Ep 90 The Future of Property Management: AI, Scale & 250,000 Doors with Matthew Whitaker

Ep 90 The Future of Property Management: AI, Scale & 250,000 Doors with Matthew Whitaker

June 9, 2026 · 48 min

About this episode

Tiffany Rosenbaum interviews Matthew Whitaker about the future of property management and the impact of technology and AI on the industry.

In this episode of The Road Less Traveled , Tiffany Rosenbaum sits down with Evernest founder Matthew Whitaker to discuss his journey from real estate investor during the 2008 recession to building one of the largest property management companies in the United States. With over 15,000 units under management and a vision for 250,000 doors, Matthew shares how technology, AI, acquisitions, and operational excellence are reshaping the property management industry. Key topics include: Scaling a property management company across multiple markets How AI and automation are transforming operations The future of property management fees Acquisition strategies and calculating returns on purchased portfolios Reducing churn and improving customer experience Building proprietary software versus using third-party platforms Why great people remain the most important asset in any business Matthew's vision for the next generation of property management Whether you're a property manager, real estate investor, or business owner looking to scale, this episode is packed with insights on leveraging technology while keeping people at the center of growth. Connect with Matthew Whitaker: Find Matthew on…

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