Currently, I have both a start-up and a consulting business (self-funded), and having some trouble deciding when it is appropriate to delegate overhead tasks. The most common advice given to start-ups is to avoid employees and avoid costs. Little is said about deciding when it is best to incur them.
For example, the decision to have an accountant do all my personal and business taxes was a no-brainer: I estimated I would spend 20-25 hours on them and his quote was well below what I would make in the same amount of time.
Typically, I'm working 55-60 hour weeks. A portion of that (5-15 hours, it varies) is overhead in the form of accounting, correspondence, etc. The decision to have a friend build out my company website was more out of a need to save time - it wasn't so clear I couldn't get it done (but at a lower quality) and save money. It's difficult to gauge if I should spend time marketing or hire out, spend time running errands or hire out, etc. While I'm trying to figure this out, Seth Godin posts:
Self sufficiency appears to be a worthy goal, but it's now impossible if you want to actually get anything done....and he pretty much summed up my dilemma spot-on. There's a lot of pride in being able to do everything myself, but there's no problem in putting that aside if it brings me back my free time.
All our productivity, leverage and insight comes from being part of a community, not apart from it.
The goal, I think, is to figure out how to become more dependent, not less.
Hire when it hurts.In the book, they suggest that you should look into hiring as a last resort and instead seek over avenues to solve your problem:
Essentially, if you've looked into all other options and you still can't keep up with your workload over an extended period of time, it's probably time to consider bringing on some help.
As for what overhead tasks you should push off onto a new hire, it's going to be cheaper for you to push off some of the mundane and repetitive tasks. In addition, if you're the type of person who takes pride in getting your hands dirty, you're going to want to keep the more 'heady' work for yourself, anyway.
In terms of overhead time, I wouldn't use an amount of time spent on the overhead as your test. Instead, I would ask yourself these questions:
It should be pretty easy to figure out whether hiring someone would result in more money for your startup if you have those figures with which to work.
You may find that you can take half a step toward hiring by trying out some contractors to see if it helps. I like oDesk and Elance for finding people with a variety of skills. Once you establish that 1) it works for you to have someone else doing a certain task and 2) you have an ongoing need for the help, then look into hiring an actual employee.