There's no possible scale of values that you could use to evaluate this comparison. It's not even apples to oranges. It's like saying Facebook is doing better than beagles. The things don't fit into the same category at all.
Here's a random example: one of the Debian apps is aptitude. It manages packages on the command-line. If you are a Debian sys-admin, it very likely enormously important to you. Nevertheless, it makes zero sense to say it's "doing better than Facebook." That sentence is just meaningless.
Comparing Debian to Facebook in terms of revenue is literally senseless. Debian is a free - free as in beer, free as in freedom - operating system. It does not exist to make money. That was my real point since I suspected the OP meant "doing better" in terms of money.
Maybe I'm just overlooking it, but I'm not seeing a claim that Debian is or was more successful than any company that was founded during the DotCom bubble.
The OP claims that 99.99% of all websites back in the day were shit, just like 99.99% of all iphone apps today are shit. He then makes a remark that suggests that Debian is a superior platform because the number of debian apps is small/manageable.
Now, I pointed out that out of the vast majority of shit of the early web came a bunch of valuable companies, and I conjecture that it was in part due to vast number of websites were built that it became _more_ likely that the web as a platform would be successful and that some websites would become hugely valuable.
From that I consider it a risky bet to say that the vast number of iPhone apps in itself makes the platform inferior.
I then finished off by pointing out that no debian _apps_ that I was aware of had in any way become as successful as a bunch of websites I could care to mention. Maybe it was that which confused you - they are separate but related points.
It arguably helps power Facebook, Ebay, Google, Amazon,... and any number of other of those sites you mentioned. Or perhaps Python? is it less successful?
Or perhaps you defined successful in terms of revenue only? In which case that's a very narrowly defined term and the case could be made that such a narrowly defined definition of success adds "zero additional value" to the conversation.
I don't see a lot of debian apps doing better than facebook..