Pickupball website would be perfect ! (for me)

The pickup basketball website idea was the most intriguing idea to me.  Admittedly this probably more due to the benefit I personally could get from using such a site.  When I moved into this area I had no contacts to play ball with and no good way to make any.  I could search around for good courts to play on...which I did...but that took a lot of trial and error.  The value proposition of giving me a site where I could go to quickly determine the set of locations, number of courts, their quality and how crowded the courts would be is exactly what I needed.  Add on the features that support leagues and tournaments and I can see this site being the one stop shop for helping out the pickup baller all the way up to the gym manager who is trying to organize his league.  The problem is how do you effectively monetize all this?

One idea presented was to team up with gyms and try to acquire sponsorships.  I can see this generating a small amount of revenue.  In addition there should be some advertising revenue.  However, the advertising revenue will not be significant until a very large amount of users are on the site.  This means that early operations that only target local DC areas will likely not be sustainable and will likely not payoff the initial costs of developing site in any reasonable amount of time.  This suggests a few things from my perspective:

1. Seed funding will be necessary to create the site.  The site will need to be high quality to attract the younger audience that will be the users of the site.
2. The site should support as many locations around the country as possible as quickly as possible.  A strong marketing push would help to rapidly raise awareness.  I could see marketing sessions on college campuses, popular malls and highschools helping to quickly spread the word.  Access to the site by users has to be free.
3. This idea has a low barrier to entry so I think it will be important to quickly storm the market and get deep penetration into as many areas of the country as possible.

I think there are opportunities to partner with all kinds of sports related companies out there too.  Once a solid 18-35 user base is demonstrated, tons of companies will want to advertise on the site.