Doing Things Differently: How Cailey Heaps Built a Real Estate Empire

In this week’s episode of Your Cup of Joy, I’m joined by Cailey Heaps—Founder and CEO of the Heaps Estrin Team and The Lobby, RBC Women of Influence finalist, Canadian Women Entrepreneur of the Year, and YPL member. A powerhouse in the real estate industry, Cailey has built one of the most successful teams in the country by doing things differently.She shares what sets the Heaps Estrin Team apart, the unconventional path that led her to real estate, and how strategic marketing plays a major role in their success. We also explore The Lobby—a unique extension of their brand that blends art, events, and community in a way that redefines real estate beyond just buying and selling homes.As a fellow twin mom, Cailey opens up about the challenges of balancing business and motherhood, the importance of extreme honesty in relationships, and the biggest lessons she’s learned along the way. She reflects on how her hardest moments have led to the greatest growth and why self-care—beyond just fitness and nutrition—has become a top priority.We also dive into her passion for philanthropy, the values that guide her leadership, and her advice for women stepping into leadership roles. From embracing change to navigating hard conversations, Cailey’s insights are both inspiring and deeply practical.This episode is packed with wisdom, resilience, and a fresh perspective on success—both in business and in life. You won’t want to miss it!Cailey’s linksInstagram- https://www.instagram.com/caileyheapsHeaps Estrin Team- https://www.instagram.com/heapsestrinLinkedIn - https://www.linkedin.com/in/cailey-heaps-b838b33Ariana's Links:Website Instagram: @‌ArianaJoyChristie @YourCupofJoyPodcastTikTok: @‌ArianaChristie

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