QSBS
Investor’s Hub
Collaboration with Carta
Conversions for QSBS Status: Best practices for restructuring LLCs taxed as S-Corporations
November 2024
By Nancy E. Dollar and Michael Sechuga
The Fragility of QSBS Status and How to Protect Your Tax Benefits
September 2024
By Christopher A. Karachale and Natasha Arora
Interactive Guide to Qualified Trades or Businesses for QSBS Qualification
This interactive guide reviews each piece of administrative guidance issued by the IRS on qualified trade or business status under IRC section 1202(e)(3). The descriptions of the business and the legal analysis are taken verbatim from the existing Private Letter Rulings (“PLRs”) and Chief Counsel Advice (“CCA”).
Christopher Karachale Quoted in The New York Times
July 16, 2025
How Republicans Supersized Silicon Valley’s Favorite Tax Break
“Everyone was like: ‘Are you joking?’ These founders and early employees, they’re already getting a huge benefit. So if anything people are thinking: ‘Wow it’s remarkable the statute got opened up all this more.’”
– Christopher Karachale, partner, as quoted in The New York Times
VIDEO & PODCASTS
The 2025 QSBS Overhaul: New Rules, Bigger Opportunities
First Citizens Wealth: Building More Than Business
Partner Christopher Karachale joined the podcast to discuss recent developments in qualified small business stock (QSBS) and related planning strategies.
- Major OBBBA changes, including a higher gain-exclusion cap and new holding periods
- Practical tips for trust stacking, LLC-to-C-corp conversions, and Section 1045 rollovers
- Key steps for documenting eligibility and avoiding mistakes
QSBS Opinion Letters, OBBBA Updates, and SAFEs with Chris Karachale
QSBS Solved
This conversation with Christopher Karachale dives into:
- QSBS opinion letters — what they actually do (and don’t do), and why they serve as more of a penalty shield and documentation tool than a guarantee.
- OBBBA changes — how raising the exclusion and gross asset caps reshapes opportunities for founders, early employees, and venture funds.
- The SAFE debate — whether Simple Agreements for Future Equity should trigger QSBS holding periods, and the practical implications for early-stage investors.
Unlocking QSBS for Startup Founders with Christopher Karachale
Insurtechs
Qualified Small Business Stock (QSBS): $10 Million Tax-Free Secret with Attorney Christopher Karachale
Brooklyn FI
Understanding QSBS Eligibility and Maximizing Your QSBS Benefits
Valur
