Matthew Whitaker is back! And a lot’s changed since his first appearance.

We discuss:

(00:01:38) - Introducing season six
(00:02:44) - Matt’s background and career
(00:07:04) - Dealing with owners
(00:20:47) - Sponsor - RentEngine
(00:22:41) - Evernest’s tech stack
(00:28:03) - Transitioning away from eos
(00:33:35) - Dealing with management layer issues
(00:40:31) - Sponsor - Crane
(00:42:35) - Categories of owners
(00:44:05) - Multifamily experiences
(00:52:38) - The state of Evernest’s acquisition appetite
(01:02:38) - Leadflow realities
(01:06:57) - The state of the industry
(01:09:41) - Get in touch with Matthew

Learn more & connect with me here:

⁠Crane⁠, the private community for property management business owners.
⁠My Free PM Newsletter⁠
⁠RL Property Management⁠

Learn more and connect with Matthew here:

Evernest
Matthew on LinkedIn
The Evernest Property Management Show Podcast on Apple

Today, Evernest manages nearly 20,000 doors across 50+ markets. We dig into how they’re structured, what they’ve learned from buying 17 PM companies in six months (!), and why the “property manager” job title is making a comeback.

Matthew breaks down their tech stack, AI experiments, and how they think about scaling operations without sacrificing owner experience. We also talk about churn (especially from mid-sized investors), how valuation multiples have shifted, and what he wishes more property managers understood about communication vs. execution.

If you’re rethinking org charts, prepping to sell, or just trying to reduce chaos, this one’s worth your time.

Day 9: Genesis 19:1–20:18; Matthew 7:24–8:22; Psalm 7:1–9

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