2) Throw up an ad or two, with the goal of having the ad revenue pay your server costs. This will allow you to not worry about the financial situation while you're fighting fires, so you can defer thinking about investment etc until later.
(now after you have the servers tamed...)
3) Make sure you are incorporated. You probably want to be an S corp or LLC.
4) Look at your metrics and decide whether you have a sustainable property or not. (Look at your retention numbers) Based on the data, decide whether you have
(a) a self-sustaining cash cow, (b) something that can be huge and take over the world, or (c) a fad that will grow and die quickly.
If (b), and you need money to get there, start talking to investors. But don't take money too hastily- it's a long term commitment and you'd better know what you're getting yourself into.
If (c), try to sell it to someone who thinks it's a (b) before it dies.
Congrats and good luck!
1. You have significant profits or net income.
2. You have high liability.
3. You're getting funding.
I doubt this meets any of those criteria, unless someone offered to fund him.
Here are the relevant links if you want to see what I'm talking about:
HN Story - http://news.ycombinator.com/item?id=2047818
Podcast - http://cameronkeng.com/podcast-ep-1-incorporation/
Summary/Notes - http://pastebin.ca/2033868
For example, how much would I save by incorporating if I make 1k versus 10k versus 100k a year?
I see a lot of parallels to formspring, whose pagivews/month graph looks like this: http://www.quantcast.com/formspring.me
So you either want to sell as it nears the that peak, or you have to be ready to stick out the trough of sorrow and invest a lot of time into finding a way to grow and monetize it.
So if you have some great vision for how you can turn this into something awesome, super-popular, and monetizable and you want to invest the time in it, you should go for it.
But if not, you're probably going to get some very good offers over the next few days--especially compared to how little time you've invested. If I were you and wasn't totally in love with the site, I'd get out while the offers are good and invest that money into your other businesses. Then when your next site goes viral, you'll just have to wonder how to get it back up ASAP, not how to afford doing so :)
But according to Crunchbase, formspring raised a $10MM series B just over a month ago (well after the decline was obvious). I wouldn't be surprised if some of that went directly into the founders' pockets.