Googling terms like "shareware" and its history (not the only model, there were, of course, outright paid products too), will show some stories, maybe not a lot, since some of this was before the web, so not archived. But will show enough to get an idea. Jim Button was a classic example, but there were many other indie devs (many of them one-man shows), who may not have made it so big, but made good money from desktop apps.

Google term: shareware jim button

Edited to add:

http://asp-software.org/www/history/the-origin-of-shareware/