The sale itself is similar, but ESOPs carry an extra tax layer that plain founder shares do not. Founder shares you bought or were allotted early are simply capital assets: when you sell, you pay capital gains on the difference between sale price and your cost, with the rate depending on the holding period. ESOPs get taxed twice. First, when you exercise the options, the gap between the exercise price and the fair value is treated as a perquisite and taxed as salary income. Then, when you eventually sell those shares, any further gain is taxed as capital gains, with your holding period counted from the exercise date. So an ESOP holder can face a tax bill before any cash arrives. Startup ESOP rules have special deferral provisions that keep changing, so confirm the current position with a CA.
3 resources, 2 India-specific, 2 link-checked.
The India-specific piece: perquisite tax at exercise, capital gains at sale, and the startup deferral, with worked examples in rupees.
From ClearTax by ClearTax
Open cleartax.in →Zerodha Varsity free module on how investment income is taxed in India: capital gains, holding periods, and turnover, in plain language.
From Zerodha Varsity by Zerodha Varsity
Open zerodha.com →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
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