Chris Picciurro and John Tripolsky

Teaching Tax Flow: The Podcast

Business EN ↓ 196 episodes

Welcome to “Teaching Tax Flow: The Podcast”, the show that’s all about demystifying taxes and helping you keep more of your hard-earned income in your pocket. Hosted by tax experts from the Teaching Tax Flow team, this unfiltered (but clean) podcast is designed to empower you with the knowledge and tools you need to confidently navigate the world of taxes. We’ll cover everything from understanding tax laws and regulations to maximizing deductions and credits. In each episode, we’ll break down a specific tax-related topic in a clear and accessible way, providing practical tips and strategies yo...

Author

Chris Picciurro and John Tripolsky

Category

Business

Podcast website

www.teachingtaxflow.com

Latest episode

Jul 7, 2026

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Episodes

Ep. 195 | 2025 IRS Databook Observations 07.07.2026

Episode 195 of the "Teaching Tax Flow" podcast, Chris and John discuss the IRS Data Book for the fiscal year 2025. They break down the comprehensive data report to highlight essential insights into IRS collections, refunds, and the broader tax landscape. This episode is the first of a two-part series, with this particular installment zeroing in on the top administrative observations. The discussio...

Ep. 194 | Breaking Down Trump Accounts 30.06.2026

In this episode of the Teaching Tax Flow podcast, Chris Picciurro and John Tripolsky host Andrew Wallner, CPA, to decode the complexities surrounding Trump Accounts. This in-depth discussion delves into the intricacies of these newly introduced financial vehicles, shedding light on their structure, eligibility, and potential benefits. Andrew brings his wealth of knowledge to the table, offering li...

Ep. 193 | Case Study: Joe & Jill Pickleball 23.06.2026

In Episode 193 of the Teaching Tax Flow podcast, hosts John Tripolsky and Chris Picciurro jump into the intricacies of tax planning for early retirees with the case study of Joe and Jill Pickleball. This episode sheds light on strategies outlined in Chapter 19 of the Defeating Taxes book, providing valuable insights tailored for individuals transitioning from peak earning years to retirement while...

Ep. 192 | Mastering Home Office Deductions 16.06.2026

In Episode 192 of the Teaching Tax Flow Podcast, hosts Chris Picciurro, CPA and John Tripolsky revisit the often-overlooked, yet crucial, topic of the home office deduction. Designed to demystify the complexities surrounding this deduction, the episode provides listeners with essential information on legal requirements, potential audit fears, and the strategic application of the home office deduct...

Ep. 191 | Scoop & Sprinkle's Sweet Success 09.06.2026

In Episode 191 of the Teaching Tax Flow podcast, John Tripolsky and Chris Picciurro dissect a complex case study from Chris's book "Defeating Taxes." They delve into the story of "Scoop and Sprinkle," a married couple owning a thriving ice cream shop in a high-tax state. This episode emphasizes the critical importance of strategic tax planning for business owners experiencing significant income gr...

Ep. 190 | Life Insurance & Taxes: Are You Making This Mistake? 03.06.2026

Join Teaching Tax Flow for episode 190, where Chris Picciurro and John Tripolsky explore the intricacies of life insurance and its notable impact on tax strategies. In this riveting discussion, Jason Weiss from Symphony Life shares invaluable insights into the role of life insurance beyond the conventional view, illustrating why it's a critical component of smart financial planning. Throughout the...

Ep. 189 | Defining Tax Planning 26.05.2026

In this episode, listeners are welcomed into the intricate world of tax planning with insights from Chris Picciurro. As the self-proclaimed voice of tax planning, Chris, alongside his co-host, jumps deep into how strategic tax planning is not only about compliance but a forward-thinking mindset aimed at minimizing lifetime tax liabilities. This episode highlights the synergy between tax preparatio...

Ep. 188 | Most Common 1099's 19.05.2026

In this episode, listeners will gain a deep understanding of the 10 most prevalent 1099 forms, including 1099-NEC, 1099-MISC, and 1099-INT, among others. Chris Picciurro, CPA, covers the significance of proper reporting for tax accuracy and compliance, noting how modern payment methods and income streams have given rise to newer forms like the 1099-K and 1099-DA. This episode is a must for anyone...

Ep. 187 | The Untapped Power of Property Tax Reviews 12.05.2026

Welcome to Episode 187 of the Teaching Taxable Podcast. Hosts John Tripolsky and Chris Picciurro, along with guest Pat Gately from Leyton, jump into the often-overlooked area of property tax reviews. Many property owners view their tax assessments as unchangeable, but this episode reveals that reviewing and contesting them for accuracy can lead to significant tax savings. Pat shares his expertise,...

Ep. 186 | Divorce and Taxes: What Changes After Separation? 05.05.2026

In Episode 186 of the Teaching Tax Flow podcast, John and Chris cover the vital yet often overlooked topic of taxation in the context of divorce and separation. As disruptive as these life events are, understanding the tax implications can prevent financial surprises and help navigate the complexities with greater confidence. Their discussion aims to simplify the transition for those undergoing th...

Ep. 185 | The Magic of Backdoor Roth IRAs 28.04.2026

Welcome to episode 185 of the Teaching Tax Flow podcast, where hosts John Tripolsky and Chris Picciurro jump into the complexities of backdoor Roth IRA conversions. This episode is designed to guide high-income taxpayers, especially those familiar with Teaching Tax Flow's "red diagnosis" category, towards effectively contributing to tax-free vehicles like Roth IRAs despite income limitations. Thro...

Ep. 184 | Mind-Blowing Tax Tips for New Professionals 21.04.2026

We are back with episode 184 of the Teaching Tax Flow Podcast, diving into another one of the real-world case studies from the Defeating Taxes book. This episode features an in-depth discussion about the practical application of tax strategies. We explore various aspects to help you navigate complex financial scenarios and offer valuable insights into effective tax planning. "Defeating Taxes" NOW...

Ep. 183 | Cost Segregation Gets A Major Update 14.04.2026

We are back with episode 183 of the Teaching Tax Flow Podcast, revisiting cost segregation studies with Heidi Henderson of Engineered Tax Services. This discussion incorporates new regulations from the One Big Beautiful Bill Act, offering crucial insights into tax strategy and how accelerated depreciation can benefit taxpayers. We explore the nuances of depreciation and bonus depreciation to help...

Ep. 182 | Don't Fall For the Tax Extension Lie 07.04.2026

In this episode of the Teaching Tax Flow podcast, Chris Picciurro and John Tripolsky shine a spotlight on the often misunderstood concept of tax extensions. Together, they delve into the strategic benefits of utilizing tax extensions, debunk common myths, and provide listeners with a valuable perspective on how to integrate this tool into their financial planning. Chris and John explain that a tax...

Ep. 181 | 2026 Inflation Tax Adjustments 31.03.2026

In this episode, we discuss the intricate relationship between inflation and taxes, a crucial aspect of personal finance. We explore how current economic conditions impact your tax strategy and highlight which tax-related items have been adjusted for inflation and which have not. Understanding these dynamics is essential for effective money management. The HUB https://teachingtaxflow.com/hub Defea...

Ep. 180 | SALT Tax Planning 24.03.2026

Welcome back to the Teaching Tax Flow Podcast, episode 180! This week, we're diving deep into State and Local Tax (SALT) planning, a crucial aspect of your overall financial planning. We'll explore effective tax strategies for high-income individuals and share valuable tax tips to help you navigate these complex regulations.   "Defeating Taxes" NOW Available on Amazon www.defeatingtaxes.com The HU...

Ep. 179 | Section 179 vs Depreciation. Which Saves You More? 17.03.2026

Welcome back to episode 179 of the Teaching Tax Flow Podcast! In this episode, we tackle Section 179 of the IRS Code Book, a key component for any small business aiming for significant tax savings. We'll break down how bonus depreciation can enhance your tax efficiency and improve your strategic planning when acquiring new equipment. This discussion is crucial for understanding business taxes and...

Ep. 178 | Case Study: Mark & Jessica 10.03.2026

Welcome back to episode 178 of the Teaching Tax Flow Podcast! In this episode, we're diving into a specific case study from the " Defeating Taxes " book. We'll be using real-world case studies to provide practical insights, helping you better understand tax strategies and entrepreneurship. The discussion pivots on Mark and Jessica's life situation, exploring effective tax planning techniques for m...

Ep. 177 | Your Best Retirement Move: Roth vs. Traditional? 03.03.2026

On this episode of the Teaching Tax Flow podcast, we're diving into Roth vs. Traditional IRA accounts, essential for your financial education. We explore how these choices impact your retirement planning and overall tax/financial strategies. Join us for practical insights to help you make informed decisions about your financial future. EPISODE GUEST Andrew Charipar Charipar Wealth Management ⸻ EPI...

Ep. 176 | The Truth About Personal Boards of Directors 24.02.2026

This episode of the Teaching Tax Flow podcast tackles a frequently asked question: Do you need a personal advisory board? We explore what a personal board of directors entails for your personal life, distinct from corporate or non-profit structures. Join us to understand how this concept can contribute to your personal growth and overall financial development. The HUB https://teachingtaxflow.com/h...

Ep. 175 | Top 5 Tax Myths 17.02.2026

In this episode, we're diving into common tax misconceptions and debunking them once and for all. We'll be sharing essential tax facts and practical tax tips to help you with your tax planning. Join us for a crucial session of tax education and money education from the Teaching Tax Flow podcast! "Defeating Taxes" Now Available on Amazon https://www.bit.ly/4tDWJbz ⸻ EPISODE SPONSOR Legacy Lock Book...

Ep. 174 | When To Cut The Cord (on the kids) 10.02.2026

Chris Picciuro, CPA, and John Tripolsky explore the stages of introducing financial responsibility and tax education to children in this episode of the Teaching Tax Flow podcast. They discuss three phases: Supported Learning Years, Shared Responsibility Years, and Independence. Chris shares practical advice on how parents can gradually transition from financial providers to advisors, emphasizing t...

Ep. 173 | Bonus Depreciation: When NOT to Claim It 03.02.2026

This episode of the Teaching Tax Flow podcast dives into the intricacies of bonus depreciation, a crucial element for effective tax planning. We discuss how this tax deduction, reintroduced by the One Big Beautiful Bill Act, offers significant tax tips for small business owners looking to optimize their income tax liabilities. Understanding these business tax deductions is key to your tax strategy...

Ep. 172 | The New Senior Tax Deduction 27.01.2026

This episode provides a comprehensive analysis of the senior tax deduction, focusing on the eligibility criteria and unique advantages it offers. Chris and John highlight that individuals aged 65 and older with a valid Social Security number who file jointly or as head of household can benefit from this deduction between 2025 and 2028. The hosts clarify that it applies whether one itemizes deducti...

Ep. 171 | Don't Hire a Tax Pro Without Asking These Questions 20.01.2026

Welcome back to the Teaching Tax Flow podcast, episode 171! This episode guides you through selecting a tax professional and covers the importance of a CPA and an enrolled agent. We'll explore essential "interview" questions and answers to help you choose the right accountant or tax pro for your tax preparation and planning needs. Get ready to make informed decisions for your tax career. ⸻ 🎧 List...

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