Well, it has different types of players. If you remember the “Leeroy Jenkins”-video then you know what I mean. There are those who calculate all the risk and nail down their math before they do anything. And there are those who charge in with brass balls and don’t give a single f’ as long as they have chicken. You have the same types in EVE. One fly for Red Frog, the others are high-risk traders. Everyone is having fun in their own way.
When you look at the losses of the player from Charon | torchwood 456 torchwood | Killmail | zKillboard then you’ll see that he only ever lost one freighter and that he used a Vigil Fleet Issue as webber (a frigate with 50% web range bonus). The character is from 2011 and he has only ever been ganked once in all this time it appears.
Maybe this was his first attempt at high risk trading or perhaps he’s been doing it for a while and has been very successful at it. Who can say?! But except for this one loss does it look pretty flawless to me.
(Interesting side fact, when you look at the character’s bio then you’ll notice he’s an owner of a CODE. permit [not expired].)