Evernest Property Management Show

In this episode, Matthew Whitaker and Gray Hall play out a hypothetical: if they started a property management company from scratch today, with everything they know now, what would they actually do differently, covering market choice, financing, and the first hires they'd make. You'll learn: Why they'd both build toward 3,000 doors instead of staying a 300-door boutique, and the market they'd pick...

In this episode, Matthew Whitaker and Gray Hall break down what to do when your property management company is off track on its annual goals heading into Q4, using Evernest's own EOS goal-setting framework, from a 250,000-door 10-year target down to the five goals they track every year, as the example. You'll learn: Why Evernest almost never hits its one-year goals but lands within 5% of its three...

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...

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 o...

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 multipl...

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...

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 propert...

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...

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...

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 wa...

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...

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...

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 lear...

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...

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.  Mi...

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 candid...

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...

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....

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...

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...

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 ==============...

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 anim...

2026 is on the horizon - are you ready to accomplish your goals? Spencer discusses how to set yourself up for a productive year and build fulfilling targets in this episode of The Evernest Property Management Show. You'll learn: Why you're the hardest person to negotiate with How not feeling worthy of accomplishing your goals is slowing down your success The importance of vision when setting your...

Want more owners, better leads, and shorter sales cycles? In this episode, Spencer sits down with Jen Ruelens to unpack the five major reasons you need to start creating video content now—or risk getting left behind. Reach out to Jen and learn more via https://holditwithpmjen.com You'll learn: How to leverage the know–like–trust framework to boost your business The most efficient method to leverag...

In this episode, Spencer Sutton sits down with Mark Ainley, co-founder of  GC Realty & Development  and host of the  Straight Up Chicago Investor Podcast , to discuss how video, content, and authenticity build invaluable trust in today's market.  You'll learn: How to build a local brand through storytelling Which data and metrics matter for growth (and what doesn't) Why your personality is the mos...