For decades, developers chased returns, and accidentally designed community out of our cities.
In this episode of ROI Masterclass, Christopher Woodruff, CEO of Woodruff Brokerage Company and The Cotton Companies, explains how modern development created isolation, urban blight, and disconnected places — and how servant leadership can reverse it.
From traveling to South Korea with city leaders, to rebuilding neglected blocks through adaptive reuse, Christopher breaks down why long-term ROI comes from asking one question first: What does this community actually need?
We explore experiential design, secondary and tertiary city investing, sustainable planning, and why great development isn’t just financial, it’s human.
If you’re a developer, investor, or city builder, this conversation will change how you think about growth.
:stopwatch: YOUTUBE CHAPTER TIMELINE (Clean + Clickable)
00:00 — Why Economic Development Drives Real Estate Success
03:30 — Traveling to South Korea With City Leadership
07:10 — Entrepreneurship vs Servant Leadership
11:20 — How Cities Are Really Built (And Broken)
15:40 — Developers Created the Suburban Problem
20:10 — Strip Malls, Parking Lots & Lost Community
25:10 — Adaptive Reuse as Community Repair
30:00 — Why Community Is the Missing Asset Class
34:30 — Experiential Design & Cultural Connection
39:20 — Why People Crave Community Again
44:10 — Jane Jacobs, Density & Safer Cities
48:50 — Secondary vs Tertiary City Investing
54:10 — Long-Term Developers vs Short-Term ROI
59:20 — How Design Decisions Multiply Returns
1:04:30 — Sustainability, Energy & Operating Costs
1:09:40 — Why Aesthetics Affect Human Psychology
1:14:40 — Planning for Relevance 20 Years Ahead
1:19:30 — Where Smart Developers Are Investing Next
1:24:50 — Three Rules Every Developer Should Follow
1:29:30 — Servant Leadership as a Development Strategy
1:34:10 — Final Advice for Builders & Investors
#RealEstateDevelopment #CommunityDevelopment #ServantLeadership #RealEstateROI #AdaptiveReuse #UrbanDesign #Placemaking #SustainableDevelopment #CommercialRealEstate #DeveloperMindset #ExperientialDesign #FutureOfCities
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