About the Episode How do you successfully transition a business across five generations without creating resentment or burning out the next generation? This episode tackles the complex realities of family business succession planning through the story of Tiger's General Store in Hayesville, North Carolina — a business that has operated continuously since 1875. In this three-generation conversation, host Matt Wagner sits down with Rob Tiger (fourth generation), Holly Tiger (married into the business), and Lauren Tiger (fifth generation) to explore the intentional decisions that have kept this 150-year-old business thriving. From Rob's initial reluctance ("I'll give you a year") to Lauren's carefully structured path that required building her own career first, this family reveals the honest conversations and strategic choices behind successful succession. Discover practical strategies for: Creating choice, not obligation: Why forcing Lauren to attend college far from home and build her own career was critical to preventing resentment Managing the transition timeline: How Lauren balances full-time physical therapy work with increasing store responsibilities while maintaining benefits Adapting without losing authenticity: Staying relevant for 150 years by asking teenagers what's trending while maintaining the store's character Building community connections: Why giving back and being visible in local nonprofits is non-negotiable for small town businesses The reality of work-life balance: Honest talk about 10–12-hour days, late nights, and the delegation challenges that come with family businesses Keeping customers engaged across generations: How one family has shopped there annually for 11 years, each visit a cherished tradition Whether you're planning a business transition, considering buying a family business, or wondering how to stay relevant in a small market for decades, this episode provides a candid look at what actually works — and what doesn't — in multi-generational business ownership. Join us as we hear directly from three generations about losing money in the early years, evolving from groceries to gifts, resisting pressure to go fully online, and why consistency matters more than perfection in small business success. Special thanks to Sherry Adams, North Carolina Main Street Program, for coordinating this episode. Connect: Learn about Tiger's General Store in Hayesville, NC Learn about Historic Hayesville, Inc. Learn about NC Main Street & Rural Planning Center  Episode Links: Watch video interview Listen on Apple Podcasts Listen on Spotify Subscribe for updates