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 ca ...