It's one thing to know when to buy, it's another to know when to sell. In hindsight buying at 1.00 made sense with gwern's logic,(I don't think I had even heard about bitcoin let alone gwern's argument at the time) but what happens when it rises to 100.00? In that case, the same logic would tell you to sell, in which case if you had invested 100.00 you'd have made 10,000.00, hardly a life-changing sum. To have made it to 100,000.00 you'd have had to sit and watch as that not inconsiderable sum bounces around the hundreds range, driven by people whose only explanation is "it's going up" while not making hardly any headway in its intended purpose of being an actual currency used for legal transactions. The one person I know who mined it early on did exactly this, he sold it at around the 50.00 point and said it was a bubble when it was in the hundreds range. I still think he's right, it was and is a bubble; I don't see the value in something which has no actual value.
About the rationalists winning, we already 'win' in a lot of ways. We on average have higher incomes, better-managed finances, better health, fewer substance abuse problems, ect, than the average person. But little of that is due to rationalism per-se, as these "rational" behaviors are incorporated into the general suite of lifestyle advice given to the average "normie:" don't get in debt, don't major in that in college, ect. You probably followed them before you ever heard of rationalism. There are a few ways however that the common ideology of the upper-middle class people diverges from rational behavior, and which rationalists would gain an advantage:
1. On infertility. Don't get me wrong, few communities are as sterile as this one, but IF rationalists decide to get married and IF they decide to have kids, I would think they would be more aware of the fact that fertility takes a nosedive around age 37, relative to a non-rationalist of similar income level.
2. On marriage. Rationalists are heavily single, some of that owes to the general sperg-demographic, but I would bet that a lot of them remain unmarried due to a more accurate understanding of the family court system and the divorce industry.
3. On raising children. If they have them, rationalists will be more likely to understand the dominant role of genetics in shaping their children's upbringing, and will thus be spared a lot of expense and heartache caused by people's belief that they can buy IQ points for their child.
In all these cases, it's not anything that allows one to get rich quick, rather, it's the avoidance of a potentially very bad outcome. And that's all you should expect with the fact that the stock market is already rational ... and the corporate ladder largely isn't.(So our skills are of limited relevance there.)