In Episode 20 of Between 2 Hats, hosts Patrick Osman and Phillip Burton sit down with Taylor Brakefield, CEO & Owner of PROS PM, for one of the most raw and inspiring conversations yet.

Taylor shares her journey in the property management industry — from early career lessons to navigating leadership in a male-dominated space, and ultimately making the decision to bet on herself and start her own company. After a defining moment made it clear there was no future for her where she was, Taylor walked away and launched PROS PM with just 11 doors. Today, she manages nearly 800.

This episode dives deep into what it really takes to build a business from the ground up: resilience, community, mindset, and the emotional weight that comes with leadership. Taylor opens up about hiring the right team, building a healthy workplace culture, balancing family and business, and handling the difficult situations no one prepares you for in property management.

If you’re an entrepreneur, property manager, or leader navigating growth, setbacks, or self-doubt, this episode is a powerful reminder that grit, clarity, and conviction can change everything.

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