“we did not apply it to our existing customer base they were grandfathered in if they reached out to us we honored the old price effectively indefinitely”

Grandfather existing customers when raising prices

When Skylight doubled its subscription price from $39 to $79, it applied the new price only to new customers. Existing subscribers were grandfathered into Legacy Plus with no change, and anyone on the fence could email for the old price indefinitely. This preserved goodwill and sacrificed only a few million in theoretical revenue uplift. When raising prices, protect long-term brand equity rather than trying to extract maximum short-term revenue from the existing base.