Unfiltered by PropertyManagement.com

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.

In this episode of Unfiltered, Dylan Scroggins talks with Mo Hashem, Visionary of Flat Fee Landlord, about what it takes to build and scale a property management company across multiple markets.

Mo shares how Flat Fee Landlord grew from Northern Virginia into the Texas Triangle, why Texas became a key market for the company, and how people, processes, EOS, and remote leadership have helped the business manage 600+ units across two regions.

The conversation also dives into some of the biggest questions facing property management today: AI, private equity, changing market conditions, and the risk of turning property management into a commodity. Mo explains where AI is already changing the way his team operates, why some roles no longer need to be replaced, and why he believes the companies that succeed will be the ones that continue creating real value for their clients.

Links

Mo on LinkedIn - / Mo A. Hashem| 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

03:00 — Building Flat Fee Landlord

06:00 — Why Texas?

09:00 — Scaling Across Markets

11:30 — People, Processes & Remote Leadership

14:30 — The EOS Structure

16:30 — The Current Houston Market

18:11 — AI, VC/PE & the Future of PM

22:04 — AI Becoming a Commodity

25:00 — Building a Generational Business

28:00 — Lessons From 15 Years in 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 is joined by Stacey Salyer, an acquisition strategist from Bellingham, Washington, to discuss the strategies behind successful growth and acquisitions in property management. Drawing from her experience and industry insights, Stacey shares how operators can approach acquisitions more strategically and build stronger businesses through intentional growth.

They explore the role of relationships, acquisition strategy, and industry knowledge in creating opportunities for property management companies. Stacey also shares insights into what operators should consider when evaluating growth opportunities and how having the right strategy can make the difference between simply growing and building a stronger, more sustainable business.

This conversation offers practical insights for property management owners and operators looking to better understand acquisitions, identify opportunities, and approach growth with a more strategic mindset.

If you're thinking about expanding your property management business or simply want to better understand the acquisition side of the industry, this episode is worth a listen.

Links

Stacey on LinkedIn - / Stacey Salyer| 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

0:53 — Stacy's origin story in property management

1:51 — Buying 370 doors at the start of COVID

3:58 — Growing from 200 to over 500 doors overnight

7:48 — Why acquisitions are heating up right now

8:05 — AI's impact on smaller PM companies

11:17 — The hot take: 100–300 door owners may be at risk

13:20 — How Stacy teaches people to build an acquisition engine

19:55 — The biggest mental hurdle: fear of buying

26:25 — How sellers should prepare 12–24 months out

35:16 — Favorite tools, podcasts, and the future of PM

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 Stephen Glover, CEO, owner, and principal broker of Peak Property Management, to discuss why growing a property management company isn't always about adding more doors. With nearly 1,500 rental units and a 45-person team, Stephen shares how turning down more than 4,000 units helped Peak protect its service, culture, and long-term growth.

They explore how Peak built a boutique brand around selectivity, trust, and strong relationships, along with the leadership systems that keep a growing team aligned. Stephen also shares how EOS, intentional hiring, and a focus on creating better "experiences" instead of simply following processes have shaped the company's approach to tenants, owners, and vendors.

From building a strong investor community in Richmond to navigating acquisitions and developing future leaders, this conversation offers practical insights for property management owners looking to grow without sacrificing the people and culture behind the business.

Links

Stephen on LinkedIn - / Stephen Glover | 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

2:36 — His background in fitness and special operations team-building

3:25 — How he got offered a partnership and became an owner

5:37 — Turning down thousands of units to protect growth quality

6:32 — Why selective growth helped them build a strong reputation

8:38 — Building a product that everyone wants, but not everyone can have

12:45 — Brand, quality merch, and why they don't want to look cheap

21:40 — Leadership development and why building the right team was survival

31:59 — Reframing processes as "experiences" instead of just workflows

35:29 — The biggest opportunity and risk: AI in 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.