In this episode of The SoCal Edge, Art Dicker and co-host Alessandro Rinaldi speak with Brian Lamb, founder and CEO of Promissory, a company helping startup founders maximize the tax benefits of Qualified Small Business Stock (QSBS) through specialized trusts.

Brian previously co-founded Trust & Will, one of the leading venture-backed estate planning platforms, and after partiallyexiting the company began exploring how founders could better plan for liquidity events. That journey led him to discover how complex and expensive QSBS trust planning can be — and inspired him to build Promissory to simplify the process.

The conversation covers how QSBS works, why founders can potentially save millions in taxes, when in a startup’s lifecycle this planning should happen, and how software-driven legal solutions are transforming areas traditionally dominated by expensive law firm processes.

What You'll Learn

• What QSBS (Qualified Small Business Stock) is and why it can eliminate millions in taxes
• How QSBS trust “stacking” can multiply tax exemptions for founders
• When founders should start planning for pre-liquidity tax strategy
• How software is transforming complex legal processes
• Key lessons Brian learned as a second-time founder

Key Timestamps

00:00 – Introduction to Brian Lamb and Promissory
02:00 – Leaving Trust & Will and discovering QSBS trusts
04:00 – Turning a complex legal process into a software platform
08:00 – What QSBS is and why it matters for founders
11:00 – How QSBS trust “stacking” works
14:00 – When founders should set up a QSBS trust
18:00 – Lessons learned from building Trust & Will
23:00 – The future of pre-liquidity planning for startup founders

About the Podcast

The SoCal Edge features conversations with founders,investors, and innovators shaping the startup and technology ecosystem across Southern California.