Hi cool kid,
just quick question, is there any software(Norton, Anti-Spy) which is blocking web-rick server from registering to port 3000, just confirm it. and one more thing after you run ruby script/server, don't kill/stop wait for it terminate, i guess it may through error saying unable to register port 3000. etc., ...(your web-rick server should be allowed to access port 3000(default) or which ever you are using).