Succession in family business isn’t just a name on a chart—it’s one of the most emotional, complex, and defining transitions a family can face. Emily Holdman, Managing Director at Permanent Equity, joins Jamie to unpack why succession so often gets framed as a power struggle, and how families can turn it into a collaborative, purpose-driven process instead.   They explore what emotional readiness looks like for both generations, the misconceptions that derail succession planning, and the overlooked leadership skills that truly prepare the next generation. It’s a candid conversation about letting go, stepping up, and building continuity that lasts beyond titles.

Fourth-generation leader Nick Perrino shares how Home Run Inn grew from a neighborhood tavern to a Chicago tavern-style pizza legend—without losing the family feel. From scaling to 80 pizzas a minute to navigating succession after loss, Nick reflects on the values, intentional growth, and employee culture that have kept people at the table for decades.

Matt Miniat of South Chicago Packing and Miniat Holdings joins Jamie to talk about what it means to steward a fifth-generation family business rooted in one of Chicago’s most iconic industries: meatpacking. From early pivots to product reinvention, Matt shares how the company leaned into its tallow legacy and used the unexpected power of TikTok and direct-to-consumer growth to find new relevance. They explore the tension between tradition and innovation, the weight of operating under your own name, and how values like long-term thinking and food safety shape every decision. It’s a conversation about staying grounded in where you come from—even as you adapt to a rapidly changing world.

In this episode, Jamie sits down with Elana Schulman, third-generation leader of Eli’s Cheesecake, to explore what it means to carry a family name—and a legacy—into the future. From the steakhouse where it all began to the values that still guide the business today, Elana shares stories of innovation, identity, and what it's like to grow up inside one of Chicago’s most beloved food brands.  From launching a non-dairy cheesecake to reimagining what leadership looks like in the third generation, Elana Schulman brings humor, heart, and insight to this episode.

Work Was Love Featuring: Jessica Shah and Michelle RanavatJoin Jamie and her sisters for an intimate kickoff conversation. They discuss their unique paths into (and around) their family business, the dynamics of sibling collaboration, and what it means to grow up inside a company—literally.