QSBS, Solved
QSBS for Startup Founders and "Structural Alpha", with Brad Dillon (a16z)
In this episode, host Brady Weller chats with Brad Dillon about how founders can leverage Section 1202 (Qualified Small Business Stock (QSBS)) to optimize their equity tax strategy long before an exit. Brad Dillon is a partner on the a16z Perennial team (Andreessen Horowitz), where he advises founders on tax, trust, and estate planning. His work focuses on issues that arise throughout the founder journey, including QSBS, equity compensation, pre-liquidity planning, concentrated stock, charitable giving, and transferring wealth to future generations. Before joining a16z Perennial, Brad advised ultra-high-net-worth families at UBS on tax, estate planning, and philanthropy. He began his career in private practice, most recently in Milbank’s trusts and estates department in New York. The conversation unpacks critical founder tax topics, detailing how the Section 1202 QSBS exclusion incentivizes venture capital investments in high-risk, pre-commercial startups. Brady and Brad examine how to avoid severe tax hits (such as the 37%+ tax shock on Series A secondary share sales) while navigating state-level QSBS eligibility rules in high-tax states like California and New York. They also cover practical equity strategy, from filing timely 83(b) elections to executing QSBS stacking and preparing for IRS guidance on trust planning and QSBS Rollovers. Whether you are optimizing your cap table or structuring a tax-free exit strategy, this episode provides a roadmap for preserving founder equity value and keeping capital in the startup ecosystem. Contact: Brady@QSBSrollover.com | www.QSBSrollover.com Disclaimer: This podcast is for general informational and educational purposes only and does not constitute tax, legal, financial, investment, or other professional advice. The discussion reflects the personal views and experiences of the speakers as of the date of recording and may not reflect current law, regulations, or IRS guidance, which are subject to change. Nothing in this episode should be relied upon as advice for any specific situation. The implementation of Section 1202 (QSBS) rules and impacts are highly fact-specific and depend on individual circumstances; listeners should not act or refrain from acting based on this content without first consulting a qualified tax advisor, attorney, or other professional regarding their particular facts and circumstances. The host, the guest, and their respective affiliated firms disclaim any liability arising from reliance on the information presented in this episode.
