I'm hoping to get support the site with advertising and sponsors, preferably from startups and from VCs. It's not a YouTube-like site where I'm expecting multi-million pageviews a day, but I think building a small yet strong community of entrepreneurs and VCs may be an attractive place for either of these groups to advertise in.

Edit: I'm not trying to break anyones bank or wallet here, if the community can be built up, I would just like to keep it self-sustaining, meaning paying for the dedicated server. Like I said, this was just an experiment - I am working on another project I hope to release as my primary source of income.

The trouble with getting VCs to advertise is that their preferred way to generate deal flow is through trusted relationships. It would be difficult to do this purely through advertising (and it costs them less to just use word of mouth, not that they are tight on the money these days...).

Getting startups to advertise isn't very logical either because most of the time the target audience isn't the so-called TechCrunch 50K (unless they are advertising a job opening, but again, this is more often that not fulfilled through word of mouth and personal recommendations).

This is an unfortunate reality of the way the world works (although arguably word of mouth is a lot more effective in some cases).

Honestly, I think you're best chance at monetization is advertising for companies that provide the proverbial "picks and shovels" to startups--cut a deal with a hosting company, a domain registrar, The Company Corporation (to register as an LLC or C/S-Corp). Perhaps you'd have better luck getting some lawyers that deal with this stuff to advertise on there. (Think about this: you know who all the big VCs are, but do you know any good lawyers?) There are few other types of services that fall into this category. It would be neat to let people rate their experiences with different service providers.