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In this video, the speaker addresses why many freelancers on Upwork struggle to earn money. They highlight that 86% of new users never make any income and outline three key reasons for this failure. First, many freelancers focus on themselves instead of addressing the client's needs; proposals should avoid starting with "I." Second, there is a tendency to prioritize the quantity of proposals over quality, leading to ineffective applications. Lastly, sending rapid-fire proposals without personalization is detrimental. The speaker offers a successful cover letter template that has earned them over a million dollars, suggesting it could positively impact viewers' freelancing success.