I've sometimes wondered what it would be like now if some of the big names early in open source and free software had decided to take a detour of a couple decades to work in commercial software with the goal of making as much money as possible, and then retire and use that money to endow a foundation to promote free/open source software development by paying developers.

Imagine if Stallman had gotten the IBM work instead of Gates, and now it was the Free Software Foundation with billions instead of the the Gates Foundation. With those resources their endowment would be generating enough income that they would be able to pay around 10000 programmers a year $100k plus full benefits to do free software work.

That would have meant less free software for those decades while there amassing their fortunes, but then an explosion of free software afterwards.