Shortstack was founded in 2021.
It is a collaboration between two real estate developers.
anna mackay
JESSY LEDESMA
JESSY LEDESMA
Co-Founder
Jessy Ledesma is the Founder of HomeWork Development and Co-Founder of Shortstack Housing.
Jessy founded HomeWork in early 2021 with a vision to build a new model for missing middle housing. Since 2007, Jessy has transacted $230M in development volume across 20 projects. This includes over 650 affordable housing units and 200,000 SF of commercial developments.
Jessy currently serves on the Home Forward Board of Commissioners and was a founding member and chair of the ULI Portland Chapter Women’s Leadership Initiative (2019-2024). She holds a degree in Architecture from the University of Oregon.
ANNA MACKAY
Co-Founder
Anna Mackay is the Founder of Sister City (f. 2020) and Co-Founder of Shortstack Housing.
Anna has been contributing to Portland's built environment for nearly two decades. Anna's placemaking prioritizes community benefit and achieves it through the inclusion of crowd-investing, bold public art, and affordability. Her projects range from beloved food halls to radically affordable housing. She explores the intersection of public and private partnerships to deliver buildings that are equal parts beautiful and attainable.
Anna's development practice marries the spirit of creative collaboration with technical expertise. She is invested in the proliferation of developers who are more representative of their communities.
Anna holds a degree in Architecture from the University of Virginia.