A secondary needs a willing buyer and a defensible price, so it usually becomes realistic only once the company is doing well enough that investors want more of it. In practice that often means from a strong Series B onward, when a new lead sizing up a round is happy to buy some existing shares alongside fresh ones. Very early on there is rarely a market for your shares and no agreed valuation to sell against, so pushing for a secondary can look like a lack of conviction. It also depends on your cap table's rules: rights of first refusal, transfer restrictions, and board or investor consent can all gate a sale. There is no fixed stage that is right for everyone; it turns on demand, your ownership, and the signal you are comfortable sending. Talk to your board early rather than surprising them.
A curated summary to orient you, not advice. The resources below are the real value.
2 hand-picked resources, 1 link-checked. Pick how you want to dig in.
Why we picked it The clearest short piece on how to think about giving up and holding equity, and why a smaller slice of a bigger outcome is the whole game.
From paulgraham.com by Paul Graham
Open paulgraham.com →Why we picked it A calm explainer of what a secondary actually is, who has to approve it, and how the price gets set, before you raise it with your board.
From Carta by Carta
Open carta.com →The same ground, over in Raise money, our Starting Up track.
