"Think about it this way. If you were trying to solve any problem with software, which would you choose?
A unmotivated, unskilled team with the best technology
A motivated, skilled team with the worst technology"
This is saying that skilled people with worse tools will still create a better product then people with the best tools but no skills. In the roofing analogy it would be someone who uses the best shingles and hammers and other tools, but screws up the installation and the roof leaks anyways, vs someone with less good shingles but installs things so well that its still a good roof.
I think this lesson is extremely relevant in technology. For example, there are some developers who are more interested in the technology choice than solving the user problem well, and the result is a long development time with subpar user experience. On the other hand I've used excellent services, stable, fast, good UI, built with tech that I'd never personally choose. I can only imagine that those teams have great developers despite having to work with tech that isn't as good.