It's only really in certain areas that that happens, though, mainly webapps. If you want to be a popular provider of something else, free software is often still the way to go, even if you also want to make money.
Clojure, for example, could've adopted a freemium business model, say by allowing the free version to be used noncommercially but requiring a license to use it commercially. But it chose an OSS licensing model instead, I'm guessing at least partly because: 1) the main initial motivation was building an interesting language; and 2) non-free-software programming languages are a non-starter among many potential users.
One could get the same effect through a killer commercial library/app that's only available on a particular platform. I don't know of any real-life examples.
Clojure, for example, could've adopted a freemium business model, say by allowing the free version to be used noncommercially but requiring a license to use it commercially. But it chose an OSS licensing model instead, I'm guessing at least partly because: 1) the main initial motivation was building an interesting language; and 2) non-free-software programming languages are a non-starter among many potential users.