Ep 70 | This Multifamily Veteran Is Betting Big On AI w/ Daniel Cunningham

What would make a 25-year multifamily veteran, who has already built a successful tech company, decide to bet big on a different platform?

The answer has little to do with leasing bots and everything to do with solving the single hardest, most chaotic part of property management: maintenance.

In this episode, Pablo Gonzalez sits down with Daniel Cunningham (founder of Leonardo 24/7 and now part of Vendoroo) reveals why maintenance triage is the true AI frontier in multifamily and how solving it unlocks NOI gains, reduces burnout, and transforms resident experience into hospitality-level service.

You’ll Learn:

👉 Why the “easy wins” in AI (leasing calls, chatbots) barely scratch the surface of property management’s biggest challenges
🛠️ How Vendoroo is solving maintenance triage (the most complex and burnout-inducing part of the job)
🤖 Why the difference between automation and true AI is the difference between a checklist and a teammate
🚀 How the role of property managers will evolve into hospitality-driven ambassadors as AI takes over admin and triage

Whether you’re an operator, investor, or technologist, this episode will reshape how you think about AI’s role in multifamily and why those who embrace it will create more resilient, human-centered communities.

🎧 Listen now and discover why Daniel is betting everything on AI and why solving the hardest problem in property management depends on it.

🌟 Stay Connected with Us:

🤝 Connect with Daniel Cunningham on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:00 From Hard Problems to Real Solutions
05:32 The Easy Wins in AI: Leasing & Call Centers
12:45 The Hard Problem: Maintenance Triage
18:10 Why Technicians Are Burning Out
24:20 The After-Hours Cost Drain
30:15 Daniel’s Origin Story & Leonardo 24/7
38:05 Automation vs. True AI
46:40 Cruise Control vs. Self-Driving AI
52:18 Why Daniel Bet on Vendoroo
53:45 The Future of Multifamily: How AI Will Reshape the Industry