the possibly naive pr{e,o}mise of the early web was that it would be a place for people who created content for the joy of creating it to share said content with people who would discover the delights of gatekeeper-free media consumption. "premium" content, that people were trying to make a living from selling, could go behind a paywall or into subscriber-only emails, the way books and magazines worked pre-web. sadly…
Married to Business model not their consumer: most of the content producer (music, video, tv, books, news etc) were trying to hold out with their old business model (think: buying album only or newspaper subscriptions). As new platforms emerged consumption patterns changed yet the model did not changed. In a leaked email by Jobs to Murdoch regarding e-books publishing, Jobs clearly warned that if books were not made available at price points, delivery methods and platforms to today's consumer behavior, we shouldn't be surprised to see a Napster moment in publishing industry. Those who have held stedfast in their old ways have suffered. Only now we can see some revival of music thru subscription via Apple Music and Spotify--but it took years and a lot of failed startups to get here.
Ads: Head in the sand moment: Having worked in this industry i see a few common occurrences: 1_ ad agencies have made it a point not to learn about emerging tech, actively invest in them or be the agent of innovation. Just like content industry they are happy to pick u 15% of cut from the buyer and the seller of ads, just b/c they can 2_ over last 20 years there is a steady increase in marketing budgets as a % of revenue by everyone in some cases up to 20%. Obviously CEOs will expect the CMOs to be accountable and present a ROI model vs the traditional 'sunk marketing costs'. Thats where data came into play. However, in actuality data is really being applied with very little thought.
Combination of laziness and apathy are some of the reasons for shitty ads.
What i find it intriguing if the quality of ad content is good and delivered in a meaningful ways then people wouldn't mind it (eg: Super Bowl ads).
But then again it takes a lot effort and thinking. I'm however, hopeful.