Cowled Insurance

About this location

A few stories people tell about this place

1. In an old neighborhood of Chicago stood Cowled Insurance, its sign always casting eerie shadows on the street. One night, after closing hours, a delivery driver noticed something odd: a small dog frantically barking outside the office door. Curious, he peered through the window and saw only empty desks and a flickering light. Suddenly, a voice from behind said, 'Can I help you?' Startled, the driver turned around—only to see a friendly-looking cat wearing a tiny cowl. The cat smiled and added, “Welcome to our late-night insurance meetings.”

2. At night, when Cowled Insurance closed its doors, a delivery driver swore he heard someone whispering from inside: ‘Another policy sold.’ Curious, the delivery driver returned late one night with a flashlight. Inside, everything seemed normal—until he overheard an old man muttering in the back office: ‘Another premium paid.’ Turned out it was just the owner’s parrot, trying to help sell policies.

3. At dusk, in the quiet suburbs of Boston, a young boy walking home noticed something odd outside Cowled Insurance. His dog started barking furiously at a shadowy figure lurking near the entrance. Curious, he peered closer and saw only an old man with a hood pulled low over his face. The next day, everyone in the neighborhood was talking about it—except no one could remember what exactly they’d seen. Turns out, it was just a regular guy delivering packages for UPS.

4. At dawn, in the sleepy town of Santa Fe, a stray dog began visiting Cowled Insurance every morning. It would bark insistently outside the door until someone opened it, then dash inside and peer around curiously before bounding back out again. One day, an old delivery driver noticed the dog and decided to bring it some bones. Soon enough, the canine became a regular, sitting patiently on the porch while his human friends inside discussed policies and premiums. To everyone’s surprise, business picked up—maybe because customers liked seeing the friendly pooch waiting outside.