Join hosts Chris Picciurro, CPA, and John Tripolsky as they explore an often-overlooked topic: the tax implications of changing jobs or transitioning into retirement. With career changes on the rise in recent years—whether due to new opportunities, layoffs, or retirement—understanding the tax side of employment transitions is crucial.

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

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky break down how proactive tax planning can help you take control of your financial future. Fresh off their visit to NATP’s Taxposium in Las Vegas, they explore the critical differences between tax compliance and forward-looking tax planning, providing a clear framework for implementing powerful strategies.

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

Join hosts Chris Picciurro, CPA, and John Tripolsky as they welcome back Scott Saunders, Senior Vice President at Asset Preservation Inc., to unpack how the One Big Beautiful Bill Act (OB3) impacts real estate investors.

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

Join hosts Chris Picciurro, CPA, and John Tripolsky as they unpack the sweeping changes introduced by the newly enacted One Big Beautiful Bill Act (OBBBA or OB3). This 1,100-page piece of legislation is one of the most impactful tax updates in recent years, and this episode breaks it down into digestible, actionable insights for individual taxpayers.

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

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

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

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

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

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

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