Fail Fast, Negotiate Hard: The Layla Kasha Playbook

In this inspiring episode, Layla Kasha, Chief Marketing Officer at Grocery Outlet, joins Ben Kaplan to discuss how immigrant grit, entrepreneurial roots, and fearless marketing have shaped her unique leadership style. Layla dives into Grocery Outlet’s “extreme value” model, selling branded products at deep discounts, and explains the brand’s bold pivot from traditional paper ads to fully digital campaigns.She shares her powerful personal story, from growing up in a Middle Eastern immigrant family and working in her father’s Michigan party store as a child, to running her own restaurant and eventually becoming a CMO. Layla breaks down her approach to ruthless (yet win-win) negotiation, how failure became her greatest teacher, and why betting on yourself matters, especially when the stakes are high.You’ll hear candid lessons about leadership, gender dynamics in the corporate world, and why she keeps Chris Voss’s Never Split the Difference in her car door. Plus, the surprising pet project she and her husband run on the side.Whether you're an aspiring marketer, a fan of founder stories, or just someone trying to stretch a dollar at the grocery store, this episode delivers plenty of value.