Teaching Tax Flow: The Podcast

In this Episode of the Teaching Tax Flow Podcast, hosts Chris and John are joined by Jeremy Wells, PhD, CPA, EA, to unravel one of the most misunderstood areas in tax strategy — Material Participation.

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 busine...

In this episode of the Teaching Tax Flow Podcast, hosts Chris Picciurro, CPA, and John Tripolsky revisit a familiar favorite — the Limited Liability Company (LLC). Whether you’re forming your first entity or restructuring an existing one, this episode walks through the essential steps of creating and maintaining an LLC — while busting myths about tax benefits, compliance, and liability protection.

Chris explains why an ...

In this episode of the Teaching Tax Flow Podcast, hosts Chris Picciurro, CPA, and John Tripolsky welcome Marit Burmood, CPA & EA, to discuss actionable strategies for business owners as the year winds down. From vehicle deductions to timing income and expenses, this episode cuts through online tax myths to deliver real-world guidance on maximizing deductions before year-end.

Marit shares practical insight from years of ...

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky dig into the newly released 2024 IRS Data Book. With 94 pages of charts, stats, and enforcement trends condensed into an engaging discussion, this episode reveals how the IRS operates and what taxpayers should know.

From audit rates to revenue collection, Chris and John provide context for business owners, individuals, and tax pro...

In Episode 154 of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky rev up a discussion on one of the most surprising new provisions from the One Big Beautiful Bill Act (OB3): a personal tax deduction for qualified automobile loan interest.

Chris and John break down how this above-the-line deduction works, the criteria for qualifying, and the potential pitfalls for taxpayers. From vehicle req...

In Episode 153 of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky welcome Jessica Correnti from Capital Square to unpack the power and potential of Qualified Opportunity Zone (QOZ) Funds.

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 ta...

Welcome to Episode 152 of the Teaching Tax Flow podcast! Co-hosts Chris Picciurro, CPA and John Tripolsky break down how the One Big Beautiful Bill Act (OB3) reshapes the landscape for small business owners—covering everything from the QBI deduction and 100% bonus depreciation to Opportunity Zones, SALT planning, and new credits for employers and employees. Sponsored by Sunsets & Dinks, this episode gives entrepreneurs...

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky welcome back Scott Maurer, VP at Advanta IRA, to take a deep dive into the world of self-directed IRAs.

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 met...

In Episode 150 of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky celebrate a major milestone—150 episodes of empowering listeners with actionable insights in tax, finance, and business.

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 planni...

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky break down the 4-Step Tax Planning Implementation Process — the same proprietary framework used in Chris’s CPA practice and within Teaching Tax Flow.

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, Presc...

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro, CPA, and John Tripolsky welcome Brady Weller, co-founder of QSBS Rollover, to explore one of the most powerful — and most overlooked — tax planning tools for entrepreneurs: the Qualified Small Business Stock (QSBS) exemption.

If you’re a startup founder, business owner, or investor looking to optimize your exit strategy, this conversation could sav...

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 benefi...

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 th...

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 estat...

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...

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 a...

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 ...

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 i...

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, ...