Simon Windell grew up in Spokane, WA, and studied Physics at Seattle University, where he conducted undergraduate research in fluid dynamics. That early exposure to scientific inquiry shaped his approach to problem-solving — starting from first principles, experimenting, and iterating toward practical solutions. After college, he began his career as a technical software and systems engineer at a global consulting firm, later moving into Corporate Operations where he learned how to run complex businesses, manage multidisciplinary teams, and deliver large-scale solutions across borders.

In 2019, reading Evicted sparked an interest in housing that soon became a calling. After moving to Okanogan county in 2016, and then the Methow Valley in 2020, Simon left the corporate world and joined the Methow Housing Trust, where he discovered the importance of community ownership and the Community Land Trust model. Simon is the Director of Finance for the Lahaina Community Land Trust, the CFO for the Methow Housing Trust, CFO for the Olympic Housing Trust, and advises CLTs, ROC-affiliates, nonprofits, municipalities, and developers across the west. His work focuses on building operational systems, financial models, and mechanisms for permanence that instill confidence in the community return of major investments in non-market housing. Simon also serves as a Planning Commissioner for the Town of Winthrop, Chair of the Okanogan Community Action Council, and Treasurer of the Northwest Community Land Trust Coalition.