Evernest Property Management Show

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...

How do you become the leading property manager in your market? Spencer Sutton explains how to leverage videos as the ultimate differentiator in property management. You'll learn: The five reasons why you need to be creating video content (and how to get started) How to generate trust via human anchors Marketing secrets to repurpose the content you create and use it to be found by large language mo...

Former Evernester and founder of Veritas Copy, Lucas Wollschlager, shares strategies most property managers don't know that will unlock more clients and empower you to net better deals - all through your social media presence. Want help from Lucas? Reach out to him on LinkedIn. You'll learn: How to build a content strategy that evolves with your business Whether you have to be an influencer to sco...

In the second episode of our marketing series, Spencer Sutton reflects on how to encourage leads to move down your marketing funnel so you can net more clients. You'll learn: The best lead magnets in property management How to leverage email sequencing to convert more leads Why the fortune is in your follow up The difference between a marketing-qualified lead and a sales-qualified lead ===========...

How do you establish an online presence that wins clients? Kayleen vonSchondorf, Director of Marketing at Everrnest, sat down with Spencer Sutton to reveal marketing strategies that property managers need to land more leads, strengthen their brand, and convert clients. You'll learn: What kind of information your website should include to boost your number of qualified leads The importance of build...

AI is everywhere - including in property management. But will it  replace property managers? Jay Berube, Founder of  BetterWho , explains how he leverages AI for property management success in his 3,000+ door business. Reach out to Jay by visiting  BetterWho.com  or emailing jay@betterwho.com . You'll learn: Which tools boost efficiency and maximize your profit potential If AI will replace propert...

Are you using your business to meet your emotional needs? Successful investor Mark Brower is here to tell you how that approach will sabotage your growth and what to do instead. You'll learn: How to determine if your self-worth is tied too closely to your professional success (and how that desperation could ruin your progress) Why it's better to tackle one painful situation head-on instead of livi...

What does it take to become a leader who makes an impact? Where do most newbies stumble, and how can you recover? In this episode, Spencer Sutton shares his insights as Evernest's VP of Marketing through the lens of the book, Leader Shift . You'll learn: What makes a true leader (and why falling short will cost you in the long run) How humility fuels growth The three price points of leadership Why...