In the Beginning
The Smiling Assassin did not start off in EVE Online as a scammer but after getting sick of ratting for ISK he started building Stabber's and then, before the faction icon was introduced into contracts, he would rename them to Stabber Fleet Issue and sell them by the dozen in Amarr.
Amarr at the time wasn't plagued by as many scams as it is today so it was a very profitable enterprise, so much so that TSA setup an alt whom would be dedicated to scamming and increasing his ISK.
Over time the Stabber scams evolved into corp scams, with early attempts being as simple as asking benevolent CEO's if they could lend him ISK for PLEX. Of course this came with promises to repay any loan but never were.
Remaining in a corporation longer than a few days TSA would ask for roles in order to make use of Corporation Hangers or get access to any Corporation Hangers and in turn POSes (should corporation have one in high sec). This was another hit and miss thing and several times he turned his hand too early and had to leave before being able to steal anything.
However over time his social skills improved and he would be able to not just get ISK from marks but also access to Corporation Hangers which, often contained plenty to steal. In every case, if it wasn't nailed down the TSA would steal it.
The Fairer Sex
TSA has refined his corp theft methods each time he uses it but it isn't his only approach. He's found a female character, who has a permanently broken microphone, to be a very good method of extracting ISK from unsuspecting players who try to flirt and ingratiate themselves.
Pretending to be that elusive of EVE Online player, "the female gamer", has been very profitable with this particular alt has been a member of at least six corporations and has been able to extract from each at least one PLEX and a lot of ships and modules.
Inside the Mind
EVE is played by many different personalities and in many different ways. Talking to TSA you get the feeling that he enjoys the meta-game more than the "spaceships in space" game play and this turns out to be true as I found when I asked him about his play style:
Understanding how I play the game and what will explain why I play the way I play, is that I find the meta-game of EVE infinitely more fun than the actual game itself. I still love PvPing, don't get me wrong I enjoy the game itself, but it's all of the additional facets that aren't present in other games that keep me interested.
I asked what he thought about the PvE or ratting aspect of the game and he replied, rather bluntly, that:
Any kind of ISK-grind absolutely kills the game for me.
It's no surprise, PvE/ratting can be incredibly boring and very tiring to do and again no surprise that he turned to alternative methods of ISK income comprising corp infiltration and scamming.
This leads us nicely into the next chapter of our story, the infiltration and mockery of a, minor, null sec alliance.