Evernest Property Management Show

Episode 185: The Future of Property Management: Scale Up or Stay Boutique

May 11, 2026

In this episode, Matthew Whitaker and Gray Hall discuss where property management is headed, how AI is reshaping the industry, and why companies may need to choose between building scale or staying boutique rather than getting caught in the middle.  They also explain how joining a community-driven network like Crane can take your property management business to new heights. Join the waitlist today: www.joincrane.co You'll learn: Why big PM players may be compressing their pricing (and how it...

Episode 184: Building Evernest: The 3 Principles Behind Award-Winning Property Management

April 27, 2026

This reflective episode pulls back the curtain on what it's really taken to build Evernest from startup grind to award-winning national operator - spouses' sacrifice, near-missed payrolls, and all. It's an honest "anti-highlight reel" for property management leaders who feel like everyone else is winning while they're still slogging through the mud. You'll learn: What it actually feels like behind the scenes when you're raising capital while wondering if you'll make payroll on Friday (and wh...

Episode 183: How AI Is Changing Property Management: Strategy, Risks & What's Next (Part 2)

April 13, 2026

AI is moving faster than any tech we've seen; if you aren't building a strategy, you're already behind. That's why Matthew Whitaker and Gray Hall invited experts Ray Hespen (CEO of Property Meld), Lindsay Liu (CEO of Super), and Nitan Gupta (CEO of Mason) to share high-level shifts and hidden risks of AI, helping you decide which tools are worth the investment and which are just noise. You'll learn: The "30% Rule" for scaling and how to automate nearly a third of your daily tasks, like invoi...