The New Era Of Property Management Entrepreneurs With Chester Toohey

As the property management landscape evolves, we are witnessing a new breed of property entrepreneurs who are redefining the industry with innovative approaches, cutting-edge technology, and a fresh perspective on client service.

These trailblazers are not just managing properties; they are transforming the entire business model, creating more efficient, customer-centric, and profitable ventures.

If you’re seeking motivation, education, and a reminder of how excellent property management can be, this episode is a must-listen.

I chat with Chester Toohey, the young founder and director of Toohey Property Management, based in Brisbane. At just 21, Chester has already made a significant impact in the property management industry with his innovative solutions and exceptional service, focused on long-term rentals. Starting his journey at 18 with short-term rentals, Chester has grown his company by emphasising a client-first approach and leveraging technology. His vision, leadership, and dedication serve as a beacon of inspiration for aspiring property management entrepreneurs.

“Finding your rhythm is really important. For me, that’s waking up early and getting all the urgent tasks done, like hitting the tennis ball into someone else’s court.”

— Chester Toohey

In this episode we explore:

  • How Chester  started in short-term rentals, managing Airbnb properties with a software-based approach
  • How to take a more active role in maximising client relationships and property performance
  • Why communication is key and how setting expectations and maintaining open communication can lead to better outcomes for everyone
  • How to leverage data for success such as tracking calls and conversions so you can stay motivated and identify the most effective strategies for lead generation
  • How to assess different lead generation strategies like cold calling and social media marketing to best serve your strengths
  • How to embrace competition and how it can help you be innovative and collaborative which can lead to creating further opportunities in the industry


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