Questions about equity vesting and associated purchasing and tax scenarios.

I was hoping some of you more experienced folks could give me the rundown on how some of the below hypothetical scenarios might potentially work.

Scenario 1 – I exercise/purchase my stock options (that have vested thus far) at the strike price, and then 12 months and a day later, the company I work for gets acquired by a much larger company. If I sell those shares after acquisition (more than a full year since purchasing them), do I pay long term capital gains taxes on that sale? The other scenario would be where I hold the shares for less than a year – say 6 months – and then we get acquired and I sell… would I then have to pay short term capital gains rates on that sale?

Scenario 2 – We get acquired by a much larger company before the entirety of my shares have vested and before I have exercised/purchased any of those shares. Am I paid for any of those shares or am I SOL? Do I get paid for the ones that vested even though I never purchased them? Do I get paid for the ones that haven't vested yet, but I am contractually entitled to, if I stay at the company for X amount of time? I have a friend telling me that they believe I am entitled to compensation for those shares even if they are not fully vested and if I haven't purchased them, but that makes absolutely no sense to me.

Thanks to anyone who can help in figuring this out! I am also just looking to learn any other details around equity that you think would be helpful for me to understand – especially when it comes to acquisitions and what advice you may have in when to exercise options, etc.

submitted by /u/flipper147
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