This is really a question about risk, not timing the top, so frame it that way. Waiting for an IPO or acquisition can mean a bigger payout, but it is not guaranteed, it can be years away, and many companies never get there. Selling a slice now locks in real money and cuts your dangerous concentration in one illiquid asset, at the cost of some upside if the company soars. A useful test: if the company doubled after you sold, would you feel foolish, and if it went to zero after you did not, would you be in trouble? If a bad outcome would genuinely hurt your life, taking some chips off the table is a defensible, unglamorous choice. This is education, not advice, and there is no single right call. Any sale is taxed as capital gains in India, and those rules change, so confirm your liability with a CA.
2 resources.
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 best reminder that avoiding ruin beats chasing returns, and that wealth is the money you don't spend. The whole founder concentration problem, told as stories.
From The Psychology of Money by Morgan Housel
The same ground, over in Raise money, our Starting Up track.
