Derek Fleming

Senior Advisor

Derek Fleming is a nationally recognized real estate and economic development leader who structures catalytic public-private partnerships and leads master planning and development strategies that protect culture, align capital, and generate durable economic power.

With more than 20 years of experience across public agencies, private equity, and entrepreneurial development, Derek operates at the intersection of policy, finance, land use, and community identity. He advises cities, institutions, and mission-driven developers on the repositioning of catalytic sites, creative and cultural districts, retail corridors, and food-based economic ecosystems, translating vision into implementation-ready strategies that unlock investment while safeguarding community ownership.

Derek’s work spans highest-and-best-use analysis, capital stack structuring, entitlement strategy, retail and tenant ecosystem positioning, governance design, and long-term operating frameworks. He is particularly skilled at sequencing public and private investment to de-risk catalytic projects, align incentives, and establish financially viable district-scale redevelopment models. His approach ensures that master plans are not aspirational documents, but executable roadmaps tied to capital strategy and measurable economic impact.

Central to his practice is the advancement of Cultural Capital as a development platform, positioning neighborhood identity, heritage, creative production, and local entrepreneurship as economic infrastructure rather than peripheral assets. Through this lens, Derek has led redevelopment strategies in historically marginalized communities that elevate cultural districts as engines of tourism, small business growth, and generational wealth creation while protecting existing residents from displacement.

In addition to his advisory work, Derek brings hands-on development experience, having led the adaptive reuse and repositioning of culturally significant assets into high-performing commercial and community anchors. This dual-sector fluency allows him to bridge institutional priorities and market realities, structuring partnerships that leverage public investment effectively while meeting private capital performance expectations. His experience managing empowerment zone lending portfolios and navigating complex entitlement environments equips him to guide clients through the full development lifecycle, from early visioning and district strategy through capitalization and implementation, ensuring projects are financially durable, politically viable, and culturally grounded.

Derek’s 12 years of public sector experience focused on neighborhood revitalization and economic development. At Empire State Development, NY State’s economic development agency, Derek managed a NY Empowerment Zone public lending portfolio of $60 million for real estate and business development transactions in some of New York City’s most economically marginalized neighborhoods, in particular Harlem and the Bronx. During his four years as Project Manager for the San Francisco Redevelopment Agency, Derek successfully led a team through the entitlement and re-zoning of the 300-acre underdeveloped Mission Bay brownfield site, leading to the development of over 1,500 affordable housing units as well as retail, commercial, hotel, and market-rate housing.

Derek holds a bachelor’s degree from the University of California at Berkeley and an MBA from Kellogg School of Management. In addition to his role as Senior Advisor at HR&A, Derek is a senior board member of the Neighborhood Charter School Harlem & the Bronx.