I think it's at least three things:

1. win95 has waning cultural relevance, and nobody has any fresh memories of dealing with its slowness

2. most of us have seen "windows bad" jokes a million times over by now - it's stale

3. "run" is a pretty weak/generic connection.

Edit: 4 - "I'm bad at running" has a sort of boomer-humor vibe to it, it's less relatable to an audience that's generally in-shape.