How do you fix undercharging early customers without angering them?
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When we were starting out we set our prices super low just to get anyone through the door.
It worked for getting initial sign-ups, but it accidentally trapped us with low budget users who demanded endless custom help while we severely undercharged enterprise teams getting massive value. Raising prices on those early adopters months later was an absolute operational nightmare. For founders who had to rework their tiers after launch how did you handle migrating early users to higher plans without destroying trust?
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The smoothest way to get around this is grandfathering what they already have, but putting all new features and upgrades behind the new pricing. You can pair that with a discount so they feel taken care of instead of punished for being early. You can even make that discount a locked-in legacy one if your budget allows.