Win some/Lose some:
Pool: Odessa TX in the late sixties, won $400 in a 6-ball ring game w/ 4 fellas that spoke fluent Spanish, but short on English. Spent the nite in the hospital over that when they wanted it back PLUS some of my skin. Didn't get to keep it very long but that's the biggest pool WIN for me. Did I really just say WIN??. Biggest one time lost was $1900 shootin 9 ball w/ a little fat guy that had two 6'5 bodyguards at each door of the pool area in a bowling alley in downtown Dallas, late sixties. Hadda get mom to wire money to buy gas.
Stocks: 1999-2001 Day traded my 401K/IRA $$ I accumulated from 18 yrs. in oilfields (Hell, I could barely figure out how to SPELL Day Trading. let alone doin it. I had no business doing that, but,....stupid is as stupid does.
Heard about Paul Allen buying a 10% stake in a small Washington state utility. Bought 1000 shares at $3/per just at the close. Went duck hunting next morning. Checked on it that afternoon....BAM! $15/ per.....SELL!
Driving to a real estate showing & listening to the radio, some guru says, shipping company, Dry Ships looks promising. I buy 1000 at $15/per when I get home that pm. 18 months later it's at $151/per! Leaving for a 10 day elk hunt in CO and somewhere before Reno w/ crappy cell service call wifey and tell her how to put in a stop/loss order for $130. Just had a bad gut feeling, ya know? Next day at opening bell, it fell THRU the stop to $120/per. God protects idiots, right?
Real Estate: Bought a condo out of foreclosure, $69K in 1985. Sold it in 2004 for $236K & 1031'd into 11 units in Napa CA and turned that over in 2019 to a $2.6M office park in Walnut Creek.
Got a duplex in Sac, Ca for $180 in 2003, sold it 2005 for $460K & moved that gain to 44 units in Vacaville. CA. Have no idea what that's worth at present.
Finally:
I've been REALLY luck in my life.....dad died when I was 14, went to work in TX oilfields at 15. Didn't graduate any college. Made a couple of bucks along the way but the BEST SCORE of my life was April 30, 1977! All it cost me was $2900 that I got for selling a 1973 Harley Superglide to my brother so I could buy a set of wedding rings. To quote a country song..."and she said YES!"
44 years later I'm still not in jail, dead, or broke and as happy and thankful as anyone on earth has a right to be.
Somewhat sorry for the long post, but hell's bells, fellas, I'm from TX, whaddya expect!