Let’s say I’ve been at a company for 2 years, and originally received stock options, which is half vested now (let’s say 500). Now that my company is public, we now also receive RSU AND I can partake into the companies’ ESPP. If you wanted to sell a portion, which would you sell first? Let’s say I have 50 in RSU vesting and getting 50 in ESPP this month, should I sell 100 in stock options and hold the RSU and ESPP or should I keep the stock options and sell the RSU and ESPP grant? What do you all think? I assume stock options since they have already been held for over 1+ year but I may be completely wrong as I’ve been told I should sell ESPP and RSU as they vest and a portion of your overall grant ever few months, no matter how well you think company will do.
Sell all you can. There's really no reason to hold unless you'd also buy these shares with your own money. That's ultimately what it is so you should treat it as such. Holding onto ESPP and RSUs generally can put you at too much portfolio risk. If you're investiging long term you generally should look for a diverse portfolio of low-fee index funds (e.g. Vanguard) or use one of the robo-advisers such as Betterment or Wealthfront.
Thanks @tzku54
Agree with tzku54. I’d only keep options and sell everything else. You already have upside from your income if the company does well
Doesn't your company sell a portion of your vested RSUs automatically to cover the tax liability? I thought this was a standard practice.
Yes.