It is reasonable, and increasingly normal, for a founder to sell a small slice of equity in a secondary once the company is doing well. The case for it: your entire net worth is one illiquid asset, and a little liquidity lets you stop making decisions from fear. The case against: it needs board and often investor sign off, a large amount can send the wrong signal, and the cash is taxed. The healthy version is small, taken early enough that it is clearly about de-risking rather than cashing out, and discussed openly with your board rather than sprung on 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.
