I have a Grails application, built to a war file (~30mb). When I attempt to deploy the war file on Tomcat 6 via the application manager, it takes upwards of 10 minutes to deploy
Definitely check the Tomcat logs for any errors/warnings.
You probably have some expensive/sensitive code logic in one of the ServletContextListeners. They are usually initialized during startup. If so, then I would debug/profile it for any performance matters/leaks.