Leopold Aschenbrenner [...] just blew up his $45 billion hedge fund

Nomen est omen strikes again (Aschenbrenner can colloquially be translated as "money burner").

It seems like their problem is less their quack economics and overconfidence than that learning the basics is hard, practicing them requires self-discipline and willingness to fail, and they can always talk a friend into wiring them another $100,000. So they sling the lingo but generally know less than a high-school graduate who reads books on personal finance from the library and spent a few summers running a house-painting business.

I would be really really really surprised if, on average, LWers (et al.) performed better or worse than the average schmuck who decided to take a punt on proper investing or running a business or whathaveyou.

Beating the market is extremely hard. Riding the market is unbelievably easy, and gets easier constantly. Running a successful business is nearly impossible and gets harder all the time.

For these reasons most people don’t bother, take a job in somebody else’s company, and sometimes invest their savings in something very broad and shallow and safe like an index fund.

On the other hand, rationalism is an extremely well-funded cult, so it’s top-heavy with unbelievably bad decisions made with infinite thielbucks.

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Probably you can find a fair few good stories which are couched as “donations” because, again, rationalism is a cult, and investments in a business are framed in terms of “donations”, or tithes, to this or that cause within the movement. It may not offer a concrete return to the tither, but as with a tithe they do actually expect to get something in return.

If Scott Siskind Alexander very publicly kicks a few bucks to Max More’s cryonics scheme every now and then alongside human enhancement research to preserve a future for our white children, and makes sure he’s picked the RIGHT AI alignment protocol, he isn’t a neutral third party to the future those decisions are helping design.

The whole architecture of the group is a speculative ponzi scheme projected far off enough into the future that nobody can complain when their abstract ideas of expected return fail to come good after all.

Indeed on another level looking for good stories about bad investments is a bit of a contradiction in the sense that what you’re looking at to begin with is, for whatever else turns up in the ‘TESCREAL’ acronym, primarily a scam dreamed up by Eliezer Yudkowsky back in the early 2000s no different from scientology and L. Ron Hubbard.

their problem is ... [several items omitted] ... they can always talk a friend into wiring them another $100,000

Assuming you're correct about that, I would love an explanation of how they come to have this enviable problem. Is it primarily a matter of social class, or is there some more specific category of origin which produces people who can't invest or run a business, but never run out of opportunities to keep trying?