A lot of Gary Kirke’s stories about business breakthroughs begin in bars. A favorite hangout during his early years at Continental Assurance in Chicago was the Brokers Inn. “After work,” he said, “I used to go down to the Brokers Inn and drink at the bar with Howard Reeder and Charlie Finley. I was only 21 years old and people would ask me, ‘How do you know Howard Reeder?’”

The answer was that Reeder, the head of Continental Assurance (which would become CNA Group in 1965), had been a protégé of Gary’s father when Ben Kirke ran the Des Moines office of Lincoln National in the 1940s and ’50s.

“But working in the mailroom turned out to be the best thing I ever did. I was delivering mail to all the executives, so I got to know them all, and later on when I moved around and worked in various departments, they already knew me.”

From the mailroom, Gary was able to learn about the whole company. It was a great experience for someone who eventually owned a brokerage that leaned heavily on direct mail solicitations. It also put him in touch with people who later would help him grow his business. “Those guys always got me the deals I needed,” he said.

Finley’s first client was the American Medical Association. Here’s how Gary said it happened: Finley was injured and had to have surgery. While he was in the hospital, he got into a conversation with his surgeon and asked, “What would happen if you became disabled and couldn’t use your hands?”

The surgeon said he didn’t know, but he probably wouldn’t be able to do anything. That’s when Finley explained disability insurance to the doctor, who agreed that it sounded like a good idea.

“So Charlie called the American Medical Association and signed up 20,000 doctors right away,” Gary said.

“You got 20,000 people in one sale,” Gary said. “I couldn’t sell that many life insurance policies the rest of my life if I worked through lunch, dinner and breakfast.”