I removed the "I regret a lot" portion of the title, because I've wasted money, but don't regret any of it. Each time I recognize that I've wasted money, I take it as a lesson for how to spend properly in the future. It's like paying for financial lessons :)

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1. Advertising for my books
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The best advertising is word of mouth. The money I dropped on advertising books was largely wasted and destroyed any profits I might have had on the books. I still do spend a little bit on advertising (primarily on Amazon), but only in small amounts that I only increase if I see a decent return on the investment.