4 or 5yrs. old on the kitchen table with family & neighbours.
My family would play every Sunday night after dinner at my Great Grandmother's house (she'd play too). We played a bit during the week too.
By 10yrs. old I'd found a handful of guys who used to play regularly. One of the guy's father used to go to Vegas pretty often & had their basement set up with card tables, & a craps table. Both of this guy's brothers would also play (their father would join us on weekend nights). They also ran a pawnshop in their 3-car garage (lots of bicycles, skateboards & sporting equipment in there). Few of them had paper routes (which was always good). Biggest win at 10yrs. old was $260 one afternoon (but more typical was losing $10 or $20... regularly).
Got into more de-gen. games as a teen but also used to play at school, after school, at the poolhall, etc.
21yrs. old, lost $5,500 on a NewYear's Eve playing HU 5card stud. Quit playing all poker until 2007. Saw a million FTP ads on TV (along with Absolute Poker, & Pokerstars
). Joined FTP, AbsolutePoker & Pokerstars.
Took 2nd in the Ferguson on FTP in very first game I played online (~900 entrants, $1 buyin, won $114). I was hooked