EP 30: Lessons in Leadership and Legacy From Jessica Sherman of The Douglaston Companies
Description
Jessica Sherman, Vice Chair and Principal of The Douglaston Companies, discusses family-rooted leadership, community-first development and how character, accountability and partnerships shape impact in New York real estate.
Key Takeaways:
00:00 Introduction.
04:49 Family inspiration drives purpose-driven work across building, management and community.
08:39 Integrity and a strong moral compass guide decisions, relationships and long-term reputation.
13:47 Collaboration with public partners expands housing while aligning with neighborhood needs.
16:32 Policy and financing dynamics define feasibility, scale and project pacing.
21:12 Community connection elevates design choices, services and the everyday resident experience.
24:17 Proactive outreach and relationship building unlock guidance and opportunities.
25:37 Continuous improvement comes through reflection, feedback and avoiding repeated mistakes.
29:32 Reputation compounds over time through consistency and fairness.
Resources Mentioned:
https://www.linkedin.com/in/jessica-sherman-78049120/
The Douglaston Companies | LinkedIn
https://www.linkedin.com/company/thedouglastoncompanies/
The Douglaston Companies | Website
https://www.douglastondevelopment.com/
City of Yes (NYC zoning initiative)
https://www.nyc.gov/content/planning/pages/our-work/plans/citywide/city-of-yes-housing-opportunity
NYCHA Public-Private Partnerships (PACT)
https://www.nyc.gov/site/nycha/about/pact.page
https://www.principles.com/
“Start with Why” by Simon Sinek
https://simonsinek.com/books/start-with-why/
“The Psychology of Money” by Morgan Housel
https://www.amazon.com/Psychology-Money-Timeless-lessons-happiness/dp/0857197681
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