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PODCAST

Evernest Property Management Show

Matthew Whitaker and Spencer Sutton

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.

business entrepreneurship

All Episodes

43:03

Episode 194: Offboarding Forms, Phone Calls, and NPS:...

Evernest Property Management Show ·

2026/10/05

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,

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48:39

Episode 193: The PM Maintenance Playbook: In-House...

Evernest Property Management Show ·

2026/09/21

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

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53:42

Episode 192: Selling Your Property Management...

Evernest Property Management Show ·

2026/08/10

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

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32:12

Episode 191: The 3 Levels of Accountability Every PM...

Evernest Property Management Show ·

2026/07/27

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

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56:58

Episode 190: Rental Leasing Trends Property Managers...

Evernest Property Management Show ·

2026/07/13

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

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38:44

Episode 189: The Next Era of Property Management: AI,...

Evernest Property Management Show ·

2026/06/29

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

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48:30

Episode 187: The 3 Meetings Every Property Management...

Evernest Property Management Show ·

2026/06/08

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

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26:43

Episode 186: The 3 Biggest Misconceptions About...

Evernest Property Management Show ·

2026/05/25

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

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42:55

Episode 185: The Future of Property Management: Scale...

Evernest Property Management Show ·

2026/05/11

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

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43:51

Episode 184: Building Evernest: The 3 Principles...

Evernest Property Management Show ·

2026/04/27

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

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56:17

Episode 183: How AI Is Changing Property Management:...

Evernest Property Management Show ·

2026/04/13

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

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57:40

Episode 182: The AI Tools Property Managers Are Using...

Evernest Property Management Show ·

2026/03/30

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

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41:52

Episode 181: The 550-Door PM Business that Sold for...

Evernest Property Management Show ·

2026/03/16

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

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01:01:20

Episode 180: The WHO Hiring Process: Find A-Players,...

Evernest Property Management Show ·

2026/03/02

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

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01:07:38

Episode 179: EOS & Traction - Making Order Out of the...

Evernest Property Management Show ·

2026/02/16

In this episode of The Evernest Property Management Show, Matthew and Gray reveal the massive secret behind Evernest's success: following Traction by Gino Wickman. They explain how focusing on this program empowers businesses of all industries to streamline decision-making, reduce operational friction, and achieve incredible results. You'll learn: Why everything starts with a solid vision (and why it shouldn't be something that just lives on your office wall) How to break your goals into achievable

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01:26:24

Episode 178: How to Sell (or Buy) a Property...

Evernest Property Management Show ·

2026/02/02

Matthew and Gray divulge Evernest's complete process for buying (and selling) a property management company. Whether you're a property manager thinking about your exit or an operator looking to scale faster through acquisitions, this episode walks through the real-world playbook: from finding deals and valuing a PM business, to due diligence, LOIs, financing, closing, and post-close integration. You'll learn: The 9 steps to sell your property management business the right way Marketing tricks that

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01:00:51

Episode 177: Meet the New Co-Host: The Ops Leader...

Evernest Property Management Show ·

2026/01/19

In this episode of The Evernest Property Management Show, Matthew introduces his new co-host, Gray Hall. Gray is Evernest's Vice President of Operations, and he has been with the company for almost 10 years. Now, he's sharing his property management insights. You'll learn: Why selling the vision for your property management company is a risk - but it pays off in terms of staff quality and business outcomes How repeated exposure to Evernest's interview process influenced Gray's success The story

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34:15

Episode 176: My Time at Evernest Has Come to an End…...

Evernest Property Management Show ·

2026/01/12

In this milestone episode, Spencer Sutton announces his decision to step away from Evernest after 11 years to return to neverthirst, the nonprofit he founded, despite loving his role and being at the top of his game. Spencer and Matthew reflect on faith, fear, discipline, and why knowing when to leave can be just as important as knowing how to build. You'll Learn: Why staying comfortable might be the most dangerous career move you can make How to know when it's time to leave—even when everything is

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25:20

Episode 175: How Top Property Managers Retain...

Evernest Property Management Show ·

2025/12/22

Ensuring your team feels appreciated is critical to long-term success in property management. In this episode, Spencer shares strategies and insight into building a team that lasts the test of time. You'll learn: Why the vision of the business feeds into trust and autonomy How to attract (and keep) A players The importance of creating a scorecard to guide employee behavior and goals =================================== Connect with Matt, Spencer, and Gray at Evernest: Evernest.co Link: Connect with

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38:42

Episode 174: Your Legal Wake-Up Call: Lawsuits You...

Evernest Property Management Show ·

2025/12/15

Successful property management relies on a robust understanding of the legal landscape, so Spencer and Matthew invited Monica K. Gilroy of the Gilroy Firm onto The Property Management Show. As a subject matter expert in real estate litigation, Monica shares insights into Fair Housing law and common legal pitfalls that could tank your business. You'll learn: How to validate emotional support animals (without getting duped) Updates to reasonable accommodation laws and what all property managers need

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193 results

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