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Depends on your level within the company. Senior Mgmt usually have target company holdings they need to adhere to. If you are a lower level employee? I'd diversify by selling as my job is already a risk. Maybe hold 5-10% of your net worth in company stock if you really want to.
On the opposite side of my argument, a lot of grad school friends joined Amazon and Google when we graduated in 2010. They got RSUs and sold off pretty early and had sellers remorse but you gotta remind them those shares could have gone to $0 so they at least locked in some gains.
I have a couple of questions for the thread that I am curious of people's thoughts on:
1. Let's say you win a lawsuit and you have a nice chunk of money landing in your lap, say $300k. Is there any way you can protect that from income taxes? Maybe set up some sort of trust or something?
2. Let's say for whatever reason a sizable chunk of money lands in your lap, not enough that you could retire off of (for many of us), but a nice chunk say $700k. How would you invest it?
By "chunk of money landing in your lap" I don't mean literally. You get handed a check.