Try:

"Us humans are so limited in our capabilities. I'm willing to admit, in many ways, I run slower than Windows 95. God, I'm awful at jogging."

Running is the connection here, that's clear. But it seems to me that jogging should be the punchline, not Windows 95. Win95 works as the setup. Maybe I prefer that because Win95 is a much more specific thing than jogging. The punchline "I was talking about Windows 95 all along!" just feels so arbitrary compared to "I was talking about jogging all along!"

There's also a bit much lifting done in your punchline (double meaning of run + bringing in Win95), but even when you disjoint the two a little more, it doesn't work that well:

"I'm awful at jogging. I run slow... I'm not even the Windows 95 of joggers."