What does it actually take to build (and sustain) one of the strongest high streets in the country?

In this episode of Behind the Lease, Brett Robinson sits down with David Waldman, a broker and developer who has spent more than three decades shaping downtown Westport, Connecticut. From historic restorations to national retail leases, David has worked both as an owner and as a street retail broker, giving him a rare perspective on how great retail districts evolve.

They discuss:

• How Westport expanded beyond Main Street into a connected “Golden Triangle”
• Why parking, residential density, and food & beverage shifted the street’s economics
• How rents moved from $60 post-COVID back into the $120+ range
• Why small spaces can command the highest rents
• The underwriting realities behind cap rates, redevelopment, and flood mitigation
• What brands Westport supports, and where it likely caps out
• Why high streets thrive on thoughtful curation, not just demand

It’s a practical conversation about retail fundamentals... place-making, risk, tenant mix, and the long arc of market cycles.

If you work on high streets, represent national brands, or invest in mixed-use downtowns, this episode offers perspective grounded in real transactions.

Brands Mentioned:

West Elm, Gap Kids, Domain, Starbucks, Sundance, Chanel Beauty, Vince, Eileen Fisher, Ryridge Deli, Express, Urban Outfitters, Lux Bond & Green, Brooks Brothers, Lululemon, Alo, Vuori, Beyond Yoga, Brandy Melville

Retail expansion often looks fast from the outside. In reality, it’s slow, local, and full of tradeoffs.

In this episode of Behind the Lease, we sit down with Jennifer Price, one of Washington, DC’s most experienced high-street retail brokers, to talk about what actually drives success on streets like Georgetown and 14th Street.

Jennifer shares how she broke into retail real estate, why DC rewards consistency over flash, and what brands misunderstand about urban storefronts—especially when inventory is tight and rents keep climbing.

We cover:

• Why DC shoppers gravitate toward quality, not trends
• How multi-level, narrow storefronts change deal math
• What rising rents mean for brands entering market today
• The real differences between high streets and shopping centers
• Why relationships still matter—but only when paired with context

Jennifer also walks through current projects in Georgetown, including large-format redevelopments that are rare for the market, and explains how brands are adapting as demand continues to outpace supply.

This is a practical conversation about how retail actually works on the ground—where constraints are real, and good decisions compound over time.

Jennifer Price — Areas of Expertise

• High-street retail in Washington, DC
• Tenant representation for national and emerging brands
• Urban storefront strategy (multi-level & historic buildings)
• Market positioning for conservative, quality-led brands
• Navigating supply-constrained, high-rent environments
• Redevelopment and repositioning of complex retail assets

Brands Mentioned in the Episode

Lululemon, Veronica Beard, Vuori, Alo, J.Crew, Aritzia, Uniqlo

Dave's Hot Chicken has grown fast, but not by accident.

In our conversation, Dannon Shiff, SVP of Real Estate, shared why the real differentiator is selecting sites for long-term success. He highlighted how Dave’s considers modern customer behavior, third-party delivery, in-person traffic, and the responsibility of protecting franchisee investments.

It’s a strategic approach shaped by a brand that grew out of COVID and understands how the trade area has evolved since the early days of Fast Casual.