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- [00:00]
Hannah Cole
This is an iHeart podcast.
- [00:04]
Joel
This episode is brought to you by Navy Federal Credit Union. Navy Federal is proud to serve over 2 million veterans and their families because their service inspires Navy Federals and your.
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Sponsor/Announcer
Service opens the door to membership, which means you get access to exclusive rates, discounts and financial tools that you can share with your whole family. Become a member@navyfederal.org veterans and from all of Navy Federal. Happy Veterans Day at Navy Federal Credit Union. The members are the mission. Navy Federal is insured by NCUA hey.
- [00:34]
Joel
It'S Joel and Matt from how to Money. I was just in Seattle, Matt, and honestly, it's one of the greatest cities in the world, particularly in the summer. I went on this run by the water. We hopped a ferry across Puget Sound. Just an unforgettable trip.
- [00:45]
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Joel
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Sponsor/Announcer
Find a co host@airbnb.com host I love entrepreneurship. I have been a small business owner for almost 20 years now, but it is tough to separate work from life. The business can be on your mind 24 7. So when you are hiring, you need a partner that works just as hard as you do. And that hiring partner is is LinkedIn jobs. LinkedIn makes it easy to post your job for free, share it with your network and get qualified candidates that you can manage all in one place.
- [01:35]
Joel
Here's how it works. Post your job for free or you can pay to promote share with your network. You can let your network know that you're hiring. You can even add a hiring frame to your profile picture and get two times more qualified candidates. So post your job for free@LinkedIn.com howtomoney that's LinkedIn.com howtomoney to post your job for free. Terms and conditions apply. Welcome to how to Money. I'm Joel and today we're talking. I don't want taxes to terrify you with Hannah Cole. To many, taxes are more terrifying than horror movies. Not to me. It's only because I scare easily and I completely avoid those movies. Yeah, I don't. I don't like being scared. It's not though, because I'm super comfortable with the complexity of our tax system. But my guest today, she is Hannah Cole, is on a mission to create fearless folks who launch into the world of deductions, bookkeeping, tracking, filing, and all the other terms that strike a little fear in your heart. With full confidence, her new book, taxes for Humans, well, it acts as a field manual for self employed people in particular to simplify their taxes and to take the bull by the horns. So Hannah, thank you so much for joining me today on the podcast.
- [03:04]
Hannah Cole
Joel, thanks so much for having me.
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Joel
All right, so first question out of the gate, we ask everyone who comes on. I'm so curious to hear your response. We. I like to splurge on craft beer. I think it's delicious, but it can be expensive at the same time. I'm doing the smart thing, saving and investing for my future. Right. You can do both things at once. What is, what is that thing for you? What do you like to splurge on?
- [03:24]
Hannah Cole
Yeah, well, I too like to splurge on craft beer. And I live, I live in Asheville, which is craft beer paradise, but the southern beer mecca. Oh, it's so good. But my splurge is really wonderful. Coffee out of the house every single day. Which is very against that don't buy a latte thing.
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Joel
Every single day, huh?
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Hannah Cole
Every single day. But here's why. Because I actually use it, you know, for like as a habit builder. So I need coffee when I wake up, right? Like this is, this is like a bright star to me. And so it gets me to lace on my shoes and it gets me, you know, the coffee shop is a mile away and I walk to it and so it gets me walking and then I do a four mile loop.
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Joel
Okay, so you're getting your steps in every day to get your coffee.
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Hannah Cole
Oh, I am, I am. Yeah. So it's that and it's also like, I like the community part of it. So like I fully recognize it is not cost efficient. But I really like, like that the baristas know me and that I have a little chat with them. It just like makes, makes me feel connected to my, to my city and my neighborhood.
- [04:32]
Joel
So I totally get that. We, we try to keep it to once a week, but Matt and I on Mondays will walk down to our local coffee shop and get coffee. And I, I love it. I love the walk. I love Matt and Eric. We're catching up and just kind of being out in the community talking to the baristas fellow, you know, humans in the coffee shop. It's such a lovely experience. So I get that Totally. And I don't know, maybe I'll have to up it to two days a week after.
- [04:55]
Hannah Cole
After talking to you, I feel like the common theme with all of my splurges is, like, if it makes me be social or get exercise, you know, like, because I feel like those are. Those are great. Those make my life good.
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Joel
Yeah. If it's like the little lure in the mouth, right. That gets you out there doing the things that you want to do, but you might avoid if you were just having coffee at home, that makes sense to me. You talk early on, you're an artist, and you talk about having to figure things out the hard way. And I'm curious. I think this. You might not be alone in that. Right. Where artists maybe, and taxes are not. Best friends are not synonymous in a lot of ways. Right. Where it's like, I'm great at making art. I have friends like this who are business owners, and it's like a great photographer. But when it comes to, like, running the business or doing the tax side of things, the creatives can often have a hard time. Right. So tell me about you. If you have to figure out the hard way, what did that look like?
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Hannah Cole
Yeah, I mean, I think creatives get a bad rap. Creativity is actually a synonym for resourcefulness. And, you know, because all my. Everybody I am in community with are creative people. It's. You know, what I see is that creative people are, like, actually pretty incredible at making things work on a shoestring and pulling off magic. But, yeah, the way I learned the hard way by, you know, going into my dad's accountant's office for the first time when I, you know, I got an MFA in painting. I've been a professional painter for 20 years, and I knew I needed to. I kind of knew there was stuff I needed to know. I didn't even know what I didn't know. And. And just, like, sitting down in front of my dad's accountant, he was like, so when are you gonna get a real job? I just, like, I felt so humiliated. I was like, I have a master's degree in this. Like, I have artist, you know, I know a lot of people don't know what artists do every day. It's a little mysterious.
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Joel
But I'm assuming paint, sculpt, you know, whatever it is they're into, that's gonna be part of it.
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Hannah Cole
Definitely that. Definitely that. But, like, the professional side of it, I think is pretty hard to understand. Like applying for grants and residencies. Like, how do you make the money work? Honestly, Artists don't know how to make the money work. It is. It's difficult. It's like, you know, being in the NBA, it's like the odds are not great.
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Joel
So you went into that accountant office. You got kind of sort of talked to in a. In a humiliating way. Well, how did you respond?
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Hannah Cole
Well, at the. At the moment, I just, like, my pulse was racing, and I felt completely awful. Like, all the questions I had come in with and prepared, they just flew out of my head. I couldn't even make use of that situation. And also, just, like, I was pretty organized. I had read a book on deductions before I got there because I was, you know, I was trying to do a good job, be a good student. And I had kept a mileage log. I had, you know, artists do these things called residencies a lot where you, like, it's competitive. You apply and you go to some, you know, beautiful ranch in Wyoming and paint for a month. And I kept my mileage log, like. And this was analog, like, in a notebook in the dashboard. And it was a $4,000 deduction. And he just missed it. And that was because I think he just didn't consider that I was, like, a real business. He didn't actually see my true legitimacy as a person in the arts.
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Joel
He saw it as a hobby on the side. And you're like, no, no, no. This is my job. It's a business.
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Hannah Cole
Absolutely, yes. And I think one of the real issues. And it's not just artists who face this. I think a lot of times, anybody in a career that's really underpaid, so that can be people in, like, caring fields or, you know, nonprofit adjacent areas, like, when you're. When you're not making a lot of profit. It. It doesn't necessarily look to an accountant like it's a business. And this is a really big issue. When you don't have a consistent profit, your. Your business activity can be called into question by the irs, and they can come and say, hey, is this a hobby? And just because they asked doesn't mean it's true. It's not an accusation. It's a checkup. But people don't know. You know, we don't teach taxes in high school in this country, though I think we should. And so people just don't know what their rights are and their responsibilities. And so it just feels like all fear and no empowerment. So I just really want to partly be here to witness those people who are in those, like, caring fields and the humanities, people who weren't in those like, well resourced STEM departments in college.
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Joel
The engineers will be fine.
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Hannah Cole
I know.
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Joel
Take care of themselves.
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Hannah Cole
I mean, it's hard enough, it's hard enough when you sort of didn't get all those resources and so you need them. But then you also feel this sort of like shame and fear about the people you're working with, the accountants, because they really like, they're not used to working with people like you and they don't feel, feel like they get you.
- [09:45]
Joel
Yeah, well, I think that taxes course should be side by side with the personal finance course. I mean, those are two things that we're gonna use for the rest of our lives and what like half of states finally do now require it in high school. But yeah, it's. There are so many things we learn in school that are lovely and beautiful and maybe we don't use them for the rest of our lives and maybe they were still worth learning. But my goodness, personal finance and a little bit of tax knowledge would go a long way to help the, the average American. The tagline of your book is, and I love this, simplify your taxes and change the world when you're self employed. That's a big promise, changing the world. So tell me more about that.
- [10:26]
Hannah Cole
Yeah, so it's kind of a secret agenda inside my book that I feel like a lot of people who are really passionate people in the humanities, people in creative fields are often really good agitators, activists, they're like people who really move the culture. That is what I think is so important about creative work. You know, it's really hard to advocate for a fair equitable tax law if you just have no idea how tax laws are made in the first place. And so I just feel like if I'm going to do the work of getting people up to speed on how their taxes work and sort of where they sit inside the tax code, I'm going to go the extra mile and be like, and here's what a fairer way to do it might be. Hint, hint, call your senator.
- [11:15]
Joel
Well, yeah, I mean, I think some people assume that the way the tax code currently exists is the way it's always been. And that's far from the truth. And in fact, and I want to get to this later, but a lot of recent tax legislation over the past few years is making a big difference in who pays what and also in our national debt and deficit. I'm curious though, I want to start in a place of optimism here too, because there is a lot of pessimism about an individual's ability to start a small business and to do well in this country. But you're far less pessimistic on that. Can you maybe give me a little bit of an overview of why you think the United States is still a great place to start a business?
- [12:00]
Hannah Cole
Oh my gosh, I love this question. And yes, I think hope is important and we have a lot of good reason for it. You know, like 44% of all Fortune 500 companies were started by the children of immigrants. I mean, like, just think about what that means. People are coming to this country for the opportunities that we provide for businesses. Like, it is a great place to start a business. And I think a lot of people who are self employed don't even realize that they are considered a business under US tax code. So an Uber driver, you know, person just getting paid 1099 versus on a W2. Right. That's a business person. But often that person, you know, because of a lack of education perhaps they just don't know. They don't know that they could be keeping deductions and getting a lot of benefits, you know, because the fact of being paid 1099 means you get to take expenses of running that business as a deduction on your taxes. So there's just like a lot of benefits. Really, really generous, wonderful encouragement to invest in yourself when you are a business, even at the tiniest little micro level. And I just want more people to be aware of that. I think, you know, if you went to business school, you know this, right? But if you went to art school, maybe you don't. So I want everybody to know.
- [13:24]
Joel
You even say, you say the tax code is built to give you a financial boost as a new self employed person.
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Hannah Cole
It absolutely is.
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Joel
So talking about that, for someone who's like, I was afraid to start a small business because I've heard maybe some rumors about how taxes work as a self employed individual. Well, you're saying that the opposite. Like it's not harrowing, it's actually potentially some wind at your back.
- [13:46]
Hannah Cole
I love that. Yeah. I mean, and rumor is a lot of how we understand taxes here, right? It's rumor and not factor, but you're right. So one of the incredible benefits of having what's called a schedule C, that's a tax term, but it just, it's the part of your tax return where you put the business income and the business deductions. So when you're self employed, that's where you're reporting your income and your tax return. But one of the benefits we all kind of know that we get deductions. But the thing that people don't realize is you also have the ability to take a loss. So a schedule C, if you look at the title, like on the top of that form, it says profit or loss from business. Not just profit, right? So the loss. I know this is very counterintuitive, but if you, you know, every business, if you think about it, every single business starts in the negative because expenses come first, right? So if you think about like a pizzeria, right? So if you start a pizzeria, you. You cannot make a single dollar, not even profit, but just like a dollar in the door until you have set up a pretty fully operational pizzeria, right?
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Joel
You need an oven, signed a lease, bought pizza ovens.
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Hannah Cole
Exactly. You need an oven, flour, a baker, you need a storefront. And so you can't make a single dollar from selling a pizza until you have the full ability to make the pizza already in place, right? So you bought the oven, paid the rent, paid a baker, bought the flour, right? All of those things. You have to spend the money first. And it might take you some time before you sell enough pizza. Get a reputation, get your advertising going, get word of mouth going, maybe get, I don't know, reviewed in the local newspaper by the local Instagram influencer or whatever. But it might take a little while to actually get enough money coming in that you break even, right? That's the moment where you actually even. That's not even the moment you're profitable yet. It's the moment where your expenses and your income equal out and it's zero. So being able to take the loss to report a negative number on your taxes is a tax benefit, because what it does is it actually that negative number is added to your other taxable income. And so if your spouse is earning money with a day job, your negative income will subtract taxable income off the spread spouse's income that you jointly pay taxes on. So in other words, it'll save you thousands of dollars in taxes, which is deliberate. That is meant to help you through that delicate baby investment year of your business.
- [16:24]
Joel
So is that part of the IRS's goal to ensure that we have a nice playing field for small businesses? It's like their goal is to see small businesses succeed. And if they can't report that loss and use it against other income, then it's really hard for a small business to last if they're, you know.
- [16:43]
Hannah Cole
Absolutely. It's very. And the first year of business, when you have all those expenses and you don't have income yet. That is the hardest year of business, right? There can be other hard years. I mean, I'm, I'm coming to you from Asheville and we had a real hard year last year when Hurricane Helene destroyed a lot of businesses, including my studio. And so that, that loss, you can take a loss later if something like a Hurricane Helene comes and destroys your business. You can have a loss in a, in a later year when you thought you had every reason to believe you'd be profitable. But I think the thing to think about is, like, when you're a small business, you're growing the gdp, right? And that is one of the chief aims of the US Government. So they want that, they want you to grow, they want you to have more and more and more profit, maybe hire people, spend a lot of money in the economy and eventually pay taxes on that profit. So it's not like charitable. They're just like, this is good for everybody. We want you to win.
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Joel
Tell me a little bit about the Hurricane Helene and what you learned as a small business owner in that. Obviously, just the pictures, the devastation going, going to Asheville, even in March, like, I could see a lot of the devastation still. You know, logs and trees everywhere still. But what was that like for you from a business owner perspective? How did you get through that? What did you learn in that process?
- [18:03]
Hannah Cole
It certainly made me lean on community. There's this sort of, you know, we perpetuate this myth that we're all alone in this country, the sort of cowboy culture thing. And, you know, there's nothing like having your water go out for five weeks to make you realize that you are very dependent on your government and that government being functional and well funded. You know, I wanted my water. All the business, all the restaurants couldn't open because they had no water. And my kids were out of school because there was no water. There was no way to flush a toilet in the school. So for certain it was like, oh, tax dollars going to pay for infrastructure that brings clean water. And also just like a resiliency plan. I was really happy that we have electeds who had some resiliency planning already in place, some forethought that was, that was really great. But also rebuilding is really hard and really slow and the media is here for, you know, maybe a month and then it's gone and you are still in it. So that's, that's a hard part. Anybody you know, if you were in the LA fires, if you were in the Texas Floods, I mean, anybody who's been through it knows that when the media goes away, it feels lonely.
- [19:15]
Joel
Yeah, I believe it. Yeah. There's a spotlight for a minute and then they all, they all leave. And then you're still left for many months, often years, kind of cleaning up and trying to get back to normal. Yeah, I'm curious too. You mentioned the difference between like a hobby and a business. And can you maybe the IRS has like, specific guidelines about that? Right. So it's not like you, you don't necessarily say, I think I'm just a hobbyist or I think I'm a business owner. How is that defined?
- [19:43]
Hannah Cole
Yeah, there's a real definition, and it's actually not at all what people think the definition of a business versus a hobby is. A business has a profit motive. Those are IRS words. It's important to note that having a profit motive is different from having a profit. Like if you think of that pizzeria, the year that they spend the money on the oven in the storefront and they don't have customers yet, like, that doesn't make them a hobby. Right. They're a business that's just not profitable yet. So that's really important to know that a legitimate, profit motivated business can still have losses. That's important. But a hobbyist does not have a profit motive. They're doing it for fun.
- [20:23]
Joel
Okay, so, and then how. How do you know when a small business or what, maybe it has been your side hustle, but you're like trying to profit from it. You want this to become a business. How do you know when that business needs to be incorporated? I think this is one of those tough decisions that people like trying to wade through the Alphabet soup of letters and they're like, I don't know, what should I be? Should I be an S corp? I have no idea.
- [20:52]
Hannah Cole
Yeah, yeah. There's some tricky things there. What's important to know is that there's different order of operations. Like the start time of the various things can be different. So what I mean is you're a business to the IRS before you're a business anywhere else. And that makes sense because the IRS is the tax collector, right? Like, they're there to be like, hey, okay, the minute you earn a dollar back, like, we're going to be here. We would like the taxes on that. Right. So you're already a business to the irs. Now, a lot of people, I think because of like Internet and the rumor of how business stuff works, it's like they think, oh, I might maybe need an llc, maybe I need an S Corp. So just to clarify what those things are, the LLC is a legal entity and it's about a liability protection. So that stands for limited Liability Company. And what it does is stick a shield in between your business assets and your personal assets so that if you get sued, only the business assets are subject to the lawsuit. So that's the purpose of an llc. It's not required that you become an LLC to be a real business. Not at all. In fact, you might be wasting your money if you're not. If you're not at any risk of a lawsuit. If you're, if you have no personal assets, you know, it might. It's possible that you don't need to waste money on llc.
- [22:16]
Joel
And the cost of an LLC can vary significantly state to state. In some states you can be like 100 bucks. And then some states it can be 800 bucks, 1,000. It can just be more, a lot more.
- [22:25]
Hannah Cole
Expensive, Very much. And then the S Corp is. So the LLC is a legal entity, it's actually not a tax entity. So one of the interesting things is that the irs, if you're just a single owner of the llc, that's called a single member llc, the IRS disregards it. So it actually has no bearing on your taxes. A lot of people think the LLC is going to change all their tax stuff. It actually doesn't at all. That's the thing to know. But an S Corp is actually a tax entity. So unlike an llc, it's totally different. And you can have both. You can be an LLC and an S Corp. Like I actually am. Sunlight Tax is both an LLC and an S Corp. My biggest thing that I want to tell people is like, just don't form it too early and check your state rules because, you know, someone on the Internet might be talking about how you're going to save all this money when you form an S Corp. Well, if you're, if you're living in New York State, New York taxes back all the benefit you get from an S Corp. So you're wasting your money. You're literally lighting money on fire.
- [23:26]
Sponsor/Announcer
So.
- [23:26]
Hannah Cole
So you just have to be careful when you're getting.
- [23:28]
Joel
It's just a state specific thing. And you need to know what your state's tax rules are in order to kind of know what designation you should be choosing.
- [23:36]
Hannah Cole
Yeah. And in the book I have a chapter on these sort of setup issues like LLC and S Corp, and I have a list of the states that have rules that sort of tax back. Some of the benefit of an S Corp. Definitely check which state you're in in the state rules before you go spend the money cause you might be wasting the money. Grant you if you're in a state like North Carolina, great. S Corp can be great.
- [24:00]
Joel
All right, we've got I've got more to get I want to get to with you and I want to talk specifically about maybe some of the systems we need to set up as a small business owner and then also kind of some of the recent tax law changes that have been made and how those are going to impact us as as self employed individuals and just really everyone who's listening too. We'll get some more with Hannah Cole right after this.
- [24:26]
Sponsor/Announcer
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Joel
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Joel
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Joel
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- [27:13]
Joel
All right, we're back. We're still talking with Hannah Cole. We're talking about taxes. They can be terrifying, but Hannah is demystifying them so well in her new book and I'm excited to continue this conversation. Let's talk about running a business. Hannah, this is something you do address as well on your blog and in the book. A little bit like the systems that we need to streamline in order to make taxes less of a bear. And I do think a lack of organization is probably a big part of what makes taxes so frustrating for people. They're like trying to go back to all these different folders on their desktop or items that have just been dropped and dragged random places, little folders inside of their email inbox. So can you talk about the systems that need to be streamlined and maybe offer some best tips for getting organized?
- [27:58]
Hannah Cole
Yeah, absolutely. I mean, one of the key things to realize about taxes is that they're retroactive. So no matter what, just the mantra to have is like, don't hate yourself because things got messy. Like that happens to everybody. But just start now. Start now. So the systems that you need, you need receipts, you need tax documents, and then you need bookkeeping. Those are the three key systems to get your taxes. You know, organized receipts is like a five minute task. It's like almost nothing. All you need to do is just Keep them. Right. And they actually go in cold storage. Because the purpose of a receipt is actually just in case you're audited. You don't actually need to use the receipt unless you're audited.
- [28:42]
Joel
So taking pictures of those receipts or just having a digital record of it is good enough.
- [28:47]
Hannah Cole
Totally fine, as long as it's legible, like, and as long as you can access it. So audits can come, you know, as far, you know, as late as six years later. That's a little rare, but it can be. So we say keep receipts for seven years for that purpose. Just make sure, you know, if you sell your computer, you know, you want access to the files, you don't want to digitize it, and then, like, stop paying for the, you know, receipt capture software and then lose your access.
- [29:12]
Joel
Gotcha.
- [29:13]
Hannah Cole
But as long as you have it, digital is fine.
- [29:15]
Joel
Okay.
- [29:16]
Hannah Cole
But you don't need to be sorting receipts. Sorting receipts is just a complete waste of time. And I. Everybody listening, I dismiss you. You don't have to do it.
- [29:23]
Joel
And then tax documents, are you just. Are you taking. Digitizing those and sticking them in a folder so you can. Or how are you handling those?
- [29:31]
Hannah Cole
Yeah, so, I mean, most of us get a mix of digital and physical tax documents, you know, and to do your taxes is going to be. I find it helpful to get them all in one format. So for me, that's digitizing the paper ones. You know, the tax document thing is something you really only have to worry about at the beginning of the year. Those will tend to roll in mostly by February 1st, but there are some that will come late. You know, your brokerage statement, if you're investing, which I hope listeners of this show are.
- [29:57]
Joel
Me too. They better be, or I'm coming for them.
- [30:03]
Hannah Cole
Yeah, that's the point.
- [30:04]
Joel
Right, Right.
- [30:04]
Hannah Cole
But just dedicate one place in your house to keep your tax documents, you know, as you get those important, you know, letters in the mail from. With the tax document stuff. Just like. Is it your sock drawer? Is the top drawer of your desk. Just whatever it is, just have a place and just everything. Make sure you have religion about those documents. Go in that place. And then when they're all there, then you can go through and digitize the paper ones. That's how I do it. And I think it. It works pretty well.
- [30:31]
Joel
When we're talking about receipts, oftentimes we're talking about receipts for expenses. Right. That the business has incurred. Can you talk to us a little bit about deductions? I think they're still just so Much confusion right in the deduction space. And. Yeah, yeah. How should a small business owner think about deductions, like meals, what counts, and at what percentages?
- [30:53]
Hannah Cole
So deductions for your business are really generous. That said, there's a few. There's a couple outlier people, and some of them are sort of loud on the Internet who just try to deduct everything in their entire life that is not quite legit. But if it is ordinary and necessary. Those are IRS words, ordinary and necessary for running your business, then it's deductible. So this will include, like, mileage for driving your personal car to, you know, a business meeting. It includes a meal. You know, Joel, if I. If I were to buy you a beer and to talk about this podcast, and, you know, you coming onto my podcast, that would be a business expense. Those are actually. That sounds fun. Let's do that.
- [31:34]
Joel
It does. Let's go. I'm in. I'm in. You don't have to twist my arm.
- [31:40]
Hannah Cole
So those. Those things that you need to do and, you know, and if you think about it, a lot of businesses through relationship building, so meals, travel, we travel for business so that we can meet people face to face and establish that, like, warm human connection. So, like, it's kind of fun and awesome to be able to deduct those things for your business. You just want to be careful to follow some more tricky rules in those areas that people, you know, might tend to abuse, like meals, like travel. You want to lock it in and make sure you're following the rules, because those are the most frequently audited categories.
- [32:12]
Joel
Okay. You know, talk to me about small business owners paying themselves and then also when it makes sense or when it's necessary to start paying quarterly estimated taxes. So typically now you're beyond the stage of starting losing money. Right? Like, you're making money like, how do I pay myself? And start paying the taxes in advance? Because that's what the IRS requires.
- [32:38]
Hannah Cole
Yeah. First, just the paying yourself thing. Something that people get confused about is, you know, when you are. When you have a Schedule C, which is where you start right before you form something like an S corporation, everybody's got a Schedule C. On a Schedule C, paying yourself is not a deduction. So even though it might be a good idea and a good business practice, and it is, it's still not a deduction for your taxes. So that's just important to know. But with that said, it's good to get in the habit when you have consistent income. It's really good to get into the habit of making a transfer from your business account to your personal account. And let me just pause on that because, yeah, having a business account is really important, too. That helps your bookkeeping, that helps your record keeping, and you want to do all your business deduction spending through that account. Because if you think about it, then your book, your bank statement for that business account is going to become the backbone of your bookkeeping.
- [33:36]
Joel
It's a firewall of sorts.
- [33:38]
Hannah Cole
Absolutely. And it makes everything simpler. And then later, if you decide to get an llc, that separate account is absolutely mandatory because that is part of you maintaining that legal separation between business and personal.
- [33:51]
Joel
Okay.
- [33:51]
Hannah Cole
But with that said, it's totally fine to transfer money in between them. That's normal and fine for a business here to do. You just want to know that, you know, in your accounting, when you put money, when you pay yourself, moving money from your business account to your personal account is called an owner's draw. That's actually how you classify it in your bookkeeping. And you can actually go the other way. You can invest in your business. You can move money from personal into your business. Maybe I want to buy, you know, maybe I'm a podcaster and I want to buy a big new, like, gorgeous mic and like, you know, do a renovation of my room with soundproofing, right?
- [34:26]
Joel
Yeah.
- [34:26]
Hannah Cole
So I can put money and maybe I don't have the cash in my business account. I can do an owner's investment from personal into business and put it in my business account and spend the money there. Because you have the right as the owner to invest in your business and also to take profits from your business.
- [34:42]
Joel
Okay.
- [34:42]
Hannah Cole
But the thing to know is that even though that's happening, it that is not reported on your taxes. So when I put money in for my podcast studio, that's not going to be income to my business. So I don't have to pay any taxes on that. That's the good news. The other side of that is that when I pay myself, it's not a deduction either. So it just doesn't count. Yeah, just doesn't even touch it.
- [35:05]
Joel
Let's talk about recent tax law changes. What's been called the Big Beautiful bill made a bunch of tax changes. Can you maybe highlight some of the big ones and should they be changing our approach to taxes as individuals or as business owners?
- [35:21]
Hannah Cole
Yes. So let me just say that this bill is enormous. There is so much in it. I like to have the stats at the tip of my tongue, but it's so big that I find this difficult.
- [35:32]
Joel
Wouldn't it be nice if legislation was bite sized and easy to understand?
- [35:36]
Hannah Cole
Well, I have, you know, in my podcast, which is the Sunlight Tax podcast, I have been breaking down the bill by topic. So I did one on like the expiring energy credits and I did one on healthcare. In fact, tomorrow I'm interviewing like a healthcare expert. So I am trying to do the bite sized version. But basically there's big changes to health care. A lot of the energy credits that were available under the Biden administration have expired, Some have already expired and some are set to expire at the end of the year and some next June. I guess the way that that bill was designed and you know, this is sort of typical, there's some sugar rush up front to make people like the bill. I mean, the legislators want people to feel that it was a good thing and then there's some consequences that don't actually kick in until a little longer term. Most of the health care, you know, people losing their health care, that is sort of going to kick in around 2027, 2028. So people aren't going to feel that stuff right away. But there are big, big changes to healthcare like HSAs. You explained this on your Friday podcast.
- [36:44]
Joel
I think HSAs are more widely available to people on bronze plans who signed up through healthcare.gov which is, that's a great thing. Right. So there are some lovely changes and.
- [36:57]
Hannah Cole
Then there are some lovely changes and.
- [36:59]
Joel
Then there are also some things that are just harder. But like is there anything as a small business owner, for instance, I was reading something about why people are buying private jets now because of, because of the ability to deduct that and, or depreciate that asset fully in a single given year. Right. So is that, is that like something that small business owners, I mean most people listening still won't be buying private jets, but anything for there in that for small business owners to know about.
- [37:27]
Hannah Cole
Well, a lot of the benefit of this current legislation is actually just keeping in place benefits that were established under the First Trump, the TCGA, the Tax Cuts and Jobs act of 2017. So things like the QBI deduction, the qualified business income deduction, just quick primer on that. The rules are a little more complex but short version is you get a 20% deduction on your business profit and that's a nice little bonus for small businesses. People with a schedule C, you know, Uber driver side hustler, you count, you get this deduction. I don't think it feels like a revelation when you get Something that you've had for the last five years. Sure, you just continue to be able to have it. But that actually is the news because those were set to expire at the end of 2025 and they actually just all got extended, which is interesting too.
- [38:24]
Joel
Because in the way the legislation was done, so many of the things that were kept around and the changes, many of them are set to sunset in 2029. So from a tax planning perspective, how does that impact, how do you think that impacts small business owners?
- [38:43]
Hannah Cole
Yeah, you know, it's really hard to predict the future. I think you probably teach this as you teach investment too about timing the market. It's just, it's hard to know what is going to happen. We can guess, but nobody knows the future. And it's important to know that nobody knows. There's no expert who can tell you. But I will tell you this. One of the effects, like really big effects of this legislation is a massive explosion in the federal deficit. And because of that it is going to mean that it crowds out the ability to spend money on programs, you know, social safety programs. Like that is simply going to happen because we're going to have such a large debt that it needs to get serviced and the interest paid on it so that we can continue to have credit as a nation.
- [39:33]
Joel
So I think these are bigger topics.
- [39:35]
Hannah Cole
These are definitely bigger topics. But really I think an important thing maybe to understand is one, you probably will get less benefits from the government. Like that is probably going to happen. They're probably going to be some pretty ugly cuts that, that have to come in 2029, 2034 especially. Ten years out is a long time. And also I would expect tax rates to go up in the future at.
- [39:57]
Joel
Some point in the future.
- [39:58]
Hannah Cole
Yeah, I think that's, that's one that is the most likely.
- [40:01]
Joel
I don't think you're alone in that prediction. And actually when they were forming the bill that was one of the things that was discussed was raising that tax bracket in that very upper echelon tier of income earners. But that was, that was not done. Yeah, I'm also curious just from like a general tax filing perspective, you are all about empowering people to DIY to understand the tax code so that they can DIY their taxes. Can you make the case to me and to our listeners for why a self employed person should not hire a pro, maybe why they should figure this stuff out and learn to do it themselves.
- [40:38]
Hannah Cole
I feel frustrated personally and you know, as a taxpayer that I have to pay to perform My civic duty of paying my taxes, that just feels wrong. And I know because I've looked at other countries, like other countries don't all do it that way. It doesn't have to be that way. And so it just feels to me, honestly, just like as a civic right, it just feels like we should be able to just pay our taxes for free without paying a third party. And I think those companies, they use a marketing method that is to just make us all feel really fearful and a lot of dread about the IRS and about tax law and just say like, hey, it's so complicated and so scary. Just pay us and we'll do it for you. But actually a lot of stuff you don't need, you're probably doing most of the work on your own anyway when you do pay someone. And so if you just knew a little bit more, you'd be able to file the taxes on your own. And so to me, you know, it's kind of against my own interest, right. Nobody's going to pay me to do taxes now. But I just, this is a book I wanted to, to exist in the world because I just think this is fair and they just want people to be able to do their own taxes. With that said, I do have a chapter in the book that I think is an important one, which is about tax triage because there are some scenarios that just have complexity. If you go buy Joel a corporate jet for yourself, the depreciation might be a little complicated.
- [42:02]
Joel
When you say if I've already done it.
- [42:04]
Hannah Cole
So is that your craft beer splurge?
- [42:08]
Joel
Yes, yes. Now you know, when you get to the upper echelon like me, corporate jets are necessity, right. When does it become complex enough to need? Like for instance, I'm a real estate investor, right. And that owning multiple rental properties does complicate things. But you're right, Like I'm gathering a lot of that information anyway to give to my tax professional to then do the actual filing. And then, and then when it comes to making like not just year end decisions to try to save on some taxes this year, I think sometimes having the input of a tax professional who is like up to speed on the changes in the most recent tax bill, like that, that can be helpful from, hey, here's like what changed and how it's impacting you now and then also how you should be thinking about your taxes, how much you're contributing to like donating maybe bunching donations to maximize a tax deduction this year versus, you know, donating equal amounts in over multiple Years. Like, there are some complexities like that and people could save more on taxes, but maybe they just don't know that that exists or know how to go about it.
- [43:20]
Hannah Cole
You're absolutely right about that. And there are things. Tax planning is something that actually costs a lot of money but is worth it. I actually think that. I think of that almost differently than just tax preparation, which is not always worth it because you often do have to do most of that work yourself and could just get over the hump with a little extra info.
- [43:40]
Joel
Yeah.
- [43:41]
Hannah Cole
So my book, really, I. The people that I was thinking of are like, you know, me, younger me who was like an artist with all the complexity of a larger business, but not the income. And younger people who tend to have, you know, a young person recently out of school in their first job or in their first, you know, just starting their business for the first time, that's a person who hasn't accumulated a bunch of real estate, maybe a spouse, maybe a mortgage. Right. That your taxes are simpler when you're younger. And so a younger person who has a much more limited budget, who's listening to your show to get all your amazing tips on that stuff, that's the person who needs this book and who need, you know, needs to be able to just do their taxes on their own because they actually probably have a simpler situation.
- [44:27]
Joel
Yeah.
- [44:28]
Hannah Cole
Once you do have multiple real estate investments and, you know, a marriage and a mortgage and depreciation and all these things like those, that's where one, you have the resources, you have the money to pay somebody professional and probably more need for it.
- [44:43]
Joel
Yeah.
- [44:43]
Hannah Cole
So it's that, like, zone of people, I think, who've been left out, who are paying 300 to TurboTax when they have really a very simple tax return. That's who I'm really trying to talk to.
- [44:54]
Joel
Yeah. I love that you kind of distinguish too, between paying for advice and paying for someone to file your taxes on your behalf. And especially for people who have. Yeah. Simpler situations. There's. There are free tax software like I have always liked. I think it's Cash App taxes now used to be done by credit Karma. And they have. You can file your federal and state for free, and you can even have greater complexity than some of the major tax softwares that are like, well, if you meet this, like, tiny, you know, people who have a 10 can file a 1040 easy, then we'll let you file for free. But Cash App taxes opens it up to a wider array of people who can file for free and DIY it. But yeah, I think paying for that advice and insight maybe, or even just like buying your book and then like learning it, downloading the information that way can make people feel more confident in their ability to kind of go the DIY route.
- [45:51]
Hannah Cole
Yeah, I think, you know, honestly, I just want people to have a better sense of what their rights are. And because I find when people have that information, they feel much less scared. They're really made for humans. They're made for people who are imperfect, which is literally 100% of us. The only really hard and fast rule about taxes is meet the deadline.
- [46:14]
Joel
Right.
- [46:15]
Hannah Cole
But if you make a mistake, you can file an amended return. Like, they're actually more forgiving than. I mean, you have to follow the rules and do your best. I'm not saying cheat on your taxes. Definitely not. But like, you can fix mistakes. You can arrange payment plans. There are ways to get out of a bad situation. And I just want people to have the information so that they can kind of go in eyes wide open and not just pay money out of fear.
- [46:40]
Joel
Yeah, let's talk about perfection and a few other quick topics. Hannah. We'll get to just a few more questions with Hannah Cole right after this.
- [46:52]
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- [48:42]
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- [49:17]
Joel
Do not let financial opportunity slip through the cracks. Use code how to money@monarch.com in your browser for half off your first year. That's 50% off your first year@monarch.com with code how to money. All right, we're back. We're still talking with Hannah Cole. We don't want taxes to terrify you getting towards the end of the year and taxes are, you know, starting to get on people's minds where whether it's last minute moves to potentially reduce taxes for next year, whether that's contributing more to those tax advantaged retirement accounts or, you know, donating more money, which you have to be thoughtful about that too. Like I just mentioned with the bunching, is donating more money going to actually get you a tax break this year? It depends on a bunch of things. But what you were just talking about, Hannah, right there, I think a lot of people feel like their taxes need to be perfect before they file. And that feels like an impossible thing. Like what does that even mean? What is the IRS really looking for from us when it comes to avoiding getting audited and making sure we're jumping through the right hoops?
- [50:21]
Hannah Cole
Well, nobody can promise you not to be audited because it's the only check and balance in the system. And so that is that they have a right to audit you at any time for the last three years. But even though that sounds a little scary, the thing is, the thing that I think people don't really consciously think about with taxes is that you have to pay taxes all year. And it's an estimate. And the whole job of a tax return is to reconcile the estimated taxes that you paid, whether it was through withholding on your paycheck or through paying estimated quarterly taxes, which is how you have to do it when you're self employed. And so you do that estimated payment all year. And then when the tax year is over, so December 31 goes by, then you get those tax documents in the mail, you do your bookkeeping, you see what the actual was versus the estimate. And the tax return's job is to say, oh, you overpaid your taxes, here's your refund, or you underpaid your taxes, here's your bill. And so if you think about that, perfection is not in there at all. Estimates are imperfect and reconciling is part of the process. So I hope that just feels like diffusing to this idea. Like it has to be perfect. No, like the tax return's job is to do the math on that, you know, to make change on those final numbers. That's all.
- [51:39]
Joel
When people come to visit you or in the process of writing this book, as you're talking to people, what are the biggest misconceptions that people tend to have about taxes? Like, what are you maybe trying to combat fiercely here that people believe that's maybe not true?
- [51:53]
Hannah Cole
I mean, one is that they're super scary. I mean, because I really do find, I do a lot of workshops around the country just teaching people about taxes. And I find consistently people come up to me after and they're like, oh, I totally feel like I can do it now. Yeah, just, you're right.
- [52:08]
Joel
I mean, even my intro, you heard my intro. Like, it's fear based. Like, there is a lot of, like, I don't like horror movies. Like, that was not. That's, that's not a joke. Like, I get scared, but I think taxes have a similar, like people feel that way about like even just the word getting spoken in a room.
- [52:24]
Hannah Cole
Absolutely. Well, as a person who has called the IRS a lot, because before I knew, you know, before I went back to school for accounting, I myself got in trouble. Like, some of this book is written based on my own pain, but just as a person who also calls the IRS on behalf of Clients, they're so nice. Like, nobody, nobody you talk to in bill collection in any other private area is ever going to be as kind and sort of forgiving as the irs. They just want basically for you to pay your taxes in any way that you can. Yeah, it's not actually so terrible.
- [52:57]
Joel
Well, I was going to say maybe some of the things that will get you in the most trouble is like not filing right like that. Maybe talk about how big of an issue that can be.
- [53:07]
Hannah Cole
And actually, you know, you were asking like one of the most, you know, the things that people get wrong, thinking that estimated taxes, estimated quarterly taxes don't apply to me or that I'm going to get some written in stone engraved invitation to start paying estimates like, no, I wish everybody had this education and I'm trying to provide it in this way book. But estimated quarterly taxes apply to you if your tax bill last year was over $1,000. So, like, you can actually look, that's a knowable number. You can pull out your 1040 from last year, look at that tax, you know, amount you owe, line. And you can see, you can see the answer. If it's greater than $1,000, you have to pay quarterly.
- [53:50]
Joel
What happens if you don't pay quarterly estimated tax?
- [53:53]
Hannah Cole
Yeah. So if you don't pay quarterly taxes, then the following year, when you do your tax return for that year, year, you'll be assessed up to four penalties for each of the quarterly deadlines that went by that you missed. Right. So you might pay four, you might have four penalties. You could only have three if you figured it out and paid your last payment. Right. So you can stop the penalties by getting on board the train. And then there's also daily interest. And of course, like, you know, that's a. Penalties and interest are an incentive, a negative incentive. So the incentive with the daily interest is to say, hey, okay, you missed the core quarterly deadline for, you know, January 15th. But if you get on board and make your payment before the don't wait till the next quarterly deadline, pay tomorrow, pay today, it's always going to be more cheap to pay your taxes today than to wait till tomorrow.
- [54:42]
Joel
And what's your advice on how people can figure out how much they should be paying in quarterly estimates to the irs?
- [54:49]
Hannah Cole
Yeah. So there's two rules called safe harbors. And your goal as a taxpayer is just to meet one or the other of them? It can be either one. The easy one is paying 100% of last year's tax this year. So if you just look at the Total tax line on your 1040 summary. That's the page. It's on the page that has your signature. There's a line that says total tax. You take that number divided by four. That will be a good baseline for meeting the first safe harbor rule for paying your estimates for this year. So if last year, for example, my total tax was $20,000, I'm going to take 20,000 divided by 4 because it's quarterly taxes, and that's a $5,000 payment each quarter. And that will meet the safe harbor.
- [55:35]
Joel
For me, which is great for not running afoul of the irs. But if you make a lot more money, you could still find yourself short shrift at the end of the year when it comes to. Or when it comes time to file taxes and having the money to pay what you actually owe.
- [55:48]
Hannah Cole
Absolutely. And I think that that is the hardest part for people to realize. I think a lot of times people get their head around the retroactive part of taxes. They look at last year's tax return because that's the only one they've got, and they can get a handle on last year. But meanwhile, this year is happening, right? And this year's taxes are not actually going to be based on last year. They're actually going to be based on this year. So the IRS lets you estimate based on last year with the assumption that this year looks like last year, but sometimes this year doesn't look anything like last year. And so that's where it gets much more tricky. There is a safe harbor rule that helps you. You can pay 90% of this year's tax, but you know, you're paying 90% of an unknown total, so that's much harder to get your head around. I'll tell you the cheat code, though, Joel. It's just you have to do bookkeeping once per quarter.
- [56:42]
Sponsor/Announcer
Okay.
- [56:42]
Joel
And that's how, you know, maybe we'll end there. Bookkeeping is. How difficult is that? And I know that there are so many. It's funny, we do it ours in house. Matt, my co host and best friend, loves to do it. He just is thrilled to do our own bookkeeping, which is rad.
- [56:59]
Hannah Cole
God bless.
- [57:00]
Joel
I know, right? But then there are these bookkeeping softwares out there that seem to be relatively inexpensive. So is it pretty simple to use those for small business owners? Is that typically the best solution?
- [57:12]
Hannah Cole
I honestly think the best solution is the one you're going to stick with and the one that works for you. You know, like, if it's really complicated to set up and expensive and you don't have the money, maybe that's not the best one for you. You can absolutely do your bookkeeping on a spreadsheet. There's nothing wrong with that. Just understand a spreadsheet is going to be manual. Right. It's not going to pull a feed from your business bank account and start putting those into categories for you. If you want some of that automation, it's going to be worth it to pay for some software. So yeah, you really, I think the number one thing to think about if you're going to pay for bookkeeping software is one, if you're not paying, you're being sold. You are the product you're being sold. Right. That's a thing to know. But you want to look for the automation of pulling in your bank statement. So if your bookkeeping software won't play well with your bank, and I've had this happen, I use Fidelity and I tried to set up on a bookkeeping platform that wouldn't pull a Fidelity bank statement and it was a waste of all my time and all my work. I was like, oh, this is going to be manual anyway and I'm paying for automation that I don't get. So that's what I would look for.
- [58:25]
Joel
Okay, wonderful. Hannah, thank you so much for taking the time today. Where can how do money listeners find out about your awesome new book that demystifies taxes and makes it all just super reassuring to know that you can do it yourself?
- [58:38]
Hannah Cole
Thank you, Joel. It's so fun to be here. Yeah. The book Taxes for Humans is available anywhere books are sold. And if you go to my website, I made a page for how to money listeners you can go to sunlighttax.com how and you can, you know, get a link to buy the book at any independent bookstore or your favorite, you know, large retailer.
- [59:00]
Sponsor/Announcer
Amazing.
- [59:01]
Joel
We'll put that link in our show notes too up on the site@howtomoney.com awesome.
- [59:05]
Hannah Cole
Can I also tell them tell you that you know on, on my website@sunlighttax.com I have a visual guide to tax deductions for small businesses and self employed people. So that's a really cool free download for those like visual learners among us with all the tax rules written out. So if that if anybody's interested in that, sunlighttax.com is a place you can get that tax.
- [59:26]
Joel
Wonderful Hannah, this has been great. Thank you so much for joining me.
- [59:29]
Hannah Cole
Thanks for doing this, Joel. It's just awesome to talk to you and I love what y' all are doing over there.
- [59:33]
Joel
Oh man. Such a great conversation with Hannah Cole. I just, I love it when somebody has the ability to talk about something that most people feel where it feels like another language. And I think for a lot of people taxes feel like another language. And this is why we spend so much money hiring other people who understand that language to do tax work for us. Right. Is because we don't want to take the time to duolingo taxes. We just don't. And so we pay the price one in terms of not understanding how they work. And maybe so I think the price gets paid many times over. Sometimes it's in the deductions we don't take or maybe it's in the fact that we don't really understand that we're a business. And so we're not paying those quarterly estimated taxes which costs us, like Hannah was saying, in terms of interest and penalties. And, and then it also costs us when we pay the professional to, to not just file our taxes, but maybe we're paying for advice as well. And so there, there can be a lot of money sunk into paying for tax help. And it's not that it's never a good idea. Like we even talked about the complexity of being a real estate investor. And especially once you get past a certain point, maybe it makes the most sense for you from an ROI perspective to hire someone to help. But similar to, I just think, I always think of this as a real estate investor when you are getting started out, we always talk about not hiring someone to manage those properties for you because there is something about the, the learning curve of at least diying it for a couple of years that's going to be really good for you. You're going to have your this hands on approach. Yeah. It doesn't mean you're fixing everything that goes wrong at the house yourself, but you're managing the tenants, you're finding tenants, you're learning what it looks like to be an effective manager. And then when you do hire a manager in the future, you have a lot better understanding and knowledge to hire a good one. You know what questions to ask, you know how to hold them accountable. And I think the same thing is true of, especially in those early years, diying your taxes. And I think it's wise, it's very wise. Just like we're learning about personal finance and DIY investing so that we don't have to pay somebody 1% assets under management fee every single year to do something that we now feel confident that we can do on our own. Maybe the same is True, especially early on, that a little bit of knowledge garnering some wisdom in this space can avoid us having to pay a fee that can be pretty significant to somebody else. And then when we do feel like that's the best place for us to go to hire a professional to be in our corner on the tax front, well, now we know what questions to ask them and we know how to hold them accountable. And we know how to look at our own tax return and tax information and say, well, wait a second. You know what Hannah alluded to early on in the conversation? My tax pro missed this massive deduction. And I knew that because I, she, she brought enough to the table in that conversation to know this tax professional is not right for me. And they're missing out on some really important things. And if you don't know those things, you, you're assuming your tax pro is doing everything properly, is taking advantage of all the deductions that you are eligible for. But you don't actually know that, right, until you actually know something about taxes yourself. So I, I do recommend her book, Taxes for Humans. I think it's a great one. And I think Hannah has just such a great perspective on taxes and the empowerment in that space because we could all use a little bit of it. All right, that's going to do it for this episode. If you want links to Hannah's site and where you can buy her new book, you can find that up on the website@howtomoney.com until next time, best friend out. We're teaming up in Daffy's Voices for Good Charity Challenge, competing with other podcasters to see who can raise the most for charity. I've chosen Fire, Undue Medical Debt and the Hope Effect to defend free speech, eliminate medical bills and care for orphans.
- [64:20]
Sponsor/Announcer
And I am taking the effective altruism route by supporting GiveWell's top global health charities that save lives for just a few bucks. Donate@daffy.org voicesforgood by December 2nd to back these charities and for a chance to win a trip to the 2026 iHeartRadio Music Festival in Vegas. That's Daffy.org voicesforgood hey, I'm Kyle McLaughlin.
- [64:43]
Kyle McLaughlin
You might know me as that guy from Twin Peaks, Sex and the City, or just the Internet stand. I have a new podcast called what Are We Even Doing?
- [64:52]
Joel
We're off.
- [64:53]
Kyle McLaughlin
I embark on a noble quest to understand the brilliant chaos of youth culture. Each week I invite someone fascinating to join me to talk about navigating this high speed rollercoaster we call reality. Join me and my delightful guests every Thursday and let's get weird together in a good way. Listen to what are we even doing on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
- [65:20]
Nora Jones
Hey, I'm Nora Jones and I love playing music with people so much that my podcast called Playing along is Back. I sit down with musicians from all musical styles to play songs together in an intimate setting. Over the past two seasons, I've had special guests like Dave Grohl, LeVay, Rufus Wainwright, Mavis Staples. Really too many to name, and there's still so much more to come. In this new season, Lizzie and Nora Jones is playing along on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
- [65:49]
Hannah Cole
This is an iHeart podcast.