I used to have problems delegating stuff, but its just a matter of skills. I dont know shit about coding, so I NEED to get other people to do it for me. But yeah, even then I'm still a pain in the ass if things dont look right (pixel perfect, alignment issues, etc.) and most of the time I actually do end up fixing the code myself.
I can't stand the slackness of other people, seriously I hate it and it's the ONLY thing that gives me stress about running a business. It's not dealing with douchebag clients or billing them, to me its actually organizing the right resources to make a solid project.
The perfect world would be in one where I can send something to get build and have it turn out up to my expectations. Anything less and I'm here going crazy and stressed out angry at the non-perfectionists that cant get stuff right.
But you know what, I think this only feel this way on the web world. I think the internet gives us this impressions that things will get done quickly and you will save time but it simply doesnt work that way. Its something you have to grew accostumed to.
I actually spend about 1-3 hours just writing an email and making calls on skype just to get some dude get things right, say a quick php code. But you cannot expect some dude to follow along with your expectations if he himself is not familiar with yours. He might be familiar with the expectation of some dude's business of selling full sites for $200 bucks. And cheap work is cheap work is cheap work. No other way around it.
Now, give me a staff to work with in person, people I have interviewd and know the way "I" work and you can be DAMN sure I will have things happen fast and all the problems/screw ups will be fixed with no place for BS.
It doesn't work that way if you are simply delegating stuff to the first dude you find that has the skills and knows how to speak USA English. He can code "The Matrix" for all you know, but if he isn't familiar with your work quality and perfectionism he simply will not go all the way for you.
Damn it, I am in the wrong industry.