When starting the game dont start with wasting all your money on clothes. You'll need it later for characters like ren that need about 2mill to renew contracts and what not. Also as tempting as it is avoid going on alot of dates. Start off by improving skills, personally i like to clear up to level 3 on each skill. Then when you go to perform work on one type at a time, for example only do singing performances until your level is at 4, then move on. When you do dress your star stick to one theme, like pop star and dress him from only one theme. It makes your success rate much higher.