Comment by skybrian

Well… yes, index funds are a safe, default choice most people. And yet, a funny thing about investing, versus other things professionals do like dentistry, is that it doesn’t necessarily require any skill. Dumb luck sometimes works just as well as sophisticated analysis. What other professions are like that?

I don’t think I had any particular insight into Google, but I worked there and never got around to exercising my options until I had to because they were going to expire. (Good thing HR sent me an email.) The slightly more sophisticated people were doing same-day sales and immediately diversifying, which I believe in, in principle. But I procrastinated, because it seemed like delaying was working out pretty well. Past performance is no guarantee, but why not wait a few months?

I thought Google was doing well, but so did everyone else. It was conventional wisdom the whole time. Apparently conventional wisdom wasn’t priced in, though?