I'm having a hard time parsing some of what you wrote at the end there. First, Google's IPO was in 2004, not the 90's, and e.g. E-Trade was very well established and not so different from today. In any case I don't see what UI/UX have to do with it.
The street hated Google's Dutch auction, and refused to push it to retail investors; a very unusual move at the time. The IPO estimates were at one point over $100, but if I recall correctly, the auction dropped down into the $80s, at which point at least one of the VCs pulled out of the IPO completely, preferring to hold their shares.
Anyway, despite these incredibly bullish indicators, my advisor didn't like the IPO.
It was very complicated to participate in too; you couldn't go through your normal channels. I think the complexity would be easily manageable by a modern UI/UX pro; the underlying market mechanics aren't that difficult. But hitting '90s era UI/UX with unwilling brokers was a tall order.