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The billionaire one is kinda easy
Sports betting to get your base funds up to a decent level then buy the shares in the successful tech companies post dot-com crash. Wouldn't hurt to buy some gold and bitcoin too.
Sports betting would continue helping you live a lavish lifestyle until all the investment income gets to a good level.
If you do well enough, you should be able to amplify what you've already made to acquire an absurd amount of wealth on the subprime mortgage crash in 2008.
Bitcoin wasn't big by 2010, so you couldn't make much money that way.