Ok saw this thread late, If went back to the 1980's particularly early 1980's would do a couple things. Obviously could gamble a bit. The trick on this is to spread it out. Do a hit here or there not big money, just enough to supplement income to put into investments. Someone said they don't remember when stocks went up and down. I disagree that part is pretty easy. Buy BRK and or WMT for me in the early 80's, continue to plow money into those. WMT tops out for me in about 2000, switch over to AMZN, and then around 2008 start looking for Netflix. As to land, see if can purchase some cheap farmland to rent out in western Iowa after the farm crisis. At $200 to $300 an acre, could try to strike a deal with a farmer to pay on an installment contract then rent it out. A little tougher starting out for the first year or two, but things would get much better shortly after. Can use gambling winnings or wages to keep the payments going. By some land around Lake Okoboji as well. Should be Pretty well set at that point. As to the stocks we all know the major pivot points, black Monday, the big crashes in recent memory, 2000, 2008, Covid 2020. Buy some puts during those time periods. Almost forgot, buy some bitcoin in 2008-2010 era for $1-$3 a bitcoin. May even consider getting some equipment to produce.