In my opinion, always be wary of your CEO asking you to buy more company stock. If possible, do your own research or if you are working in the core product team

In my opinion, always be wary of your CEO asking you to buy more company stock. If possible, do your own research or if you are working in the core product team, see where things are going. Or use stop losses and limit orders etc to make full use of the stock brokerage account. When I got my RSUs in my last company they were worth $45, the company had just announced that the company had lost some customers. While I thought things could only get better from thereon I put in staggered stop loss order - sell x at $42, y at $40 etc, while letting the upside open. I did sell some of the RSUs at $42. Then things turned around and I was lucky to sell some of the stocks at $70. Recently I quit the company. The quarter just before quitting was terrible. The CEO talked about the stock prices during the All Hands and asked people to pour in some more money into the company stock. This sent alarm bells ringing. I sold everything as soon as the meeting ended. Then again, this whole thing might not be for every one.