My $100M Mistake + 6 Company Exit F**k Ups To Avoid (#522)

TL;DR

Two founders play a "Never Will I Ever" drinking game recounting costly mistakes from selling their companies. Core lessons include exploiting QSBS (Qualified Small Business Stock) to eliminate federal taxes on up to $10M+ in gains, never shutting down a business without trying to sell it (one founder estimates a $100M opportunity lost), and treating negotiation as a leverage/stubbornness game, no

Key insights

• QSBS allows exclusion of up to $10M in capital gains (or 10x your initial investment, whichever is greater) at the federal level if you hold qualified small business C-corp stock for five years; it is
• You can multiply the QSBS shield by creating trusts for your children and giving each trust equity, each getting its own $10M exclusion.
• Shutting down a business without attempting to sell it is a catastrophic mistake — the speakers cite an app that got 500,000 downloads in 60 days and hit #1, which they simply abandoned; Bitmoji later