Unfiltered by PropertyManagement.com

In this episode of Unfiltered, Dylan Scroggins is joined by David Soles, Founder and CEO of KSD Solutions, to discuss what it takes to build and lead high-performing property management teams. David shares his journey from public education into property management, including his experience helping lead operations for a rapidly growing single-family rental portfolio. Drawing on that experience, he explains why scaling a property management business requires more than adding doors: it takes clearly defined roles, strong leadership, the right people in the right positions, and a shared understanding of what success looks like. Whether you're leading a property management company, managing a growing portfolio, or building a career in the industry, this conversation offers practical perspectives on developing stronger teams, improving operations, and using technology without losing the human touch. Links David on LinkedIn - /  David Soles | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter  Chapters   0:00 — How indecision slows maintenance, leasing and budgeting 1:55 — David's path from public education into property management 3:55 — Moving from leasing into operations and leadership 6:17 — Defining consistent service as a property management company scales 8:21 — Using sports positions and a shared playbook to build effective teams 13:09 — How clear leadership builds team confidence and makes winning the standard 15:15 — KSD's hands-on approach to helping property management companies grow 16:35 — Why decision-making pace and confidence matter in operations 19:52 — Using AI to improve efficiency while keeping people in key decisions 32:05 — "Humanoid": David's vision for the future of property management Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins sits down with Brian Kubash, President and Owner of Kader Property Management in Madison, Wisconsin, to discuss his journey from corporate executive to property management business owner through an entrepreneurship-through-acquisition (ETA) model. After working in wealth and investment management, Brian spent more than two years searching for the right property management company to acquire. Eighteen months after purchasing Kader Property Management, he has helped grow the business from approximately 400 doors to nearly 800. Brian shares what attracted him to the property management industry, what it was like stepping into a small business from a corporate background, and the operational and growth decisions that have helped shape the company. If you're considering acquiring a property management company, looking to grow your portfolio, or navigating the challenges of leading a property management business, this conversation offers practical insight into ownership, growth, and building a stronger operation.   Links Brian on LinkedIn - /  Brian Kubash | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter  Chapters 0:01 — Introduction to Brian and Cater Property Management 1:37 — How Brian got into property management through entrepreneurship by acquisition 3:29 — Brian's acquisition thesis and what attracted him to the industry 5:25 — The two-year search for a property management company to buy 7:27 — Growing Cater from about 400 to nearly 800 doors 8:49 — Building the team and investing in business development 13:22 — Cater's growth strategy and openness to acquisitions 16:20 — Brian's first three to six months as an owner 22:41 — How Cater uses AI while keeping people in charge of decisions 26:20 — Brian's outlook for the property management market in 2027   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins sits down with Drew Weinhold, Business Development Manager at Fetch Home Management in Lancaster, Pennsylvania, to discuss the unique challenges and opportunities of adding doors in a predominantly Amish community where referrals and relationships matter more than ever. With 65–70% of Fetch's owners identifying as Amish and many relying on phone calls, mailed contracts, and word-of-mouth referrals instead of email and digital communication, Drew has had to rethink what marketing and business development look like. He shares how building trust, maintaining strong client relationships, and understanding the community have become central to Fetch's growth. Whether you're a property manager, business development professional, or owner looking to grow your portfolio, this conversation offers a fresh perspective on relationship-driven growth, operational structure, and serving a unique market. Links Drew's Podcast: Spotify: https://open.spotify.com/show/7hfvzrJ2i6q8qExnuK9Tks Apple Podcasts: https://podcasts.apple.com/.../the-broken.../id6816262001  Fetch Home Management - www.fetchpm.com Drew on LinkedIn -  /  Drew Weinhold | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  Matt on LinkedIn -  / Matt Speer | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter    Chapters   0:00: Opening, with 65–70% of clients 0:32: Welcome and intro of Drew Weinhold from Fetch Home Management 2:00: Fetch's story, from zero to about 600 doors in eight years 5:05: Is "Business Development Manager" the right title? 11:35: Marketing to the Amish community 13:20: Signing contracts by mail and the three daily phone windows 15:39: Why Amish investors put their cash into real estate 24:27: Switching to AppFolio from seven separate tools 30:02: Growing by 230 doors, churn and owners selling 32:46: Lightning round, covering Opus Clip, podcast picks and "Opportunity" Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins is joined by Madeline Vinson, Head of Product at Haven AI, to explore her unique journey through the property management industry. From watching her family build a property management company to helping scale its operations, launching her own process consulting business, and now working at the intersection of property management and AI, Madeline brings a perspective shaped by experience at every level. They discuss how property managers can use AI to streamline operations, build leaner teams, and make smarter business decisions without getting caught up in every new technology. Madeline also shares lessons from growing up in the industry, getting fired by her parents as a teenager, and learning to approach difficult interactions with greater empathy. If you're a property manager looking to understand where AI fits into your business while building a stronger team and delivering a better customer experience, this conversation offers practical insights on what to prioritize next.   Links Madeline on LinkedIn - /  Madeline Vinson | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter  Chapters   0:00 – Welcome and meeting Madeline, head of product at Haven AI 0:32 – Moving from Knoxville to Brooklyn, and the UT bar in Times Square 2:21 – Growing up in property management, and getting fired by her parents 4:28 – From managing her mom's inbox to leading a team and 1,000 doors 6:08 – Starting a consulting company and how Haven recruited her 10:36 – What Haven is building: an agentic operations platform 12:51 – AI questions for operators by door count 17:24 – How lean can a team get? Why agency and taste matter 22:31 – Vibe coding: what's worth your time and what isn't 31:36 – How property management changed her, and the lightning round   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins is joined by Casey Howe, Principal of Howzer Property Management in Massachusetts, about bringing a software and enterprise sales mindset into the property management industry. After spending nearly a decade building and leading sales teams in the SaaS and data management space, Casey entered into the property management world in 2018. He shares how his technology background helped him identify opportunities to improve service, why he chose to focus on small and midsize investors, and how his company rebuilt its business by focusing on the right clients, client retention, and financial performance. Casey also explains why customer success deserves more attention in property management, how his team uses AI to improve owner reporting, and why he believes operators shouldn't feel pressured to be early adopters of every new technology. Looking ahead, he discusses AI-driven price compression, the growing importance of operational efficiency, and the potential for increased consolidation among smaller property management companies.   Links Casey on LinkedIn - /  Casey Howe | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter  Chapters   00:00 — Introducing Casey Howe and the Northeast property management market 01:45 — From software sales to property management 05:14 — Why property management fit recurring revenue and technology 09:22 — Focusing on triple-deckers and scattered-site multifamily 10:15 — Letting go of 350 doors to find better-fit clients 17:03 — Applying enterprise sales skills to property management 21:23 — Making customer success a competitive advantage 27:12 — Defining Hauser's ideal customer profile 30:42 — Taking a measured approach to technology adoption 35:43 — AI, price compression, and the future of property management   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins talks with Matt Nicklin, Founder and Managing Broker at One Source Real Estate, about growing a property management company to around 200 doors through a combination of organic growth, acquisitions, and strong operations. Matt shares how he went from a background in technology to property management, why acquiring smaller operators can be an effective growth strategy, and what he looks for when taking over another company's book of business. He also discusses the importance of building the right team, putting people in the right seats, and knowing when an operator needs to stop doing everything themselves. They also discuss the changing property management market, the decline of traditional "intentional investors," the rise of accidental landlords, and why operators need to adapt their ideal customer profile as market conditions change.   Links Matt  on LinkedIn - /  Matt Nicklin | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter  Chapters   00:01 — Introducing Matt Nicklin and One Source Real Estate 01:41 — Growing a 200-door property management business 03:25 — Building the right team and hiring for fit 05:37 — Acquisitions as a growth strategy 08:43 — From tech to property management 09:23 — AI tools improving leasing and operations 12:43 — The path from 200 to 300 doors 13:53 — Shifting from investors to accidental landlords 17:42 — What excites—and concerns—Matt about the industry 24:18 — How property management changes you as a leader   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins talks with Declan McGonigal, CEO of myBeach Vacation Rentals in Myrtle Beach, South Carolina, about building a property management business across both the long-term and short-term rental markets. Declan shares how he got into property management, grew his vacation rental portfolio from just a handful of properties to more than 80, and later acquired a long-term management company that now manages around 285 properties. He explains why the two sides of the business operate with completely different teams, technology, and day-to-day demands. They also dive into the realities of running a highly seasonal short-term rental market, the challenges of relying on platforms like Airbnb, and why property managers need to turn platform guests into direct customers. Declan breaks down when short-term rentals can be a strong revenue opportunity, when the investment may not be worth it, and what owners need to consider before converting a property. The conversation also explores AI, including where Declan is already seeing meaningful results, why short-term rentals are harder to automate, and why chasing every new AI tool can become a distraction from the biggest bottleneck in your business.   Links Declan on LinkedIn - /  Declan McGonigal | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  Matt on LinkedIn -  / Matt Speer | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter  Chapters   01:50–03:58 — From Engineering to 80+ Vacation Rentals 05:34–06:35 — The Airbnb Dependency Problem 07:16–09:14 — Why Airbnb and Zillow Want to Own the Customer 09:43–12:14 — Short-Term vs. Long-Term: Two Different Ball Games 12:33–13:16 — Why Property Managers Love College Guests 19:09–20:59 — When a $1.5M Property Isn't Worth Going Short-Term 22:42–24:23 — Why AI Is Easier to Implement in Long-Term Rentals 25:00–26:09 — AI Can Be a Great Distraction 26:57–30:36 — How Property Management Changed Declan 32:18–32:36 — The Future of Property Management: "Disrupted"   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode of Unfiltered, Dylan Scroggins talks with Katie Linkous, President of Freedom Investment Group, about building a multi-company real estate business while keeping people at the center of property management. Katie shares her journey from working as an ICU nurse to becoming a real estate investor and leader of five companies. They dive into how Freedom Investment Group has built a business around property management, construction, brokerage, and nonprofit housing initiatives, including their work providing housing for people facing barriers to traditional housing. Katie also shares how her team approaches accountability, company culture, and creating a better experience for owners, tenants, and employees. The conversation also explores AI and technology, including how Freedom Investment Group uses tools like Claude and Rent Engine to increase capacity and give their team more time to focus on the "people things." Katie discusses the changing property management landscape, the importance of proving the value of professional management, and why she sees the future of the industry as an opportunity.   Links Katie on LinkedIn - /  Katie Linkous | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter    Chapters   0:00 — Why property management can change people's lives 2:16 — Family, parenting, and working together 5:05 — Building a business across property management, construction, and housing 9:01 — The nonprofit's housing mission and flexible management approach 12:37 — From intensive-care nursing to real estate entrepreneurship 17:09 — Putting people at the center of property management 21:36 — Creating a workplace culture built on accountability and care 25:59 — Using AI and technology to free teams up for human work 31:02 — Where the property-management industry is headed 34:21 — How the work has deepened Katie's empathy   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.

In this episode of Unfiltered, Dylan Scroggins is joined by Tony Cline, founder of Onyx Property Management Coaching, to talk about the lessons he's learned from building, scaling, and eventually selling a multi-state property management company. Tony shares how he went from managing roughly 30 doors to building a 330-door portfolio, expanding into six states, and navigating the challenges that come with growth, acquisitions, and leadership. He also draws on his experience as an ultra-runner to explain resilience, getting comfortable with discomfort, and pushing beyond the limits you put on yourself. They also dive into AI, founder bottlenecks, delegation, client selection, and what it really takes to build a business that can operate without the owner being involved in every decision.   Links Tony on LinkedIn - /  Tony Cline | LinkedIn  Dylan on LinkedIn -  /  Dylan Scroggins | LinkedIn  PropertyManagement.com -  https://propertymanagement.com/  The Kalmar Group -  https://thekalmargroup.com/pm   Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter    Chapters   00:00 – From Property Management to Ultra Running 03:15 – How Tony Got Into Property Management 06:40 – Building Systems Around 30+ Doors 10:35 – Knowing Which Clients You Should Work With 14:20 – The Reality of Growing Through Acquisitions 18:05 – How AI Will Change Property Management 22:00 – The Founder as the Biggest Bottleneck 25:00 – Stop Being the Genius, Become the Conductor 28:43 – Your Business Will Never Outgrow Your Capacity 31:30 – The Championship Formula for Scaling a PM Business   Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.  

In this episode, Dylan Scroggins is joined by Thomas Perfect, CEO of Uplift Property Management, to discuss his journey from running a 75-unit operation out of a small trailer to scaling the business to more than 1,000 doors. Tommy shares the leadership lessons that shaped his growth, the importance of building trust within a team, and how strategic staffing and performance-based equity helped create a culture focused on long-term success. They also explore the role of technology and AI in the future of property management, why thoughtful adoption matters more than chasing every new tool, and how trust and communication are becoming increasingly important in a rapidly changing industry. Tommy offers practical insights into building a resilient business, attracting top talent, and preparing property management companies for the next wave of industry disruption. Links Thomas on LinkedIn - / Thomas Perfect | LinkedIn Dylan on LinkedIn - / Dylan Scroggins | LinkedIn PropertyManagement.com - https://propertymanagement.com/ The Kalmar Group - https://thekalmargroup.com/pm Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter Chapters 00:01 — Intro to Tommy Perfect and Uplift Property Management 02:39 — How Tommy got started in property management 03:40 — Growing Uplift from a trailer to 1,000+ units 04:46 — The surprising story of how Tommy got hired 06:54 — Rapid growth from 75 to 550 doors overnight 09:24 — Staffing through explosive company growth 11:48 — The path from employee to 50% owner 13:23 — EOS, delegation, and Tommy's role as visionary 16:21 — AI, vibe coding, and guardrails for the future 22:09 — Generational change, trust, and why the market is shifting Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. Always perform your own due diligence before making any financial or business decisions.