What if our cities weren’t just places we lived, but places that made us feel alive? In this episode, we welcome back Coby, an urban planner, developer, and author of Building Optimism, to talk about how we can move beyond pessimism and reclaim the built environment. We dive into the philosophy of traditional urbanism versus traditional architecture, how to balance art and economics in development, and why optimism in city building isn’t just wishful thinking—it’s already happening.

Coby shares how his latest project integrates affordability, beauty, and human-scale design, and why zoning reform is beginning to shift the landscape of American cities. We discuss why preservation alone isn't enough, how small developers can create lasting impact, and why the best cities aren’t built overnight—they evolve, adapt, and improve over time. If you’ve ever wondered why some places feel right and others don’t, or how we can design spaces that actually serve human beings, this episode is for you.

TAKEAWAYS

Great places aren’t about height or style but about how spaces are formed. Streets, plazas, and courtyards dictate how we experience a city more than the aesthetics of individual buildings.

Traditional architecture isn’t about copying the past; it’s about principles that create beauty, durability, and livability across cultures and time periods.

Keeping historic buildings is important, but we should also be building new ones that are worthy of being preserved in the future. Fear of losing the past shouldn’t stop us from creating great new places.

The best cities have a mix of housing that allows people of different income levels to live side by side. Segregating wealth or poverty harms economic mobility and community vitality.

The hardest part of building great places isn’t the architecture—it’s getting the financing. Small-scale, human-centered development struggles to compete with big box projects, but that can change with the right approach.

Building better cities isn’t a fantasy—it’s already happening in pockets across North America. The real challenge is scaling those successes and proving that beautiful, walkable, thriving communities can be the norm, not the exception.

CHAPTERS

00:00 Exploring Urban Beauty: A Vision for Cities

01:32 The Intersection of Urban Planning and Development

03:58 The Journey to Writing 'Building Optimism'

10:02 The Current State of Urbanism: A Turning Point

18:41 Traditional Urbanism vs. Architecture: Finding Balance

22:59 The Role of Preservation in Modern Urbanism

38:20 Creating a Living Tradition in Architecture

44:06 Exploring Kingston's Urban Fabric

51:04 Innovative Infill Housing Solutions

58:13 The Importance of Diverse Housing Options

01:06:56 Creating Integrated Communities

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