Our Story
OAA began as one agency's answer to the carrier-access problem.
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.
In 1997 he met Tom Barrett of the Strategic Insurance Agency Alliance (SIAA, then 525 partner agencies) and saw a different route: 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 with one member, ten million dollars in premium, and three carriers.
Since 2000 the network has grown to span 170+ agencies across three states2 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."
