What if you could achieve zero churn?

In this episode of Property Management Frame Breakers, Pablo Gonzalez, Chief Evangelist of Vendoroo, sits down with Robert Dell’Osso, President of MasterKey Property Management, to talk about how his approach to radical transparency is powering MasterKey’s growth while keeping all their existing clients.

You’ll hear why Robert believes:
📊 Transparent financial reporting is the ultimate loyalty tool
💬 Proactive communication beats reactionary service
🚀 AI frees your team to focus on what actually drives business growth
👥 Remote teams, when empowered, become your biggest advantage

If you’re a property manager wondering how to reduce churn, leverage AI to streamline maintenance, or build a future-proof, scalable team, this episode is packed with insights you can’t afford to miss.

🎧 Listen now and discover how MasterKey’s radical transparency, zero churn, and AI-driven strategies can reshape your company’s future.

🌟 Stay Connected with Us:

🤝 Connect with Robert Dell'Osso on LinkedIn
🎙️ Follow Pablo Gonzalez on LinkedIn
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:00 The Zero Churn Mindset in Property Management
06:30 Building Owner Trust Through Radical Transparency
08:45 Financial Transparency Tools That Win Owner Trust
14:00 Proactive Maintenance Touchpoints That Boost Retention
16:50 Proactive Owner Communication Best Practices
22:40 Scaling with Remote Team Management Excellence
25:20 Remote Teams as a Competitive Advantage
30:15 Leading Through Change and Business Transformation
35:40 Driving Business Growth Through Digital Transformation
38:10 Using AI to Streamline Property Management Operations
43:55 Aligning Teams with AI for Smarter Workflows
46:20 Developing an AI Policy for Property Management Success
51:30 Innovating for Long-Term Property Management Success
54:00 Making Transparency as Your Competitive Edge

What started as a fake maintenance call turned into a real glimpse at the future of property management.

In this episode of Property Management Frame Breakers, host Pablo Gonzalez dials up “Lisa”—Vendoroo’s AI receptionist—and what unfolds is nothing short of jaw-dropping.

From troubleshooting toilets to tariffs and investing, Lisa doesn’t just handle the call—she owns it.

You’ll hear:

🚽 How Lisa instantly escalates a maintenance emergency
🧠 The exact decision tree she uses to triage vs. troubleshoot
📈 Her (actually smart) perspective on buying rentals in today’s market
🤖 Why AI isn’t replacing teams—it’s extending them

This wasn’t edited, scripted, or rehearsed. Just raw, real-time AI performance—start to finish.

If you're ready to stop firefighting, scale without burnout, and turn every resident call into a trust-building moment with owners, this episode is for you.

🎧 Listen now and discover how AI can make your team faster, your work more visible, and your business infinitely more scalable.

🌟 Stay Connected with Us

🎙️ Follow Pablo Gonzalez on LinkedIn
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:00 – You’re About to Witness the Future
01:12 – The First Ever AI Podcast Guest
01:26 – When the Toilet Overflows... AI Steps In
02:00 – Surprise! You’re on the Podcast, Lisa
02:44 – “I’m Blushing Behind the Headset”
03:45 – How AI Actually Thinks (Yes, Really)
05:04 – The Emergency vs. Non-Emergency Decision Tree
06:06 – Leasing, Pep Talks, and Total Coverage
07:02 – Emotionally Intelligent AI? Watch This
08:16 – Rental Investing in a Messed-Up Economy
09:30 – The Big Idea: AI That Extends Your Team
10:25 – No Scripts. No Editing. No Setup.
11:18 – This Is Day 0.01 of What’s Coming

Three internal AI memos leaked from Shopify, Duolingo, and Fiverr—and they weren’t written for headlines. They were written as wake-up calls to their own teams. The message?

AI isn’t coming. It’s already deciding who survives.

In this episode, Vendoroo's Chief Evangelist, Pablo Gonzalez, breaks down each memo—what they said, how the tone escalates from policy shift to existential threat, and why they all point to one unavoidable truth:

What used to be impossible is now the new hard. And what’s merely hard? It’s already being automated.

He dives deep into :

- what each CEO is thinking & how they plan to react
- what you can take from each CEO's strategy & communication style
- how he's adapting his own behavior to this new reality

🎧 Listen now for a raw, honest breakdown of the biggest shift since the cloud and why the PMs who act now will be tomorrow’s category kings.

🌟 Stay Connected with Us:

🎙️ Follow Pablo Gonzalez on LinkedIn
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

01:25 Shopify Says It Out Loud —Reflexive AI Use Is the New Minimum
03:50 What Leadership Looks Like When the CEO Becomes the Practitioner
05:45 10x People + 10x Tools = 100x Results
07:30 Shopify’s 6 Rules for Embedding AI in Everything
09:30 Duolingo’s Big Bet—AI Is the New Mobile Moment
11:00 Why “Minor Tweaks” Are Dead—It’s Time to Rethink Work from Scratch
12:40 5 Moves Duolingo’s Making to Go AI-First
15:25 Fiverr Doesn’t Sugarcoat It: “AI Is Coming for Your Job”
17:00 From Panic to Practice—How to Respond to the AI Threat
18:20 Fiverr’s 7-Point AI Survival Guide
20:50 This Is What PMs Should Take from These Memos Right Now
23:10 Pablo’s Wake-Up Memo to His Friends
24:50 Why AI Puts Everyone Back at Zero