In this episode of Unfiltered, Dylan Scroggins and Matt Speer sit down with Chicago-based entrepreneur and property management leader Mark Ainley for a wide-ranging conversation on growth, marketing, and the evolving real estate landscape. Mark shares how his early experiences in investing and property management shaped the foundation of GC Realty, discusses how he's built a business that thrives in both residential and commercial markets, and explains why reputation and responsiveness remain his company's most powerful differentiators. He also offers a candid look at how technology, regulation, and industry maturity are reshaping the property management space.

We discuss:

• The evolution of GC Realty from a small brokerage to a major property management firm
• How reputation, responsiveness, and reviews drive long-term growth
• The challenges and opportunities of scaling a management company past key "growth ceilings"
• Why regulation can ultimately strengthen the property management industry
• How AI and new tools are transforming operations and marketing strategies

Links:

Mark on LinkedIn - https://www.linkedin.com/in/mark-ainley/

GC Realty and Development - https://www.gcrealtyinc.com/

Prompt Cowboy - https://www.promptcowboy.ai/

Hook Point — https://hookpoint.com/hook-point-book/

Pitch Anything — https://www.amazon.com/dp/0071752854

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:01:50) - Life as a Bears fan (00:03:10) - Mark Ainley's journey into property management (00:05:45) - Challenges and growth in property management (00:08:45) - Industry insights and future concerns (00:14:39) - Marketing and content creation (00:17:49) - Real estate investing and media ventures (00:19:32) - Emerging technologies and tools for business success (00:20:08) - The importance of reputation management (00:21:50) - Balancing real and online reputations (00:25:27) - Effective tools and apps for business (00:27:48) - AI and its role in business operations (00:29:11) - Recommended books and podcasts for PM leaders (00:33:50) - The future of property management