The reality is, people are taking millions of dollars to build an app, and it takes them many months to push it out. With only one dev, me, my cofounder and I lived off of < 25K for a year, and built up an app with +70K users. That's a lot of wasted time and money on the people who took millions in funding and haven't hit millions of users. I don't know what 1999 was like, but it's true that tons of startups raised money, were slow to validate, and are now are dying.
With regards to Highlight I imagine they will likely die before doing that or give up on the original hypothesis. Statistically speaking that is most likely. I was trying to be helpful, and as you mentioned you can just as well list off a list of startups so I'm not sure focusing in on one example is that useful as I can just as easily name more.