Teaching Tax Flow: The Podcast

Hosted by Chris Picciurro and John Tripolsky

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211

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Oct 2026

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About the 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 today. Produced and hosted by Teaching Tax Flow. www.TeachingTaxFlow.com

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60 recent

October 27, 202614 min

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 qualifying for a tax break doesn’t always mean getting the savings you expected. In this episode: • Tax credits vs. deductions: how they affect your tax calculation • A $100 deduction example using a hypothetical 25% marginal tax rate • Why deductible business expenses still cost you money • Refundable vs. nonrefundable tax credits • How deduction limits and itemizing affect your potential savings • Lessons from past electric vehicle and home improvement credit claims • Why you should talk to your tax professional before a major purchase #TaxCredits #TaxDeductions #TeachingTaxFlow ⸻ STUDIO SPONSOR Strategic Associates 👉 https://teachingtaxflow.com/studio EPISODE SPONSOR Symphony Life 👉 https://bit.ly/life-insurance-srp ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF

October 20, 202618 min

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 how AI is changing tax enforcement and what taxpayers and business owners should know. Defeating Taxes: https://defeatingtaxes.com ⸻ STUDIO SPONSOR Strategic Associates 👉 https://teachingtaxflow.com/studio EPISODE SPONSOR Legacy Lock Estate Planning Made Affordable, Fast & Easy 👉 https://www.teachingtaxflow.com/legacy ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:00) - IRS Uses AI to Audit Large Partnerships (05:00) - IRS Uses AI to Detect Anomalies in Corporate Tax Returns (08:58) - Leveraging Technology for Efficient Tax and Estate Planning (10:32) - IRS Leverages AI for Fraud Detection and Improved Taxpayer Service (16:29) - Engage With Teaching Tax Flow for Tax Advice and Community

October 13, 202621 min

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. Julie, an authority on the subject, shares her seasoned insights into how recipients of stock options should navigate this often confusing territory. Throughout the conversation, Julie explains the various types of equity compensation, including stock options, restricted stock units (RSUs), and employee stock purchase plans (ESPPs), providing valuable insights on when and how taxation occurs. The dialogue places special emphasis on the 83B election, a choice many employees face upon receiving stock options, especially in the startup ecosystem. With her humorous anecdotes and practical advice, Julie provides clarity on the critical timelines and tax considerations involved, ensuring that listeners walk away with a solid understanding of how to effectively manage their equity compensation and tax liability. 83(b) Election Guide https://www.83bguide.com ⸻ EPISODE SPONSOR Wealth Builders Mortgage Group 👉 https://www.wealthbuildersmortgagegroup.com STUDIO SPONSOR Strategic Associates 👉 https://teachingtaxflow.com/studio ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:00) - Understanding Employee Stock Options and the 83B Election (03:22) - Understanding Equity Compensation and the 83B Election (05:16) - Understanding Tax Implications of Equity Compensation and 83B Election (09:28) - Understanding Stock Options, Vesting, and Early Exercise (10:25) - Understanding 83B Elections in Stock Options and Equity (13:40) - The Critical Timeline for Filing an 83B Election (16:20) - Mortgage Solutions and Equity Compensation Guidance (17:44) - Understanding IRS Forms and Stock Option Tax Implications

October 6, 202617 min

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 a continuous, proactive process rather than a reactive one limited to the tax season. Strategic Associates sponsors this episode, reflecting a commitment to providing listeners with invaluable, actionable insights into efficient tax planning methods. The hosts stress the significance of assessing past tax returns as a starting point for creating effective future strategies. Chris highlights that comprehending behavioral and capital-driven aspects of tax strategies can lead to legally and ethically reducing tax liabilities over a lifetime. He underscores the necessity of implementing informed action plans, suggesting that even self-employed individuals and those with complex financial situations can benefit immensely from regular tax projections. The episode underscores that tax planning is not just about immediate deductions but involves setting clear, strategic goals that can yield long-term benefits. ⸻ EPISODE SPONSOR TaxHakr 👉 https://www.teachingtaxflow.com/plan Use code TTF for 15% off STUDIO SPONSOR Strategic Associates 👉 https://teachingtaxflow.com/studio ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:00) - Fourth Quarter Tax Planning Strategies for 2026 (02:09) - Using Tax Returns as a Financial Progress Report (05:19) - Strategic Tax Planning for Employees and Business Owners (07:49) - Effective Tax Planning Strategies and Stress Reduction Techniques (14:27) - Navigating Backdoor Roth IRA Contributions and Tax Implications (15:18) - The Importance of Early Tax Planning for Self-Employed Individuals (16:46) - Explore Tax Topics with Teaching Tax Flow Resources

September 29, 202617 min

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 types of income and transactions that, although not usually taxed, can create significant issues if not properly reported. This episode promises educational value for everyday taxpayers. At the center of the discussion is the critical distinction between reportable and taxable income. Chris Picciurro clarifies this distinction, drawing on examples such as the sale of a primary residence, gifts from family members, inherited stock sales, and digital asset exchanges. The hosts emphasize the importance of understanding how the IRS operates with information received through forms like 1099s and stress the consequences of failing to report even non-taxable income, which could lead to unexpected IRS notices. Through engaging conversations and real-life anecdotes, Chris and John not only highlight typical pitfalls but also offer practical steps to ensure compliance with tax laws. Defeating Taxes: https://defeatingtaxes.com ⸻ STUDIO SPONSOR Strategic Associates 👉 https://teachingtaxflow.com/studio EPISODE SPONSOR Symphony Life 👉 https://bit.ly/life-insurance-srp ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:00) - Understanding Reportable Versus Taxable Income to Avoid IRS Issues (03:23) - Understanding IRS Assumptions on Primary Residence Sales (05:47) - Gift Tax Exclusions and Reporting Requirements Explained (09:40) - Understanding Stepped-Up Cost Basis and Tax Implications (11:20) - Exploring Tax and Insurance Planning with Expert Insights (13:07) - Tax Implications of Digital Asset Exchanges and New IRS Forms (16:34) - Exploring Tax Topics and Resources for Financial Education

September 22, 202619 min

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. Texas, Florida, North Carolina, South Carolina, and Tennessee currently lead the list for growth. Conversely, California, New York, Illinois, New Jersey, and Massachusetts are seeing the most substantial population loss. By analyzing these US population shifts, we can better anticipate state tax trends that often follow such demographic changes. Tax Foundation: https://taxfoundation.org/data/all/state/state-migration-trends-map-americans-moving-population-changes/ Defeating Taxes: https://defeatingtaxes.com ⸻ STUDIO SPONSOR Strategic Associates 👉 https://teachingtaxflow.com/studio EPISODE SPONSOR Legacy Lock Estate Planning Made Affordable, Fast & Easy 👉 https://www.teachingtaxflow.com/legacy ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:00) - IRS Reveals Top States for Population Migration and Tax Impact (01:52) - State Income Tax and Population Migration Trends (08:06) - Factors Influencing Relocation Decisions and Tax Planning (10:27) - High Tax States and Migration Trends in the US (17:16) - Tax Planning and State Relocation Considerations

September 15, 202620 min

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 on revaluing assets at the time of sale and how this impacts depreciation recapture – a topic often overlooked in the financial audit of real estate transactions. The discussion provides a comprehensive look at how investors can leverage these advanced tax strategies to reduce ordinary income rate liabilities by reallocating gains to a more favorable capital gains tax rate. Chris highlights the unique benefits, such as permanent tax savings, that these strategies offer compared to traditional cost segregation. They emphasize the importance of fair market value and economic obsolescence in reducing tax recapture, particularly for property owners emerging from the pandemic market surge. Whether it's a short-term rental or a large apartment building, these strategies provide a savvy approach to saving money on taxes. Your Next Step www.csap.com/partner/teaching-tax-flow ⸻ STUDIO SPONSOR Strategic Associates 👉 www.teachingtaxflow.com/studio EPISODE SPONSOR Wealth Builders Mortgage Group Your trusted mortgage partner for investors and entrepreneurs. 👉 www.wealthbuildersmortgagegroup.com ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:01) - Strategies to Minimize Taxes When Selling Real Estate (02:48) - Understanding Section 1245 Exchange to Reduce Tax Recapture (09:21) - Wealth Builders Mortgage Group Empowers Real Estate Investors (09:53) - Maximizing Tax Savings Through Section 1245 Exchanges (13:03) - Tax Strategies for Real Estate Investors and Property Sales (20:26) - Financial Advice Disclaimer and Affiliation Disclosure

September 8, 202618 min

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 deduction, a little-known opportunity that could potentially save farmers significant money. Throughout the episode, Chris reveals the importance of leveraging nutrient-based tax deductions in farming. This specific deduction, often missed by farmers and tax professionals alike, revolves around the excess nutrients left in the soil by previous landowners, demonstrating a key opportunity to optimize tax filings and improve financial well-being. Your Next Step > acrebasis.teachingtaxflow.com ⸻ STUDIO SPONSOR Strategic Associates 👉 www.teachingtaxflow.com/studio ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:03) - Untapped Tax Deductions for Farmers Revealed (02:37) - Depreciating Soil Nutrients as Overlooked Farm Assets (06:27) - Tax Deductions for Landowners in the Farming Industry (08:46) - Tax Benefits and Strategies for Farm and Real Estate Owners (12:43) - Tax Strategies for Farmers and Multigenerational Farm Ownership (18:10) - Financial Advice Disclaimer and Affiliation Details

September 1, 202615 min

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 overlap to create a comprehensive understanding of income, appreciation, and inheritance. Diving deeper, Chris unveils his top 3 reasons to invest in real estate from a tax perspective. He explains how tax-free income can be generated through depreciation deductions, often leading to reported losses on tax returns despite positive cash flow. This episode extensively discusses concepts such as tax-deferred capital appreciation, highlighting real estate's potential to grow in value without incurring taxes until the property is sold, and the powerful 1031 exchange strategy, which allows investors to defer taxes indefinitely. The discussion also touches on the step-up in basis, a benefit where heirs inherit property at its current market value, potentially leading to significant tax savings. ⸻ STUDIO SPONSOR Strategic Associates 👉 www.teachingtaxflow.com/studio EPISODE SPONSOR Wealth Builders Mortgage Group Your trusted mortgage partner for investors and entrepreneurs. 👉 https://www.wealthbuildersmortgagegroup.com ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:44) - Chris' Top Three Reasons for Real Estate Investing (01:20) - Long-Term Benefits of Real Estate Investing (02:19) - Tax-Free Income in Real Estate (04:09) - Planning and Strategy for Real Estate Investment (05:14) - Tax-Deferred Capital Appreciation (07:32) - Step-Up in Basis for Inherited Property (11:48) - Real Estate vs. Other Asset Classes (14:33) - Conclusion and Wrap-Up

August 25, 202621 min

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 financial implications becomes crucial. The episode clarifies the need for parents to have a strategic plan to safeguard their children's income and future. Jimmy Strong, equipped with years of experience advising high-profile clients, emphasizes the importance of structuring finances right from the start. Key discussion points include establishing a manager-managed LLC, understanding potential income streams, and the need for proactive tax planning to minimize liabilities. This episode also delves into the specifics of navigating landscapes like NIL (name, image, likeness) revenue for young athletes, offering unique insights and actionable steps for parents to consider. ⸻ STUDIO SPONSOR Strategic Associates 👉 www.teachingtaxflow.com/studio EPISODE SPONSOR Legacy Lock Book a 30-minute complimentary discovery session at www.teachingtaxflow.com/legacy ⸻ 👉 Spotify https://bit.ly/3KdmtJL 👉 Apple Podcasts https://apple.co/3ZkyEtX 👉 Amazon https://amzn.to/4qmdqa5 👉 iHeart https://bit.ly/iheart-TTF (00:02) - Guiding Parents of Talented Minors Through Financial Considerations (03:34) - Financial Strategies for Young High Earners and Their Families (12:01) - Opportunities and Challenges in a Regulated Market Landscape (13:49) - Guiding Emerging Stars: Building Teams and Managing Wealth (21:37) - Teaching Tax Flow and Investment Advisory Services Overview

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