Qualified Small
Business Stock
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
How Drone Businesses Use the QSBS Tax Exemption to Pay ZERO Capital Gains
Rupprecht Law P.A.
QSBS authority Christopher Karachale shares insight on how qualifying drone businesses can unlock the Qualified Small Business Stock (QSBS) exemption to dramatically reduce, or even eliminate, capital gains taxes on exit.
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.
QSBS Opinion Letters, OBBBA Updates, and SAFEs with Chris Karachale
QSBS Solved
In this conversation, Christopher Karachale breaks down how QSBS really works for emerging companies, cutting through common misconceptions around opinion letters, recent OBBBA changes, and early‑stage structuring. He also tackles the ongoing SAFE debate, explaining when QSBS holding periods may begin and what that means for founders, early employees, and 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
