Welcome back to Don’t Retire… Graduate! For our season six finale, I was thrilled to talk taxes in a way you’ve probably never heard before. Today’s episode features a conversation with Hannah Cole, tax expert, author, founder of Sunlight Tax, and a practicing artist who is on a mission to demystify tax planning for creatives, freelancers, and small business owners. Not only does Hannah Cole bring a wealth of knowledge from both the art and tax worlds, but she also brings a bit of humor and a whole lot of practicality—just check out her new book, "Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self Employed," and her PG-rated "Tax Dominatrix" character!
In this episode, Hannah Cole and I dig into why tax education is so hard to find for creatives and what inspired her to blend a career as a professional artist with expert tax advice. We talk about her journey—staying an artist while becoming a tax pro—and why that dual perspective matters for artists, freelancers, and anyone trying to turn a side hustle into a sustainable business.
We get into the weeds on the distinctions between LLCs, S Corps, and sole proprietorships, but with an approach that isn’t just technically sound—it’s grounded and totally accessible. Hannah Cole breaks down concepts like her "Power Triangle" (tax-smart saving, tax planning, and investing), discusses the difference between tax planning and tax filing, and explores the shades of gray between tax avoidance, evasion, and truly strategic tax moves.
We also don’t shy away from big issues: the structure and complexity of the U.S. tax code, how to find a good and ethical tax pro, the realities of audits and IRS letters (why they’re scary for everyone!), and why a fairer and simpler system could benefit us all. We even debate the merits of estate taxes, VAT taxes, and the potential for a flat tax—always with respect, openness, and a sense that, with a little creativity, we could do more to make the tax system equitable and human friendly.
Whether you’re an artist with a side hustle, a small business owner, or just allergic to the idea of tax planning, this episode will leave you feeling empowered and maybe just a little bit more optimistic about taxes.
5 Key Takeaways:
Creatives Need Tailored Tax Help:Hannah Cole identified a huge gap for artists and freelancers, who are often stereotyped as being "bad at money," and built resources to help them thrive, including her book and visual guides.
Tax Planning, Not Just Tax Paying:Tax planning is about making the system work for you—not just paying what you owe. It’s about grabbing “the coins in the couch cushions” and using the tax code’s incentives to your advantage, which is very different from the pain of cutting a check.
Choosing the Right Tax Pro Matters:Not all CPAs are created equal. Hannah recommends prioritizing respect in your tax adviser relationships and being wary of anyone who’s aggressive to the point of danger. A good adviser makes you part of the decision-making process.
Myths About the IRS and Enforcement:The societal fear of the IRS is often fueled by those who benefit from weakened tax enforcement. Hannah contends that, in practice, IRS agents are often kinder and easier to deal with than their reputations suggest—and that real “tax terror” often serves the interests of high-net-worth rule breakers.
Calls for a Fairer, Simpler System:We debate estate taxes, sales tax, VAT, and even the promise of a flat tax. Regardless of where you stand politically, we agree: a fair, equitable tax code—one that doesn’t require an army of CPAs and endless stress—would benefit everyone.
Join us for this engaging and lively conversation that will leave you rethinking what taxes can mean for your life and work. As we wrap up season six, don't forget to subscribe so you won’t miss our season seven premiere in January 2026. Share this episode with anyone dreading tax season—or dreaming of their next creative endeavor—and remember: don’t retire… graduate!
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Transcripts
Eric Brotman [:
Welcome to Don't Retire Graduate, the podcast that asks you what you want to be when you grow up so you can graduate into retirement with purpose and with passion. I'm your host and valedictorian, Eric Brotman and this is our season six finale. Our all new season starts in January 2026. We have some terrific guests lined up, so please subscribe and never miss an episode. Today I'm pleased to be joined by Hannah Cole. Hannah's a tax expert and the founder of Sunlight Tax, specializing in helping creative individuals manage their taxes effectively. She offers resources including her new book, taxes for Humans. Simplify your taxes and change the world when you're self employed.
Eric Brotman [:
And a podcast that provides guidance on tax deductions and financial management for creatives. Her approach is designed to empower self employed artists and freelancers by simplifying tax concepts and providing practical advice tax tailored to their unique needs. Hannah. Welcome to Don't Retire Graduate.
Hannah Cole [:
Eric, thank you so much for having me. It's great to be here.
Eric Brotman [:
So first I, I have absolutely no shame in saying that you have more copies of this than I do, but I do have one and I did read it and, and, and I want to talk about it today because I know it's hot off the presses and so I congratulate you on a, a major undertaking. Writing a book is no small feat. What, what possessed you? I guess before we even get to the book, what possessed you to leave an art career and go into a tax career? Because I think that is using two different sides of your brain very significantly.
Hannah Cole [:
Sure. Well, I never left art. I'm still an artist. I have a gallery.
Eric Brotman [:
Okay, so you're doing both.
Hannah Cole [:
Yeah, I do both. I was attracted to taxes because it's seasonal. So actually part of what I, well, what I started doing, the, you know, life evolves was I do, you know, I run a tax season and then I shut the door and I go to the studio.
Eric Brotman [:
Okay.
Hannah Cole [:
Yeah, so I kind of am in one mode or the other. But what, what kind of inspired it is? Just that as a professional artist, I found it very difficult to get good information about just, you know, running a small business, doing the tax side, bookkeeping, paying quarterly taxes, those things you need to do when you're self employed. I think people in STEM fields and business school, they get great resources and access to information like that, but there's a lot of stereotyping of creative people as though we're bad at this. And we often are very under resourced in these kind of skills and this kind of education. And there was a real cultural disconnect when I tried to talk to accountants because they really did not get kind of what an artist, what a professional artist looks like does what a valid deduction might look like for me. And so I decided to go back to school and actually train in it so that I could bring this information to the creative community.
Eric Brotman [:
Well, I love that you still have one. One foot in each pool, you know, because that, that allows you to be very relatable to certainly the audience you're. You're speaking to. I found some things in the book that were. Were fantastic. I really enjoyed the way you broke down whether or not you needed, for example, an LLC or an S corporation or whether you wanted to get. And there was some technical information here, but all of it, I thought, was presented in a way that was really accessible. And so I give you, I give you a lot of credit.
Eric Brotman [:
Writing a book about taxes is how many people pick up a book about taxes and go, I gotta read this. And yet you've made this so relatable that I think it, I think people will pick this book up and will learn from it. And not just creatives, freelancers, but, but also any small business owner, anyone who's thinking about, you know, leaving their hobby. And you do a great job of explaining the difference between a hobby and a, and a. And a starting business and so forth. So there's some really good stuff here. I, I need to first ask where you came up with the concept. And this is a PG show, by the way, of the Tax Dominatrix.
Eric Brotman [:
Because, you know, when I, when I first read that, I did a double take and then I saw the graphic. There is a dominatrix next to the 1040 here, I think. Where did you come up with that? Did somebody give you that nickname or did you just make that up on the, on the spot?
Hannah Cole [:
No, that's mine. That's because, I mean, for the listeners out there, it's a pretty PG Dominatrix.
Eric Brotman [:
Oh, very much so, yes, Very much.
Hannah Cole [:
Yeah, she's cartoonish. But I, the reason that she's there is because, well, one, I really care about it being a very readable, you know, book with a sense of humor. And I was thinking, you know, in taxes there is this hard edge. Like, there are deadlines, there are punishment, there are penalties. How are we going to deliver that sort of tougher information? And I was like, well, what's the most fun possible way to deliver that? Let's do a dominatrix. But in my, in my Business. I, I actually talk about how, like, you know, I'm, I'm sunlight 95% of the time. Right.
Hannah Cole [:
Like, you can do this. You got this. Let's go. Let's take advantage of what we, you know, the tax code in every way that you can. But then I'm 5% dominatrix. Because at the end of the day, all right, now's the done. Like, you got to get this done.
Eric Brotman [:
That's, you know, first of all, it was the first thing that I, that I grabbed onto and said, oh, I'm going to enjoy this because, you know, that is already creative and I'd never heard anything like it. Clearly there's a little Jekyll and Hyde going on in your, in your, for you to be 5% in that camp. But I really thought you did a terrific job. And you described something in the book called the power triangle, which I thought was also very helpful and helped to set up the reasons behind some of the whys you need to tackle these things. And you talk about the trio of tax smart saving, tax planning and investing. Can you talk a little bit about where that came up, where you came up with that and maybe what would have joined the rectangle or octagon or rhombus had you added some extra things to it?
Hannah Cole [:
Well, I wanted to keep it simple, so I would go for as few elements as possible. This is your world. I mean, I sort of hand it the book kind of hands off to you at that point. But I'm speaking really to a lot of people who feel a little allergic to money and feel a little scared of it. And so just a lot of times people in sort of care based fields, creative fields, are, are really not even thinking that retirement is for them. I know you don't like that word retirement, but like, it's like, I do like the word.
Eric Brotman [:
I just don't like what it. The way it's defined a lot of places. But yeah, I know. I think retirement's a great thing.
Hannah Cole [:
Yeah, no, you have, you have a beautiful rebrand of it. I think it's really awesome. So it's sort of like I just wanted to kind of package those concepts in a way that feels appealing and that kind of, I think a lot of the words, you know, tax planning, like from my business, I can tell you that my tax planning workshops are the least popular workshops I run. I am here like, hey, this is where you get the good stuff. This is where you get capture all the tax credits you could and like make sure getting every deduction this, this is what you, you know, should want. But it's funny because I think a lot of people feel like, oh, that's like, tax stuff, and it's optional. Forget it. Right.
Hannah Cole [:
It's almost like I don't want to deal with taxes any more than I absolutely have to, so I'm not going to do that stuff. So just to me, I've had an awareness that there is a group of people out there who are really averse to getting into even this, even stepping in the doorway, Erica, of the world that you operate. And so I'm just trying to make it feel a little bit more like tax planning is like finding all the coins in the couch cushions. It's not like working harder. It's just getting the money you already have to work harder for you.
Eric Brotman [:
So I think people confuse tax planning with tax filing or tax reporting or tax paying. Tax planning is a process that really is kind of like finding the bag of money. Yeah, tax paying is painful. It's writing a check for something you don't necessarily want to write a check for. Necessarily. Or you certainly don't control exactly where it goes. And then, of course, when you start talking about taxes, some of them are easy to avoid legally or reduce legally, and others are not. And there's a big difference between tax avoidance and tax evasion.
Eric Brotman [:
I mean, you talk a little bit about. Well, right. And you talk about the criminal element trying to evade taxation, which, which, you know, I would never defend. And I think it's, you know, punishing those who break the law is one thing. I do think the laws are so convoluted that. And they're so bastardized that, you know, I think the tax code, the US Tax code, I believe, is the longest book ever written.
Hannah Cole [:
I'm not surprised by that. I mean, there's a design. There's a design issue here that, you know, good design means editing. And it's just the problem with the tax code is it's additive. We just add more to it. Add more to it. Nobody goes back and edits it out again. And I.
Hannah Cole [:
We're maybe way over, like a hundred years overdue for that, at least.
Eric Brotman [:
And can you imagine how horrible that project would be?
Hannah Cole [:
Oh, it would end thankless. It would be thankless.
Eric Brotman [:
Think about the folks who edited your manuscript, you know, having written books. I know people and, and, and you, you labor over every word, every sentence, all the design, all the things. And, you know, at the end, you just sort of say, all right, it's, it's, it's Never perfect. It's good. It's done. Yeah. The tax code to go through that would be a special kind of torture. And I'm sure there are people out there go, I want the gig.
Eric Brotman [:
I would tackle this. But it. It doesn't. It's not a romance novel. It is a horrible read. And it's section this and code that and section this and the.
Hannah Cole [:
The.
Eric Brotman [:
I think it's one of those things where there are more end notes than actual content because there's an exception to every single rule. And there's the. There's so many different ways to game this. And so, Hannah, I'll ask you, because we've had lots of CPAs on the show and, and I don't love necessarily talking about taxes. I do love talking about tax planning. Yeah, we've had a lot of CPAs on the show, and what I've said to them, and I'll ask you the same thing, is if I were to handle my stack of stuff for April 15th, you know, it's. It's March 1st. I've gathered all the things, and you do a nice job with the checklist and the things to gather, but I've gathered all of it and I go here, Mr.
Eric Brotman [:
Or Ms. CPA, will you please handle this for me? If I gave it to 10 different CPAs, I believe I would get 10 different tax returns.
Hannah Cole [:
I think you're right.
Eric Brotman [:
That speaks to what. What I think is a problem where this is, and I dare say it to you, it's more art than science. And since you do both, maybe you're the absolute best person to talk to. I think if you're going to get 10 different tax returns and they're all legally acceptable, then the nuance level to that is just terrifying. Like, how do you know as a taxpayer whether you got the best tax advice or lousy tax advice? How do you know if you put everything you needed to into the system? You know, the turbo taxes of the world, or whether you should be using an H and R block or a Jackson Hewitt or a. Or a, you know, somebody just to file your taxes, or whether you need a CPA or a team of CPAs or there's such a spectrum of advice. How do you know that the advice you're getting is good if somebody else just as credentialed would give you a totally different answer?
Hannah Cole [:
I think this is a really tricky problem that you're pointing to. I think. Oh, oh. It's very opaque. It's very black box to most taxpayers. And I mean, unless you really have an understanding of taxes yourself, which I do think is a problem I am attempting to solve with this book is giving a lot of that, like why behind the tax decisions to people. But I think, you know, especially just the way that the tax industry works like you are, it's a volume industry. You're going to, you know, somebody who's doing taxes is just almost like filter feeding, just bring, just saying yes to every client and doing them as fast as humanly possible, putting everybody on extension at a certain point and just going through and trying to extend their season a couple months after that.
Hannah Cole [:
And that is not a position a person well positioned to talk to you with thoroughness about, like what decisions they may have made within your tax return. As a tax practitioner myself, I always try to. When there's a decision, you know, anything that's sort of like black and white, fine. But places where there's a decision to be made, I always want to bring the client in on all of those. So I will keep like a list of sort of like decision points for discussion. Not everybody does that. And if you're not charging enough as a tax person, you don't take any time to do things like that. And so those clients just never know.
Eric Brotman [:
So you mentioned sort of the fee structure, and one of the challenges there is that that creates the structure of who can actually afford decent tax advice and maybe who can't, which you talk about in the book pretty significantly as well, saying, well, if the people who have a huge team of CPAs and can spend a fortune to save a fortune are very different than, you know, the average couple or the average individual business owner or family or whatever, you know, most folks don't have that, that luxury or ability or frankly aren't sure that they'll get enough juice out of the squeeze. Like if you pay, if you pay an accountant four times what you're paying your current accountant, are you going to save four times or more in taxes? Maybe not. I mean, it's not quid pro quo. Right? You're not. So, so where is that, where is that decision made on how much, how much advice do I need? How much planning do I need? What should this cost me? I mean, when we, we're not CPAs, we don't do taxes, we do financial planning and wealth management and we refer out tax business to people. And it's getting harder and harder to find CPAs who even want to do taxes because the, the profit margins are so slim and because you can't get young people to join the field because none of them want to spend a hundred hours and, and eat all their meals at their desk for three months every year. I mean, people don't want the job anymore. So, yeah, you know, what do you do in an industry that is reinventing itself? I mean, it's got, you've got the robo pressures.
Eric Brotman [:
So the, the turbo tax didn't put CPAs out of business, but it may have put some lousy ones out of business, which isn't a bad thing. The good ones didn't go out of business. Right. How do you, how do you find. How do I, as a financial advisor, how do I find competent tax advice in the price range that's appropriate for a given family? How do we navigate that?
Hannah Cole [:
I mean, I don't have an answer. I think it's very difficult. I literally wrote a book to try and help people do taxes on their own. And I have a triage section inside the book that triages. Here's where you can do it yourself. Here's where you shouldn't do it yourself. These are the scenarios where you do want some professional help. So at least we can sort out who actually really should be paying versus who can DIY it.
Hannah Cole [:
I mean, I personally, when I am recommending, you know, the way that I want someone to approach a tax professional, I say, you know, if you, if you're not feeling respect in the room, I wouldn't try at all. I would leave. Because to me, you know, I have, I have been on the receiving end of a sort of a disrespectful accounting experience. It's why I formed my company. And so to me, that's primary because you're not going to be able to ask the questions you want to. Taxes are actually really vulnerable. You're talking about your income, your financial decisions, how much society values you with pay. So it's like, it's a tender thing.
Hannah Cole [:
So to me, the respect is really primary. And then beyond that, I think there are some red flags to look out for. I think some people. The problem is that some people, what they want is a tax person, or what they think they want is a tax person who's super aggressive. They want somebody who's just like, yeah, we can deduct that. Yeah, we can deduct that, bring it all. We can make that a deduction and just like. But the problem is, you might not know as a taxpayer, if you work with someone who's being too aggressive, that person might be kind of skirting the line in a way that's Dangerous to you, and you might be more in the crosshairs for an audit.
Hannah Cole [:
And so ultimately, you'll be miserable that you chose that person when you get that letter from the irs. So there is a bit. I. I actually think it's a place where conservatism is quite positive, and you. You want somebody who's like, that one's not really. That's not a business deduction. You know, we're not going to push that. I actually think that's better because that's somebody who's, like, not taking chances with your tax return.
Eric Brotman [:
So. So years ago, I was a victim, like, so many, of identity theft, and.
Hannah Cole [:
Oh, no.
Eric Brotman [:
And. And now have to get a PIN to do my taxes, which, actually, I think we should all get anyway. I think that just makes sense. But I get a letter every year from the IRS with my pin, and just the letter with the PIN scares me to death because I see the envelope from the irs. Like, I know that's not a. That's not a Christmas card, Hannah. That is a different thing. And I see it.
Eric Brotman [:
I'm like, oh, my pin. Fine, because. Good. But it. It. Your blood pressure goes up exponentially when you see IRS on an envelope coming your way.
Hannah Cole [:
It happens to me, too.
Eric Brotman [:
Terrifying.
Hannah Cole [:
It's terrifying. I get my. I'm an enrolled agent, so my license is from the irs, and I get correspondence with them all the time. Like, had to renew your enrollment. I freak out, too, when I see that logo in the mailbox.
Eric Brotman [:
Okay, well, isn't that a sign of an issue that we should try to resolve, that if the IRS really is that much of a troll under the bridge, that there's got to be a different way to approach that. Like, we're all. Everyone's terrified of it. Like, it's like they're coming to get us in some way. Even if you've done nothing wrong, The. The idea of. Of an audit, and you talk about what to do if you're there and how to get counsel and all those things, but it's a terrifying thing. Is there a better way than our current system in your mind?
Hannah Cole [:
Well, I actually think that sowing terror of the IRS is a strategy being used. And so it's. It's kind of deliberate getting placed there if you're. Honestly. I mean, I deal with the IRS quite a bit. They're so kind. They're generally so easy to work with, especially if you compare them with the state offices. And that makes sense.
Hannah Cole [:
You know, states often have balanced budget amendments and cannot work on a Deficit, whereas the federal government can. There's something that makes you more forgiving when you are the body that can print money. So states are a lot more aggressive and a lot more difficult to negotiate with. The IRS generally is, like, pretty easy, to be honest. I find that they don't really deserve the reputation that they have.
Eric Brotman [:
But yet when you see the mail from them, you still have that visceral reaction, even though you don't.
Hannah Cole [:
Because I live in the society, too. Yeah, I know.
Eric Brotman [:
Okay, but if, you know, if you know that the, the wizard behind the curtain isn't terrible, then why does it still create that, that visceral reaction for you? If, if you, I mean, how, how did they become so vilified that they're terrifying if you know different and it's still creates that for you? Isn't that a sign of something? Isn't that. That's not just societal? You, you of all people should know better. You're the enrolled agent. You work with them all the time, and yet it's still like, oh, well.
Hannah Cole [:
I mean, I'm not going to. Enrolled agent or not, I'm not going to tell you that, you know, going through an audit is my idea of a fun weekend. I mean, it is the check and balance in our system, and I recognize that, the fairness within that and that, you know, if every single year I'm not audited, the IRS is trusting me on every deduction I put in my tax return. Of course, they should have the right to look once every 10 years and be like, all right, let's just check and see that you're not making this up. Right. I actually think that's legitimate. Do I want to go back and, like, pull out all the receipts? Like, I have a pretty good system and I'm not scared of it, and I can do it. But is it my idea of fun? No, that's fair.
Eric Brotman [:
Well, so. So you write in the book, among other things, that if you owe money to the government, pay your state first. And you just, you just talked about how the state can be a little less forgiving and some of the reasons why. And I thought that was, it was interesting because I, I think getting a letter from the comptroller of your state seems somehow less terrifying than getting a letter from the irs, despite the fact that that wizard behind the curtain might actually be a, a tougher out. But it doesn't, it doesn't have the same. It doesn't have the same weight, the same gravitas. How did, how did they manage to, to be the Bad guy, so to speak, and still paint themselves as better than the irs. What kind of marketing team do they have that's like Public Relations 101?
Hannah Cole [:
No, I think it's the PR against the IRS. I think honestly, if you are somebody who's super, super wealthy and you want to cheat on your taxes or just not pay your bill, which we have a 7, a 6, $600 billion tax gap in this country from wealthy people who simply do not pay the tax bill that they owe. And the IRS doesn't have the enforcement to go after them. And the reason is that they, you know, there's, they pay for these lobbying groups to go to paint the IRS as this evil institution that everyone should fear. Where it's really pretty helpful to fund the IRS from my standpoint because it means when I call them, because I need help with my pin, they pick up the phone, right? Like I want a well funded IRS and I frankly want a well funded IRS to go and collect that $600 billion that, you know, the top, you know, 0.01% are not paying just because they can afford to not pay. The IRS doesn't have the enforce. It costs a lot of money to collect the taxes from a tax cheat who has an army of tax accountants and lawyers. So that's the reason why that campaign against the IRS exists.
Hannah Cole [:
It's not really for your benefit or mine or any of your clients. It's for the benefit of people cheating on their taxes in the top of the top 1%.
Eric Brotman [:
So there was some stuff in the book that, that caused me some pause and, and I, I want to be, I want to bring this to light and see what your, what your thoughts are, but particularly the estate tax, because I am an accredited estate planner and I do possible to help families find ways to avoid that tax because it does feel like confiscation from the dead. And it does impact families. It impacts folks who own farms, it impacts folks who own businesses. It impacts folks at various levels. Now you, you state that there are only 1500 estates in the US that would be impacted by it. And the federal estate tax limit right now is especially high. So you're absolutely right right now where that limit is. Now I remember when the limit was only $600,000.
Eric Brotman [:
Yeah, I remember when it was $600,000. Now it works out to be like 28 million, which most families don't ever have to think about. But at the state level, state and, and you know, we talk about the state versus the federal. @ the state level, estate taxes are very real and are hitting a lot more families. And it's causing migration, it's causing migration of families, of means from one state to another. You know, you're in a very favorable state from that standpoint in North Carolina. I'm in a very hideous state in that standpoint in Maryland. And so we spend a lot of time thinking about what are the ways to avoid this.
Eric Brotman [:
We do webinars and education around estate taxes. And what we're really talking about is the state, not the.
Hannah Cole [:
Federal. Yeah, that makes a lot of.
Eric Brotman [:
Sense. So, so I think when we talk about death taxes and I, you know, you, you made it sound like death taxes was something made up because, because of, of, of an evil group of people trying to paint it a certain way. And, and what I would say is it kind of is a death tax. It's paying taxes beyond the grave for passing assets on. What is the, what is the, what is the solution? I'm going to put you on the spot. What is the solution to the desire to not allow wealth necessarily to, to, to continue to grow exponentially and infinitely? And why, first of all, why is that a bad thing? But second of all, where, what is the solution around that? At, at the, at the federal level, is there a better way to do it than to force an estate to liquidate certain things, particularly when they're illiquid? And that's.
Hannah Cole [:
Challenging. Yeah, well, first of all, I really am only addressing the federal estate tax. And I, I don't really have an argument with you about this. States I, and I, I don't, I know that they vary tremendously. You know, Massachusetts, New York, Maryland are kind of a different story from Florida and Texas. But. Yeah, so I'm, I'm not really, you know. Okay, those thresholds you may find very unfair and they may legitimately be unfair.
Hannah Cole [:
I mean, that, that's a conversation. I'm, I don't address it at all in my book. I'm, I'm talking about the federal threshold, which is really.
Eric Brotman [:
High. It's really high right now. It's really high. Although it's low hanging fruit for one administration versus the other. I mean, that's one of the, that's one of the limits that gets changed the most because it impacts the smallest number of people. So it's really easy to create popularity around it. You know, getting 99% of the population to say, yes, let's tax that 1% more is not a hard vote to get. It's also not really what happens because the, the, the wealthiest people have ways to avoid this legally because of the enormous tax code that we have.
Eric Brotman [:
So.
Hannah Cole [:
If.
Eric Brotman [:
Yeah. If we want people, if we want people to be paying more for whatever reason, shouldn't we simply change the tax code to make it so that there's less gamesmanship and more fairness in the.
Hannah Cole [:
Code? Oh, absolutely.
Eric Brotman [:
Yeah. All right, good. Then we agree on that. We agree on.
Hannah Cole [:
That. I'm all for fairness. That's all I want in this world. Yeah. Fairness.
Eric Brotman [:
Absolutely. So. So I'm going to throw something else at you. And I'm having fun with this, Anna. And you're. I enjoyed your book. I enjoyed getting to know you. I love the fact that you're both the artist and the tax person, that you're using both sides of your brain.
Eric Brotman [:
I want to throw something out at you for your opinion as a tax expert. All right. I'm going to put you on the spot because it's my show and I get to do that. Government sometimes uses taxation as a way to curb behavior. Behavior. Right. So a cigarette tax, an alcohol tax, a gas tax, things that are taxed in the hopes that people will conserve or use less of or stop using or not do anymore. So why are we taxing income? Why in the world would we.
Eric Brotman [:
Would we have a system where disincents people to go earn more, where there's a point, a tipping point, where it doesn't make sense to work anymore as opposed to finding a way to do consumption because the wealthiest families are going to consume arguably the most. You know, the VAT tax to me is far less offensive than the income tax because it penalizes something we think is a good thing. At least I think is a good thing, which is go be more successful and earn more.
Hannah Cole [:
Money. Yeah. You know, I agree that we should have a VAT tax, that VAT taxes can be far. Can be very fair. I've spoken and I interview in the book William G. Gale from the Brookings Institution, the Tax Policy center. And he has some really great writing which I would be happy to link to in the show notes if you want. But about how.
Hannah Cole [:
Yeah, the. The sort of basic fairness behind a VAT tax and what a really good structure for one is. I'm not sure I can tell you every detail of that here. But yes, basing it on consumption, I mean, the problem is like we have some sales tax. Sales tax tends to hit lower income people much harder and be a regressive tax. A regressive tax. Just for your listeners who don't quite clock what that means, it means a Tax that hits people with the least money the hardest and is the least burdensome for people with the most money. Poorer, lower income people spend most dollars that they bring in.
Hannah Cole [:
And so for that reason, sales tax is considered regressive because almost all their money is subject to sales tax in that way. Some states have exception, Massachusetts has exceptions for groceries and necessary clothing, you know, non luxury clothing and things like that. So that's, I think those are, there are ways to make it more fair. But you know, the, the very wealthy, a lot of their money they don't spend, they, they bring it to someone like you and they invest it wisely and they watch it grow and they're trying to not spend it, which of course is positive. We want that. But so a lot, a far less proportion of their income is getting taxed because they're not consuming with as many of their.
Eric Brotman [:
Dollars. So some of this is framing too. I mean you talk about the framing of the death tax or tax reform and you politicize it a little bit, but you certainly go to a point to say this is what those words are designed to mean. I remember in, in Maryland here when then Governor Martin o' Malley decided that, that he was going to propose an increase to the sales tax and it went from 5% to 6% and he said, well, it's only a 1% increase. One could argue it's also a 20% increase on the actual amount of tax being.
Hannah Cole [:
Paid. So if, I mean if we're in the world of investing, we know seemingly small percentages can have a huge.
Eric Brotman [:
Impact. Huge, huge. So, so when I, when I look at that, I think, but again, it's the messaging because the country is so split politically and I don't have to tell you that, we all know that. But half the people were saying this is a 20 increase and the other half were saying it's only 1%. And they were both right. Mathematically, they were both right. But it's all the messaging you hear and whether you think this is a great thing or a lousy thing. So I throw one more thing at you from a tax perspective.
Eric Brotman [:
I, I saw a proposal years ago that I thought was the best proposal I had ever seen from a tax standpoint. And it, and I'm not going to tell you who, who made the proposal because it might change the way you feel about it, but it was related to a flat tax and it was related to a tax that would have a, a threshold under which no tax was paid. And this was an income tax. There were threshold where where no tax was paid and it was the same. So people who paid no income taxes now would still pay no income tax, but there would be a flat tax on every other dollar, and there would no longer be deductions, exemptions, credits, or anything else. It would just. It would just solve the problem and largely eliminate the need for all of the filing and all of the time and all the paperwork. And of course, CPAs hate it because we wouldn't need CPAs the same way for audits.
Eric Brotman [:
We would. But if a flat tax were able to be implemented such that it was. It was done on income automatically and there was no gamesmanship, would you consider that potentially fair if it still excluded the 50% who aren't paying income taxes now, arguably by having a 50 or $60,000 exemption per.
Hannah Cole [:
Household? I love the idea of simplifying the tax code. I think that's a positive thing for everybody. I'm also interested in fairness. I don't care who proposed it, as long as it's fair and equitable. Great. I will consider anything. I think I'd want to look at the details and see where the impact would land, because to me, that's what would make it fair. And I don't have that data here with this scenario.
Hannah Cole [:
You know, a lot of times the stuff that feels complicated is actually to create equity. And so complicated doesn't always mean negative. Although, of course, you know, something that I think would be great would be that we all don't have to file a tax return. There are other countries that do it that way. You know, in.
Eric Brotman [:
Spain. Yes, that would be.
Hannah Cole [:
Lovely. You just got a letter that says, like, here we already have your basically Spanish equivalent of your W2. You know, we've already got the taxes, like, you're done. And small businesses, the people that I serve, would still have to file a piece of a tax return to adjust for what their business deductions were. There's no way for the government to have any insight into what you spent running your podcast. It's hard to get around that one, but it would, you know, and honestly, that was killed by lobbying from the tax industry that is possible. We could do that in the US And I actually think that would be wonderful. I would support.
Eric Brotman [:
That. Then I'm delighted. We've crossed a lot of bridges today, and you and I can run for office together. No, we can't. I'm not electable, but we could definitely talk taxes anytime. Where can folks learn more about you? Where can they get a copy of this book, which I do Think particularly for business owners or for people who are trying, the DIY is a really valuable.
Hannah Cole [:
Resource. Thank you so much. And then go get Eric's book because it helps you. Once you've learned that the power triangle is actually there to help you and not scary, then go, go get help doing it, implementing it. People can find me@sunlighttax.com all the links that you would want. There's a link to my book Taxes for humans there. @sunlighttax.com there's also a free visual guide to tax deductions. So if you are running a side hustle or have a small business or self employed, I have these.
Hannah Cole [:
This is where being an artist is very helpful. It's a beautiful, beautifully designed visual guide to tax deductions that you can get.
Eric Brotman [:
There. Very good. And before I let you leave the show, particularly being the finale, no pressure at all, but you are the last person in 2025 to tell us what you want to be when you grow up. And so that's a big deal. What do you want to be when you grow.
Hannah Cole [:
Up? Oh, I want to be so many things. I don't want to have to.
Eric Brotman [:
Choose. Spoken like a true artist.
Hannah Cole [:
Okay. Well, I do want to be an artist when I grow up. I still do.
Eric Brotman [:
Yeah. Anything. Any. Okay. We've had some great answers. We've had some people who said they wanted to be Tinkerbell, they wanted to be Superman. We've had some off the, like, crazy kind of answers. If you're doing the things you love, to me, you're already retired.
Eric Brotman [:
You know, I mean, if you're doing what you love, particularly if you're financially independent, I think the goal for any family is reach financial independence and then do what you love and as much of it as possible, make a positive difference, and everybody wins. I enjoyed this, Hannah, because I thought that we might have more disparity in our outlooks. And yet we've. We've. That hasn't been the case. We've actually come up with a lot of ideas together and maybe somebody somewhere on Capitol Hill is listening. These are good.
Hannah Cole [:
Ideas. Yeah. And if I can add to that, I actually don't think we all need to feel so far apart. I'm interested in a fair tax code, and I'm 100% sure that you are.
Eric Brotman [:
Too. Yeah. Fair tax at the end of the day.
Hannah Cole [:
Yes. Good ideas come from both sides of the aisles, and good people can disagree. And I think these are debates about what we value in society that are valid debates, and we should have them. So I think, well, we do talk about it.
Eric Brotman [:
Anytime. Well, we just did and there were no casualties and neither of us was struck by lightning. So I guess we're in really, really good shape from that standpoint. Thank you for being on the show. Good luck with the book. Good luck with. I would love to see some of your art someday. Actually, I haven't checked that out, but I loved the book and I appreciate you being on the show and this is a great way to finish our season.
Eric Brotman [:
So thanks. Hannah. Thanks for being.
Hannah Cole [:
Here. Thank you, Eric, so much. Thanks for having me. Great to be.
Eric Brotman [:
Here. I'd like to thank everyone for listening and watching today and all season long. If you enjoy our show, please share it with friends and family so they can join you on your journey to financial freedom. Our Season 7 premiere will be live on January 1, 2026 with amazing author Jeremy Kyle. For now, this is your your host, Eric Brotman wishing you a happy, healthy new year and reminding you don't retire. Graduate securities offered through Kestra Investment Services, llc. Kestra is member finra SIPC Investment Advisory Services offered through Kestra Advisory Services, llc. Kestra as an affiliate of Kestra is Kestra is or Kestra as are not affiliated with Brotman Financial or any other entity.
