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How many tries it will take depends on a lot of factors, mostly luck. Pay attention to what works and what doesn't, and keep improving.

Somebody else saying "it took me N tries before making $5000/month" won't mean much for you, because their circumstances are different from yours.

and for the record, I'm on attempt 3 and overall something like $10k in the red. (in terms of money invested, I'm not in any debt personally)