What does it take to grow a property management company to 600 doors and what happens when you hit the wall?

In this episode, Marc Cunningham sits down with David Normand of Vendoroo to break down his journey from scaling a property management company from under 100 doors to 600 in just a few years. David shares the simple four-word tagline that fueled that growth "Dave is your guy" and why trust, not technology, is still the foundation of winning owner clients.

But growth came with a cost.

At 600 doors, David hit the same problem most operators face: how do you scale yourself? That challenge led him down a path into workflow design, systems thinking, and ultimately AI-powered maintenance solutions.

This conversation dives into how AI is transforming property management maintenance from 24/7 work order handling to automated triage, vendor coordination, and improved owner communication. It also explores the real operational pain points property managers face and how technology can solve them without replacing the human element.

If you're trying to grow your portfolio, reduce maintenance headaches, or understand how AI fits into your business, this episode delivers both strategy and real-world application.

Contact Vendoroo at https://vendoroo.ai/

Clockwork Media - revolutionize your property management marketing

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Vendoroo- An always-on AI teammate to handle all aspects of maintenance

Enterprise Bank & Trust - Property Management banking specialists

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

How do you market to new clients without spending hours creating content or getting stuck on camera?

In this episode, Marc Cunningham sits down with Brent Holmes of Clockwork Media to explore how AI-generated video is changing the way property managers attract and convert new owner clients.

Marc has long emphasized the importance of educational video in building trust and generating leads, but execution has always been the biggest hurdle. Brent explains how AI avatar technology removes that barrier completely, allowing property managers to create professional, high-quality videos without filming, editing, or production headaches.

From creating a digital version of yourself to using a custom avatar, this approach makes it easier than ever to produce consistent marketing content. They also discuss how video can be used beyond marketing supporting owner education, tenant communication, and internal training.

If you've struggled to create video content or have avoided it altogether, this episode shows how to finally execute and use video as a true growth tool for your business.

Clockwork Media - revolutionize your property management marketing at https://clockworkmediainc.com/

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Enterprise Bank & Trust - Property Management banking specialists

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

What are the biggest opportunities in property management right now and are you missing them?

In this episode, Marc Cunningham sits down with Peter Lohmann, owner of RL Property Management (750 doors) and founder of the Crane community for property management business owners. Peter shares lessons from the opportunities he wished he had pursued earlier from buying more rental homes after the 2008 housing crash to going all-in on social media platforms early.

But this conversation isn't about regrets, it's about recognizing the next opportunities before they pass you by.

Marc and Peter discuss how business owners should think about their real job as CEO, why stepping away from the day-to-day operations is essential for long-term growth, and how Peter's "Crane Break" concept encourages property managers to fully disconnect from their business to unlock new ideas and leadership growth.

They also explore emerging opportunities around AI, knowledge sharing, and industry collaboration along with Peter's vision behind Crane, a private community designed to help experienced property managers grow faster and build time freedom.

If you're stuck in the daily grind of property management, this episode is a powerful reminder to lift your head up, look for opportunities, and press the advantage when you find them.

Crane - join the top PM group at https://www.joincrane.co/

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Lead Simple - manage more doors with less stress using LeadSimple

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

How does a property management company generate 1,400 owner leads in a single year without running pay-per-click ads?

In this episode, Marc Cunningham brings on Kristen Ewen of PMW (Property Manager Websites) and Rentvine to analyze Grace Property Management's website live. Instead of theory, this is a real breakdown of what's actually driving owner leads and where the content gaps still exist.

They discuss the blog topics and legal updates that generate the most traffic, why pricing pages are critical for both Google and AI visibility, and how AI tools are reshaping search behavior. Kristen also explains why authenticity and expert opinion matter more than ever and how property managers should (and shouldn't) be using AI to create content.

If you want more owner leads in 2026, this episode offers a tactical look at website strategy, SEO, AI optimization, and the small tweaks that drive major results.

Contact Kristen and her team at PMW at https://www.propertymanagerwebsites.com/

Upkeep Media: Get a free property management lead gen analysis

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Lead Simple - manage more doors with less stress using LeadSimple

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

In-house maintenance can transform a property management company — or create operational chaos. So how do you know when it makes sense?

In this episode, Marc Cunningham sits down with Melissa Sharon of FirstRate Property Management (1,200 doors in Boise, Idaho) to break down the real pros and cons of running in-house maintenance. Melissa shares how her team structured a separate maintenance division, why quality control and response time improved, and how it became a profitable arm of their business.

They also dive into strategic planning retreats, taking a leadership team to Mexico after hitting growth goals, buying a company from the previous owner through an SBA loan, and what it looks like to run a 28-person company with your spouse.

If you're debating bringing maintenance in-house, planning your next growth phase, or thinking about long-term ownership, this episode offers practical insight from someone who's done it.

1st Rate Property Management

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Lead Simple - manage more doors with less stress using LeadSimple

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

What does it really take to grow a property management company from scratch and do it while building a life outside the business?

In this episode, Marc Cunningham sits down with Carson Hamann of Bobcat Property Management to unpack her journey from buying her first rental at 18 years old to running a 275-door property management company in Northern Nevada. Carson shares how she grew mostly organically, what she learned from acquiring (and later shedding) doors early on, and how she built professionalism and confidence as a young operator in a traditionally male-dominated industry.

The conversation dives into work ethic, mindset, hiring challenges, setting boundaries as a kind-hearted leader, and the systems that helped Carson manage growth without burning out. Carson also explains how she generates consistent owner leads, often averaging one per day, largely through agent referrals and Google reviews, without heavy ad spend.

This episode is an honest look at sustainable growth, leadership development, and balancing ambition with family, motherhood, and life outside the office.

Bobcat Property Management

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Lead Simple - manage more doors with less stress using LeadSimple

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

Can a property management company add real estate sales or should a real estate sales company bolt on property management?

In this episode, Marc Cunningham sits down with Justin Woodall to unpack how Justin successfully built a property management division out of an already thriving real estate sales business. Justin shares why he chose to separate the two brands, how personality differences between sales and property management shape hiring decisions, and what operational structures made growth possible without burning out the owner.

You'll hear candid insights on referral strategies between sales and PM, how to protect online reviews, how to communicate sales services to owner clients, and why recurring revenue from property management ultimately creates more long-term enterprise value than sales commissions alone.

This episode is essential listening for operators weighing expansion opportunities, deciding where to focus limited resources, or thinking about how to build a business that scales beyond themselves.

Woodall Realty Group

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Lead Simple - manage more doors with less stress using LeadSimple

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.

How are you planning to generate new owner-client leads in 2026 and are you betting on tactics that actually work?

In this episode, Marc Cunningham sits down with Stephen Fox of Upkeep Media to break down the most effective, realistic strategies property management companies should be focusing on to drive owner leads next year. Instead of chasing shiny objects or short-term hacks, the conversation centers on organic SEO, Google reviews, YouTube, and education-based marketing that compounds over time.

Stephen explains why Google and YouTube still dominate owner search behavior, how AI search fits into the picture, and what PMs should prioritize depending on where they are in their growth journey. They also unpack why video marketing is one of the cheapest and most defensible lead-generation strategies available—and why perfection is not required to win.

This episode is a practical roadmap for PMs who want predictable lead flow, lower acquisition costs, and marketing assets that keep working long after they're created.

Upkeep Media: Get a free property management lead gen analysis

Property Manager Websites - the highest performing property management website in the industry

Venderoo- An always-on AI teammate to handle all aspects of maintenance

Lead Simple - manage more doors with less stress using LeadSimple

Rentvine - the property management software you can trust

Lending One - real estate loans for investors

Reconcile Daily - corporate & trust accounting experts

PMbuild - Marc's education for property managers

Denver Property Management - Grace Property Management website

This podcast is produced by Two Brothers Creative.