Gregory shares how he built his brand on the foundation of family values and entrepreneurial grit. Following his passion for coffee, he launched his first café in New York City in 2006 - with a focus on quality, innovation, and authentic customer experiences, Gregory's Coffee has grown into a beloved chain that still carries the heart and soul of a family business.

Key Takeaways:
• Schatzy and Jimmy touch on Toast Point of Sale (POS) system. A user-friendly and highly recommended POS system for restaurants, referring to it as the "Apple of point of sale.”
• Brewing up some grounds-breaking news: Gregory's Coffee is expanding nationwide with Simon Property Group.
• Gregory discusses the new partnership with Simon Property Group and the opening of 15 stores in key mall locations, including Southern California, Washington state, Texas, Florida, and Pennsylvania - "They were looking for a brand that they thought could play well across the country, not a regional player, not too niche, something that could be catering to, you know, high-end boutique, you know, type of concept."
• Jimmy recognizes a strategic and fitting collaboration, as Simon is actively working to enhance the mall experience by integrating food and beverage (F&B) options to attract customers back into physical retail spaces.
• Gregory discusses leveraging technology like Chowly and Toast to enhance their delivery services, making the process more seamless and efficient both for their team and customers. Jimmy touches on the importance of "return on time”, and asks about the role of AI and automation in Gregory's Coffee's operations. Does Gregory envision a future where robots could be brewing coffee?
• Committed to innovation, authenticity, and creating unique, high-quality products helps Gregory’s Coffee stand out in a crowded market.
• Gregory talks about "passion and grit" as Gregory's Coffee expands and his hands-on approach, ensuring that every new store opening embodies the same energy and authenticity that started the business.
• In "Talking Back," Gregory flips the script, asking Schatzy and Jimmy about their current interests and focus within the intersection of technology, investing, and hospitality. Gregory mentions Steve L's work with "kernel and flippers", asking them what is exciting them the most in this rapidly evolving industry.

Gregory, Schatzy, and Jimmy enjoy a lively session with games like "What’s Hot and Not," "The Spice is Right," and "Trivia Tuesday”.