This is how some of my friends and myself have done it for years. On first contact, offer to do one gig for free; ONE gig! This way, they really get to see what you can do. Can you keep their establishment’s customers interested so they’ll stay and spend more money? After all, that is where your money will come from. All kinds of factors go into this: Your volume, the songs you play, are you entertaining, or do you just stand there like zombies? Playing one gig for free lets ’em see you and hear you better than any video ever could. They get to experience you! Once you have done that ONE FREE GIG, and you’ve done it right because now they are interested in having you or your band back, from then on, they PAY for your loyalty! As far as how much money to ask for, be realistic! You want them to be able to comfortably afford you or your band given the money you or your band can actually generate for their establishment by, as mentioned, keeping the customers, but also bringing in some new ones. You can “Write Your Own Ticket” when you get to this point. If you can’t generate a profit for their establishment that will allow them to comfortably pay you, then they will not hire you. Plain and simple. Anyhow, if one free gig turns into fifty, or even just five future paying gigs for you or your band, isn’t it worth it?