Multifamily Tech Gurus

Kerry W. Kirby

The Multifamily Tech Gurus Podcast Series brings you the latest real-world experiences of PropTech innovator Kerry W. Kirby and technologist James W. Lancaster. Kerry and Jimmy live on the technology side of the multifamily housing industry. Kerry has built an award-winning company, 365 Connect, the multifamily industry's leading innovator in AI-driven marketing, leasing, and resident engagement platforms, that he founded over two decades ago, and Jimmy leads product development at the company. Together, they are on the frontline of managing their team of developers, customers, and all the craziness in-between.

  1. قبل ٥ أيام

    Controlling The Data Flow: The Power Shift of Owning Your Integrations

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they unpack one of the most critical drivers of performance in modern property operations: control of your data flow. In today's multifamily tech stack, data moves across multiple systems—but operators often don't control how it flows; instead, fragmented vendor-controlled integrations often do. In this episode, Kerry and Jimmy explore the power shift that occurs when operators take ownership of their integrations. They break down how controlling data pipelines unlocks real-time visibility, improves accuracy across marketing and leasing workflows, and enables smarter, faster decision-making. From eliminating data silos to reducing dependency on third-party constraints, the conversation highlights why an integration strategy has become just as important as the systems themselves. Kerry and Jimmy's Words of Wisdom: "The systems don't matter if you don't control how they connect. The real power isn't in the software—it's in the flow of data between it. When integrations are fragmented, your visibility is limited, your decisions are delayed, and your operations become reactive. But when you own the way data moves across your ecosystem, everything changes—workflows become seamless, and your digital service becomes more robust. In today's environment, controlling your data flow isn't just a technical advantage—it's a competitive one." Resources: Uniquely curated integrations built for simplifying data.

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  2. ٩ أبريل

    AI-Generated Software: The Hidden Risk Nobody Talks About

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they take a closer look at one of the fastest-growing trends in technology—and one of its least discussed consequences: the hidden risks of AI-generated software. Behind the excitement of "10-minute apps" and autonomous coding lies a much more complex reality, and writing code is only the beginning. In this episode, Kerry and Jimmy unpack the growing gap between AI-assisted development and enterprise-grade software engineering. They explore the risks of security vulnerabilities, poorly structured architecture, and compliance exposure that can arise when AI-generated code moves into production without experienced technical oversight. Most importantly, they tackle the critical question few are asking: when AI writes the software, who ultimately owns the responsibility if something goes wrong? Kerry and Jimmy's Words of Wisdom: "AI can generate code in seconds—but responsibility for that code doesn't disappear. Speed may be automated, but accountability never is. Just because a machine can assemble an application quickly doesn't mean the risks disappear. Every line of code still carries implications for security, performance, privacy, and reliability. When that software touches real users, real data, or real transactions, someone ultimately must stand behind it. AI may accelerate development, but the duty to review, secure, and validate that code still belongs to those deploying it." Resources: Tomorrow's Intelligence Built for Today's Renters

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  3. ٢ أبريل

    Approval to Obligation: The Art of Securing Pre-Lease Payments

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they explore one of the most overlooked and operationally sensitive moments in the renter journey: the window between application approval and lease execution. This is the space where intent must become commitment, and where operators must secure deposits, administrative fees, and financial obligations before the ink hits the lease. In this episode, Kerry and Jimmy break down the mechanics behind securing pre-lease payments the right way. When an applicant is approved, the clock starts ticking. Without a structured process to collect deposits and administrative fees promptly—and with proper disclosures—operators risk last-minute cancellations, inventory disruption, and unnecessary vacancy loss. They discuss how clear timelines, transparent fee communication, and digitally executed acknowledgments turn verbal intent into enforceable commitment. Kerry and Jimmy's Words of Wisdom: "The gap between approval and lease is where revenue quietly slips away. Deposits and admin fees aren't just payments—they're proof of intent. When structured properly, they transform a verbal yes into a financial commitment, protecting occupancy, stabilizing projections, and reducing last-minute fallout. In today's environment, securing those fees isn't about collecting money—it's about establishing obligation and ensuring that approval actually converts into an executed lease." Resources: Move Approved Applicants to Signature Ready Leases Instantly

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  4. ١٢ مارس

    Compliance Confusion: The Overuse of The Fair Housing Excuse

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they explore a common but rarely discussed challenge in property management: the growing tendency to invoke the Fair Housing Act as a catch-all explanation for policies, decisions, or situations that onsite teams struggle to clearly articulate. In this episode, Kerry and Jimmy unpack how misunderstandings or overgeneralizations about Fair Housing compliance can create confusion for renters and staff alike. While the law is designed to ensure equal opportunity and prevent discrimination, it is often cited as the reason behind operational policies that have little to do with the actual requirements of the actual law. When that happens, it not only undermines credibility with renters but also signals a deeper gap in training and policy communication. Kerry and Jimmy's Words of Wisdom: "Fair Housing is one of the most important protections in our industry—but when it becomes the default answer for everything, it stops educating and starts confusing. When teams rely on it as a catch-all response, it erodes credibility with renters and highlights a deeper gap in training and understanding. True compliance isn't about invoking Fair Housing at every turn—it's about knowing the law, applying it correctly, and being able to explain your policies with clarity." Resources: Delivering Built-In Compliance Across Every Interaction

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  5. ٥ مارس

    Software Disruption: Will AI Replace The Multifamily Tech Stack?

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they tackle one of the biggest questions facing property technology today: Is artificial intelligence about to replace the traditional multifamily tech stack, redefine it, or completely replace the dominant SaaS model that has existed for decades? In this episode, Kerry and Jimmy explore whether AI will eliminate standalone tools, collapse bloated tech stacks, and transform SaaS platforms into autonomous operating systems. They examine the rise of agentic systems, AI-driven workflow execution, and conversational interfaces that sit above traditional software and manual inputs. This conversation moves beyond hype, breaking down what disruption actually looks like, what remains irreplaceable, and how operators should rethink models. Kerry and Jimmy's Words of Wisdom: "We're moving from clicking through systems to commanding outcomes—and that changes everything. For years, operators have been trained to navigate dashboards, toggle between platforms, and manually push workflows forward. But AI flips that model. Instead of working inside software, you instruct intelligence to execute across it. The shift from user-driven inputs to outcome-driven orchestration doesn't just improve efficiency—it redefines the role of software itself." Resources: Empowering managers and renters to thrive in an AI-driven world.

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  6. ٢٦ فبراير

    Rewriting The Renter Journey Through AI and Automation

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they explore how artificial intelligence and automation are fundamentally rewriting the renter journey—from discovery to residency. What was once a fragmented path built on listings, lead forms, and manual follow-ups is being replaced by intelligent, connected systems that anticipate needs, guide decisions, and execute in real time. In this episode, Kerry and Jimmy unpack how AI-driven discovery engines, conversational interfaces, autonomous marketing, and workflow automation are collapsing timelines, removing friction, and reshaping expectations across every renter touchpoint. They discuss why the renter journey is no longer linear, why speed and consistency now define experience, and how operators who rely on yesterday's tools are quietly losing relevance in today's on-demand economy.  Kerry and Jimmy's Words of Wisdom: "The renter journey isn't being optimized anymore—it's being rewritten. AI and automation are no longer tools behind the scenes; they're becoming the experience itself. From how renters discover communities, to how decisions are guided, to how leases are executed, intelligence is now embedded into every moment of the journey—and the operators who understand that aren't just improving performance, they're redefining what modern renting looks like." Resources: Tomorrow's Intelligence Built for Today's Renters

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  7. ١٩ فبراير

    Multifamily Conferences: When the After-Party Becomes the Main Event

    Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they take an unfiltered look at what multifamily conferences have quietly become—and what they were supposed to deliver. In an industry that spends millions each year on travel, passes, booths, and sponsorships, a hard question has emerged: are we investing in knowledge, or just underwriting nightlife? In this episode, Kerry and Jimmy challenge the growing culture of empty breakout rooms, half-attended day-two sessions, and conference agendas that seem to orbit cocktail hours more than classrooms. They dig into why so many teams show up for the parties but disappear when it's time to learn—and what that says about leadership expectations, accountability, and how conference success is being measured. When photos flood social feeds but actionable insights never make it back to the office, something is broken. Kerry and Jimmy's Words of Wisdom: "Every conference trip is an investment in organizational intelligence. The return isn't the badge, the party, or the photos—it's the knowledge your team brings home and how that knowledge strengthens the company. Attendees should come back with clear takeaways, competitive insights, and ideas that translate into better decisions. If conferences don't make your business smarter, they don't deserve your budget." Resources: Where will we be making waves next?

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The Multifamily Tech Gurus Podcast Series brings you the latest real-world experiences of PropTech innovator Kerry W. Kirby and technologist James W. Lancaster. Kerry and Jimmy live on the technology side of the multifamily housing industry. Kerry has built an award-winning company, 365 Connect, the multifamily industry's leading innovator in AI-driven marketing, leasing, and resident engagement platforms, that he founded over two decades ago, and Jimmy leads product development at the company. Together, they are on the frontline of managing their team of developers, customers, and all the craziness in-between.

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