Our Story
It started with a problem Tony couldn't buy his way out of.
In the mid-1990s, Tony Caldwell left a career in public service — including two terms in the Oklahoma House of Representatives — and entered the insurance business on a shoestring, joining his friend Ken Anderson's independent agency. The industry was consolidating, and carriers were shutting small independents out of the markets they needed to grow. The conventional fix was capital: buy other agencies, hire producers. Tony didn't have it.
What he had was a better idea. In 1997 he met Tom Barrett of the Strategic Insurance Agency Alliance — SIAA, then 525 partner agencies — and saw the model: independent agencies negotiating together with the scale of a national chain. In 2000 he signed on as the first SIAA master agency west of the Mississippi, and OAA was born inside his own agency. One member. Ten million in premium. Three carriers.
Twenty-five years later the network spans 180+ agencies across three states, grew at a 36.6% compound annual rate over its first 18 years,3 and has helped pioneer the playbook for captive agents becoming owners. The dream stayed the same: "Our dream is to help others make their dreams come true," Tony says, "because we know that's how we make our dreams come true."
