How does a brand stay relevant for generations? In this special episode of Soul & Science recorded live at White Castle headquarters, Jason Harris is joined by Jamie Richardson, CMO at White Castle, Sarah Sylvester, CMO at Lands' End, and Kristin Tormey, Head of Media at Tripadvisor, for a conversation about brands that have stood the test of time and how they’re evolving to meet the modern moment. The panelists share how legacy brands balance heritage with innovation, the challenge of bringing in younger generations without alienating loyal customers, and why authenticity matters now more than ever. They also discuss the tension between performance marketing and brand building, the growing influence of AI and emerging technologies, and what marketers can learn from brands that have successfully navigated decades of cultural and consumer change. ⏱️ Chapters 00:00 – Intro 04:15 – How Lands’ End Started With a Mistake 06:15 – Tripadvisor and Viator: Two Brands, One Team 11:00 – White Castle’s Three R’s: Real, Relevant, & Resonant 14:05 – Why Lands’ End Still Does Catalogs 17:30 – Bringing Viator into Tiktok 21:10 – Building Trust With Gen Z 27:30 – What Makes a Brand “Born Again”? 29:25 – Incorporating Agentic Commerce & AI 35:50 – Performance Media Alone Is Not Enough 39:20 – People Are Craving Experiences 42:00 – Stepping Out of Your Comfort Zone 44:35 – Lightning Round & Personal Mantras 45:50 – Audience Questions 51:10 – The Cracker Barrel Debacle 56:00 – Marketing Myopia vs. Taking Risks 58:15 – Outro Brought to you by Mekanism.