Randy Shiozaki

Randy Shiozaki is the founder of the Willoughby Society, where he blends technology expertise with a passion for supporting artists and preserving historical archives. The organization explores innovative ways to champion human-led art in an increasingly AI-driven world. Randy sees AI as a tool to enhance creativity and cultural preservation.

Previously, Randy co-founded ListReports, a SaaS company that redefined relationship-building for settlement service providers in real estate. The company’s data-driven approach led to its evolution into Highway.ai after a successful private-equity-backed sale.

Randy’s entrepreneurial journey includes founding a media technology company that merged audio content recognition with consumer experiences, collaborating with major networks like Fox, MTV, and CBS. Earlier in his career, he launched a creative agency in Shanghai, working on branding and media formats for clients all over the world.

Randy draws on his diverse experience—building and exiting companies, pioneering media technology, and working in Asia—to drive his mission at the Willoughby Society. By blending innovation with culture, he aims to inspire and support the artistic community while preserving its legacy.