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our listeners are getting a free shimmer face oil with their first purchase when you use co tea at checkout so all you have to do is go to jones road beauty dot com and use code financial tea and then after your purchase they're going to ask you where you heard about them please support the damn show and tell them financial t sent you stay rich we are all family here okay me and you we have the same uncle uncle sam and unfortunately he wants a cut of everything what's up rich people it's me haley aka misses dow jones and this is financial tea what's up sippers it's me haley aka misses dow jones and this is financial tea the podcast where i teach you how to build wealth even during tax season yes we are going to talk about taxes today before you panic and turn this off please relax and here's the thing about understanding the rules and this is why i wrote my book the new rules of building wealth because you need to know the rules if you want to game the system and if you don't then you're just going to get yourself into serious trouble in case in point swiss beats otherwise known as mister alicia keys yes new york state of mind's husband is in trouble with our uncle sam like he is a legendary producer he is a multi multimillionaire like if you want to feel poor just google their house in la it's insane but he is also someone who has had the irs on his back multiple times and i'm just like swiss like get an accountant who knows how to do this or figure it out yourself like at one point the irs filed tax liens saying he owed millions in unpaid taxes and recently they even did this and by the way this happens to celebrities and rich people constantly because making money and managing money are two completely different skill sets so you will see athletes musicians actors mike tysons people who are wildly successful they even have tigers i'm looking at you mike tyson have chaotic finances and have ruptured relationships with the irs because two things in life are always coming for us taxes and death so we need to lock in and at least prepare for one of them that's what we're going to do today because the irs doesn't care how talented you are they don't care if you're swiss beats and you produce half of hip hop they just care if you paid them and trust me if you haven't they're going to find you and they are going to make you pay fines so today is the crash course in taxes that you were never given it's not going to be boring it's just going to help you really game the system i'm going to teach you how taxes actually work which no one ever talks about but it's important because they do end up coming around say with me every single year so today we're going to do a crash course in taxes it's not going to be boring because we're going to be together and i'm going to show you how people legally lower their bills because yes there are legal ways to bring it down i'm going to explain to you how taxes actually work we're going to talk about how billionaires pay no taxes and the mistakes that are super common that get you in trouble with the irs because here's the thing the difference between someone who feels constantly screwed by taxes and someone who just like pays them every year and moves the fuck on with their life is just understanding the rules and you know i'm all about the rules my book future rich person is the new rules to building wealth i love a rule so i'm gonna give you all of them i'm gonna give you all my secrets and all that you need to give me is a like and a subscribe because that really helps grow the show and honestly a comment like i would die for a comment i read them all i love to hear from my sippers i know that you're watching i know that you're listening so please like get in the chat i want to know what you want to hear about like who did holler i'm i'm here i'm here i want to let's break the fourth wall let's get into these questions producer amber has put them together i've not seen them yet but first let's get into the mdj market report okay sippers welcome back to the market report i've made the bold decision to go handheld if you are watching on youtube that is the vibe today because we have got four stories that you need to know happening on wall street this week and it just felt like the energy that was necessary to really capture them so the first one is the total mess in the oil markets which you know no one can control what's going on politically right now it is so stressful so crazy the strait of hormuz is basically blocked and twenty of the world's oil is basically stuck which is driving up prices but you know it feels like a lot of times political conflict doesn't like affect you at home you can feel so far away from it but with this honey you are feeling it like when you are at that gas tank there is sticker shock you know what is happening overseas because you're feeling it in your wallet and this actually happened to my sister this weekend because she filled up her tank and it was one hundred twenty and it's usually seventy dollars she does take premium gas yes she has an audi secondhand but when oil gets this expensive everything gets more expensive so like your amazon packages your groceries because oil is in fertilizer so farmers can't afford fertilizer like it just the whole everything is inflated so i'm going to give you the advice that i gave her i had some tips for her to save money on transportation that hopefully will help you save money on transportation too the first thing i told her is to download gas buddy which is an app that tells you where to get the cheapest gas near you because like the gas station near the street might be thirty cents cheaper than the one that you usually go to so definitely download gas buddy i also told her to this is random but check her tire pressure because a lot of times if your tires aren't fully inflated that ends up eating your tank way quicker than usual and probably the biggest hack that i haven't heard anyone say was i had that girl freaking compare her car insurance rates because here's the thing i do not know what is happening with the war in iran i don't know when gas prices are going to go down but i do know that she needs to save money on transportation and a really easy way to do that is to look at your fixed expenses and see see what you can bring down like your insurance so i have a really easy tool free that you can use on misses jones dot com that's what i used for olivia and we got her insurance down from three hundred a month to one hundred and fifty dollars a month just by comparing it so do not be complacent this is the time to really be thoughtful about what you're spending on and make sure that you're getting the best rates and i hope that helps and obviously this oil drama is spilling into wall street too i would say the stock market is officially in its correction era and know that it's not the fun taylor swift kind although reputation was a great album but really in wall street lingo correction means the market has dropped ten percent from its recent highs so it's basically the market's way of having a britney breakdown like remember britney with the baseball bat like that is the energy that the stock market is giving right now it's wobbly but i will say that this is actually really normal the market a normal part of a market cycle includes moments where the market corrects and is down so this is very healthy like it's like it's sort of like when you're in a relationship and you fight and you're really scared that you're fighting but then you realize that it's actually like bringing you closer like that sort of this vibe where it's like it's uncomfortable in the moment but it's actually something that like is totally normal and might actually make you better investor in the future if you can just withstand this and see the light through the end of the tunnel so do not panic sell this actually just means that the market is on sale and just honestly like i'm an anxious person like i'm just a jewish girl from that brief side at my core but i will tell you like i'm like teflon when it comes to the market going up and down because i know the data you guys and it shows that over twenty years over you know fifty years the market always goes up so even if we have these moments of red over time you're going to make money and you just have to believe in that i really do because guess what the the numbers don't lie check the scoreboard as jay z would say while the grown up markets are spiraling i do want to talk about a different kind of market to ak the gambling market i feel like i cannot open my phone without hearing about prediction markets so i've become a little obsessed with them trying to learn everything and this week i discovered that platforms like kalshee and polymarket are targeting women yes they have influencer campaigns running on tiktok and x and they've got dedicated accounts like at kalshy girls and at polybatties sort of pushing the platforms with bets on pop culture and celebrity news and lifestyle content and it's like yeah women be shopping but like maybe women also be shopping for bets on the latest housewives cast member and what is scary is that all this marketing is working like women now make up twenty six percent of cash users which is up from thirteen percent just ten months ago and look i'm all for women in male dominated fields except when it comes to betting markets because they're so stupid like the house always wins and i understand that right now we're in this like incredibly precarious economy and the way to get rich that was traditional doesn't feel accessible to us anymore like oh i'm gonna have this job for thirty years i'm gonna be a good person i'm gonna put money into my retirement accounts and it's all gonna work out for me it it feel we feel nihilistic about our finances and so why not just risk it all and gamble it away because maybe that will get you rich quicker and like that's a better idea but that's wrong i want to be clear that and also even if these apps have a pink interface they're not investment platforms these are not places to actually grow wealth they're entertainment so if you actually want to invest in your future stick to the boring stuff your index funds your high yield savings accounts pay down your debt save an emergency fund it's simple but if you want to gamble on the housewives like you want to have a little fun sure just admit it's for the drama not the dividends and that's what these are for okay and i don't know if you guys have been noticing but like nostalgia is back like the hannah montana twenty year anniversary special hillary duff is everywhere like all that we want is ip that we are already familiar with and loved and this is honestly an economic indicator because when people feel good about the future like they are investing in growth they are investing in newness they want stocks they want startups they want risk but when the future looks shaky they like to invest in the past and right now the future feels a little shaky we got global conflict going on we got crazy interest rates housing is unaffordable wages are lagging against inflation so it makes sense and instead of betting on what's next we are betting on what has already worked so yeah miley putting on her hannah montana wig was a strategy nostalgia fully converts in fact the nostalgia economy is a crazy business like we pulled a stat that the music rights market alone is valued at forty one point five billion dollars like if you're a bob dylan if you're the beatles like your catalogs are also being revived through tiktok virality because people are looking backwards instead of forwards and for investors these are income generating time capsules too because the past has predictable cash flow but what i also think is really crazy about nostalgia is that this is like a really human trait that when things feel shaky we look to the past like during the great depression that's when like gone with the wind popped off because people were like looking for stories from that age or like in the seventies when there was all of that unrest that was when greece became really popular popular and cheers which were stories from the fifties so or even during COVID everyone started to rewatch friends we were taking on grandma hobbies like making sourdough like we always look to the past for comfort when the future is scary so the psychology is very simple but the past will always stay winning when the future feels like risk okay now let's get into our tax episode because yeah we have the same uncle uncle sam baby let's go talk about him okay i think that we can all agree that housing is expensive like rent mortgage it doesn't matter which one you're paying it is your biggest monthly expense so the question becomes is it even doing anything for you like are you getting rewarded for that money well that's where bilt comes in bilt is a membership that rewards you with points on your housing payments whether you rent or you own and as of twenty twenty six that includes mortg payments too so every payment earns you points that you can redeem towards things that you're already spending on like built points are honestly so valuable you can exchange them for flights with partners like united hotel rooms with hyatt lyft rides or even purchases on amazon dot com personally i always use my points towards travel i just booked travel to los angeles for my book tour on it and what i feel like is also really underrated is their neighborhood concierge like built members can get help booking restaurant reservations fitness classes discovering new spots it's this very seamless lifestyle driven experience all connected to where you live just like from being a built member so i really feel like your biggest expense should feel a little more considered and give you rewards and with built it is so join the membership where you live at joinbuilt dot com t that's j o i n b i l t dot com t i've been a member since twenty twenty two and i've never regretted it okay we need to talk about quints because this is exactly the kind of brand that makes getting dressed easier smarter and cost quints is all about elevated essentials that feel effortless so like the kind of pieces that you can actually build a wardrobe around and everything is designed for layering and mixing so you're not just buying trendy one offs that you have no idea how to actually style like you're buying those staples that you can reach for over and over again and actually make getting dressed easy what they're really good at is nailing the basics but with quality that's made to last so like one hundred percent european linen and organic cotton and it shows the stitching the feel the way the pieces hold up season after season like these are clothes that really can earn a piece in your rotation so refresh your wardrobe with quint go to quince dot com financialtea for free shipping on your order and three hundred sixty five day returns now available in canada too that's q u i n c e dot com financialtea okay first question i've not seen these yet i am getting a raise at my company but it pushes me into a higher tax bracket misses dow jones should i say no okay first of all this is one of the biggest tax myths that refuses to die so i'm excited to be here and to myth bust because the answer is absolutely not you should one hundred percent take the raise if you make more money and you move into a higher tax bracket that does not mean that your entire salary is going to get taxed at that higher rate and you're going to end up making less money that's not how our tax system works and the easiest way to understand like how tax brackets works because trust me no one explains this to you is just to imagine buckets because we have a progressive tax system okay so imagine your income and imagine a bucket that first bucket is going to be taxed at a low tax rate so your first chunk of your income is going to go into that first bucket and it's going to be taxed at that level once that bucket is all the way filled up any extra money is going to be put into the next bucket which has a slightly higher tax rate then once that bucket is filled up your overflow is going into the next one at a slightly higher tax rate and and your income is going to keep filling buckets as it grows and each bucket as it progresses because it's a progressive tax system has a little bit of a higher tax rate so it doesn't matter if you're jeff bezos or you're me your first bucket is always going to have that lower tax rate and you're just going to keep incrementally paying more taxes the more that you make more money but only on that increase in money that you're making if that makes sense like here's the key thing that people get wrong is that that only that money in that higher bucket is taxed at the higher rate so like the money in your old earlier buckets is going to stay taxed at the lower rates so if you get a raise and it pushes overflow of your income into a higher tax bracket or bucket only that extra portion is going to get taxed more your entire salary is not going to suddenly get taxed at that higher rate it's just going to be that little bit of overflow that pushes you into that next bucket so please promise me if your boss offers you more money take it uncle sam might get like a slightly bigger slice of that top bucket but i promise you're still going to be earning more money you're never going to take home less money by getting a raise even if it makes your tax bracket higher because it is progressive and you're only going to be taxed more on that bit that pushed you over okay next question should i hire a cpa to do my taxes okay this is another question i get asked a lot and i've got to be ffr with you be freaking for real if your situation is pretty simple like you've got one job you got a w two maybe you got a little interest from a savings account you could probably file your taxes just using software millions of people do it every year and it's totally fine but i will say like if you've got multiple income streams if you've got freelance work if you've got a side hustle if you've got rental properties if you run a business damn taxes can get complicated very fast and that is where mistakes get expensive and also where hiring a cpa can actually save save you money because a cpa is not just someone who like files your forms for you in april the real value that you get from them is that they help you plan like my cpa michael we just switched misses dow jones to an s corp so that i can save money and that was something that he came up with like they will tell you things like hey if you contribute more to this retirement account you can lower your taxable income or like you should structure your income differently next year which is what happened to me so i will say my rule is if your taxes take like one hour or so to do and you're basically just typing numbers from forms into tax software which is annoying but you can do it i promise you probably don't need a cpa but like if your taxes have multiple layers call a professional and i will also say i've had very bad accountants before like accountants can be really boring and hard to talk to and i do believe that you can find an accountant who makes sense to you and that's really important to like advocate for yourself financially it took me a long time to find michael i'm happy to to give you his number he's amazing been working with him for years now but why i like him is that he's like a little bit hot and he is easy to talk to and he has good ideas he's good at helping me save money so that's important i used to have this other accountant who i just absolutely hated taking their calls and that you know i had to get rid of them help i got a four thousand dollars deduction is that good did i just save four thousand in taxes haley okay i'm sorry love i do not mean to be the bearer of bad news because i know that people love posting their tax refunds like they won the lottery but the truth is if you got a really big tax refund it sort of just means that you did your withholdings wrong like here's the thing when you have a job your employer takes taxes out of your paycheck every time that you get paid and sends them to the government that is called a withholding and when you file your taxes in april you're basically just doing the math to check like oh did i send the government the right amount during the year and if you sent too much you're going to get a refund but if you sent too little you're going to owe more so when you get a four thousand dollars refund what actually happened is you just overpaid your taxes during the year by four thousand dollars and the government is giving you your own money back so like i'm going to hold your hand as i say this but yeah like you basically just gave uncle sam a four thousand dollars interest free loan that is money you're not getting rewarded that's just your money that you've been giving to uncle sam at a zero percent interest rate and i want to be clear the goal with taxes is not to get the biggest refund possible the goal is just to get as close to zero on your refund as possible so if you want to fix that for next year though it's very easy just adjust your w four form with your employer if you lower the withholding a little bit more of your money is going to stay in your paycheck throughout the year instead of sitting with the irs which is way better and i do want to say for my self employed baddies this is your reminder to always make quarterly payments on your taxes that's really huge i didn't do that the first year that i had my own business and i owed a really big tax bill so make sure that you are putting aside thirty percent of your earnings every time that you get paid for your taxes and then every quarter that you are paying an estimation to the government of what you owe that is going to make your april so much better okay question i knew that we were going to get this why do billionaires sometimes pay less taxes than everyone else this is a very good question and i get it it is confusing and the reason is because they are not making money the same way that we do like most people are just earning money like through a salary you go to work you get a paycheck and then taxes come out of it immediately and then uncle sam gets paid before you even see the money but extremely wealthy people often structure their income really differently like take jeff bezos for years while he was running amazon his salary was only eighty k a year which like i'm sorry for jeff bezos like that's basically the income of a mid level corporate employee but obviously he's really rich so where was the money coming from because he was living like someone who was making way more than eighty k and the secret is that he was doing a strategy that rich people love to do called buy borrow die and i want you to think of buy borrow die like this rich people try not to sell their assets because selling triggers taxes so instead they do these three steps so the first step is they buy so first they buy assets that grow like usually stocks or companies jeff did this with amazon like instead of taking a big salary he took most of his earnings in amazon stock like he owns billions of dollars of amazon shares and when that stock goes up in value he doesn't pay taxes just because it went up he only pays taxes if he sells so he's sitting on this valuable asset but he's not paying taxes on it even though it's increasing in value because taxes are only paid if he sells but he needs cash flow right so what he does that's really smart is instead of selling that amazon stock to get cash rich people like jeff are going to buy borrow money using their stock as a collateral so jeff could go to the bank and be like hey i have fifty billion dollars of amazon stock can i please borrow five hundred million dollars against it and of course the bank is going to say yes because the stock is super valuable and so now bezos has five hundred million dollars in cash to live on and the craziest thing about this hack is that loans are not considered income so they are not taxed so he's getting spending money without triggering any taxes and while keeping all of his assets intact it's really crazy and then the third step in the process and he basically he will do this until he dies which is the third step and when someone dies in the us their assets get a step up in basis and so that basically means that the tax history resets to the current value for their heirs so for example bezos got amazon shares for almost nothing they are now worth billions if he sold them he would owe huge capital gains taxes but if he dies holding them his heirs will inherit that stock at the current value so the past gains basically will disappear for tax purposes so the strategy is buy assets that grow like he did with amazon stock borrow against them instead of selling because it is non taxable you're just going to get income and you can live off of it but you want to pay taxes on it and then you can die and pass your assets onto your heirs with taxes minimized so yeah rich people basically live on loans backed by their investments instead of selling them which helps them avoid taxes during their lifetime which is crazy and i know that this feels really unfair it is but here's the thing like you're listening to financial tea i always give you the juicy ass scoop on how to help your own finances and this is not some secret trick that only billionaires can use like regular people do this on a smaller scale all the time you can borrow against your house you can take a margin loan against your investments you can use a line of credit instead of selling assets like there are ways to borrow against things that you have that are valuable at a low interest rate but you just have to be really careful because you know if it goes the other way say amazon went to zero which you know now it's it's too big to fail i don't think that would ever happen but like if you're doing this on a smaller scale it could go the other way and that's what makes it a little bit risky you then you're on the hook for that loan and it puts you in a bit of a precarious situation so i would just be really careful but good to know that we can also do this you know billionaires are just like us we're all just taking loans against our investments my friend told me if you start a business you can write everything off like your car your rent your plastic surgery is that true okay well the truth is for plastic surgery kind of this is my favorite tax deduction story ever okay there was a dancer in the nineties named chesty love who worked at a strip club and she got these insanely big breast implants like we are talking fifty six triple n implants not street legal and she argued in court that they were not cosmetic surgery they were a business expense because they helped her earn money as a performer and the irs obviously disagreed and denied the deduction but she took the case to court and our girl chesty won why you might ask well because she was able to prove something very specific those implants were not something she would reasonably use in her everyday life and they directly increased her income as an adult entertainer so the court ruled that they were essentially like a stage prop like the same way that you would like have a costume that's what her implants like how they functioned and now okay before everyone listening gets excited and calls their plastic surgeon and starts planning their own creative tax deductions i will say the case is famous because it is incredibly unusual and i will say that the irs rule is that business expenses have to be ordinary and necessary for the job but i think that that line has become a little blurred as people have become lifestyle influencers because obviously like if you're doing things for your lifestyle it's earning you money for your job as a lifestyle influencer and like shouldn't it be a tax write off like your botox your wardrobe your vacation to cabo if you're posting from it so i get that there's a gray area i think you need a good accountant to figure out like where you want to push and where you want to pull back because the irs isn't stupid but and i will say like with clothing unless it's a required uniform that you can't really wear in normal life like think about like a chef's jacket or safety gear they're tough on that and the irs the rule that they usually use is pretty simple like the expense has to be clearly tied to earning income for the business and it can't be just like something that you would normally buy for your personal life like i don't think that chesty love is getting those huge ass implants because it's like fun i think she was getting them because it like made her a lot of money and i'm sure the moment that her career was over she got those popped out you know so if it looks like a lifestyle upgrade with a tax write off attached that is usually where people get into trouble but i will say like if you have a good accountant you can write off a lot of stuff i write off so much stuff but it's like you know my life is being misses dow jones so shouldn't i shouldn't i long drive ahead tiktok shows road trip spots car hacks travel playlists best routes hidden cafes scenic stops drive smarter explore more download tiktok now good sleep is everything that's why ali's science back support is made with a blend of melatonin and l theanine for both kiddos and grownups so when your mind won't switch off you've got something that can help your racing thoughts and restless nights won't stand a chance find ollie sleep solutions for the whole family at ollie dot com that's o l l y dot com okay next question how can someone with a regular ass salary legally get the tax advantages and deductions that billionaires get okay first of all i love this question because i feel like people think billionaires have some sort of secret tax system and the like handing them a cheat code they don't they're just really good at using the rules that already exist and they put a lot of money and energy into like leveraging them and they really know what the rules are so but just because you're not a billionaire doesn't mean that we can't find some loopholes too so if you have a regular ass salary and you want to lower your damn tax bill the move is to use the same tax shelters that these rich people are using and the first one that we always talk about is retirement accounts when you put money into a four hundred one k or traditional ira or a health savings account that money comes off of your taxable income which means that the government literally will tax you and pretend like you made less money so like if you made eighty k and you put ten k into your four hundred one k you're now paying taxes as if you made seventy k and billionaires do this too it's just with way bigger numbers so like not only are you putting money away towards retirement which is amazing because you're growing wealth but you're also lowering your income in the moment your taxable income in the moment and i just mentioned this but also health savings accounts are so important to like know about if you want to be tax savvy like if you have a high deductible health care plan you can put money into a health savings account and that money goes in tax free it grows tax free and it comes out tax free if you use it medical expenses and you can invest it like hsas are truly the unicorn triple tax advantage unicorn of accounts and people sleep on it so make sure that if you have a high deductible healthcare plan that you're contributing to your hsa and investing the money in that account and then the third thing that is great if you want to avoid taxes is just to own something like the tax code loves owners if you own investments like stocks or real estate like you get access to capital gains tax rates which are often lower than regular income tax or like if you own part of a small business or a side hustle suddenly things like your laptop or software or part of your rent or travel related to work can all become deductions so i would say maxing out tax advantage accounts is huge that's why i always say that's like you know the first step in your investing journey and also to make sure that you're putting money into your hsa which i feel like like people don't know about but it's the best account ever and then yeah owning something owning stocks owning real estate that's the way to do it baby i also got a lot of questions about how i do my taxes and i have to be so for real i don't because i have a business and what did i say at the beginning of this episode like if you have a business if your taxes are complicated i have a lot of different income streams not to brag and so i need someone to help me optimize it and so i use michael michael savoci love him to death um every financially responsible woman has a michael we all have a michael and we have a lawyer all adventurous women do um and he really knows the irs rules back and forth so i do not have to spiral reading tax blogs at night and i think that at the point that i'm at it's good to have professional help i used to use the software but i will say that i basically have always had an accountant because i only had a w two job for like like seven months or eight months when i worked for lauren michaels before i got laid off up until that point i was always hustling like four different income streams and so i always needed someone to help me with my taxes and yeah that's been michael and also help with like investment stuff because i have a lot of investments again brag and they you have to manage that in its own specific way as well and i give everyone michael's number so like if you want michael to help you with your taxes comment below i have no affiliate link towards him i just like trust him and think he's great and he has you know he does he's jack jack coins accountant too i gave him i gave him to i gave michael so i'm happy to to connect you with michael if you need a michael one thing that i will say that is really going to help you with your taxes is like the same way that i always tell you guys to have a money date have a set time every single month where you are looking sitting down with your finances make a tax date like if you're listening to this episode right now go into your calendar and figure out what day if you do your own taxes that you're going to do them like mark it down do not move that date unless like taylor swift wants you to come to her wedding like that's it that's the only thing that we will allow you to move it for but i think that that is like not for a few months anyways so it shouldn't really be a problem but that is like the biggest thing is just having that set time make an appointment with yourself to get this done because otherwise it's just going to weigh on you and be something that you're doing last minute and it really doesn't need to be it can be something that you are in control of instead of making it in control of you and also like same thing with everything financial it's not that hard yes if you have complicated taxes you should get an accountant but like for most people bleep bloop you add some you know numbers into a form and you're done and this is something that you have to do every year so no offense we just sort of have to get over it and get going and make sure that you max out those tax advantaged accounts including your hsa because that is going to drive down your taxable income and make it so you are hopefully taxed at a lower rate for that you know income in the top buckets shout out to buckets hope you guys love that analogy okay anyways i gotta go because uncle sam has been texting me and i have to like talk to him about something really important about our family but please don't forget to subscribe don't forget to rate comment if you need anything from me if you want michael's number pre order my book and stay rich hey psst you didn't hear this from me but normal gossip is back for its ninth season join me rachel hampton as i share the juiciest gossip from the real world with some very special guests this season we're bringing back some old friends a radiotopia buddy and for the first time ever a nobel laureate that's right we have malala on season nine normal gossip is out on all your favorite podcast platforms
Aired: April 2, 2026
In this rich and accessible episode, host Haley Sacks (aka Mrs. Dow Jones) breaks down the basics and not-so-basics of U.S. taxes. She lays out the practical rules, busts common tax myths, explains how billionaires minimize their tax bills, and gives actionable advice to help listeners legally "game the system" for themselves. Delivered with her irreverent humor and signature pop-culture-laced tone, this episode demystifies taxes, offering practical strategies that listeners at every income level can use.
"Making money and managing money are two completely different skill sets...The difference between someone who feels constantly screwed by taxes and someone who just like pays them every year and moves the fuck on with their life is just understanding the rules." (09:55)
Overview of oil market turmoil and its effect on everything from gas prices to grocery costs.
Market correction defined as a regular part of investing, urging listeners not to “panic sell.”
"Correction means the market has dropped ten percent from its recent highs, so it’s basically the market’s way of having a Britney breakdown… but this is actually really normal." (14:45)
Prediction markets (e.g., Kalshi, Polymarket) are targeting women with lifestyle bets, but these are gambling, not investing.
Nostalgia as an economic indicator: when the future feels risky, people and investors flock to the comfort of the past.
"When people feel good about the future, they're investing in growth...But when the future looks shaky, they like to invest in the past. Instead of betting on what's next, we're betting on what has already worked." (21:10)
Myth Busted: Accepting a raise never causes you to take home less money due to brackets.
“Imagine your income and imagine a bucket… your first chunk of income is taxed at the lowest rate, then the overflow goes into the next bucket taxed a bit more, and so on. Only the money in the higher bucket is taxed at the higher rate.” (29:32)
“A CPA is not just someone who files your forms… they help you plan. My CPA Michael got Misses Dow Jones switched to an S-corp to save money.” (33:15)
“You basically just gave Uncle Sam a $4,000 interest-free loan. The goal with taxes is not to get the biggest refund—it’s to get as close to zero as possible.” (36:18)
"Bezos was living like someone making way more than 80k. He was doing a strategy rich people love: buy, borrow, die. ... Loans are not considered income, so they're not taxed. He's getting spending money without triggering any taxes." (39:18)
“She was able to prove those implants were not something you’d use in everyday life and they directly increased her income as a performer… So the court ruled they were like a stage prop.” (44:10)
"If you made 80k, and you put 10k into your 401(k), you’re now paying taxes as if you made 70k..." (48:00)
“Go into your calendar and figure out what day you’re gonna do your taxes. Don’t move it unless Taylor Swift invites you to her wedding.” (54:02)
| Timestamp | Segment/Question | |-----------|------------------------------------------------------------------------| | 09:55 | On celebrity tax trouble & the difference between earning and managing | | 14:45 | Market correction and advice not to panic sell | | 21:10 | The “nostalgia economy” as an indicator of tough financial times | | 29:32 | Myth-busting tax brackets ("bucket" analogy) | | 33:15 | When you need a CPA vs. tax software | | 36:18 | Why big tax refunds aren’t actually “free money” | | 39:18 | Explaining “Buy-Borrow-Die” billionaire tax strategy | | 44:10 | Chesty Love's lawsuit and the limits of business deductions | | 48:00 | How regular people can lower their taxes: 401(k), HSA, deductions | | 54:02 | The importance of scheduling a “tax date” with yourself |
Haley Sacks’ delivery is witty, approachable, and often irreverent. She situates technical advice inside real-world, pop-culture anecdotes—"shout out to buckets"—and breaks down intimidating concepts with metaphors (Britney breakdowns, market corrections as relationship fights, etc). She encourages listeners to be proactive, not anxious, and closes by urging everyone to pre-order her book, subscribe, and "stay rich."
This episode is a practical, myth-busting, and often hilarious guide to understanding U.S. taxes for regular people. It covers all the basics—from why you should always accept a raise, to how billionaires use tax laws to their advantage, to which deductions are legit—and gives actionable steps for everyone to legally lower their tax bill. By the end, you’ll know what to do, why it matters, and how to not get played by Uncle Sam.