About six months ago my neighbor and I built SkyChalk.com, a site where you can post and read messages anywhere.  The idea was to have a hyperlocal message board, where people could leave announcements for neighbors (garage sales, missing cats), missed connections, small businesses could talk directly to their customers, etc.  While we got some decent press and initial interest, the site never took off.  We had trouble getting user density, and people with tech-overload didn’t want another platform to share on.  It wasn’t a big deal – my neighbor and I only spent three months on it, and no money.  It was fun to build.

We’re all critics (especially bloggers), and one of the hardest parts of launching something new is the people who say (either behind your back or to your face) that your concept is flawed.  These criticisms are always amplified post-mortem, and I found myself defending the concept even after it failed.  So it was almost a relief when yesterday I opened up my Mashable email and saw that Caterina Fake, builder of Flickr and Hunch, was releasing the exact same thing.

She has a nicer UI.  She has funding to pay designers.  Hers will have content because she is hiring people to pre-populate the map with it.  Most importantly, she’s received more press and buzz for her private beta than we could’ve ever hoped to achieve.  All of this has me thinking, “crap, what if hers works? what if I gave up too soon?”

The difference between the guy in the coffeeshop and the celebrity entrepreneur isn’t just press connections, money, and experience; ultimately it is this combination of factors.  Together, they can overcome the chicken-and-egg problem and give the concept enough momentum to actually succeed. This was the kind of momentum we never had.

Certainly we could’ve tried to raise money; but if VCs are already giving money to an established entrepreneur to do the same thing, why take a chance on a guy doing his coding in his house in a bathrobe? Again, the celebrity entrepreneur has huge advantages.

The idealist in me wants to think that anyone can build anything cool in Silicon Valley and have a chance at success.  The realist knows that connections and money may be more important than the product itself.

Do I think Pinwheel (Caterina Fake’s iteration of the idea) will succeed?  I think she has a shot; her site looks great and she obviously knows how to roll out a new product.  On the other hand, there will be many challenges in getting organic, user generated content that is dense enough to work hyper-locally.  It is very hard to get people to post: most of us aren’t content creators – we’re critics.

Maybe guys in coffeeshops can’t compete with celebrity entrepreneurs.  Maybe it takes a  garage – witness Google, Apple, etc.  For my next project, I’ll be renting a parking space.

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Shameless plug: follow me on Twitter to be alerted next week when I release a new concept!! This one is pretty cool! (@RemarkedlyBlog)