Ask How do you build a customer base for a paying membership site?

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I keep seeing successful membership sites, but I don't understand how they get paying members. I know people join free communities easily, but convincing them to pay looks different. Should I focus on content, ads, or something else? I also wonder how to keep members from leaving too soon. I don't want to start without a clear plan. If you have grown a paid membership site, I would love to hear what worked for you.

How do you build a customer base for a paying membership site?