Paying Users are Your Nicest Users
When I finally flipped the switch to add paid subscriptions to Obsidian Portal, I was terrified of the coming support nightmare. I reasoned that if people were angry and demanding when it was free, they would be infinitely more angry and demanding after they had paid. Instead, what I quickly learned was that the paying subscribers were vastly more polite, understanding, and patient than the free users.
My customers don’t pay me in order to buy the right to yell at me. Most of them don’t care at all who I am. They pay money because my service addresses a pain point in their lives. They’re so happy at how well it addresses the pain point that they gladly get out their wallets and fork over payment. If there’s an interruption in the service, they aren’t interested in pointing fingers and assigning blame. They just want the service back. If service interruptions or bugs are the norm, they may get angry, but the point is that they don’t get extra angry just because they paid.
On the flip side, many free users don’t seem to feel any need to hold back their criticism just because they haven’t paid a dime. The most brutal savaging we ever had came via Twitter from a user who was having trouble logging in. He had no patience, no understanding, and took his complaints straight to the Twitterverse instead of contacting us directly. Nowhere in his litany of hatred did he say, “Oh well, I’m not paying anything for it, so I guess I should just shut up.” His rage, and his willingness to express it, had absolutely nothing to do with how much he had paid.
Now, I’m not suggesting that you treat your paying users poorly or take them for granted. What I am suggesting is that you relax any fear you have about being beholden to them because they paid you. Asking for payment does not fundamentally change your relationship with your users. Some will love you, others won’t. But, there’s a good chance that the ones who love you will match up to the ones paying you.