What does it really look like to leave corporate life and step into a family-owned business? In this episode of Entrepreneurial Shades of Gray, hosts Dani Dials and Chelsey Sayasane sit down with Faye Olensky of Olensky Brothers, a multi-generation, family-owned business rooted in Mobile and right on the heart of the Mardi Gras parade route. Faye shares what it was like to spend years building a corporate career before making the leap to help lead her family’s legacy business full-time. She’s joined by her daughter Courtney, who offers perspective on what it means to choose a path in a family business, especially when the next generation may have different dreams and aspirations. Together, they talk about legacy, leadership, and the decisions that come with continuing a family-built brand.

From the realities of entrepreneurship inside an established business to the behind-the-scenes intensity of Mardi Gras season, this conversation offers insight for anyone navigating big career transitions, family dynamics in business, or the question of when it’s time to take the leap.