Kurt Donnell left M&A law for digital media and became the first CEO of Freestar, helping scale it into a global publisher monetization business. Now the open web faces a harder test: declining search traffic, AI answer engines, fragmented AdTech, and advertiser dollars moving to simpler closed platforms. Can radical transparency restore trust, what publishers should demand from AI companies, and whether Freestar’s new pubOS creates real leverage—or merely manages declines.