EPISODE · Aug 8, 2025 · 39 MIN
#203 Fearless Leadership: Jemila Winsey on Building Multi-Billion Dollar Brokerages
from HalloCasa Real Estate Show · host HalloCasa
This episode is brought to you by HalloCasa, the SEO-ranked digital business card for real estate agents. Looking to find the right agent, no matter where you are?Visit https://home.hallocasa.com to discover and connect with top real estate agents globally.In this inspiring episode of HalloCasa, Jemila Winsey — VP of U.S. Brokerage Operations at Real (NASDAQ: REAX) — shares her journey from hitting rock-bottom to leading a team of over 15,000 real estate agents.We dive deep into leadership, operational excellence, and the courage it takes to build and scale successful brokerages. Jemila also opens up about the challenges and triumphs of being an alpha woman in leadership, and why fearlessness, love, and courage are the keys to lasting success.Timestamps:00:01:40 Introduction00:03:51 Hitting Rock-Bottom00:06:20 Jumping into Real Estate00:09:55 Running and Jump-Starting Your Own Real Estate Brokerage00:13:30 About REAL00:15:40 Implementing Operational Excellence Across 15,000 Real Estate Agents00:18:00 Leadership: Building and Leading a Team00:24:32 Leadership as an Alpha Woman00:29:00 Fear, Confidence, Courage, Love, and Being Fearless00:34:00 Advice for Young Entrepreneurs on Courage and Growth00:38:00 Running Your Own Brokerage Successfully Over the YearsConnect with Jemila: / jemilawinsey / jemilawinsey https://connectwithjemila.com/
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#203 Fearless Leadership: Jemila Winsey on Building Multi-Billion Dollar Brokerages
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