Podcast
Evernest Property Management Show
Hosted by Matthew Whitaker and Spencer Sutton · EN
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.
27episodes
Episodes
Newest firstAll episodes
Episode 185: The Future of Property Management: Scale Up or Stay Boutique
2w ago00:42:55Tap to summarizeIn 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 (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 184: Building Evernest: The 3 Principles Behind Award-Winning Property Management
4w ago00:43:51Tap to summarizeThis 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 (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 183: How AI Is Changing Property Management: Strategy, Risks & What's Next (Part 2)
Apr 1300:56:17Tap to summarizeAI 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 (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 182: The AI Tools Property Managers Are Using in 2026 (Part 1)
Mar 3000:57:40Tap to summarizeThere 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 (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 181: The 550-Door PM Business that Sold for Millions | Mitch Deminski
Mar 1600:41:52Tap to summarizeBuilding 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 =================================== Connect with Matt and Gray at Evernest: Evernest.co Link: Connect with Evernest Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 180: The WHO Hiring Process: Find A-Players, Avoid Bad Hires
Mar 201:01:20Tap to summarizeIn 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 =================================== Connect with Matt and Gray at Evernest: Evernest.co Link: Connect with Evernest Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 179: EOS & Traction - Making Order Out of the Chaos in Your PM Business
Feb 1601:07:38Tap to summarizeIn 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 chunks, from quarterly milestones to three-year objectives Why following a tried-and-tested operating system like Traction empowers you to grow better in the long term =================================== Connect with Matt and Gray at Evernest: Evernest.co Link: Connect with Evernest Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 178: How to Sell (or Buy) a Property Management Company: Our 9-Step Process
Feb 201:26:24Tap to summarizeMatthew 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 keep you top of mind when someone's selling their PM business When to pull in an NDA - and why How to close the deal (and score the best outcome) =================================== Connect with Matt and Gray at Evernest: Evernest.co Link: Connect with Evernest Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 177: Meet the New Co-Host: The Ops Leader Who's Helped Shape Evernest for 10 Years | Gray Hall
Jan 1901:00:51Tap to summarizeIn 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 behind Gray's first acquisition with Evernest, including what he'd do differently in 2026 =================================== Connect with Matt and Gray at Evernest: Evernest.co Link: Connect with Evernest Link: Follow Spencer's efforts at neverthirst Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (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.
Transcribe →
Episode 176: My Time at Evernest Has Come to an End… | Spencer Sutton
Jan 1200:34:15Tap to summarizeIn 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 going right The difference between fear-based decisions and purpose-driven ones Why the way you leave a company can define your legacy more than how you entered =================================== Connect with Matt, Spencer, and Gray at Evernest: Evernest.co Link: Connect with Evernest Link: Follow Spencer's efforts at neverthirst Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (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 2025.
Transcribe →