One of my first jobs as an apprentice was in a family run shop (not sign related). The owner that ran the day to day operations used to walk around and hold his stomach every day and just moan out loud. When you'd ask what's wrong, he'd tell you how his ulcer was killing him because he was so worried about the money and how to pay the bills. It was a daily complaint.
He bought a $400,000 house, where the average home at the time, was about $200,00, pulled up to work one day in a 30 foot boat, being towed behind a brand new truck big enough to pull it.
I determined at that point in my life, I'd never believe another owner that told me they were going broke until I saw their behavior match it.