> Presumably the one that doesn't have to rewrite everything that they just wrote from scratch to avoid Docker.

I think that's too simplistic. Larry is right that a company who manages to survive 5 non-productive years rewriting everything in a "better" ecosystem will likely be in a better situation than the company trundling along with ever increasing technical debt.

The problem is that the conservative company without the major rewrite is more likely to make it through (at the least the first few of) those 5 years. So Larry's not wrong --- he just might be making some unwarranted assumptions.