Derby week in Kentucky comes with a lot of traditions. For Rebecca Rupp and her family, one of those isn’t just something she celebrates, it’s something her family built.

Her great grandparents created Derby Pie in 1954. Her dad spent decades growing it into what it is today. And in 2024, after his passing, Rebecca and her siblings were faced with a decision they never expected to make.

Step in…or let it go.

In this conversation, Rebecca shares what it looked like to walk into a business she didn’t plan to run, in the middle of grief, without a roadmap. We talk about the weight of legacy, learning a business from the inside out, and figuring out how to lead in your own way while still protecting what came before you.

This isn’t really about pie. It’s about family, identity, and what happens when something that’s always been part of your life suddenly becomes your responsibility.

About Rebecca Rupp

Rebecca Rupp is co-owner of Kern’s Kitchen, the family business behind the original Derby Pie.

After growing up around the business, she stepped into ownership in 2025 alongside her brother following the unexpected passing of their father, who had led the company for decades.

Today, Rebecca focuses on relationships, brand presence, and continuing the legacy of a product that’s become a Kentucky tradition, while finding her own way to lead it forward.

Learn more at:

https://derbypie.com/

About Kristina Lowe

Kristina Lowe is the founder and strategic partner of Tripoint Strategic Group, a Louisville-based firm that works with businesses and organizations to clarify direction, align strategy, and drive growth.

With over 20 years of experience across marketing, product, and strategic development, Kristina has led growth initiatives for global brands and now partners with small to mid-sized companies and nonprofits to help them move from ideas to execution.

She is also the host of Tripoint Conversations, a podcast focused on real stories from leaders, founders, and operators, exploring the decisions, challenges, and moments that shape how people build and lead.

To learn more or be a guest, go to:

https://www.tripointstrategicgroup.com/podcast