Beyond the Business: Finding Your Role in the Family Legacy with Jeff Wilcoxon

Beyond the Business: Finding Your Role in the Family Legacy with Jeff Wilcoxon

In this episode, Jamie Shah talks with Jeff Wilcoxon — a next-generation family business leader and thoughtful advocate for redefining what “being involved” really means. Together, they explore the quiet but critical roles that family members play beyond the corner office: from shaping vision and governance to fostering trust and continuity. Jeff shares lessons from his own journey, the importance of curiosity and connection, and why contribution doesn’t always require a job title. This episode reminds us that family business leadership isn’t limited to those running the company — it’s also carried by those who help sustain its values, relationships, and purpose across generations.

Succession Isn’t a Spreadsheet

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.

A Seat at the Table Featuring: Nick Perrino, Home Run Inn

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.

"With Our Name on the Door" - featuring Matt Miniat

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.

Big Slice Energy: Elana Schulman on Legacy and Leadership at Eli’s Cheesecake

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.