Teaching Tax Flow: The Podcast

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.⸻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

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⸻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 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 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:REPStrackerwww.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 CommunityEpisode Sponsor:Legacy LockBook 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. EysterResources: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, LLCRoger Roundywww.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