Own Your Market: Matthew Whitaker's Playbook for Property Management Growth

What Makes Property Management Different in Historic Cities | Bernard Fromherz

In this episode, Dylan Scroggins sits down with Bernard Fromherz (Owner of Upper Management Realty) in the PropertyManagement.com [http://PropertyManagement.com] van while at NARPM Broker Owner, to explore what makes property management in New Orleans unlike anywhere else. Bernard shares how managing historic properties, navigating local regulations and preparing for events like Mardi Gras and hurricane season require a unique approach to operations, maintenance, and resident experience. They also discuss the city's evolving real estate market, the impact of Hurricane Katrina on Bernard's entrepreneurial journey, and how his tech stack keeps his team efficient and adaptable while preserving the character of one of America's most historic cities. Links Bernard on LinkedIn - / [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnR4WndocDV5ZDdaeWlRZU9qS19UVFRvQ0JuZ3xBQ3Jtc0tsRExtM28zeHJtVUQtblFFQWc1UDBvZXFiU2w1aDA1SUtvMGtWQVd3QkwzWjZ5N3JqZzhmWUJhNUEzbEhwQ2hZN1c3LWV5YUR5YTRYaFBjWVRLZ3RiUmcwY1F2R08xSy16WG9Nb3puQ25mck5fdVRlNA&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fvanessaanderson%2F&v=skBdBRxZwCc] Bernard Fromherz | LinkedIn [https://www.linkedin.com/in/bernard-fromherz-5165188/] Dylan on LinkedIn - / [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbEFieXptMmRycHZraW9wS2t3MmtXU1NBMnQ3Z3xBQ3Jtc0ttQXVVUy1sU2FiUGVwU2g3SzRuYnA0Q3VSODJ4QXhrX3VhSFU0SVE1NnVQRjh6ZUo4M0tRR281YTFPVFh3WE15N3RRSmQ5Z1VSU0ZfXzRKRG5YLWZIVUdPZFJQdG1BYU9JT1NoVEhhc19HQXRNYU1GVQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fdylanscroggins%2F&v=skBdBRxZwCc] Dylan Scroggins | LinkedIn [https://www.linkedin.com/in/dylanscroggins/] PropertyManagement.com - https://propertymanagement.com/ The Kalmar Group - https://thekalmargroup.com/pm [https://thekalmargroup.com/pm] Subscribe to PropertyManagement.com [http://PropertyManagement.com]'s weekly Newsletter: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbEdmbzJvTjRRbHZndWd4ajNFdGc4ZldzX1NLZ3xBQ3Jtc0ttNVZHQjdGd21qUk5KU2NVMmNxZkZuWHk5a0tDQ3AxZFhLSkNmTmV4Q3JLbGg3cDUta3dVTjRNaUJ0WVpzODc3OU5tbS1vWTN3UlVPLUVUSlctRUR6WlhNWHBfdFVycEFVX3J5LXZubFVuUHlsSkR1RQ&q=https%3A%2F%2Fpropertymanagement-com.kit.com%2Fsubscribe-to-newsletter&v=skBdBRxZwCchttps://propertymanagement-com.kit.com/subscribe-to-newsletter Chapters 00:00 — What makes New Orleans unique for property management 00:57 — Introduction to Bernard and the episode setup 02:01 — Historic, mixed-use, and French Quarter properties 03:09 — Lease types and who rents in these neighborhoods 03:38 — Generational ownership and property turnover after major events 04:27 — Katrina's impact and Bernard's return to New Orleans 06:27 — Starting Upper Management Realty after working in development 07:40 — Growth from 30 doors to 800+ doors 08:50 — Why New Orleans is so different from other markets 09:27 — Hurricanes, swarming termites, and local disruptions 10:31 — Maintaining historic housing stock 11:42 — The future outlook for New Orleans 12:12 — Why the city feels more optimistic right now 13:26 — Growth goals and suburban expansion 15:05 — Regulatory concerns and market moats 16:27 — Technology adoption and avoiding unnecessary complexity 17:55 — Vendor overload and choosing tools carefully 18:22 — Bernard's lean tech stack 20:51 — Crawfish, local culture, and Mardi Gras stories 22:35 — How property management changes you personally 23:23 — Mardi Gras parking and parade-route challenges 25:14 — AppFolio and the most important tools in the business 26:26 — Atomic Habits and continuous improvement 27:13 — Coffee, crawfish, and closing thoughts 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.

Military Roots to Industry Leader: The Bold Vision Behind RentVine's Data-Driven Future | David Borden

In this episode Matt Speer sits down with David Borden, CEO of Rentvine for a candid conversation about the evolution of property management software, the growing importance of customer support, and why open data access is becoming a competitive advantage. David shares how his background in property management shaped Rentvine's approach to building software, listening to customers, and creating tools that actually help operators scale. They also dig into the future of AI in property management, including automation, agentic workflows, and why structured data is becoming the foundation for better decisions, better client outcomes, and faster innovation. Links David on LinkedIn - / [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnR4WndocDV5ZDdaeWlRZU9qS19UVFRvQ0JuZ3xBQ3Jtc0tsRExtM28zeHJtVUQtblFFQWc1UDBvZXFiU2w1aDA1SUtvMGtWQVd3QkwzWjZ5N3JqZzhmWUJhNUEzbEhwQ2hZN1c3LWV5YUR5YTRYaFBjWVRLZ3RiUmcwY1F2R08xSy16WG9Nb3puQ25mck5fdVRlNA&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fvanessaanderson%2F&v=skBdBRxZwCc] David Borden | LinkedIn [https://www.linkedin.com/in/david-borden-a760093/] Matt on LinkedIn - / [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbFRnb1Iyb0tTd0dhWUZ3b3FUZTNOM0xWdEt1UXxBQ3Jtc0tua2NFX0VYLWxJeTlmd2t1YkZRNkFhSXlYZy1MaGJNY3FwLVRXSFAxUkJGSnAyOFZ1d0lsS0U5ZzBHQ3RWTnRlX0JzdDdjeHZVclVBSG1uc1RkNFlmY2hwRllGT0VSRUt2VWtPNVVWOG1JQ3ZfdVJmZw&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fmspeer%2F&v=skBdBRxZwCc] Matt Speer | LinkedIn [https://www.linkedin.com/in/mspeer/] PropertyManagement.com - https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqblBDMDlQcUNVRnhRYUVWaFhHb1l6OG1QVUM4UXxBQ3Jtc0ttOEZJYWZFUDBLM295QWg3X2VsMXd0MXZuRF9GdXVhQ3B3S2hYTVJNQUV5TFMwaExWSURFaDNnWDRNRHhBa3Bsb0NFSU5kSHZ6YW12RXgzcllSby1EcVdwZThLa3dRSzFtbXhZN3NncjNfa1hkU3Z4Zw&q=https%3A%2F%2Fpropertymanagement.com%2F&v=skBdBRxZwCc https://propertymanagement.com/ [https://propertymanagement.com/] Subscribe to PropertyManagement.com's weekly Newsletter: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbEdmbzJvTjRRbHZndWd4ajNFdGc4ZldzX1NLZ3xBQ3Jtc0ttNVZHQjdGd21qUk5KU2NVMmNxZkZuWHk5a0tDQ3AxZFhLSkNmTmV4Q3JLbGg3cDUta3dVTjRNaUJ0WVpzODc3OU5tbS1vWTN3UlVPLUVUSlctRUR6WlhNWHBfdFVycEFVX3J5LXZubFVuUHlsSkR1RQ&q=https%3A%2F%2Fpropertymanagement-com.kit.com%2Fsubscribe-to-newsletter&v=skBdBRxZwCchttps://propertymanagement-com.kit.com/subscribe-to-newsletter [https://propertymanagement-com.kit.com/subscribe-to-newsletter] Chapters 00:00 - Introduction: RentVine's update and industry context 02:07 - The significance of property manager websites and historical growth 03:58 - David Borden's journey and founding RentVine 05:20 - Roots in property management from family background 06:14 - Early ventures: RentClicks and property management advertising 08:02 - Transition into software development and customer feedback 09:25 - Supporting property managers through support and innovation 10:53 - The state of rent management today and customer feedback 12:20 - How RentVine's support team builds trust and expertise 13:39 - The importance of access to detailed data and APIs 14:05 - The philosophy behind open API and AI deployment 15:01 - The industry's misconception about data access and control 16:25 - AI evolution and RentVine's AI strategies 17:25 - The challenges of complex property management data 18:23 - Creating trust and surfacing property manager success stories 19:19 - The industry's movement towards open data and AI-powered insights 20:16 - Usability and interface improvements to serve large portfolios 21:38 - The role of private equity and collaboration with investors 23:04 - Goals: Growth, innovation, and serving customer needs 25:31 - Future vision: Going public vs. industry leadership 28:24 - The role of private equity in scaling property management tech 29:21 - The agentic future: AI automation and innovation with structured data 31:36 - AI-powered maintenance and tenant support agents 33:04 - Commitment to value, support, and customer-centric innovation 36:29 - Personal favorites: Wine, books, and learning with AI 37:28 - The historical parallels of AI disruption in tech industries 38:27 - When generative AI first became a game changer 39:48 - Challenges: hallucinations, errors, and responsible AI use 40:45 - The distinction between automation and agentic AI 42:14 - The long path toward fully autonomous AI (mid-2030s estimate) 43:36 - Personal tools: Grok for learning and wine evaluation 45:41 - Education, deep learning, and applying AI insights in daily life 47:20 - One word to describe the future of property management: Valuable 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.

The Leasing Advantage: Why Speed Wins in Property Management | ShowMojo

In this episode, Matt Speer interviews Vanessa Anderson and John Squires from ShowMojo to explore the future of property leasing technology, data-driven decision making, and how AI is transforming property management. They discuss ShowMojo's innovative solutions, industry trends, and strategies to reduce vacancies and improve leasing outcomes. Links Vanessa on LinkedIn - https://www.linkedin.com/in/vanessaanderson/ [https://www.linkedin.com/in/vanessaanderson/] John on LinkedIn - https://www.linkedin.com/in/john-squires-03a23a287/ [https://www.linkedin.com/in/john-squires-03a23a287/] Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/ [https://www.linkedin.com/in/dylanscroggins/] Matt on LinkedIn - https://www.linkedin.com/in/mspeer/ [https://www.linkedin.com/in/mspeer/] PropertyManagement.com - https://propertymanagement.com/ [https://propertymanagement.com/] The Kalmar Group - https://thekalmargroup.com/pm [https://thekalmargroup.com/pm] Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter [https://propertymanagement-com.kit.com/subscribe-to-newsletter] Chapters 00:00 Introduction to ShowMojo and Guests 00:34 Guest backgrounds and company history 02:54 Overview of ShowMojo's mission and evolution 04:09 The importance of modern leasing technology 04:53 From automation to agentic leasing workflows 06:48 How ShowMojo personalizes the leasing experience 09:12 Response time and lead conversion rates 10:21 Data-backed insights and industry benchmarks 13:21 ShowMojo's future focus: vacancy reduction 14:49 The Property Management Vendor Performance Index 16:07 Customer support, credibility, and company longevity 19:02 AI integration and future product development 25:18 Balancing efficiency, legal considerations, and customization 27:50 The role of data accessibility and owner reporting 32:21 ShowMojo's commitment to industry leadership 33:15 Closing thoughts and industry outlook 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.

Own Your Market: Matthew Whitaker's Playbook for Property Management Growth

In this episode, Matt Speer interviews Matthew Whitaker, Founder and CEO of Evernest, exploring the growth of property management, the role of acquisitions, and the impact of AI on the industry. They share insights on scaling strategies, technology adoption, and leadership development. Links Matthew on LinkedIn - https://www.linkedin.com/in/matthewwhitaker/ [https://www.linkedin.com/in/matthewwhitaker/] Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/ [https://www.linkedin.com/in/dylanscroggins/] Matt on LinkedIn - https://www.linkedin.com/in/mspeer/ [https://www.linkedin.com/in/mspeer/] PropertyManagement.com - https://propertymanagement.com/ [https://propertymanagement.com/] The Kalmar Group - https://thekalmargroup.com/pm [https://thekalmargroup.com/pm] Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter [https://propertymanagement-com.kit.com/subscribe-to-newsletter] Chapters 00:00 Introduction to Evernest and Its Journey 02:50 The Growth Strategy: Acquisitions and Organic Growth 07:19 Navigating Acquisitions: Key Considerations 11:08 AI in Property Management: Current Trends and Future Potential 14:03 Creating an AI Culture: Balancing Innovation and Practicality 19:52 Reflections on the Evolution of Property Management 21:40 The Challenges of Property Management: A Personal Perspective 26:15 Leadership and Continuous Learning 30:34 The Future of Property Management: Barbell Strategy 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.

The Maintenance Revolution in Property Management: AI, Vendors, and Operations | Nitin Gupta

In this insightful interview, Nitin Gupta from Mason shares how AI is transforming property management, focusing on maintenance automation, data integration, and future trends. Discover how Mason's innovative approach helps property managers improve efficiency, tenant satisfaction, and operational insights. Links Nitin on LinkedIn - https://www.linkedin.com/in/nitguptaa/ [https://www.linkedin.com/in/nitguptaa/] Dylan on LinkedIn - https://www.linkedin.com/in/dylanscroggins/ [https://www.linkedin.com/in/dylanscroggins/] Matt on LinkedIn - https://www.linkedin.com/in/mspeer/ [https://www.linkedin.com/in/mspeer/] PropertyManagement.com - https://propertymanagement.com/ [https://propertymanagement.com/] The Kalmar Group - https://thekalmargroup.com/pm [https://thekalmargroup.com/pm] Subscribe to PropertyManagement.com's weekly Newsletter: https://propertymanagement-com.kit.com/subscribe-to-newsletter [https://propertymanagement-com.kit.com/subscribe-to-newsletter] Chapters 00:00 Introduction to the Conversation 01:33 Exploring Mason and Its Culture 06:05 Nitin's Journey into Property Management 11:03 Understanding Mason's AI System 16:07 Data Integration and Context in Maintenance 20:36 The Future of SaaS and AI in Property Management 25:20 Transparency and Performance Metrics 29:49 The Impact of AI on Employment in Property Management 34:25 Final Thoughts and 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.