The Tax Basics You Should've Learned Years Ago (But Nobody Taught You) SB1768

Summary

Podcast Summary: The Stacking Benjamins Show

Episode: The Tax Basics You Should've Learned Years Ago (But Nobody Taught You) SB1768

Date: December 1, 2025
Main Guests: Joe Saul-Sehy (Host), OG (Co-host), Doug (Joe’s Mom’s Neighbor), Hannah Cole (Tax Expert & Author)

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Overview

This episode focuses on demystifying taxes for everyday people—especially side hustlers, freelancers, and anyone intimidated by the U.S. tax system. Joe and OG are joined by tax expert Hannah Cole, who delivers a back-to-basics, approachable "taxes 101" session designed for those who feel lost when it comes to the IRS, deductions, business expenses and credits. The discussion highlights key differences between deductions and credits, setting up tax systems for side hustles, when to hire a bookkeeper, and resetting your mindset about financial skills. The episode mixes practical advice with humor and real-life stories, embodying the “fun and functional” tone the Stacking Benjamins Show is known for.

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Key Discussion Points & Insights

1. Why Taxes Aren’t as Scary as They Seem (10:19–11:56)

• Hannah Cole debunks the myth that taxes are impossible for regular people to understand, especially those looking to start a side hustle or become self-employed.
  • "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 U.S. tax code." (10:49 - Hannah Cole)
• Even very small, garage-based businesses can access significant tax benefits.

2. Mindset About Money & Taxes (12:13–15:54)

• The self-defeating belief that creative people or artists MUST be bad with money is false.
  • "Artists, frankly, because they have to be, they are so resourceful... As soon as you start to believe that yourself, you can make it come true." (13:25 - Hannah Cole)
• Belief in your ability to learn new financial skills—rather than some inborn talent—makes all the difference.

3. What a Tax Return Actually Does: The “Reconciliation” (16:48–19:32)

• The U.S. uses a “pay as you go” tax system.
  • Employees have taxes withheld each paycheck; self-employed people must estimate and pay quarterly.
  • The tax return “settles up” yearly estimates with the actual year’s results.
  • "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..." (18:07 - Hannah Cole)
• Not knowing your tax liability mid-year does NOT make you “bad at taxes."

4. Deductions, Credits, and How Write-Offs (Actually) Work (21:31–26:48)

• Common “write-off” misconceptions (helpfully illustrated via a "Schitt’s Creek" clip).
  • The government doesn’t “pay you back” for business purchases; instead, legitimate expenses reduce taxable income.
  • Ordinary and necessary expenses (IRS language) are deductible.
    • “If I earn $1,000 from sunlight tax, but I spend $100 on a microphone... [and more]... those are actually subtracted from my taxable income.” (23:00 - Hannah Cole)
• Difference between deduction and credit:
  • Deductions lower taxable income (lower-strength benefit).
  • Credits are dollar-for-dollar reductions of your tax bill (super-strength).
    • “Tax credits are super valuable.” (26:57 - Hannah Cole)

5. Bookkeeping Basics & Systems for Side Hustlers (27:00–34:39)

• First step: open a separate bank account (does not need to be a formal business account) and, if possible, use a separate card for expenses.
  • “The very best thing that you can do is to just open a separate bank account for your gig, for your side hustle.” (27:15 - Hannah Cole)
• Bookkeeping doesn’t have to be complex:
  • For beginners: use a spreadsheet tracking income and expenses.
  • As income grows: consider bookkeeping software (with professional setup for double-entry systems).
    • “It’s very easy to get turned around... undo[ing] the mess... is way more expensive than just shelling out for a good competent bookkeeper on the front end.” (35:06 - Hannah Cole)

6. Systems for Tax Success (36:19–40:13)

• Three core systems:
  1. Bookkeeping – categorize, tally, and summarize expenses.
  2. Receipt tracking – keep digital or physical records by year; you need these if you're audited.
  3. Tax documents – organize all tax forms for easy access.
  • “Bookkeeping is where you actually say, oh, these three expenses... were supplies... these were professional development.” (37:18 - Hannah Cole)
• Startup Expense Deductions:
  • You can deduct certain expenses before you officially launch, up until you “advertise” your business.
  • “Advertising is like saying, hello world, I'm open. That's the moment your business starts.” (39:14 - Hannah Cole)

7. Managing Quarterly Taxes & Withholding (29:46–33:50 and 31:13–32:26)

• Once your business/side hustle grows, you may be required to make quarterly estimated tax payments to avoid penalties.
  • “If quarterly taxes apply to you... you have to pay quarterly taxes or you'll be assessed a quarterly penalty and daily interest.” (30:58 - Hannah Cole)
• W-2 holders can increase withholding to cover side gig taxes by submitting a new W-4.
• Pro tip: After a windfall (e.g. speaking fee), you can manually submit payment to the IRS right away, not just quarterly.

8. Broader Investing Lessons: Handling Market Panic (49:03–64:35)

• Segment debunks financial panic and market catastrophe clickbait, e.g. “Sell everything!” TikTok.
• Long-term perspective and diversification always win over market timing or panic selling.
  • "What happens in the next six months... in 20 years, Nvidia might not even be a company. Who gives a crap?" (52:20 - OG)
  • "Every time... you were a loser if you tried to guess." (56:58 - Joe Saul-Sehy)
• Hindsight reminders: Even sharp recent corrections (“COVID crash,” 2012, etc.) felt terrifying in the moment, but “panic never wins the day.”
• Emphasizes goals-based planning, risk management, and emotional competence as investor virtues.

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Notable Quotes & Memorable Moments

• On artists and money skills:
  • “We're incredible. We're real, like doers, and we make things that are invisible to people suddenly become real... And, yeah, we get kind of fed this line that we're bad at money..." (13:25 – Hannah Cole)
• On what the tax return really does:
  • “…the purpose of a tax return. It’s the reconciliation times where you settle up and make change.” (18:31 – Hannah Cole)
• On the “write-off” myth:
  • “Yeah, it’s when you buy something for your business and the government pays you back for it.” (22:02 – Schitt’s Creek clip via Joe Saul-Sehy)
  • “The government doesn’t pay for your lamp.” (22:23 – Hannah Cole)
• On bookkeeping priorities:
  • “I honestly think [a spreadsheet] is not a bad way to go when your side hustle is pretty sidey, you know, like nice and small.” (34:57 – Hannah Cole)
• On starting to track expenses before you form your business:
  • “A lot of people don’t realize that your business expenses can start before your business starts. There’s a category...called startup expenses.” (38:46 – Hannah Cole)

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Timestamps for Important Segments

| Timestamp | Segment | |-----------|---------| | 10:05 | Introduction of Hannah Cole, “Taxes 101 for humans” | | 12:13 | Addressing mindset and financial skills (artist stereotype) | | 16:48 | The purpose of a tax return explained | | 21:31 | Business deductions and the truth about write-offs (plus Schitt's Creek clip) | | 25:58 | Deductions vs Credits clarified | | 27:15 | Bookkeeping basics—separate accounts/cards | | 29:46 | Managing quarterly estimated taxes | | 31:13 | Increasing W2 withholding to manage gig tax liability | | 33:12 | Making manual IRS payments after variable gig income | | 38:46 | Starting to track “startup expenses” before official business launch | | 52:06 | Market bubble talk, Nvidia/AI, why panic is never an investment plan | | 56:58 | Diversification, staying the course, and goal-based investing |

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Additional Resources from the Episode

• Hannah Cole’s “Visual Guide to Business Deductions”:
  Available at sunlighttax.com/deductionsguide
• Hannah Cole’s book:
  • Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed (linked in show notes)
• Mentioned podcast episodes:
  • Sunlight Tax Podcast’s episode on start-up expenses

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Tone & Style

The episode maintains the casual, witty, and demystifying spirit that’s the hallmark of Stacking Benjamins. Joe, OG, and Doug blend playful banter with actionable insight, and Hannah Cole brings warmth, encouragement, and practical step-by-step advice—making taxes feel like something any regular person can conquer.

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Who Should Listen & Why

• Side hustlers, freelancers, and new entrepreneurs: A rare, judgment-free walkthrough of the essentials
• Anyone scared of the IRS or “bad at taxes”: Mindset shifts and approachable explanations
• Listeners bored by financial jargon: Entertaining, lighthearted, and never condescending

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Summary

This episode is a must-listen for anyone who wants a clear, confidence-boosting crash course in taxes—especially if you’re venturing into self-employment or still feel like the IRS code is a foreign language. With concrete advice, myth-busting, and encouragement from a tax expert who gets what it’s like to be “bad with numbers”—plus the ever-present SB laughs and pop-culture moments—you’ll walk away understanding how tax returns work, what actually counts as a “write-off,” why credits matter more than most realize, and how to keep the IRS from ruining your side hustle dreams.

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"You don't have to memorize the Internal Revenue Code. Nobody does."
— Hannah Cole (15:54)

"Every time you tried to guess, you were a loser."
— Joe Saul-Sehy (56:58)

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Transcript

[Joe Saul Sehive]

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[Sponsor Voice]

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[Joe Saul Sehive]

Happy Cyber Monday, guys. I'm surprised I could get you on the microphone when there's deals galore online.

[Doug (Joe's mom's neighbor)]

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 Saul Sehive]

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 (Joe's mom's neighbor)]

Remember back like 3 weeks ago when the early Black Friday deals were getting released in the beginning of November? Like, this is out of control.

[Joe Saul Sehive]

It's going to be July next year. They're going to have Black Friday in July.

[Doug (Joe's mom's neighbor)]

Exactly.

[Joe Saul Sehive]

Yeah.

[Doug (Joe's mom's neighbor)]

But I Amazon kind of does that.

[Joe Saul Sehive]

I thought I'd celebrate the start of December for our every Monday salute to the troops, but by bringing out my Christmas mug, which I always thought was really neat, but there is just something a little weird and creepy about drinking out of Santa's pants. Like just for people. For people that can't see my mug. It is Santa's pants. I'm drinking out of Santa's pants. I don't know what that means.

[Doug (Joe's mom's neighbor)]

I don't know what it says that just made me laugh. Like real laughter.

[Joe Saul Sehive]

Let's raise our mugs, guys. Raise in this place? It's OG doesn't even know what to do. It's like I got no idea.

[Doug (Joe's mom's neighbor)]

Shaking his head in grinchiness.

[Joe Saul Sehive]

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 want to 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 (Joe's mom's neighbor)]

Thanks, everybody.

[OG]

Cheers.

[Doug (Joe's mom's neighbor)]

My mug's Christmassy looking until you realize it's from a distillery, which is still Christmassy. Yeah, that's cheer, baby, right there.

[Joe Saul Sehive]

If you got to be around the in laws, why not get the distillery involved? All right, let's do it.

[Doug (Joe's mom's neighbor)]

Here we go. Live from Joe's mom's basement, it's the Stacking Benjamin Show. I'm 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.

[OG]

Primer.

[Doug (Joe's mom's neighbor)]

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, Hannah 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? Plus, we'll share a TikTok minute.

[Joe Saul Sehive]

Sure.

[Doug (Joe's mom's neighbor)]

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 Teresa. I totally don't. It's Joe and O.J. ja, ja, G.

[Joe Saul Sehive]

Don't think of OG and I just slightly ahead of Mother Teresa.

[Doug (Joe's mom's neighbor)]

Not ahead of Mother. I mean, you come into mind eventually, but it's a long way after Mother Teresa.

[OG]

For the record, I don't know if ChatGPT is wrong on this or if Doug is wrong on this. It's a 5050 shot here. But just for the record, ChatGPT 5.1 does suggest that primer is the correct usage in primer.

[Doug (Joe's mom's neighbor)]

In what context?

[OG]

A basic booklet of instructions or a short introduction to a topic.

[Doug (Joe's mom's neighbor)]

And ChatGPT is saying short eye is.

[OG]

Used when you mean paint or a base layer.

[Doug (Joe's mom's neighbor)]

ChatGPT is 100% reverse.

[OG]

100% wrong.

[Joe Saul Sehive]

Okay.

[OG]

All right, well, I'll just. I'll have a word with Sam later and we will fix that. I find it hard to believe that ChatGPT is wrong with anything, but.

[Joe Saul Sehive]

Okay, shockingly, shockingly, AI is wrong again when you ask it a question.

[OG]

I 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. What just happened?

[Joe Saul Sehive]

Do you hear Santa's pants just bubble?

[OG]

Did you just snort into Santa's pants?

[Doug (Joe's mom's neighbor)]

That's what that was.

[Joe Saul Sehive]

Santa's pants just bubbled.

[OG]

Did somebody just did Santa's pants? Sharp. While you were drinking out of them.

[Joe Saul Sehive]

I reached. I was taking a drink and I reached the part where it goes down into his leg and so it.

[OG]

Santa just sharted while you were drinking out of his pants. Okay.

[Doug (Joe's mom's neighbor)]

Another high end highbrow moment from Stacking Benjamin.

[Joe Saul Sehive]

Wow. But 60 Minutes, anyways, I've got.

[OG]

I got a great thing from 60 Minutes. A little piece that maybe we can share later. Maybe later this week.

[Joe Saul Sehive]

I don't know.

[OG]

We'll see.

[Joe Saul Sehive]

Well, I got to 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 going to take this foundation down to the studs, as they say. And.

[OG]

Yeah, here. Oh, wait, different meaning. Let me chat. GPT that 1/ Real quick.

[Joe Saul Sehive]

Hannah Cole is going to 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 1040, and then I. I knew the difference between a deduction and a tax credit. Yeah. Like, at first I thought they were just kind of the same thing, but with different names. 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 year end 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 going to hear from them and then Taxes for humans with our friend Hannah Cole. This message is sponsored by Navy Federal Credit Union. As the holiday season rolls around, we know that you strive to do everything you can to bring cheer and joy to your loved ones. And as a credit union dedicated to serving all veterans, active duty and their families, we understand that every little bit counts. That's why for a limited time you could earn a 250 cash bonus when you spend $2,500 with Navy Federal's cash rewards and cash rewards plus cards in the first 90 days. Of course, Stackers. This is part of a big financial plan, right? Don't get yourself into debt. Make sure that you are spending and saving with a plan. But you know what? The giving doesn't stop there. You could also earn up to 2% unlimited cash back with these cards. So saving up for whatever the season brings just got a little easier. Give joy, get joy. Join now@navy federal.org Navy Federal Credit Union. Our members are the mission. Navy Federal is insured by NCUA. Visit navy federal.org cash rewards for details. Cash back terms and conditions apply. Offer ends January 1, 2026.

[Sponsor Voice]

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[Joe Saul Sehive]

Hey, let's Talk. Not taxes 201 or 301 or 401. 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 Coles here. How are you?

[Hannah Cole]

I'm so good, Joe. Thanks for having me. Great to be here.

[Joe Saul Sehive]

Well, I'm glad that you could be here and help our stackers with taxes one on one because all of our stackers tell us, Hannah, they want to start a side hustle. They want to 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 kind of. We hear all these things. The taxes are tough and evil and wild and impenetrable. Tell us that's not the case.

[Hannah Cole]

It's not the case. And in fact, it's so wonderful to Realize if you're 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 Saul Sehive]

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 going to want to listen to this, you're going to want to mark this episode, you're going to want to come back to it, because we're going to dive in to that. And if you're not starting a business, we're just going to talk a little taxes 101 for the next 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 have 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 Cole]

Oh, you mean my dad's accountant.

[Joe Saul Sehive]

Oh, it was your dad's accountant. I thought it was your dad. It was your dad's accountant.

[Hannah Cole]

My parents were very encouraging to. I want to 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 going to get a real job?

[Joe Saul Sehive]

Oh, my God. Boy, that's encouraging.

[Hannah Cole]

I was like, you're looking at it.

[Joe Saul Sehive]

Maybe I thought it was your dad instead of your dad's accountant, because my dad, this 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? Like you think it's gonna. I was like, yeah, I think maybe. I think it's going okay, Dad, I.

[Hannah Cole]

Think we're gonna be. Yeah, well, you showed him, didn't you?

[OG]

I think we're.

[Joe Saul Sehive]

I think we're gonna be fine. Well, no, the answer is no, I didn't stick with it. I went on to 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, 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 Adoga. 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 stereotype among artist that you even talk about in your book. That's not true at all.

[Hannah Cole]

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 want to 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 say this because I am one and because my community, are creative people. We're incredible. We're real, like doers, and 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. As soon as you start to believe that yourself, you can make it come true. 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 Saul Sehive]

And you say, like, any other skill when we start out. I mean, it truly is our mindset that matters.

[Hannah Cole]

Yeah, I mean, if you tell yourself you're terrible at something, there's really good evidence. I say this. I have two daughters. 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 the stereotype, even if your daughter's about to crush it on this math exam, if you remind her of a stereotype about girls in math right before she goes in 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 Saul Sehive]

But it's funny On Friday, we did our annual board game episode. 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 going to get it. You can see them shut down immediately. Like, I'm not going to get it. I'm like, 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 going to be just fine. I feel like taxes are kind of the same. When somebody sat me down with the 1040, Hannah, and literally went through, 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 Cole]

Yeah, that's all it is. You don't have to memorize the Internal Revenue Code. Nobody does.

[Joe Saul Sehive]

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 is the expert and look it up. And you're like, yeah, because 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 going to 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. Let's just do complete one on one. What's the tax return for?

[Hannah Cole]

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 because you don't have a crystal ball. And having that particular answer you think you're bad for not having is because 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 hit your head right before you filled out that form and been a little off on the numbers and, and that's fine. Or you could have just not known the future and not known that you were going to 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 is 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. And I think a lot of people feel like, oh, I'm bad with money, I'm broken. I can't believe I'm this backwards in taxes. Because 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 Saul Sehive]

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, you know, some Big 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 going to see it a lot more.

[Hannah Cole]

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 Saul Sehive]

I love the way you phrase that because what that implies is something I'm going to want to talk about here, which is it implies that we're going to 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 going to do these quarterly things, how am I going to 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? Because you're like, oh my goodness, businesses can deduct so many different things. This is so cool. And, and it is very cool. You know it's cool. I know it's cool. But somebody is sitting there and they haven't 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 write offs from the character David in Schitt's Creek. Let's listen to David talking to his dad about the nature of being in business. What's. What's this?

[Doug (Joe's mom's neighbor)]

Looks expensive.

[Joe Saul Sehive]

This is some new bedding.

[Doug (Joe's mom's neighbor)]

David, did.

[Joe Saul Sehive]

Didn't I just tell you to save your money? Yeah. I am testing this out for the stores. So work is paying for it.

[Doug (Joe's mom's neighbor)]

Work is paying for your bedding.

[Hannah Cole]

I was gonna leave, but now I don't want to.

[Doug (Joe's mom's neighbor)]

What is that? Is that a new lamp?

[Joe Saul Sehive]

Yeah. I'm thinking of bringing homeware into the store. So that's a write off. That's A write off? Yeah.

[Doug (Joe's mom's neighbor)]

Do you even know what a write off is?

[Joe Saul Sehive]

Yeah, it's when you buy something for your business and the government pays you back for it.

[Doug (Joe's mom's neighbor)]

Oh, and who pays for it?

[Joe Saul Sehive]

Nobody. You write it off.

[Doug (Joe's mom's neighbor)]

Who writes it off?

[TikTok Creator / Voice Actor]

I don't know.

[Joe Saul Sehive]

The government. The write off people.

[OG]

Why are we having this conversation?

[Joe Saul Sehive]

Tell us that David's right and the write off people are helping us when we go into our side hustle.

[OG]

Hannah.

[Hannah Cole]

I knew it was gonna be that. I love it. Yeah. The government doesn't pay for your lamp.

[Joe Saul Sehive]

Straight up. One star to you. One star to you.

[Hannah Cole]

Yeah, I do. I do think there's a lot of press about write offs. That is, it's good to check with a tax professional every once in a while to be sure that your write offs are legit.

[Joe Saul Sehive]

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 out of business because of David's write offs.

[Hannah Cole]

It makes sense. That makes sense.

[Joe Saul Sehive]

But how does it really work when I buy stuff as a business expense? Tell me how that works.

[Hannah Cole]

Basically, the US Government is encouraging you to grow your business and they incur. 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 $1,000 from sunlight tax, but I spend $100 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 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 got to 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 interested.

[Joe Saul Sehive]

Yeah.

[Hannah Cole]

I have a visual guide to business deductions. So if you're interested, you can find that on my website, sunlighttax.com deductionsguide 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. Right. 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.

[Joe Saul Sehive]

Yeah, sure will. And what strikes me is of course you're an artist because it looks very pretty. So much prettier than Stacky Benjamin stuff does. We're not as 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 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 Cole]

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 savers 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 $ 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 Saul Sehive]

But if somebody tells you that you can go look for tax credits when you're doing a home renovation or something. I mean, this is a big thing to not ignore.

[Hannah Cole]

It's very worthwhile. Tax credits are super valuable. Yeah.

[Joe Saul Sehive]

But what's funny is we even missed deductions because we're not bookkeeping. Let's do kind of bookkeeping 101. So I'm setting up my side hustle here. During the holidays, I get a little bit of time off. Right. So I'm just rolling into my new business. How do I make sure that I'm keeping track of all my business expense as well?

[Hannah Cole]

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 going to deposit the income from your business into that account, and you're going to 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 Saul Sehive]

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 Cole]

You sure could. Yeah, that would be totally fine. So really, for your record keeping, it's the separation that is important.

[Joe Saul Sehive]

Okay.

[Hannah Cole]

And you are the expert on credit cards and which is the best one? I'm not that person. But, you know, that's because I tried.

[Joe Saul Sehive]

Them all back in the day, Hannah. Uh.

[Hannah Cole]

Oh, I got really good.

[Joe Saul Sehive]

You'll hear my interview on Hannah's show about that.

[Hannah Cole]

But anyway, yeah, now we have some stories about debt and credit.

[Joe Saul Sehive]

That's right.

[Hannah Cole]

Y 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.

[Joe Saul Sehive]

Yeah, that's cool.

[Hannah Cole]

But anyway, that's. Consult a 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, oh, that expense was, you know, home office expense. That expense was supplies. That expense was professional development.

[Joe Saul Sehive]

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 Cole]

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 if, as your business grows, it's not typically a concern when it's teeny tiny or, like, relatively small in 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. 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 Saul Sehive]

Yeah. 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 Cole]

Yeah, absolutely. And if you have access to that system and you don't want to quit your day job, then by all means, use it piggyback on your boss's 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 W4 at any time. The W4 is the paperwork you give to your boss that tells them how much withholding you want out of 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 W4, 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 want to quit your day job if you start making bank and, you know, God bless, I hope you do.

[Joe Saul Sehive]

Yeah.

[Hannah Cole]

Then you're going to 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 because you're not paying quarterly and you're supposed to. So if you want to go check with your own eyes, you can look at that. But that's really helpful to know that you're going to have to learn the quarterly tax system.

[Joe Saul Sehive]

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 out of credit card debt, I realized that I needed to know myself well 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. 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? 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 Cole]

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 the 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 want to hold on to the money because 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 want to hang on to your money in A high interest savings account as long as you can. Yeah, you can do those things, but you can pay it right away if you want to.

[Joe Saul Sehive]

To me, at first, at first it was more important that I just get it to the right place. 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 Cole]

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 there.

[Joe Saul Sehive]

It is stackers. This is an employment show too.

[Hannah Cole]

Yeah. If you're a college grad suffering from that really low employment rate right now.

[Joe Saul Sehive]

Yeah.

[Hannah Cole]

Look into bookkeeping. You can get yourself certified.

[Joe Saul Sehive]

Good start.

[Hannah Cole]

And then hit me up because I can refer people to you. Sorry, this was brought to you by ZipRecruiter.

[Joe Saul Sehive]

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 zip recruiter. You missed out.

[Hannah Cole]

Yeah, you did miss out. So 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 going to 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 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. Right. So that is a thing to be aware of. If you then want to have 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 a professional.

[Joe Saul Sehive]

There are other systems that I should think about tax wise, as I'm setting up my business.

[Hannah Cole]

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 because 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 want to 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 Saul Sehive]

When you're bringing in the shoebox of old receipts.

[Hannah Cole]

Totally. If you're bookkeeping out of a shoebox of receipts, you'll have a panic attack, I almost guarantee it. 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 want to 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, oh, and these three expenses that I have 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 Saul Sehive]

One of the surprises. There were many surprises the other night when you were helping our Benjamin's 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 Cole]

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 expense 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 in the show 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 psych to the irs, that moment is the moment you advertise. Not the moment you're profitable, not the moment you form an llc, not any 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. Yeah, but 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 will exist because you will have had to do that. Those get to go in this bucket called startup expenses.

[Joe Saul Sehive]

Does it matter how many years back?

[Hannah Cole]

You know, I don't want to give you the answer because I don't have that memorized. I believe it does not, but I would want to check before I said definitively.

[Joe Saul Sehive]

Yeah, get some help on that. Stackers.

[Hannah Cole]

Yeah.

[Joe Saul Sehive]

Well, guys, we just began there is this, this book that Hannah wrote that came out last week on this topic has so much stuff I love. Chapter 14, Save Like a Millionaire Tax advantaged accounts and everything we talked about. Notice the tone. It was all 101. 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 Benjamin's, I've had 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 is 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? It is.

[Hannah Cole]

It's available everywhere.

[Joe Saul Sehive]

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 Cole]

Happy holidays to you Joe. I hope they are wonderful. Thank you for having me again. It's so awesome to talk to you.

[Joe Saul Sehive]

This is Rebecca from Connecticut.

[OG]

Instead of stacking Hamiltons and Jacksons, I'd.

[Hannah Cole]

Much rather be stacking Benjamins.

[Doug (Joe's mom's neighbor)]

Hey there stackers. I'm Joe's mom's neighbor Doug and today we celebrate the birthday 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, a flick 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 mean like prior as in before this. I mean figure it out.

[OG]

Prayer Prayer.

[Joe Saul Sehive]

It's a short eye.

[Doug (Joe's mom's neighbor)]

The short eye on that one. Maybe that's where the confusion is.

[Joe Saul Sehive]

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[Doug (Joe's mom's neighbor)]

Hey there, stackers. I'm Richard Pryor fan and Gayu collects half pennies, Joe's mom's neighbor Doug. In Superman 3. 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 them 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 direct 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 Cleavon Little. And now back to two guys blazing financial literacy, Joe and OG.

[OG]

It's not the only thing Joe's blazing.

[Doug (Joe's mom's neighbor)]

Spark it up, baby.

[Joe Saul Sehive]

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.

[Doug (Joe's mom's neighbor)]

Oh, man, I don't know that I've.

[OG]

Ever seen it, honestly.

[Doug (Joe's mom's neighbor)]

Oh, wow.

[Joe Saul Sehive]

I mean, here's one of them. Gene Wilder.

[OG]

Just say Willy Wonka.

[Doug (Joe's mom's neighbor)]

Use his real name.

[OG]

Use his real name. Have a stage name.

[Joe Saul Sehive]

You know the other Willy Wonkas that have been out there? Gene Wilder is Willy Wonka.

[Doug (Joe's mom's neighbor)]

Yeah, they're all trying to top him and you can't.

[Joe Saul Sehive]

But here's Gene Wilder in Blazing Saddles.

[OG]

Hey, Jim, since you are my guest and I am your host, what are your pleasures?

[Hannah Cole]

What you like to do?

[Doug (Joe's mom's neighbor)]

Oh, I don't know.

[TikTok Creator / Voice Actor]

Play chess? Screw.

[OG]

Well, let's play chess.

[Doug (Joe's mom's neighbor)]

See, we got OG to laugh.

[OG]

Yeah, that's pretty funny.

[Doug (Joe's mom's neighbor)]

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 what. There's so many throwaway lines that you're not going to get all of them right away. You got to watch that thing a couple of times. There's a lot of buried humor in there.

[Joe Saul Sehive]

And I think because he's not in the movie, people don't realize Richard Pryor was involved.

[Doug (Joe's mom's neighbor)]

I did, actually. Until I did deep, deep research for this trivia, I didn't realize that he.

[Joe Saul Sehive]

Was, by the way, big thanks to Hannah Cole for Texas 101. Just. It's brilliant when somebody can take taxes and make it make sense to the average person. I feel like. Yeah, so often we talk over people's heads. But even better than Hannah Cole, the. The person who blurbed the back cover of the book, like just. That dude is amazing.

[Doug (Joe's mom's neighbor)]

See, who could that have been, Joe?

[Joe Saul Sehive]

So, so strange. We won't. We won't dawdle on that point. We'll go ahead and let that one go. That person that blurbed the back cover. We won't talk about it anymore at all.

[Doug (Joe's mom's neighbor)]

I can't believe they didn't put a picture of that person on the COVID of the book.

[Joe Saul Sehive]

I don't know why they wouldn't. Why 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, time for the tick tock minute. This is the part of the show.

[OG]

Where we just trying to get Joe to move on. I don't know the hand signal.

[Doug (Joe's mom's neighbor)]

Oh, that. Stretch it out. That's direction for keep going.

[Joe Saul Sehive]

I thought you were telling me to talk more about the person who was on the back cover.

[Doug (Joe's mom's neighbor)]

That's exactly what those hand motions mean. You did the right.

[Joe Saul Sehive]

Yeah. Motion.

[OG]

Oh, there we go. I knew it was something with your neck being strong.

[Doug (Joe's mom's neighbor)]

Strangled.

[Joe Saul Sehive]

Yes. You're killing me. Diver Tik tok 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]

Og fraking awesome.

[Joe Saul Sehive]

Well, according to Stacker Julia, she sent this one and she goes, you know, this. This might scare me a little bit. This is Damien soil. Ash, 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. Really the point he's trying to Make. Sell everything.

[TikTok Creator / Voice Actor]

Stocks, shares, bonds, commodities, property. Crypto. I don't care what it is. Get out of all markets now.

[Joe Saul Sehive]

Exit.

[TikTok Creator / Voice Actor]

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 3 is because the everything bubble is about to collapse. This means that everything will essentially go to zero. Everything that has value will go down by at least 98%. That includes the money in your bank account. 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 is going to shock everybody.

[OG]

Hey, Siri, set a reminder for six months from now to see if the market is down 98%.

[Doug (Joe's mom's neighbor)]

Well, funny you should say that.

[Joe Saul Sehive]

Why is that, Doug?

[Doug (Joe's mom's neighbor)]

Isn't that pretty old? Didn't that guy actually publish that months ago?

[Joe Saul Sehive]

Yeah, what's funny is when Julia sent.

[OG]

This to me recent. Oh, who knew?

[Joe Saul Sehive]

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.

[OG]

I love the idea. It's a great. Honey, we're going to sell everything.

[Joe Saul Sehive]

Well, okay.

[OG]

We just 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 for our retirement. Obviously also a matching Patek Philippe. So I'm going to have that. We're going to have the Ferrari. Then we'll be good.

[Joe Saul Sehive]

Well, what about this, though? Oh, gee, 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 Thiel 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, 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, what do you think about that?

[Doug (Joe's mom's neighbor)]

Bubble burst Bubble for the pins. The pins do the bursting.

[Joe Saul Sehive]

Oh, yeah, the pins do.

[OG]

Waiting for someone to pop the bubble.

[Doug (Joe's mom's neighbor)]

That guy, he's holding the pen.

[Joe Saul Sehive]

Thank you. Yes. I'll go back to drinking out of Santa's pants and let you chat this up.

[OG]

Well, I think when you look at the rise of the stock market, I think it's only natural to say, hey, we've reached all time highs. That must mean that 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 somebody that's going to 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.

[Joe Saul Sehive]

Going to go down.

[OG]

It doesn't mean that you're not going to have 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 rebalance when appropriate. There's a slight difference if you're retired and taking money out. But Doug has a question. Mr.

[Joe Saul Sehive]

Neighbor. Doug, go ahead.

[Doug (Joe's mom's neighbor)]

Thank you for taking my question. Question from every man representing every man here. Og, Is this one of those cases where we also be wary of who the messenger is? As soon as he said, I manage the largest hedge fund in the uk, it occurred to me, could there be some ulterior motives, 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?

[OG]

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 global market is so gigantic that even the biggest people don't have that much sway.

[Doug (Joe's mom's neighbor)]

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.

[OG]

Honestly don't think so. Maybe with an individual position. There's a great book many, many, many, many years ago called Fooling Some of the People all of the Time, and it was about a hedge fund in Connecticut that had a thesis about a specific stock that was overvalued and the levels that the company was going to to prevent the stock from going down. So I think an individual position, you could have some players that manipulate it quite a bit.

[Doug (Joe's mom's neighbor)]

The GameStop situation, sure.

[OG]

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 whatever, but just. It doesn't make sense to me.

[Joe Saul Sehive]

The difficulty for me isn't whether the market will go down or not. I love what you said there, Ochi, that it will. At some point it will. 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.

[OG]

Yeah, wouldn't that be funny? We're like, recording this a little earlier. They're like, might go down. My God, it's crashing around us.

[Doug (Joe's mom's neighbor)]

Where have you been?

[OG]

Where it is like, remember that with.

[Joe Saul Sehive]

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.

[OG]

It's like, well, because in May, nothing was it.

[Joe Saul Sehive]

It came right back up. The market came up very quickly, and panic did not win the day, which it never does. Here's the interesting thing about the AI bubble. Oh, gee. It strikes me when you say that Nvidia might not even be a company. Of course it might not. I mean, you look at what's happened to every industry ever. I mean, back in the 90s, GE was the behemoth, right? And GE, still a growing concern, still a good company, but not nearly what it was in the 90s to the S&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 Procter and Gamble going to use AI in the future to get ahead? There's this whole second wave like we saw in the 90s. 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 going to 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.

[OG]

I think that it's really a development of emotional competence that happens through an investor's career 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 any more 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 going to happen. 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 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 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. And you go, all right, look, if you've got $25 million in the bank and you're like, I don't want the -30 anymore, I spend 10,000amonth on my Amex card and I feel pretty comfortable. Put your money in cash. Okay. I think it's terribly stupid idea, but.

[Doug (Joe's mom's neighbor)]

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 kind of what I just visualized as you were saying that. Is that right?

[OG]

OG 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 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 want to play the minus 30 game. I spend 10,000amonth.

[Joe Saul Sehive]

Okay, you're good.

[OG]

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 401 and get a little company match. I want to retire when I'm 62 and I want to spend 10,000amonth. Okay, well you need a different return number than the guy with 50. That's just, them'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?

[Joe Saul Sehive]

My gosh.

[OG]

Have invested 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 -20 in 2012. And for those of you who were investing at that time, that's kind of on the heels of 2008, 2009. You're just getting your lips back above water and 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 last couple months of the year, we had a minus 30 with COVID we had a minus 2022 and some change in 2020. 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.

[Doug (Joe's mom's neighbor)]

How quickly we forget.

[OG]

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 fathom that it's been a quarter century since 2000. He's like, you need to have at your ready, basically. His article was like, you need to have at your ready all this crap that's happened in the last 25 years. Because 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 the markets or whatever catastrophe you feel like remembering. Just timeline that out and just go, are we still okay today versus what I thought we were going to be like when that catastrophe happened or when that thing happened. And so, yeah, the market's going to go down another 20%. It's going to 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 catastrophists that are, that are trying to get you to do dumb things. Is that not a word, Doug? Did I say that right?

[Doug (Joe's mom's neighbor)]

No, I think that is a word. And I'm like, damn, that's a good one.

[Joe Saul Sehive]

Bang.

[Doug (Joe's mom's neighbor)]

Catastrophists.

[OG]

Oh, if it's not, we're catastrophist, it's a long.

[Doug (Joe's mom's neighbor)]

I. I don't know.

[Joe Saul Sehive]

I don't think that guy was pointed enough. Do you think he's a catastrophist? You think. You think it's going to go down? I got the feeling he might. The M market might go down.

[OG]

I mean, I saw something, you know, just to kind of wrap this up. I saw A thing the other day. So Michael Bur, 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. And people are like, see that means it's really going to be bad because he doesn't want people to know what he's doing so he can make all this money. And you know, and okay, I'm not a trader. There's going to be plenty of people who trade all of this stuff that's happening that are going to make insane amounts of money and there are going to be books about it and Michael Lewis is going to write a book and it's going to be a movie and you're going to go, how did I not negative short $25 trillion of AI stock and make 100 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. 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 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, building this family wealth, then 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 years. There'll just be a blip.

[Joe Saul Sehive]

Thanks to Julia for sending that in. If you've got a TikTok minute you'd like us to parlay into our headline like you did. Julia Stacky, benjamin.com Excuse me, just send it to me [e-mail] that's a great place to go. That is just about all for today. Of course at the end we have our community segment. Lots of fun stuff with our community. We call it the back porch. Yeah Doug, what's going on the back porch.

[Doug (Joe's mom's neighbor)]

Well, I think the biggest thing going on is updates to the guides.

[Joe Saul Sehive]

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 the got new guides are live and I will let those be a surprise. I think you're going to be happy with what we've done this month. 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 got to be right in the middle of a bunch of planning stuff this July. And then of course, our HR guide, stacky benjamin.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. Stacky Benjamins.com OG to meet with either OG or Anna, who you heard again last week, Doug. She came very close to maybe being a better co host than OG can be.

[Doug (Joe's mom's neighbor)]

Well, 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 fans.

[Joe Saul Sehive]

Of the show aren't used to. That though, I gotta say, they're like, what the hell is this?

[Doug (Joe's mom's neighbor)]

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.

[OG]

Stuckybenjamins.com being so infirm.

[Joe Saul Sehive]

And 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 (Joe's mom's neighbor)]

No idea.

[Joe Saul Sehive]

He's talking about the Psychology of Money was a great book that Morgan had. Now he's talking about a topic that I think we all need to hear about in December. OG the artist spending Christmas. Yeah, the art of spending. OG knows the art of spending. Morgan might have a Different take.

[OG]

I have a PhD in it.

[Joe Saul Sehive]

That's coming up on Wednesday in a Rare2Mentor Week. All right, that's it for today, Doug. You got it from here, man. What should we have learned on today's show?

[Doug (Joe's mom's neighbor)]

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 going to 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. 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 in your friend group. We'll link to it in our show [e-mail]. this show is the property of SB Podcasts, LLC, Copyright 2025, and is created by Joe Saul Sehive. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome team@stacking benjamin's.com along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello.

[OG]

Oh, yeah.

[Doug (Joe's mom's neighbor)]

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.

[Joe Saul Sehive]

Sa. Sam. Oh, gee. This is not a movie I've seen, but this trailer is. 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.

[Sponsor Voice]

So what are you up to this weekend?

[Joe Saul Sehive]

Chris and I are gonna hang at.

[Hannah Cole]

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.

[OG]

Who's that, babe?

[Hannah Cole]

My cousin. She just texted me. Almost there.

[OG]

What does that mean?

[Hannah Cole]

Oh, God, I think. I think we have we have what.

[Joe Saul Sehive]

Plans? From Blumhouse, the studio that brought you Insidious and Annabelle. Rise of Hordal comes a terrifying story.

[Doug (Joe's mom's neighbor)]

About when the thing you agreed to.

[Joe Saul Sehive]

Do four months ago is today.

[OG]

How could this happen?

[Hannah Cole]

Let me think. The fourth of July, My mom's barbecue. She said she wanted to come to the city in the fall.

[Doug (Joe's mom's neighbor)]

Oh, my God.

[Hannah Cole]

We must have set a date.

[Joe Saul Sehive]

Which.

[OG]

Which cousin is it? Which cousin is it?

[Hannah Cole]

The one who runs marathons. Tokyo. I ran a 5, 15, 28, but I hadn't trained. You really want to get into Berlin?

[Joe Saul Sehive]

The way I see it, losing toenails.

[OG]

Is a badge of honor.

[Joe Saul Sehive]

It's okay.

[OG]

This is okay, Chris. You guys can hang out and I'll just do my own thing.

[Hannah Cole]

Chris.

[OG]

I mean, she's not my cousin, so.

[Joe Saul Sehive]

Chris.

[Hannah Cole]

Her husband is coming too.

[OG]

The guy who always shows me YouTube videos. Oh, man, you gotta see this. I can't believe you haven't seen it. 11 minutes.

[Hannah Cole]

I found an email she sent in August. They want to do drinks here, then dinner at that viral ramen place.

[OG]

So crowded and overhyped.

[Hannah Cole]

Then go to some immersive play based on the story of Snow White.

[OG]

The one where you're part of the show. Seven Dwarfs, Seven Lies. Just tell them we have.

[Joe Saul Sehive]

Have Covid.

[Hannah Cole]

They don't believe in that. You thought you were safe.

[OG]

Hey, want to see 1000 pictures of my dog?

[Joe Saul Sehive]

Please, no.

[OG]

Leave me alone, please.

[Joe Saul Sehive]

You could go look up the rest of that because 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.

[OG]

We are so diligent about our calendar, our family calendar, you know, because 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. You got holidays. You got your spouse's calendar for when they do stuff, you know, like 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, you know, when that kid is.

[Joe Saul Sehive]

Yeah.

[OG]

And so, yeah. So you look at it, you go, oh, my God, it's empty. You, like, take off the jeans and put sweatpants back on. Right? 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 9 o' clock and you're drinking beer?

[Joe Saul Sehive]

Hypothetically.

[OG]

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. And you're like, huh, I forgot.

[Joe Saul Sehive]

We got invited over to the neighbor's house for.

[OG]

Well, I guess I'll be the drunk dad at the 10am Softball 9 year old softball tournament then. Cause this train ain't stopping. We started that engine up and this is the little engine that could. We ain't slowing this puppy down for nothing.

[Joe Saul Sehive]

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 corner tonight. We don't want to turn the corner. And then around 11:30 or midnight or 12:30 and we're at Taco Bell, we're like, why did we streaking? We're going streaking. This is so great. Not good. Yeah, I hate that phone. Ding.

[OG]

Old school.

[Joe Saul Sehive]

What a horror story.