I work for a somewhat big tech company that went public last year. I was lucky enough to have a good amount of equity (stocks are all ISO’s, not RSU) in my original offer from being an early employee. In September this year, 1/3 of my shares that I exercised last year before going public, I will be able to sell at long term capital gains to maximize my tax benefit, which is my current plan.
The company’s stock is very volatile, from a high of $400+ to a low of sub $200, all within 8 months of the IPO. This month, it’s fluctuating between $220-250.
My question is - for the rest of my vested but not yet exercised shares, and my future vested shares - should I just sell at short-term and pay the larger ordinary income tax ? Or is it more beneficial for me to exercise my vested shares now and unvested shares as they vest (and pay the horrendous AMT) then wait until one year to sell them - not knowing what the stock price will be? I do believe in the company so I don’t believe it will go under - especially within a year. I also know the rule of not having all your eggs in one basket, but at the same time tax sucks and just the thought of having to pay so much extra tax scares me.
Any help, especially with those that were in a similar situation, would help!
Submitted June 13, 2021 at 02:14AM by anditax https://ift.tt/3znss4Y
