> Again, if you believe the stock is going to go up, and you want the stock, go ahead and keep these RSUs.
I would caution against this and just say: sell your RSUs and ESPPs immediately upon vesting. There's an argument against doing so for ESPPs—especially ones that have appreciated—due to reducing your tax bill. But for most cases, the difference in your tax bill just isn't worth the additional exposure of your net worth to your company's volatility.
I would further caution that it is far too easy to overweight what you think you know about your company when projecting its performance and severely underweight factors that you don't have any clue about. Your company's tech stack might be incredible and the product is a hit, but the sales team is nonexistent and your biggest competitor is two months away from eating your lunch. Or your product is complete shit but the CEO has been quietly negotiating a deal with Google on the side for 25% over market price. Or your company is executing at the top of its game and is completely unbeatable… until an unforeseeable market correction puts it out of business six months later.
As much as you think you know, you have absolutely no idea what your company's stock price is going to do over the next month, quarter, or year. If you happen to be in a position where you actually know, you're going to be bound by significantly stricter insider trading policies than just your company's standard trading windows.
I would caution against this and just say: sell your RSUs and ESPPs immediately upon vesting. There's an argument against doing so for ESPPs—especially ones that have appreciated—due to reducing your tax bill. But for most cases, the difference in your tax bill just isn't worth the additional exposure of your net worth to your company's volatility.
I would further caution that it is far too easy to overweight what you think you know about your company when projecting its performance and severely underweight factors that you don't have any clue about. Your company's tech stack might be incredible and the product is a hit, but the sales team is nonexistent and your biggest competitor is two months away from eating your lunch. Or your product is complete shit but the CEO has been quietly negotiating a deal with Google on the side for 25% over market price. Or your company is executing at the top of its game and is completely unbeatable… until an unforeseeable market correction puts it out of business six months later.
As much as you think you know, you have absolutely no idea what your company's stock price is going to do over the next month, quarter, or year. If you happen to be in a position where you actually know, you're going to be bound by significantly stricter insider trading policies than just your company's standard trading windows.