QSBS Opinion Letters, OBBBA Updates, and SAFEs with Chris Karachale
Update: 2025-08-26
Description
In this episode of QSBS Solved, Brady sits down with tax attorney Chris Karachale of Hanson Bridgett to unpack a few misunderstood components of Qualified Small Business Stock (QSBS). They discussed the practical realities of opinion letters and audit defense and the latest OBBBA updates on exclusion limits and gross asset thresholds.
The conversation 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.
Contact: Brady@QSBSrollover.com | www.QSBSrollover.com
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