Building a Lasting Brand w/ ”Nanny Connie” & Courtney Simpson

In this episode of Entrepreneurial Shades of Gray, we sit down with “Nanny Connie” Simpson and her daughter, Courtney, for a conversation about building a brand that lasts, and the family behind it.

Known as a “nanny to the stars,” Connie has worked with some of the most high-profile families in the country, building a nationally recognized name in childcare within elite and high-demand environments. She shares stories and insights from a world few people ever see, along with what it actually takes to earn trust at that level. From vetting clients to setting up systems that help families function and thrive, Connie also opens up about the business side of her work… and how she’s turned a deeply personal calling into a structured, in-demand brand.

Courtney shares what it was like growing up with a mom in high demand, how that shaped her own journey into nanny work, and where their approaches align, and differ. It’s insightful, honest, and at times hilarious! A conversation about entrepreneurship, legacy, and building something that lasts.

Entrepreneurial Shades of Gray, hosted by FOX10’s Chelsey Sayasane and Dani Dials, is where real conversations meet real stories of resilience, innovation, and growth. Each week, we uncover the journeys of entrepreneurs and business leaders navigating the gray areas of success. From local start-ups to larger powerhouses, our conversations aim to uncover the unfiltered realities behind building and leading a business. Whether you’re an aspiring entrepreneur or a seasoned leader, you’ll find inspiration, challenge, and connection in every episode.