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 HSAs, they make complex financial concepts accessible, guiding listeners step-by-step through potential cost savings and tax efficiencies.
HSAs, as discussed in this episode, are not just mere savings accounts; they are a "tristar" tax-advantaged investments that offer threefold benefits: contributions are tax-deductible, the account grows tax-free, and withdrawals for qualified medical expenses remain tax-free. Chris relates his personal experiences and provides strategic advice, encouraging listeners to maximize their HSA contributions where feasible. Emphasizing actionable steps, the episode demystifies eligibility criteria and optimal usage scenarios for HSAs, reinforcing their potential in long-term financial planning.
Key Takeaways:
Resources
• Teaching Tax Flow Website
• Defeating Taxes Community
Episode Sponsor:
Legacy Lock
Book a 30-minute complimentary discovery session at teachingtaxflow.com/legacy
(Mention Teaching Tax Flow for special pricing)
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 proactive financial aid preparation. Brian demystifies the FAFSA process, explains major updates families must know, and shares actionable steps to maximize eligibility for need-based aid.
Throughout the conversation, Brian highlights how income, assets, and timing play crucial roles in how much financial aid a student may receive. Listeners learn the key differences between FAFSA and the CSS Profile, how the shift from Expected Family Contribution (EFC) to the Student Aid Index (SAI) changes planning conversations, and why starting early—ideally during a child’s sophomore year of high school—can make a measurable difference.
Parents also gain clarity on how certain assets work against them in the financial aid formula, what should be avoided at all costs, and how to strategically position their finances during the “base year” to legally and ethically reduce their SAI.
Notable Quotes
Resources:
Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23
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) for effective tax planning, emphasizing its critical role in guiding tax strategies and decisions.
Throughout the discussion, the distinction between marginal tax rates and tax brackets is elucidated, with Chris stressing the deceptive nature of tax brackets in comparison to the impactful MTR. He elaborates on how understanding one's MTR can drastically affect financial decisions and outcomes, particularly in tax planning contexts. Chris also touches on various elements like phase-outs and hidden taxes that influence one's marginal tax rate, offering listeners deep insights into tax planning. Highlighting the significance of implementing strategies that align with individual MTRs, Chris reinforces that comprehending one's MTR is pivotal to effective lifetime tax management.
⸻
KEY TAKEAWAYS
✅ MTR vs. Tax Brackets: Marginal Tax Rate (MTR) is the most critical measure in tax planning, overshadowing the deceptive tax brackets.
✅ Tax Planning Strategy: Understanding and utilizing the MTR allows individuals to make informed choices, reducing taxes legally and ethically across their lifetime.
✅ Elements Affecting MTR: Chris highlights factors like phase-outs, deductions, and hidden taxes that can alter one's MTR significantly.
✅ Implementation over Ideas: Effective tax reduction hinges on implementing strategies that align with one's MTR to ensure maximum tax efficiency.
✅ Resources for Education: The podcast encourages utilizing Teaching Tax Flow content, such as YouTube and their community for further learning and clarity on tax concepts.
⸻
EPISODE SPONSOR
Wealth Builders Mortgage Group
Your trusted mortgage partner for investors and entrepreneurs.
👉 www.wealthbuildersmortgagegroup.com
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, eligibility, and strategic use in financial planning.
With vivid explanations, the conversation revolves around the distinction between Section 179 and bonus depreciation, the importance of electing into Section 179, and its application across various business entities. Chris shares relatable anecdotes from his travels and hands-on teaching experiences, further contextualizing these complex tax concepts. Through practical examples and thoughtful guidance, listeners will gain a robust understanding of how to leverage Section 179 to its fullest potential, whether dealing with tangible property or considering the timing of significant purchases.
Key Takeaways:
Resources
• Teaching Tax Flow Website
• Defeating Taxes Community
Episode Sponsor:
Legacy Lock
Book a 30-minute complimentary discovery session at teachingtaxflow.com/legacy
(Mention Teaching Tax Flow for special pricing)
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 lenders view self-employment income, tax returns, and documentation when approving home loans. Together, the trio breaks down how tax planning decisions, deductions, and entity structures directly impact loan qualification, often in unexpected ways.
This episode offers invaluable advice for self-employed individuals, small business owners, and real estate investors looking to position themselves for mortgage success without sacrificing smart tax strategy.
Key Takeaways
Notable Quotes
Resources
Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23
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 Seniors.
Chris explains how these new “between-the-lines” deductions work, who qualifies, and why knowing your marginal tax rate is more important than ever.
KEY TAKEAWAYS
✅ Schedule 1-A is brand-new and will apply to millions of taxpayers starting in 2025.
✅ Includes four major new deductions under OB3.
✅ Each deduction has unique income phaseouts.
✅ Accurate documentation and understanding of eligibility are essential.
✅ Always verify if your state conforms to the new federal deductions.
RESOURCES
• Teaching Tax Flow Website: www.teachingtaxflow.com
• Defeating Taxes Community: www.defeatingtaxes.com
• Teaching Tax Flow YouTube Channel: www.youtube.com/@teachingtaxflow
EPISODE SPONSOR
Wealth Builders Mortgage Group
Strategic mortgage solutions for real estate investors.
Visit www.wealthbuildersmortgagegroup.com
🎧 Listen on your favorite podcast platform:
👉 Spotify https://bit.ly/3KdmtJL
👉 Apple Podcasts https://apple.co/3ZkyEtX
👉 Amazon https://amzn.to/4qmdqa5
👉 iHeart https://bit.ly/iheart-TTF
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 in 2025.
Chris breaks down eligibility factors, income phase-outs, and which occupations are recognized as “customarily tipped.” From servers and stylists to rideshare drivers and entertainers, this new rule has far-reaching implications, but it’s not as simple as it sounds. The hosts also explore examples illustrating how this temporary deduction applies between 2025 and 2028, why voluntary tips matter, and what both employees and employers need to track to stay compliant.
KEY TAKEAWAYS
• The No Tax on Tips deduction (effective 2025 – 2028) allows qualifying workers to deduct up to $25,000 of voluntary tips from taxable income.
• Applies to both employees and self-employed individuals in occupations that customarily receive tips.
• Only voluntary cash or card tips qualify — automatic “service charges” are not eligible.
• Social Security and Medicare (FICA) taxes still apply — this affects only federal income tax.
• Phase-outs begin at $150 K (single) / $300 K (MFJ); full phase-out at $400 K (single) / $550 K (MFJ).
• Married couples must file jointly to claim the deduction.
• Proper record-keeping of all voluntary tips is essential for compliance and deduction accuracy.
RESOURCES
• Teaching Tax Flow Website: https://www.teachingtaxflow.com
• Defeating Taxes Community: https://www.defeatingtaxes.com
• YouTube Channel: https://www.youtube.com/@teachingtaxflow
EPISODE SPONSOR
Sunsets & Dinks
Save 15% at https://www.teachingtaxflow.com/pickleball with code TTF15
🎧 Listen on your favorite podcast platform:
👉 Spotify https://bit.ly/3KdmtJL
👉 Apple Podcasts https://apple.co/3ZkyEtX
👉 Amazon https://amzn.to/4qmdqa5
👉 iHeart https://bit.ly/iheart-TTF
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 business owners. This episode provides a clear and actionable discussion of IRS Section 469, passive activity rules, and how to correctly apply the “seven tests” to determine whether income is passive or active.
Listeners will gain practical insights on documentation, common misconceptions, and how education remains key to staying compliant while maximizing benefits.
Key Takeaways
• Material participation determines whether you can use passive losses to offset active income.
• The IRS defines seven tests for material participation under Section 469 — understanding which applies to your situation is critical.
• Proper documentation (time logs, spreadsheets, or tracking apps) is essential for substantiating material participation claims.
• Not every real estate investor qualifies as a “real estate professional” for tax purposes — W-2 employees often don’t meet the test.
• Continuous education is vital for both tax professionals and clients to navigate evolving tax law and avoid misinformation.
Notable Quotes
• “We can’t really shut down bad information. All we can do is fight against it with good information.” — Jeremy Wells
• “The goal here, if you’re the taxpayer, is to try to have active income offset with those passive losses.” — Jeremy Wells
• “Just because you have a real estate license doesn’t make you a real estate professional for tax purposes necessarily.” — Jeremy Wells
• “You need to keep that contemporaneous log… just like mileage tracking for your real estate portfolio.” — Jeremy Wells
• “Education is still a key part of the work that I’m trying to do.” — Jeremy Wells
Resources
• Teaching Tax Flow Website: https://www.teachingtaxflow.com
• Defeating Taxes Community: https://www.defeatingtaxes.com
• Teaching Tax Flow YouTube Channel: https://www.youtube.com/@TeachingTaxFlow
Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23
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 LLC is first and foremost a legal entity (not a magical tax shield), while John adds real-world insights on naming, filing, and keeping your compliance in check. Together, they break down the formation process, discuss the importance of operating agreements, and clarify ongoing responsibilities such as renewals, EIN filings, and state fees.
Key Takeaways
• An LLC stands for Limited Liability Company — a legal structure, not automatically a tax advantage.
• Your attorney may get more excited than your CPA — LLCs protect assets, but don’t inherently cut taxes.
• Steps include: naming your LLC, appointing a registered agent, filing Articles of Organization, creating an Operating Agreement, and obtaining an EIN.
• Treat your Articles of Organization like your LLC’s birth certificate and your EIN as its Social Security number.
• Keep personal and business funds separate — open a dedicated business bank account.
• Stay compliant with annual (or bi-annual) state renewals and any required franchise, excise, or withholding tax filings.
• Avoid over-structuring — multiple LLCs create unnecessary admin and costs if not justified by risk.
Notable Quotes
• “An LLC is a legal entity, not a tax-saving machine.” – Chris Picciurro
• “The name doesn’t matter — the purpose does.” – John Tripolsky
• “Think of your Articles of Organization as your birth certificate.” – Chris Picciurro
• “It’s easy to form one; maintaining compliance is where people fall short.” – John Tripolsky
• “Ideas are cheap. Implementation is valuable.” – Chris Picciurro
Resources
• Wealth Builders Mortgage Group (Sponsor): wealthbuildersmortgagegroup.com
• Teaching Tax Flow Hub: teachingtaxflow.com/hub
• Join the Defeating Taxes Facebook Community: defeatingtaxes.com
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 hands-on experience helping business owners implement proactive tax plans—emphasizing organization, accurate bookkeeping, and collaboration with your tax professional. Together, the trio highlight how cash-basis timing, depreciation, reimbursable plans, and entity structure play critical roles in shaping your 4th-quarter tax outcomes.
Key Takeaways
• Get your books in order — profit & loss, balance sheet, payroll, and distributions must be accurate before planning.
• Understand that a deduction ≠ a tax-free purchase. A $100K vehicle deduction doesn’t eliminate $100K in taxes.
• Avoid depreciation traps — bonus depreciation and vehicle write-offs can cause painful recapture if sold too soon.
• Use the cash-basis “twelve-month rule” to prepay eligible expenses or defer income strategically.
• Set up an accountable plan for home-office, mileage, and reimbursements before year-end.
• Track all subcontractor payments and W-9s now—don’t scramble during 1099 season.
• Above all: buy only what you need—don’t let the tax tail wag the dog.
Notable Quotes
• “Buying a vehicle might be good, but it’s not a tax plan.” – Chris Picciurro
• “A $100K deduction doesn’t mean you’re saving $100K in taxes.” – Marit Burmood
• “Cash flow and tax flow are different.” – Chris Picciurro
• “Don’t buy it if you don’t need it—be logical, not emotional.” – Marit Burmood
Resources
• Teaching Tax Flow Website
• Defeating Taxes Community
Episode Sponsor:
Legacy Lock
Book a 30-minute complimentary discovery session at teachingtaxflow.com/legacy
(Mention Teaching Tax Flow for special pricing)
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 professionals on how these insights can influence financial and tax planning. They also share practical stories, analogies, and analysis that make the data approachable and useful.
Key Takeaways:
Notable Quotes:
Resources:
Episode Sponsor:
REPStracker
www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)
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 requirements to phased-out income thresholds, they explain how this law is designed to incentivize specific behaviors and how taxpayers can maximize the benefit.
The episode also includes case studies and examples showing how taxpayers in different income brackets may be affected, emphasizing the importance of marginal tax rate planning to understand the real financial impact.
What You’ll Learn:
• The specifics of the new automobile loan interest deduction under OB3
• Requirements for eligibility (new vehicle, U.S.-assembled, secured loan)
• How phase-outs at $100K (single) and $200K (married filing jointly) affect deductions
• Practical examples of how different taxpayers qualify—or don’t
• Why your marginal tax rate (MTR) is a critical metric for evaluating tax strategies
Key Insights:
This new provision could provide meaningful savings for qualifying taxpayers, but the rules are nuanced. Proper planning ensures you avoid phase-out surprises and maximize deductions where possible.
Notable Quotes:
• “Tax laws are written to encourage and discourage certain behaviors.” – Chris Picciurro
• “Now there’s a deduction on a personal tax return for qualified automobile loan interest.” – Chris Picciurro
• “For every thousand you’re over, you lose a deduction of $200.” – Chris Picciurro
• “Your number one KPI in tax planning is your marginal tax rate, not your tax bracket.” – Chris Picciurro
• “If you’re over $100,000 in income, you start getting phased out of this deduction.” – Chris Picciurro
Resources:
• Episode Sponsor: Wealth Builders Mortgage Group
• Teaching Tax Flow YouTube Channel
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 tax-free growth. Jessica shares how these funds work, why they were introduced, and how business owners and investors can leverage them before key deadlines hit in 2026.
From real-world examples to industry insights, this episode highlights how QOZs can support economic development while also delivering powerful tax advantages.
What You’ll Learn:
• How Qualified Opportunity Zone Funds allow investors to defer and reduce capital gains taxes
• Why the program was created and which communities benefit most
• The timeline for Opportunity Zone deferrals (and why 2026 matters)
• Strategies for pairing QOZs with other tax planning tools
• Key industries — like hospitality and real estate — where QOZs have been most impactful
Key Insights:
QOZ Funds are more than just a tax break — they’re a strategic tool for reinvestment and growth. By rolling gains into qualified projects, investors can achieve tax-free appreciation while driving economic development in underserved areas.
Notable Quotes:
• “You are allowed to defer your capital gains into an Opportunity Zone Fund — and if held long enough, the appreciation can be tax-free.” – Jessica Correnti
• “Hospitality has been good because the zones are typically where they’re trying to drive revenue.” – Jessica Correnti
• “Ideas are cheap, but implementation is valuable.” – Chris Picciurro
Resources:
Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23
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 and closely held businesses a clear roadmap for tax-smart decisions.
What You’ll Learn:
• How OB3 permanently extends key provisions like QBI and restores 100% bonus depreciation
• Where Opportunity Zone Funds fit into an overall planning strategy
• SALT cap increases and how PTE workarounds can lower effective federal tax
• New and expanded credits (e.g., FICA tip credit expansion to beauty/service industries) and dependent care limits
• Practical, ethical strategy stacking to maximize deductions while staying compliant
Key Insights:
OB3 creates durable planning opportunities for small businesses—particularly those investing in equipment, real estate, or operating in high-tax states. Pairing QBI, bonus depreciation, and SALT strategy with OZ planning can materially change after-tax outcomes when implemented thoughtfully.
Notable Quotes:
• “What bonus depreciation is, is a provision that allows you to deduct the entire amount of asset purchase instead of writing it off over five, seven, or 15 years.” – Chris Picciurro
• “I think this is something that a lot of people are overlooking and we are going to lean into… in getting a special guest on to specifically talk about Opportunity Zone funds.” – Chris Picciurro
• “The people in our community, the teaching tax flow community, the voice of tax planning, by the way, drive our content, not us.” – Chris Picciurro
• “Now you could deduct if you’re married up to $40,000.” – Chris Picciurro (on SALT increases)
• “Ideas are cheap, implementation is valuable.” – Chris Picciurro
Resources:
• Teaching Tax Flow YouTube Channel
• OB3 Playlist
Episode Sponsor:
Sunsets & Dinks — premium pickleball apparel for the TTF community. Save 15% at teachingtaxflow.com/pickleball with code TTF15.
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 metals, and even cryptocurrency — all while maintaining tax advantages.
The conversation explores how these accounts work, what you can and can’t invest in, compliance requirements, and practical strategies for combining traditional IRAs with self-directed ones. Whether you’re an investor seeking greater control or a tax pro advising clients, this episode uncovers strategies that can maximize retirement wealth.
What You’ll Learn:
• What self-directed IRAs are — and what they are not
• How to diversify retirement funds into real estate, private companies, and more
• The rules for disqualified persons and prohibited transactions
• The difference between custodial and checkbook IRAs
• How to plan ahead for RMDs with illiquid assets
• Practical compliance requirements and why custodians matter
Key Insights:
Self-directed IRAs give investors control and flexibility, but with that freedom comes responsibility. From avoiding prohibited transactions to balancing liquidity for RMDs, Scott explains why working with a knowledgeable custodian is essential for both compliance and strategy.
Notable Quotes:
• “Most people don’t know it’s possible to invest in real estate or startups with their IRA — because their brokerage won’t tell them.” – Scott Maurer
• “Your IRA cannot transact with or benefit a disqualified person. That’s critical to know.” – Scott Maurer
• “Control is the number one benefit of a self-directed IRA.” – John Tripolsky
• “Ideas are cheap — implementation and compliance are what make the difference.” – Chris Picciurro
Resources:
• Join the Community: DefeatingTaxes.com
• Sunsets & Dinks Pickleball Apparel – teachingtaxflow.com/pickleball (Use code TTF15)
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 planning, lending, bookkeeping, compliance, and more.
🎙️ EPISODES FEATURED:
#4 | Real Estate Spotlight (Panama City Beach, FL) – Crystal Ball
https://share.transistor.fm/s/b67de8c3
#6 | Lending Partners – Brenna M. Carles
https://share.transistor.fm/s/72fd8df4
#12 | REPS & Material Participation – Kirsten Limmer
https://share.transistor.fm/s/30d45fac
#14 | IRS Notices & Responses – Andrew Poulos
https://share.transistor.fm/s/60e885b3
#18 | Employee Retention Credit – Heidi Henderson / Stacy Deru
https://share.transistor.fm/s/871b18a4
#20 | Real Estate Spotlight (Fort Walton Beach, FL) – Heather Blatz
https://share.transistor.fm/s/87e104dc
#22 | Self-Directed IRAs – Scott Maurer
https://share.transistor.fm/s/de0be61d
#24 | R&D Credits – Heidi Henderson / Stacy Deru
https://share.transistor.fm/s/d647b847
#26 | Private Reinsurance / 831(b) – Roger Roundy
https://share.transistor.fm/s/639c5b84
#27 | Alt. Investments: Wildlife – Chris Gilroy
https://share.transistor.fm/s/78498cfd
#29 | Real Estate Spotlight (Nashville, TN) – Michael Gomez
https://share.transistor.fm/s/e331b511
#30 | Music & Money (Moon Taxi) – Trevor Terndrup / Tommy Putnam
https://share.transistor.fm/s/d1dd14c6
#32 | Legal Insight: STRs – Jeff Hampton
https://share.transistor.fm/s/d9721d5f
#38 | IRS War Stories – Andrew Poulos
https://share.transistor.fm/s/648fe7da
#42 | Mortgage Prep 101 – Brenna M. Carles
https://share.transistor.fm/s/b9f3f8d9
#43 | Money Tips for Teens – Dave Alger
https://share.transistor.fm/s/99e2828d
#47 | W-2 vs. 1099 – Jason Moll, CPA
https://share.transistor.fm/s/c90ffb07
#49 | How Taxes Are Made – LaShawn Thomas
https://share.transistor.fm/s/3f48c40d
#50 | Why Businesses Fail – Jon Neal
https://share.transistor.fm/s/7b2310c3
#62 | Cost Segregation Study – Heidi Henderson
https://share.transistor.fm/s/c55caa88
#66 | Corporate Transparency Act – Jeff Hampton
https://share.transistor.fm/s/e12eb0ea
#68 | 2024 IRS Update – Andrew Poulos
https://share.transistor.fm/s/96636666
#72 | Bookkeeping 101 – Lisa McCarthy
https://share.transistor.fm/s/583e56e0
#75 | 1099s Explained – Kaitlyn Rummel
https://share.transistor.fm/s/6fb268d7
#77 | STR Loophole – Arda Bircan
https://share.transistor.fm/s/a4411511
#80 | Payroll 101 – Will Lopez
https://share.transistor.fm/s/3d22a846
#83 | Long-Term Care Planning – Brooke Crane Acre
https://share.transistor.fm/s/e9d7f005
#85 | 1031 Exchange Update – Scott R. Saunders
https://share.transistor.fm/s/4dcdb380
#87 | Selling a Business – James Cunningham
https://share.transistor.fm/s/cadd8468
#89 | Real Estate Popularity – Bill Allen
https://share.transistor.fm/s/d62b171f
#95 | Deferred Sales Trusts – Todd Jackson
https://share.transistor.fm/s/68b88f2e
#99 | Corp. Transparency Act – Angelina Urquhart
https://share.transistor.fm/s/9baafa50
🎥 Video Episodes (YouTube):
#101 | Charitable Giving – Caden Gunnell
https://youtu.be/e2lvdeu4QZg
#104 | Credit Unions vs. Banks – Chrissy Siders
https://youtu.be/lRhT5uWDf_o
#107 | Business Life Cycles – Kelly Bender
https://youtu.be/uHPngp7E86g
#110 | Influencers & Taxes – Duke Alexander Moore
https://youtu.be/aomQ83WdueE
#112 | Capital Loss Harvesting – Alex Caswell / Colby Davis
https://youtu.be/W2LDZcS6t_M
#118 | Cannabis & Taxes – Kareyna Miller
https://youtu.be/4glCnI3uXWY
#121 | Farm Tax Benefits – Kelly Bender
https://youtu.be/Pcpq8h3S2xA
#125 | Delaware Statutory Trusts – Warren Thomas
https://youtu.be/PtQbZRIdeT4
#127 | Social Security – Robert D. Soerens
https://youtu.be/NvZ3srHbwAI
#129 | Estate Planning 101 – Court Pitcher
https://youtu.be/Ft0RIQrdpRU
#131 | Infinite Banking – Tom Laune
https://youtu.be/SIb-B61QV_4
#134 | Financing Property – Parker Borofsky
https://youtu.be/tW9xVRBw7aY
#137 | Digital Asset Reporting – Tynisa Gaines
https://youtu.be/fF9XbGfQ0N0
#140 | BRRRR Method – Jim Ingersoll
https://youtu.be/81NcN9hm7O8
#143 | Mindset + Money – Curtis McCollum
https://youtu.be/NpjN_ehtBdY
#145 | OB3 Bill: Real Estate – Scott R. Saunders
https://youtu.be/NYInhhFL0Eg
#148 | QSBS Exemption – Brady Weller
https://youtu.be/JwvchBIRVSU
⸻
RESOURCES:
• TTF Hub: https://www.teachingtaxflow.com/hub
• Defeating Taxes Community: https://www.defeatingtaxes.com
⸻
EPISODE SPONSOR:
Wealth Builders Mortgage Group
https://www.wealthbuildersmortgagegroup.com
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, Prescribe, IQ (Suitability) Test, and Implement. Through real-world examples and engaging analogies, Chris and John show how this approach creates tailored, effective strategies that minimize lifetime tax liability — legally and ethically.
What You’ll Learn:
• The four steps of the proprietary tax planning process and how each works
• Why knowing your marginal tax rate is the #1 KPI for tax planning
• How to determine the right prescription for your unique tax needs
• Common pitfalls when implementing tax strategies without suitability checks
• Why execution matters more than simply collecting ideas
Key Insights:
The same structured process works for every case, but the results are always unique. By diagnosing the current tax position, prescribing the right strategies, testing them for suitability, and then implementing them, taxpayers can avoid wasted effort and ensure their plans fit their circumstances.
Notable Quotes:
• “The process is the same for every case, but the results are always unique.”
• “Just because there’s four steps in this process doesn’t mean it necessarily has to take a long time.”
• “Implementation is key. Make some things you could self-implement like a health savings account…”
• “Your marginal tax rate is your number one KPI for your tax planning.”
• “Ideas are cheap, you can find them on TikTok, Instagram, etc. Implementation is valuable.”
Resources:
Episode Sponsor:
Wealth Builders Mortgage Group
wealthbuildersmortgagegroup.com
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 save you millions in taxes. Brady breaks down IRC Section 1202, explaining how the QSBS exemption allows eligible C Corporation shareholders to exclude up to $10 million (or 10x their basis) in capital gains from federal income tax.
The discussion also covers the QSBS rollover under IRC Section 1045, a strategy Brady likens to a “1031 exchange for company stock” — enabling sellers to reinvest gains into another qualified small business and defer taxes. The episode is packed with real-world applications, planning tips, and insight into recent legislative enhancements through the Inflation Reduction Act, which increased the QSBS exclusion cap and reaffirmed bipartisan support for innovation incentives.
Whether you’re preparing for a major exit or just learning about QSBS for the first time, this episode is a masterclass in how to use specialized tax planning to unlock significant wealth.
What You’ll Learn:
• How QSBS works and who qualifies
• The tax savings potential: $10M+ federal gain exclusion
• How the QSBS rollover under Section 1045 defers taxes
• Legislative updates that make QSBS even more attractive
• State-by-state considerations for QSBS eligibility
• Why early and specialized planning is critical for maximum benefit
Key Insights:
Brady Weller reveals how QSBS is often an untapped goldmine for founders — and why lack of awareness can mean leaving millions on the table. From structuring your business properly to timing exits and using rollovers, the right QSBS strategy can dramatically reshape your after-tax results.
Notable Quotes:
• “QSBS is one of the most powerful tax exemptions available, allowing federal income tax exemption on up to $10 million of gain.” – Brady Weller
• “We dreamed of creating an always available, downside-protected option for founders to execute these rollovers successfully.” – Brady Weller
• “OBBBA made QSBS even more powerful, expanding exclusion cap to $15 million, showing bipartisan support for this incentive.” – Brady Weller
• “QSBS and its rollovers provide a 1031-type tax deferral for company stock, fundamentally transforming tax planning strategies for many.” – Brady Weller
• “Our firm realizes around $3 billion in exit volume, emphasizing significant missed opportunities in the current system.” – Brady Weller
Resources:
• Connect with Brady Weller on LinkedIn
Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23
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.
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.