Evernest Property Management Show

Hosted by Matthew Whitaker and Spencer Sutton

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Episodes

191

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Aug 2026

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About the show

If you're a property manager looking to scale your business beyond 300, 500, or even 1,000 doors, you've come to the right place. You might be asking - Is it worth it? How do I do it? Where do I find the money? What about the people? Trust us, we've made every mistake you can think of...then we made some up. Listen in as we describe what worked and what didn't on our journey from 300 to 3,000 houses.

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August 10, 2026Episode 19253 min

Episode 192: Selling Your Property Management Company? Here's What Buyers Actually Look For

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

July 27, 2026Episode 19132 min

Episode 191: Masterminds, Advisors & Boards: What Property Management Owners Need

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

July 13, 2026Episode 19056 min

Episode 190: Rental Leasing Trends Property Managers Need to Know

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

June 29, 2026Episode 18938 min

Episode 189: The Next Era of Property Management: AI, Acquisitions & Scale

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

June 8, 2026Episode 18748 min

Episode 187: Huddle, Level 10, Same Page: The Only 3 Meetings Every PM Company Needs

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

May 25, 2026Episode 18626 min

Episode 186: Why Micromanaging Is A Good Thing: The 3 Misconceptions About Managing People

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

May 11, 2026Episode 18542 min

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

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) =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

April 27, 2026Episode 18443 min

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

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. =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

April 13, 2026Episode 18356 min

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

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. =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.

March 30, 2026Episode 18257 min

Episode 182: The AI Tools Property Managers Are Using in 2026 (Part 1)

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 =================================== 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: podcast@evernest.co =================================== Production House: Flint Stone Media Copyright of Evernest 2026.