I worried when Google bought DoubleClick many years back if Google would become as bad as DoubleClick. I don't think we can point fingers at any one thing precisely, but that did seem like an omen at the time.

I think the problem with ads on the internet is that it will always be a race to the bottom. Ads on TV and in newspapers/magazines have scarcities in play to somewhat help manage them. Ad space on the internet has never been scarce.

The ad companies (Google and Facebook especially) see themselves as somehow unbiased market platforms, and I think we are coming to point where the lack of scarcities leaves "neutral" platforms vulnerable to very cheap "attacks". I worry that ad platforms need to exert a lot more editorial control in the face of that and/or start building a lot more artificial scarcity into their platforms, and I don't think any of them are appropriately incentivized to do that.

I also worry that Google and Facebook's ad spaces are content spaces: search ads at the top of search results, and sponsored "posts" that have like/share/comment abilities. I think that also requires a custodianship and a moral obligation to editorially control those spaces that neither Google nor Facebook have thus far been inclined to take enough responsibility for. Facebook especially, when liked/shared ads graduate to "real" viral content, entirely blurring the lines between ads and content and giving direct power to cheap micro-targeting attacks without having some editorial immune system to help avoid the worst memetic viruses. (Facebook claims to want to do better, but their fiduciary responsibility incentivizes them not to treat ads as user hostile infection points.)

> I worried when Google bought DoubleClick many years back if Google would become as bad as DoubleClick.

Me too, but not so much about the content ("ads is ads", I used to think), but about privacy and the relentless tracking that DoubleClick was doing. And oooh boy, did that omen ever come true.

Another thing was the moment when I realized the implications of having a giant Internet-wide ad-network implemented in the form of injected third-party javascript. I mean, at first it seemed real clever. This wasn't a big thing back then, just yet. Originally ads were just clickable image links with an affiliate code in the GET parameter and http-referer tracking (which already provides an advertiser way more info about their audience then a printed ad in a magazine would, so yes that is more than sufficient for advertisers who honestly want to advertise instead of spying on people).

It's a miracle that over the existence of AdSense, nobody ever managed to XSS the entire Internet. Even if that can be attributed to the AdSense team awareness of their unique position of responsibility and engineering quality control or something; We still dodged a bullet with that one, because it just so happens that it was the Google that came into control of the largest XSS vector in history. But having quality control and a culture of responsibility didn't cause becoming the largest and gaining control (it just means they got to keep it, because it hasn't gone horribly wrong--for which we are lucky). A while back I read a comment on HN arguing (though I'm not sure if they realized) that whether something is a "good product" depends more on how well it is marketed (and therefore finds its way to people that can use it) than it depends on the quality of the product. That's horrible, but like too many horrible things, also true in some sense. So it just so happened that the ad-network that was marketed best and became one of the largest and most successful, also happened to be one that was of sufficient quality to not break the Internet.

Wasn't the seminal moment when Google bought Doubleclick in 2007?