Anna Mackay
Founder, Sister City
Anna has spent her career innovating and field-testing concepts of social impact in real estate. She led the first Regulation A crowd-investing effort for new construction in the United States ($1.5M, the Fair-Haired Dumbbell) and raised a tranche of crowd-invested equity from everyday Oregonians for a homelessness project in just 68 hours ($300,000, Jolene’s First Cousin). She has pioneered new models of development that emphasize non-displacement and affordable retail (Rocket Empire Machine). Her buildings achieve affordability and community buy-in through the utilization of crowdinvesting, internally-subsidized financial models, and bold public art.
Anna founded Sister City in 2020. Every Sister City project reevaluates standard development practice to emphasize a just balance of equity—social, environmental, and financial. Her current projects include the Annex, Portland’s first affordable housing project to utilize cross-laminated timber and the development of replicable workforce housing units called Shortstack alongside Jessy Ledesma of HomeWork Development. Shortstack is a replicable, mass timber, “missing middle” housing solution that will initially pilot 70 units on four sites in Portland, Oregon. It will welcome its first tenants in 2023.
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