Yep; same here. I'm 33 now, and I'm unreasonably proud to say that I still have essentially every file I ever created, going back to hundreds of Bank Street Writer and KoalaPaint files created on my Commodore 64 in the mid-1980s.
You're just ahead of your time. Fortunately, with the way computing seems to be heading, one day we all will be able to say we still have every file (document, image, etc) we ever created.
Oh, I think it remains to be seen whether cloud computing will make the problem better or worse. If all of our data is eventually consolidated with a few very large companies who do a good job of preserving it and keeping it accessible to us, then that may be an improvement.
But keep in mind that these companies are not in the archival business. Fresh data is a lot more valuable to them than old stuff. Yes, Google scans old books and whatnot but that's a tiny amount of data compared to everyone's digital junk heap that they accumulate over a lifetime.
If I consider everything I've ever written on the internet to be my "files" then I've already lost a great deal of it just because I can't keep track of where it all is, let alone whether it's still online at all.
He might have meant the cheapness of storage and I sure hope he did. I could have kept incremental backups of all my digital creations in the last 20 years and it would not be 1 terabyte.
I don't know. Modern people also create a lot more files than back in the floppy days. Many files are created to be consumed over short period of time, and probably discarded when they become inconvenient.