Podcast
Teaching Tax Flow: The Podcast
Hosted by Chris Picciurro and John Tripolsky · EN
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
34episodes
Episodes
Newest firstAll episodes
Ep. 170 | What's New in 2026
Jan 1300:18:14Tap to summarizeIn 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," including deductions on tips, overtime, and notable alterations to the standard deduction, all while providing strategies for optimization.The episode unfolds with a detailed exploration of the major tax adjustments for taxpayers beginning in the 2025 tax year, which will significantly impact 2026 tax filings. Key highlights include the introduction of new deductions, such as "No Tax on Tips" and "No Tax on Overtime," tailored to benefit a variety of income groups, while also shedding light on enhancements to the child tax credit and the preservation of the QBI deduction to bolster small business growth. The duo pepper the discourse with insights into extending bonus depreciation at 100%, making it a significant boon for eligible asset acquisitions, particularly in the real estate sector. Taxpayers are encouraged to consult trusted advisors and partake in the show's community to fully leverage these benefits.⸻EPISODE SPONSORWealth Builders Mortgage GroupYour trusted mortgage partner for investors and entrepreneurs.👉 https://www.wealthbuildersmortgagegroup.com⸻🎧 Listen on your favorite podcast platform:👉 Spotify https://bit.ly/3KdmtJL👉 Apple Podcasts https://apple.co/3ZkyEtX👉 Amazon https://amzn.to/4qmdqa5👉 iHeart https://bit.ly/iheart-TTF (00:00) - Exploring Tax Changes and Planning for 2026 (02:34) - Major Tax Changes and Deductions for 2025 and Beyond (06:46) - High Taxes and Weather Jokes Between Michigan and Tennessee (07:14) - Tax Deductions and Benefits for Seniors and Business Owners (10:25) - Tax Benefits and Strategies for Real Estate Investors (12:57) - Tax Planning Strategies and Changes for 2026 (17:53) - Investment Advisory and Securities Offerings Explained
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Ep. 169 | Charitable Deductions for 2026
Jan 600:24:05Tap to summarizeIn 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), the most significant overhaul of the tax code in about a decade. Chris and John shed light on the various changes that taxpayers, both those who itemize and those who don't, need to prepare for. The duo emphasizes the importance of tax planning and strategic timing to maximize deductions amid these new regulations.As the discussion unfolds, listeners get an in-depth understanding of the new above-the-line deductions for non-itemizers, the impact of AGI floors on charitable contributions for itemizers, and how high-income earners are affected by the new 35% cap on tax benefits. Chris offers practical examples to elucidate these changes, while John underscores the importance of awareness and planning to avoid unpleasant surprises when filing taxes. In addition, they explore how percentage limitations and carry-forward changes can affect deductions, especially for those donating appreciated property. This episode is a valuable resource for anyone seeking to understand and navigate the tax landscape in 2026.Key Takeaways:The One Big Beautiful Bill Act introduces substantial changes to charitable contributions starting in 2026.Non-itemizers can now benefit from above-the-line deductions up to $1,000 for singles and $2,000 for married couples filing jointly.Itemizers will encounter a new floor, set at half a percent of AGI, impacting the amount deductible from charitable giving.High-income taxpayers face a 35% cap on the tax benefit from their charitable donations.Episode Sponsor:Legacy LockBook a 30-minute complimentary discovery session at teachingtaxflow.com/legacy(Mention Teaching Tax Flow for special pricing) (00:00) - 2026 Charitable Contribution Changes and Tax Planning Insights (04:46) - Tax Deductions for Charitable Contributions in 2026 (10:40) - Maximizing Charitable Deductions for High-Income Taxpayers (16:06) - Effective Communication in Tax Advisory and Teaching (17:18) - Understanding Charitable Donation Deductions and Tax Implications (20:37) - Teaching Tax Flow's Upcoming Events and Community Engagement
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Ep. 168 | Commonly Missed Tax Deductions
Dec 3000:19:52Tap to summarizeIn 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 within your tax return, aiming to empower listeners with newfound tax knowledge ahead of their 2025 tax preparations. Whether navigating through state and local tax (SALT) deductions or understanding the minutiae of medical miles, this episode is a treasure trove of tax strategy.Throughout the episode, Chris emphasizes the importance of being proactive and informed about lesser-known deductions. The engaging dialogue reflects on key opportunities such as the state sales tax deduction for non-income tax states, and deductions related to medical miles, charitable miles, and student loan interest. For business owners, the conversation delves into the necessity of capturing deductions like startup costs, home office deductions, and retirement plan contributions. Chris also offers a critical look at rental property tax implications, discussing depreciation, passive activity loss carry forwards, and the Qualified Business Income (QBI) deduction.KEY TAKEAWAYS✅ State and Local Tax Savings - Beyond high-tax states, residents in non-income tax states can benefit from state sales tax deductions, particularly on significant purchases.✅ Medical and Charitable Miles - Deductions are available for medical-related travel and miles driven for charitable work, offering additional savings avenues.✅ Business Deductions - From startup costs to retirement plan contributions, business owners have multiple opportunities for tax savings that are often overlooked.✅ Rental Properties - Depreciation and passive activity loss carry forwards are crucial yet frequently missed savings on rental properties.✅ Engagement with the Community - The episode underscores the value of community engagement through platforms like the Defeating Taxes group for personalized tax insights.⸻Episode Sponsor:Strategic Associates, LLCRoger Roundywww.linkedin.com/in/roger-roundy-86887b23⸻🎧 Listen on your favorite podcast platform:👉 Spotify https://bit.ly/3KdmtJL👉 Apple Podcasts https://apple.co/3ZkyEtX👉 Amazon https://amzn.to/4qmdqa5👉 iHeart https://bit.ly/iheart-TTF (00:00) - Commonly Missed Tax Deductions and Financial Goals for 2026 (04:04) - Maximizing Tax Deductions Through Strategic Itemization (08:29) - Commonly Missed Tax Deductions for Individuals and Business Owners (14:41) - Maximize Rental Property Tax Deductions and Avoid Common Mistakes (17:50) - Year-End Tax Tips and Future Planning Strategies
Transcribe →Ep. 148 | Unveiling A Hidden Goldmine: QSBS Tax Exemption
Aug 12, 2025Tap to summarizeIn this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky welcome Brady Weller, co-founder of QSBS Rollover, to explore one of the most powerful — and most overlooked — tax planning tools for entrepreneurs: the Qualified Small Business Stock (QSBS) exemption.If you’re a startup founder, business owner, or investor looking to optimize your exit strategy, this conversation could save you millions in taxes. Brady breaks down IRC Section 1202, explaining how the QSBS exemption allows eligible C Corporation shareholders to exclude up to $10 million (or 10x their basis) in capital gains from federal income tax.The discussion also covers the QSBS rollover under IRC Section 1045, a strategy Brady likens to a “1031 exchange for company stock” — enabling sellers to reinvest gains into another qualified small business and defer taxes. The episode is packed with real-world applications, planning tips, and insight into recent legislative enhancements through the Inflation Reduction Act, which increased the QSBS exclusion cap and reaffirmed bipartisan support for innovation incentives.Whether you’re preparing for a major exit or just learning about QSBS for the first time, this episode is a masterclass in how to use specialized tax planning to unlock significant wealth.What You’ll Learn:• How QSBS works and who qualifies• The tax savings potential: $10M+ federal gain exclusion• How the QSBS rollover under Section 1045 defers taxes• Legislative updates that make QSBS even more attractive• State-by-state considerations for QSBS eligibility• Why early and specialized planning is critical for maximum benefitKey Insights:Brady Weller reveals how QSBS is often an untapped goldmine for founders — and why lack of awareness can mean leaving millions on the table. From structuring your business properly to timing exits and using rollovers, the right QSBS strategy can dramatically reshape your after-tax results.Notable Quotes:• “QSBS is one of the most powerful tax exemptions available, allowing federal income tax exemption on up to $10 million of gain.” – Brady Weller• “We dreamed of creating an always available, downside-protected option for founders to execute these rollovers successfully.” – Brady Weller• “OBBBA made QSBS even more powerful, expanding exclusion cap to $15 million, showing bipartisan support for this incentive.” – Brady Weller• “QSBS and its rollovers provide a 1031-type tax deferral for company stock, fundamentally transforming tax planning strategies for many.” – Brady Weller• “Our firm realizes around $3 billion in exit volume, emphasizing significant missed opportunities in the current system.” – Brady WellerResources:• QSBS Rollover Website• Connect with Brady Weller on LinkedIn• Teaching Tax FlowEpisode Sponsor:Strategic Associates, LLCRoger Roundywww.linkedin.com/in/roger-roundy-86887b23 (00:02) - Exploring Tax-Free Gains Through IRS Section 1202 QSBS (03:09) - Exploring Capital Gains Tax Mitigation with Brady Weller (05:19) - Exploring QSBS: A Powerful Yet Underutilized Tax Exemption (07:42) - Understanding Qualified Small Business Stock and Tax Exemptions (12:04) - Maximizing QSBS Benefits for Startup Founders Exiting Early (17:54) - Strategies for Starting or Acquiring a Business with QSPS Credit (19:36) - Understanding QSBS Rollovers and Tax Deferrals (21:15) - Navigating Related Party Rules in Business Exits (22:35) - The Future of QSBs and Tax Exclusions (24:37) - Exploring QSBS Rollover Benefits and Personalized Investment Advice (27:18) - Investment Offerings and Risk Factors in Financial Memorandums
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