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.

⸻

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.

⸻

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

In Episode 161 of the Teaching Tax Flow Podcast, hosts Chris Picciurro, CPA, and John Tripolsky welcome back special guest Parker Borofsky of Wealth Builders Mortgage Group to discuss one of the most common financial challenges entrepreneurs face — qualifying for a mortgage while self-employed.

Parker brings a lender’s perspective to this crucial topic, sharing real-world insights into how lenders view self-employment income, tax returns, and documentation when approving home loans. Together, the trio breaks down how tax planning decisions, deductions, and entity structures directly impact loan qualification, often in unexpected ways.

This episode offers invaluable advice for self-employed individuals, small business owners, and real estate investors looking to position themselves for mortgage success without sacrificing smart tax strategy.

Key Takeaways

• Self-employed borrowers often face more documentation hurdles than W-2 employees.
• Lenders analyze two years of tax returns and focus on net income, not gross revenue.
• Over-aggressive tax deductions can reduce qualifying income — balance tax savings with borrowing goals.
• Different lenders use varied methods to calculate income from K-1s, Schedule C, or corporate returns.
• Bank statement programs and alternative loan products can help bridge qualification gaps.
• Proper planning, documentation, and collaboration between your CPA and lender are critical for approval success.
• Start planning early — ideally six to twelve months before you apply for a mortgage.

Notable Quotes

1. “Tax strategy and mortgage qualification go hand in hand for the self-employed.” — Parker Borofsky
2. “The number one mistake I see is people writing off everything and then wondering why they can’t qualify.” — Chris Picciurro
3. “Income for lending and income for tax purposes are not always the same thing.” — Parker Borofsky
4. “If you’re self-employed, think long-term — what you claim on your return can make or break your loan.” — John Tripolsky
5. “Your lender and your CPA should be talking before you apply for a mortgage.” — Chris Picciurro

Resources

• Sponsor: Wealth Builders Mortgage Group — wealthbuildersmortgagegroup.com
• Teaching Tax Flow Hub: teachingtaxflow.com/hub
• Join the Defeating Taxes Community: defeatingtaxes.com
• Teaching Tax Flow YouTube Channel: youtube.com/@TeachingTaxFlow

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

• (00:03) - Mortgage Solutions for Self-Employed Individuals
• (03:38) - Navigating Mortgage Challenges for Self-Employed and Real Estate Investors
• (07:56) - Navigating Self-Employment Challenges in Mortgage Lending
• (15:52) - Self-Employed Loan Strategies and Bank Statement Programs
• (20:22) - Navigating Mortgage Options for Self-Employed and Investment Properties
• (28:13) - Navigating Real Estate Loans Without Tax Returns
• (32:23) - Exploring Tax Education Through YouTube and Podcast Collaboration

In this episode, Chris Picciurro, CPA, and John Tripolsky break down the IRS’s brand-new form: Schedule 1-A (Form 1040), created to handle new deductions introduced by the One Big Beautiful Bill Act (OB3).

Starting in the 2025 filing year, millions of taxpayers will use this form to claim deductions like No Tax on Tips, No Tax on Overtime Pay, Automobile Loan Interest, and Enhanced Deductions for Seniors.

Chris explains how these new “between-the-lines” deductions work, who qualifies, and why knowing your marginal tax rate is more important than ever.

KEY TAKEAWAYS
✅ Schedule 1-A is brand-new and will apply to millions of taxpayers starting in 2025.
✅ Includes four major new deductions under OB3.
✅ Each deduction has unique income phaseouts.
✅ Accurate documentation and understanding of eligibility are essential.
✅ Always verify if your state conforms to the new federal deductions.

RESOURCES
• Teaching Tax Flow Website: www.teachingtaxflow.com
• Defeating Taxes Community: www.defeatingtaxes.com
• Teaching Tax Flow YouTube Channel: www.youtube.com/@teachingtaxflow

EPISODE SPONSOR
Wealth Builders Mortgage Group
Strategic mortgage solutions for real estate investors.
Visit www.wealthbuildersmortgagegroup.com

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• (00:00) - Exploring IRS Schedule 1A and Investor Lending Strategies
• (01:56) - Exploring New Tax Deductions and Schedule 1A Implications
• (10:42) - Understanding No Tax on Overtime for Self-Employed Individuals
• (15:04) - Understanding New Tax Deductions and Their Broad Impact
• (20:30) - Exploring Tax Strategies and Resources on Teaching Tax Flow Podcast

In Episode 159 of the Teaching Tax Flow Podcast, hosts John Tripolsky and Chris Picciurro, CPA, tackle one of the most talked-about provisions of the One Big Beautiful Bill Act (OB3).. No Tax on Tips rule.

This episode cuts through the noise to clarify what “no tax” really means, who qualifies, and how tipped workers and self-employed individuals can take advantage of this new deduction starting in 2025.

Chris breaks down eligibility factors, income phase-outs, and which occupations are recognized as “customarily tipped.” From servers and stylists to rideshare drivers and entertainers, this new rule has far-reaching implications, but it’s not as simple as it sounds. The hosts also explore examples illustrating how this temporary deduction applies between 2025 and 2028, why voluntary tips matter, and what both employees and employers need to track to stay compliant.

KEY TAKEAWAYS
• The No Tax on Tips deduction (effective 2025 – 2028) allows qualifying workers to deduct up to $25,000 of voluntary tips from taxable income.
• Applies to both employees and self-employed individuals in occupations that customarily receive tips.
• Only voluntary cash or card tips qualify — automatic “service charges” are not eligible.
• Social Security and Medicare (FICA) taxes still apply — this affects only federal income tax.
• Phase-outs begin at $150 K (single) / $300 K (MFJ); full phase-out at $400 K (single) / $550 K (MFJ).
• Married couples must file jointly to claim the deduction.
• Proper record-keeping of all voluntary tips is essential for compliance and deduction accuracy.

RESOURCES
• Teaching Tax Flow Website: https://www.teachingtaxflow.com
• Defeating Taxes Community: https://www.defeatingtaxes.com
• YouTube Channel: https://www.youtube.com/@teachingtaxflow

EPISODE SPONSOR
Sunsets & Dinks
Save 15% at https://www.teachingtaxflow.com/pickleball with code TTF15

🎧 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

• (00:01) - Exploring IRS Policy on No Tax for Tips
• (01:38) - Temporary Tax Exemption on Tips from 2025 to 2028
• (05:13) - Understanding Qualified Tips and Occupational Eligibility for Tax Exclusion
• (11:01) - Understanding Tip Deductions and Income Phase-Outs for Tax Returns
• (16:33) - Teaching Tax Flow Podcast Offers Tax Tips and Investment Advice