It would help if you understood his reference, which I believe is the show Holmes on Homes. For example, Holmes the main character/contractor, had to rip off an entire roof (shingles, layering) of a flat-roof structure because it needed to have slight angles for the water to flow off. Otherwise any patching would not produce a leak free roof that would last for 20+ years like it should. I've worked on software projects where we went back in and completely re-worked the UI or re-wrote some data access layer stuff without a full rewrite. That would be a more analogous example.