Company stock question
I (36 years old) started working at a high tech startup 7 years ago in the field that I had just gotten a PhD in. I have been partially compensated with stock options. Fast forward to today, and we’re publicly traded and the share price is high. I have been mostly sitting on the shares aside from a big sale a few years ago that was life altering. My kids college funds are full enough and I put about $0.5M into various investment funds.
As of writing, I still have $600k and $800k in vested and unvested company shares, respectively. I think there’s a good chance that my company‘s share price increases by 5-10x. This will sound arrogant, but I’m confident in my analysis of our roadmap because I’m kinda an expert in this field (PhD + 7 years working in the field). Of course, there’s no guarantees but this is how I see things.
I am struggling to find a balanced approach to selling. I oscillate between “sell next time you can make a life changing amount of money” and “sell X shares whenever the price increases by Y.” The former approach ignores lots of potential gain in pursuit of a bigger payout, while the latter approach is structured and safer. I wanna be prepared for when our plans start turning into successes.