I am honestly surprised there is not more ultra-targeted advertising to either ultra-high-net-worth individuals, or to individuals in key positions within large institutions.

E.g., there are ads all over the DC Metro for huge defense-sector projects, like a particular company's bid for fighter-jet engines. They're spending huge sums on these ad buys, which presumably are aimed at only a handful of people who actually have influence over the procurement process. Similarly, there are lots of ads in trade publications aimed at buyers, of whom there might only be a few dozen in a particular niche industry. It only follows that this is, the ad-buyers believe, the best they can do.

But consider what they could do if they really drilled down and tried to target the specific individuals with control over the money: instead of a shotgun ad buy in the subway or in a magazine, they could build a model of that person's life -- where they go, what they buy, what makes them happy (at least, happy enough to be externally perceptible), what pisses them off enough to complain about it, etc. And then you could Skinner-box the living shit out of them.

In the limiting case -- I'm thinking here of someone who works in government procurement; maybe not even the person who makes the ultimate decision, but the person who builds the briefing slide deck for the person who makes the decision, or the advisor, or the advisor's assistants -- for the price of a big ad buy, you could probably hire up a bunch of unemployed acting students and follow them around for a few months. Every time something good happens to the contract or in negotiations, make sure they have a really, really good day. Someone offers them a seat on the train, or lets them into traffic, anonymously buys them coffee, randomly compliments their shoes, pulls out of a parking space just as they're looking for one... every little thing just goes right. And every time the negotiations aren't going well, make sure they have a really shit day. They get cut off in traffic, get coffee spilled on them, yelling everywhere, can't even get the machine they want at the gym, takeout place is closed for a special event, rental house down the street is having a loud all-night party again... Pretty soon you'd condition them that when things go right for your company, and when things move fractionally closer to the outcome you want, they have a good day. And when they don't, they don't. It's advertising by gaslighting, basically.

AFAICT the only reason this isn't done is because nobody's really tried it yet, perhaps out of some remaining shred of propriety. I'm not even sure it would be illegal, necessarily (you'd have to get some lawyers to work around anti-stalking laws, I suppose, but they are pretty weak in a lot of states). While there's nothing that would have prevented you from doing this 50 years ago with an army of P.I.s to gather the information, now you could build up all the dossiers in advance and have them ready to go, pretty much turnkey, on anyone you thought you might want to influence. Or, more likely, a company could set all of that up and then offer it as an arms-length service to other companies looking to achieve a particular outcome.

No reason, I suppose, why it might not be going on right now.