taxes strictly through payroll withholding, and you have to engage the other system, which is called estimated quarterly taxes.
That’s important to know if quarterly taxes apply to you, if you can’t get enough money withheld from a paycheck to pay in the taxes that you owe for the year, you have to pay quarterly taxes, or you’ll be assessed a quarterly penalty and daily interest. So it really does cost money to not know about that system.
Joe: This is one of those few areas where it truly is a lot different than somebody with a W2 paycheck because W2 paycheck people, I imagine that Hannah are following the same system, but because it’s being withheld every single paycheck, you just don’t ever have to worry about it.
Hannah: Yeah, absolutely. And if you have access to that system and you don’t want to quit your day job, Ben, by all means, use it piggyback on your bosses withholding.
That’s great. And in fact, like a trick for you stackers who are in that boat is you can actually fill out a new W four at any time. The W four is the paperwork you give to your boss that tells them how much withholding you want outta your paychecks. You have a right to change this at any point in the year, and your boss has to implement it.
So if you start a side hustle and it’s starting to generate some income, you can actually go take a W four, print a blank one off the IRS website. Fill it out, hand it into your boss and basically turn up your level of withholding and then you can kind of skip quarterly taxes. But for those of you who wanna quit your day job, if you start making bank and you know, God bless, I hope you do,
OG: yeah.
Hannah: Then you’re gonna have to learn about quarterly taxes and realize that they really do apply to you. Line 38 of your tax return is where you can reference the penalty you’re paying. ’cause you’re not paying quarterly and you’re supposed to. So if you wanna go check with your own eyes, you can look at that.
Um, but that’s really helpful to know that you’re gonna have to learn the quarterly tax system.
Joe: So with my W2, I love that, that I can just turn up the withholding there and not even worry about the quarterly thing if I keep my day job. But certainly to your point, we all want to graduate. Can I also though, when I was starting to climb outta credit card debt, I realized that I needed to.
Know myself all enough to know that I wasn’t to be trusted with money in my hand. So the quicker it went where it was supposed to go, the better. Yeah. Do I have to wait for the quarter to end or can I just, if I get checks, maybe irregularly from my side hustle. Let’s say it’s speaking gigs, right? Yeah. To use one that happens to me all the time.
So I get a speaking gig, they pay me a nice fee. Can I just, instead of waiting till the next quarter, can I just send it into the IRS today?
Hannah: Well, you can, you can do that. So the thing about quarterly taxes that’s so different from payroll, withholding quarterly taxes are totally manual. So you can log into irs.gov, click them, make a payment button at any time, and you can make a payment.
And if you have big chunks of income like that and you don’t wanna hold onto the money ’cause you think you might fritter it away on comics and bubblegum, then you can go ahead and you can make that payment. That’s fine. I suppose, you know, if you’re optimizing your personal finances and you wanna hang onto your money in a high interest savings account, as long as you can,
Joe: yeah,
Hannah: you can do those things.
Oh, sure. But you can pay it right away if you want to.
Joe: To me, at first, at first, it was more important that I just get it to the right place. Mm-hmm. Now that I’ve got much better systems than it became much easier. Speaking of that, there’s a time when I need to engage professionals to help me with bookkeeping.
Right. Your side hustle blows up, you quit the day job, you tell the boss I’m done, which is an awesome day. Now you work for yourself. At what point do you hire the bookkeeper?
Hannah: Yeah, yeah. Hiring a bookkeeper is, first of all, every bookkeeper I’ve ever referred people to has become full, and so I’m always looking for bookkeepers.
Everyone is always looking for bookkeepers. It’s a good line of work to be in. Because there’s a need
Joe: there. It is stackers. This is an employment show too.
Hannah: Yeah. If you’re a college grad suffering from that really low, um, employment rate right now. Yeah. Look into bookkeeping. You can get yourself certified.
Good start. And then hit me up because I can refer people to you. Sorry this was brought to you by ZipRecruiter. That’s right. I’m just
Joe: kidding. It was the perfect line, wasn’t it? It was the perfect place for an ad placement right there. Too bad we don’t have ZipRecruiter. You missed out.
Hannah: Yeah, you did miss out.
So, um, the thing about setting up bookkeeping, you can do it on your own, you can do it manually and that’s fine. When I say manually, what I mean is you can do it just with a spreadsheet. And I honestly think that is not a bad way to go when your side hustle is pretty sidey, you know, like nice and small.
But if you’re starting to blow up. I would actually recommend if you’re gonna use bookkeeping software, that you actually hire a bookkeeper in order to set up books for you. The reason is it’s not that simple and it’s bookkeeping software is based on the system called Double Entry Bookkeeping, where there’s two accounts that are touched with every transaction you make.
And believe me, it’s very easy to get turned around and to set that up wrong. So the wrong accounts are getting touched each time. And to undo the mess that compounds over time when you have poorly set up books is way more expensive than just shelling out for a good, competent bookkeeper on the front end to set up upright.
So that is a thing to be aware of. If you then wanna have your, your well set up books and do your own bookkeeping after that, that’s fine, but the actual setup is a bit of a place for
Joe: a professional. There are other systems that I should think about text-wise. Is I setting up my business?
Hannah: Yeah, you know, I talk about three systems.
These are really, really simple, basic systems, but knowing the difference between the three of them actually kind of can be very helpful. ’cause people tend to confuse them for each other and that’s what makes things messy. Bookkeeping is one of them. Bookkeeping is the hardest one. So it’s the heaviest lift and it’s also the one that takes maintenance over time.
So at a minimum, if you have to pay quarterly taxes, at a minimum, you wanna be doing bookkeeping at least quarterly, because that allows you to know your profit, calculate a tax payment and make a tax payment on time. But the other two systems, and these ones are really easy and they can take just five minutes to set up are keeping your receipts.
So receipt tracking, and the other one is tax documents. So pretty simple receipts are actually not what anybody should be doing their bookkeeping from. That’s where things get horrifying and messy, and where you have a panic attack
Joe: when you’re bringing in the, the shoebox of old receipts.
Hannah: Totally. If you’re bookkeeping out of a shoebox of receipts, you, you’ll have a panic attack.
I, I almost guarantee it, and I say this from personal experience, having had that panic attack, what’s important to know is that a receipt is your proof that a deduction really happened, that you didn’t make it up. And the IRS has the right to look at your tax return going back as far as six years, and they can say, show us all your business receipts in any given year.
So you wanna have them, but the good news is those can just go in cold storage. I recommend storing them by year because audits happen by year. And so if you can just pull out 20, 24 receipts and not have to wade through 23 and 22 and 21, that’s great, but that’s it. You just need to store them. And as long as you can access them, if you are asked, you’re good.
Now bookkeeping is where you actually say. And these three expenses that I had the receipts for over there, these three expenses were supplies, office supplies. These three were professional development expenses. These were, you know, client meals that I had to grow a business relationship. So that’s the bookkeeping.
Joe: One of the surprises, there were many surprises the other night when you were helping our Benjamins after dark groups, but one that really surprised me was you said that people start too late to track their expenses when they’re doing just the research on their side hustle.
Hannah: A lot of people don’t realize that your business expenses can start before your business starts.
There’s a category of deduction called startup expenses. I have a whole podcast episode about startup expenses on the Sunlight Tax Podcast. So if you want me, we could put a link to initial notes to that episode. But startup expenses are basically anything that would have qualified as a business expense if you had been in business.
But it’s happening before in the sort of research phase or the beginning phase. So it’s totally fine to keep those receipts and track those. And then the moment your business starts, which ps to the IRS, that moment is the moment you advertise, not the moment you’re profitable, not the moment you form an LLC.
Not only of those things, but the moment you advertise. So think about what that means. Advertising is like saying, hello world, I’m open. That’s the moment your business starts. And so you don’t have maybe even a dollar in the door at that point.
OG: Yeah, but
Hannah: that’s the moment where on your tax return, you put the start time and then you can go backwards and all those expenses that you spent money on before to set up the business and they, they will exist because you will have had to do that.
Those get to go in this bucket called startup expenses.
Joe: Does it matter how many years back?
Hannah: You know, I don’t wanna give you the answer ’cause I don’t have that memorized. Yeah, I believe it does not. But I, I would wanna check before I said definitively.
Joe: Yeah. Get some help on that stackers.
Hannah: Yeah.
Joe: Well guys, we just began, there is this, uh, this book that Hannah wrote that came out last week on this topic, has so much stuff.
I love Chapter 14, safe, like a Millionaire, tax Advantage Accounts and everything we talked about. Notice the tone. It was all 1 0 1. It was all, you can do it. The entire book is written with that tone, which is why it’s a beautiful thing for anybody you know, who’s starting. A business who’s afraid of taxes, who just wants to know how does this stuff work without having something that, you know, even on Stacking Benjamins, I have people tell us before we’re like, I didn’t understand hell you were telling in that, you know, anything you were talking about in that segment, it just all went right over my head.
Well, if that’s That’s what you’re afraid of, then Hannah’s new book, taxes for Humans, simplify Your Taxes and Change the World When you’re self-employed is available everywhere. Right?
Hannah: It is. It’s available everywhere.
Joe: Awesome. We will link to that in the show notes. Hannah, thank you so much as usual for mentoring our stackers today.
I super appreciate it and happy holidays to you.
Hannah: Happy holidays to you, Joe. I hope they’re wonderful. Thank you for having me again. It’s so awesome to talk to you.
Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and today we celebrate the birthday of legendary comedian, actor and writer Richard Pryor Pryor. A black comedian learned early on to perform for largely white audiences during the turbulent 1960s. However, by the 1970s, Pryor was able to lean into his fame by creating humor that appealed to a wide audience, making him even more famous.
And by the mid 1970s, writing and starring in films, his biggest film most experts agree, is a Western. He co-wrote with director Mel Brooks and others afflict that’s listed in the American Film Institute as the number eight comedy of all time. What Benjamin Stacking film was it? I’ll be back right after I go see just how many prior comedies Joe’s mom seen.
Well, I don’t even mean to like. Pryor as in before this. I mean it’s figure it out. It’s prayer. P. It’s prayer. It’s a short eye. It’s the short eye on that one. Maybe that’s where the confusion is.
Hey there, stackers. I’m Richard Pryor, fan and guy who collects half pennies. Joe’s mom’s neighbor, Doug in Superman. Three Pryor’s character. Gus Gorman takes all the half pennies from transactions and transfers them all to his bank account. I always wondered how much glue that guy had to put ’em all together.
Lots of work I think. I don’t know if it’s worth it, but today’s question is about the iconic comedian’s writing credits. His biggest, according to the American Film Institute was his Western co-written with director Mel Brooks and others. It’s listed as the number eight comedy of all time. What film was it prior?
Co-wrote the classic film, blazing Saddles starring Gene Wilder and Cleon Little. And now back to two guys. Blazing financial literacy, Joe and og.
bit: It’s not the only thing. Joe’s blazing.
Joe: Spark it
Doug: up. Baby
Joe: Santa’s pants are blazing today. You know, blazing Saddle. So many. Doug, you and I were talking about this earlier, but Oh gee.
So many classic lines from that movie. Oh man, I don’t know that I’ve ever seen it, honestly. Oh wow. I mean, here’s one of them. Uh, gene Wilder. Uh, just say Willy Wonka.
bit: Use his real name. Use his real name. I’m a stage name.
Joe: You know the other Willy Wonka’s that have been out there? Gene Wilder is Willy Wonka,
Doug: right?
Yeah. They’re all trying to Yes. Top him and you can’t,
Joe: but here’s Gene Wilder in Blazing Saddles.
bit: Hey Jim, since you are my guest and I’m your host, what are your pleasures? What do you like to do? Well, I don’t know. Play chess. Screw.
TikTok: Well, let’s play chess.
Doug: . See, we got OG to laugh. Yeah, that’s pretty funny. And you said you hadn’t seen it. It does hold up. Like that’s one of those films that does stand the test of time. There’s some great, in fact there’s, it’s also in the style of like a 30 rock or parks and rec or whatever. There’s so many throwaway lines that you, you’re not gonna get all of ’em right away.
You gotta watch that thing a couple of times. There’s a lot of buried humor in there.
Joe: And I think because he’s not. In the movie, people don’t realize Richard Pryor was involved.
Doug: I give, and actually until I did deep, deep research for this trivia, I didn’t realize that he was,
Joe: by the way, big thanks to Hannah Cole for Texas 1 0 1.
Just it, it’s brilliant when somebody can take taxes and make it make sense to the average person. I feel like yeah, simplify it. Yeah. So often we talk over people’s heads, but even better than Hannah Cole, the person who blurbed the back cover of the book. Like, just that dude is amazing. Oh gee. Who could that have been, Joe, so, so strange.
We won’t, we won’t, uh, daddle on that point. We’ll go ahead and let that one go. That person that blurbed the back cover, we, we won’t talk about it anymore at all.
Doug: I can’t believe they didn’t put a picture of that person on the cover of the book. I don’t
Joe: know why they wouldn’t,
Doug: why
Joe: that person should have been really angry, but showed a lot of restraint.
I’m sure by not, by not bringing it up over and over again. Hey, uh, time for the TikTok minute. This is the part of the show where we just shine away to get Joe to
bit: move on. I don’t know. The hand signal. Oh, that’s stretch it out. That’s for going, that’s stage direction
Doug: for keep going.
Joe: Stretch it out. I think you were telling me to talk more about the person who was on the back cover.
Dam it. That’s exactly
Doug: what those hand motions mean. You, you did the right. Yeah,
Joe: it’s, that was making hand motion. Oh, there
bit: we go. I knew it was something with your neck and being
Joe: strangled. Yes. You’re killing me. Dive for a TikTok minute. The part of the show where we shine a light on a TikTok creator who’s doing something brilliant or air quotes brilliant.
Which one you think this one is OG
bit: frigging awesome.
Joe: Well, according to. Stacker Julia, she sent this one and she goes, you know, this, this might scare me a little bit. This is, uh, Damien Sol. I’m not sure what the point is that Damien is making here. I think there might be an under undertone of some concern.
Let’s see if anybody can grok through the mist. Uh, really the point he’s trying to make.
TikTok: Sell everything. Stocks, shares, bonds, commodities, property, crypto. I don’t care what it is. Get out of all markets now. Exit. Exit all markets. Do you understand? I’m one of the owners of the largest hedge fund in the UK, and we went off risk two days ago because we know what’s about to happen.
The reason why gold is spiking through the roof like it’s World War III is because the everything bubble is about to collapse. This means that everything will essentially go to zero. Everything that has value go down by at least 98%. That includes the money in your bank accounts. You can’t just leave your money lying around thinking it’s safe, and then buy the dip.
Your money will be worthless. Do you understand? You need to exit the system entirely and protect your money by investing in something else. Classic cars, boats, watches. I don’t know. Okay? You have to get out of the system. Now. This is my final warning. Sell everything. Protect yourself. Because what’s about to come, it’s gonna shock everybody.
bit: Hey, Siri, set a reminder for six months from now to see if the market is down 98%. Well,
Doug: funny you should say that. Why is that, Doug? Well, isn’t that pretty old? Didn’t didn’t that guy actually published that months ago. Yeah. What’s funny is when Julie sent this to me, this in recent,
bit: oh, who knew?
Joe: I looked at it and this, and this is from September, by the way, number one, but also just number two, investing in watches classic cars.
bit: I love the idea. It’s a great boat. Honey, we’re gonna sell everything. Well, okay. We just, uh, de-risk a little bit. No, no, no, no, no. It’s not really a de-risk solution. It’s more of a be very concentrated in something that’s even less liquid than the entire summation of the world’s most profitable companies of all time.
I think we should buy a 1964 Ferrari
OG: for our retirement.
bit: Obviously, Doug, also a matching paddock, Philippe. So I’m gonna have that. We’re gonna have the Ferrari,
Joe: then we’ll be good. Well, what about this though, og? I’d love your commentary on this. This came out just a few weeks ago before Thanksgiving. I got the headline here from Tech Round.
Peter Teal exits Nvidia and Tesla. Are we closer to the AI bubble burst than we think? Peter Thiel sold his entire Nvidia stake during Q3. He had to report. Of course. Um, when you’re a huge shareholder, you have to report these things, and so Teal gets completely out of one of the biggest AI plays of all og.
And maybe it’s not going down 98%, but oh my goodness. You can’t, you can’t do anything in the popular press right now and not see. AI bubble. AI bubble. AI bubble. During, you know, during November we saw this rundown of a lot of big companies and a lot of people waiting for the pin to burst. When it comes to AI bubble, you think about that
bit: bubble burst.
Bubble burst. Remember the pins? The pins do the bursting.
Joe: Oh yeah. The pins do.
bit: Waiting for someone to pop the bubble that, that guy’s holding. He’s holding the pin.
Joe: Thank you. Yes. I’ll go back to drinking outta Santa’s pants and let you chat this up.
bit: Well, I think, you know, when you look at the rise of the stock market, I think it’s only natural to say like, Hey, we’ve reached all time highs.
That must mean that the other, the other side of this thing’s gonna happen, right? There’s ups and then there’s downs, and it’s been a solid five years since there’s been a pretty big down. So does that make sense statistically that we have a big down here somewhere along the line? I think the answer is who knows?
I don’t think it really much matters if you’re a long-term investor. If you’re, you’re somebody that’s gonna be investing. If you’re 40 or 50 years old and you have 20 years to go, what happens in the next six months to Nvidia stock? Frankly, in 20 years, Nvidia might not even be a company who gives a crap what happens to Nvidia stock.
If you’re diversified and you own a bunch of stuff, that doesn’t mean that the market’s not gonna go down. It doesn’t mean that you’re not gonna have, you know, a 30% decline. But I don’t think that means that you do anything different from an investing standpoint other than continue to follow your plan, invest and, and rebalance when appropriate.
There’s a slight difference if you’re retired and taking money out. But Doug has a question. Um, um, Mr. Neighbor, Doug, go ahead.
Doug: Uh, thank you for taking my question. Question from, uh, every, every man representing every man here, og is this one of those cases where we should also be wary of who the messenger is.
As soon as he said I managed the largest hedge fund in the uk, it occurred to me could there be some ulterior motives? Um, like did he short everything and if he gets everybody to sell out, that somehow that benefits his hedge funds. I mean, is that a thing or am I over overreading it?
bit: As much as we’d like to believe that there’s some sort of conspiracy theory around they want us to do this so they can profit, I mean the, the global market is so gigantic that even the biggest people don’t have that
Doug: much sway.
So you’re saying he doesn’t have enough followers? That’s what I’m hearing on TikTok to get people to move the market for him.
bit: Honestly, don’t think so. Maybe with an individual position. There was a great book many, many, many, many years ago called Fooling some of the people all of the time, and it was about a, uh, hedge fund in Connecticut that had a thesis about a, a specific stock that was overvalued and the levels that the, the company was going to, to prevent the stock from going down.
You know, so I think an individual position, you could have some players that manipulate it quite a bit
Doug: like a GameStop situation.
bit: Sure. But the market as a whole seems pretty impenetrable because of the sheer volume. And I’m sure there’s plenty of people out there who can find stats to be like, actually no, check this out.
It’s, you know, whatever. But just it doesn’t make sense to me.
Joe: The difficulty for me isn’t whether the market will go down or not. I love what you said there, Archie, that it will, at some point it will, it it, yeah. You know, as people listen to this today, we recorded this before you’re hearing it, it might have dropped precipitously between those, those moments.
bit: Yeah. Wouldn’t that be funny? We’re like recording this a little early and they’re like, might go down. My God, it’s crashing around us. Where have you been? Idiot. Where idiots?
Joe: Where have you been? Idiot, idiot. Like, remember that with, with our travel schedule a few years ago we had that happen and somebody was like, the world is melting and you guys act like nothing’s happening.
It’s like, well, because in May nothing was it, it came right back up. The market came up very quickly. And, uh, panic did not win the day, which it never does. Here’s the interesting thing about the AI bubble, og, it strikes me when you say that Nvidia might not even be a company. Of course, it, it might not. I mean, you look at what’s happened to every industry ever.
I mean, back in the nineties, GE was the behemoth, right? And ge still a growing concern. Still a, a good company, but not nearly what it was in the nineties Yeah. To the s and p 500. Now we’re saying the same thing about Microsoft and Apple and Nvidia more than any of those companies. So when we look at AI.
I don’t think the win with AI is these companies where there may be a bubble anyway, it’s how is Proctor and Gamble going to use AI in the future to get ahead? There’s this whole second wave, like we saw in the nineties, there’s a wave after the 2008 market. There’s always this second wave that comes around that’s a sometimes a direct reaction, sometimes not a direct reaction.
And you really have a choice. Do I stay broadly diversified or do I guess when it’s gonna drop and when it’s done? And every time one of those two scenarios was a loser every time, not some of the time, every time you were a loser if you tried to guess.
bit: I think that it’s really a development of emotional competence that happens through an investor’s career.
You know, where early on you feel like you have a lot more control than you really do. And I think the realization as you get further into your investing life that. You have absolutely no control over any of this. You can’t predict it. And there’s, you know, you can have opinions. I mean, I’ve got opinions about it, just like I’m sure you guys do, and obviously this guy does.
He has an opinion about it, but I can’t prove my theory is correct anymore than this guy, or you guys can prove yours. And I think once you recognize from an investing standpoint, that not only do you not have any influence over it, nor do you have any control, but nor does anyone else, nobody has any control over it and nobody else can predict what’s gonna happen.
And uh, and that’s just part of the trade, part of the trade of getting 10% a year in the s and p is that some years you go down 30, that’s the trade. And um, if you look at all of recorded history, that’s the trade that pays off. You say, well, but I don’t like the minus 30. Well. Then invest in bonds and you have to save.
You have to work your plan to say, what happens with a 3% return after inflation? How much more do I have to save? How much longer do I have to work? Once I think you distill all this down into it’s just math, and you go, I can take the math that’s 7% after inflation, or I can take math that’s 3% after inflation, and here’s my resources, and here’s how long I feel like working.
Right. There you go. All right. You know, look. Look, if you’ve got $25 million in the bank and you’re like, I don’t want the minus 30 anymore. I spend 10,000 a month on my Amex card and I feel pretty comfortable, what’s your money in cash? Okay. I think it’s a terrible, terribly stupid idea, but you know,
Doug: the math equation, you can only solve the math equation, the X to the left of the equal sign.
If you can determine ahead of time where you want to go. So complex way of saying, figure out what your goal is. We say it like every week on this show, figure out what the goal is, that’s to the right side of the equal sign, and then you can solve and do the math on the left side of the equal sign.
That’s kinda what I just visualized as you were saying that. Is that right og?
bit: It’s an interesting way to put it. Ultimately, if you put in the restrictions that you’re, you know, what are, what are my things that I’m not willing to miss out on? Or what are the things that I’m not willing to to participate in?
Then you can have some open-ended variables that work in there. If you say, Hey, I’ve got $50 million in the bank. I don’t wanna play the minus 30 game. I spend 10,000 a month. You’re good, then you can put your money in your savings account and you’re good. If you say, I’ve got $500,000, I’m 52, I can save 20,000 a year in my 401k and get a little company match.
I wanna retire when I’m 62 and I wanna spend 10,000 a month. Okay, well you need a different return number than the guy with 50. That’s just then then’s just the facts. If you say, well, I don’t want that, then we have to change something else. To your point, Doug, it’s like, okay, well 62 is not a number.
You’re gonna look at 70 or 20,000 is not your saving number. You need to say 40. But when you approach it that way and look at the end of the day, there’s a lot of people who have invested over the last, is it getting close on 20 years now? My gosh, ha. Have invested, you know, over this 20 year period of a pretty healthy bull market that don’t really remember the pullbacks that have happened.
There was a pretty big giant minus 20 in 2012. And for those of you who were investing in at that time, that’s kind of on the heels of 2008, 2009, like you’re just getting your lips back above water and then you get sucked in the face with, oh, by the way, the US debt’s not as good as we’ve all been told it was.
Here’s a minus 20 in the, in the last couple months of the year we had a minus 30 with COVID. We had a minus 2022 and some change in 2020. Uh uh, 2022. Right? So we’ve experienced this already. You’ve already done this. And so if you’re looking at the the next thing and saying, oh my gosh, if the market goes down 20, I don’t want to do, you’ve already done it.
The world has already experienced this no less than four or five times in the last 20 years and we’re still okay. How quickly we forget. I was reading an article by one of my favorite advisor authors and he was making a case for making a pretty pointed discussion around 25 years because we’re in 2025 and it’s hard to like fathom that it’s been a quarter century since 2000.
He’s like, you need to have it. You’re ready. Basically, his, his his article was like, you need to have it. You’re ready. Like all this crap that’s happened in the last 25 years. ’cause this is kind of like an investor’s career and it’s like, this has already happened in these 25 years. Just timeline out some stuff that you have that has happened in your own life or in in the markets or whatever.
You know, whatever catastrophe you feel like remembering, just timeline that out and just go, are we still okay today? Versus what I thought we were gonna be like when that catastrophe happened or when that thing happened. And so, yeah, the market’s gonna go down another 20%. It’s gonna go down 30%. Hell, we probably got a minus 50 sometime in our lifetime again, and it will suck every bit of it.
But on the other side of it, that’s just part of how the cycle works. You have to see through the chaos and the malaise of, you know, all these catastrophes that are, that are trying to. Gets you to do dumb things. Is that not a word, Doug? Did I say that right?
Doug: No, I think that is a word and I’m like, damn, that’s a good one.
Bang, catastrophists. Oh, if it’s not, we’re we’re doing it
bit: catastrophe. It’s a long high,
Joe: I don’t know. I don’t think that guy was pointed enough. Do you think he’s a catastrophes? Do you think he think he’s gonna go down? I got the feeling he might think the mic market might go down.
bit: I mean, I saw something, you know, just to kinda wrap this up, I saw a thing the other day.
So Michael Burry made famous in the big Short as the guy who bet, you know, on the housing market going down, made a big bet earlier this year on the negative of ai, you know, sometime in the fall. And then within five days of getting a lot of hate mail on that deregistered, his hedge fund said, okay, we’re not managing people’s money anymore.
We’re out. And the theory is by Deregistering, he never had, he doesn’t have to show his cards anymore. He can just be a private investor that also happens to manage a couple billion dollars or whatever the hell he does. People are like, see, that means it’s really gonna be bad because he doesn’t want people to know what he’s doing so he can make all this money.
And, you know, okay, I’m not a trader. There’s gonna be plenty of people who trade all of this stuff that’s happening, that are gonna make insane amounts of money. And they’re gonna be books about it. And, and Michael Lewis is gonna write a book and it’s gonna be a movie. And you’re gonna go, how did I not, you know, negative, short $25 trillion of AI stock and make a hundred bajillion for my family.
Okay? Because you didn’t have the balls to do it. If you’re on board with this thesis, back the truck up the other way, right? But that’s just a dumb way to invest. That’s not investing, that’s trading. And so if you’re a trader, then go after it, you know? And, and maybe you’ll be successful. But if you’re a long-term investor and you’re planning for your family’s retirement, or you’re planning for your kids’ education or your grandkids, you know, and building this family wealth.
What happens in the next two years or three years, doesn’t matter. Hill of beans, you’ll forget about it. Just like you forgot about what happened in 2012 and all the other
Joe: years. It’ll just be a blip. Thanks to Julia for sending that in. If you’ve got, uh, uh, TikTok minute, you’d like us to parlay into our headline like you did julia stackingBenjamins dot com, uh, excuse me, just send it to me, Joe@Stacking Benjamins.com, that’s a great place to go.
That is just about all for today. Of course, at the end we have our community segment porch, lots of fun stuff back porch with our community. We call it the back porch. Yeah. Doug, what’s going on in the back porch?
Doug: Well, I think the biggest thing going on is, uh, updates to the guides.
Joe: It’s so exciting every month if you’re new here, we have these guides on different areas of your financial plan, and we update them every month.
You buy them one time and then every single month. So you should have received already stackers your email from us that, that got new guides are live. And I will let those be a surprise. I think you’re gonna be happy with what we’ve done this month. Uh, a, we had a little fun, as you’ll see. And then B, there’s also new updates.
So whether it’s the tax planning guide, the college planning guide, you should be, if you’ve got people getting ready to go to college, you gotta be right in the middle of a bunch of planning stuff this July. And then of course, our HR guide, StackingBenjamins.com/guides gets you there. Happy December everyone with the new updates.
If you’re not here because you need one guide, you really are here because you know what? I need to make better financial decisions in 2026 than I did in 2025. OG and his team are taking clients, taking client meetings for 2026, get on their calendar because they take meetings for new clients early in the year.
We generally then don’t talk about it in the middle of the year. So if you want to get in, get in now, StackingBenjamins.com/OG to meet with either OG or Anna. Uh, who you heard again last week, Doug. She came very close to maybe being a better co-host than OG can be.
Doug: Wow, my God. She was so much more enjoyable to be with.
She was. She had this warmth to her. She just had this friendliness that didn’t. Fans of the show aren’t used to that
Joe: though. I gotta say. They’re like, what the hell is this?
Doug: I get it, but it’s awfully nice not to just get shoved away from the table like OG does to me every time. Yeah. Bruises on my left shoulder.
Joe: StackingBenjamins dot com slash og. Stop
bit: being so infirm
Joe: you can get the same loving treatment on a one-on-one level that he gives us here.
Coming up on Wednesday. I don’t know if you guys have ever heard of this guy, Morgan Housel. Little known name in personal finance.
Doug: No idea who you’re talking about.
Joe: The psych, the Psychology of Money was a great book that, uh, Morgan had. Now he’s talking about a topic that I think we all need to hear about in December.
Og The Artist of Spending Christmas. Yeah, the Art of Spending. OG knows the art of spending. Morgan might have a different take. I have a
bit: PhD in it
Joe: that’s coming up on Wednesday in a rare two mentor week. Alright, that’s it for today, Doug. You got it From here, man. What should we have learned on today’s show?
Doug: So, what should we have learned today? First, take some advice from Hannah Cole. You don’t need to worry about complex tax strategies to save money on your bill by understanding just the basics. Taxes for humans. You’ll find yourself with more money and a better understanding of good tax plans and horrible ones.
Second, guessing whether the market is gonna drop with your money. That’s always been a losing game. But the big lesson, don’t fool yourself into thinking that Joe’s mom has seen all the great movies. She hasn’t even seen Blazing saddles and get this. If I just wash the dishes for the next five days, she said she’d watch it with me.
It seems like a pretty great deal, huh? Huge thanks to Hannah Cole for joining us. You’ll find her book Taxes for Humans. Wherever books are sold, buy one for the financial noob and Your Friend group. We’ll link to it in our show notes at StackingBenjamins.com. This show is the Property of SB podcast LC, copyright 2025, and is created by Joe Saul-Sehy.
Joe gets some 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.
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.
OG: Oh
Joe: gee, this is not a movie I’ve seen, but this trailer. Is, uh, well this is maybe the biggest, the biggest horror movie that could ever, ever, ever happen. Let’s take a listen. This is from the team at something called SNL. You familiar with them? Let’s hear.
bit: So what are you up to this week at? Chris and I are gonna hang at home, which is exactly what I need.
We’ve had something to do the past five weekends in a row, so I’m very much looking forward to doing literally nothing.
Who’s that babe? My cousin. She just texted me almost there. What does that mean? Oh god, I think. I think we have, we have what plans from house, the studio that brought you Insidious and Annabel Rise of Horal comes a terrifying story about when the thing you agreed to do four months ago is today. Fucking this happen.
Let me think. The 4th of July, my mom’s barbecue, she said she wanted to come to the city in the fall. Oh my God. We, we must have said a date. Which, which cousin is it? Which cousin? Is it the one who runs marathons? Tokyo. I ran a 5, 15, 28, but I hadn’t trained. You really wanna get into Berlin? The way I see it, losing toenails is a badge of honor.
It’s okay. This is okay Chris, you guys can hang out and I’ll just do my own thing. Chris. I mean, she’s not my cousin, so it’s her husband is coming too. The guy who always shows me YouTube videos. Oh man, you gotta see this. I can’t believe you haven’t seen this. 11 minutes. I found an email she sent in August.
No, they wanna do drinks here. Then dinner at that viral ramen place. So crowded and overhyped. Then go to some immersive play based on the story of Snow White, the one where you’re part of the show. Seven. Seven lies. Just tell them we have COVID. They don’t believe in that. You thought you were safe. Don’t believe.
Hey, wanna see 1000 pictures of my dog? Please? No. Leave me alone please.
Joe: You thought you could go look up the rest of that ’cause that goes on for about another two minutes, but that that is the worst. When I think that, oh my goodness, I got a weekend of nothing.
bit: We are so diligent about our calendar, our family calendar, you know, ’cause you got the work calendar, you got the SB podcast calendar, you got your personal calendar, you got your team’s calendar, right?
Because you gotta like know who’s, you know, somebody out this week, whatever, free days, uh, you got holidays, you got your spouse’s calendar for when they do stuff, you know, a hair appointments, whatever. And then you got the kid calendar, which is when are the sporting activities? Who gets out early on what day?
And now we also have the college calendar of. When that kid is around. Yeah. And so, yeah, so you look at it and you go, oh my God, it’s empty. You like take off the jeans and put sweatpants back on. Right. You’re like, not saying that this has happened to me, but you can imagine what it’d be like, you know when your wife’s like, is it nine o’clock and you’re drinking beer?
You’re like, hypothetically, we don’t have anything to do today. It’s empty. And then your wife says, oh, I’m sorry, I forgot there is a softball tournament that starts at 10. I forgot to put that in. You’re like, huh, I forgot. We, we got invited over to the neighbor’s house for, well, I guess I’ll be the drunk dad at the, uh, 10:00 AM softball, 9-year-old softball tournament.
Then because, ’cause this train ain’t stopping. We, we started that engine up and this is the little engine that could, we ain’t slowing this puppy down for nothing.
Joe: I had a friend in college who had a name for that. He called it Turning the Corner. You know how you go out and you’re like, okay, I’m just, you know, I got a big day tomorrow.
I gotta, I gotta do my marathon training. Yeah. I got, I got all these things I gotta do. And then you just get to a point just after two beers where you’re like, it, yeah, don’t care. I have turned the corner. And he kept cautioning about that. We don’t want to turn the quarter tonight, we don’t wanna turn the corner.
And then around 1130 or midnight, or 1230, and we’re at Taco Bell, we’re like, why did we
Doug: streaking? We’re going streaking. This is so great.
Joe: Not good. Yeah. I, I hate that phone. Ding. Old school. What a horror story.
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