I don't how it was when Apple was a start-up, but I have never considered macOS or Apple Office suites as "free" or cheap - the way I rationalised purchasing an Apple device was by telling myself that Apple hardwares are overpriced because it includes the price of the accompanying software. Of course, now, as Apple slowly shifts to a hybrid subscription model, you will of course be continually paying for Apple software ...
I don't how it was when Apple was a start-up
Then why are you posting? The whole basis of this thread is Apple as a start up.
I shared a thought that I felt was relevant to the discussion. Some have upvoted it too. If you didn't find my comment helpful / useful, ignore or downvote or flag it and move on. It just makes for a better community than confronting people on why they post here.