I am actually kind of in this position and have been trying to think of a way to ask this question. It’s not a humble brag. It’s not an exaggeration. Every time I hear about diversification and all-eggs-in-one-basket I also hear “in most cases” or “in almost every case” and wonder what happens if I listen to that advice when they were actually painting me as an outlier. Yes, I want to know if I’m special. I know that’s pretentious but there are special circumstances and what if I’m actually one of them?
The stock I have could, now, just about pay my house off. It wouldn’t significantly change my life. It could also be generational wealth if some of the stuff you read about actually came true. I sold 2k worth of stock over the course of the last 3 years the would be worth over 10k right now.
Taking inflation into account, I have the equivalent of sub-$1 Apple stock in 2004. I am having one real big existential crisis right now. Usually the stories I hear about people getting rich from company’s going public etc their wealth changes overnight. I am in the middle of a multi-year event and I dont know if I should get of the boat while the gettin’s good, or just ride this thing and see what happens. I currently have a plan to divest over 4 years and I believe that I’d walk away with between 1-2 million dollars with that plan. It’s possible if I let it ride it would be very significantly more than that.
What’s your advice?