The Dr. Friday Radio Show

Dr. Friday Burke

The Dr. Friday Radio Show is a weekly radio show broadcast live on 99.7/WWTN every Saturday from 2PM-3PM CST. If you are outside of the listening area of the radio station (Nashville, TN), you can also download the iHeart App on your smartphone and search WWTN to hear the LIVE show. You can also listen to past episodes on the Dr. Friday Tax and Financial Firm website (https://drfriday.com), on Apple Podcasts, Google Play and many more.

  1. Jun 16

    Dr. Friday Radio Show – June 13, 2026

    Dr. Friday uses this final live radio broadcast to focus on tax planning before major life events, especially selling property, inheriting real estate, transferring family homes, and updating estate documents. She explains why basis, appraisals, trusts, POD designations, and powers of attorney matter before a family is forced to sort things out after the fact. The episode also includes caller questions on inherited property and prize winnings, plus reminders about marketplace insurance, Medicare IRMA, IRS identity checks, and business recordkeeping. Summary Points Home sale basis: Dr. Friday reviews the primary residence exclusion, explains that the old rollover rule is gone, and reminds homeowners to document major improvements that increase basis. Inherited property: She explains step-up in basis, why the date-of-death value matters, and why appraisals can be stronger support than rough comparable sales after repairs are made. Final live radio show: Dr. Friday tells listeners the show is moving off 99.7 and toward DrFriday.com, where she plans to keep answering questions and sharing tax education. Family property transfers: A caller asks about homes titled in her parents’ names, a long-running purchase arrangement, quitclaiming property, and how inherited homes differ from property she has been buying. Estate documents and gifting: The episode covers trusts, wills, POD designations, powers of attorney, probate risk, and situations where beneficiaries used gifts after taxes to honor a parent’s wishes. Prize taxes and records: Dr. Friday discusses lottery withholding, St. Jude home raffle tax questions, 1095-A marketplace repayment surprises, Medicare IRMA, IRS identity checks, mileage logs, receipts, and home-office rules. Episode FAQ Q: Do I owe capital gains tax just because I inherit real estate? A: Dr. Friday explains that inherited property generally receives a stepped-up basis, so capital gains usually become an issue when it is sold for more than its date-of-death value. Q: Do repairs after inheriting a home increase the inherited value? A: She says the inherited value is based on the condition and value at death, so later improvements should be tracked separately and the original value should be well documented. Q: Why should estate documents and POD designations be updated? A: Dr. Friday explains that courts and financial institutions follow the paperwork, so outdated documents can leave beneficiaries trying to fix things later with gifts and tax filings. Transcript 00:01 No, no, no. She’s not a medical doctor, but she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Doctor Friday show. If you have a question, Question for Dr. Friday, call her now. 737-WWTN. That’s 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. Dr. Friday and the doctor is in the house. We are here today to take calls talking about taxes, talking about maybe making some planning. You know, taxes are great, but normally we’re doing taxes after everything’s already happened. So if you’re really thinking about taxes, you’re probably thinking about 2026. You need to put some plans into play to say, how am I going to pay less in taxes? Can I pay less? Is it better to pay more today and pay less later? If I sell this, if I inherit this, if I convert this, will any or all of these be good or bad things? Again, I don’t really have the perfect answer for you because I don’t know what you’re going to buy, sell, or trade. But if those are things that you’re thinking about, then those are the kinds of things you do need. 01:18 to make sure that you’re accounting for. I’ve had more than one person come in and they have sold their primary home or they’ve sold a piece of real estate Or even inherited property. And they’re like, well, I I shouldn’t owe any taxes, but you know, just because you people tell you you don’t owe taxes doesn’t always mean you don’t owe taxes. So, I mean, you can sell your primary home, but if you sell it for $800,000, you purchased it for $200,000 and you’re a single individual. There is a one-time exclusion of 250,000. Well, 200 plus 250 does not equal 800,000 So you would end up with a capital gain situation. And for any of you are sitting there thinking, but wait, as long as I spend the money within the next two years or put the money back into another piece of real estate, I don’t have to pay the taxes. That tax law died a long time ago. That was something that was actually back in the early 2000s that has not been in existence for a long time. Tax law now is if you sell your primary home You can take your original cost basis and that would include the land and some people built their own homes. And then any major improvements that would have increased the value of the home. 02:36 For example, an extension, or if you’re on piece of property and you built some barns or um or you gutted the kitchen so you purchased the house back in the 80s and and then you redid the kitchen um now that would be a better upgrade so therefore the house would be worth more money so Those are the kinds of things. So also for all of you that are listening, you might want to think about if you’re actually living in a house that you own or purchasing along with the bank for most of us. You might want to document those things, right? Because I have people that’s lived in their homes for 20, 30 years. And let’s be on it. You’re not going to remember everything you’ve ever done to increase the value of your property. You fenced in the properties, you put in a swimming pool, you You know, you you did different things. You took a gravel driveway and now it’s an asphalt driveway. When you purchased it was gravel, now it’s asphalt. That increases the value of the home. So these are the kinds of things you need to document as well. Now, as long as you’re living and that’s what you’re doing as far as selling your property, that’s fine. Now, if you pass away and you leave that real estate. to um whoever your beneficiaries are, they’re going to get what’s called a step up in basis. But one of the things I’ve noticed lately is A number of clients, they inherit the property. 03:56 And keep in mind, it’s what the value of the property was at the time of inheritance, is what your value is. Not after you’ve put $50,000 into that home and increased the value by another $150,000. Because when mom was living in the house, for example, um, she was older, she wasn’t able to maintain the property the way it should be. A lot of things went bad or got old or even, you know, had holes in the floor and bad doors and all those things. And you said, hey, you know what, if we go through and we put a little money in this house, we could get a lot more money out. Great idea. But keep in mind, the value of the home was not the value after you improved it after the passing of that individual. The value that you get of the home was before that happened. So this is one of the big things the IRS has really come down on is a lot of times people are taking comps, but the problem is the IRS is finding that many of the homes when people have lived in them for 30 years have not been maintained like the other comps you’re pulling. So it’s very important to really start getting into appraisal so that the appraisal that comes in you can justify your basis, not just a comp. 05:14 Now, if there’s somebody that you know that can do a uh appraisal based on, you know, the roof is 30 years old, the house is fifty years old, uh, you know, all these different things that come into play because a lot of times people will say, well, I matched it up to another three-bedroom, five bath that’s sold right around the time of the passing And it’s roughly the same square footage. But was it built at the same time? Was it actually had the same kind of maintenance? Because again, as people get older, it is something that, you know, that the house can get away from them So, um, if you are an individual that is uh going to inherit or have inherited um a property It’s a great idea, don’t get me wrong, fix it up and then sell it and put the money, you know, double your investment, which many times can be done with some really decent improvements But um otherwise sell the property before you fix it up and then you don’t have to worry about capital gains. That’s your two options. But uh don’t fix it up and think that Al after you fix it up, now you get 100% tax write-off Because the tax law is coming back and saying, nope, we found out a lot of people are trying to do this. And so they are, you know watching and looking. 06:26 And again, when we file our taxes, it’s not like we want to sit there and say, what can we get away with? We want to file taxes that we can put to bed And that, especially if it’s a an estate tax return, because as a beneficiary or the executor especially, you have legal obligations to make sure the information is to the best of your ability correct But either way, you want to make sure that all of that information is being put together and that it’s being documented and that you’re able to submit that along with everything else to the beneficiaries so that they know how much money they’re going to end up being taxed because everyone always thinks all inheritance is zero, which a good chunk is, which is really nice. If you think about the step up and basis you get, that is about one of the best tax laws that’s on the books right now. Um versus, you know, like an IRA that you inherit and then you only have 10 years to basically empty it. Um, and that’s that’s not an easy thing to do. There are some games people will play, part of it going into charity, charitable remaining trust, different things like that where you can um donate a big chunk of it, but it doesn

    47 min
  2. Jun 9

    Dr. Friday Radio Show – June 6, 2026

    Dr. Friday opens this episode with one more reminder that the Tennessee disaster-related June 8 deadline is about filing extensions, making payments, and avoiding avoidable penalties. She explains how missing or undocumented extensions can turn into failure-to-file problems, then walks through IRS notices, abatement, and why real human resolution still matters. Later, she covers gifting after estates or lottery wins, mortgage payoff choices, where retirees might park cash, extension filing questions, and home-office rules for young earners and W-2 employees. Summary Points June 8 disaster deadline: Dr. Friday reminds listeners in affected Tennessee counties to file, pay, or document an extension before the deadline, especially if they cannot finish the return. Extension documentation: She discusses Form 4868, certified or tracked mailing, federal disaster notation, and why e-filing an extension may not work after the normal April deadline. IRS notices and abatement: The episode covers missing-return letters, first-time abatement limits, duplicate 1099-S home-sale reporting, and the frustration of trying to resolve clear IRS matching errors. Estate and lottery gifting: Dr. Friday explains why taxes should be handled before gifting estate proceeds or lottery winnings, especially when withholding, Medicare IRMA, or other income can change the final bill. Mortgage and retirement cash planning: Caller topics include whether to pay off a low-rate mortgage, whether the mortgage interest is really helping on taxes, and how retirees might think about CDs, bonds, annuities, and liquidity. Business and home-office deductions: She touches on small farms, LLC or S-corp questions, young gamers or influencers earning money, and why W-2 employees generally cannot deduct a home office. Episode FAQ Q: If I missed the April 15 extension deadline but qualify for the disaster extension, what should I do? A: Dr. Friday says to mail Form 4868 with tracking and the federal disaster information by June 8 rather than assuming a late e-filed extension will work. Q: Should I give away lottery winnings or estate money before filing the tax return? A: She cautions against it because withholding or estimated payments may not cover the final tax, and Medicare IRMA or other income effects can also change the outcome. Q: Is it better to pay off a 4% mortgage or keep the money invested? A: Dr. Friday says the math may favor keeping a low-rate mortgage if safe returns are similar, but paying it off can still make sense for peace of mind. Transcript 00:00 She’ll cure your tax problems or your financial woes. She’s the how-to girl. It’s the Dr. Friday Show. If you have a question for Dr. Friday, call her now. 737-WWTN. 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. G’day, I’m Dr. Friday, and the doctor is in the house. Um, and it’s gonna be a an interesting show, I think. For one thing, Monday is our big deadline for anyone that may have been in the 23 counties, which is almost everything around us, Davidson, Rutherford, Murray, um, you know. um Hickman, all of them um are under this major disaster um deadline that extended first to May 22nd then on April 15th, they extend it to June 8th. So all of us need to make sure that they’re filed and paid and dealt with. Um, at least, you know, even if you haven’t filed your taxes, if you’ve made the payment so that your taxes are paid in full or as close as you can estimate, because sometimes I’ve got a number of clients that are still waiting for K1s So it’s not like we can complete all returns, but we have the ability to complete as many as we can or make payments by by Monday so that we keep all of our penalties down. 01:23 We don’t mind not paying the government, but if we have to pay them, we don’t want to pay them with penalties and interest. So I had an interesting situation this week. Um pretty much I find it interesting Interesting, everyone else may or may not. Um, I found that we had a situation where a tax player had it paid um that they they came back, the IRS came back and said, you haven’t filed your 2022 tax return. And we’re sitting there going, okay, um, we show we filed it. We, you know, made all the payments, everything was done. We even sent in the payment with the last, with the filing. And so we’re waiting to find out. But then we um During that same time, the taxpayers had some issues in the past. So not knowing that, we just tried to put a waiver in first-time abatement. It’s an easy waiver and it makes things easy. And then we got on the phone with the IRS and the lady turns around and says, Well, you’re not going to qualify for first-time abatement because you’ve already had abatements in the past. Now we’re talking $46,000 abatement we’re working on here. So this isn’t, you know, a petty cash situation. Um, and and it’s basically coming failure to file the tax return. And so we’re we’re working on that and we have documentation and we’re showing. 02:39 But it’s uh it’s gonna be interesting. And then in the last week or two, I’ve seen Several well probably about four people that have received a notice on 2014 or 2024, 2023, 2022, and says they have not filed those tax returns. returns yet they know they filed them. They even have proof because a lot of them are e-filed. Um but the government’s saying hey EFU filed, you’ve got to resend a copy of that tax return and you need to sign it So you can submit it. But what you have to make sure is is that A, that you show payment in full. This couple did pay everything in full by the uh due date. Question is um The the biggest question that we have to find out is was there an extension file? Because then they were filing late and there was no extension. Always file your extension is what I’m trying to say. So if you have not completed your taxes yet. and you have a situation where you may not be able to file them by Monday, make sure you have filed an extension. And to do that, you have to certify one in. You cannot e-file an extension at this point. The IRS basically looks at extension due date as April 15th. But because of the federal disaster we’re under, you will qualify. 03:58 for an extension, but you have to document it, right? So you need to make sure you send in a certified copy along with on the IRS website they have the federal disaster extension. So you can actually put in the federal disaster or FEMA number that you can use for for your extension. But it’s very important because if you have not filed and you You know, may not be able to. And I know sometimes people listening, you don’t file because you don’t have the money. And it’s not necessarily the best plan, but I get it. Sometimes, you know, you’re just thinking, what can I do to survive? And sometimes surviving is I’m not going to uh file. But Your best bet is always file an extension if you’re one of those individuals. So that gives you until October. And then take that time and try your best to file the paperwork, even if you cannot afford to pay it because then you don’t get hit with failure to file, right? Failure to file just means you didn’t do the documentation. Now if you didn’t file an extension and you filed it in October, that’s failure to file because there was no extension on file. These are the kinds of things you have to make sure. And no matter if you have a tax person or not, you need to make sure that those extensions have been filed. 05:14 We do a lot of tax returns in our office and we do our very best to make sure everybody that we had the year before have been extended and we do it pretty early for probably some tax offices may not do what we do Because of the fact that I’m always afraid I’m a small office. And if something happens to me during the months that taxes are needing to be done, Then my clients could be out for a period of time, or you know, I’m not able to get them done as fast or whatever. And that’s very important to me that they’re covered at least If they have an extension on filed, they’re not going to get hit failure to file. They could still get hit with failure to not make proper estimate takes me. They could still get hit with uh not making proper payments. But the failure to file would not happen because the extension was on in play, right? Unless you wait till after the due date. And then, well, there is no extension after October 15th, unless you’re under a federal disaster extension. It’s that simple. So you just need to make sure that right now, if it’s the weekend, and so if you have not filed um your taxes and you don’t know if an extension’s been filed and you can’t reach your tax person on the weekend and You don’t want to wait till Monday. 06:30 Pull up a 4868 right on the IRS website. Pull up the extension um information, put it right at the very top. 4868 is about the easiest form in the world to prepare. It’s got your name, your social security number, your address. Um, and then it’s got like how much money do you think you paid in, how much money do you think you owe? Um, but you know, if those numbers are zeros, that’s still accepted by the IRS. If you don’t know those numbers, you don’t have to fill them in So bottom line, file that form, go to the post office, use priority mail, or go to FedEx or go to wherever you want to go. Make sure you have tracking. That’s all I’m going to say on that subject Because tracking is so very important, especially in these kind of scenarios, because the government um pretty much assumes that we’re all guilty, that we’re we’re doing our best to And it’s probably because it’s no different than if you probably have a policeman that’s a friend of yours or anything and they see the world a little different. My sister’s uh daughter married a police officer. And uh he’s

    47 min
  3. May 25

    Dr. Friday Radio Show – May 23, 2026

    Dr. Friday opens this Memorial Day weekend episode with practical reminders about the June 8, 2026 Tennessee filing and payment deadline. She explains why extensions only move paperwork, not the need to estimate and pay taxes, then takes caller questions on inherited trust assets, a California home sale, insurance proceeds, commission withholding, ESOP shares, retirement distributions, and IRS notices. The episode stays focused on documentation, timing, and avoiding avoidable penalties. Summary Points June 8 tax deadline: Dr. Friday reviews the disaster-related extension and reminds listeners that payments and estimated taxes still need attention even when returns are extended. Estimated tax penalties: She explains why taxpayers can owe penalties even if the full balance is paid by the annual filing deadline, especially when quarterly payments were missed. Inheritance and trust questions: A caller asks about Tennessee inheritance tax, revocable trusts, IRAs, annuities, step-up in basis, and whether trust income should pass through on K-1s. Home sale and insurance proceeds: Caller topics include filing a California return after selling a parent’s home and whether excess insurance proceeds from storm damage are taxable. W-2 withholding and ESOP planning: Dr. Friday discusses commission checks, changing from self-employment to employee status, limited W-2 deductions, and tracking ESOP basis. Retirement and IRS letters: The show covers Social Security and RMD filing thresholds, retirement tax planning, IRS direct deposit issues, and paper audit letters requesting income documents. Episode FAQ Q: Does a tax extension mean I can wait until October to pay? A: No. Dr. Friday explains that an extension generally extends the paperwork, while taxes should still be estimated and paid by the applicable deadline. Q: Are insurance proceeds taxable if repairs cost less than the claim payment? A: In the caller’s situation, Dr. Friday says insurance money for property damage is generally not taxable income when it restores the property. Q: What should I do if the IRS sends a letter asking for W-2s or 1099s? A: Dr. Friday says to provide the requested documents and consider checking IRS transcripts so any mismatch can be found and corrected. Transcript Announcer 00:01 No, no, no, she’s not a medical doctor, but she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Doctor Friday Show. If you have a question for Dr. Friday, call her now. 737-WWTN. That’s 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. Dr. Friday 00:29 G’day, I’m Dr. Friday and the doctor is in the house and it has been a wild ride since uh the first of the year, I guess you would say, since you consider They initially extended because of the ice storm into May 22nd. Then on April 15th, they extended us out to June 8th Who knows what’s gonna happen in the next week? It makes my life exciting and and fun, but uh always difficult to stay on top of it. So For all of you that are wanting to make sure that you have made your April 15th payment on time, which means paying it by June 8th. then you should make sure that you have at least the payment made. I mean, if you filed an extension, most of us do, a lot of us will go out until October 15th. But keep in mind an extension only extends the paperwork. Sometimes we’re waiting for K1s. We need to make sure everything is right. We’re not wanting to rush through and complete a tax return just to get it done. Dr. Friday 01:25 But, you know, with that being said, you don’t want to turn around and then end up with um owing a dollar amount and paying it back in October, because if you pay it in October. Then you will have interest and penalties that you have to pay. Just that simple. So making sure that you have everything correct and you want to make sure that you’ve done what you need to do. Then, you know, at least get an estimate paid out there so that way you’re not in a situation where you don’t want to um uh end up with you know i owe ten thousand dollars and now it’s october and now you owe twelve thousand dollars or more depending on the penalties and if you made proper quarterlies and yes for anyone that’s listening There is a rule that says you need to make estimated tax payments if you actually owe more than $500 the year before. Now, that does not mean that everybody has to make them. You can make them through increasing your W-2 withholding. Dr. Friday 02:27 You can make it through if you’re older and you may be receiving um RMDs require minimum distributions. You can have them take out the extra payments. So that way you’re not having to make your estimated tax payment. And talking about estimated tax payments, your first estimate would be normally due April 15th. That would be now due 6. 8 or June 8th. Because of the federal disaster extension. So you had have one due on the 8th and the next one due on the 15th of June um to make them filed on time. Many people are getting, at least several of my clients have gotten letters saying that the IRS is um needing them to update their banking information because they have a refund and in many cases these individuals did not have refunds and they do now because Um, at least in in my situation, several of them had uh we had estimated penalties that um got waived because of the federal disaster in 2025. um and in 24. Dr. Friday 03:29 So some of them have them on one of the other. So again, paying your taxes on time could end up giving you a small refund, especially if you had estimated the tax software to charge a penalty or if you did not make proper estimated again estimates are mandated if you do not pay them properly you will end up with a situation where you have to pay a penalty, even though you paid it all by the April 15th deadline. Dr. Friday 03:55 I can’t really tell you after 30 plus years how many times I’ve had someone say, why are they charging me a penalty when I’ve already paid them all of the money why you know and sometimes it’s three four five eight thousand dollars because they paid it by april fifteenth but they did not make proper estimates Now, if this was a one-time sale that happened because you sold some real estate or something and you weren’t required to make estimates because of the situation Um, and you did pay it by April 15th, there may be a waiver, but in most cases they’re self-employed and they’re just paying all of the taxes at one time. All right, if you want to join the show, you can. 615-737-9986. It looks like we have David on the line, which is awesome. Hey, David, how can I help you? Caller 1 04:39 Uh yes, Dr. Friday. I just had a question about uh taxes, inheritance taxes on a revocable trust in Tennessee. Dr. Friday 04:48 Uh-huh. Caller 1 04:49 Is is there an inheritance tax on uh uh funds or cash on a revocable trust? Dr. Friday 04:59 Well, yes. I mean if it’s over, I believe it’s twelve million dollars or fifteen million, I’d have to look up the exact number. If the estate is over, uh Tennessee follows the federal tax law. So it would have to be higher than that to actually do something. But um if they haven’t, I mean if it’s just a normal estate where you inherited, then the only tax you would have to probably look after would be if it’s an IRA or an annuity. There may be taxable dollars involved in um in those funds and you’d have to pay tax on them. Caller 1 05:34 Okay. Would would that be just the tax on the income generated uh on that fund since the deceased Passed? Dr. Friday 05:45 Uh yes. Well in an IRA it would be tax on the entire thing because obviously it would be no different than if it was your own personal traditional IRA. On annuities, usually it’s only on growth, but I have had some people actually put the money in an IRA. I mean in an annuity from an IRA. So the same thing. It could be 100% taxable. It could just be taxable on growth, it really depends on the investment. If it’s stocks, there’s a step up in basis. So those would not be taxable Mainly I find the taxable falls into IRAs, 401ks, or annuities is where most of the taxable dollars without step ups. Caller 1 06:24 Okay. And and what is the difference between a tax rate on these amounts of thirty seven percent or just your normal tax rate, I think, on income for your bracket? What what do you think? Dr. Friday 06:40 37 is the highest tax bracket anyone pays. Okay, so that’s your highest bracket, um, ordinary income. If you if they file it through an irrevocable trust, which becomes revocable, I mean, um, it’s irrevocable that becomes irrevocable when they die. then then you you you can pay the tax through the trust, but the trust starts at twenty-four percent and works its way up to thirty-seven a lot faster than if you give a K1 from the estate and you file it on your own personal tax return. It really depends it’s that is up to the executor So um I’ve had more than one that says, no, I just want to pay the taxes because I don’t know if anyone will pay them and it’ll be just more headache, you know. Um, but normally it’s cheaper for all the beneficiaries if the taxes roll to the tax Players not through the estate. Caller 1 07:31 Gotcha. Gotcha. Okay. Very good. Uh good. I think you’ve answered my questions there. Dr. Friday 07:37 Thank you for calling. I really appreciate it Caller 1 07:39 Thank you very much. Thanks. Dr. Friday 07:42 Bye. All right. We have Sean and Bellevue. Let’s see if Sean has something I can help him with. Hey babe, how can I help ya? Caller 2 07:48 Hey doctor, thanks for taking my call. Sure. So uh in at the end of twenty twenty two, uh went to California to move my handicapped mom out here to to live with me for me to take care of uh take care of her. And she really didn’t have

    47 min
  4. Apr 28

    Dr. Friday Radio Show – April 25, 2026

    Dr. Friday uses this episode to step back from the rush of tax season and look at what taxpayers can still control after the Tennessee filing extensions. She covers retirement contribution timing, business-loss documentation, estate and trust tax handling, and why good records matter when the IRS asks questions. A caller also asks how to distribute an IRA that was paid into an estate trust, leading to a practical discussion of Form 1041 and K-1 reporting. Summary Points Tennessee filing extension: Dr. Friday notes that Tennessee taxpayers now have until June 8 and discusses remaining opportunities for certain 2025 contributions. Retirement and withholding planning: She compares traditional retirement contributions, Roth choices, capital gains, Social Security taxation, and the impact of under-withholding. Business versus hobby losses: The show reviews startup education costs, repeated Schedule C losses, short-term rental use, and the need to prove a profit motive. Estate IRA distribution question: A caller asks about an IRA portion paid to an estate trust, and Dr. Friday explains using a 1041 return and K-1s for the beneficiaries. Entity structure decisions: Dr. Friday compares LLC and S corporation tax treatment, payroll, self-employment tax, and Tennessee franchise excise considerations. IRS problem resolution and basis records: She discusses payment-plan problems, Taxpayer Advocate help, amended returns, and appraisals for inherited homes. Episode FAQ Q: Can I deduct business classes before the business is actually making or trying to make income? A: Dr. Friday says not automatically. The taxpayer needs to show a real attempt to operate a business and make money, not just take courses. Q: How should an IRA paid into an estate trust be distributed to beneficiaries? A: In the caller’s situation, Dr. Friday discusses filing a 1041 trust return and issuing K-1s so each beneficiary reports their share. Q: Why does Dr. Friday recommend appraisals for inherited homes? A: She says an appraisal helps document basis at the date of death, especially if the property is sold later or multiple heirs are involved. Transcript Announcer 00:01 No, no, no, she’s not a medical doctor, but she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Doctor Friday Show. If you have a question for Dr. Friday, call her now. 737-WWTN. That’s 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. Dr. Friday 00:29 G’day, I’m Dr. Friday, and the doctor is in the house. Have we had some busy times lately with the whole Extension on taxes and then a second extension on taxes. So right now it’s June 8th that we have to have everything filed by um in Tennessee. They did all 96 counties. So um We uh obviously are are working on taxes. Not this weekend, thank goodness. So we get a little break. Normally it’s uh been crazy for a while here, but We are moving forward. And then if you’ve got additional questions or you want to join the show, you can at 615 737-9986. It’s actually a really nice Saturday out there. Everyone’s heading some time to uh start working, but we are just about done. with the month of April, which means that we should be seriously considering not only we can’t change a whole bunch that happened in 2025. Dr. Friday 01:30 Sure, if you are a self-employed person, you can have a self-employed Except that you don’t fund until as long as as October. Um and for some people, if you did not and you wanted to fund your HSA or your IRA for 2025. And even though we are past the April 15th deadline due to the federal extension, we would be able to still contribute the proper amounts into those accounts depending on your age and your income if they applied. So so there is a little bit of a window for some people that may find out that they owe money and they One way to reduce the amount you owe the IRS is putting it into a deferred account. I would always suggest talking to a financial planner, uh, tax people. We’re always looking at instant gratification, meaning if I’m going to save money today by giving it to a retirement plan versus to the IRS, guess what? Dr. Friday 02:24 I would say it’s usually a good idea, but then I have told people sometimes it’s better to do the Roth because you’re in the 12%, even though you might owe the IRS. You’re only saving eight or nine percent if you put it into your retirement now. Um, if you put it into the Roth, then you know it will grow tax free. And even though right now you may still owe the IRS it will be a better investment. But again, I’m looking at tax situations. You should always double check whatever Unless your tax person happens to be wearing two hats, one as a financial advisor, one as a tax exput, then you should always check. Um just like if your financial, I had a case this year where the financial planner thought they had done the math correct and they had done uh some conversions and um and then of course I did the taxes and they were quite a bit off They um I I don’t know if they just didn’t have the right numbers to start with. Dr. Friday 03:24 I wasn’t there. So all I can say is the client wasn’t happy. They owed an additional $17,000 um because of Social Security being taxed more, different things came into play. And it may have been that they didn’t know that they were going to have quite the capital gains that came in. A lot of times it’s a lot of little things. I had a another client that we just finished up last Friday, and um he’s like, why? Why do I owe money? I never owe money But they had overall had $60,000 more income because of capital gains, a larger distribution from retirement, which then made more of the Social Security. They were not at the 85% normally. So 85% of their Social Security became tax, a little bit more interest overall, and it all kind of trickled down. And most of the things that had um increase capital gain, social security, they were not having any kind of withholding. Dr. Friday 04:19 So it was um another case where they owed, it wasn’t horrific, it was like 3,900, but it was a lot when you don’t think about it, right? When you don’t normally owe the IRS. It’s quite a bit when you have to. So if you’re in the process of doing that kind of thing, you do need to make sure you’re tracking everything. Today’s show, I kind of wanted to touch on one of the couple things I’ve ran into this tax season. And maybe part of it is obviously a lot of you guys know I do um I now have a home farm. But also um small business owners. You have to have some reasonable concept. I mean I had a person that came in and They started a business and they um they they went and done a whole bunch of classes and took um took a a lot of courses uh from supposed experts in the field. Dr. Friday 05:16 I’m talking like up in the forty-five thousand dollars um of doing and um and then you know never generated any income from this business at this point at least. And um and she’s like, well I can write all this off because I was self-employed. And I’m like The tax law isn’t quite that simple. First, you have to be making the attempt to make money. You have to be able to show that you have done this because you’re able to make money. The IRS says, hey, if you’re going out and learning how to make pots and you’ve never made a pot, you’ve never sold a pot, you’ve never done anything, but you’re taking these courses When you do start selling your pottery, that would be part of your startup to learn how to do it. It would not be something you could write off. at the time of taking those courses and not not having anything to sell, any product, any classes, anything that shows that you actually took this um education and created a business that is now at least attempting to make income I mean, maybe you’ve got a full website and you can show that you put out a marketing uh plan and and that, I mean, it doesn’t mean you have to have shown that you made a profit. Dr. Friday 06:34 But keep in mind, the IRS does also say for uh small businesses or anyone that operates as a Schedule C, um, two out of five years, you need to have been making money So a lot of times the first year or two, we don’t expect to make money. You know what I mean? By the time you get all your startup costs and you learn how to make and get clients Sometimes the first year or two is a dry year or an upside down year, whatever you want to say. Then you go into the third year and and you’re you’re least breaking even. The fourth year you made a profit. And goodness gracious. The fifth year you’re actually paying back the first year’s losses. That’s the way the IRS sees it. If you’ve been at this for four, five, six years, and I’ve had a couple clients come in this year, and they’ve been taking losses I mean, you know, they forever is what they basically have said, but let’s just say for four or five years. Dr. Friday 07:25 At that point, I’m questioning, is this really a business? Is it a legitimate business? Is this something that’s a hobby? Um Something that uh another one is the a um the short-term rentals. Um if this property is a short-term rental and we put that on Schedule C so we can take the losses Um, if this is actually your vacation home and you are using it more than two weeks in a year. Keep in mind you cannot take all of those losses because it’s personal use. It is not just a business now. You’re using it or giving your family and your grown children and your grandchildren. Everyone has access to this home. That turns around and now you’ve got a situation where if you’re ever audited, they’re going to say, well, was the home available for rent for 365 days? And you may say, well, no, I had this week that we had to go down there for repairs and this, and we had another

    47 min
  5. Apr 14

    Dr. Friday Radio Show – April 11, 2026

    This episode stays focused on last-minute tax-season decisions, especially for Tennessee listeners affected by the IRS winter storm extension to May 22, 2026. Dr. Friday explains why filing still matters even when payment is difficult, and she answers caller questions on capital gains, missing forms, debt cancellation after a spouse’s death, inherited funds, and gift tax rules. She also shares practical reminders about quarterly payments, qualified charitable distributions, and setting up IRS online access before a problem shows up. Summary Points Tennessee disaster extension: Dr. Friday opens by reviewing the IRS relief for affected Tennessee counties and explains who still needs to file by April 15, 2026. Paying as you go matters: She stresses that filing late or skipping estimated payments can turn manageable tax bills into much larger balances once penalties and interest compound. Capital gains and payment plans: A caller asks about deferring brokerage-account capital gains, leading to a discussion of why stock sales generally are not deferred and why taxpayers should still file before requesting a payment plan. Common return follow-up issues: The show covers missing W-2 attachments, late-arriving 1099 forms, amended-return situations, and how IRS account errors can take a long time to fix. Death, inheritance, and canceled debt questions: Caller topics include a 1099-C issued under a deceased spouse’s Social Security number, inherited CD proceeds, and the documentation needed when stepped-up basis or donated property values are involved. Year-round planning ideas: She highlights bunching deductions, qualified charitable distributions after age 70 1/2, IRS PINs, and ID.me access as practical tools for avoiding future problems. Episode FAQ Q: Can brokerage-account capital gains usually be deferred? A: Not in the general way the caller described. Dr. Friday says stock sales usually trigger tax when sold, unlike certain real-estate deferral situations she mentions. Q: Should I amend a return over a very small missed 1099 amount? A: Her answer in this episode was generally no for a tiny amount that would not materially change the return, especially if the IRS can correct it on its own. Q: Do I owe tax on money inherited from a relative’s CD? A: Dr. Friday says the inherited principal itself is generally not taxable, though related interest may need separate tax treatment depending on how it was handled. Transcript Announcer 00:01 No, no, no, she’s not a medical doctor, but she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Doctor Friday show. If you have a question for Dr. Friday, call her now. 737-WWTN. That’s 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. Dr. Friday 00:30 G’day, I’m Dr. Friday, and the doctor is in the house on this absolutely gorgeous Saturday and the last one before the April 15th deadline. Let’s clarify for anyone again because I know there’s a lot of misconceptions back on April 3rd. You know how the government likes to keep us on our toes. They passed a um uh impact winter storm extension for everybody that lives in cheatham chester clay davidson decatur dixon harmon harden henderson Hickman, Lawrence, Lewis, Macon, Murray, McNair, Perry, Robertson, Rutherford, Sumpner, Trousdale, Wayne, Williamson, and Wilson. If you’re not sure, you can go right to the IRS website, take a look at the impact storm or the disaster extension for Tennessee, and they will have all of those out there for you because You have until May 22nd, which gives a couple of us a little bit of breathing room. Dr. Friday 01:35 Not everybody. Some people don’t fall into those counties and therefore. You are still required, people out in uh Knox County and things I do, and they will be filing as of the 15th. So this is the final um weekend before we get to do anything on that. But if you have any questions, you can join the show, 615 367, I’m sorry, 615-737-9986. 615-737-9986. You’d think I’d have that memorized by now. And if you want to have any questions, I know many of you are probably just out there enjoying this weekend, and maybe many of you have already filed your taxes There hasn’t been a huge change. I mean, many people over the age of 65, I will say, a large number of my clients. that do meet that criteria are getting some discount. If you have $150,000 or more in income as a married couple, you’re not getting 100%. Dr. Friday 02:39 If you have seventy-five thousand dollars or more as a single person, you’re not getting a hundred percent, but it does seem like we’re getting a little bit um in that little bit, especially if you’re in the 150 or or more income, you’re and you’re at the 22%. So if you save a thousand dollars, you’re saving two hundred and twenty dollars. which is more than they normally save. So it does help. But there is still that misconception out there that says that sales, I’m sorry, that Social Security is not taxed. It is taxed, people. It is taxed. It’s going to continue to stay taxed. There really isn’t something that we can do about that. It is going to the best that they did was give some sort of extension to individuals that are um you know older over the age of 65 to be able to get some break. But other than that, not so much a deal that’s going to happen. All right, we got the phone lines. That always makes me excited. Hey Robin Hendersonville, what can I do for you Oops, I lost him. Dr. Friday 03:42 I scared him away. All right, well Rob, if you want to come back on, you can. That was uh probably me jumping it before They had you ready. But anyway, so um it’s sales tax. We do have um some people are starting to add up their sales tax again and that’s good because we have $40,000 that you get for your salt tax which would include your sales tax state income tax in our case is sales tax And then your property taxes. And remember, some people have multiple properties and they only use them as a basic setup, right? So multiple properties, you can still write off the sales tax on those properties. Now, if you can’t itemize, you won’t get to do that. But if we’re looking for ways of maximizing, sometimes doing the um The deal where you are basically every other year maximizing your sales tax, every other year maximizing your charitable contributions um because you can’t really do much about mortgage interest, but you can on sales tax and things. Dr. Friday 04:42 So that way you have the ability to really do what you need to do to make it put more money in your pocket. So the only way to do that is sometimes every other year you can pay your property taxes in December instead of waiting till February. Um you can uh buy your larger purchases in that year as well. Maybe you’re thinking about buying a car or a boat or something that would be exceptional on that and we’ll be able to move from there and go into so Keep in mind there is still some ways and charity because if you’re gonna do charity and you maybe always put $5,000 a year, well if you can do it every other year and really maximize your charities in the years that you’re doing your property taxes and everything else, you’ll find that it is actually a really good idea because you may be able to itemize every other year versus not being able to itemize at all if you’re not playing the game. All right, if Rob is ready, we can try to go back to him. Hey Rob, are you there? Caller 05:41 I’m here. Can you hear me? Dr. Friday 05:42 I can hear you this time, my love. Thanks for calling back. What can we do for ya? Caller 05:47 I don’t know if it was last week on your show or if it was a commercial that you did. but it was referring to having to defer taxes on um capital gains through uh that you get through um like a brokerage account. It did I hear that correctly? Dr. Friday 06:06 I don’t think so. Um and hopefully I did not say that, because it’s possible, Rob, maybe you heard something, but uh I mean there is no way of being really deferring the tax because once it’s through a brokerage account, it’s It’s usually managed or you handle your own account, but once you’ve sold something, you can’t defer it. If that makes sense what I’m saying. Sorry. Caller 06:30 That’s okay. Answer my question. Dr. Friday 06:32 I’m glad you called. Thanks, Rob. I appreciate it. The only kind of uh deferrals on I’m trying to think really quick. We can let him go. I’m just trying to think if there you sometimes you can take losses against gains, but that’s not really a deferral. Um but You know, there really isn’t a lot of ways of deferring capital gains that I can think of. But I’ll I will try to go back and listen to my Uh he might have been talking about my one minute moments that are out there and see if we can’t figure out um which one that was during one of the breaks just to see if I can come up with a better answer than no. Never really liked that answer in my life. So I’ll I’ll see Rob if I can come up and if I can I’ll I will uh bring it back on in a during the next break. But um anyway, so we’re talking about anyone that doesn’t live in the counties that are extended, you need to file. Um if you can’t afford to pay, um You you can still file and then make a payment plan. Dr. Friday 07:33 Sometimes I have people that says, well, I didn’t file a tax return because I didn’t I was afraid to file because I didn’t want to um in a sense have the IRS trying to collect. But you know, the IRS in many cases will actually prepare taxes on behalf of that person, and they’re never going to be as good as what you have Prepared yourself most likely unless you have absolutely no deductions because they’re going to claim you single and zero, even if you’re married with children And they’re going to do the standard deduction, even if you

    47 min
  6. Apr 6

    Dr. Friday Radio Show – April 4, 2026

    This episode opens with timely news for Tennessee taxpayers in counties affected by the recent ice storm: the IRS has extended certain filing and payment deadlines to May 22, 2026. Dr. Friday also fields caller questions about when Social Security income triggers a filing requirement and whether people living only on benefits need to notify the government each year. Along the way, she covers inherited-home appraisals, donation documentation, IRS identity-verification letters, and the long-term cost of mishandling payroll taxes or S-corp wages. Summary Points IRS disaster extension: Dr. Friday says taxpayers in the covered Tennessee counties may have certain filing and payment deadlines pushed to May 22, 2026, with eligibility tied to the address on the return. Social Security filing thresholds: A caller example showed that when most income is Social Security and the remaining income is low enough, a federal return may not be required under the provisional income rules she discussed. Inherited home sales: Selling inherited property can still create capital gains above the stepped-up basis, which is why she stresses getting a real appraisal at the date of inheritance. Donation records and sales tax: Non-cash charitable donations need stronger substantiation than a rough estimate, and detailed Tennessee sales tax receipts can add up for taxpayers who itemize. Identity letters and refunds: She warns that IRS identity-verification letters can be legitimate and says some taxpayers may need to use ID.me and direct deposit details before a refund is released. Extensions, payroll taxes, and S-corp pay: Filing an extension can reduce the failure-to-file problem, but payroll taxes should be paid promptly and artificially low S-corp wages can reduce future Social Security and retirement contribution room. Episode FAQ Q: Who gets the May 22, 2026 IRS extension discussed in this episode? A: Dr. Friday says the relief applies based on the return address for taxpayers in the covered Tennessee disaster counties, with certain filing and payment deadlines moved to May 22, 2026. Q: If my income is only Social Security, do I usually need to file a federal return? A: As discussed on the show, Social Security by itself is generally not taxed; filing becomes an issue when enough other income pushes provisional income over the threshold she described. Q: Why does she stress appraisals for inherited homes and major donations? A: Because the appraisal helps support basis or value if the IRS later questions the number used on the return. Transcript Announcer 00:01 No no no, she’s not a medical doctor, but she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Doctor Friday Show. If you have a question for Dr. Friday, call her now. 737-WWTN. That’s 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. Dr. Friday 00:30 All right, Dr. Friday is here. We’re live in studio. We’ve got some great news for at least many of us that are in Williamson, Davidson, Robertson, Wilson, um counties, Murray counties. The IRS has at the last minute again yesterday on 4-3, they passed an extension due to the ice storm till May 22nd. So um it does say that it is anyone anyone in those addresses that will be in those areas and we can cover all of the counties here. Dr. Friday 01:02 It’s gonna be Cheatham, Chester, Clay, Davidson, Decatur, Dixon, Hardy. Hardman, sorry, Harden, Henderson, Hickman, uh Hendersonville, Lawson, Lewis, Macon, Murray, McNair, Perry, Robertson, Robert, uh, Rutherford, Sumpner Charlesdale, Wayne, Rob uh Williamson and Wilson. And I know that’s a lot to take in. And you can go to the IRS website, irs.gov, look it up under impacted by winter storm in Tennessee, ice storm uh that will affect us in January. Dr. Friday 01:37 So I will uh go right to the phones. We got Adam in Antioch and see if we can get a question in here. Hey Adam. Caller 01:45 Oh that was quick, thank you. Let me give you a lot of things. Uh my total income thirty-one thousand four hundred. Well I have to file a federal income tax. Dr. Friday 02:02 Are you on social security? Caller 02:05 Yes ma’am. Dr. Friday 02:06 Um how much of that is social security that you just gave me? How much a month do you get from that? Caller 02:12 The total is twenty-nine four Dr. Friday 02:14 Okay. So out of the thirty-one four, twenty-nine four is Social Security? Caller 02:20 That’s correct. Dr. Friday 02:21 Then you do not need to file. Caller 02:24 Oh good newsweek. Dr. Friday 02:26 Wow, well thank you for that. Caller 02:29 Thank you, ma’am. Dr. Friday 02:31 Thanks, sweetheart. Uh It’s always nice not to have to file. Most of us will never have, but sometimes we get lucky enough here or there to have a at least a year or something that may come into that situation. So um There is some waivers back to the IRS’s um natural disaster that they’ve they’ve put here in uh federal disaster, I should say, for the state of Tennessee You can go again to www. tn. Dr. Friday 03:02 gov. You can look up the disaster, and that way you can make sure you’re in the right county. It is going to be based on the address that you file your tax return on. The IRS is going to be using that as a forum of who and who does not qualify. I did have someone contact me um this week because they were filing and I guess a penalty was coming up when she put in her estimated taxes for last year because she waited until 11. 3 Um and what you want to do is you want to put in um I have had only a couple of them because most of the people I have uh Dr. Friday 03:40 Made it, but my system, anyways, all you want to do is let them know that you were covered by the natural disaster. And you can actually look up a disaster code on the IRS website for the disaster that you’re you’re covered under. And then that way you can include that. So that way your address should automatically correct 2025 if there is said penalty and also now Another one for um I should say 2024, which made it all the way in, and then some of the 2025 estimated payments and things that were extended until 11. Dr. Friday 04:12 3, those will all be covered under your address. So as long as your address, well, the first one, the first disaster covered all, what, 93 counties or something. This one is only covering probably about 15 or 20. This the ones that were hard pit by the ice storm, which Most of my clients, Rutherford, Williamson, Davidson, Murray, those are the big, big ones, Mini and Wilson and Hendersonville, but they’re all listed there. So again, we have uh an ice storm extension Dr. Friday 04:43 And I can’t tell you guys how many people had asked, do you think the IRS is going to give us an extension? And I kept saying, I have no idea. And then uh and then they did it yesterday. So um extension is on the books, which gives some people a little bit extra breathing room. If uh if you’ve already filed, if you’ve already scheduled your payment, like I have for some of my clients, there’s no way of going backwards. I will let you know that. Had someone email me this morning saying, hey, I um if you haven’t filed my taxes, don’t file them. But I had filed them because they’re due, guys, in less than 10 days almost. Dr. Friday 05:16 So So for all of you that want to procrastinate, wait. Now many of us would file, I would suggest If you if this is all to do with the payment, that’s fine, but filing an extension if you plan to go past this window. If if for some reason I had a number of people listening to this right now. I’m sure there’s people that had eight, nine, even one client was 11 days without power or internet. um situation. So there was some that were very badly hit. Dr. Friday 05:48 Some of us only had hours of of something or or nothing at all. But um they’re t they’re including us in the entire um county. So All that are affected on that, you have an extension deadline applies to individuals, income tax, and payments normally due on or before January 22nd. of uh twenty sixth that will extend and as long as the payment had been made before February sixth. So some of this It’s funny, they just put this out yesterday, but their deadlines or their deposits are still saying that some of them needed to have done Dr. Friday 06:22 quarterlies and things. They’re going to give you a small waiver from January 22nd to February 6th. But if you still haven’t made those payments, there will be some penalties and interest involved. But I will try to keep this out there for everyone to know. A lot of my clients, I’m going to probably try to send out a mass email just so they can make sure that if it applies to them and they have a situation, um, it may be something that they can use to get, you know, hey, if you normally would have filed an extension and couldn’t pay and that’s a Dr. Friday 06:53 that you know remember guys an extension never ever extends the money that you can’t pay a lot of times people file extensions for many reasons and many reasons is because they don’t have all their tax forms They have K-1s usually that are delayed, so they don’t have the ability to file their own taxes. But payment is due on four equal payments and or with your extension on April 15th. Now this will extend those people to May 22nd, but um you know you’re not going to have until October 15th to make your payment without penalties and interest Dr. Friday 07:30 Just saying. It’s big news, but I just want to make sure everyone’s on the same page. All right. So if you want to join the show, you can. 615-737-9986-615. 737-9986 taking your calls, talking about my favorite subject. Um, met a lot of new people this uh this last week. I was uh pleasantly surprised. Uh we we really hadn’t taken on a lot

    47 min
  7. Mar 16

    Dr. Friday Radio Show – March 14, 2026

    With tax season in full swing and the March 17 deadline for multi-member LLCs and S-corporations just around the corner, Dr. Friday packed this episode with timely, practical guidance. From clarifying the real story on “no tax on tips and overtime” to walking callers through Social Security taxation, inherited assets, and IRS penalty rules, this show delivers answers when people need them most. Dr. Friday also made a compelling case for why estate planning — especially wills, trusts, and life insurance — matters at every age, not just for the wealthy. Summary Points Business filing deadlines: Single-member LLCs file as sole proprietors on April 15 and do not need to file a March 17 extension; multi-member LLCs and S-corps (1120-S / 1065) do. Tennessee business owners should also register with TNTAP.tn.gov ahead of the April 1 business license deadline. Tips, overtime, and Social Security taxation: Despite popular assumptions, tips and overtime may still be taxable depending on overall income. Social Security must be reported on every return, and only qualifies for the new $6,000 per-person deduction (for those 65+) when filing jointly or as a single filer below the income threshold — not when filing married separately. Estimated tax payments and penalties: To avoid underpayment penalties, taxpayers must pay at least 100% of prior-year liability (110% for higher earners) in four equal, on-time installments. The IRS offers a one-time penalty waiver (the “get-out-of-jail-free card”) but it’s a limited resource. IRS debt resolution options: Taxpayers who haven’t filed or can’t pay have several paths: payment plans, partial payment plans, or an offer in compromise — but the IRS considers all assets (home equity, retirement accounts, etc.) before accepting reduced settlements. Inherited assets and home sales: Property and artwork inherited at death receive a stepped-up basis to fair market value at the date of death, often eliminating capital gains. Homeowners selling a primary residence can exclude up to $500,000 of gain (married) without needing to reinvest the proceeds. IRS going paperless: The IRS is no longer mailing refund checks — taxpayers must provide banking information for direct deposit or risk having their refund held. Electronic payments are also increasingly required for balances due. Episode FAQ Q: I’m 79 and file married separately. Why don’t I get the $6,000 Social Security deduction? A: The new $6,000 per-person deduction for taxpayers 65 and older is not available to those who file married filing separately. Because the IRS can’t verify both spouses’ income on separate returns, the deduction is disallowed entirely for that filing status. Q: My father-in-law recently passed away and we sold his artwork for $70,000. Do we owe capital gains tax? A: Most likely not, or very little. Inherited property receives a “stepped-up” basis equal to its fair market value on the date of death. So unless the artwork appreciated significantly after he passed, any gain above that stepped-up value would be small — and the gain period would be short-term or long-term depending on how long the estate held it before selling. Q: I’m required to take a one-time lump sum from a deferred pension plan. Is there any way to spread out the tax hit? A: Possibly. Before signing anything, consult a financial planner — it may be possible to do a custodial (trustee-to-trustee) transfer to an IRA or another deferred account and then take withdrawals over time. A lump sum taken all at once will push you into a higher tax bracket and make up to 85% of your Social Security taxable, so it’s worth exploring every option first. Transcript Announcer 00:01 No, no, no, she’s not a medical doctor, but she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Doctor Friday show. A question for Dr. Friday, call her now. 737-WWTN. That’s 737-9986. So here’s your host, financial counselor, and tax consultant, Dr. Friday. Dr. Friday 00:29 G’day, I’m Dr. Friday, and the doctor is in the house. We are here live, so if you have some questions concerning maybe you’re working on your taxes. I do want to put a shout out for anyone that is a multi-member LLC or a sub-s corporation. Do remember that Monday is your tax day. So you should have filed an extension, just to make sure that everything is filed properly or file the return, whichever works for you. Either way, you need to make sure you’ve got it all filed so you don’t get hit with penalties. That’s the one thing we don’t like is penalties. Dr. Friday 01:00 So if you’ve got questions and you want to join the show, you can do that. 615-737-9986. I am going to say that we are working hard on a lot of taxes ourselves. Finding that tax documents, people are having some problems getting all their documents together. We’ve already had a change, I believe it was with Charles Schwab, where a second set of documents have been sent out after the first. Dr. Friday 01:30 As well as we have the issue with all the tips and mainly tips, I have to say, overtime. The definition of tips, especially on the self-employed Uber drivers — individuals that are reporting the information based on what they have. The biggest question is, if you’re reporting tips and you are an Uber driver or somebody that is getting tips through a 1099, make sure that those tips are reflected in the income side because a lot of people are just using what Uber is providing. But we all know that if some of the tips are cash that did not run through the Uber 1099, therefore you may be overstating the tips based on the income. So if you’re going to report all of your tips, you need to make sure that you’re also deducting those from the right amount. Dr. Friday 02:31 And remember, tips for a self-employed individual — you do still have to pay the self-employment tax. They just give you a deduction against ordinary income tax. So the savings is good. A lot of times there’s still a misconception a little bit on: is Social Security taxable? Because everyone’s like, no tax on tips, no tax on overtime, no tax on Social Security. Well, there is tax on tips for a lot of people. You won’t get as much depending on your income. There is definitely tax on overtime for a lot of individuals, depending on your overall income. Dr. Friday 03:11 And then same thing with Social Security. Social Security in itself is tax-free, unless you have other earnings. If your other earnings exceed the $75,000 or $150,000 threshold, you start losing that $6,000 or $12,000 if married — the deduction that they are giving you to help pay for your Social Security. But Social Security still has to be reported on your tax return. That was one of the bigger misconceptions — sometimes people didn’t bring in their statements because they were under the impression that they no longer had to report Social Security as part of their income. Dr. Friday 03:50 So again, it’s confusing. Taxes are always confusing, which is partly the fun and partly the other side of it. We do our best to try to make sure that we’re giving everybody all the answers they need. But if you’re working on your taxes, maybe you’ve gotten something with inheritance, or you’re selling a piece of property that maybe at one point was inheritance and then you had to sell it or whatever — then that’s something you need to consider: what the basis is. Dr. Friday 04:21 Sometimes that can be a bit confusing. I’m going to suggest for a lot of people that if you have a piece of property that is going to be left to children or the next generation, look at a trust. I’m not an attorney — put that caveat out there — but there are a lot of good features of a trust. Part of it is there are ways of making sure that the basis is preserved and different things like that, especially for a husband and wife. I heard recently, and again this is what I heard, but an attorney said that if a home goes into a trust, and especially an A-B trust, that preserves the step-up for the wife. Dr. Friday 05:03 So there are different questions and different ways of doing some of this and making sure that the documentation is the easiest for those that are left behind is really the question. I got into a bit of a conversation with one of my clients — a young couple — and we were talking about how they had just had their first child and I’m like, have you set up a will? And they’re like, well, no, it’s on our list but we haven’t got there yet. And I’m like, well, you know, hopefully you’ll live to a nice old age. But we all know that things happen every day. And do you have things set up for what happens to that child if you’re not there to raise it? Dr. Friday 05:44 And of course that made them start thinking. These are the kinds of questions no one likes to answer or ask. But if you are a young person — because a lot of times people listening are people that are maybe closer to my age, in their late 50s or older, but some are younger — the average age listening to the station is probably around 40. Many of you have already had children or are at that point. Young people need to put some thought to not so much that you have an estate — you haven’t built all your wealth yet — but what will happen to your children, to the things you do have? Dr. Friday 06:22 Even though it doesn’t seem like it, I know most people think estate planning is really for people that have an estate. But think a little outside of that box. Think about estate planning especially when it comes to your children — maybe having life insurance to help them to the next level and learning more about how all that’s going to work, because that’s really the more important thing in my personal opinion. More important — estates can be settled in court. Not the ideal situation, but they can be. But i

    48 min
  8. Mar 2

    Dr. Friday Radio Show – February 28, 2026

    Dr. Friday takes live calls focused on practical tax decisions people are facing right now. She explains how capital gains work on inherited and sold property, why basis documentation matters, and why guessing tax numbers can create IRS problems later. The episode also covers Social Security withholding, the new age-based $6,000 deduction, home-sale exclusions, and rental-property recapture issues. Summary Points Dr. Friday explains that overtime tax relief applies to the overtime portion, not the entire hourly wage, and taxpayers should use employer records instead of estimates. A caller asking about an inherited property sale gets guidance on stepped-up basis at date of death, documentation options, and reporting gains on Schedule D. She notes that Tennessee residents who sell property in other states may still need to file a return in that state if taxable gain exists. Listeners are urged to review prepared returns carefully, ask line-by-line questions, and avoid ignoring IRS letters requesting support for amendments. During multiple calls, she clarifies that the age-based $6,000 amount is a deduction, not a refundable payment, and tax impact depends on income. Additional call-ins cover primary-home gain exclusions, family-related payment questions, and how rental sales can trigger both capital gains and depreciation recapture. Episode FAQ Q: Do seniors automatically avoid capital gains tax when they sell property? A: Not automatically. Age alone does not remove capital gains, though primary-home exclusions and lower-income capital-gain rates may help. Q: Is the new $6,000 amount a direct refund check? A: No. It is a deduction that can reduce taxable income, not a dollar-for-dollar refundable payment. Q: If I sell a former rental property, what can be taxed? A: The gain can be taxed as capital gains, and prior depreciation may be recaptured at ordinary tax rates. Transcript Announcer 00:00 But she can sure cure your tax problems or your financial woes. She’s the how-to girl. It’s the Dr. Friday Show. If you have a question for Dr. Friday, call her now. 737-WW-FC. That’s 737-9986. So here’s your host, financial counselor and tax consultant, Dr. Friday. Dr. Friday 00:29 It’s an absolutely gorgeous Saturday out there. My girl is outside making sure that no one sneaks up on the property. Apparently, you’ll hear in the background. If you want to join the show, you can at 615. 737-9986, 615-737-9986 is the number here in the studio. We talk about taxes. I am an enrolled agent licensed by the Internal Revenue Service to do taxes and representation. We have seen that a lot of the one big beautiful bill has helped out a lot of my tax people. Everyone will have their own. opinions on that, I suppose. Most people, if you’re in the the middle to low income, you will see benefits of the no tax on tips the uh tax uh extra tax or the refund on overtime as well as if you’re 65 and older getting that six thousand dollars And, you know, I mean again, some people will get more benefits. A lot of people still confused on how much of the overtime they’re able to take. Again, this is just the portion that is overtime. So if you make $10 an hour and overtime is $15, you’re only taking that $5 of overtime is the portion of overtime you’re able to deduct, but it’s still a good uh portion and it does work very well if you’re not sure uh how much you do need to either take a look at your final paycheck stub and or you need to contact your employer so they can make sure that whatever information you’re putting On your tax return is correct. I would not suggest I have um seeing a couple interesting things on the internet And I’m gonna be quite honest with you, I do not suggest guessing. I do not just say, oh, put whatever number you want, the IRS won’t know. You know Keep in mind the IRS has basically three years to go back and audit. They will be getting this information from employers. And if they do find it, guess what? You are responsible for all the information and even the information that a a tax preparer, let’s use that term instead of an enrolled agent because we don’t, but someone just throwing numbers on a return. So be careful. That will possibly or most likely come back and bite you. Okay. Looks like we’ve got Wayne in Jolton Um, this is Dr. Friday Show. Can I get you online? Caller 02:46 I’m here. Dr. Friday 02:48 Hello, sweetie. Caller 02:50 Hello. Thank you for taking my call. Dr. Friday 02:52 Sure. Caller 02:53 I have a Sumner County property, maybe a capital gains question. My brother sold some property for $80,000. And will we have to pay capital gains on that? Dr. Friday 03:10 Well is your does your brother pass away after he sold the property? Caller 03:14 No, no, he’s he’s still very much alive. Okay, okay. Dr. Friday 03:17 I didn’t mean to kill him off that fast. Um anyways, um it just depends on what his original basis is then so if he purchased the property for 80 and he sold it for 80 there’d be zero but if he purchased it for 40 000 let’s say held it for a number of years and now he got 80 000 he would pay tax on the difference or on 40 000 like that example Okay, this was inherited and given to the Okay, so does he when he inherited there would have been a basis or there should have been a basis established. So at the time of that person that passed away, within 30 days of their passing, when you to know what was that property worth if you don’t have any way of going back to appraisal you can usually look at property taxes that’s not always the best number but it is at least a viable number Caller 04:04 So the property So would they have would he have paid taxes on that at the time he inherited it? Dr. Friday 04:09 He wouldn’t have to. No. What he would have gotten is let’s say let’s just say um he passed the whoever died passed away a year ago. The property at the time of that passing was Worth $80,000. A year later, your brother sells it for $80,000. It would be zero tax. So what was the property? He needs to find out at the time of the property with whoever he received it from passed away. What was the value at that time? Oh okay. And then the difference between that and what he sold it for will be capital gains, if there is a difference. Caller 04:39 And that’ll be paid to the IRS, right? Dr. Friday 04:41 Yes, sir. And that will report on a schedule D on his personal return. Caller 04:46 I’ve heard you plenty of times. Thank you for talking to me. Dr. Friday 04:48 Hey, no problem. Thank you for calling. Okay, that was a good question. And um Go ahead, hang up. Um and I will say that is something that is sometimes confusing on when we inherit. And uh I I can’t put out enough. The best thing to do if if for some reason um it’s It’s a bad situation, but if some reason you have now inherited some property, or maybe you inherited it years ago, the best thing you could do is to get either a real estate agent, an appraisal company But you need to know what that basis is because otherwise the IRS is going to say your basis is zero. You didn’t purchase it, so you have no purchase documents. You inherited. What was the value of the property at the time? Time of inheritance. That’s what we need to know. Then it’s you know, many times I mean I have people claim losses because they’re not able to sell it for what it was worth with the time. Most of the time and tonight to see though we’re fortunate that our property doesn’t usually go down. It has a nice steady uphill um grade, at least at this point. But either way, you need to know and then if this property was not in the state of Tennessee, let’s say you sold you inherited a house in in Alabama, Kentucky, um they have state income tax. So you would also have to file a tax return there if there was a capital gains. So again in Tennessee, we do not, and just because you live in Tennessee, if you sell something in another state, there is normally a capital gains tax or a tax due at the time. of the sale. Inheritance-wise, most of the time we don’t pay anything, but at that time you will pay something and it will be time to have to do what you need to do, which is file taxes on it. So hopefully again, if you’re sitting on something You know, now before you decide to put it on the market would be a good time. So you’re not having to run around and try to figure it out after you’ve already sold it. And real estate agent um agents are really good. I have a number of them are friends, and especially if they’ve just sold the property, they can usually pull comps for when the person had passed away. So if you’ve just recently sold that property, you might be able to go back to the real estate agent, have them pull comps in that area. at the same time that the person passed away. So now you have something in writing that would say this is what it would have sold for back at the time that person would have sold at before they died. And then this is what you sold it for. You’ve got documentation to justify the numbers on your Tax return. All right. So let’s continue forward, making sure that we have everything we need to move forward on our life and trying to get to all of my emails. have been a busy day. But anyway, so if you um you’re working on your taxes, we are totally working on our taxes here. I will tell you uh at this point our calendar calendar is full to be honest, which is a blessing to have. Not always great when you’re always wanting to meet and help new people. If you’re a returning client, we usually have a space for you, but new clients, we won’t be able to do anything but file an extension and then help you out. But um either way, um if we can’t help you, we can try to refer somebody if we know of someone that um that’s available that hasn’t already has their calendar full. But if you have a tax question, maybe you’re doing your own ta

    47 min
4
out of 5
3 Ratings

About

The Dr. Friday Radio Show is a weekly radio show broadcast live on 99.7/WWTN every Saturday from 2PM-3PM CST. If you are outside of the listening area of the radio station (Nashville, TN), you can also download the iHeart App on your smartphone and search WWTN to hear the LIVE show. You can also listen to past episodes on the Dr. Friday Tax and Financial Firm website (https://drfriday.com), on Apple Podcasts, Google Play and many more.