The trick is to speak to him last.
Weak CEO. Frat boy founder hires his frat boy friends; together they create a trainwreck organization wracked with disloyalty, intrigue and incompetence. An atrociously mean-spirited workplace, where competent people keep their heads down while the founder/CEO's posse strut and jostle.
I build their next-generation processing engine and the organization to manage it; then turn down the CTO role when offered. No-one with alternatives would work there voluntarily.