These people all have a lot of money and they all try to use it to influence politics, so if Benioff is so much more successful, maybe there's actually something to learn from him, such as, maybe, not wishing death on people.
As I mentioned in my first message: the startup bros weren’t particularly politically active until the last couple years. And they’ve been relatively successful since.
He likes bravado, but the startup bro faction has succeeded in the majority of political fights it’s engaged in so far. This shouldn’t be all to surprising either: a lot of these local elections are decided by a couple hundred votes. Sustained attention can have a large swing in outcomes.