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.

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 invoice processing and maintenance scheduling, to free up your team for growth.
• The truth about AI fraud and why smarter tools also mean smarter scammers (plus specific ID verification steps you need to take to protect your owners).
• Why curiosity and judgment are becoming your biggest competitive advantages as AI tools become a basic commodity.
• How to use internet-connected hardware and AI to create a predictive maintenance program.

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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.

There are hundreds of AI tools out there - but what are actual, successful property managers using in 2026? Matthew and Gray invited top property managers to discuss their AI strategies, how to turn pain points into automated processes, and so much more.

You'll learn:

• How Evernest is using Haven AI to solve real-world problems, including fixing a lock box for a resident
• The secret to creating user-generated content through custom AI bots 24/7
• Super-powered hacks for Claude and other popular AI tools that you need to start using today

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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.

Building a property management company that lasts takes more than hustle; it takes strategy, systems, and a willingness to evolve. In this episode, longtime investor and entrepreneur Mitch Deminski joins Matthew Whitaker and Gray Hall to share how he built a 550+ door property management business, navigated the 2008 housing crash, and ultimately sold his company after decades of steady growth.

Mitch's journey is anything but typical. From selling inmate pay phone systems in the telecom industry to becoming a major player in the Columbus real estate market, he explains how a slow-and-steady approach to investing, strong relationships with investors, and operational discipline helped him turn property management into a valuable, sellable asset.

You'll learn:

• Why starting scrappy with room to grow strengthens your real estate investing strategy
• How to leverage Mitch's "tortoise strategy" (steady accumulation beat chasing flips)
• The one marketing trick that saved Mitch thousands

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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 the WHO Hiring Process and how it helps companies consistently find A-players while avoiding costly hiring mistakes. They break down the step-by-step framework from scorecards and screening interviews to reference checks, replacing gut decisions with a proven system.

You'll learn:

• How to structure your hiring process to source the best candidate
• The questions you need to be able to answer about each role to maximize success
• Why you should ask how the candidate's last 5 bosses would rate them - and how to get the truth

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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.