This actually goes a bit back to my days as a high school punk. See I would often hang out with a lot of the neighborhood kids, and I often was looked upon as a leader to them, so I started using that as my handle in a lot of the games we played. I believe the first time I ever used it was for Metal Arms: Glitch in the system (lovely game btw).
Now you may think, oh just tag lost on there, and you got the whole origin? Well, ya, of course you would, but could you let me finish my story jeez.... Anyway while I was often looked up as a leader, I never felt I was the type to led people around. Not because I wasn't capable, but it just wasnt my thing. I'm often dazed and confused myself on what to do, and honestly the majority of the time it led up to just playing games, going out to eat, and listening to what they had for suggests. So when it came time to get a new handle at a little site once known as brawl central I decided on lostleader. I think the biggest reason I stick with it though is because it's such a dumb joke, and it so accurately describes my situation.Also I have a tendency to use LOSTLEAD8R because it looks cool, and I can't use my regular handle.