In UO (Great Lakes) I used to GM Stealth in INNs and wait for people to drop shit to transfer to other toons and I would pick their stuff up from the floor while they were switching. I made millions of gold this way, and a few friends. (You had to log out at an inn if you wanted to be able to immediately switch characters, otherwise you had to wait). It was hilarious watching them looking around for their stuff. Sometimes I would unstealth and taunt them. Good times.
Of course owning the shop closest to the main city didn't hurt my pocketbook either. I had to fight 10 other guys to claim that land. I sold GM potions and poison barrels mostly.
As far as my first guild.... do MUDs count? I would have to say my first guild was in 1993 in a MUD called TDome, but I ran my first guild in DAOC (we were a uber crafting guild who used craft exploits to make LOTS and LOTS of gold early on in the game... personally I had 3000 gold when they were selling on ebay for $1 each but used it to buy black and pink dyes for our guild uniforms instead of ebaying... everybody got free dyes We built and used the first seige weapons ever in DAOC. It was a trebuchet and we were running with DDH at the time in the PVP zone. I still remember smashing the shit out of Regulators with it that night.) Anyway when the PVP servers opened up we abandoned the PVE server and some of us merged with Angry Elves/DDH on Merlin.
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