Actually, that particular example is the opposite of people loving the change. If you lose 95% of activity, most people must be hating the change. And it's not clear that the rest are loving it, unless their activity goes up.

It's easy to judge others without knowing all the facts, but I'll admit I don't like the way Meetup handled that transition.

Taking away something from users always seems like a bad idea. I prefer to do it in a way that keeps existing users happy.

Even today, the copy for the organiser fees on Meetup.com is very strange:

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Did you know? Organizers pay Organizer Dues. Learn More (link)

Yep, Meetup Group Organizers pay Organizer Dues (as little as $12 a month). Some Organizers choose to share this cost with their members.

Meetup is the best for organizing real, face-to-face Meetups!

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Instead of making the user feel good about the purchase, they are making them begrudgingly pay "dues".

And they hide the pricing info in weird fine print. You don't even know how much exactly you're paying until after you've set up a group.

I don't know if they've tried it but their business model could be freemium simply based on the number of members of a meetup group, instead of some other obscure features.

The way I see the numbers in the SVN post is that they got 5% conversion to premium, which is fantastic. I'd bet that almost all organisers who stayed had reasonably large meetup groups. By staying free for small groups, Meetup could have probably avoided losing 95% of the activity and still stayed profitable, while accomplishing their stated goal of "Meetups everywhere about most everything".

It's also funny that they cite Craigslist as an inspiration - a site which is almost completely free, with a tiny sliver of premium features.

Edit: To add to an already long comment:

Meetup charges a measly $19 per month. My local meditation group of 20 people collected more than that every week just by asking members nicely to contribute a dollar each for the tea and biscuits.

I think Meetup is hurting their business and vision by being too small-minded.

I didn't say Meetup's users loved the change. In fact, they clearly did hate it - that's pretty obvious.

My point was that you shouldn't be afraid to do something that 95% of your users hate if:

a) those users aren't bringing in any revenue and are unlikely to do so ever

b) the other 5% love it and end up giving you much more in return (whether that's money or other things)

Ok, you agreed with my original comment and then gave the example of Meetup, so I misunderstood.

I disagree with your reasons for making big changes that most of your users hate, but that's probably because we disagree fundamentally on how to build a business.