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I always suggest avoiding the "pay the bills" mentality. For most of us, running a site costs less than cable tv. If you want enough money to pay the hosting bills, just work an extra hour at your regular job each month. Enjoy the site as a hobby and forget about money. There's nothing wrong with that.

Only try to monetize if you really want to make serious money. Otherwise, it's just not worth the hassle.

As to your specific points, I try not to let people lord it over me that they're paying money. You have to assume that they knew what they were signing up for when they click the "pay now" button. A paying user complaining about something isn't much different from a non-paying user. Plus, we've found that paying users tend to complain much, much less than free ones. They tend to be fanatical supporters who also understand that I'm not going to cater to their every whim.

So, don't let paying users pull you away from your vision any more than freebies. If they get too angry just refund their money and move on. The heartache (and time) isn't worth the price of 1 subscription. Plus, this is rare. I've only come close to doing it once in almost 2 years of charging subs. I was about to do it when the guy shut up and stopped complaining. He didn't stop paying, though ;)




I did a writeup of this line of thinking here: http://blog.aisleten.com/2010/02/25/dont-monetize-to-cover-c...




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