The Dr. Friday Radio Show

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 ques...

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 esta...

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 not...

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, leadin...

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 shar...

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 inher...

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 t...

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...

Tax season is in full swing, and this episode centers on making smart filing decisions before deadlines hit. Dr. Friday opens with reminders for entity returns due March 15, then walks through live caller questions on deductions, IRA strategy, home-sale basis, and grant-funded wages. She also covers reporting side income correctly and planning ahead so tax results are less of a surprise. Summary P...

Tax season questions came in fast this week, and Dr. Friday opened by correcting confusion around overtime and tip-related tax treatment. She walked through RMD caller scenarios, including what to do after a late distribution and when extra documentation may be needed. The show also covered audit-ready recordkeeping, mileage versus vehicle write-offs, and practical questions on gifts and interest...

Tax season is open and Dr. Friday jumps right in, clearing up confusion around tips and overtime deductions and the documentation required. She warns against preparers who charge by refund or fabricate numbers, then takes calls on senior deductions, energy credits, gift tax rules, IRS resolution delays, and business/investment questions. Summary Points Tips and overtime deductions must be backed b...

This week, Dr. Friday breaks down the Trump account election (Form 4547) and what it means for parents, grandparents, and employers. She also revisits tips and overtime reporting, the new car loan interest deduction, and the recordkeeping needed for basis and mileage. The show closes with guidance on selecting ethical preparers and staying ahead of 2025 filing changes. Summary Points Form 4547 ele...

Kick off the 2025 filing season with Dr. Friday as she walks through the additional senior deduction and how the new tips and overtime deduction works at year end. She stresses documentation, correct W-2 reporting, and the importance of keeping business and personal records separate. Callers ask about overtime calculations, hobby vs business income, filing status after a spouse’s death, car...

While taxes are usually the star of the show, Dr. Friday takes a detour “off the grid” this week to discuss a critical component of business health: cybersecurity. Joined by Matt Folker and Dennis Buzard from Innovative Solutions Through Technology (ISTT) , Dr. Friday explores why small and medium-sized businesses are often the most vulnerable to hackers. From “sniff tests”...

In this episode, Dr. Friday is joined by her long-time friend and colleague, Hank Parrott of Estate and Financial Strategies. Together, they dive deep into the critical importance of the “Team Approach”—ensuring your financial planner and tax professional are working in unison rather than in silos. As we head into the new year, Hank and Dr. Friday discuss how to maximize your retiremen...

In this episode, Dr. Friday is wrapping up 2025 with critical updates on the “One Big Beautiful Bill” (OBBBA) and what the changing tax landscape means for your wallet. With the holiday season in full swing, Dr. Friday takes a break from her beehives to break down the new 2025 tax brackets, the major increase in the SALT deduction, and the newly established “Trump Fund” for...

Is your estate plan a “cure” or a “woe” for your family? In this episode, Dr. Friday is joined by board-certified estate planning attorney Russ Cook of the Cook Telman Law Group . With over 30 years of experience, Russ dives into the critical steps every family should take to protect their assets from creditors, minimize taxes, and avoid the public headaches of probate. Fro...

G’day! In this episode of the Dr. Friday Show, the Doctor is in the house to help you navigate the end of the year and prepare for the 2025 tax season. Dr. Friday breaks down the major changes introduced by the “One Big Beautiful Bill” (OBBB), including shifting tax brackets, new credits for families, and substantial changes for service industry workers. Whether you are looking t...

On this episode, Dr. Friday dives into critical year-end tax planning strategies and offers expert advice for listeners facing tough IRS issues. From the tax implications of an inheritance to navigating W-4 withholding for multiple jobs, Dr. Friday provides actionable steps to protect your finances. Learn the pitfalls of dealing with national tax resolution firms, the strict rules for vehicle dedu...

This week, Dr. Friday discusses the approaching 2024 tax deadline and dives into significant new tax deductions for 2025 concerning overtime pay and seniors over 65. The show also covers crucial topics such as the tax implications of selling a home, how large income events can trigger higher Medicare (IRMAA) payments, the right way to deduct business mileage, and how to navigate tax filings during...

On this beautiful Saturday, Dr. Friday tackles some confusing tax changes and answers crucial listener questions. The show kicks off by clearing up the chaos around the 1099-K reporting thresholds, explaining exactly what the “One Big Beautiful Bill” means for individuals using payment apps like PayPal and Venmo. Dr. Friday also dives deep into a significant new tax deduction for senio...

With the November 3rd deadline for 2024 tax returns fast approaching, Dr. Friday is in the studio to tackle some of the most pressing tax questions. In this episode, she breaks down the new “one big beautiful bill,” specifically clarifying the $6,000 deduction for seniors over 65 and how it impacts your bottom line. Dr. Friday also dives into the complex tax implications of selling ren...

Dr. Friday is back in the house! After a couple of weeks away, she returns to tackle the most pressing financial questions. In this episode, Dr. Friday breaks down the crucial November 3rd tax deadline for 2024 returns and clarifies the rules around estimated tax payments for 2025. She also discusses the impacts of a potential government shutdown on IRS refunds, dives into the major changes from t...

On this rainy Saturday, Dr. Friday jumps right into critical tax information, starting with an urgent reminder about the upcoming September 15th deadline for S-Corps, Partnerships, and LLCs, which is not covered by the federal disaster extension. She then unpacks the major tax law changes coming in 2025, including a new senior deduction, tax-free tips and overtime, and a deduction for auto loan in...

She’s not a medical doctor, but she can cure your financial woes! On this episode, Dr. Friday dives into the most pressing tax topics for today. With the November 3rd extension deadline for 2024 taxes looming, she explains why it’s crucial to get those returns filed before you can effectively plan for the new year. Then, she unpacks the massive changes coming in the 2025 tax year, including...