Never underestimate the value of luck and of being in the right place at the right time. Larry doesn’t have to understand everything - he pays people to understand the things he doesn’t. His main expertise now is with racing boats.
Oracle was kinda sponsored by the U.S. government initially, IIUC (but maybe that's just conspiracy theories floating around?). They had the best SQL RDBMS for a long time, which created mindshare. Back then Larry knew better or didn't think of milking his customers, either way Oracle back then built customers and mindshare. Eventually Oracle began milking their customers. The Sun acquisition experience seems to bear out the idea that they are no longer interested in building mindshare, just acquiring products they can milk, then milk them for as long as possible, and let them die of attrition.