If you have trouble asking people for money, don't ask for the green stuff. Ask for the beautiful purple Australian dollars—with flowers!
Always ask people to pay for your book or other content. Yes, you can give some content away for free, but the really good stuff you should charge for. People value the content they pay for. And, when people discover good things, they like to share those good things with other people. They are far more likely to share the things they've paid for.
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Book Marketing Tip: Ask for the Order