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
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• (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