What happens when a 11,000-unit operator sells to Greystar and doubles down on PropTech?

In this episode of Getting to Hell Yes, host sits down with Dave Marcinkowski, co-founder of Madeira Residential and founder of Quext Smart Apartment Solutions, for a high-energy conversation about the future of multifamily operations, technology adoption, and what it really means to let go of something you built.

Dave's journey from bookkeeper to co-founder is remarkable on its own but what's even more compelling is what happened after he sold Madeira's management company to Greystar. Freed from day-to-day operations, Dave is now all-in on the tech revolution reshaping multifamily and he's got a front-row seat, a sandbox of 11,000 units, and zero patience for legacy systems that don't play nice with each other.

This episode is a masterclass in operator-to-owner evolution, the PropTech buy cycle, and why the next wave of innovation won't come from the top down, it'll come from the maintenance tech with a better idea.

💡 If you're an operator, asset manager, or PropTech founder trying to crack the multifamily market, Dave's perspective is the inside lane you've been looking for.

🎙️ Topics covered:

• Selling to Greystar: what prompted the decision & what came next
• Why the "data moat" is dead and free data flow is the future
• Smart apartments, managed Wi-Fi, and owning a retail electric provider
• How AI is being built from the grassroots up not the boardroom down
• Why operators can't get their ideas funded (and how to fix it)
• "Growth occurs in the hard spaces" advice from 20+ years in the trenches

#IrisCX #GTHY #MultifamilyRealEstate #PropTech #SmartApartments #ApartmentOperations #AIinRealEstate #PropertyManagement #RealEstateTech #AssetManagement #MultifamilyInvesting #Quext #MadeiraResidential #PropertyManagerLife #RealEstatePodcast #FutureOfWork #OperatorMindset #TechAdoption #RealEstateInnovation #Entrepreneurship

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

The AI Reckoning in Multifamily: Tyler Christiansen on Centralization, CRM Adoption & What Operators Actually Need | Getting to Hell Yes

Tyler Christiansen built Funnel into one of the most strategic platforms in multifamily by solving a problem the industry didn't want to admit: CRM adoption is the dirty secret nobody talks about.

In this conversation, Tyler breaks down the shift from property-centric to renter-centric operations, why centralization is the unlock for AI, and how operators are rethinking lead quality over lead volume.

🎯 IN THIS EPISODE:

→ The CRM adoption crisis: Why most platforms don't get used

→ Centralization as the foundation for AI (not the other way around)

→ From property-centric to renter-centric: What changes operationally

→ Lead quality vs. lead volume: The death of spray-and-pray marketing

→ Why AI won't replace leasing agents, it gives them superpowers

→ The customer's customer principle: Understanding asset managers, not just operators

→ How Funnel landed 4 REITs by building community, not pitching

💡 KEY INSIGHTS:

"Nobody buys Funnel because of my pitch. They need customer stories. Once you have the story, you're just making it safer for them."

"Centralization isn't a nice-to-have anymore. It's table stakes for AI to work. You can't automate chaos."

"AI will unlock ten agents doing the work of fifty, not replace them. The question is: what do those ten agents do with their time?"

"Your customer's customer matters. We sell to operators, but their bosses, asset managers, investors, care about different things. If you don't understand that, you'll miss the deal."

THE NESTIO-TO-FUNNEL PIVOT:

In 2018, Tyler joined Nestio, a NYC broker management tool for StreetEasy. Great tech, wrong market. The TAM was too small. The problems didn't translate outside NYC.

"New York runs completely different than anybody else. Canada is closer to multifamily than New York is."

Tyler led the pivot: same talented team, different problem. They repositioned entirely from broker tool to operator platform, from NYC-only to national scale.

The result? Funnel now serves the largest multifamily operators in America.

ADVICE TO HIS YOUNGER SELF:

"Stay humble. Know there's something to learn at every stage. Every time you think you've made it, you get a gut punch on something you weren't expecting."

"Understand your customer's business. I've never run a multifamily portfolio, but I get to consult with the largest operators in America. That's through osmosis, learning, studying."

🎙️ ABOUT GETTING TO HELL YES:

Conversations with multifamily and PropTech leaders on building value, creating alignment, and achieving confident commitments.

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#Multifamily #PropTech #Funnel #TylerChristiansen #AI #Centralization #CRM #LeasingTech #RealEstate #PropertyManagement #GettingToHellYes #SaaS #Leadership #Community #IrisCX #GTHY