In this episode of Unfiltered, co-hosts Dylan Scroggins and Matt Speer sit down with Matt Nelson for a wide ranging conversation on what it takes to build trust, scale thoughtfully, and operate with discipline in modern property management. Matt shares lessons from growing up in a family-run property management business, navigating rapid portfolio growth and contraction, and refocusing on client alignment through performance based fees. The discussion also explores how surveys, technology, and emerging AI driven search are reshaping how operators communicate value and stay competitive in a changing regulatory environment.

They discuss: • Building a performance based property management model aligned with owner interests • Lessons from scaling to thousands of doors and refocusing on a core market • Using surveys and client feedback to improve operations and trust • The role of workflows, KPIs, and technology in creating efficiency • How AI search and content strategy are changing visibility for property managers

Links:

Matt Nelson on LinkedIn - https://www.linkedin.com/in/matt-nelson-2962497a/

Excalibur Homes - https://www.excaliburhomes.com/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt Speer on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:02:21) - Matt Nelson's journey in property management (00:03:42) - Growth and expansion strategies (00:08:39) - The importance of surveys and client feedback (00:12:10) - Challenges and solutions in maintenance (00:14:46) - Leveraging technology and AI (00:19:53) - Building trust and transparency (00:20:23) - Future of property management (00:21:45) - Navigating government regulations (00:23:12) - Leveraging AI for visibility (00:23:37) - The importance of quality content (00:28:41) - Personal reflections and leadership (00:29:58) - Wrestling and life lessons (00:33:34) - Lightning round and final thoughts

In this episode of Unfiltered, Matt Speer and Dylan Scroggins sit down with Ed Riggenbach to unpack the realities of building and sustaining a property management business in a challenging Midwest market. Ed shares his journey from accidentally entering the industry to navigating mergers, partnerships, and long term plateaus at scale. The conversation explores the tradeoffs between growth and profitability, the emotional weight carried by operators, and the leadership shifts required as teams and families grow. Throughout the discussion, Ed offers candid reflections on patience, decision making, and what it really takes to professionalize a business over time.

They discuss: • Ed's path into property management and the early mistakes that shaped his leadership style • The decision to merge with a competitor and how that partnership unlocked scale and stability • Why staying at roughly 500 doors can be more intentional than chasing growth for its own sake • Managing people, emotions, and expectations in an increasingly intense operating environment • Balancing automation, AI, and process with the need for human connection and judgment

Links:

Ed on LinkedIn - https://www.linkedin.com/in/ed-riggenbach-04372441/

Welcome Home Milwaukee - https://whmilwaukee.com/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:02:14) - Ed's property management journey (00:05:07) - Early challenges and lessons learned (00:06:42) - Scaling up and merging companies (00:13:29) - Involving family in business (00:16:39) - Industry trends and emotional dynamics (00:21:29) - Embracing expertise in property management (00:23:46) - Navigating industry changes and growth (00:26:11) - Challenges in maintenance and operations (00:27:46) - Preparing for a transformative 2026 (00:30:46) - The role of AI in property management (00:34:00) - Personal reflections and future plans

In this episode of Unfiltered, co-hosts Dylan Scroggins and Matt Speer break down the launch of the PropertyManagement.com Top 100 and the broader vision behind building a trusted, data-driven standard for the property management industry. They unpack why the Top 100 exists, how companies are evaluated, and what differentiates earned reputation from pay to play rankings. The conversation also explores the early momentum behind the platform, lessons learned from survey data, and how transparency and trust are reshaping how property management businesses compete.

They discuss:

• Why the PropertyManagement.com Top 100 was created and what problem it aims to solve
• How the four core scoring categories are built around owner priorities
• The role of verified owner surveys and why communication consistently outperforms cost concerns
• Why the platform avoids pay to play models and how free and paid tiers actually differ
• What property managers should do next, whether they are already ranked or just getting started

Topics:

(00:00:00) - Intro (00:01:22) - The story behind Property Management.com (00:04:03) - Building the top 100 list (00:06:19) - Verification and rankings explained (00:11:38) - Surveys and feedback (00:23:21) - Future plans and accountability (00:27:12) - Closing thoughts and call to action

Links:

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Dylan Scroggins and Matt Speer sit down with John-Michael Elliott for a wide-ranging conversation on building and scaling a property management business through market cycles, reputation, and disciplined operations. John-Michael shares how his firm was born out of the mid-2000s housing downturn and grew by focusing on asset management rather than short-term cash flow. The discussion explores the realities of working with accidental investors, navigating fast-growing Florida markets, and raising the professional standard of the property management industry based on real-world experience.

They discuss: • How John-Michael entered property management during the short sale era and built a business out of necessity • The importance of asset management, documentation, and inspections in protecting owners and operators • Managing growth in a rapidly expanding Florida market and adapting to market corrections • Educating accidental investors on long-term wealth, equity growth, and realistic expectations • Using technology and AI to improve maintenance coordination, communication, and operational efficiency

Links:

Elliott and Eijo Real Estate Group -https://mylakelandhome.com/

John-Michael Elliott on LinkedIn - https://www.linkedin.com/in/john-michael-elliott-9114655/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:01:37) - John-Michael's journey into property management (00:04:08) - Current market and door count (00:04:59) - Challenges and opportunities in a booming market (00:10:03) - Professionalizing property management (00:16:29) - Lessons learned and future goals (00:21:30) - Riding the real estate wave (00:22:36) - The role of AI in property management (00:25:08) - Building and maintaining reputation (00:30:39) - Challenges and changes in property management (00:34:23) - Lightning round: insights and tools

Jim Miller joins co-hosts Dylan Scroggins and Matt Speer for a candid conversation about the realities of operating a property management company, navigating growth, and confronting the challenges that come with scaling. Jim reflects on his unconventional path into the industry, the lessons learned through financial setbacks, and how personal motivations have shaped his approach to leadership. The group explores the operational shifts Jim is making, including a major transition to HubSpot and Rentvine, and how greater visibility into workflows is transforming his team's performance. They also touch on mindset, the importance of embracing difficult seasons, and why transparency will define the next era of property management.

They discuss: • Jim's path from real estate investing to property management and the early struggles that shaped his philosophy • How his "why" influences decision making, resilience, and long term perspective • Lessons learned from declining door count and why improving core operations matters more than chasing scale • The transition to Rentvine and Hubspot, and how better data visibility is reshaping performance • Why transparency, accountability, and third-party validation will drive the future of property management

This episode offers clear, grounded insights for operators seeking practical guidance, renewed focus, and a more transparent path forward.

Links:

Jim on LinkedIn - https://www.linkedin.com/in/perfassetmgmt/

Performance Asset Management - https://www.pammke.com/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:01:43) - College football and Wisconsin's prospects (00:05:52) - Jim Miller's journey into property management (00:10:37) - Challenges and growth in property management (00:17:15) - Technology updates and system improvements (00:20:57) - Leveraging Hubspot for operational efficiency (00:23:34) - Challenges and considerations in CRM transition (00:26:55) - Choosing the right CRM (00:29:25) - Cost breakdown and financial benefits (00:33:22) - Scaling with Hubspot: a case study (00:34:26) - Lightning round: tools, books, and podcasts (00:38:41) - The future of property management

Dylan Scroggins welcomes Chuck Hattemer for a deep dive into what it takes to scale a modern property management company. Chuck walks through lessons from building Poplar Homes from zero to fifteen thousand doors, including the realities of early-stage operations, the evolution of processes at each growth tier, and how clarity around brand and customer experience becomes a differentiator long before most operators realize it. He also shares insights on technology, data, and AI that are shaping the next era of property management, along with the role of transparency and trust as the industry continues to mature.

They discuss:

• How Chuck defines the key growth stages from zero to fifteen thousand doors • Why brand matters as early as the first one hundred to five hundred units • The shift toward data, prediction, and personalization in modern property management • How AI search and verified information are changing sales and marketing • The importance of strong referral networks and lifecycle-based lead generation

Links:

Chuck on Linkedin - https://www.linkedin.com/in/charleshattemer/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:00:37) - Chuck's background and career (00:04:11) - Stages of growth in property management (00:10:21) - The importance of brand in property management (00:16:33) - Future trends: technology and AI in property management (00:25:44) - PropertyManagement.com: building trust and transparency (00:34:30) - Lightning round: tools, books, and industry insights

Spencer Sutton joins co-hosts Dylan Scroggins and Matt Speer to discuss the long game of content marketing and the personal evolution required to stay in the Property Management industry. Spencer breaks down the mindset and systems behind effective marketing, referrals, and relationship building, offering practical guidance for operators navigating today's challenging lead environment. Throughout the episode, Spencer shares candid insights on grit, leadership, and the discipline needed to grow both a company and a career in property management.

They discuss: • How Spencer entered property management and joined the early Golden Key team • Why long term content and brand building became Evernest's competitive advantage • The evolution of lead generation and why realtor referrals matter more than ever • How PM owners should think about marketing, churn, and the shifting investor landscape • The personal lessons Spencer has learned from a decade of growing in a demanding industry

Links:

Evernest - https://www.evernest.co/

Spencer on LinkedIn - https://www.linkedin.com/in/spsutton/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:02:00) - Spencer's career and background (00:03:04) - Joining Evernest and marketing insights (00:07:36) - Challenges and growth strategies (00:11:14) - Content and marketing philosophy (00:16:03) - Realtor referrals and lead generation (00:26:48) - The challenge of marketing in property management (00:28:31) - Exciting opportunities in property management (00:31:25) - The human element in property management (00:38:41) - Favorite tools and resources (00:45:07) - The future of property management

In this episode of Unfiltered, host Dylan Scroggins sits down with Evan Howard, Principal National Account Executive at Second Nature, to discuss the evolving landscape of property management. Evan shares his journey from selling Cutco knives to helping drive growth at Second Nature, where he focuses on strategic partnerships and improving the resident experience. He reflects on the company's "triple win" philosophy—creating value for residents, operators, and investors—and offers perspective on how culture, empathy, and alignment of incentives are shaping the next generation of property management.

They discuss:

• Building systems that balance empathy and efficiency in property management
• The evolution of Second Nature from air filter delivery to a resident experience platform
• Lessons learned from early sales experience and developing resilience in business
• The importance of culture, relationships, and community in scaling a company
• How AI, automation, and improved resident experiences are transforming the industry

Links:

Second Nature - https://www.secondnature.com/

Evan on LinkedIn - https://www.linkedin.com/in/evanprothrohoward/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:00:57) - Introducing Evan (00:02:15) - Evan's journey: From Cutco to Second Nature (00:02:45) - The triple win approach of Second Nature (00:03:56) - Building relationships in property management (00:11:16) - The future of property management: AI and automation (00:18:23) - Quick fire questions and closing remarks

In this episode of Unfiltered, Dylan Scroggins and Matt Speer sit down with Adam Willis of Nestwell to unpack his unique path from sandwich delivery driver and professional Yu-Gi-Oh! duelist to leading one of Utah's top property management companies. Adam shares how growing up in a family business shaped his entrepreneurial instincts, what pushed him to scale from 85 to over 1,100 doors, and the mindset shift that turned his company from a "lifestyle business" into a high-performing, data-driven organization. He opens up about leadership, culture, and the systems, like EOS and ProfitCoach, that helped his team evolve and thrive.

They discuss: • The unlikely connection between Yu-Gi-Oh! tournaments and business strategy • How saying no to a merger created a stronger culture and buy-in within his team • Using EOS to drive intentional, data-backed growth across 1,100+ doors • Building a leadership team that challenges you and aligns with mission and values • Why omnichannel communication and resident experience are the next frontiers in property management

Links:

Nestwell Property Management - https://www.nestwellpropertymanagement.com/

Adam on LinkedIn - https://www.linkedin.com/in/adam-willis-12b44a25b/

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:01:37) - Life in Salt Lake City (00:02:48) - Adam Willis' entrepreneurial journey (00:03:28) - The Yu-Gi-Oh marketing experience (00:06:48) - Joining the family business (00:10:09) - Scaling the business (00:12:30) - The role of EOS and Profit Coach (00:14:01) - Challenges and strategies in growth (00:22:52) - Building a strong leadership team (00:25:41) - Building a global team (00:27:18) - Industry insights and exciting trends (00:28:34) - The importance of omnichannel communication (00:32:22) - Mastering Google reviews (00:40:02) - Balancing team capacity and customer service (00:44:32) - Final thoughts and future outlook

In this episode of Unfiltered, Dylan Scroggins and Matt Speer sit down with Chicago-based entrepreneur and property management leader Mark Ainley for a wide-ranging conversation on growth, marketing, and the evolving real estate landscape. Mark shares how his early experiences in investing and property management shaped the foundation of GC Realty, discusses how he's built a business that thrives in both residential and commercial markets, and explains why reputation and responsiveness remain his company's most powerful differentiators. He also offers a candid look at how technology, regulation, and industry maturity are reshaping the property management space.

We discuss:

• The evolution of GC Realty from a small brokerage to a major property management firm
• How reputation, responsiveness, and reviews drive long-term growth
• The challenges and opportunities of scaling a management company past key "growth ceilings"
• Why regulation can ultimately strengthen the property management industry
• How AI and new tools are transforming operations and marketing strategies

Links:

Mark on LinkedIn - https://www.linkedin.com/in/mark-ainley/

GC Realty and Development - https://www.gcrealtyinc.com/

Prompt Cowboy - https://www.promptcowboy.ai/

Hook Point — https://hookpoint.com/hook-point-book/

Pitch Anything — https://www.amazon.com/dp/0071752854

Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/

Matt on LinkedIn - https://www.linkedin.com/in/mspeer/

PropertyManagement.com - https://propertymanagement.com/

The Kalmar Group - https://thekalmargroup.com/

Topics:

(00:00:00) - Intro (00:01:50) - Life as a Bears fan (00:03:10) - Mark Ainley's journey into property management (00:05:45) - Challenges and growth in property management (00:08:45) - Industry insights and future concerns (00:14:39) - Marketing and content creation (00:17:49) - Real estate investing and media ventures (00:19:32) - Emerging technologies and tools for business success (00:20:08) - The importance of reputation management (00:21:50) - Balancing real and online reputations (00:25:27) - Effective tools and apps for business (00:27:48) - AI and its role in business operations (00:29:11) - Recommended books and podcasts for PM leaders (00:33:50) - The future of property management