So I'm just thinking that the ability to start your own guild would be awesome! Now before you bash me and say "not gonna happen" I was thinking it should be along the knights of the nine setup.
Except your guild is specific to the goals of your character! Your a hero? Guild dedicated to protection of skyrim! Your a murderer? Guild dedicated to controlling skyrim behind the curtain!
So what do you all think? Any other ideas would be welcome for sure!

I'd like to start a prositution guild.

And a skooma/moonsugar dealing guild.

That'd be kewl.

My character is a pimp. My guild is at Skyrim's service.

I'd make my own secret imperial guild. We train to be skilled Magi and take over the empire! MUHAHAHAHAA :intergalactic: :flamethrower:

This sounds like a really cool idea honestly, but still, I don't see it as something that is likely to be in a TES game. It sounds like it would work better in the Fable series or even Dragon Age maybe. It would have to be a game with plenty of generic, randomly generated NPCs to recruit into your guild, which TES has very few of.

Anything they could possibly do regarding this would be so underwhelming that everyone would be disappointed.

Utterly underwhelming.

A Chaotic Good guild :

"Minsc will lead with blade and boot! Boo will take care of the details".

To do all good deeds , evil shall be erradicated! :turtle: