PODCAST · business
Teaching Tax Flow: The Podcast
by Chris Picciurro and John Tripolsky
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 you can use to optimize your tax situation. We’ll also answer listener questions, share the mic with amazing guests, and share real-world examples to help illustrate key concepts.Whether you’re a freelancer, small business owner, real estate investor, or just looking to understand your taxes better, this podcast is for you. So tune in, take notes, and start building your confidence in taxes toda
Episodes
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Ep. 211 | Tax Credits vs. Deductions
What’s the difference between a tax credit and a tax deduction, and why doesn’t a tax write-off make your purchase free? The guys break down the confusion around credits, deductions, and the actual value of a tax benefit. From business expenses to medical deductions, this episode explains why...
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Ep. 210 | The IRS Is All-In on AI
The IRS is getting smarter with AI. What does that mean for your taxes? In this episode, John Tripolsky and tax expert Chris Picciurro, CPA, break down how the IRS uses artificial intelligence to flag income mismatches, select large partnerships for audits, and detect potential fraud. Discover…
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Ep. 209 | Smart Moves with Employee Stocks
In this episode of the podcast, co-hosts John Tripolsky and Chris Picciurro welcome Julie Merrill, CPA, to delve deep into the intricacies of employee stock options and the 83B election. This episode seeks to demystify the process of managing equity compensation with a focus on tax implications....
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Ep. 208 | Maximize Your Year-End Tax Game
In this episode of the Teaching Tax Flow podcast, co-hosts John and Chris dive into the crucial topic of year-end tax planning. As they note, with only 86 days left in 2026, taxpayers have limited time to optimize tax strategies. The episode emphasizes the importance of viewing tax management as…
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Ep. 207 | Reportable vs. Taxable Income
In this episode of the Teaching Tax Flow podcast, the guys delve into the complexities of IRS tax obligations that you might unexpectedly face. As they approach the Halloween season, a fitting time for conversations about potentially scary tax situations, Chris and John aim to shed light on four...
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Ep. 206 | Where Americans Are Actually Moving (And Why)
This episode breaks down the latest IRS data to show exactly which states are seeing the largest influx of residents and which are experiencing the most significant exodus. We look at the numbers behind the movement to help you understand the broader financial implications of these patterns.…
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Ep. 205 | Save Big with Reverse Cost Segregation
Chris Streit from CSA Partners is back on the podcast to dive deep into real estate tax strategies. You'll be introduced to innovative methods to minimize taxes payable upon selling a property, with a special focus on Section 1245 exchanges and reverse cost segregation. Chris shares his expertise...
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Ep. 204 | Hidden Tax Deductions for Farmers
This episode dives into Untapped Tax Deductions for Farmers! You'll hear all about an overlooked tax strategy dedicated to landowners and farmers, featuring special guest Chris Streit from CSA Partners. The episode promises to deliver crucial insights into residual soil nutrients as a tax...
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Ep. 203 | Long-Term Real Estate Investing + Taxes
In this episode, Chris Picciurro, a tax planning expert and real estate investing enthusiast, draws the strategic connections between long-term real estate investments and tax planning. He introduces listeners to the dynamic interplay between investment and taxation, in which different elements...
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Ep. 202 | Future Athletes (NIL) / Entertainers
In this eye-opening episode, John Tripolsky and Chris Picciurro welcome Jimmy Strong to discuss essential financial considerations for parents of talented minors. As children with unique abilities transition into high-earning scenarios in sports, entertainment, and other fields, understanding the...
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Ep. 201 | Tax Insights From Our "Conference Season"
In this episode of the podcast, hosts John Tripolsky and Chris Picciurro, CPA, dive into the dynamic and very insightful "conference season" for tax professionals. They take a broad look at the tax industry, focusing on various topics such as practice management, technology adoption, and what...
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Ep. 200 | Navigating Medicare
In this episode of the Teaching Tax Flow Podcast, John Tripolsky and Chris Picciurro, CPA, jump into the complexities of Medicare with expert guest Rebecca Jackson from Main Line Benefits. As healthcare continuity becomes crucial with age, understanding the nuances of Medicare can significantly...
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Ep. 199 | Big Tax Wins For $600K+ W-2 Earners
In episode 199 of the Teaching Tax Dlow podcast, co-hosts Chris Picciurro and John Tripolsky dive into strategic tax planning for W-2 wage earners who make over $600,000 annually. Following up on their previous discussion focused on individuals earning $100,000 or less, they target strategies…
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Ep. 198 | W-2 Employees $100K or Less: Top Tax Strategies
In Episode 198 of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky delve into impactful strategies for individuals earning $100,000 or less in annual W2 income. This episode is particularly valuable for those looking to maximize tax benefits and secure future financial...
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Ep. 197 | Unlocking Your 1040 (Tax Planning Tool)
In this episode of the Teaching Tax Flow podcast, host John Tripolsky welcomes Bill Park, the founder of TaxHakr, to explore the intricacies of the IRS Form 1040 and its untapped potential as a tool for effective tax planning. John and Bill delve into the concept of transforming the 1040 from...
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Ep. 196 | 2025 IRS Databook Compliance & Enforcement
In this episode of the Teaching Tax Flow podcast, Chris and John dig into the IRS Databook for fiscal year 2025, focusing specifically on compliance and enforcement. This episode is part two of a detailed exploration, following a previous discussion on the administrative insights from the IRS...
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Ep. 195 | 2025 IRS Databook Observations
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...
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Ep. 194 | Breaking Down Trump Accounts
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…
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Ep. 193 | Case Study: Joe & Jill Pickleball
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…
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Ep. 192 | Mastering Home Office Deductions
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…
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Ep. 191 | Scoop & Sprinkle's Sweet Success
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…
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Ep. 190 | Life Insurance & Taxes: Are You Making This Mistake?
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...
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Ep. 189 | Defining Tax Planning
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...
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Ep. 188 | Most Common 1099's
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...
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Ep. 187 | The Untapped Power of Property Tax Reviews
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...
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Ep. 186 | Divorce and Taxes: What Changes After Separation?
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...
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Ep. 185 | The Magic of Backdoor Roth IRAs
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"…
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Ep. 184 | Mind-Blowing Tax Tips for New Professionals
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...
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Ep. 183 | Cost Segregation Gets A Major Update
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...
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Ep. 182 | Don't Fall For the Tax Extension Lie
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...
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Ep. 181 | 2026 Inflation Tax Adjustments
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...
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Ep. 180 | SALT Tax Planning
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…
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Ep. 179 | Section 179 vs Depreciation. Which Saves You More?
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...
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Ep. 178 | Case Study: Mark & Jessica
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...
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Ep. 177 | Your Best Retirement Move: Roth vs. Traditional?
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…
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Ep. 176 | The Truth About Personal Boards of Directors
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...
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Ep. 175 | Top 5 Tax Myths
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!...
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Ep. 174 | When To Cut The Cord (on the kids)
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...
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Ep. 173 | Bonus Depreciation: When NOT to Claim It
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…
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Ep. 172 | The New Senior Tax Deduction
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…
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Ep. 171 | Don't Hire a Tax Pro Without Asking These Questions
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...
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Ep. 170 | What's New in 2026
In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky dive deep into the transformative tax changes set to take effect in 2026. As a follow-up to their previous discussions, they address crucial tax modifications outlined in the "One Big Beautiful Bill Act,"...
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Ep. 169 | Charitable Deductions for 2026
In this episode, co-hosts John Tripolsky and Chris Picciurro dive into the intricate world of 2026 tax changes to charitable contributions. Kicking off the new year, the guys provide a detailed analysis of what taxpayers can expect with the introduction of the One Big Beautiful Bill Act (OB3)…
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Ep. 168 | Commonly Missed Tax Deductions
In this episode of the Teaching Tax Flow podcast, hosts John and Chris usher in the New Year with invaluable insights into commonly missed tax deductions. Dubbing it a conversation you "may not want to admit is a problem," the discussion promises to shed light on often overlooked opportunities...
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Ep. 167 | A Sneak Peek at the New Form 1040
In this episode of the Teaching Taxable Podcast, co-hosts John Tripolsky and Chris Picciurro reveal significant updates to the 1040 tax form, aiming to prepare taxpayers for upcoming changes. Designed as a "holiday gift" to listeners, the episode dissects alterations targeting discrepancy issues...
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Ep. 166 | Unveiling the Middle Child: SECURE 2.0 Act
In Episode 166 of the Teaching Tax Flow Podcast, hosts Chris Picciurro, CPA and John Tripolsky break down the often-overlooked Secure 2.0 Act and explain why it plays a critical role in retirement and tax planning—even if it doesn’t get the same headlines as the Tax Cuts and Jobs Act or the OB3...
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Ep. 165 | The Triple Tax Benefits of Health Savings Accounts (HSAs)
In this episode of the Teaching Tax Flow podcast, hosts John Tripolsky and Chris Picciurro dive into the intricacies of Health Savings Accounts (HSAs), unpacking their extraordinary tax benefits. They highlight how HSAs can be a powerful financial tool for individuals looking to manage their...
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Ep. 164 | Student Aid + Tax Planning (FAFSA)
In this episode of the Teaching Tax Flow Podcast, hosts John Tripolsky and Chris Picciurro, CPA, sit down with college funding expert Brian Eyster to break down one of the most misunderstood financial planning topics for families: FAFSA and college financial aid strategy. Episode 164 delivers a...
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Ep. 163 | Marginal Tax Rates Matter Most
In this episode of the Teaching Tax Flow Podcast, host John and tax expert Chris delve into a pivotal topic in taxation - the Marginal Tax Rate (MTR). Sponsored by Wealth Builders Mortgage Group, the podcast aims to shed light on the intricacies of tax strategies that transcend the basic...
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Ep. 162 | The Section 179 Deduction Explained
In this episode of the Teaching Tax Flow podcast, hosts John and Chris jump into the intricacies of the Section 179 deduction, a crucial topic for small and medium-sized businesses seeking tax advantages through immediate expense on qualifying property. The episode demystifies this often-confused...
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ABOUT THIS SHOW
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 you can use to optimize your tax situation. We’ll also answer listener questions, share the mic with amazing guests, and share real-world examples to help illustrate key concepts.Whether you’re a freelancer, small business owner, real estate investor, or just looking to understand your taxes better, this podcast is for you. So tune in, take notes, and start building your confidence in taxes toda
HOSTED BY
Chris Picciurro and John Tripolsky
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Frequently Asked Questions
How many episodes does Teaching Tax Flow: The Podcast have?
Teaching Tax Flow: The Podcast currently has 211 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Teaching Tax Flow: The Podcast about?
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...
How often does Teaching Tax Flow: The Podcast release new episodes?
Teaching Tax Flow: The Podcast publishes regularly with 211 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Teaching Tax Flow: The Podcast?
You can listen to Teaching Tax Flow: The Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Teaching Tax Flow: The Podcast?
Teaching Tax Flow: The Podcast is created and hosted by Chris Picciurro and John Tripolsky.
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