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• (00:02) - Tax Planning Benefits for Young Professionals in Low Tax Brackets
• (05:36) - Maximizing Tax-Free Growth Through Roth Retirement Contributions
• (08:31) - The Importance of Early Retirement Savings and Tax Strategies
• (10:05) - Financial Planning Tips for Young Professionals
• (14:18) - Empowering Young Adults for Long-Term Financial Success

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• (00:02) - Exploring Cost Segregation Studies and New Tax Regulations
• (02:41) - Understanding Cost Segregation and Its Impact on Tax Deductions
• (09:45) - Understanding Cost Segregation and Its Tax Benefits
• (14:51) - Leveraging Cost Segregation for Active Short-Term Rentals
• (17:59) - Understanding Bonus Depreciation Rules for Property Investments
• (20:52) - Understanding Cost Segregation Studies and Tax Implications
• (23:36) - Understanding Financial Advice and Investment Services

Chris and John explain that a tax extension is not a signal of negligence or a red flag to the IRS, but rather a strategic maneuver to ensure accurate and comprehensive tax filing. They stress the importance of understanding that tax extensions grant additional time to file returns, not to pay taxes, and they illustrate scenarios in which taking an extension can be beneficial. The discussion emphasizes how tax extensions can aid in maximizing deductions, aligning deductions with high-income years, and reducing potential errors and audit risks. 

They also share insights into specific tools like cost segregation studies and SEP IRAs, which can play a critical role when extensions are adequately utilized.

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• (00:04) - Tax Extensions as a Strategic Planning Tool
• (05:33) - Tax Extensions as a Planning Tool and IRS Partnership
• (06:57) - Optimal Timing for Better Experiences in Dining and Services
• (09:13) - The Importance of Filing Tax Extensions Accurately and Timely
• (11:06) - Strategic Tax Planning with Bonus Depreciation and Deductions
• (13:08) - The Benefits of Filing a Tax Extension
• (15:06) - Tax Extensions as Strategic Tools for Business Owners
• (16:39) - Understanding Tax Filing Extensions and Their Limitations
• (18:38) - Financial Advice Disclaimer and Affiliation Details

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• (00:02) - Understanding Inflation's Impact on Taxes and IRS Adjustments
• (03:15) - Tax Changes and Deductions Under the One Big Beautiful Bill
• (09:38) - Understanding Marginal Tax Rates and Their Impact on Deductions
• (15:23) - Generous Standard Mileage Deduction and Health Savings Accounts
• (17:05) - Maximizing Tax Benefits Through Strategic Planning and Contributions

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• (00:03) - Exploring State and Local Tax Planning Changes
• (01:38) - Impact of SALT Deduction Limits on High-Tax States
• (04:49) - Understanding SALT Tax Deductions and Their Implications
• (09:48) - Tax Changes and Estate Planning Made Easy
• (10:56) - Tax Strategies for Business Owners to Maximize SALT Deductions
• (17:05) - Teaching Tax Flow Podcast Encourages Listener Engagement

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• (00:01) - Exploring Section 179 Tax Deduction with a Play-Doh Analogy
• (01:22) - Section 179 and Bonus Depreciation for Tax Flexibility
• (07:00) - Tax Rules, Inflation Indexing, and Santa's Bad List
• (09:12) - Understanding Section 179 Deductions for Business Assets
• (11:50) - Strategies for Reducing Tax Liability for High Earners
• (13:11) - Tax Deductions for Commercial Building Improvements
• (14:28) - Understanding Depreciation and Tax Deductions for Business Assets
• (17:17) - Exploring Tax Resources and Historical Anecdotes
• (18:59) - Understanding Financial Advice and Investment Services

The discussion pivots on Mark and Jessica's life situation, exploring effective tax planning techniques for middle-income families. Chris unpacks the steps involved in transforming a "simple" tax return into a powerful instrument for financial growth and resilience. Topics highlighted include strategic retirement contributions, leveraging HSAs and FSAs, and important estate planning tips that go beyond mere asset accumulation. Through this enlightening conversation, listeners can learn how to align their financial goals with effective tax-saving methods, ensuring a secure future for themselves and their dependents.

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• (00:01) - Exploring Tax Strategies Through Mark and Jessica's Case Study
• (03:05) - Tax Planning and Strategy for Moderate Income Households
• (06:27) - Understanding Marginal Tax Rates and Their Impact on Income
• (08:23) - Financial Planning for New Homeowners with an Infant
• (10:25) - No Such Thing as a Simple Tax Return
• (12:04) - Maximizing Retirement Contributions and Tax Efficiency for Couples
• (14:36) - The Importance of Life Insurance and Estate Planning
• (15:50) - Maximizing Tax Efficiency Through Strategic Financial Planning
• (20:41) - Teaching Tax Flow: Insights and Community Engagement

Join us for practical insights to help you make informed decisions about your financial future.

EPISODE GUEST
Andrew Charipar
Charipar Wealth Management

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• (00:01) - Roth Versus Traditional Retirement Accounts Explained
• (01:07) - Choosing Between Roth and Traditional Retirement Accounts
• (05:38) - Andrew Charper's Journey into Financial Advising and Client Connections
• (08:06) - Financial Planning for Young Adults: Traditional vs. Roth Contributions
• (09:16) - Financial Strategies for High Earners and Life Changes
• (14:00) - Financial Planning Strategies for Variable Incomes and Tax Optimization
• (16:28) - Managing Financial Distractions in Your 40s
• (17:58) - Financial Strategies for Different Life Stages and Tax Planning
• (22:31) - The Importance of Collaboration Among Financial Professionals
• (25:36) - Teaching Tax Flow's Educational Insights on Financial and Tax Advice

We explore what a personal board of directors entails for your personal life, distinct from corporate or non-profit structures. Join us to understand how this concept can contribute to your personal growth and overall financial development.

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• (00:01) - Understanding the Importance of a Personal Board of Directors
• (03:42) - Building Your Financial Board of Directors
• (07:19) - Building Financial Relationships for Future Home and Asset Purchases
• (11:40) - Building a Personal Board of Directors for Business Success
• (18:04) - Educational Insights on Tax Flow and Financial Advice

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• (00:04) - Unveiling Tax Myths and Strategies in Defeating Taxes
• (02:18) - Debunking Tax Myths and Emphasizing Control Through Planning
• (05:51) - Debunking Tax Myths and Effective Tax Planning Strategies
• (16:05) - Navigating IRS Challenges with Taxpayer Advocacy and Professional Help
• (18:56) - Teaching Tax Flow and Engaging Tax Planning Strategies

⸻

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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• (00:03) - Teaching Kids About Taxes and Financial Responsibility
• (07:41) - Guiding Children Through Financial Independence Stages
• (15:21) - Wealth Builders Mortgage Group Empowers Real Estate Investors
• (15:52) - Teaching Financial Independence Through Staged Learning and Budgeting
• (21:26) - Engage in Tax Planning and Share Tips on YouTube

⸻

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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• (00:04) - Electing Out of Automatic Bonus Depreciation for Tax Benefits
• (04:11) - Strategic Tax Planning and Bonus Depreciation Decisions
• (08:48) - 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

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

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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

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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• (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

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

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:
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Roger Roundy
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• (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

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.

⸻

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• (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

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:
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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

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:
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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

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

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

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

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

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

🎧 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 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

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

Jeremy, known for blending his academic background with real-world tax expertise, breaks down what truly defines material participation and why it matters so much for real estate investors, high-income earners, and business owners. This episode provides a clear and actionable discussion of IRS Section 469, passive activity rules, and how to correctly apply the “seven tests” to determine whether income is passive or active.

Listeners will gain practical insights on documentation, common misconceptions, and how education remains key to staying compliant while maximizing benefits.

Key Takeaways

• Material participation determines whether you can use passive losses to offset active income.

• The IRS defines seven tests for material participation under Section 469 — understanding which applies to your situation is critical.

• Proper documentation (time logs, spreadsheets, or tracking apps) is essential for substantiating material participation claims.

• Not every real estate investor qualifies as a “real estate professional” for tax purposes — W-2 employees often don’t meet the test.

• Continuous education is vital for both tax professionals and clients to navigate evolving tax law and avoid misinformation.

Notable Quotes

• “We can’t really shut down bad information. All we can do is fight against it with good information.” — Jeremy Wells

• “The goal here, if you’re the taxpayer, is to try to have active income offset with those passive losses.” — Jeremy Wells

• “Just because you have a real estate license doesn’t make you a real estate professional for tax purposes necessarily.” — Jeremy Wells

• “You need to keep that contemporaneous log… just like mileage tracking for your real estate portfolio.” — Jeremy Wells

• “Education is still a key part of the work that I’m trying to do.” — Jeremy Wells

Resources

• Teaching Tax Flow Website: https://www.teachingtaxflow.com

• Defeating Taxes Community: https://www.defeatingtaxes.com

• Teaching Tax Flow YouTube Channel: https://www.youtube.com/@TeachingTaxFlow

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

• (00:00) - Demystifying Material Participation for Taxpayers and Investors
• (02:51) - From Academia to Accounting: A Journey of Career Change
• (07:17) - Understanding Material Participation and Passive Activity Loss Rules
• (17:33) - Understanding Real Estate Professional Status for Tax Purposes
• (21:20) - Tracking Hours and Activities for Real Estate Tax Benefits
• (26:00) - Jeremy Wells Discusses Tax Education and Client Engagement

Chris explains why an LLC is first and foremost a legal entity (not a magical tax shield), while John adds real-world insights on naming, filing, and keeping your compliance in check. Together, they break down the formation process, discuss the importance of operating agreements, and clarify ongoing responsibilities such as renewals, EIN filings, and state fees.

Key Takeaways

• An LLC stands for Limited Liability Company — a legal structure, not automatically a tax advantage.

• Your attorney may get more excited than your CPA — LLCs protect assets, but don’t inherently cut taxes.

• Steps include: naming your LLC, appointing a registered agent, filing Articles of Organization, creating an Operating Agreement, and obtaining an EIN.

• Treat your Articles of Organization like your LLC’s birth certificate and your EIN as its Social Security number.

• Keep personal and business funds separate — open a dedicated business bank account.

• Stay compliant with annual (or bi-annual) state renewals and any required franchise, excise, or withholding tax filings.

• Avoid over-structuring — multiple LLCs create unnecessary admin and costs if not justified by risk.

Notable Quotes

• “An LLC is a legal entity, not a tax-saving machine.” – Chris Picciurro

• “The name doesn’t matter — the purpose does.” – John Tripolsky

• “Think of your Articles of Organization as your birth certificate.” – Chris Picciurro

• “It’s easy to form one; maintaining compliance is where people fall short.” – John Tripolsky

• “Ideas are cheap. Implementation is valuable.” – Chris Picciurro

Resources

• Wealth Builders Mortgage Group (Sponsor): wealthbuildersmortgagegroup.com

• Teaching Tax Flow Hub: teachingtaxflow.com/hub

• Join the Defeating Taxes Facebook Community: defeatingtaxes.com

• (00:00) - Exploring LLC Formation and Investor-Focused Mortgage Strategies
• (01:43) - Understanding LLC Formation and Its Legal and Tax Implications
• (12:49) - Steps to Form and Maintain an LLC
• (17:23) - Navigating LLC Formation: Costs, Compliance, and Strategic Planning
• (21:40) - Educational Tax Advice and Investment Guidance

Marit shares practical insight from years of hands-on experience helping business owners implement proactive tax plans—emphasizing organization, accurate bookkeeping, and collaboration with your tax professional. Together, the trio highlight how cash-basis timing, depreciation, reimbursable plans, and entity structure play critical roles in shaping your 4th-quarter tax outcomes.

Key Takeaways

• Get your books in order — profit & loss, balance sheet, payroll, and distributions must be accurate before planning.
 • Understand that a deduction ≠ a tax-free purchase. A $100K vehicle deduction doesn’t eliminate $100K in taxes.
 • Avoid depreciation traps — bonus depreciation and vehicle write-offs can cause painful recapture if sold too soon.
 • Use the cash-basis “twelve-month rule” to prepay eligible expenses or defer income strategically.
 • Set up an accountable plan for home-office, mileage, and reimbursements before year-end.
 • Track all subcontractor payments and W-9s now—don’t scramble during 1099 season.
 • Above all: buy only what you need—don’t let the tax tail wag the dog.

Notable Quotes

• “Buying a vehicle might be good, but it’s not a tax plan.” – Chris Picciurro
 • “A $100K deduction doesn’t mean you’re saving $100K in taxes.” – Marit Burmood
 • “Cash flow and tax flow are different.” – Chris Picciurro
 • “Don’t buy it if you don’t need it—be logical, not emotional.” – Marit Burmood

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)

• (03:09) - Entrepreneurial Tax Strategies for Business Owners in October
• (08:56) - Understanding Tax Misconceptions and Effective Business Financial Planning
• (16:50) - Understanding Depreciation Recapture and Tax Implications for Businesses
• (21:19) - Tax Strategies for Small Businesses and Real Estate Investments
• (26:50) - Tax Strategies for S Corp and Small Business Owners
• (35:45) - Effective Tax Planning Through Communication and Organization

From audit rates to revenue collection, Chris and John provide context for business owners, individuals, and tax professionals on how these insights can influence financial and tax planning. They also share practical stories, analogies, and analysis that make the data approachable and useful.

Key Takeaways:

• Less than 0.38% of individual tax returns are audited annually.
• 54.2% of all federal tax revenue comes from individual income tax.
• IRS audit rates are higher for lower-income taxpayers claiming refundable credits.
• Partnerships and multi-member LLCs face remarkably low audit risks.
• AI and analytics are transforming how the IRS monitors compliance.

Notable Quotes:

• “Tax agencies are your involuntary business partner. Don’t you want to know what your business partner is up to?” – Chris Picciurro
• “When you get audited by the IRS, usually what happens is you just got pulled over going five miles over the speed limit in a car.”  – Chris Picciurro
• “93% of tax returns are filed electronically.”  – Chris Picciurro

Resources:

• Teaching Tax Flow Website
• DefeatingTaxes.com
• 2024 IRS Data Book (Publication 55B)

Episode Sponsor:
REPStracker

www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)

• (00:01) - Exploring the 2024 IRS Data Book and Tax Planning Insights
• (05:14) - Understanding Tax Collection and Processing in the United States
• (07:08) - The Evolution of Tax Filing and IRS Enforcement
• (13:19) - Understanding IRS Audit Risks and Processes
• (23:13) - Navigating IRS Notices and Engaging with Tax Resources

Chris and John break down how this above-the-line deduction works, the criteria for qualifying, and the potential pitfalls for taxpayers. From vehicle requirements to phased-out income thresholds, they explain how this law is designed to incentivize specific behaviors and how taxpayers can maximize the benefit.

The episode also includes case studies and examples showing how taxpayers in different income brackets may be affected, emphasizing the importance of marginal tax rate planning to understand the real financial impact.

What You’ll Learn:

• The specifics of the new automobile loan interest deduction under OB3

• Requirements for eligibility (new vehicle, U.S.-assembled, secured loan)

• How phase-outs at $100K (single) and $200K (married filing jointly) affect deductions

• Practical examples of how different taxpayers qualify—or don’t

• Why your marginal tax rate (MTR) is a critical metric for evaluating tax strategies

Key Insights:

This new provision could provide meaningful savings for qualifying taxpayers, but the rules are nuanced. Proper planning ensures you avoid phase-out surprises and maximize deductions where possible.

Notable Quotes:

• “Tax laws are written to encourage and discourage certain behaviors.” – Chris Picciurro

• “Now there’s a deduction on a personal tax return for qualified automobile loan interest.” – Chris Picciurro

• “For every thousand you’re over, you lose a deduction of $200.” – Chris Picciurro

• “Your number one KPI in tax planning is your marginal tax rate, not your tax bracket.” – Chris Picciurro

• “If you’re over $100,000 in income, you start getting phased out of this deduction.” – Chris Picciurro

Resources:

• Episode Sponsor: Wealth Builders Mortgage Group

• Teaching Tax Flow YouTube Channel

• Defeating Taxes Community

• (00:00) - Summary
• (00:00) - Exploring New Automobile Interest Deductions with Teaching Tax Flow
• (02:20) - New Tax Deduction for Qualified Automobile Loan Interest
• (09:29) - Understanding Tax Phase Outs and Their Impact on Deductions
• (15:41) - Understanding Vehicle Loan Interest Deductions and Tax Implications
• (21:12) - Exploring Tax Topics and Investment Advice on Teaching Taxable

For entrepreneurs, investors, and tax pros, Opportunity Zone Funds represent one of the most significant planning opportunities available — offering ways to defer capital gains, reduce taxes, and unlock tax-free growth. Jessica shares how these funds work, why they were introduced, and how business owners and investors can leverage them before key deadlines hit in 2026.

From real-world examples to industry insights, this episode highlights how QOZs can support economic development while also delivering powerful tax advantages.

What You’ll Learn:

• How Qualified Opportunity Zone Funds allow investors to defer and reduce capital gains taxes

• Why the program was created and which communities benefit most

• The timeline for Opportunity Zone deferrals (and why 2026 matters)

• Strategies for pairing QOZs with other tax planning tools

• Key industries — like hospitality and real estate — where QOZs have been most impactful

Key Insights:

QOZ Funds are more than just a tax break — they’re a strategic tool for reinvestment and growth. By rolling gains into qualified projects, investors can achieve tax-free appreciation while driving economic development in underserved areas.

Notable Quotes:

• “You are allowed to defer your capital gains into an Opportunity Zone Fund — and if held long enough, the appreciation can be tax-free.” – Jessica Correnti

• “Hospitality has been good because the zones are typically where they’re trying to drive revenue.” – Jessica Correnti

• “Ideas are cheap, but implementation is valuable.” – Chris Picciurro

Resources:

• Capital Square

• Teaching Tax Flow Hub

• DefeatingTaxes.com

• Teaching Tax Flow YouTube

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

• (00:00) - Summary
• (00:03) - Exploring Qualified Opportunity Zone Funds and Tax Benefits
• (04:05) - Exploring Tax Advantages of Opportunity Zone Funds
• (06:25) - Sports Allegiances and Personal Stories From Detroit to Nashville
• (07:29) - Exploring Tax Benefits of Opportunity Zone Funds
• (15:25) - Opportunity Zones 2.0: Permanent Benefits and Economic Impact
• (22:31) - Exploring Opportunity Zones and Resources with Jessica

What You’ll Learn:

• How OB3 permanently extends key provisions like QBI and restores 100% bonus depreciation

• Where Opportunity Zone Funds fit into an overall planning strategy

• SALT cap increases and how PTE workarounds can lower effective federal tax

• New and expanded credits (e.g., FICA tip credit expansion to beauty/service industries) and dependent care limits

• Practical, ethical strategy stacking to maximize deductions while staying compliant

Key Insights:

OB3 creates durable planning opportunities for small businesses—particularly those investing in equipment, real estate, or operating in high-tax states. Pairing QBI, bonus depreciation, and SALT strategy with OZ planning can materially change after-tax outcomes when implemented thoughtfully.

Notable Quotes:

• “What bonus depreciation is, is a provision that allows you to deduct the entire amount of asset purchase instead of writing it off over five, seven, or 15 years.” – Chris Picciurro

• “I think this is something that a lot of people are overlooking and we are going to lean into… in getting a special guest on to specifically talk about Opportunity Zone funds.” – Chris Picciurro

• “The people in our community, the teaching tax flow community, the voice of tax planning, by the way, drive our content, not us.” – Chris Picciurro

• “Now you could deduct if you’re married up to $40,000.” – Chris Picciurro (on SALT increases)

• “Ideas are cheap, implementation is valuable.” – Chris Picciurro

Resources:

• Teaching Tax Flow Website

• Teaching Tax Flow YouTube Channel
• OB3 Playlist

• Defeating Taxes

Episode Sponsor:

Sunsets & Dinks — premium pickleball apparel for the TTF community. Save 15% at teachingtaxflow.com/pickleball with code TTF15.

• (00:03) - Exploring OB3's Impact on Small Businesses and Pickleball Gear
• (01:44) - Exploring Tax Benefits for Small Business Owners
• (04:57) - Key Tax Benefits for Business Owners and Real Estate Investors
• (09:02) - Exploring Tax Strategies and Opportunities for Business Owners
• (14:14) - Tax Strategies for Business Owners in High Tax States
• (17:09) - The Value of Tax Planning and Professional Guidance
• (20:00) - New Tax Credits and Deductions for Employers and Employees
• (26:16) - Understanding IRS Guidance and Tax Planning Strategies

Many investors don’t realize that retirement funds can be used for much more than just stocks and mutual funds. Scott breaks down how self-directed IRAs open the door to real estate, private lending, startups, precious metals, and even cryptocurrency — all while maintaining tax advantages.

The conversation explores how these accounts work, what you can and can’t invest in, compliance requirements, and practical strategies for combining traditional IRAs with self-directed ones. Whether you’re an investor seeking greater control or a tax pro advising clients, this episode uncovers strategies that can maximize retirement wealth.

What You’ll Learn:

• What self-directed IRAs are — and what they are not

• How to diversify retirement funds into real estate, private companies, and more

• The rules for disqualified persons and prohibited transactions

• The difference between custodial and checkbook IRAs

• How to plan ahead for RMDs with illiquid assets

• Practical compliance requirements and why custodians matter

Key Insights:

Self-directed IRAs give investors control and flexibility, but with that freedom comes responsibility. From avoiding prohibited transactions to balancing liquidity for RMDs, Scott explains why working with a knowledgeable custodian is essential for both compliance and strategy.

Notable Quotes:

• “Most people don’t know it’s possible to invest in real estate or startups with their IRA — because their brokerage won’t tell them.” – Scott Maurer

• “Your IRA cannot transact with or benefit a disqualified person. That’s critical to know.” – Scott Maurer

• “Control is the number one benefit of a self-directed IRA.” – John Tripolsky

• “Ideas are cheap — implementation and compliance are what make the difference.” – Chris Picciurro

Resources:

• Advanta IRA

• Teaching Tax Flow Hub

• Join the Community: DefeatingTaxes.com

• Sunsets & Dinks Pickleball Apparel – teachingtaxflow.com/pickleball (Use code TTF15)

• (00:00) - Exploring Self-Directed IRAs and Pickleball Enthusiasm
• (01:59) - Exploring Self-Directed IRAs with Scott Maurer of Advanta IRA
• (06:13) - Exploring Self-Directed IRAs for Diverse Investment Opportunities
• (14:23) - Exploring Investment Opportunities in Self-Directed Retirement Accounts
• (19:03) - Navigating IRA Rules and Disqualified Persons in Investments
• (20:43) - Impact of Technology on Self-Directed Investments and Opportunities
• (24:26) - Navigating Self-Directed IRAs and Custodial Requirements
• (30:49) - Exploring Tax Strategies and Upcoming Content on YouTube

This special edition reflects on the show's evolution and highlights guest episodes that have delivered exceptional value on topics including real estate investing, tax strategies, IRS updates, financial planning, lending, bookkeeping, compliance, and more.

🎙️ EPISODES FEATURED:

#4 | Real Estate Spotlight (Panama City Beach, FL) – Crystal Ball
https://share.transistor.fm/s/b67de8c3

#6 | Lending Partners – Brenna M. Carles
https://share.transistor.fm/s/72fd8df4

#12 | REPS & Material Participation – Kirsten Limmer
https://share.transistor.fm/s/30d45fac

#14 | IRS Notices & Responses – Andrew Poulos
https://share.transistor.fm/s/60e885b3

#18 | Employee Retention Credit – Heidi Henderson / Stacy Deru
https://share.transistor.fm/s/871b18a4

#20 | Real Estate Spotlight (Fort Walton Beach, FL) – Heather Blatz
https://share.transistor.fm/s/87e104dc

#22 | Self-Directed IRAs – Scott Maurer
https://share.transistor.fm/s/de0be61d

#24 | R&D Credits – Heidi Henderson / Stacy Deru
https://share.transistor.fm/s/d647b847

#26 | Private Reinsurance / 831(b) – Roger Roundy
https://share.transistor.fm/s/639c5b84

#27 | Alt. Investments: Wildlife – Chris Gilroy
https://share.transistor.fm/s/78498cfd

#29 | Real Estate Spotlight (Nashville, TN) – Michael Gomez
https://share.transistor.fm/s/e331b511

#30 | Music & Money (Moon Taxi) – Trevor Terndrup / Tommy Putnam
https://share.transistor.fm/s/d1dd14c6

#32 | Legal Insight: STRs – Jeff Hampton
https://share.transistor.fm/s/d9721d5f

#38 | IRS War Stories – Andrew Poulos
https://share.transistor.fm/s/648fe7da

#42 | Mortgage Prep 101 – Brenna M. Carles
https://share.transistor.fm/s/b9f3f8d9

#43 | Money Tips for Teens – Dave Alger
https://share.transistor.fm/s/99e2828d

#47 | W-2 vs. 1099 – Jason Moll, CPA
https://share.transistor.fm/s/c90ffb07

#49 | How Taxes Are Made – LaShawn Thomas
https://share.transistor.fm/s/3f48c40d

#50 | Why Businesses Fail – Jon Neal
https://share.transistor.fm/s/7b2310c3

#62 | Cost Segregation Study – Heidi Henderson
https://share.transistor.fm/s/c55caa88

#66 | Corporate Transparency Act – Jeff Hampton
https://share.transistor.fm/s/e12eb0ea

#68 | 2024 IRS Update – Andrew Poulos
https://share.transistor.fm/s/96636666

#72 | Bookkeeping 101 – Lisa McCarthy
https://share.transistor.fm/s/583e56e0

#75 | 1099s Explained – Kaitlyn Rummel
https://share.transistor.fm/s/6fb268d7

#77 | STR Loophole – Arda Bircan
https://share.transistor.fm/s/a4411511

#80 | Payroll 101 – Will Lopez
https://share.transistor.fm/s/3d22a846

#83 | Long-Term Care Planning – Brooke Crane Acre
https://share.transistor.fm/s/e9d7f005

#85 | 1031 Exchange Update – Scott R. Saunders
https://share.transistor.fm/s/4dcdb380

#87 | Selling a Business – James Cunningham
https://share.transistor.fm/s/cadd8468

#89 | Real Estate Popularity – Bill Allen
https://share.transistor.fm/s/d62b171f

#95 | Deferred Sales Trusts – Todd Jackson
https://share.transistor.fm/s/68b88f2e

#99 | Corp. Transparency Act – Angelina Urquhart
https://share.transistor.fm/s/9baafa50

🎥 Video Episodes (YouTube):

#101 | Charitable Giving – Caden Gunnell
https://youtu.be/e2lvdeu4QZg

#104 | Credit Unions vs. Banks – Chrissy Siders
https://youtu.be/lRhT5uWDf_o

#107 | Business Life Cycles – Kelly Bender
https://youtu.be/uHPngp7E86g

#110 | Influencers & Taxes – Duke Alexander Moore
https://youtu.be/aomQ83WdueE

#112 | Capital Loss Harvesting – Alex Caswell / Colby Davis
https://youtu.be/W2LDZcS6t_M

#118 | Cannabis & Taxes – Kareyna Miller
https://youtu.be/4glCnI3uXWY

#121 | Farm Tax Benefits – Kelly Bender
https://youtu.be/Pcpq8h3S2xA

#125 | Delaware Statutory Trusts – Warren Thomas
https://youtu.be/PtQbZRIdeT4

#127 | Social Security – Robert D. Soerens
https://youtu.be/NvZ3srHbwAI

#129 | Estate Planning 101 – Court Pitcher
https://youtu.be/Ft0RIQrdpRU

#131 | Infinite Banking – Tom Laune
https://youtu.be/SIb-B61QV_4

#134 | Financing Property – Parker Borofsky
https://youtu.be/tW9xVRBw7aY

#137 | Digital Asset Reporting – Tynisa Gaines
https://youtu.be/fF9XbGfQ0N0

#140 | BRRRR Method – Jim Ingersoll
https://youtu.be/81NcN9hm7O8

#143 | Mindset + Money – Curtis McCollum
https://youtu.be/NpjN_ehtBdY

#145 | OB3 Bill: Real Estate – Scott R. Saunders
https://youtu.be/NYInhhFL0Eg

#148 | QSBS Exemption – Brady Weller
https://youtu.be/JwvchBIRVSU

⸻

RESOURCES:
• TTF Hub: https://www.teachingtaxflow.com/hub
• Defeating Taxes Community: https://www.defeatingtaxes.com

⸻

EPISODE SPONSOR:
Wealth Builders Mortgage Group
https://www.wealthbuildersmortgagegroup.com

As the team approaches their milestone 150th episode, they spotlight the value of moving from tax ideas to tax results by following a clear, repeatable process: Diagnose, Prescribe, IQ (Suitability) Test, and Implement. Through real-world examples and engaging analogies, Chris and John show how this approach creates tailored, effective strategies that minimize lifetime tax liability — legally and ethically.

What You’ll Learn:

• The four steps of the proprietary tax planning process and how each works

• Why knowing your marginal tax rate is the #1 KPI for tax planning

• How to determine the right prescription for your unique tax needs

• Common pitfalls when implementing tax strategies without suitability checks

• Why execution matters more than simply collecting ideas

Key Insights:

The same structured process works for every case, but the results are always unique. By diagnosing the current tax position, prescribing the right strategies, testing them for suitability, and then implementing them, taxpayers can avoid wasted effort and ensure their plans fit their circumstances.

Notable Quotes:

• “The process is the same for every case, but the results are always unique.”

• “Just because there’s four steps in this process doesn’t mean it necessarily has to take a long time.”

• “Implementation is key. Make some things you could self-implement like a health savings account…”

• “Your marginal tax rate is your number one KPI for your tax planning.”

• “Ideas are cheap, you can find them on TikTok, Instagram, etc. Implementation is valuable.”

Resources:

• Teaching Tax Flow Hub

Episode Sponsor:

Wealth Builders Mortgage Group

wealthbuildersmortgagegroup.com 

• (00:00) - Introduction and Episode Overview
• (00:46) - Episode Sponsor: Wealth Builders Mortgage Group
• (01:45) - Introduction to Chris and the Episode Topic
• (03:03) - Four-Step Tax Strategy Process Overview
• (05:45) - Step 1: Diagnose Your Tax Situation
• (09:15) - Step 2: Prescribe Tax Strategies
• (10:48) - Step 3: Suitability and IQ Testing
• (13:06) - Step 4: Implement the Strategy
• (15:34) - Conclusion and Community Engagement

If you’re a startup founder, business owner, or investor looking to optimize your exit strategy, this conversation could save you millions in taxes. Brady breaks down IRC Section 1202, explaining how the QSBS exemption allows eligible C Corporation shareholders to exclude up to $10 million (or 10x their basis) in capital gains from federal income tax.

The discussion also covers the QSBS rollover under IRC Section 1045, a strategy Brady likens to a “1031 exchange for company stock” — enabling sellers to reinvest gains into another qualified small business and defer taxes. The episode is packed with real-world applications, planning tips, and insight into recent legislative enhancements through the Inflation Reduction Act, which increased the QSBS exclusion cap and reaffirmed bipartisan support for innovation incentives.

Whether you’re preparing for a major exit or just learning about QSBS for the first time, this episode is a masterclass in how to use specialized tax planning to unlock significant wealth.

What You’ll Learn:

• How QSBS works and who qualifies

• The tax savings potential: $10M+ federal gain exclusion

• How the QSBS rollover under Section 1045 defers taxes

• Legislative updates that make QSBS even more attractive

• State-by-state considerations for QSBS eligibility

• Why early and specialized planning is critical for maximum benefit

Key Insights:

Brady Weller reveals how QSBS is often an untapped goldmine for founders — and why lack of awareness can mean leaving millions on the table. From structuring your business properly to timing exits and using rollovers, the right QSBS strategy can dramatically reshape your after-tax results.

Notable Quotes:

• “QSBS is one of the most powerful tax exemptions available, allowing federal income tax exemption on up to $10 million of gain.” – Brady Weller

• “We dreamed of creating an always available, downside-protected option for founders to execute these rollovers successfully.” – Brady Weller

• “OBBBA made QSBS even more powerful, expanding exclusion cap to $15 million, showing bipartisan support for this incentive.” – Brady Weller

• “QSBS and its rollovers provide a 1031-type tax deferral for company stock, fundamentally transforming tax planning strategies for many.” – Brady Weller

• “Our firm realizes around $3 billion in exit volume, emphasizing significant missed opportunities in the current system.” – Brady Weller

Resources:

• QSBS Rollover Website

• Connect with Brady Weller on LinkedIn

• Teaching Tax Flow

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

• (00:02) - Exploring Tax-Free Gains Through IRS Section 1202 QSBS
• (03:09) - Exploring Capital Gains Tax Mitigation with Brady Weller
• (05:19) - Exploring QSBS: A Powerful Yet Underutilized Tax Exemption
• (07:42) - Understanding Qualified Small Business Stock and Tax Exemptions
• (12:04) - Maximizing QSBS Benefits for Startup Founders Exiting Early
• (17:54) - Strategies for Starting or Acquiring a Business with QSPS Credit
• (19:36) - Understanding QSBS Rollovers and Tax Deferrals
• (21:15) - Navigating Related Party Rules in Business Exits
• (22:35) - The Future of QSBs and Tax Exclusions
• (24:37) - Exploring QSBS Rollover Benefits and Personalized Investment Advice
• (27:18) - Investment Offerings and Risk Factors in Financial Memorandums

Chris and John walk listeners through everything from retirement plan rollovers and benefit changes to withholding adjustments and self-employment considerations. They also tackle what you need to know about flexible spending accounts, health savings accounts, vested stock options, and group insurance benefits when leaving an employer. Wrapping up, the conversation shifts toward self-employment and retirement, covering key planning points like self-employment taxes, Social Security timing, and Medicare enrollment.

What You'll Learn:
• How to manage 401(k) rollovers and avoid penalties
• Why updating W-4 withholdings is crucial after a job change
• What to do about group life insurance and other employer benefits
• Key tax considerations for transitioning into self-employment
• Planning strategies for retirement income, Social Security, and relocation taxes

Key Insights:
Leaving a job involves more than just changes in pay; it requires proactive tax planning. Whether you’re switching employers or entering retirement, knowing these key steps can prevent costly surprises and help you navigate this major transition with confidence.

Notable Quotes:
• “I didn’t realize all of the considerations when you change jobs...that is a podcast episode.” – Chris Picciurro
• “Make sure your withholdings from your W-2 wages are proper.” – Chris Picciurro
• “Even if you have great life insurance through your employer, have coverage outside of your employment.” – Chris Picciurro
• “There are definitely some benefits for rolling it out of that former employer’s plan.” – Chris Picciurro
• “When you leave a job, there’s a lot more things to consider than just pay.” – Chris Picciurro

Resources:
• Teaching Tax Flow Website
• Defeating Taxes Facebook Group
• Teaching Tax Flow Hub
• Teaching Tax Flow YouTube Channel

Episode Sponsor:
Integrated Investment Group (IIG)
Wondering if you qualify as an accredited investor? Visit teachingtaxflow.com/iig to learn more.

• (00:02) - Tax Considerations When Changing Jobs or Retiring
• (05:36) - Managing Retirement Plans and Benefits When Changing Jobs
• (13:52) - Building a Non-Salesy Resource Hub for Tax Advice
• (15:09) - Tax Implications of Job Relocation and Stock Options
• (19:00) - Navigating Self-Employment Tax and Retirement Planning
• (24:19) - Alaskan Fishermen Deductions and Missed Opportunities
• (25:51) - Navigating Retirement Transitions and Financial Considerations
• (28:05) - Navigating Job Changes and Tax Implications

Chris introduces the Three Buckets of Tax Planning Implementations: behavioral strategies, tax-advantaged investments, and tax mitigation approaches. Together, they explore how each bucket impacts cash flow, tax flow, and duration—giving listeners an actionable blueprint for smarter financial decisions.

What You’ll Learn:

• The difference between tax compliance and tax planning

• How to leverage the three buckets of tax planning

• Why implementation partners matter just as much as strategy

• Real-world examples of behavioral strategies, tax-advantaged investments, and mitigation techniques

• How to systemize tax concepts to reduce overwhelm

Key Insights:

Tax planning isn’t just for the wealthy, it’s about creating intentional strategies that help you “own” your relationship with the IRS. By simplifying complex tax principles into digestible buckets, Chris and John make tax planning approachable, whether you’re a seasoned professional or just getting started.

Notable Quotes:

• “Ideas are cheap; implementation is valuable.”

• “Tax strategies don’t like to be single—they like to mingle, bundle, and stack.”

• “Having the wrong implementation partner could make you worse off than if you did nothing at all.”

• “Just because someone’s on TikTok doesn’t mean they can give accurate tax advice.”

Resources:

• Join the Defeating Taxes Community: DefeatingTaxes.com

• Teaching Tax Flow: teachingtaxflow.com

Episode Sponsor:

Reps Tracker

Get your special TTF discount at teachingtaxflow.com/reps and use code IFG.

• (00:00) - Exploring Tax Planning Strategies and Networking at Taxposium
• (05:27) - The Shift From Tax Compliance to Forward-Looking Tax Planning
• (10:45) - Effective Tax Planning Through Strategic Implementation and Partnerships
• (19:46) - Exploring Behavioral Tax Planning and Investment Strategies
• (27:22) - Engaging Tax Planning Discussions and Community Involvement

From 1031 exchanges and opportunity zones to bonus depreciation and estate tax updates, this episode dives deep into tax strategies that savvy investors can leverage immediately. If you’re in real estate—or advising clients who are—you won’t want to miss this breakdown of how OB3 brings long-term certainty and powerful new planning tools.

What You’ll Learn:

• Why OB3 is a major win for real estate investors

• How 1031 exchanges and carried interest survived untouched

• What the new $30M estate tax threshold means for your legacy

• How to stack bonus depreciation with 1031s

• The ongoing benefits of opportunity zones

Key Insights:

Scott explains how OB3 not only protects powerful real estate tools but also expands them. From permanent bonus depreciation to increased SALT deductions and renewed work-related income deductions, this bill sets the stage for years of opportunity in property investing.

Guest Spotlight:

Scott Saunders is a nationally recognized expert on 1031 exchanges and real estate tax strategies. As Senior Vice President of Asset Preservation Inc., he works with real estate professionals, investors, and lawmakers to shape smart policy and education around property taxation.

Practical Takeaways:

• Use 1031s to defer gains—and now pair them with permanent bonus depreciation

• Plan for generational wealth transfer under the new $30M estate tax limit

• Stack Opportunity Zones with other strategies for ultimate tax efficiency

• Real estate investments just got easier to plan—leverage the power of OB3

Resources:

• Teaching Tax Flow

• Asset Preservation Inc.

• Teaching Tax Flow YouTube Channel

• Join the community: DefeatingTaxes.com

Episode Sponsor:

Sunsets & Dinks Pickleball Apparel

Score 15% off at teachingtaxflow.com/pickleball with code TTF15

• (00:00) - Summary
• (00:00) - Exploring Real Estate Provisions in the One Big Beautiful Bill
• (04:15) - The Impact of Tax Certainty on Real Estate Investments
• (10:02) - Buc EE's Controversy in Palmer Lake, Colorado
• (11:01) - Real Estate Investment Benefits from Carried Interest and Estate Tax
• (12:37) - Estate Tax Implications on Real Estate and Liquidity
• (15:27) - Exploring Tax Strategies: 1031 Exchanges and Opportunity Zones
• (20:00) - Increased SALT Deduction Benefits New York Residents Until 2030
• (21:03) - Combining Bonus Depreciation and 1031 Exchange for Real Estate Gains
• (22:47) - Positive Economic Impact of New Real Estate Tax Incentives
• (25:51) - Insights on Tax, Economics, and Real Estate Strategies

What You’ll Learn:

• How OB3 makes many TCJA provisions permanent

• What’s changing with the Child Tax Credit and how it affects your refund

• New deductions for overtime pay and tip income

• Why the SALT deduction cap increase is a big win for high-tax states

• What “Trump Accounts” are and how they could shape your child’s financial future

Key Insights:

Chris Picciurro highlights the lasting impact of OB3 on everyday tax planning. From expanded standard deductions to new tax benefits for families and workers, this episode is a must-listen for anyone navigating the new tax landscape in 2025 and beyond.

Practical Takeaways:

• Use the increased $2,200 Child Tax Credit to boost your refund potential

• Plan ahead if you’re in a high-tax state—the $40,000 SALT deduction cap can dramatically shift your strategy

• Deduct up to $25,000 in cash tips and leverage new vehicle loan interest rules

• Learn how “Trump Accounts” might offer automatic contributions for your child

Resources:

• Wealth Builders Mortgage Group: wealthbuildersmortgagegroup.com

• Explore more episodes at TeachingTaxFlow.com

• Join the Defeating Taxes Facebook Group: DefeatingTaxes.com

• Watch full episodes on our YouTube Channel

Episode Sponsor:

Wealth Builders Mortgage Group

Visit wealthbuildersmortgagegroup.com and mention Teaching Tax Flow for personalized mortgage guidance from trusted professionals.

• (00:02) - Exploring the One Big Beautiful Bill Act's Impact
• (06:16) - Tax Cuts and Benefits for Families Under OB3
• (13:34) - New Tax Deductions and Their Impact on Taxpayers
• (22:08) - Introducing Trump Accounts and Expanded 529 Plan Flexibility
• (23:41) - Tax Changes and Their Impact on Future Financial Planning

What You'll Learn:
• Why 95% of your behavior is driven by subconscious programming from ages 0-5
• How limiting beliefs about money sabotage your financial success
• The difference between conscious goals and subconscious resistance
• Why "success is hard" programming keeps you stuck
• How to identify and eliminate financial blind spots

Key Insights:
Curtis shares his breakthrough, discovering that a belief formed at age 2 ("success is hard and difficult") was sabotaging his million-dollar financial services career. Learn how beliefs like "money don't grow on trees" or "tax planning is only for rich people" create invisible barriers to wealth building.

Guest Spotlight:
Curtis McCullom brings 40+ years of financial services experience plus expertise in transformational coaching. He specializes in helping entrepreneurs and high achievers eliminate childhood programming that limits their success.

Practical Takeaways:
• Question limiting beliefs: "Is this true for everyone?"
• Guard your mindset daily - it's not a one-and-done fix
• Recognize that you have all the resources within you to succeed
• Address the baggage before implementing financial strategies

Resources:
Find a tax professional at www.2025.tax

Episode Sponsor:
Legacy Lock
Book a 30-minute complimentary discovery session at teachingtaxflow.com/legacy
(Mention Teaching Tax Flow for special pricing)

• (00:00) - Exploring Money Mindset with Curtis McCollum
• (04:54) - Transformative Journeys and Mindset Shifts for Personal Growth
• (08:02) - Subconscious Beliefs Impact Financial Responsibility and Mindset
• (13:37) - Mindset, Money, and Overcoming Fear of Financial Control
• (15:30) - Identifying and Overcoming Blind Spots in Personal Growth
• (16:38) - Uncovering Subconscious Beliefs That Sabotage Success
• (20:15) - Overcoming Financial Roadblocks Through Mindset and Awareness
• (26:45) - Clearing Mental Baggage for a Focused and Agile Mindset
• (31:25) - Unlocking Personal Growth Through Self-Awareness and Tax Education
• (36:21) - Investment Advice and Legal Disclaimers for Financial Services

Join hosts Chris Picciurro, CPA and John Tripolsky as they shine a light on the "cockroach taxes" that hide in the dark - those sneaky hidden taxes that have nothing to do with your income level but can significantly impact your wallet.

What You'll Learn:
• The #1 hidden tax affecting everyone: Sales tax (45 states + DC)
• How travel industry taxes can add 40% to your booking costs
• Franchise and excise taxes for business owners
• Real estate transfer taxes that hit even loss transactions
• "Sin taxes" on alcohol and cigarettes with shocking state variations
• Hotel occupancy and rental car taxes that inflate travel costs

Key Takeaways:
Hidden taxes are non-income based taxes you pay without filing returns. From California's $800 LLC fee to New York's $4.35 per pack cigarette tax, these taxes can add thousands to your annual expenses. Learn which states have the highest burdens and how to plan around them.

Eye-Opening Examples:
• Florida's 0.7% real estate transfer tax on ALL property sales
• New York cigarette taxes costing smokers $1,500+ annually
• Hotel taxes adding 15% to your lodging costs
• Ticketmaster-style "convenience fees" of 25-35%

Resources:
Find a tax professional at www.2025.tax

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

• (00:00) - Uncovering Hidden Taxes and Their Impact on Your Wallet
• (03:31) - Hidden Taxes: Sales, Travel, and Franchise Fees Explored
• (07:37) - Californians Moving and Making Friends in Franklin Tennessee
• (08:05) - Understanding Real Estate Transfer Taxes and Their Implications
• (12:31) - Exploring Sin Taxes and Their Impact on Consumption
• (19:05) - Exploring Local Tax Initiatives and Community Engagement

What You'll Learn:
• Who pays gift tax (spoiler: it's not who you think!)
• The 2025 annual gift tax exclusion of $19,000 per recipient (2024 = $18,000)
• How married couples can strategically gift up to $36,000 per recipient
• Why gifting appreciated assets is usually a bad idea
• Smart strategies for wedding expenses and family financial support
• Advanced planning with 529 super-funding and valuation discounts

Key Takeaways:
The donor (gift giver) pays any gift tax and files returns, not the recipient. Most gift tax returns are informational only, with no actual tax owed. Learn practical strategies, such as timing gifts across tax years and paying tuition or medical expenses directly to providers, to avoid gift tax implications entirely.

Advanced Strategies Covered:
• 529 plan super-funding up to $95k per beneficiary in 2025 (2024 = $90k)
• Valuation discounts for closely-held businesses
• Gift splitting for married couples
• Estate tax planning considerations

Resources:
Find a tax professional at www.2025.tax
Join/Comment > www.DefeatingTaxes.com

Episode Sponsor:
Integrated Investment Group

www.integratedig.com

• (00:00) - Understanding Gift Taxes and Their Impact on Financial Success
• (02:32) - Understanding Gift Tax and Estate Planning Strategies
• (09:54) - Gift Tax Strategies and Planning Opportunities for Families
• (18:10) - Advanced Gift Tax Strategies and Estate Planning Insights
• (23:17) - Crocheting Business Success and Gifting Tax Implications

Join Jim Ingersoll from Deal Maker as he breaks down the powerful BRRRR strategy (Buy, Rehab, Rent, Refinance, Repeat) for real estate investors. Learn how to leverage other people's money, maximize tax advantages, and build wealth through strategic property investment.

KEY TAKEAWAYS:
• BRRRR Method: Buy, Rehab, Rent, Refinance, Repeat strategy breakdown
• Start with refinancing in mind and work backwards for better results
• Community networking is crucial for real estate investment success
• Being an employee creates the highest tax burden vs. real estate investing
• Creative financing strategies using other people's money (OPM)

EPISODE BREAKDOWN:
- Jim's Journey from Corporate America to Real Estate
- BRRRR Method Step-by-Step Implementation
- Tax Advantages of Real Estate Investment Strategies
- Leveraging Other People's Money for Growth
- Building Your Real Estate Investment Community
- Creative Financing Techniques That Work

GUEST EXPERT:
Jim Ingersoll
Deal Maker Founder
jim@elitedealmakers.com
- Nearly two decades in real estate investing
- Expert in wholesaling, flipping, and rental properties
- Founder of educational events attracting thousands of investors
- Specialist in collaborative real estate strategies

SPONSORED BY:
Wealth Builders Mortgage Group
Specialized lending for real estate investors
wealthbuildersmortgagegroup.com

Chris and John break down essential tax strategies for business owners earning over $150,000 annually. Learn how to legally reduce your tax burden and keep more of your hard-earned income through proven planning techniques.

KEY TAKEAWAYS:
• Why $150K is the strategic planning threshold for business owners
• Home office deduction: Your gateway to deductible business miles
• Retirement plan contributions: Keep your money while reducing taxes
• Income shifting strategies for family members
• S-Corp election: When the pizza buffet analogy makes sense

EPISODE BREAKDOWN:
• Understanding Marginal Tax Rate vs. Tax Brackets
• Behavioral Tax Strategies (No Additional Cost Required)
• Home Office Deduction Benefits & Requirements
• Retirement Planning for Business Owners
• Family Income Shifting Opportunities
• S-Corporation Election: Pros, Cons & Pizza Buffets
• Advanced Strategies for $500K+ Earners

BEHAVIORAL STRATEGIES COVERED:
• Home office deduction optimization
• Strategic retirement contributions
• Family member employment planning
• Proper record keeping and tracking

DON'T FORGET... Here's our favor to ask of you
Step #1 - Subscribe to our YouTube Channel
Step #2 - Join our private Facebook Group
Step #3 - Visit the TTF HUB

Also, check this out, "Teaching Tax Flow LIVE: Tax Strategies for $150K+ Business Owners"

SPONSORED BY:
Reps Tracker
Special TTF discount at https://www.teachingtaxflow.com/reps
Use code IFG for a discount!

• (00:02) - Tax Strategies for Business Owners Earning Over $150,000
• (10:02) - Maximizing Tax Benefits with Home Office Deductions
• (12:57) - Behavioral Strategies for Retirement Plan Contributions and Tax Savings
• (15:08) - Tax Efficiency Through Income Shifting and Strategic Planning
• (21:27) - Understanding S Corp Elections Through a Pizza Buffet Analogy
• (24:15) - Tax Strategies and Compliance for High-Income Earners
• (29:36) - Tax Planning Resources and Community Engagement

Chris and John dive into the evolving landscape of tax preparation, examining the critical challenges facing the industry and its implications for both taxpayers and professionals.

KEY TAKEAWAYS: 

• 75% of CPAs expected to retire within 15 years 
• 37% drop in CPA exam candidates since 2016 
• Rising complexity meets compressed deadlines 
• AI adoption is accelerating across tax firms 
• Compliance-only firms are becoming obsolete

EPISODE BREAKDOWN:

• The Great CPA Shortage: Numbers Don't Lie
• Technology Evolution: From Paper to AI
• Why Tax Returns Are Getting More Complex
• How AI is Transforming the Industry
• The Future of Tax Professional Services
• What Taxpayers Need to Know

INDUSTRY INSIGHTS:

• Offshore outsourcing trends
• Value-based billing models
• The importance of year-round advisory services
• How to choose the right tax professional

SPONSORED BY:
Sunsets and Dinks Pickleball Gear
Use code TTF15 for 15% off at teachingtaxflow.com/pickleball

• (00:00) - Exploring the Future of the Tax Preparation Industry
• (02:08) - The Evolution and Challenges of the Tax Preparation Industry
• (10:51) - The Importance of Personal Responsibility in Dental Health
• (12:03) - Geese, Swans, and Tax Planning Adventures
• (14:51) - Addressing CPA Shortages and Industry Challenges
• (17:51) - Challenges and Delays in the Tax Preparation Industry
• (22:29) - The Rising Complexity and Challenges of Tax Preparation
• (28:32) - AI's Impact on Tax Professionals and the IRS
• (32:04) - Evolving Tax Practices: From Compliance to Advisory Models
• (39:00) - Exploring Opportunities and Challenges in the Tax Industry

Join tax expert Tynisa "Ty" Gaines, EA, as she breaks down the essentials of cryptocurrency and digital asset tax reporting. Learn how the IRS views digital assets, when transactions are taxable, and how to prepare for upcoming reporting requirements.

KEY TAKEAWAYS:
• Digital assets are treated as property by the IRS, not as currency 
• Every sale, trade, or purchase using cryptocurrency creates a taxable event 
• Cost basis tracking is critical - without it, the IRS assumes zero basis 
• New 1099-DA reporting forms are coming for tax year 2025 
• Even "innocent" transactions like buying coffee with crypto must be reported

EPISODE BREAKDOWN:

• How Digital Assets Are Classified for Tax Purposes
• Common Reporting Mistakes Taxpayers Make
• Cost Basis Tracking Methods and Best Practices
• Understanding the New 1099-DA Form Requirements
• Special Considerations for Business Owners Accepting Crypto

SPONSORED BY:
Wealth Builders Mortgage Group
Visit wealthbuildersmortgagegroup.com for specialized lending strategies for investors

• (00:02) - Exploring IRS Treatment of Digital Assets with Expert Ty Gaines
• (05:25) - From Military Spouse to Digital Asset Tax Professional
• (08:25) - University Rivalries, Military Education, and Campus Visits
• (11:33) - Tax Reporting for Digital Assets and Cryptocurrency Transactions
• (14:09) - Tracking Crypto Cost Basis and Tax Reporting Responsibilities
• (18:48) - Tax Implications of Cryptocurrency Transactions and Market Volatility
• (22:29) - Understanding New 1099 DA Reporting Requirements for Digital Assets
• (25:03) - Navigating Tax Forms with Humor and Professional Guidance

Join Chris Picciurro, CPA, and John Tripolsky as they explain the so-called "Venmo Tax" and how third-party payment platforms will impact your tax reporting. Learn about the changing thresholds for 1099-K forms and what everyday Venmo users need to know.

KEY TAKEAWAYS: 

• 2025 Threshold: Only $2,500 in transactions triggers a 1099-K form 
• 2026 Threshold: Set to drop further to just $600 
• Taxable vs. Non-Taxable: Not all Venmo transactions are taxable income 
• Common Triggers: Splitting bills, group purchases, and gifts can all generate forms 
• Handling Incorrect 1099-Ks: How to properly report forms received in error

EPISODE BREAKDOWN:

• Understanding Third-Party Settlement Organizations (TPSOs)
• The Changing 1099-K Thresholds (2023-2026)
• Which Transactions Are Actually Taxable
• Everyday Examples That Can Trigger Forms
• How to Handle Incorrect 1099-K Forms

SPONSORED BY:
Legacy Lock
Visit teachingtaxflow.com/legacy for easy estate planning from home

• (00:00) - Understanding IRS Rules for Venmo and Similar Platforms
• (04:33) - Understanding the Implications of the Venmo Tax
• (09:58) - The Rise of Digital Payments and Their Everyday Impact
• (13:41) - Understanding 1099-K Threshold Changes and Their Implications
• (15:27) - Understanding 1099K Reporting for Personal and Business Transactions
• (21:07) - The Impact of Cashless Transactions on Tax Filing Complexity
• (21:08) - Handling 1099K Errors in Personal Transactions
• (22:46) - The Complexities of Tax Reporting and Financial Advice

KEY TAKEAWAYS:
• December 31st Rule: Your year-end status determines your filing status
• Five Filing Statuses Explained: Single, Married Filing Jointly, Married Filing Separately, Head of Household, Qualifying Surviving Spouse
• Marriage & Taxes: Joint vs. Separate Filing Implications
• Head of Household Benefits & Qualifications
• Special Considerations for Divorce & Alimony

EPISODE BREAKDOWN:
- Understanding Filing Status Options
- Tax Bracket Differences by Status
- When to Choose Married Filing Separately
- Head of Household Requirements
- Post-Divorce Tax Considerations

SPONSORED BY:
Integrated Investment Group (IIG)
Visit www.teachingtaxflow.com/iig to learn if you qualify as an accredited investor

• (00:00) - Impact of Filing Status on Tax Returns
• (03:28) - Understanding Tax Implications of Different Marital Statuses
• (08:31) - Tax Filing Statuses: Joint vs. Separate for Married Couples
• (15:02) - Understanding Head of Household and Qualifying Surviving Spouse Statuses
• (20:35) - Tax Strategies for Married Couples and Withholding Adjustments
• (21:51) - Cupid's Boomerang and Stage Banter
• (22:42) - Tax Implications of Divorce and Alimony Under New Laws
• (23:47) - Love, Taxes, and Life's Different Filing Statuses
• (25:12) - Tax Advice and Caution for Financial Decisions