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:
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• (00:00) - Exploring the New Senior Tax Deduction and Its Implications
• (05:16) - Tax Deductions for Seniors Aged 65 and Older
• (07:29) - Understanding Tax Deductions and Phase Outs for Married Couples
• (11:46) - Maximizing Senior Tax Deductions with Schedule 1A
• (16:29) - The Value of Tax Professionals and Avoiding Procrastination

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
• (00:34) - Importance of Tax Professionals
• (01:10) - Insights on the CPA Profession
• (02:22) - Choosing the Right Tax Professional
• (05:05) - Trust in Tax Professional Relationships
• (09:21) - Accreditation of Tax Professionals
• (11:59) - Understanding the X Factor
• (13:39) - Importance of Due Diligence and Price
• (15:34) - Closing Remarks

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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CHAPTERS
0:00 Exploring Tax Changes and Planning for 2026
2:34 Major Tax Changes and Deductions for 2025 and Beyond
6:46 High Taxes and Weather Jokes Between Michigan and Tennessee
7:14 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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EPISODE SPONSOR
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👉 https://www.wealthbuildersmortgagegroup.com

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🎧 Listen on your favorite podcast platform:
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👉 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

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:
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• (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
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🎧 Listen on your favorite podcast platform:
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👉 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

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

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🎧 Listen on your favorite podcast platform:
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👉 Apple Podcasts https://apple.co/3ZkyEtX
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👉 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