IS the idea that as the population increases, you'll always have a larger market share in in the future than you do now? Kind of like human inflation? If it's not that, I just don't see how they can keep the lights on month after month, year after year with single licenses.

That's how software used to work. The flip-side is that you bought "as-is" and you couldn't expect updates. Hell you might even have to re-buy a newer major version.

Because yes it doesn't really scale. I've worked at a place with software like that and it creates a lot of bad incentives. Where I was they sold a lot of custom development for revenue beyond the upfront licensing and you can imagine the toll that wrecked on the codebase over time.

So he is right - $150 for a lifetime license of good, continuously developed software is a steal.

New sales, smart spending and low overhead.

Not everything has to be a billion-dollar swing.

Not everything should!