2024 TaxSep 21, 2021
FacebookwmMU03

What to do with stock options from Oscar Health

This is a pretty simple question, I just don't understand the tax liabilities of exercising stock options and was wondering if anyone on blind can give me the 411 :) Basically I have ~5k stock options for Oscar Health and I have to figure out what to do with them the strike price is ~9$ and the stock is currently at 17$. The assumption I'm going with is that the stock will neither rise or fall dramatically, for arguments sake lets just say it stays inline with the S&P 500. My questions is, is there a tax advantage to exercising now and holding for a year vs just buying and selling immediately? I know about long term capital gains tax, I'm just wondering how it applies here. I live in NYC and the job was also there. Any advice would be greatly appreciated, Thanks! #oscar #taxes #stockoptions #options #tax

Oscar YLak23 Sep 21, 2021

It’s just 5k shares do whatever you want…You won’t trigger AMT if you exercise it now. For 5k shares just buy it I’d say, not much cash needed. When Oscar signs a deal, or multiple next year, it will be a different stock.