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.

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CHAPTERS
0:04 Electing Out of Automatic Bonus Depreciation for Tax Benefits
4:11 Strategic Tax Planning and Bonus Depreciation Decisions
8:48 Tax Planning Strategies for Equipment and Vehicle Deductions
10:50 Maximizing Tax Benefits Through Strategic Bonus Depreciation Decisions
12:11 Efficiency of Travel and Tax Savings Compared
13:28 Introducing The Hub for Tax Planning and Partner Connections

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EPISODE SPONSOR
Strategic Associates, LLC
Roger Roundy
http://www.linkedin.com/in/roger-roundy-86887b23

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• (00:04) - Electing Out of Automatic Bonus Depreciation for Tax Benefits

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 deductions or chooses the standard deduction, potentially offering up to a $12,000 deduction for married couples. Additionally, they discuss the income phase-out range, highlighting the nuanced details that can affect one's tax return.

Episode Sponsor:
REPStracker

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• (00:00) - Exploring the New Senior Tax Deduction and Its Implications

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.

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• (00:00) - Introduction to Episode 171

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," 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.

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

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🎧 Listen on your favorite podcast platform:
👉 Spotify https://bit.ly/3KdmtJL
👉 Apple Podcasts https://apple.co/3ZkyEtX
👉 Amazon https://amzn.to/4qmdqa5
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• (00:00) - Exploring Tax Changes and Planning 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), 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
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• (00:00) - 2026 Charitable Contribution Changes and Tax Planning Insights

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
👉 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

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.

⸻

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

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

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

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