My guess is the economics of news on the internet were unknown at the time, so people invested in it (willing to eat losses in short term) thinking ad supported

My guess is the economics of news on the internet were unknown at the time, so people invested in it (willing to eat losses in short term) thinking ad supported news could take off and paid for quality journalism. Now no one is that naive and we have just clickbait factories. Another possibility is due to success of newspapers, the craft of journalism was still known and practiced with skill, these days it's basically just fresh college grads without any on the job training cranking out stuff they read on social media and whatever a PR rep emails them that morning. But that's also related to the economics.