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I mean, bitcoin obviously. It would be 2008, so a bit late to short the housing market. But all that can come later.

First thing - go through my room and throw out basically everything. I collected so much shit and none of it ever made me very happy. Then establish a good bedtime routine, so I would get 8 hours of sleep every night. Chop off the hair I was growing out long (I look better without it) and get a set of electric beard clippers (way easier than shaving with a razor, so I'd actually do it). Actually get some halfway decent clothes, and ask my folks if I could get lasik. Start lifting in the schools gym after classes, start going to the climbing gym across town on weekends, and cook real food for myself rather than eating the processed crap my folks were serving me. Establish a consistent study schedule for my classes, and maintain a much higher gpa.

Via these things, in about 6 months I'd be way hotter. Proceed to make passes at all my high school crushes.

By the end of high school, get admitted to a top 10 uni. Use the social skills and work ethic I've gained since college to work hard and party hard. Get laid a bunch and get hired by a FAANG out of school with a $250k starting salary, probably in SF. Work for 2 years, then pivot to a smaller company with the same salary, but working fully remote. Start digital nomading. Using the money I'm earning, buy some houses at cheap prices in awesome locations (will refi during covid).

And of course, search out all the good friends I have from my current life and re-friend them.