@brainwane this is such a fun question, maybe I'll try to read the IRS section 501 rules after I finish Robert's Rules of Order.

As a person in the world, I feel like if I can decide not to buy from companies who e.g. donate to Omarchy, there's no reason I can't decide TO support companies who donate to things I like?

But, if you are involved with the charity's operations, the rules are different.
I know that you can conduct certain types of fundraising raffles as a charity but which types are OK is different in different states. https://www.irs.gov/charities-non-profits/stay-exempt/maintaining-501c3-tax-exempt-status-course-video-transcript (federal resource roughly equivalent to a Colorado training I once took) seems to cover related ground on "private benefit"/"inurement"/"charitable solicitation" and it definitely applies to officers, directors, key employees of 501c3 organizations in the US. This is not quite inurement, it's more a kind of solicitation imo, but maybe that's a starting point?

@brainwane "actual malice" will probably matter a lot to the answer to this question. The legal term more than the general squishy thing that "malice" means in normal human languages. or I guess I really mean the criminal law equivalent, whose name I am forgetting (would it fall under mens rea?)

That is: I suspect any such crime would hinge on unauthorized use of a computer system that is done *knowingly* and with intent to do something harmful to the operator or society at large. Which in turn would probably depend on the query "do you mean it?" when you say you would be more receptive, or is it a tactic to manipulate a computer system?

Not saying that intent alone is enough to make a case here for something like CFAA, but the relevant laws generally (AFAIK) have a lot of "knowingly" and "intentionally" sprinkled in them¹

The actual malice judgement is *surely* going to be impacted by if you are associated with the charity and might thereby directly benefit. I would say it's best not to do that with any such org you're associated with. The occasional $50 or whatever is worth far less than the liability² incurred by even the chance of ending up in court over it.

I do think federal law dominates here in the age of LLMs. The likelihood that your interaction doesn't cross state lines is basically zero and federal jurisdiction is funky with wires. It's possible there could be splash damage from state/city laws depending on how they are written, I don't know the first thing about NY(C) law.

---

¹ e.g. 18 U.S Code § 1030(a)(4): «Whoever—...knowingly and with intent to defraud, accesses a protected computer without authorization, or exceeds authorized access…»

²I imagine the legal fees for something that gets dismissed in pretrial would still sum to more than you'd ever get donated if your hit rate is even as high as 10/day? maybe I'm being pessimistic, but court is expensive and charities don't have a lot of cash on hand as a general rule.