10 Tax Moves Everyone Should Review Each Year

Join Andrew’s FREE Investing for Beginner’s Masterclass. Click the Link Here 👈 Join the community built to help you master your money, stay accountable, and reach financial freedom. 👉 Try Master Money Academy free for 7 days today! In this episode of The Personal Finance Podcast, Andrew breaks down the 10 tax moves every high earner needs to make before year-end, covering how to max out tax-advantaged accounts, adjust your W-4 withholding, harvest tax losses, time Roth conversions, optimize your HSA, give to charity more efficiently, capture business deductions, and run a forward-looking tax projection so you stop reacting to taxes and start controlling them. Join The Master Money Newsletter where you will become smarter with your money in 5 minutes or less per week Here! Partner Deals Indeed: Start hiring NOW with a SEVENTY-FIVE DOLLAR SPONSORED JOB CREDIT to upgrade your job post at http://Indeed.com/personalfinance Join the loyalty program for renters at joinbilt.com/PFP Go to http://policygenius.com to get your free life insurance quote. Thanks to Fundrise for Sponsoring the show! Invest in real estate going to http://fundrise.com/pfp Get 50% Off Monarch, the all-in-one financial tool at http://www.monarch.com/PFP Find your next dream home, start searching now. Download the http://Realtor.com app today DeleteMe: Go to https://joindeleteme.com/PFP20/ and Use Promo Code PFP for 20% off! Resources Mentioned: Master Money HSA Tracker Connect With Andrew on Social Media: Instagram TikTok Twitter Master Money Website Master Money Youtube Channel Learn more about your ad choices. Visit megaphone.fm/adchoices

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• 0:00Andrew Giancola?

  When I started the Personal Finance Podcast, I had no idea how big it could become. I just knew I had something I wanted to share, so I started putting it online. And looking back, I definitely wish I would have started a decade earlier. One of the horror parts about building something online, though, is making it look professional. A website used to mean hiring a developer, figuring out design, and potentially spending thousands of dollars. In fact, on my website, I spent tens of thousands of dollars. That's what impressed me when playing around with Hostinger's AI Website Builder. I told it what kind of website I wanted, and I built the first version in minutes. No coding, no designer, or developer needed. And Hostinger doesn't stop at launch.

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• 1:29Andrew Giancola?

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• 2:14Andrew Giancola?

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• 2:25Speaker 01

  Wayfair, every style, every home.

• 2:28Andrew Giancola?

  On this episode of the Personal Finance Podcast, 10 tax strategies you need to review annually.

• 2:43Andrew Giancola?

  What's up everybody and welcome to the Personal Finance Podcast. I'm your host Andrew, founder of MasterMoney.co. And today on the Personal Finance Podcast, we're going to be diving into 10 tax strategies that you need to review annually. If you guys have any questions, make sure you join the Master Money Newsletter by going to MasterMoney.co/newsletter and don't forget to follow us on Apple Podcasts, Spotify, YouTube, or whatever podcast player you love listening to this podcast on. And if you want to help out the show, consider leaving a five star rating and review on Apple Podcasts, Spotify, or your favorite podcast player. Now today, we're going to be diving into 10 tax strategies that you need to look into every single year. Now, my goal with this episode is to give you tax strategies that are going to,

• 3:28Andrew Giancola?

  A, help you save money on taxes, whether you are a W-2 employee and/or if you are a business owner. We want you to learn how to save on taxes. Secondarily, my goal is to show you some ways where if you want a bigger tax refund or a smaller tax refund, how to make sure that you get that and how to adjust your withholding based on that. Number three is we're going to be diving into some advanced strategies when it comes to your retirement accounts, when it comes to investments and investment gains, and try to help you save as much money on taxes as possible. Now, this episode is not going to be a deep dive on business deductions or a way to strategize business deductions with an LLC. We will do something like that in a future episode.

• 4:12Andrew Giancola?

  So if you are interested in that, please let me know. But our goal is to try to help you as much as possible. Now, one big thing I want you to know is that if you don't have a CPA in your corner and you feel as though you have businesses or you have some advanced tax strategies that you feel as though you could take advantage of, then hiring a CPA is probably one of the best overall things to do. Just remember, I'm not a CPA. You need to check with a CPA. On your personal situation to make sure you are making the right moves based on your income and based on your tax strategies that are available to you. Each and every single one of us has very different tax strategies available to us based on what type of business we have, how we're incorporated, how we want to think about that, or if we are just a W-2 employee.

• 4:55Andrew Giancola?

  And so for a lot of folks out there, this is something that is going to help you as we go through these steps to reduce the overall amount that you're going to be paying in taxes. And Master Money Academy, we actually have an entire document that shows people the questions to ask when you want to interview a CPA. So if you're interested in that, check out Master Money Academy down below. If you're looking for the questions to ask a CPA down below, we give you all the interview questions that you should be asking. So I am really pumped for this episode. We're going to get into the first one right after this breaks. Without further ado, let's get into it.

• 5:28Andrew Giancola?

  So number one is, and longtime listeners know this one is coming, is we want to make sure that we are maxing out tax advantaged accounts. If you are a W-2 earner, or you are someone who has a nine to five and do not have a business on hand, this is one of the best tax advantages that you have at your disposal, is looking at tax advantaged accounts. What is a tax advantaged accounts? Well, there's a bunch of them that we will go through here today, but you need to go through each one of these and see which one fits your specific situation. Number one is a 401k, and everybody has most likely heard of a 401k. It is the account that is going to help most of you. Now, there are also other pre-tax accounts that will fall into line with this. You could think of a 457, a 403B. All of these are very similar to this pre-tax account of a 401k.

• 6:12Andrew Giancola?

  Now, a traditional 401k in 2026, you can contribute $24,500 to your 401k. And when you contribute those dollars, you are not taxed on that $24,500 in that given here. Now, once you have that money invested in your 401k, the money grows. And when you pull the money out, that is when you get taxed on those dollars. But the key here is, most people are anticipating pulling that money out after the age of 59 and a half, which is when the penalties will end on the 401k. So you can't withdraw from a 401k until after the age of 59 and a half. But once you have the ability to be able to do that, your overall thought process here is to be in a lower tax bracket than where you are right now.

• 6:57Andrew Giancola?

  If you are in your high earning years, and I'm talking to my folks in the 30s, 40s, 50s, if you are making a lot of money right now, a 401k would be a big consideration for a lot of you out there. And if you're in the 30% tax bracket or above, this is a definite consideration for you because you need to reduce your overall taxable income. But even people below that range, you also want to look at this because it is one of the most powerful ways to build wealth. So you can shelter $24,500 per year just by looking at the 401k. Now, a lot of you out there that are self-employed were like, I don't have access to a 401k. Am I just stuck with a traditional IRA? Actually, no, this is something very important to note. Even if you just have an LLC, if you run your own business and you are the solo person in that business,

• 7:41Andrew Giancola?

  or maybe just your spouse works with you in that business, you are actually eligible for a solo 401k. Now, why is this so powerful? Well, the solo 401k is actually one of the most powerful accounts overall because you can A, put in that $24,500 per year, but B, there is also the employer portion of the contribution where you can put 25% of compensation as defined by the IRS rules. So your total contribution limit for someone who has a solo 401k is $72,000 that you can shelter from taxes in 2026. And this is not counting catch-up contributions. You have a ton of potential here in the solo 401k to shelter lots of money, but you cannot have employees in that business.

• 8:26Andrew Giancola?

  If you have employees in that business, you can look at things like a SEP IRA or a simple IRA. Those are going to be your best bets and your best options to shelter that money from taxes. Now, there's also a Roth solo 401k, which is going to allow you to have that tax-free growth. So in that given year, when you put that money in, the money has already been taxed, then the money grows tax-free and you can pull the money out tax-free. So if you feel as though in the future you are going to be in a higher tax bracket, then that would be the situation. Where you want to look at potentially the Roth 401k and the Roth option. So there is a ton of amazing things that you can do here. And every single dollar that you shelter from taxes in a traditional 401k, you can utilize to leverage going forward in the future. Now let's talk about the Roth IRA because it's the same exact thing.

• 9:11Andrew Giancola?

  The Roth IRA, you could put $7,500 per year in 2026. Money goes in, that's already been taxed. You earned it from your paycheck. You have it in your checking account. You send it over to your Roth IRA. And then your Roth IRA grows tax-free and you could pull the money out tax-free. Your employer may also offer a Roth 401k, which is another great option for those of you who are really interested in the Roth. Now, the Roth is so powerful because if you contribute money to that Roth IRA, let's say you max out your Roth IRA over the course of 30 years. You have a million dollars in that Roth. Well, about $850,000 of that is going to be completely tax-free because it's the growth of your money. The growth is the majority of your money in a Roth long-term. And the more that you can get in a Roth, it is absolutely incredible what you can do. There's no RMDs, meaning the government's not going to require you

• 9:56Andrew Giancola?

  to withdraw money from that Roth IRA at a certain age. And when you do withdraw that money, you never have to pay taxes again. It is a really amazing way to shelter your dollars from taxes long-term, which is why we love it so much and why we put it where we put it in our investing order. And so this is really, really important to make sure that you look at the Roth IRA. So if you are thinking through, well, what is my strategic order that I need to think about when it comes to these investments? I like to, A, first get your employer match, whatever your employer match is for your 401k. If you can get, take advantage of that, that is a amazing way to get your dollars growing. Then contributing to something like your HSA, which we will talk about here in a second. Then funding your Roth IRA or your Roth 401k.

• 10:39Andrew Giancola?

  And if you make too much money, you can do a backdoor Roth contribution. And then also looking at your 401k. And that is going to be a big, big deal for a lot of you out there. So these are just some of the ways that you can shelter taxes is using retirement accounts. There's a bunch of other retirement accounts that are out there, but these are the ones that are going to pertain to most people. Now let's get to number two, which is adjusting your withholding.

• 11:02Andrew Giancola?

  So one of the big things that a lot of people do is they will go out and they will give the government a free loan. And you may not even realize that you are doing this. You are giving the government a free loan every time you get a tax return. So when you get a tax return, that means you actually overpaid the government in taxes and you gave them a free loan throughout the entire year. Those dollars could have been working for you in a Roth IRA or a 401k, or you could have been spending those dollars on a vacation or saving up for a down payment on a home. But instead, you gave the government a free loan. But that is okay, because guess what? You can adjust your withholding with a form called the W-4 form. So here in the US, the W-4 form is going to allow you to change your withholding and to figure out, A, if you want to make sure that you're not giving the government

• 11:46Andrew Giancola?

  a free loan and you want to have a lower tax return and a higher paycheck, then you can adjust it that way. Or some people may actually want a big tax return. It's for savings for them and they like the idea of having a tax return because every single time they get that tax return, then they put those dollars into a Roth IRA or a 401k. And the psychology behind that is just that is the way they want to be disciplined. You can also adjust your withholding to get a bigger tax return if you wanted to go that route. That's not the route I would ever want to go because the power of compound interest and the power of getting your dollars invested as early as possible is really powerful. But if you want to hack your brain or hack the system, then that is something else that you can absolutely do. And so this form called the Form W-4 is something where you can adjust your withholding

• 12:29Andrew Giancola?

  based on what you are trying to do. Now, your employer uses your Form W-4 to calculate how much federal tax is going to be withheld based on a couple of factors. First, what your filing status is. So are you filing married filing jointly? Are you single? Are you filing married filing separately? There's a bunch of different tax filing statuses that are on Form W-4. The number of jobs that you have is the second one. Dependence that you are going to claim is the third one. So a lot of people use Form W-4 to have their dependents on there. And then additional income or deductions that you expect will also be on Form W-4. Now, why does this matter? Because if you have too much withheld on Form W-4, that means you're going to get a big refund. So if you're the person that every single- You're bragging about your refund and saying, hey, I got this huge massive refund.

• 13:15Andrew Giancola?

  This is absolutely amazing. Then you gave more money than you needed from your paychecks to the government. And if you get a huge refund at tax time, then you gave your, the IRS, an interest-free loan. But if you give too little taken out, then you could owe the IRS money by the end of the year. So this is a game of balance. This is a game of trying to figure out exactly where you will land and adjusting that withholding based on this. Let's say, for example, you tell the IRS on Form W4 that you're going to make $100,000. And you end up making $120,000. Well, if that is the case, you will have taxes withheld on $100,000 of your income. And you're going to owe taxes at the end of the year on the difference, that $20,000.

• 13:58Andrew Giancola?

  And so for most of you out there, if you're not disciplined enough to make sure that you have an emergency fund or enough cash set aside in case this happens, then I would continue trying to withhold maybe a little more, slightly more than you think is available. But if you want to reduce the amount that is getting withheld and try to get as close as possible, then I would adjust your Form W4. Now, most people are not trying to make sure that you get a big tax refund. Most of your employers are trying to get as close as possible to this number. And you just end up having a tax refund based on a number of different factors. And so the closer you can get, and you can ask your employer for this form to adjust this if you want to. But the closer you can get to the correct number, the closer you can get to not owing money and not getting any money back. That means you have a larger paycheck every single month.

• 14:41Andrew Giancola?

  And this can be a great way to help you throughout the year. So if you are someone living paycheck to paycheck, and you're the type of person that you maybe get $4,000, $5,000, $6,000 every single year in a tax refund, it may be worth it for you to adjust your W4 to give yourself a little bit of breathing room, to give yourself the reduction of stress and anxiety around your money. This can really, really help you long-term. Now, there are other times that you also want to review your W4. When you get a raise at your job, you definitely want to take a look at the W4 and see if you want to adjust it. If you get married or you get divorced, that is another time to look at this. If you have a baby or add dependents, that is another great time to look at your W4. If you buy a house, if you have a side business, all of those Are great reasons. And so how do you adjust your W4?

• 15:24Andrew Giancola?

  You fill out Form W4 and then you just send it over to your employer. That's the way it works. They will process the paperwork and you can ask them, hey, what's the process to sending you my W4? Typically, it's probably sending it over to HR or payroll and getting that done right. Now, because the form is not completely straightforward and it can be difficult if it's your first time doing this. The IRS does provide something called a tax withholding estimator. And this can help you online estimate how much tax you should have withheld based on your actual income, deductions, credits and filing status. So this can help you tremendously if you are trying to do this calculation. And this isn't a set it and forget it form. You're going to have to look at this more frequently than you think. And if you are someone out there who really wants to make sure that this is really on a fine line,

• 16:06Andrew Giancola?

  I would definitely recommend setting up an alert every single year to look at your W4 form, especially if you've got big changes in your life and a lot of us are having big changes right now. And I know a lot of listeners or you're having kids, you're getting married or there's things that are going on. And so you want to make sure that you have that in place. All right, let's jump to number three, which is tax loss harvesting. So if you don't know what tax loss harvesting is, it is something that you do in a taxable brokerage account, where if you have losses in your taxable brokerage account, you can make sure that you sell those stocks at a loss, not because you want to lose money, but so that you can save money on taxes. Now, this strategy is called tax loss harvesting. Now, for those of you who have smaller accounts, if you have a smaller brokerage account and you have, you know, a hundred thousand dollars in a brokerage account, this may not be worth your time and energy to go out and do.

• 16:49Andrew Giancola?

  But if you're someone who has a very large account and either you made a lot of money in a specific stock and maybe another stock went down, then it might be worth looking at tax loss harvesting so that you can reduce your overall taxable interest. Now, I highly recommend that if you are going to do tax loss harvesting, you talk to a CPA and have conversations about this. This is something that is very, very important for a lot of folks out there. Another thing is there are a lot of robo advisors out there who can help you do this automatically as well throughout the year. One of the biggest pitches from robo advisors is that they do help you tax loss harvest. And so this is something that if you want to look further into this, you absolutely can. So what is the true definition of tax loss harvesting? Well, let's look at it. Tax loss harvesting is the process of selling an investment at a

• 17:31Andrew Giancola?

  Loss intentionally for the purpose of realizing a capital loss, which you can use to offset taxable gains and ultimately reduce your tax bill. So instead of letting losses do nothing, you can convert them into tax savings. And so again, for a lot of folks out there, this is going to be something that can help you offset some of your capital gains if you want to do this. So the IRS lets you use realized investment losses in taxable accounts to reduce your taxable income. But there are rules to this. There's a lot of rules where people were gamifying the system. And so the IRS puts some rules in place. First, losses offset gains in the same type. So short-term losses offset short-term gains and long-term losses offset long-term gains.

• 18:15Andrew Giancola?

  And then number two, it reduces your ordinary income up to $3,000. So if total losses exceed total gains in a year, you can deduct up to $3,000 of XX loss. And this is going to help you with your ordinary income, i.e. wages. And so if those losses exceed $3,000, then you can carry those forward to future years indefinitely. So if you have a really bad year, you are really getting hammered in a specific year, then that might be a great time to do this. Like you could think of 2007, 2008, 2009. That was a year where most likely a lot of people were offsetting gains to future years forward because they got up to that $3,000 limit and they were pushing that forward. So let me give you an example, okay? An example of this would let, let's say you sold stock A and realized a $10,000 gain.

• 18:59Andrew Giancola?

  And so you had this gain because you sold this specific stock at $10,000. And then you sold stock B at a $10,000 loss. You just neutralized your entire gain, whereas you're not going to have to worry about paying taxes on those dollars. So this is a strategy where if you have huge gains and you have to sell those stocks and you have huge losses, this can help you in that area. Now, there's one thing you need to know, which is called the wash sale rule. Now, the wash sale rule states this, and let's look at it together. If you sell an investment at a loss and buy the same or substantially identical security within 30 days before or after the sale, the loss is disallowed for tax purposes. So you can't go out and let's say sell Nvidia and then go back and buy Nvidia. Less than 30 days later or an identical stock.

• 19:43Andrew Giancola?

  So when should you do task loss harvesting? There's a couple of times you could do it. You could do it at year end, which is when most people do it. You could do it after a market drop. That is a timeframe where if there is a opportunity where there's a 20% drop in the market, then that could be a time where you look at this. You can look at it if you do have some really big gains or when rebalancing triggers those losses. So sometimes rebalancing your portfolio does this for you automatically. And so you don't even have to worry about it and that is going to help you. And really the cool thing about rebalancing is if you do rebalance, you can go and hey, sell your stocks to buy more bonds. And then all of a sudden that is a tax loss harvest. Sell your stocks to buy some bonds and all of a sudden you can tax loss harvest that way as well. So common mistakes to avoid is one, triggering a wash sale. You do not want to be buying that light kind of stock because then you just did all of this for nothing.

• 20:27Andrew Giancola?

  Two is over trading. That is never worth it. We are long-term investors here at the personal finance podcast and master money. We are not short-term investors. Three is ignoring transaction costs. If you have transaction costs based on selling these investments, it may not be worth the time and energy. And then failing to lose track of your carry forwards. So if you do get carry forwards, you don't want to lose track of those as you do this. Now there is a special note that I want to make on this episode and this could change at any given time. But there right now on in crypto, there is no wash sale rule. So let's say, for example, you bought Bitcoin at a tight when it was at 120,000. And right now, at the time recording this Bitcoin is right around $70,000. So right now, a lot of you may have losses if you own Bitcoin and you bought it at the height.

• 21:09Andrew Giancola?

  Well, in that scenario, right now there is no wash sale rule when it comes to crypto. Now Congress, I think is having conversations about this. Most likely this will change at some point in time, but there could be a pocket of time right now where you can do some tax loss harvesting with crypto and have the ability to buy back that investment and look deeper into this. But talk to your CPA about this. This is not tax advice. I am just giving you some information that is out there. It's if you had big gains in crypto over the last couple of years, you could definitely look at this and see if you can fix that. All right, let's jump into number four right after this break. It's kind of amazing how much can change in just a single year. Every summer, the kids are a little bigger, a little more independent, and life looks a little different than it did the year before.

• 21:53Andrew Giancola?

  And it reminds me that while we can't predict the future, we can prepare for it. That's one of the reasons I like PolicyGenius. See, PolicyGenius isn't an insurance company. They're an online marketplace that lets you compare life insurance quotes from some of America's top insurers, side by side, for free. And their licensed team helps you compare coverage, prices, and terms, answers your questions, and even handles the paperwork so you can get the right policy without the hassle. For me, having life insurance isn't about expecting something to happen. It's about knowing my family is protected so I can actually enjoy these moments together instead of worrying about what comes next. And with PolicyGenius, you can find 20-year life insurance policies

• 22:36Andrew Giancola?

  starting at just $276 a year for $1 million of coverage. Head to PolicyGenius.com to compare life insurance quotes from top companies and see how much you can save. That's PolicyGenius.com. If you've been listening to this show for a while, you know it's not just me anymore. It takes a great team behind the scenes to make everything happen. And if I had to hire someone tomorrow, I'd want someone who could jump right in and make an impact. That's why I'd use Indeed Sponsored Jobs. When workplace chaos hits, Indeed Sponsored Jobs helps you reach qualified candidates faster. Your job gets boosted in search results, so you're spending less time searching and more time interviewing the right people. Plus, you only pay for results, which I absolutely love.

• 23:21Andrew Giancola?

  Sponsored jobs posted directly on Indeed are 95% more likely to report a hire than non-sponsored posts. That's a huge advantage when you're trying to grow your business. Spend less time searching and more time actually interviewing candidates who check all of your boxes. Less stress, less time, more results. When you need the right person to cut through the chaos, this is the job for Indeed Sponsored Jobs. And listeners of this show will get a $75 sponsored job credit to help get your job. The premium status it deserves at indeed.com/podcast. Just go to indeed.com/podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com/podcast. Terms and conditions apply. Need to hire?

• 24:06Andrew Giancola?

  This is a job for Indeed sponsored jobs. If you've heard any recent episode of Health Corner, you know that I have spent the last few years trying to optimize my sleep. I've tried sleep trackers, cooling my room, changing my nighttime routine, all the different things, but nothing really matters as much as having the right mattress. And that's one of the reasons I love Leesa. A great mattress is one of those things that you use every single night and you spend a third of your life sleeping and it can make a huge difference on how you feel the next day. Leesa has mattresses designed for different sleep positions and comfort preferences. And their sleep quiz can help you get matched in less than two minutes.

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• 25:30Andrew Giancola?

  And we've had times where we thought we knew the bottleneck, only to realize later, the real issue was somewhere completely different. That's exactly what today's sponsor, Scribe, helps solve. Scribe is a workflow AI platform trusted by 94% of the Fortune 500. And Scribe Optimize turns real workflow data into decisions your AI strategy actually needs, automatically capturing how work happens across approved apps, surfacing inefficiency and opportunities with no interviews and no And no extra work from your team, which is the key. And the live dashboard shows where work is happening, how much time it's taking and where the biggest opportunities are right now. It automatically discovers workflows across multiple tools,

• 26:14Andrew Giancola?

  then highlights your biggest inefficiencies and gives AI-powered recommendations with estimated time-saving. You know I love saving time. It's also built with privacy in mind. It only runs across approved business applications. User-level data is anonymous by default and sensitive information is automatically redacted and never leaves your firewall. To see optimized action, head describe.how/pfp and mention PFP for a 30-day risk-free trial. That's S C R I B E dot H O W slash P F P. All right, number four is to review Roth conversion opportunities. So what is a Roth conversion and how does this work? Well, a Roth conversion is one of the most powerful tax planning tools for a lot of folks out there.

• 26:59Andrew Giancola?

  And because of this, a lot of people want to move money that is in a tax-deferred account, something like a 401K or a traditional IRA, and they want to move it over to a Roth account where it can grow tax-free forever. But if you do this strategically and you do this at the right time, you can save a lot of money on taxes. And so the way that this works is you take money, and let's say it's in a traditional IRA. You put money into that traditional IRA, then you convert that money to the Roth IRA. And when you convert that money to the Roth IRA, you're going to pay taxes on those dollars. Because since it's in a traditional IRA, you have not paid taxes on those dollars yet because you got that tax deduction upfront. And now you are paying taxes when you convert it to a Roth IRA. Well, why would you want to do this? Why would you want to pay taxes on something when you deferred those taxes for future you? Well, here's the variables that are going to matter.

• 27:43Andrew Giancola?

  Number one is your current marginal tax bracket. And then number two is your future tax bracket. Because if you think that in the future, you are going to be in a much higher tax bracket than you are right now, then converting that money when you're in the lower tax bracket could be beneficial for a lot of people. Number two is if you think there's going to be some expected law changes around taxes, then you can also do a Roth conversion during those given year. Or if you expect some big income in retirement, maybe you have some RMDs coming up or you have some big... Income events coming up in retirement, that could be a timeframe where you want to do some Roth conversions and pay the taxes now. Because in those future years, if you have to do conversions, you have to pay a lot more in tax than you would currently right now. Also, if you have required minimum distributions or RMDs coming up, you're turning age 73, for example.

• 28:28Andrew Giancola?

  And you know those RMDs are coming up, that could be a time to pay taxes on some of that money. And or state income tax changes, like you're moving from state to state, that could be another reason. Let's say you're moving from Florida up to New York. If you were doing that and you're going to pay more taxes in the future, then you may want to do a conversion now to get some of those dollars out of that account. So when do these Roth conversions make sense? Well, first would be temporarily lower income years. So let's say, for example, you took a sabbatical and you decided, hey, I'm going to go travel around the world for six months out of this specific year, and I'm not going to make as much money in this given year. Well, that would be a great time to do a Roth conversion because you're going to be in a lower tax bracket. Or maybe your business income dipped in a given year, your business just didn't do as well in a specific year, but you know you got a lot of money coming.

• 29:12Andrew Giancola?

  Then next year, that'd be a great time to do a Roth conversion. Or maybe you're doing a job transition and you know that, you know, in the future, you you're getting some additional education and you're going to be making a lot more money with that job transition than now, maybe the time to do a Roth conversion. Or you're looking at doing early retirement and you are early retiree before social security kicks in. You want to make sure that you do this conversion and you don't want to impact that social security. That could be a great time or before RMDs like we talked about earlier. Now, another time to consider this is if you want to reduce your required minimum distributions. So if you want to make sure that the amount of RMDs that you have is lower, then you could do a Roth conversion. Another example is if the market declines. So this could be a timeframe where, let's say, for example, you have a traditional IRA that's worth a million dollars.

• 29:56Andrew Giancola?

  The market declined 20% and now it's worth $800,000. And you decide, actually, I want to do a Roth conversion now at this lower rate specifically. Because when the market rebounds, it will be inside of a Roth and I can reap the benefits of that tax-free growth. And so this is another cool way to take advantage of some of these Roth conversions when you do that. And so I really, really like this for a lot of folks to consider. When will Roth conversions? Not make sense. Well, number one is if you're already in a high tax bracket, or you expect substantially low income in retirement, those are two reasons to not do a Roth conversion. Or if you don't have cash available to pay the taxes, then that would be another reason. And if you're close to retirement and expect lower withdrawals, that's another reason to maybe not do Roth conversions.

• 30:40Andrew Giancola?

  You do not want to do these at the wrong time because it can be a huge, huge monetary impact on your bottom line. You want to make sure you're talking to a CPA. When you do Roth conversions, it's very, very important, or have a really good understanding of how they work, because I do not want you to do this the wrong way. And strategically, a CPA is going to help you tremendously when you do this. Number five is you want to check your capital gains exposure. So if you have a big gain in a portfolio, and you know that that is happening, you want to make sure that you are checking what your capital gains are every single year. So there are two types of capital gains. There are short-term capital gains, which are stocks that you have held for a year or less. That is going to be a much higher tax rate than the long-term capital gains. So your short-term capital gains can be taxed as high as 37%.

• 31:24Andrew Giancola?

  And they are taxed at your ordinary income rate, which is the same as your wage income. Whereas long-term capital gains has this preferential treatment, where you're going to either be 0%, 15%, or 20%, and this is all dependent on your taxable income. So why would you want to review this? And when would you want to review this overall? You want to review any stocks or ETFs that you sold this year? You want to make sure that you are looking at mutual fund capital gains distributions, which we'll talk about in a second. You want to look at business sales, real estate sales, and crypto transactions. All of those are things that you definitely want to look at. Now, one big thing that happens is if you own mutual funds, many actively managed mutual funds will distribute capital gains at year-end, even if you didn't sell anything. What that means is that you may owe taxes,

• 32:07Andrew Giancola?

  even if the fund went down in that given year. Because mutual funds, at their core, they are buying and selling a lot, and you are going to have to pay taxes on those. One of the reasons why we like index funds over mutual funds is the tax benefits, and that is one of them right there, because some mutual funds can trigger some capital gains. Number six is to optimize your HSA strategy. So if you don't know what an HSA is, one of the most powerful tax advantage accounts that you have out there. In fact, it has triple tax advantages, meaning money goes in tax-free, it grows tax-free, and you can pull the money out tax-free as long as you have a qualified medical expense. Now, a couple of key caveats with an HSA is, one, you need to have a high deductible

• 32:49Andrew Giancola?

  health plan. If you do not have a high deductible health plan, you cannot take advantage of an HSA. Two is if you are going to use the HSA to its tax advantages, you need to make sure that you have the system in place and know how to do this. So here's how this works. You contribute money to the HSA, and your goal is to get those dollars invested. My favorite place to open an HSA is Fidelity because it has the best investment options and it has the lowest fees. So Fidelity is by far my favorite right now as a place to open an HSA. Your employer may have an HSA option, and if they do, you need to look at the fees and you need to look at the investment options. Those are the two keys overall. But getting money into your HSA is very powerful because a couple of things. One is you can withdraw money anytime completely tax-free. So your money can be invested, it can grow, and you can withdraw it tax-free as long as you have this qualified medical expense.

• 33:34Andrew Giancola?

  What is a qualified medical expense? That means you are saving receipts for every single medical expense that you have, and you can even utilize receipts for a lot of other fitness items now. There's a lot of other personal care items that you can utilize with an HSA. And if you save all these receipts, there is no IRS limit as to when they had to happen. So you could break your leg at the age of 23 and reimburse yourself at the age of 55 for those medical receipts. And so because of this, you can build up a nice fund of tax-free money just from using the HSA. Now, let's say you overfund your HSA and you have too much money in there. Well, by the time you turn age 65, the HSA just turns into basically a traditional IRA. It's very similar to the rules

• 34:19Andrew Giancola?

  around the traditional IRA, which is why it is such a powerful account. Now, what I do with an HSA is I have a system in place. So we have a spreadsheet called the HSA spreadsheet, which we will link up down below in the show notes, which helps you just track your receipts. And you can track your receipts throughout the entire year if you want access to that. Then I just throw all the receipts in a Google Drive so that I have them in place, and I just number them Every single year, it is a really quick process and just allows me to stay on top of it. The reason why I have the spreadsheet, though, is I like to know the total amount that I have available to me in receipts. And so that is a really, really cool way. Now, there is a new AI-powered HSA receipt tracker that I just saw come out recently that we will link up on the show notes below, too, if you want to check that out.

• 35:00Andrew Giancola?

  It is absolutely free right now and looks like another cool option if you are looking for a way to track your receipts. It is something I am going to be testing out over the course of the next couple of weeks, and I can report back on how that goes. Now, number seven is to review and optimize your charitable giving strategy. So if you are someone who gives to charity, or you want to give to more causes that you believe in, then I'm going to show you the steps on how to think about this because you can do some really, really cool stuff with charitable giving that can help reduce your overall tax rate. So step one is you need to understand the standard deduction threshold. So for single filers in 2026, it is going to be $15,300. And for married filing jointly, it is going to be $30,600.

• 35:41Andrew Giancola?

  So if your total itemized deductions are not as much as the standard deduction, then you're just going to go out and take that standard deduction. Let me give an example here. Let's say you have a couple itemized deductions and they add up to $20,000. Maybe you give it to charity, you have some daycare deductions, some other things, and so all of those things add up and it's $20,000. Well, you would most likely take the standard deduction instead because that would be $30,600 that you could reduce your overall tax rate instead of having to reduce it by that $20,000. All right, number two is you can consider to bunch donations. So if you give consistently each year but never exceed the standard deduction, you may benefit from bunching. So instead of giving $10,000 per year for three years,

• 36:22Andrew Giancola?

  you can give $30,000 in one given year, and that is going to take you over that standard deduction. So maybe you put it aside into something like a high-yield savings account, or you put it aside somewhere else, and then you get the standard deduction every year. And then three years later, then you can take and bunch that giving and make sure that it goes all in one spot. But number three is you can use something called donor-advised funds. Now, if you've never heard of donor-advised funds, we are going to probably do an entire episode on these because there's a lot to talk about when it comes to donor-advised funds. But basically, what you Is you make a large charitable contribution in one given tax year. Then you take the full deduction immediately in that given year. And you distribute the funds to charities over multiple future years.

• 37:04Andrew Giancola?

  And so in a donor advised fund, you can do this for a number of different things. But it separates the tax deduction from the actual giving timeline, which is what I really like about this. So this is especially helpful in really high income years. Years where you have big business sales, for example, and you want to give to charity. Years with large capital gains and you want to reduce your overall taxable events. Or your bonus heavy compensation years. And so you can use a donor advised fund to do that. There are tools out there like DAFI that make this very easy. That can help you open a donor advised fund. You can also donate appreciated investments instead of cash. So let's say you had a really good year in the stock market. And you have all these appreciated investments and you know, you're going to have to pay a ton of money in taxes on that.

• 37:46Andrew Giancola?

  You can actually donate those appreciated investments instead of donating cash throughout the entire year. Which is going to help you reduce your overall tax rate. So if you bought a stock for $10,000 and now it's worth $40,000. If you sell it, you're going to owe capital gains tax on $30,000. But if you donate it directly, you can avoid that tax if you are already going to donate the money anyway. So that is another one that you can look at and see if you want to do that. Number five is understand the AGI deduction limits. So charitable contributions are based on your adjusted gross income. So cash donations to public charities, for example, are deductible up to 60% of your AGI. And appreciated assets are typically limited to 30% of your AGI. So you need to understand how that works when you do this.

• 38:30Andrew Giancola?

  Now step six is you can also look for qualified charitable distributions after the age of 70 and a half. Now, if you're over the age of 70 and a half, you can make a qualified charitable distribution directly from your IRA. So up to $100,000 per year can come directly from your IRA to charity. And this distribution counts toward your RMD. So if you are required to take RMDs out of your IRA, for example, you can donate a portion of that money as well. After the age of 70 and a half, so that you do not have to. If you were going to give to those causes you believe in anyways. Another great way to look at this. So here are some strategic questions to ask yourself, and you can screenshot this if you want to, to make sure you are looking at this. Am I exceeding the standard deduction? If you are, then charitable contributions could be a

• 39:13Andrew Giancola?

  great tax strategy for you. Should you bunch those deductions if you are not exceeding the standard deduction? That's number two. Do you have appreciated assets that you can donate instead of cash? Is that going to be better off for you? And are you in a higher than normal income year? If you are, this can help reduce some of the taxes that you pay that given year. And are you eligible for qualified charitable distributions or QCDs? That is the next one. And then, should I fund a donor advised fund this year? And again, we're going to do an entire episode on donor advised funds because they are really fantastic.

• 39:46Andrew Giancola?

  Now, number eight is to review your business deductions. So business deductions are going to be the fastest way to reduce your overall tax rate for those of you who have an LLC or are business owners. If you have a side hustle, you own real estate. If you are someone who owns a business, you should have an LLC and you should have business deductions. And the way that you should set this up is going to be having your business checking account, which is only business transactions, having your business credit card, which is only business transactions, and making sure it's paid off every single month, having your business savings where it's only business transactions, do not start to commingle personal and business together. But there are tons of deductions that you can take if you have a business. Things like software subscriptions,

• 40:27Andrew Giancola?

  office supplies, professional services like your CPA or an attorney, business insurance, advertising and marketing, website ads and leads, continuing education. But there are other tax breaks that you can do and tax strategies, things like the home office deduction. So you can deduct your entire home office and check out the square footage. You put it in that calculation and the IRS calculates that. The simplified method is $5 per square foot, up to 300 square feet. But if you work in a couple of different areas in your house, you can do your home office deduction in a couple of those different areas. Step three is if you drive a lot for work, make sure you're getting your miles. You can download the app like Mile IQ. If you use QuickBooks, QuickBooks now has a way for you to track those mileages as well, because you can deduct things like gas.

• 41:12Andrew Giancola?

  You can deduct things like insurance, repairs, depreciation. So if you're driving a lot for your business or your LLC, that is another thing that you can do. Number four is looking at depreciation or Section 179. Large purchases may not need to be deducted slowly over years. You may be able to expense them immediately. And Section 179 deduction allows you to do that. So talk to your CPA about that. But this is about buying equipment or purchasing computers or outfitting an office or even buying certain business vehicles. All of these may be able to be depreciated over that timeframe. Step five is retirement contributions to the business. So any retirement contributions to the business you can deduct. Or if you have health insurance to the business, you can deduct stuff like that as well. So any of that stuff is a big deal. Step six is you need to look at your estimated quarterly payments. So business owners do not have money taken out of their checks like your W-2.

• 41:57Andrew Giancola?

  You've got to make sure that you're making your quarterly payments. And so typically I look at this every single year with my CPA. We figure out exactly how much we're going to pay and we adjust it throughout the year if we think the year is going to do better. Also, doing an entity structural review. Should you be an LLC? Should you be an S corp? Should you be a C corp? Making sure you're reviewing that with your CPA. When I moved to an S corp originally years ago, it made a huge difference in my taxes. And so looking at the way that you're going to be structured can be really, really important. Also doing your documentation audit and confirming that your receipts are saved, confirming that your logs are documented, confirming everything is on hand is really, really important. But those of you who have a business, the bottom line is that you have so many different deductions available to you. Things like the Augusta Rule where you can rent your house back to your business

• 42:42Andrew Giancola?

  and save a ton of money there. There's so many different things that you can do when it comes to tax strategy. So it's very important to have a good CPA in your corner who also understands tax strategy. That is the overall thing that you are looking for when you're interviewing your CPA. Now, number nine is to revisit 529 plans and education tax benefits. So if you have kids and you want to save for their college, you need to revisit 529 plans and understand how a 529 plan works because this can help you with your taxes as well and can be a huge benefit to you. And so if you want to save for your kids' college, a 529 plan can help you because contributions are made with after-tax dollars. Investments grow tax-free. And then when you pull the money out, it is tax-free as long as You use it for qualified education expenses. So things like tuition, books, all those different things.

• 43:27Andrew Giancola?

  But you can also use this now for trade school, K through 12. There's a lot more benefits there. So if you know your kid's going to go to private school or anything like that, a 529 plan could be beneficial for you. While there is no federal deductions for 529 contributions, there could be some state deductions. So each state has different rules for the annual deduction limit and all those different areas. So you got to look at your state specifically to see what is happening there. Now also, you want to look at some education credits. Do you have education credits that are available to you? There are things like the American Opportunity Tax Credit. This is worth up to $2,500 per eligible student per year. It applies to the first four years of higher education and it phases out at higher income levels. So if you do have a high income, this will get phased out. Or there's the Lifetime Learning Credit, which is worth up to $2,000 per tax return and can apply to undergraduate,

• 44:12Andrew Giancola?

  graduate and continuing education. Now, this is also subject to income phase outs and is not refundable. So there are a lot of things that you can look for here when it comes to some education credits. Now, some newer 529 considerations is up to 10,000 per year, can be used for K through 12 tuition and federal and state rules are still going to apply. And funds may be used towards qualified apprenticeship programs. The flexibility of a 529 is getting better and better. And again, if your kids do not go to college or they do not use the 529 plan, at the end of that timeframe, as long as you've had this open for a specific period of time, you can roll that money into a custodial Roth IRA. So there is an exit plan for that, those dollars. So you do not have to pay the penalty if you are looking for this.

• 44:55Andrew Giancola?

  Now, number 10, the last thing that you should do, especially if you have a CPA, is run a forward looking tax projection. So most people treat taxes as historical. They gather documents in March, they file them in April, and then they react. High earners and wealth builders, they treat taxes as a forecasting exercise. And so what I do is every single year, I do what we call a tax plan with my CPA, where we go through and figure out, okay, well, what are we going to do this year to make sure we reduce our overall taxable income? So that we do not get to the end of the year and panic that we do not have enough deductions in that given year. And so step one, I want you to estimate this Year's total income. Look at this year's total income from W2 income or business income,

• 45:36Andrew Giancola?

  investment income. Look at capital gains or rental income. Add it all up and tell yourself and write down how much you have in income throughout the given year. Number two is identify what your marginal tax bracket is. You should figure out what this number is and understand what this number is. If you're running it through TurboTax or TaxACT or some of these other tools that are out there, then you can absolutely figure out what this number is because they help you do that. If you have a CPA, just ask them what your marginal tax bracket is. But you can get this information pretty quickly from using a lot of those tools. Now, if you file manually, that is going to be a lot of math and calculations, and most of you most likely are not doing that. Number three, then ask yourself a number of these questions, okay? Should I increase my 401k contributions to reduce my overall tax rate? Should I fund or maximize

• 46:19Andrew Giancola?

  my HSA? Should I harvest losses? Should I convert to a Roth this year? Should I donate some money this year? Should I accelerate business purchases into this year? I know a lot of people that have done that over the course of last year, for example. And should I delay income into January if I made too much this year? Step four is then adjust your withholding. So, once you figure all this stuff out, you can adjust that withholding with Form W4, and you can make an additional estimated tax payment if you need to and/or adjust your Q4 quarterly payment. So, if you're W2, adjust your W4 withholding. If you are a business owner, adjust your quarterly tax payment and adjust your Q4 quarterly payment as well. Step five is I want you to plan for next year and not just this year. So, will your income increase next year? Are you going to make more money? Are you going to get a bonus? Is your business going to grow? Those types of things.

• 47:04Andrew Giancola?

  And when will your social security begin? If you're getting close to retirement age, this is another consideration that you want to make sure that you have. But every single year, you need to make sure that you're projecting and planning for the next year. This is what real wealth builders do, is they think about taxes and ways to reduce those taxes overall. So, let me know down in the comments below. I want to hear from you. What are some of the things that you're going to do this year to reduce your overall tax rate? How are you going to do that? How are you going to make sure that you reduce your taxes? I want to hear from each and every single one of you. Now, if any of you are looking to learn more about how to reduce your taxes, learning about how to get a step-by-step financial plan, and learning how to reduce your stress and anxiety around money, Making sure that you know that you have a plan in place of what to do with every single dollar, then I highly encourage you to join us in Master Money Academy.

• 47:49Andrew Giancola?

  Master Money Academy is the place to help you with a step-by-step financial plan. I am so proud of what we've been doing in Master Money Academy and the feedback has been absolutely amazing. So I really want to invite each and every single one of you to join us inside Master Money Academy. You shouldn't be stressed about money. You should feel hope. You should have an understanding that you know what your financial future is going to look like. You know that you're going to be able to retire one day. You know that you're going to be able to do this. You can do this. You can get your finances together. You could be the first person in your family to build wealth, to grow your family tree, to actually be the first person to retire in your family comfortably. And Master Money Academy teaches you how to get there. And so I'm really, really excited for all of our members there. We are doing some really cool stuff. And again, if you get stuck during any step whatsoever, I do live coaching calls every

• 48:34Andrew Giancola?

  single week where I answer all of your questions and really get to know each and every single one of you. So I can't wait to see you inside Master Money Academy. We're going to link it up down below in the show notes and I am going to give podcast listeners a special trial down below. And so I want you to check that out. It's for podcast listeners only. Again, thank you so much for being here and listening to this podcast episode. I truly appreciate each and every single one of you and we'll see you on the next episode.

• 48:58Speaker 02

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