One piece of advice that sticks with me is to try and hire so that you make yourself irrelevant--the goal being to build a well oiled machine that runs smoothly without you. This as opposed to one that comes to a grinding halt without you involved in every last decision.
One of the early mistakes I made so far was not to be aggressive enough about hiring early on. That put us behind where we wanted to be because it just takes a long time to find great hires--finding the right skills set, personality, timing. It's just a lot of variables.
So, recently, I met a completely amazing person who has the ability to take the business and operations of Path 101 to the next level once we launch in a month. Of course it's earlier than I ever thought I'd think about hiring a business person, but the more I think of it, the better I think it makes our product.
There are a lot of product challenges we will have moving forward: striking a balance between providing objective career information vs. possibly making candidates available for recruiting, incentivizing people to present honest portrayals of themselves in their content and data, not necessarily wht they think will just get themselves hired first... challenges that demand focus, creativity, lots of observation with respect to the product.. These are things that tend to get bumped when rasisng money, working out legal negotiations with partners, recruiting, working up financial and marketing plans... so it stands to reason that a product focused CEO would want to find a great businessperson as soon as possible, right?
I think that a lot of CEO founders have a hesitation around this and they possibly stay as CEO way too long--to the detriment of the business. I'm the opposite. I know exactly what I'm best at--getting out into the flow of conversation, being "outside guy", being creative and reaching out for business development, making connections, evangelizing. Our business prospect thinks it's too early to join... but I'm more concerned with waiting until it's too late.