Additionally, this is survivorship bias. His emails sounded very professionally immature and while this companies leadership may have found it endearing, I could easily see other groups of people finding it off putting.
What this guys effort signaled to me is that he’s probably annoyingly overeager, but willing to basically do whatever I want him to do whenever and however long I want him to do it. In other words he’d be a good lackey.
If you want to shamelessly signal that you’d be a decent lackey for an obscure to medium startup this may be decent advice. And this may not be a bad thing, I know Casey Neistat’s employee Jack Coyne did something similar and it opened up a lot of doors for him.