The Multi-Family Property Management AI Playbook
The Multi-Family Property Management AI Playbook is a podcast for multi-family leaders who know AI is coming and want to understand what’s truly possible, what actually works, and what they need to know now..
Hosted by Daniel Cunningham, the show explores how AI can be applied inside real property management operations, from maintenance and vendor coordination to leasing, resident communication and other operational efficiencies. Each episode unpacks real-world implementations alongside the early questions operators care most about: where AI delivers value, where it falls short, what changes operationally, and what it takes to adopt it responsibly.
This isn’t futurism or vendor hype. It’s a practical guide for owners and operators who are evaluating AI, looking for signal over noise, and want a clearer view of both the opportunities and the tradeoffs before making real decisions.
Episodes
7 episodes
Ep 6 | The Gap Preventing Widespread Adoption of ‘AI’ in the Multifamily Industry w/ Tamela Coval
The multifamily industry doesn’t just have an AI adoption problem.It has a literacy problem.In this episode of the Multifamily Property Management AI Playbook, Daniel Cunningham sits down with Tamela Coval, Partner at Multifamily NE...
Ep 5 | AI Breaks Where Liability Lives w/ Daniel Cunningham
AI is getting easier to build and as a result we already see the business community losing sight of what's really important, what's difficult.Every day there areNew tools.More automation.Faster, more human-sounding models.
Ep 4 | How AI Can Step in When Your Digital Dashboard Fails Analog Property Operations in the Field w/ Rachael Becker
Your property doesn’t break in the dashboard.It breaks in the field.At 1:00 AM, when a pipe bursts or heat goes out, your system should answer one question: who needs help first? Most can’t.In this episode of The Multifamily...
Ep 3 | After-Hours Emergency Services Is the Easiest Way to Start Using AI in Property Management w/ Daniel Cunningham
Most property managers think adopting AI means rebuilding their entire operation.New systems.New workflows.A massive leap of faith.That’s where most AI initiatives stall.In this solo episode of The Multifamily Pr...
Ep 2 | You Can’t AI Your Way Out of a Broken Operating Model w/ Gregory Lozinak
Everyone in multifamily is being told to adopt AI.But there’s a problem hiding underneath the hype.You cannot AI your way out of a broken operating model.In this episode of The Multifamily Property Management AI Playbook...
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Ep 1 | The AI Inflection Point We're In For Multifamily Property Management w/ Pablo Gonzalez
Daniel Cunningham recently found a CEO to run his company, Leonardo24/7, and now serves as President of Multifamily at Vendoroo, where he is going all in on figuring out the AI future for multifamily. This podcast is an exp...
The Multi-Family Property Management AI Playbook Teaser
AI will solve everything.At least that’s what your inbox says.But after nearly 20 years in PropTech, Daniel Cunningham has seen the difference between real operational change and vanilla futurism. Some tools crash when they hit re...
