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:

• Capital Square

• Teaching Tax Flow Hub

• DefeatingTaxes.com

• Teaching Tax Flow YouTube

Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23

• (00:03) - Exploring Qualified Opportunity Zone Funds and Tax Strategies
• (04:03) - Exploring Tax Benefits of Opportunity Zone Funds
• (06:24) - Sports Fandom and Team Loyalties Across Cities
• (07:29) - Exploring Opportunity Zone Funds and Their Tax Benefits
• (09:27) - Maximizing Tax Benefits with Opportunity Zone Investments
• (15:25) - The Impact and Future of Opportunity Zone Funds
• (22:48) - Understanding Opportunity Zones and Resources for Ongoing Support

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 Website

• Teaching Tax Flow YouTube Channel
• OB3 Playlist

• Defeating Taxes

Episode Sponsor:

Sunsets & Dinks — premium pickleball apparel for the TTF community. Save 15% at teachingtaxflow.com/pickleball with code TTF15.

• (00:03) - Exploring OB3's Impact on Small Businesses and Pickleball Gear
• (01:44) - Exploring Tax Benefits for Small Business Owners
• (04:57) - Key Tax Benefits for Business Owners and Real Estate Investors
• (09:02) - Exploring Tax Strategies and Opportunities for Business Owners
• (14:14) - Tax Strategies for Business Owners in High Tax States
• (17:09) - The Value of Tax Planning and Professional Guidance
• (20:00) - New Tax Credits and Deductions for Employers and Employees
• (26:16) - Understanding IRS Guidance and Tax Planning Strategies

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:

• Advanta IRA

• Teaching Tax Flow Hub

• Join the Community: DefeatingTaxes.com

• Sunsets & Dinks Pickleball Apparel – teachingtaxflow.com/pickleball (Use code TTF15)

• (00:00) - Exploring Self-Directed IRAs and Pickleball Enthusiasm
• (01:59) - Exploring Self-Directed IRAs with Scott Maurer of Advanta IRA
• (06:13) - Exploring Self-Directed IRAs for Diverse Investment Opportunities
• (14:23) - Exploring Investment Opportunities in Self-Directed Retirement Accounts
• (19:03) - Navigating IRA Rules and Disqualified Persons in Investments
• (20:43) - Impact of Technology on Self-Directed Investments and Opportunities
• (24:26) - Navigating Self-Directed IRAs and Custodial Requirements
• (30:49) - Exploring Tax Strategies and Upcoming Content on YouTube

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:

• Teaching Tax Flow Hub

Episode Sponsor:

Wealth Builders Mortgage Group

wealthbuildersmortgagegroup.com

• (00:00) - Introduction and Episode Overview
• (00:46) - Episode Sponsor: Wealth Builders Mortgage Group
• (01:45) - Introduction to Chris and the Episode Topic
• (03:03) - Four-Step Tax Strategy Process Overview
• (05:45) - Step 1: Diagnose Your Tax Situation
• (09:15) - Step 2: Prescribe Tax Strategies
• (10:48) - Step 3: Suitability and IQ Testing
• (13:06) - Step 4: Implement the Strategy
• (15:34) - Conclusion and Community Engagement

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:

• QSBS Rollover Website

• Connect with Brady Weller on LinkedIn

• Teaching Tax Flow

Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23

• (00:02) - Exploring Tax-Free Gains Through IRS Section 1202 QSBS
• (03:09) - Exploring Capital Gains Tax Mitigation with Brady Weller
• (05:19) - Exploring QSBS: A Powerful Yet Underutilized Tax Exemption
• (07:42) - Understanding Qualified Small Business Stock and Tax Exemptions
• (12:04) - Maximizing QSBS Benefits for Startup Founders Exiting Early
• (17:54) - Strategies for Starting or Acquiring a Business with QSPS Credit
• (19:36) - Understanding QSBS Rollovers and Tax Deferrals
• (21:15) - Navigating Related Party Rules in Business Exits
• (22:35) - The Future of QSBs and Tax Exclusions
• (24:37) - Exploring QSBS Rollover Benefits and Personalized Investment Advice
• (27:18) - Investment Offerings and Risk Factors in Financial Memorandums

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
• (05:36) - Managing Retirement Plans and Benefits When Changing Jobs
• (13:52) - Building a Non-Salesy Resource Hub for Tax Advice
• (15:09) - Tax Implications of Job Relocation and Stock Options
• (19:00) - Navigating Self-Employment Tax and Retirement Planning
• (24:19) - Alaskan Fishermen Deductions and Missed Opportunities
• (25:51) - Navigating Retirement Transitions and Financial Considerations
• (28:05) - Navigating Job Changes and Tax Implications

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
• (05:27) - The Shift From Tax Compliance to Forward-Looking Tax Planning
• (10:45) - Effective Tax Planning Through Strategic Implementation and Partnerships
• (19:46) - Exploring Behavioral Tax Planning and Investment Strategies
• (27:22) - Engaging Tax Planning Discussions and Community Involvement