Progressive Insurance is the friendly insurance company that somehow managed to make the word “insurance” a little less scary! Founded in 1937 Progressive has become a household name, primarily due to its quirky commercials featuring the ever-enthusiastic Flo. But let’s face it no one actually understands what insurance is until you need it. So, think of Progressive as that friend who always shows up with snacks at your boring meetings (you know the one who brightens up your day but you’re still not sure if they’re really that helpful).