Jeremy Sasson joins Jake Wurzak to unpack his obsessive, guest-first approach to hospitality and share how he’s built a thriving portfolio of restaurants without external investors or debt. The conversation traces Jeremy’s evolution from a post-college startup grind to crafting some of Detroit’s most beloved dining experiences. He explains how design, service, and team alignment all flow from a single emotional driver: how a guest feels at every touchpoint. Jeremy also reveals how he builds restaurants through the lens of fashion, explains the overlooked costs of doing hospitality well, and offers rare insight into the operational decisions that separate great concepts from lasting brands. We discuss: Why every element of a restaurant must begin with how it makes guests feel The core reasons he turned down the family real estate business to pursue hospitality What he learned building his first restaurant with no industry experience Why he avoids celebrity chefs and prioritizes team members who “pick him” The importance of eliminating weak cultural fits—even when it hurts in the short term This episode is a masterclass for anyone building hospitality experiences with purpose and longevity in mind. Links: Heirloom Hospitality - https://heirloomhospitality.com/ Jeremy on LinkedIn - https://www.linkedin.com/in/jeremy-sasson-a172b3195/ Connect & Invest with Jake: Follow Jake on X: https://x.com/JWurzak 1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo Topics: (00:00:00) - Intro (00:01:10) - Jeremy's college days and early ventures (00:03:38) - First steps in hospitality (00:06:40) - Lessons from family and early career (00:13:27) - The birth of a restaurant vision (00:16:26) - Starting the first restaurant: Challenges and triumphs (00:23:55) - Evolving the restaurant business (00:28:34) - Vision and execution: Creating unique dining experiences (00:46:13) - Designing the restaurant experience (00:48:03) - Service excellence and staff roles (00:50:09) - Consistency across multiple locations (00:53:06) - Core values and staff training (00:55:34) - Challenges and adaptations in the restaurant industry (00:57:11) - Design insights and restaurant layout (01:04:18) - Creating the perfect vibe (01:09:33) - Lessons from restaurant pivots (01:20:46) - Expansion strategies and new markets (01:29:51) - Favorite hotels and final thoughts