"How much did you lose before you made your first $100 in poker?"
About 35 cents, back when I was 10. The first $100 I made on the first hand I played seriously. It was a 10/20 7-Stud Hi-Lo (no qualifier, cards speak) private game and the first hand I played, I made the wheel for the scoop.
After that, there were the usual ups and downs, bigger ups than downs, though some spells of runbad lasted a helluvalot longer than I'd like to see. It doesn't last forever.
Playing 10NL, I've seen +/- $100 swings. It took 3 months to dig back out from a very bad May and June last year.