Ep 138 | 3 Biggest AI Mistakes Teams Are Making

Ep 138 | 3 Biggest AI Mistakes Teams Are Making

500+ agentic AI rollouts into it, and ROO has shown us the same 3 mistakes keep being made: - Treating an agent as software - Turning it on to scale chaos - Unnecessary internal sabotage In this episode, Pablo Gonzalez, Chief Evangelist at Vendoroo, shows you why these mistakes are being made and how to avoid them. You'll Learn: 🔧 Why owners churn when maintenance creates stress, not just when returns drop ⚡ How AI speeds up responses, troubleshooting, and vendor dispatch 🎯 How AI adapts workflows by property, owner, and resident 🤖 The difference between AI that helps and AI that handles the job 🚨 Why software thinking, interruptions, and fear can break adoption 🎧 Listen now to learn how the best property management companies build trust in AI, accelerate maintenance operations, and create teams that embrace automation instead of resisting it. Want to see how to avoid these mistakes in real time? Register for our upcoming webinar on Thursday, June 11 at 3 PM EST and see how to break through these exact roadblocks to hit 90%+ automation! REGISTER HERE: https://us06web.zoom.us/webinar/register/3617805667417/WN_gwDCizSpR0qFn3WfWtpGZA#/registration [https://us06web.zoom.us/webinar/register/3617805667417/WN_gwDCizSpR0qFn3WfWtpGZA#/registration] 🌟 Stay Connected with Us: 🎙️ Connect with Pablo Gonzalez [https://www.linkedin.com/in/pablotheconnector/] on LinkedIn 📬 Subscribe to Vendoroo's Weekly [https://pablo-gonzalez-vendoroo.beehiiv.com/] Newsletter 💼 Follow Vendoroo [https://www.linkedin.com/company/vendoroai/] on LinkedIn 🌐 Visit Vendoroo's Website [https://vendoroo.ai/] Chapters: 02:29 — Why AI Feels More Overwhelming Than Ever 05:40 — Vendoroo's Track Record Across 500 Deployments 06:39 — Securing Team Buy-In For Safe AI Adoption 07:39 — The Core Thesis Behind Play Bigger 08:58 — Why Churn Gets Worse As You Scale 11:30 — Brian Rosenthal's Ten-Year Portfolio Exit 12:34 — Pablo's KTA Story And Investor Churn 15:29 — What Owners Really Want According To PM Trends 16:10 — Ending The Three-Hour Work Order Investigation 17:05 — How AI Troubleshoots Maintenance Around The Clock 18:59 — Creating Owner-Specific Maintenance Workflows 23:36 — Generative AI Versus Agentic AI 25:24 — Why Legacy Software Breaks In Modern Workflows 26:59 — The Four Paths To Agentic AI Adoption 28:48 — What 500 Deployments Reveal About Maintenance 31:09 — Risk One The Software Mindset 36:24 — Risk Two Interruptions Kill Momentum 40:34 — Risk Three Fear Leads To Sabotage 47:45 — The Story Behind Automating Toward Humans

Ep 137 | Is Your PMC Ready for the New Maintenance Standard?

Your team can’t answer every maintenance request in 15 seconds. But residents are starting to expect it. Owners still want updates, vendors still need coordination, and your staff is already buried trying to keep the workflow moving. In this mini episode, David Normand and Robert Dell’Osso break down why the next generation of owners, residents, and operators are forcing property management companies to rethink how work gets done. You'll Learn: 🔍 Why software fails when it’s bought before the constraint is clear ⚡ How owner and resident expectations changed the definition of efficiency 📱 Why texting is becoming the new front door for maintenance 🧠 Where form-based AI stops and agentic AI starts 📊 Why off-platform communication creates operational blind spots 🤝 How AI moves teams from task management to human engagement 🎧 Listen now to understand where maintenance operations are headed- and what it takes to meet the service standard owners and residents already expect. 🌟 Stay Connected with Us 🤝 Connect with David Normand [https://www.linkedin.com/in/davidnormand/] on LinkedIn 🤝 Connect with Robert Dell’Osso [https://www.linkedin.com/in/robertdellosso/] on LinkedIn 🎙️ Connect with Pablo Gonzalez [https://www.linkedin.com/in/pablotheconnector/] on LinkedIn 📬 Subscribe to Vendoroo's Weekly [https://pablo-gonzalez-vendoroo.beehiiv.com/] Newsletter 💼 Follow Vendoroo [https://www.linkedin.com/company/vendoroai/] on LinkedIn 🌐 Visit Vendoroo's Website [https://vendoroo.ai/] Chapters: 00:45 – Why Technology Fails After The Demo 01:15 – The Shiny Object Trap In Property Management 02:02 – Keeping Up With The Context Shifts 02:17 – What The New Level Of Owners Expect 02:41 – The One Business Day Standard Is Dead 02:41 – The New Standard Is Not Just Speed 04:10 – Texting Reveals A Bigger Service Shift 06:19 – Where Form-Based AI Reaches Its Limit 07:40 – Off-Platform Communication Kills Visibility 08:26 – Let ROO Own Maintenance 09:42 – Set It, Forget It, Be Human 10:02 – Humans Had To Own The Outcome First Before AI

Ep 136 | What AI Makes Possible In Maintenance Now w/ David Normand and Marc Cunningham

Maintenance runs 24/7. It does not wait for office hours. And owners do not trust a process they cannot see. That is why the shift from operator-managed coordination to AI-native autonomous execution. In this conversation, David Normand (Chief PM of Vendoroo) and Marc Cunningham (CEO of Grace Property Management & Real Estate) break down how ROO turns maintenance from a reactive bottleneck into a controlled, around-the-clock workflow- and what becomes possible when AI stops generating answers and starts helping operators make decisions. You’ll Learn: ⚙️ Why office hours no longer match resident expectations 🤖 How ROO moves beyond rigid troubleshooting 🧠 Why your best maintenance logic cannot stay trapped in one person’s head 📲 What happens after the resident submits the request 📈 What today’s automation numbers reveal about maintenance scale 🛡️ Where AI still needs human support 🎧 Listen now to hear how agentic AI helps property managers stop sleeping next to the emergency phone and start building a maintenance operation that works around the clock. 🌟 Stay Connected with Us 🤝 Connect with David Normand [https://www.linkedin.com/in/davidnormand/] on LinkedIn 🎙️ Connect with Marc Cunningham [https://www.linkedin.com/in/marc-cunningham-0110108/] on LinkedIn 📬Subscribe to Vendoroo's Weekly [https://pablo-gonzalez-vendoroo.beehiiv.com/] Newsletter 💼 Follow Vendoroo [https://www.linkedin.com/company/vendoroai/] on LinkedIn 🌐 Visit Vendoroo's Website [https://vendoroo.ai/] Chapters: 00:00 Show Kickoff 02:01 Meet David Normand 02:33 Northeast PM Challenges 03:38 Bravado And Candor 05:51 Getting Into Property Management 07:04 Scaling To 600 Doors 09:18 Burnout And Going Big 10:31 FedEx Workflow System 12:45 From PM To AI Maintenance 16:41 Vendoroo Automation Today 19:23 How The AI Handles Calls 21:37 Instant Work Orders 21:57 AI Maintenance Texts 22:41 July 4th Washer Save 24:44 Smart Tips From Data 25:34 Custom Workflows Context 27:11 Vendor Selection Logic 28:14 Owner Trust Reporting 31:40 Scheduling And NTEs 33:05 Reviews And Vendor Chasing 34:10 AI Maturity Journey 35:46 Two Takeaways For PMs 37:05 Guarantee And Accuracy 37:39 Where To Find Vendoroo 39:17 Final Advice On Edge Cases

Ep 135 | 2 New PM Industry Reports Show 1 Glaring Misconception

If you are treating net operating income as your ultimate defense against owner churn, you are banking on a metric that 92% of rental property investors say they are willing to sacrifice for a better experience. The gap between delivering returns and keeping owner trust has never been clearer. Pablo Gonzalez, Chief Evangelist at Vendoroo, breaks down the new PM Trends Report from Jordan Muela and Peter Lohman and the propertymanagement.com Maintenance Software Report - and the bigger story they begin to reveal when viewed together. You'll Learn: 📊 Why 92% of owners would trade cash flow for a better experience 🏠 How maintenance friction creates kitchen table arguments and churn risk 🤝 Why AI gives teams bandwidth to protect owner trust 🏆 What the PM.com rankings reveal about perception versus performance ⚙️ How maintenance AI is shifting from task support to owning more of the work 🎧 Listen now to understand why owner retention is no longer defended by NOI alone, and what the latest PM reports reveal about the future of maintenance operations. 🌟 Stay Connected with Us: 🎙️ Connect with Pablo Gonzalez [https://www.linkedin.com/in/pablotheconnector/] on LinkedIn 📬Subscribe to Vendoroo's Weekly [https://pablo-gonzalez-vendoroo.beehiiv.com/] Newsletter 💼 Follow Vendoroo [https://www.linkedin.com/company/vendoroai/] on LinkedIn 🌐 Visit Vendoroo's Website [https://vendoroo.ai/] Chapters: 00:00 – Two Industry Reports Point To One Misconception 01:45 – The Gap Between PM Output And Owner Expectations 03:20 – Why Owners Trade Cash Flow For Fewer Headaches 04:14 – The Headache That Pushed An Investor Out Of Real Estate 06:12 – One Maintenance Bill Can Break Owner Trust 07:30 – Kitchen Table Arguments Create Churn Risk 08:12 – Why Net Operating Income Will Not Prevent Churn 09:16 – AI Bandwidth Protects The Owner Relationship 10:58 – Performance Outcomes Versus Market Perception 11:41 – The Architectural Shift From Coordination To Execution 14:14 – Putting Out Embers Before Resident Issues Escalate 15:55 – Are You Playing On Hard Mode With Legacy Software? (The Threat) 16:48 – Playing The New Maintenance Game (The Opportunity)

Ep 134 | Mediocre AI is Keeping Property Managers Trapped w/ Stacey Salyer

If you are still anchoring your belief in what is possible to legacy software, you are keeping yourself confined to a version of property management that no longer exists. Pablo Gonzalez and Stacey Salyer reveal why the industry is trapped in a cycle of mediocre AI exposure and how a new category of Agentic teammates is pushing the boundaries of what is operationally possible. 🤖 The difference between Generative AI and Agentic AI 📉 How Agentic AI makes the "250 doors per person" rule obsolete, allowing one person to oversee 1,500+ doors 🏥How to stop the task-chasing cycle and reclaim your mental health through automated maintenance decision-making 🕵️ Using AI agents to scan years of raw data to see how a company actually operates before you buy it 👩‍💼 Moving from a "worker bee" to an owner-broker by removing the mental load of daily minutiae 🏨 Why the future of property management is modeled after world-class restaurants, not just fixing toilets. 🎧 Listen now to understand how to move from a manual bottleneck to a high-hospitality operator. 🌟 Stay Connected with Us: 🤝 Connect with Stacey Salyer [https://www.linkedin.com/in/stacey-salyer-39254012/] on LinkedIn 🎙️ Connect with Pablo Gonzalez [https://www.linkedin.com/in/pablotheconnector/] on LinkedIn 📬Subscribe to Vendoroo's Weekly [https://pablo-gonzalez-vendoroo.beehiiv.com/] Newsletter 💼 Follow Vendoroo [https://www.linkedin.com/company/vendoroai/] on LinkedIn 🌐 Visit Vendoroo's Website [https://vendoroo.ai/] Chapters: 04:16 – How Fast AI Accelerates 05:59 – The Mistake Of Bringing Past To The Future 07:18 – Why Old Categories Fight New Categories 11:00 – How AI Thought Leadership Becomes Decentralized 11:48 –  Agentic AI vs. Generative AI 13:43 – The Current Level of AI's Judgment 14:14 – Maintenance As PM's Hardest Problem 15:10 – Sign Of A Great Hire 15:31 – Why Vendoroo Had To Own The Outcome 16:51 – What 98% Automation Looks Like In Maintenance 22:10 – How AI Changes Door Count Capacity 22:43 – The Role Of Humans During Automation 23:37 – Property Management Is Relationship Building 25:11 – Why Managing By Exception Becomes Possible With AI 29:58 – Why Hospitality Becomes The Next Differentiator 34:17 – Why Property Managers Become Jaded 39:06 – How AI Can Help Acquisition Due Diligence 41:55 – How AI De-Risks Post-Acquisition Operations 43:14 – Why Implementation Risk Matters More Than Tech 49:20 – Stacey’s Vision For Gen Z In The PM Industry 51:25 – Why Stacey Wants More Women Buying Businesses