Teaching Tax Flow: The Podcast

By Chris Picciurro and John TripolskyBusiness Education

Teaching Tax Flow: The Podcast episodes

July 01, 2025Ep. 142 | Hidden Taxes Exposed
Episode 142: Hidden Taxes Exposed - The Taxes You Don't See Coming
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
21 min
June 24, 2025Ep. 141 | Gift Taxes 101
Join hosts Chris Picciurro, CPA, and John Tripolsky as they break down the often-confusing world of gift taxes in this comprehensive Gift Tax 101 episode.
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
26 min
June 17, 2025 Ep. 140 | BRRRR Method Explained
Master the BRRRR Method: Real Estate Investing Strategy Explained | Teaching Tax Flow Ep. 140
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
[email protected]
- 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
33 min
June 10, 2025Ep. 139 | Keep More of Your $150K+ Business Income
Keep More of Your $150K+ Business Income: Tax Strategies That Work | Teaching Tax Flow Ep. 139
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
35 min
June 03, 2025Ep. 138 | The Future of The Tax Prep Industry
The Future of the Tax Prep Industry: Challenges & Opportunities | Teaching Tax Flow Ep. 138
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
44 min
May 27, 2025Ep. 137 | Digital Asset Reporting 101
Digital Asset Reporting 101: What You Need to Know | Teaching Tax Flow Ep. 137
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
28 min
May 20, 2025Ep. 136 | Unpacking the Venmo Tax
Unpacking the Venmo Tax: What You Need to Know for 2025
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
25 min
May 13, 2025Ep. 135 | Love, Taxes, and Filing Status
Join Chris Picciurro, CPA, and John Tripolsky as they discuss how your relationship status affects your tax situation. Learn about the five filing statuses and how each impacts your tax liability, deductions, and credits.
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
27 min
May 06, 2025Ep. 134 | Financing Your Second Property (Taxes & Mortgage)
Financing Your Second Property: Tax & Mortgage Strategies | Teaching Tax Flow Ep. 134

Join Chris Picciurro, John Tripolsky, and special guest Parker Borofsky, Branch Leader at Wealth Builders Mortgage Group, as they dive into the intricate relationship between mortgages and taxes when financing a second property. Learn from Parker's expertise in both mortgage lending and short-term rental investing.
KEY TAKEAWAYS:
• Different Types of Mortgages: QM vs Non-QM Loans
• Down Payment Requirements: From 10% Second Home to 20% Investment
• Tax Implications of Property Usage
• Refinancing Strategies and Break-Even Points
• VA Loan Options for Second Properties
GUEST EXPERT:
Parker Borofsky
- Branch Leader, Wealth Builders Mortgage Group
- Short-term Rental Property Investor
- Closed over $1.1B in short-term rental loans
EPISODE BREAKDOWN:
- Understanding Second Home vs. Investment Property
- Mortgage Options and Requirements
- Tax Considerations for Different Property Uses
- When to Consider Refinancing
- Tips for Mortgage Application Success
SPONSORED BY:
REPStracker
www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)
(00:02) - Financing Second Homes and Tax Implications
(04:40) - From Timeshare Marketing to Thriving in Short-Term Rentals
(09:12) - Tax Implications and Loan Options for Second Property Buyers
(14:47) - Understanding Qualified and Non-Qualified Mortgage Options
(18:20) - Strategies for Refinancing and Buying Second Properties
(26:43) - Navigating Mortgage Challenges with Expert Guidance
(34:31) - Exploring Tax Strategies and Financial Advice on YouTube
37 min
April 29, 2025Ep. 133 | Beyond the Blackboard: Teachers & Taxes
Beyond the Blackboard: Teachers & Taxes | Teaching Tax Flow Ep. 133
Join Chris Picciurro, CPA, and John Tripolsky as they break down essential tax strategies specifically for educators. Discover five game-changing tax benefits that every teacher should know about, from classroom expense deductions to retirement planning strategies.
KEY TAKEAWAYS:
• Educator Expense Deduction: Up to $300 ($600 for married teaching couples) for classroom supplies
• Student Loan Interest Deduction: Maximum $2,500 annual deduction
• Lifetime Learning Credit: Up to $2,000 for continuing education
• Roth Contribution Strategies for Early-Career Teachers
• HSA Benefits: The "stealth retirement account" educators should consider
EPISODE BREAKDOWN:
- Special Tax Benefits for Teachers
- Early Career Financial Planning
- Retirement Account Strategies
- Healthcare Savings Opportunities
- Education Credits & Deductions
RESOURCES:
• Visit teachingtaxflow.com for more tax insights
• Join the Defeating Taxes Facebook Group
• Teaching Tax Flow Hub
SPONSORED BY:
Sunsets & Dinks
Use discount code TTF15
(00:00) - Teachers, Taxes, and Pickleball Enthusiasm
(01:34) - Balancing Holiday Traditions with Their True Meaning
(03:44) - Empowering Teachers with Tax Planning and Financial Awareness
(08:57) - Lifelong Learning and Saved by the Bell Nostalgia
(11:11) - Tax Deductions and Credits for Teachers
(19:08) - Tax Strategies and Financial Advice for Teachers
26 min

About Teaching Tax Flow: The Podcast

From the publisher's feed

Welcome to “Teaching Tax Flow: The Podcast”, the show that’s all about demystifying taxes and helping you keep more of your hard-earned income in your pocket.