Join hosts Chris Picciurro, CPA, and John Tripolsky as they welcome transformational coach Curtis McCullom to explore the powerful connection between mindset and money. Discover how childhood programming shapes your financial decisions and learn to overcome the invisible barriers holding you back.

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

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

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

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
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

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

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

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

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