http://glassbead.net/
This is a social game played (for free) in a flash client. It's been 5+ years of nights-and-weekends bootstrapping (we did receive a few thousand dollars from one of our dads a couple of years ago, but that's all the funding we've got).
We (three founders) are mid-thirty-somethings with families. We feel pretty confident in the game itself--people who play it enjoy it and come back to play again.
What we're trying to figure out now is three-fold: a) how to get the "critical mass" of users we need so that something is always going on so when new users come to visit, there's someone for them to play, or at least a few games they can watch (and what is that number?). We've pretty much milked our family and friend connections at this point.
b) we'd love to have money so we could do it full time, market it, etc. but because we're so far along already (i.e., it's working) we're not sure whom to turn to (VCs, for example, aren't really interested because we don't need very much money). Do we just keep bootstrapping, or are there groups that fund people like us?
c) any feedback (we're looking for feedback mostly from anyone who's actually played it, but we'll consider anything really)?
We hope to be able to take subscriptions soon ("premium service" which would give you some minor advantages in the game, or at least a few more options, cash tournaments, blog, etc.) and we're considering having "sponsored" beads (beads are our playing pieces, which represent everything in the known universe--from Oreo cookies to apples to Darth Vader) as the primary revenue source someday.
We're holding a tournament tomorrow (Saturday, March 29) at 6p MDT if anyone wants to just come and watch (or play, of course).
1. No explanation: A first-time visitor will have NO idea what the site is about. You have a bunch of "Register now" links, but without some idea of what the site is, there's no reason for anyone to register. This is a fairly serious deal breaker that will significantly limit your rate of adoption.
2. Email confirmation sign up: Once again, this will limit the number of people who sign up. Requiring users to first give you their email, and only then register once they've received it, is slow and outdated. I'd remove the confirmation step entirely, but if you really feel you need it you should allow the user to first sign up and only then confirm.
3+ The concept vaguely intrigued me (what little of it I could glean from your confusing videos on the main page), but for this to be successful you need to seriously revamp your site. To be frank, it looks like something made in a previous era of web development.
Interfaces should be easy to use and clearly laid out. Yours does not provide enough information at the start, and presents too many irrelevant pieces upon login.
As in all startups, the ideas behind them could be great, unique, groundbreaking, etc. but if the implementation isn't up to snuff you'll go nowhere.
I realize this criticism may be harsh, but you did ask how to gain a more widespread user base. The best way to gain users is to make the concept easy to understand, and dead simple to begin using.