I did the experiment based on one of your articles on "tipping". My
analysis of the results are that the tipping model doesn't work well
for software, vs a waitress at a restaurant, because it is more
difficult for the customer to see you as an individual, which IMHO is
critical. You need the customer to experience a mental "guilt trip"
if they don't pay you a "fair" price.

Yes, I agree this is key. So the question becomes -- how can a software author cultivate that personal relationship with his user base? It probably involves being very responsive and supportive, releasing frequent updates, etc.

In the Mac world, although he doesn't using the tipping model, I think the exemplar is Thorsten Lemke, author of GraphicConverter. He's very responsive, and it's a rare week that doesn't have a new beta version coming out.

Writing the documentation in a personal style might help too.

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