How founder secondaries work at Series B/C, typical amounts, tax implications, and how to signal them to investors without hurting the round.
A secondary sale lets founders and early employees sell some shares for cash without waiting for an exit. Done well at the right stage, it removes personal financial pressure and keeps founders focused on the long game.
Existing shareholders (founders, early employees, angels) sell shares to new or existing investors. Shares change hands; the company receives no new capital. Usually run alongside a primary financing so investors underwrite once.
Series B onwards, when the company is clearly working and founders have been under-compensated for years. Uncommon at Series A. Signals distress if attempted at seed.
5–20% of a founder's holdings at Series B. Enough to remove financial pressure (pay off debt, buy a house, diversify) without signaling you're leaving. $1–5M is a common range at Series B.
Often priced at a discount to the primary round (10–20%) because common lacks the preferences preferred stock carries. Some rounds allow founders to sell at the preferred price — negotiate this in the term sheet.
In the US, if the shares meet QSBS requirements (held 5+ years, C-corp, gross assets under $50M at issuance), gains up to $10M can be excluded from federal tax. Coordinate with a CPA before selling — mistakes are expensive.
Selling too much (>30% of holdings) reads as 'founder is checking out.' Selling in a bridge round or during weak metrics reads as escape. Time secondaries to strength — reasonable amounts alongside a strong primary round.
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