- December 6, 2025
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Serial entrepreneur Steve Herrig has made millions mostly by being in businesses in and around insurance for some 35 years. He started his career — after a short stint painting houses — selling insurance in his early 20s.
But back in the mid-2000s, when he ran a human resources outsourcing entity in Sarasota and Manatee counties, one side of the industry specifically irked him: insurance. His peeve was over firms that underwrote and provided workers' compensation insurance for Herrig’s sector, professional employer organizations.