Daniel Cunningham

The Multi-Family Property Management AI Playbook

Business EN ↓ 8 episodes

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...

Author

Daniel Cunningham

Episodes

Ep 7 | Moving Beyond "Good Enough" AI to Drive Greater Asset Value w/ Robert Salwasser 30.06.2026 40:03

Professional multifamily operators cannot afford to remain ignorant when it comes to AI. If you don't understand the tech you're buying, you’re just paying for an expensive way to automate the creation of more problems. In this episode, Daniel Cunningham talks with Robert Salwasser, Founder and President of IPS, about the shift from "Kindergarten AI" to agentic systems that act...

Ep 6 | The Gap Preventing Widespread Adoption of ‘AI’ in the Multifamily Industry w/ Tamela Coval 21.04.2026 40:57

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 NEXT, to break down what actually happened when they tried to teach operators AI: They had to stop everything… and start with “What is AI?” Because even senior leaders...

Ep 5 | AI Breaks Where Liability Lives w/ Daniel Cunningham 15.04.2026 23:05

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 are New tools. More automation. Faster, more human-sounding models. That’s where most AI conversations go. And it’s the wrong place to focus. In this solo episode of The Multifamily Property Management AI Playbook, Daniel Cunningha...

Ep 4 | How AI Can Step in When Your Digital Dashboard Fails Analog Property Operations in the Field w/ Rachael Becker 31.03.2026 37:32

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 Property Management AI Playbook, Daniel Cunningham sits down with Rachael Becker, CEO of RB Builds, an operations expert with 20+ years across real estate, construction, an...

Ep 3 | After-Hours Emergency Services Is the Easiest Way to Start Using AI in Property Management w/ Daniel Cunningham 24.03.2026 19:35

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 Property Management AI Playbook, Daniel Cunningham breaks down why after-hours emergency services are the easiest place to start. This is where operations are most exposed, where reside...

Ep 2 | You Can’t AI Your Way Out of a Broken Operating Model w/ Gregory Lozinak 17.03.2026 34:10

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, Daniel Cunningham sits down with Gregory Lozinak, advisor at GJL Real Estate Advisory and former COO, to talk about why many AI initiatives fail in property management. Greg s...

Ep 1 | The AI Inflection Point We're In For Multifamily Property Management w/ Pablo Gonzalez 10.03.2026 49:51

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 exploration in to what's coming. To kick off the Multifamily Property Management AI Playbook Podcast , we’re starting with a conversation where Daniel is on the other side...

The Multi-Family Property Management AI Playbook Teaser 03.03.2026 1:40

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 real-world data. Others actually change the math on NOI. The Multi-Family Property Management AI Playbook was created to be a filter. This show separates hype from signal...