What makes you think that "nobody" had an internet connection in "those days?" We weren't riding around on the backs of dinosaurs and cooking up bronto-burgers on the weekends.
Winsock came out in June of 1992, right in the middle of the Windows 3.x life cycle.
I do remember using Winsock on Windows 3.1 to grab Usenet updates on expensive dial-up. The batch Internet :)
So how would they have retrieved this data?
He mentions that Microsoft had a program where they partnered with large enterprises to collect usage data from corporate desktops. But those computers were on a network even if though often not on the Internet yet.
Stats that would show Doom towering over Windows 3.1 must have been collected manually, maybe by sending people a floppy that contained a program to collect the data, and asking them to mail it back in. "Insert floppy, then type A:\SPY.EXE in your DOS prompt" ...
Since nobody had an Internet connection in those days, it was literally impossible to get the data back to Microsoft without the user's involvement.
If 1993 Microsoft could have collected this data automatically, they certainly would have.