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Sibley is a social entrepreneur working to help solve the housing and homelessness crises in Monterey Bay Region and northern CA. He is currently the President of New Way Homes, a non-profit that operates an impact investment fund to spur new workforce and affordable housing development. He co-founded the 180/2020 Initiative in 2012 that has housed over 1000 chronic and veteran homeless individuals, has served as the Treasurer of the Housing Matters, and leads the renovation of the historic Evergreen Cemetery. Previously, Sibley was a founder of two technology companies, StreamSage and The Electric Sheep Company, which were repeatedly recognized as highly innovative, including by two Technical Emmy Awards, the MIT Technology Review, and R&D grants and contracts from six federal agencies and many Fortunate 500 companies. Sibley lives off the grid in the Santa Cruz mountains and has become almost as obsessed with all things related to cycling as he has with how to improve housing affordability.