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), 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 Lock
Book 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

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 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.

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Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23

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🎧 Listen on your favorite podcast platform:
👉 Spotify https://bit.ly/3KdmtJL
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👉 Amazon https://amzn.to/4qmdqa5
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• (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

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 between taxpayer filings and IRS records. Chris presents a detailed walkthrough of these modifications, while John provides annotations, shedding light on potential impacts for tax professionals and individual filers alike.

The discussion begins by addressing enhancements to the tax reporting framework, focusing on the streamlined and comprehensive design intended to resolve past IRS matching discrepancies. By integrating changes into the core Form 1040, the IRS aims to avoid issues related to digital asset declarations, dependent statuses, and marital/separation statuses. Chris explains how taxpayers can effectively utilize these updates, outlining benefits like reduced correspondence with the IRS due to common errors. An additional focus on the new Schedule 1A highlights four temporary deductions meant to aid taxpayers in optimizing their returns, using enhanced preparatory strategies to file with confidence in an increasingly digital tax landscape.

SNEAK PEEK (2025 Form 1040): https://www.irs.gov/pub/irs-dft/f1040--dft.pdf

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KEY TAKEAWAYS

✅ Learn about the crucial updates to Form 1040 and how these changes aim to minimize IRS paperwork discrepancies.

✅ Insightful analysis of how new checkbox additions address various taxpayer statuses, including deceased individuals and residency queries.

✅ Discover the introduction of Schedule 1A, featuring four temporary deductions that could impact up to 40 million taxpayers.

✅ Tips on how these changes make tax preparation potentially more complicated, but also prevent errors and optimize financial strategies.

✅ The importance of staying organized in tax filing, particularly concerning tips and overtime income, to ensure an error-free submission.

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EPISODE SPONSOR
Wealth Builders Mortgage Group
Your 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 Changes in the New Form 1040
• (02:25) - Navigating Mortgage Strategies and Tax Return Complexities
• (04:11) - New Changes and Checkboxes on IRS Form 1040
• (08:08) - IRS Form Updates and Software Challenges
• (09:28) - New Tax Reporting Changes and Deductions on Form 1040
• (14:24) - Tax Filing Tips and Changes for a Smooth Process
• (16:15) - Holiday Tax Tips and Commonly Missed Deductions

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 Act.

Dubbed the “middle child” of tax legislation, Secure 2.0 introduces sweeping retirement changes beginning in 2025. Chris and John walk listeners through how these updates affect business owners, employees, and taxpayers approaching retirement age. From automatic enrollment requirements to expanded catch-up contributions, this episode highlights how Congress is actively nudging Americans toward better retirement behavior.

With relatable analogies, practical examples, and Chris’s personal milestone of turning 50, this episode turns complex legislation into actionable planning insight—helping listeners understand not just what changed, but how to use it strategically.

Key Takeaways:

• The Secure 2.0 Act modernizes retirement planning rules and fills the gap between major tax reforms.
• Taxpayers ages 60–63 gain access to enhanced catch-up contribution opportunities.
• Beginning in 2025, most new 401k and 403b plans must include automatic employee enrollment.
• Long-term part-time workers benefit from expanded retirement plan eligibility.
• The introduction of PLESSA accounts allows limited penalty-free access to retirement funds.

Episode Sponsor:
REPStracker

www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)

• (00:01) - Exploring the Secure 2.0 Act and Its Impact on Retirement
• (05:25) - Turning 50 Brings New Tax Benefits and Pickleball Opportunities
• (08:25) - Age, Music Preferences, and Tax Topics Discussed
• (09:49) - Secure 2.0 Act: Enhancing Retirement Plans and Accessibility
• (16:06) - Making Tax Planning Accessible for All Income Levels

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 healthcare expenditures while also enjoying significant tax advantages. As they explore the components of HSAs, they make complex financial concepts accessible, guiding listeners step-by-step through potential cost savings and tax efficiencies.

HSAs, as discussed in this episode, are not just mere savings accounts; they are a "tristar" tax-advantaged investments that offer threefold benefits: contributions are tax-deductible, the account grows tax-free, and withdrawals for qualified medical expenses remain tax-free. Chris relates his personal experiences and provides strategic advice, encouraging listeners to maximize their HSA contributions where feasible. Emphasizing actionable steps, the episode demystifies eligibility criteria and optimal usage scenarios for HSAs, reinforcing their potential in long-term financial planning.

Key Takeaways:

• Threefold Tax Advantage: HSAs offer a comprehensive tax benefit by allowing tax-free contributions, growth, and withdrawals for eligible medical expenses.
• Eligibility Criteria: HSAs require enrollment in a high-deductible health plan (HDHP) and have specific contribution limits that increase for individuals aged 55 and older.
• Flexibility: Unlike Flexible Spending Accounts (FSAs), HSAs roll over year-to-year, permitting funds to accumulate tax-free over time.
• Eligible Expenses: HSAs can cover a wide array of medical costs, including prescriptions, dental care, and vision expenses.
• Strategic Planning: Chris emphasizes starting early with HSA contributions, even for young individuals with minimal medical expenses, to optimize future healthcare budgets.

Resources

• Teaching Tax Flow Website
• Defeating Taxes Community

Episode Sponsor:
Legacy Lock
Book a 30-minute complimentary discovery session at teachingtaxflow.com/legacy
(Mention Teaching Tax Flow for special pricing)

• (00:02) - Understanding Health Savings Accounts and Their Tax Benefits
• (01:59) - Understanding HSAs and Their Tax Benefits
• (03:38) - Understanding Tax Benefits of Health Savings Accounts
• (04:44) - Understanding the Triple Tax Benefits of Health Savings Accounts
• (07:07) - Understanding HSA Eligibility and Contribution Limits
• (09:38) - Understanding HSA Contributions and Tax Benefits for Self-Employed
• (12:04) - Maximizing Health Savings Accounts for Medical Expenses
• (16:50) - Maximizing HSA Benefits for Future Medical Expenses
• (19:12) - Exploring Tax Benefits and Investment Advice

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 clear roadmap for navigating the rising costs of college by blending smart tax planning with proactive financial aid preparation. Brian demystifies the FAFSA process, explains major updates families must know, and shares actionable steps to maximize eligibility for need-based aid.

Throughout the conversation, Brian highlights how income, assets, and timing play crucial roles in how much financial aid a student may receive. Listeners learn the key differences between FAFSA and the CSS Profile, how the shift from Expected Family Contribution (EFC) to the Student Aid Index (SAI) changes planning conversations, and why starting early—ideally during a child’s sophomore year of high school—can make a measurable difference.

Parents also gain clarity on how certain assets work against them in the financial aid formula, what should be avoided at all costs, and how to strategically position their finances during the “base year” to legally and ethically reduce their SAI.

Notable Quotes

• “Our job is to try and get the SAI lower and lower—legally, ethically, and morally.” — Brian S. Eyster
• “Think of yourself playing a chess match. You can win a chess game with a multitude of different strategies in place.” — Brian S. Eyster
• “For parents of juniors… this is your last chance to do anything proactively regarding your income.” — Brian S. Eyster
• “Parents, it is highly inadvisable for your children to own the assets at the time you’re completing these forms.” — Brian S. Eyster
• “The best place to reach out is through our website, where you can book a 20-minute call to determine if we get along and like each other.” — Brian S. Eyster

Resources:

• Essential Strategies: Brian Eister’s company offers financial aid planning services.
• FAFSA Website: Official site for the Free Application for Federal Student Aid.

Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23

• (00:03) - Exploring FAFSA and Tax Strategies for College Aid Planning
• (04:37) - Strategic FAFSA Planning for College Financial Aid Optimization
• (12:40) - Understanding FAFSA and Asset Valuation for College Funding
• (16:19) - Understanding FAFSA and CSS for College Financial Aid
• (22:06) - The Importance of Annual FAFSA Completion for Financial Aid
• (25:25) - The Impact of Adjusted Gross Income on FAFSA and Taxes
• (26:26) - The Grad Process: Efficient College and Retirement Planning
• (31:03) - Aligning Business Relationships and Financial Planning
• (33:33) - Investment Advice and Legal Disclaimers in Financial Podcasts

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 understanding of tax brackets. Chris reveals why MTR is considered the primary Key Performance Indicator (KPI) for effective tax planning, emphasizing its critical role in guiding tax strategies and decisions.

Throughout the discussion, the distinction between marginal tax rates and tax brackets is elucidated, with Chris stressing the deceptive nature of tax brackets in comparison to the impactful MTR. He elaborates on how understanding one's MTR can drastically affect financial decisions and outcomes, particularly in tax planning contexts. Chris also touches on various elements like phase-outs and hidden taxes that influence one's marginal tax rate, offering listeners deep insights into tax planning. Highlighting the significance of implementing strategies that align with individual MTRs, Chris reinforces that comprehending one's MTR is pivotal to effective lifetime tax management.

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KEY TAKEAWAYS

✅ MTR vs. Tax Brackets: Marginal Tax Rate (MTR) is the most critical measure in tax planning, overshadowing the deceptive tax brackets.

✅ Tax Planning Strategy: Understanding and utilizing the MTR allows individuals to make informed choices, reducing taxes legally and ethically across their lifetime.

✅ Elements Affecting MTR: Chris highlights factors like phase-outs, deductions, and hidden taxes that can alter one's MTR significantly.

✅ Implementation over Ideas: Effective tax reduction hinges on implementing strategies that align with one's MTR to ensure maximum tax efficiency.

✅ Resources for Education: The podcast encourages utilizing Teaching Tax Flow content, such as YouTube and their community for further learning and clarity on tax concepts.

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EPISODE SPONSOR
Wealth Builders Mortgage Group
Your trusted mortgage partner for investors and entrepreneurs.
👉 www.wealthbuildersmortgagegroup.com

• (00:02) - Exploring Marginal Tax Rates and Real Estate Investment Strategies
• (01:56) - Understanding Marginal Tax Rate for Effective Tax Planning
• (04:43) - Understanding Marginal Tax Rate Versus Tax Bracket
• (06:49) - Understanding Marginal Tax Rate Versus Tax Bracket
• (08:16) - Understanding Marginal Tax Rates and Their Hidden Implications
• (11:50) - Understanding Marginal Tax Rate Versus Tax Bracket Misconceptions
• (13:28) - Understanding Marginal Tax Rates and Hidden Taxes
• (16:09) - Effective Tax Planning Through Strategic Implementation
• (17:51) - Tax Strategies and Professional Advice for Financial Planning

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 segment of the tax code, ensuring business owners and tax professionals understand its application, eligibility, and strategic use in financial planning.

With vivid explanations, the conversation revolves around the distinction between Section 179 and bonus depreciation, the importance of electing into Section 179, and its application across various business entities. Chris shares relatable anecdotes from his travels and hands-on teaching experiences, further contextualizing these complex tax concepts. Through practical examples and thoughtful guidance, listeners will gain a robust understanding of how to leverage Section 179 to its fullest potential, whether dealing with tangible property or considering the timing of significant purchases.

Key Takeaways:

• Understanding Section 179: Section 179 allows businesses to immediately expense qualifying property, unlike bonus depreciation which applies automatically unless opted out.
• Eligibility and Limits: The 2025 maximum deduction is $2.5 million, indexed for inflation, with a phaseout beginning at $4 million in property purchases.
• Business Entity Implications: Decisions to elect Section 179 deductions occur at the entity level, affecting partnerships, S Corps, and sole proprietors differently.
• Strategic Planning: Using Section 179 can be advantageous for spreading tax deductions over multiple years, especially for businesses with cyclic equipment purchases.
• Bookkeeping Importance: Accurate bookkeeping is crucial for tax efficiency; distinguishing between leases and purchases can impact deductions significantly.

Resources

• Teaching Tax Flow Website
• Defeating Taxes Community

Episode Sponsor:
Legacy Lock
Book a 30-minute complimentary discovery session at teachingtaxflow.com/legacy
(Mention Teaching Tax Flow for special pricing)

• (00:02) - Understanding Section 179 Deduction and Its Relevance
• (02:57) - Understanding Section 179 and Bonus Depreciation for Tax Benefits
• (06:09) - Tax Implications of Equipment and Vehicle Service Dates
• (08:04) - Maximizing Tax Benefits with Section 179 Deductions
• (13:50) - Understanding Section 179 Deductions for Business Owners
• (16:59) - The Importance of Accurate Bookkeeping for Effective Tax Planning
• (20:36) - Strategic Use of Section 179 Deduction in Business Tax Planning
• (23:09) - Exploring Tax Education and Community Engagement