It sounds like a startup company with inexperienced people across the board. The red flag is the expectation of unpaid work and a 'free' vacation day, which amo

It sounds like a startup company with inexperienced people across the board. The red flag is the expectation of unpaid work and a 'free' vacation day, which amounts to nothing because of the 'unlimited' vacation policy. The other things are garden-variety mistakes. However, if there are 30 people starting in a cohort, then it sounds like a larger company, in which case everything is beginning to look like poor management across the board. If you have a bad gut feeling about your boss, trust your gut and look elsewhere if you have a choice.