Ask HN: Did you get "never have to work again rich" through software?

The people I've seen make a good chunk of change through software are the types that reinvest their money, start new companies, and play again.

For my dad he had enough investments just doing the corporate grind to "retire" around 50. Before medical insurance cost $50K/yr for a family or whatever it is now, obviously, and back before the housing bubble crisis so a house thats like $300K now only cost him $80K. Salaries were about the same, maybe only 50% higher now. The middle class used to be a lot more wealthy...

The problem is you gradually build up investments until you can live a relatively poor lifestyle forever, but he wants the new SUV to make it easier to tow the RV (old people like SUVs, what can I say) so its a 3 month contract during the rainy spring, and then full time RV all summer. Then its too cold to RV in the winter up north, and the house could use a new kitchen remodel anyway and it looks like an interesting project so...

The point I'm making is "if you don't want to" isn't a constant $ value and isn't really easy to define anyway.