- Employee # <125. Exercised options on a vested block of pre-IPO stock before leaving. After IPO and waiting period, sold a chunk for low-mid 5 figures, wanting to spread the sales and capital gains over multiple years. Later that year, sold the rest for 1/4 my exercise price.
- Employee # <20. Exercised some ISOs. Company acquired, all value went to preferred share holders, I received an education in classes of stock and AMT credit carryovers. Got some incentive bonuses to stay with the acquiring company.
Takeaways:
- Work your job for salary. Don't expect stock options to pay off.
- Employee # <125. Exercised options on a vested block of pre-IPO stock before leaving. After IPO and waiting period, sold a chunk for low-mid 5 figures, wanting to spread the sales and capital gains over multiple years. Later that year, sold the rest for 1/4 my exercise price.
- Employee # <20. Exercised some ISOs. Company acquired, all value went to preferred share holders, I received an education in classes of stock and AMT credit carryovers. Got some incentive bonuses to stay with the acquiring company.
Takeaways:
- Work your job for salary. Don't expect stock options to pay off.
- Sell some periodically, even if it's going up.