My (non-tech) friend was sighing about this too, until he thought some more and realized he would have certainly sold it at $20. Which would possibly be an even worse feeling.
My initial tranche of options were at $42 in 2004; I sold the majority in 2009. I alternate regret, rage, and joy in the fact that my extremely good luck in getting the job at Apple allowed me to completely clear my family's debts, and provide capital to start an (ultimately) unsuccessful company.
This happened to me with Tesla. I bought a hundred shares at $35, and had a sell order that said, "sell if it drops more than 10%." Two months later, around $80, it fell to $70 or something like that, and mine automatically got sold. Then it jumped to $250.
But I was gambling with it (it's the only time in my life I've bought a single company's stock like that), and I think in retrospect the result is quite good. I just can't shake away the "if only..." feeling. :-)
When I got my car in March 2013, I decided it was so amazing that I should buy some stock. I don't really invest in individual stocks so I bought 100 shares at $20. A few weeks later I sold 50 for $35 (an amazing % return). Then I watched it climb to $280, wishing I bought 1,000 instead and hung on.
Despite my missed opportunity, I think the car is far better than any other vehicle on the road. There really is no comparison. 8-speed double-clutch automatic with paddle shifters? I prefer no transmission. I could go on and on.
Hopefully, someday in the distant future, all of our cars will be non-smoking.
When the G5 Powermac came out I gave some serious thought to putting that money toward stock ($3k at ~$15/share). I needed a computer too badly though...
I did end up buying at 280, 320, 500 though. Sold it all off just before the last split.
Yep. IIRC, The delay was due to not getting a brokerage account setup properly, and then having the stock pop from 12 (almost book value, or $4billion) to $17. At which point I decided that the move had already happened.
