This is pure legal gold by Matt Levine imagining a conversation between Elon Musk and his designated “Mystery Twitter Sitter”:
Musk: If I tweet “Thursday 2 pm,” is that the sort of thing that “contain[s], or reasonably could contain, information material to Tesla or its stockholders”? No, right?
Mystery Twitter Sitter: Why do you torture me.
Musk: And surely tweeting “California” is fine? Nothing material or misleading about “California.”
MTS: I was an editor of my law review you know.
Musk: And then “Some Tesla news”?
MTS: What have I ever done to—wait, yes, obviously “some Tesla news” could be material to Tesla and its stockholders.
Musk: But there’s nothing misleading in the tweet, so you can pre-approve it, right?
MTS: Well I don’t know, depends on what the Tesla news is. What is it?
Musk: You’ll find out Thursday, lol.
MTS: What if, instead of doing this, you just went to bed.
Musk: Show me what in these three tweets is illegal or misleading.
MTS: Look, as your lawyer, I am telling you that this seems like a bad idea, and you should at least wait until after your contempt-of-court hearing to do anything that might look like a violation of your settlement with the Securities and Exchange commission.
Musk: Nope! I am a smart guy and I like to get into the details of every aspect of my business. I second-guess expert engineers all the time, and often it works out for me; I’m not going to do whatever you tell me just because you are a lawyer. I think these tweets are fine. If you don’t, you have to explain to me, specifically, how they violate the settlement.
MTS: The world is not as black and white as many tech founders wish it was, and the legal system is not just a list of unambiguous written rules applied in a mechanical fashion. Whether you like it or not, regulators and courts operate in large areas of discretion; they have lots of ways to make life more difficult for you and for the company that you manage as a fiduciary for others, and they are used to being treated with a certain amount of deference by the people they regulate. Here they have you dead to rights on a technicality—you didn’t get your “500,000 cars” tweet pre-approved, as you promised you would, and it had to be corrected—and how they respond to that will depend on your overall attitude and behavior. My job as a lawyer is not just to look up rules and show them to you; it is to make predictions, grounded in research but also in experience and a certain professional connoisseurship, about how officials will react to particular fact patterns, and to advise you on the wisest course of action in shaping their reaction. (This is sometimes called “legal realism.”) My expert advice to you is that the benefit to you, and to your company and its workers and shareholders, of sending out these inscrutable late-night tweets is very low, while the risk of further antagonizing the SEC and the courts seems pretty high. I am not giving you a formal legal opinion that it is illegal for you to tweet “California.” I am just telling you that it’s dumb.
Musk: Well are they going to put me in jail for sending these tweets?
MTS: I mean, probably not, no.
Musk: I have a big drill you know.
MTS: I know.
Musk: That’s a kind of legal realism too.
Who Can Say What California Means?
Lawyers working in any complex, regulated space have a version of this conversation every week.