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Filing Taxes After Exercising Start Up Options

bradygentile.com

1–10 of 51 posts

Re: Filing Taxes After Exercising Start Up Options

#2
I would add one thing: if you're really going to exercise options before you can sell them, which is what this article's about, you really should calculate the tax consequence beforehand. As is only hinted in the article, the AMT can be enormous if the valuation has grown a lot since the grant date.

Re: Filing Taxes After Exercising Start Up Options

#6
Thank you for this, I exercised stock options last year but never received form 3921 from my ex-employer. What are my next steps here? I reached out to my employer, but I doubt they'll get back to me. Do I need to report this to the IRS?

Re: Filing Taxes After Exercising Start Up Options

#7
Semi related to this blog post:

A lot of people don't realize that you can exercise ISOs before they vest. If you are sure that you are going to be exercising your options there is no reason to wait until they vest and, in fact, there are disadvantages to doing so.

As soon as you get your options (within 30 days. there is a time limit.) you tell your company you want to exercise then and file and 83B with the IRS indicating that you have done so. This avoids potential AMT taxes at the time of exercise and starts to clock on making your gains long term capital gains which are taxed at a lower rate.

Re: Filing Taxes After Exercising Start Up Options

#8
post #5

I think you should at least mention the option of hiring a professional accountant.

Anyone have a professional accountant in San Francisco they would recommended for this sort of thing?

Would love an accountant rec in NYC as well.

Re: Filing Taxes After Exercising Start Up Options

#10
There should be a guide overall on how RSUs work, especially in an early-stage context, for startup employees. I feel like people toss percentages around but don't grasp the meaning of what they're about.

This guide basically convinced me I need to talk to an attorney and accountant haha.

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