Getting to Hell Yes! Live with Daniel Cunningham

Is property management really a "people business"? Daniel Cunningham says it's not — and he has 20+ years of receipts to prove it. From running his own property management company in LA to founding Leonardo247 to serving as President of Vendoroo, Daniel has lived this industry from every angle. And what he's learned about maintenance, AI, and the workforce carrying the heaviest operational burden is uncomfortable, specific, and worth every minute. In this episode of Getting to Hell Yes, Guillermo and Daniel go deep on the ideas nobody wants to say out loud: → Why maintenance is the hardest AI problem in multifamily, not the least important one → The context-switching crisis destroying on-site teams (half-painted walls, flood calls, impossible job descriptions) → Why "we pay them the least we can to get them not to quit" is the real people-first policy in most operations → The 98% reliable vs. 65% unpredictable framework and why human-in-the-loop AI isn't a weakness, it's the standard → How AI changes the wage math and why some of those efficiency gains should actually go back to the people doing the work This one will make you think differently about where your greatest operational risk lives and who's carrying it. 🎧 Listen now wherever you get your podcasts. #GettingToHellYes #GTHY #IrisCX #MultifamilyHousing #PropertyManagement #PropTech #MaintenanceManagement #AIinRealEstate #MultifamilyOperations #Vendoroo #OperationalExcellence #Proptech2025 #RealEstateTech #WorkforceInnovation #MultifamilyLeadership #FutureOfWork #ArtificialIntelligence #ResidentRetention #MultifamilyTech #MaintenanceTech