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 O...
Jul 22, 2025•28 min
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 ...
Jul 15, 2025•29 min
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 g...
Jul 08, 2025•37 min
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...
Jul 01, 2025•21 min
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 sup...
Jun 24, 2025•26 min
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 backwar...
Jun 17, 2025•33 min
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...
Jun 10, 2025•34 min
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 be...
Jun 03, 2025•43 min
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 ...
May 27, 2025•27 min
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 ...
May 20, 2025•25 min
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 ...
May 13, 2025•27 min
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...
May 06, 2025•36 min
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,...
Apr 29, 2025•25 min
In this episode of the Teaching Tax Flow podcast, John and Chris jump into the details of the Retirement Savings Contributions Credit, commonly known as the Saver's Credit. Throughout the discussion, they share valuable insights into how this federal tax credit benefits taxpayers, particularly those with low to moderate income, by encouraging them to save for retirement. The Saver's Credit can significantly impact your financial health by offering up to a $2,000 tax credit for married couples fi...
Apr 22, 2025•27 min
Episode Guest: Tom Laune Tom Laune is an experienced financial advisor and nationally recognized speaker specializing in infinite banking and financial strategies. With a unique background as a recording engineer for top musical artists like Bruce Springsteen and Aretha Franklin, Tom transitioned into the financial sector after a pivotal personal experience with a disability policy. He has since gathered numerous financial designations, including being an authorized infinite banking practitioner...
Apr 15, 2025•35 min
Episode 130 focuses on dismantling the myth that filing for a tax extension is negative or indicative of a financial faux pas. Instead, the hosts reveal how a tax extension can serve as a powerful tax planning tool, particularly useful for business owners and real estate investors. Chris passionately explains why tax extensions should not be feared but embraced to ensure accurate and optimal tax filing. With an emphasis on complex tax returns, the episode highlights reasons to file an extension,...
Apr 08, 2025•25 min
About the Guest: Court Pitcher Court is a seasoned expert in estate planning, currently serving as a key member of Legacy Lock, a company offering comprehensive estate planning solutions. With a career spanning over two decades, Court was driven into the estate planning field after personal experiences highlighted the criticality of having a solid estate plan. Recognizing the gaps in traditional estate planning services, he co-founded Legacy Lock to provide accessible and comprehensive estate an...
Apr 01, 2025•36 min
In Episode 128 of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky about the top five tax hacks for real estate investors. Known for his dynamic approach to tax strategies, Chris elaborately discusses the importance of proactive tax planning. He emphasizes that, whether you're a seasoned investor or just starting out, these strategies not only serve investors with direct benefits but can also be adapted by those not yet fully immersed in real estate investments. John, with...
Mar 25, 2025•24 min
Episode Guest: Rob Soerens Rob is a financial advisor with Gateway Financial Advisors, holding over a decade of experience in the financial industry. Prior to his current role, Rob practiced as an attorney specializing in mergers and acquisitions, tax law, and estate planning. Transitioning from law to financial advising, Rob's expertise spans across investment strategies, retirement planning, and social security benefits. His vast knowledge and practical experience provide valuable insights, es...
Mar 18, 2025•34 min
In episode 126 of the Teaching Tax Flow podcast, hosts John Tripolsky and Chris Picciurro break down the intricacies of Required Minimum Distributions (RMDs), a mandatory withdrawal policy associated with certain retirement accounts. Initially introduced under the Revenue Act of 1978, RMDs dictate that account holders aged 73 and above must withdraw a specified amount from their tax-deferred accounts to ensure that money enters the taxable revenue stream. As tax laws evolve, understanding these ...
Mar 11, 2025•24 min
About the Guest: Warren Thomas Warren Thomas is a distinguished expert in real estate taxation and investment, known for his extensive background and expertise in Delaware Statutory Trusts (DSTs) and 1031 exchanges. With a career that began as a CPA and auditor at Ernst and Young, he founded his own successful CPA firm in Southern California, focused on small business and tax matters. Currently, Warren is a co-founder of ExchangeRight, a leading firm in the DST space, known for its significant g...
Mar 04, 2025•31 min
Welcome to Episode 124 of the Teaching Tax Flow podcast, where hosts John Tripolsky and Chris Picciurro wrap up their informative series on tax schedules with a deep dive into Schedule E. This episode is sponsored by Integrated Investment Group, inviting accredited investors to explore new financial opportunities. They kick off the discussion by examining the nuances of Schedule E, a pivotal form for reporting rental income and expenses on personal tax returns. Chris emphasizes why treating your...
Feb 25, 2025•25 min
Welcome to Episode 123 of the Teaching Tax Flow Podcast, where hosts John Tripolsky and Chris Picciurro delve into part two of their insightful three-part series focused on Schedule C, a crucial element of the Form 1040. This episode is designed to shed light on the intricacies of reporting profit and loss for sole proprietors, freelancers, and gig economy workers through Schedule C. With expert guidance, you'll learn how this form plays a vital role in tax compliance and strategy, specifically ...
Feb 18, 2025•27 min
In this episode of the Teaching Tax Flow Podcast, hosts Chris Picciurro and John Tripolsky look into the intricate world of Schedule A of Form 1040, unraveling its layers for taxpayers. This episode marks the beginning of the ACE series, an educational journey exploring Schedules A, C, and E, to aid the community in leveraging tax schedules effectively. Supported by relentless enthusiasm, Chris and John guide listeners through the nuances of itemized deductions, offering clarity on common deduct...
Feb 11, 2025•25 min
About the Guest: Kelly Bender Kelly is a seasoned accountant with extensive expertise in agricultural taxation. She owns a thriving accounting practice based in Pennsylvania and is deeply embedded in the farming community both professionally and personally. Alongside her husband, Kelly manages a farm that raises various animals and crops, giving her first-hand experience with the unique financial intricacies faced by those in agriculture. Her diverse background combines a rich understanding of t...
Feb 04, 2025•35 min
In this episode of the "Teaching Tax Flow Podcast," hosts Chris Picciurro and John Tripolsky jump into the compelling topic of whether or not to elect S Corporation status for your business. The episode, titled "Should I Be An S Corp?" navigates the complexities surrounding this pivotal business tax decision. Kicking off with how S Corp status can significantly impact your tax liabilities, Chris and John share insights into when this election may be favorable and when it might be detrimental. Le...
Jan 28, 2025•27 min
In this episode of the Teaching Tax Flow podcast, hosts John Tripolsky and Chris Picciurro jump into the crucial tax filing updates for 2024, making sure listeners are well-prepared for the new tax season. With their signature blend of insightful advice and engaging banter, the hosts explore the potential impact of both current and anticipated changes to U.S. tax laws. Listeners who tune in to this engaging discussion will gain essential insights into the nuances of the Tax Cuts and Jobs Act adj...
Jan 21, 2025•23 min
About the Guest: Kareyna Miller Kareyna is a Michigan-based Certified Public Accountant (CPA) noted for her expertise in the cannabis industry. She has been practicing since 2011 and entered the cannabis sector in 2016. Kareyna is highly regarded for her knowledge in cannabis-related tax and accounting compliance and is recognized as an authority in handling the complex issues surrounding cannabis industry taxes and financial attestations. She actively participates in educational initiatives for...
Jan 14, 2025•29 min
In this episode of the Teaching Tax Flow Podcast, co-hosts Chris Picciurro and John Tripolsky dive into actionable personal and business goal-setting strategies for 2025. Recognizing the universal desire to start anew each January, they challenge both individuals and business owners to think beyond the typical New Year’s resolutions. Instead of letting Quitters Day—the second Friday of January—mark the end of ambitions, they encourage listeners to sustain their momentum throughout the year. Chri...
Jan 07, 2025•29 min
In this final podcast episode of 2024, Chris and John explore the " Taxpayer Timeline ," equipping listeners with vital insights into the tax calendar year. They unravel the complexities of tax deadlines, clarifying essential dates for individuals and small business owners. As the year draws to a close, they ensure you're poised to enter 2025 with enhanced tax savvy. Sponsored by The Mortgage Shop , the episode extends gratitude to dedicated listeners and their community. Navigating the tax time...
Dec 31, 2024•18 min
