I first started betting in Counter-Strike professional matches and skins-based roulette websites. In two weeks I went from $50 to $1000. Yes, I was pretty lucky, but I am actually thankful for that, because I needed to cashout my skins and the solution was pretty simple: Bitcoin. I didn't knew Bitcoin very well until this point.
hmmm memories... almost started the same way myself...
But in the early 2000s, CS 1.5 for sure.... at local LAN pc zones in a country where internet was not strong enough yet to play online hehe.. we would choose want to play a game... asked who wanted in at the place.... (sometimes arranged matches too with teams already set) .. but captains would chose team 1 by one like soccer captains when we were kids playing etc.... then we would make a individual bet with 1 or more people on the opposing team... so everyone would wager what they agreed to with whoever they wanted as long as they agreed to it too..
not sure if that makes sense to everyone or if i articulated it correctly....
but yeah
then i went to play on the team of the former CS champions of the country i was in, we placed 4th or 5th nationally i think in the one major competition i played in =)
good question!