Employees working hard at start ups have no desire to destroy the company culture by getting shit-faced and damaging their company brand; it’s rarely done out of malice. It’s done because no one told them they couldn’t.
CEOs make strange requests. There's stories of Office Managers and Executive Assistants being asked to do bizarre things only to have the CEO decide it wasn't necessary after all. It can be truly infuriating.
I'm well known for firing cleaning crews that don't meet my standards. If I am paying you to clean the office, I expect the office to be cleaned.
I'm not at all a fan of "Best" because it's unfinished. Best what exactly? I have no idea what you're trying to say. I'm never happy to see an email signed off with "Best", I think it's lazy and unimaginative.
A former employer of mine continues to host massive events multiple times a year. It's not unusual for me to hear about former co-workers heading off to see Jay Z or Kendrick Lamar performing a concert exclusively for employees.