Teaching Tax Flow: The Podcast

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky dive deep into the transformative tax changes set to take effect in 2026. As a follow-up to their previous discussions, they address crucial tax modifications outlined in the "One Big Beautiful Bill Act," including deductions on tips, overtime, and notable alterations to the standard deduction, all while pro...

In this episode, co-hosts John Tripolsky and Chris Picciurro dive into the intricate world of 2026 tax changes to charitable contributions . Kicking off the new year, the guys provide a detailed analysis of what taxpayers can expect with the introduction of the One Big Beautiful Bill Act (OB3), the most significant overhaul of the tax code in about a decade. Chris and John shed light on the variou...

In this episode of the Teaching Tax Flow podcast, hosts John and Chris usher in the New Year with invaluable insights into commonly missed tax deductions. Dubbing it a conversation you "may not want to admit is a problem," the discussion promises to shed light on often overlooked opportunities within your tax return, aiming to empower listeners with newfound tax knowledge ahead of their 2025 tax p...

In this episode of the Teaching Taxable Podcast, co-hosts John Tripolsky and Chris Picciurro reveal significant updates to the 1040 tax form, aiming to prepare taxpayers for upcoming changes. Designed as a "holiday gift" to listeners, the episode dissects alterations targeting discrepancy issues between taxpayer filings and IRS records. Chris presents a detailed walkthrough of these modifications,...

In Episode 166 of the Teaching Tax Flow Podcast , hosts Chris Picciurro, CPA and John Tripolsky break down the often-overlooked Secure 2.0 Act and explain why it plays a critical role in retirement and tax planning—even if it doesn’t get the same headlines as the Tax Cuts and Jobs Act or the OB3 Act. Dubbed the “middle child” of tax legislation, Secure 2.0 introduces sweeping retirement changes be...

In this episode of the Teaching Tax Flow podcast, hosts John Tripolsky and Chris Picciurro dive into the intricacies of Health Savings Accounts (HSAs), unpacking their extraordinary tax benefits. They highlight how HSAs can be a powerful financial tool for individuals looking to manage their healthcare expenditures while also enjoying significant tax advantages. As they explore the components of H...

In this episode of the Teaching Tax Flow Podcast , hosts John Tripolsky and Chris Picciurro, CPA , sit down with college funding expert Brian Eyster to break down one of the most misunderstood financial planning topics for families: FAFSA and college financial aid strategy . Episode 164 delivers a clear roadmap for navigating the rising costs of college by blending smart tax planning with proactiv...

In this episode of the Teaching Tax Flow Podcast, host John and tax expert Chris delve into a pivotal topic in taxation - the Marginal Tax Rate (MTR) . Sponsored by Wealth Builders Mortgage Group, the podcast aims to shed light on the intricacies of tax strategies that transcend the basic understanding of tax brackets. Chris reveals why MTR is considered the primary Key Performance Indicator (KPI)...

In this episode of the Teaching Tax Flow podcast, hosts John and Chris jump into the intricacies of the Section 179 deduction, a crucial topic for small and medium-sized businesses seeking tax advantages through immediate expense on qualifying property. The episode demystifies this often-confused segment of the tax code, ensuring business owners and tax professionals understand its application, el...

In Episode 161 of the Teaching Tax Flow Podcast , hosts Chris Picciurro, CPA , and John Tripolsky welcome back special guest Parker Borofsky of Wealth Builders Mortgage Group to discuss one of the most common financial challenges entrepreneurs face — qualifying for a mortgage while self-employed. Parker brings a lender’s perspective to this crucial topic, sharing real-world insights into how lende...

In this episode, Chris Picciurro, CPA, and John Tripolsky break down the IRS’s brand-new form: Schedule 1-A (Form 1040), created to handle new deductions introduced by the One Big Beautiful Bill Act (OB3). Starting in the 2025 filing year, millions of taxpayers will use this form to claim deductions like No Tax on Tips, No Tax on Overtime Pay, Automobile Loan Interest, and Enhanced Deductions for...

In Episode 159 of the Teaching Tax Flow Podcast, hosts John Tripolsky and Chris Picciurro, CPA, tackle one of the most talked-about provisions of the One Big Beautiful Bill Act (OB3).. No Tax on Tips rule. This episode cuts through the noise to clarify what “no tax” really means, who qualifies, and how tipped workers and self-employed individuals can take advantage of this new deduction starting i...

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-...

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 protectio...

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 pr...

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, i...

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 tax...

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, re...

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...

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 lend...

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, IR...

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...

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, t...

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 retiremen...

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 strategi...