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