I recently made a crack on Twitter when I was served an ad prior to watching a video on YouTube. The ad urged me to sign up for Disney+ to check out season 2 of “The Mandalorian” - and I asked whether this represented AI, machine learning or computer vision.

It was a bit of a cheap shot - there are explainable ad targeting mishaps on the web all the time. But then I was served the ad again. And then again.

It’s really no big deal- until you consider that:

-I signed up for two years of Disney+ right when it launched

-I have a Gmail account and a YouTube account, both of which are managed by Google (which is a large computery company)

-I had already completed season 2 of The Mandalorian (OMG THE ENDING!)

-I have conducted probably 4,000 searches on Google and YouTube over the past few years exploring fan theories just on Rey’s parents

So you’d think that between Disney and Google, they could get this sort of thing right.

Again, this is hardly a big deal - ad targeting is just one aspect of the potential of all this amazing data and tech at brands’ fingertips. But it made me think. Because I’d also just seen and read multiple presentations on how AI is set to revolutionize all of media and advertising. As I have for at least five years.

I remember writing a story in 2016 on how IBM’s Watson Supercomputer was going to start delivering banners ads that would literally speak to consumers, asking them intelligent, informed questions or simply providing users information as they browsed on by.

Maybe it’s just me - but have you had a conversation with an ad lately?

Again, that’s just one product that perhaps never took off. The bigger question is - take a spin around the open web when you have a moment - does it feel more ‘intelligent’ to you? Uber-personalized, with just the right content and messaging depending on your mood, history, time of day, all that stuff? Have the machines been learning you as you proceed on various customer journies?

It feels past time to ask, when it comes to advertising, when does AI stop feeling so artificial?

A big caveat here: clearly the tech titans use forms of AI to run many of their ginormous services (Alex Kantrowitz’s book ‘Always Day One’ has a great section explaining why the FANG companies eventually had to incorporate AI to achieve scale).

And if you’ve ever spent time on Instagram, you know the potential of an ad/content system that is scary good and getting to know a person and showing them random products they’ve never heard of that they totally want to buy. (like a toy that supposedly teaches your kids to code, which I almost bought).

Of course, over 3 billion people use one of Instagram's parent company’s apps each month, and the Facebook family has upwards of 7 million advertisers to machine learn from - so it’s not a fair fight vs. the rest of the web.

Still, you wouldn’t know that based on how often you hear that AI, and CV and ML are about to kick into gear and practically serve pre-rolls into your contact lenses.

Maybe I’m wrong about all this - maybe CMOs are privy to a lot more transformative stuff going on behind the scenes. But I remember a few short years ago when Blockchain promised to absolutely reinvent advertising, media, and security and even help the Knicks win. Now, companies that were built around blockchain or blockchain-like technology actively downplay that messaging - because over time blockchain become something of an industry joke.

Seems to me that AI better start delivering or risk going down the same path. In the meantime, I’m no longer worried about the machines taking over- I’m wondering if they’ll ever be able to beat a coin at guessing a web user’s gender.