Three stories from back when I was running an outsourced CFO firm and getting pulled into other people's messes.

The first one is a "CFO" who told a startup they had nine months of runway when they actually had three. The second is an exec with a perfect resume who locked me out of my own email, Slack, and bank account overnight. The third is a founder who was quietly skimming his own company while a partner at the fund covered for him.

The thing all three had in common is that the most impressive guy in the room, the one with the best title and the best resume, was the actual problem. And the title is what kept everyone from looking too hard. I kept being the outside guy who got brought in to say the real number out loud, and the number itself was almost never the surprising part. It was always a person who knew and had a reason to s ...