#34 Coby Lefkowitz: Building Optimism - Rethinking Cities, Architecture, and the Future of Urban Design

02/06/25 • 87 min

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

01:12:12 The Role of Capital in Urban Development

CONNECT WITH COBY

X: https://x.com/Cobylefko?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor

Website: ⁠https://cobylefkowitz.com

Substack: https://ourbuiltenvironment.substack.com/p/a-call-to-build-a-better-world

MENTIONED RESOURCES

Coby’s Book:

https://www.amazon.com/Building-Optimism-World-Looks-Better/dp/B0DJV2WLXR/?_encoding=UTF8&pd_rd_w=Q3

Patrick Sharkey’s Trapped in Place: https://www.amazon.com/Stuck-Place-Neighborhoods-Progress-Equality/dp/0226924254

Samuel Hughes’ Article: Making Architecture Easy: https://worksinprogress.co/issue/making-architecture-easy/

CONNECT WITH AUSTIN TUNNELL

Newsletter:https://playbook.buildingculture.com/

https://www.instagram.com/austintunnell/

https://www.linkedin.co...

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.

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.

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

01:12:12 The Role of Capital in Urban Development

CONNECT WITH COBY

X: https://x.com/Cobylefko?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor

Website: ⁠https://cobylefkowitz.com

Substack: https://ourbuiltenvironment.substack.com/p/a-call-to-build-a-better-world

MENTIONED RESOURCES

Coby’s Book:

https://www.amazon.com/Building-Optimism-World-Looks-Better/dp/B0DJV2WLXR/?_encoding=UTF8&pd_rd_w=Q3

Patrick Sharkey’s Trapped in Place: https://www.amazon.com/Stuck-Place-Neighborhoods-Progress-Equality/dp/0226924254

Samuel Hughes’ Article: Making Architecture Easy: https://worksinprogress.co/issue/making-architecture-easy/

CONNECT WITH AUSTIN TUNNELL

Newsletter:https://playbook.buildingculture.com/

https://www.instagram.com/austintunnell/

https://www.linkedin.co...

Previous Episode

#33 Matthew Plechan: How to Paint Masonry. The Durable, Breathable Beauty of Mineral Stains.

Most Americans think painting brick is as simple as grabbing a bucket of latex or oil-based paint, but this common approach can wreak havoc on your home–and is uglier to boot.

In this episode, I sit down with Matt Plechan, the founder of Mineral Stains. We dive deep into the art and science of finishing brick with mineral stains like limewash, potassium silicate and sol silicate.

These centuries-old techniques are not only more durable and beautiful but also allow your brick to breathe, preventing costly damage.

I talk to many people who go to Europe, see a beautiful color, and try to color match it at home on stucco or masonry. It doesn’t turn out the same. Why? It’s not the same paint!

But it can be.

If you are thinking about painting masonry, listen to this episode! And while there are other US based suppliers, Matt at Mineral Stains is an excellent source who manufactures in the US and will help you find the right product for your project!

TAKEAWAYS

Latex acrylic paints are unsuitable for masonry, while mineral stains bond with masonry for enhanced durability and a natural aesthetic.

Potassium silicate offers better longevity than lime wash, while sole silicate works effectively on previously painted or coated surfaces.

Mineral stains are eco-friendly, made from natural pigments, and provide vibrant, non-toxic finishes with a timeless, breathable quality.

CHAPTERS

00:00 Introduction to Masonry Painting Challenges

02:49 Understanding Mineral Stains vs. Traditional Paints

06:30 Exploring Types of Mineral Stains

10:56 Comparing Lime Wash and Potassium Silicate

18:30 Application Techniques for Mineral Stains

32:28 Best Practices for Exterior Application

35:37 The Importance of Primer in Painting

40:49 Cleaning and Preparing Surfaces for Painting

45:33 Best Practices for New Construction Painting

52:35 Application Techniques: Spraying vs. Rolling

57:49 Interior Painting: Natural Finishes and Techniques

CONTACT MATTHEW PLECHAN AND MINERAL STAINS

Website: https://mineralstains.com/

Instagram: https://www.instagram.com/mattplechan/

Facebook: https://www.facebook.com/mineralstains1

Matt’s Linkedin: https://www.linkedin.com/in/matt-plechan-94a18172

MENTIONED RESOURCES

https://masonrymagazine.com/Default?pageID=2362

https://voyagejacksonville.com/?post_type=interview&p=91151

https://www.fosterandpartners.com/projects/global-home-of-the-pga-tour

https://youtu.be/OIWKKjPj5PI

https://youtu.be/cojGgH-79u4

CONNECT WITH AUSTIN TUNNELL

Newsletter: https://playbook.buildingculture.com/

https://www.instagram.com/austintunnell/

https://www.linkedin.com/in/austin-tunnell-2a41894a/

https://twitter.com/AustinTunnell

CONNECT WITH BUILDING CULTURE

https://www.buildingculture.com/

https://www.instagram.com/buildingculture/

https://twitter.com/build_culture

https://www.facebook.com/BuildCulture/

Next Episode

#35 Moses Kagan: Building Generational Wealth with Generational Assets - "Indefinite Holds" in Real Estate

Moses Kagan has a unique take on real estate development and investing – and he’s influenced my thinking substantially over the past couple of years.

He is a highly successful syndicator, investor and developer with over $200 million in assets under management. He runs Adaptive Realty, having renovated over 100 multi-family buildings in Los Angeles, managing them in-house while specializing in the "indefinite hold” strategy for long-term wealth building.

He is the Co-Founder of ReSeed, a platform offering long-term GP and LP capital, along with mentorship for emerging real estate operators nationwide. He also hosts Reconvene, a highly regarded annual “unconference” for real estate operators and passive investors to connect and share knowledge. I attended last year, and it was awesome!

And lastly, he is a Twitter personality and avid blogger, sharing valuable insights on real estate and business. I highly recommend you follow him.

This is an excellent conversation about practical investment and real estate development philosophy, and I hope this conversation has as big of an impact on you as meeting Moses has on me!

TAKEAWAYS

Holding real estate indefinitely often leads to better investment outcomes than IRR-driven flipping.

Traditional real estate models incentivize risky short-term decisions, while sustainable strategies benefit both investors and communities.

Investors should focus on post-tax returns rather than pre-tax IRR, as tax considerations play a crucial role in long-term profitability.

Wealthy families and patient capital partners are more aligned with indefinite hold strategies than institutional investors.

Unlevered yield on cost and all-in price per square foot are key financial indicators for long-term real estate success.

Building direct relationships and trust at scale is essential for securing capital, especially for indefinite hold investments.

CHAPTERS

00:00 Introduction to Real Estate Development Philosophy

06:06 Understanding IRR and Its Implications

11:55 The Importance of Long-Term Thinking in Real Estate

17:59 Finding the Right Investors for Long-Term Strategies

25:50 Investing with Wealthy Families and Professional Money Managers

40:20 Understanding Capitalization and Investor Liquidity

46:11 Building Trust and Relationships in Real Estate Investment

55:41 Building Trust at Scale in Real Estate

58:01 The Democratization of Capital Raising

01:04:29 New Urbanism and Walkable Neighborhoods

01:06:00 Challenges of Ground-Up Development

01:09:03 Zoning and Building Code Challenges

01:11:57 The Impact of Bureaucracy on Development

01:14:07 Introducing ReSeed: Supporting Emerging Operators

01:17:08 The Importance of Community in Real Estate

CONNECT WITH MOSES

X:https://x.com/moseskagan?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor

LinkedIn: https://www.linkedin.com/in/moses-kagan-2638ab2/

Adaptive Realty: https://www.adaptiverealty.com/

ReSeed: https://reseedpartners.com/

Moses Newsletter: https://kagansblog.com/blog/

MENTIONED RESOURCES

The Fort Podcast Interview on ReSeed: https://www.thefortpod.com/videos/moses-kagan-rhett-bennett-co-founders-of-reseed-partners-the-y-combinator-for-re-operators/

CONNECT WITH AUSTIN TUNNELL

Newsletter:https://playbook.buildingculture.com/

https://www.instagram.com/austintunnell/

https://www.linkedin.com/in/austin-tunnell-2a41894a/

https://twitter.com/AustinTunnell

CONNECT WITH BUILDING CULTURE

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