I’ve learned how to get under rich people’s skin and in my free time when I’m bored I harass them. It’s an unguilty pleasure of mine. It brings me great joy to see a multimillionaire or a transphobe so pissed about something I said that they complain to spez to get me banned.
I also just have a general interest in security and privacy, sometimes I just do things like spam an ad site to see how long it takes to react.
They have big egos. You need to be sure they’re an avid poster and will respond to what you say. There’s also the public aspect, they don’t like having something awful they’ve done brought up in a community they like. You can set up a bot to post things like “Hey remember that time you sexually harassed a woman 20 years younger than you and a court ruled against you” as soon as they post an AMA so it’ll be the top comment. Reddit really hates when you use bots like this and will likely remove the comment after it gets a lot of attention which further inflames other people against the target.
A lot of this requires practice to get good at heckling. It’s all a case by case basis. You should always be aware of your audience and what the audience finds most unacceptable about someone’s behavior.