Evernest Property Management Show

In this episode, Matthew Whitaker and Gray Hall sit down with Evernest's VP of Property Management, Reese Hamilton, to break down how Evernest built a weekly churn meeting, why offboarding forms only tell part of the story, and the specific communication habits that keep owners from leaving.

You'll learn:

• Why a vacant property makes an owner eight times more likely to churn, and the communication cadence that keeps them calm during that window
• The three layers of great owner communication, speed, thoroughness, and anticipating the next question before it's asked, as Reese Hamilton explains
• How Evernest separates regrettable churn from non-regrettable churn, and sets a monthly churn goal of about 1.5%

Guest: Evernest's VP of Property Management, Reese Hamilton

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode, Matthew Whitaker and Gray Hall break down how Evernest runs its maintenance and repairs operation, drawing on real numbers, including 35 in-house technicians, a $3,500 average turn cost, and a 78% billable utilization rate, to help owners decide whether in-house maintenance or third-party vendors make more sense for their business.

You'll learn:

• Why bringing maintenance in-house only makes sense once a market hits roughly 300 homes, and how density decides which trades to add next
• How Evernest prices in-house maintenance work to actually turn a profit, splitting the hourly rate into pay, overhead, and margin
• The real tradeoffs between in-house technicians and third-party vendors, from schedule control and liability to seasonal work swings and turnover

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode, Matthew Whitaker and Gray Hall break down what buyers actually look for when acquiring a property management company, drawing on lessons learned from 33 acquisitions to cover valuations, diligence red flags, and how to think about your team and brand when you're ready to sell.

You'll learn:

• Why property management valuations are shifting toward price-per-door and a revenue multiple somewhere between one and one and a quarter times, with maintenance and management revenue valued very differently
• The three things buyers diligence most closely before a deal, churn history, client concentration (units per owner), and contract terms, and why each one can make or break your price
• How to think about your employees and brand equity when selling, and why most PM brands have less market recognition than owners assume

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode, Matthew Whitaker and Gray Hall break down the different types of outside influence that can help property management business owners make better decisions, stay accountable, and grow their companies.

You'll learn:

• Why every property management business owner should consider joining a mastermind
• When a growing company may need a board of advisors instead of relying only on industry peers
• How a board of directors creates a higher level of accountability when outside capital is involved

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode, Matthew Whitaker is joined by Brett Drevlow, Director of Leasing at Evernest, Bryan Shaw, Pricing Manager at Evernest, and Juan Burgos, CEO of Haven, to break down the biggest rental leasing trends property managers need to know right now.

You'll learn:

• Why the first 7 to 10 days of a rental listing are critical for understanding demand
• How AI and faster follow-up can help property managers capture more leads after hours
• Why pricing correctly upfront can reduce vacancy and help homes lease faster
• How concessions, fee waivers, and market-specific pricing strategies are impacting rental performance

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Connect with Matt and Gray at Evernest: Evernest.co

Guest: Brett Drevlow, Director of Leasing at Evernest

Guest: Bryan Shaw, Pricing Manager at Evernest

Guest: Juan Burgos, CEO of Haven

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode, Dylan Scroggins of Kalmar Group sits down with Matthew Whitaker, founder and CEO of Evernest, to talk about building a property management company, acquisitions, AI, and the future of the industry.

You'll learn:

• Why going deep in one market can be more profitable than expanding too quickly
• What Evernest looks for when buying property management companies
• How AI is already helping property managers improve leasing, maintenance, hiring, and operations

Learn more about Kalmar Group here: https://www.thekalmargroup.com/pm

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Connect with Matt and Gray at Evernest: Evernest.co

Guest: Dylan Scroggins of Kalmar Group

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode, Matthew Whitaker and Gray Hall discuss the three meetings every property management company needs to improve communication, create accountability, and keep teams aligned as they grow.

You'll learn:

• Why daily huddles are the foundation of a high-performing team
• How Level 10 meetings help solve problems and keep priorities on track
• The role one-on-ones play in developing people and maintaining alignment

Join the Crane waitlist to learn more from a community-driven network of property management professionals: joincrane.co

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.

In this episode of the Evernest Property Management Show, Matthew Whitaker breaks down the 3 biggest misconceptions about managing people that hold leaders back as they grow their teams and businesses.

You'll learn:

• Why being a micromanager isn't always a bad thing (and why the former head of Disney agrees)
• How to handle the reality of getting pulled back into the business after delegation
• The ways that delayed feedback damages your organization

Join the Crane waitlist to learn more from a community-driven network of property management professionals: joincrane.co

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 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'll get them ahead)
• How a 30-day PM could rival a 30-year PM's skill set by leveraging AI
• Where boutique property management companies have a competitive advantage (and how to adapt their strategy to your business)

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 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 why that's often a sign of growth, not failure).
• A practical framework for "running your own race" so you stop comparing your messy middle to everyone else's social media highlight reel and start playing the long game in your market.
• How to deliberately build a core team that stays for 5–10+ years, compounds trust, and gives you the "operating leverage" no tech stack can replace.

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Connect with Matt and Gray at Evernest: Evernest.co

Link: Connect with Evernest

Link: Evernest YouTube Channel (@EvernestPropertyManagementShow (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: [email protected]

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Production House: Flint Stone Media

Copyright of Evernest 2026.