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> Does anyone have any insight as to why companies fail to do this?

It’s really hard to quantify the positive benefit of letting them stay, and really easy to quantify that letting them stay is going to cost us $500/month forever.

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Turnover still applies to the “free” users. If the burden is simply so high the company is going to fail otherwise then do what you got to do, but don’t assume grandfathering people in means spending X$/month for the next hundred years or anything.

Sometimes it's also abuse too depending on the product. If you have a product that can get twisted into a phishing mechanism or injecting crypto miners somehow that can be the worst for whack a mole. I still think in many cases this is solved by just discontinuing new free plans and dealing with the population you already had.

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