Matthew Whitaker is back! And a lot’s changed since his first appearance.

We discuss:

• (00:01:38) - Introducing season six
• (00:02:44) - Matt’s background and career
• (00:07:04) - Dealing with owners
• (00:20:47) - Sponsor - RentEngine
• (00:22:41) - Evernest’s tech stack
• (00:28:03) - Transitioning away from eos
• (00:33:35) - Dealing with management layer issues
• (00:40:31) - Sponsor - Crane
• (00:42:35) - Categories of owners
• (00:44:05) - Multifamily experiences
• (00:52:38) - The state of Evernest’s acquisition appetite
• (01:02:38) - Leadflow realities
• (01:06:57) - The state of the industry
• (01:09:41) - Get in touch with Matthew

Learn more & connect with me here:

• ⁠Crane⁠, the private community for property management business owners.
• ⁠My Free PM Newsletter⁠
• ⁠RL Property Management⁠

Learn more and connect with Matthew here:

• Evernest
• Matthew on LinkedIn
• The Evernest Property Management Show Podcast on Apple

Today, Evernest manages nearly 20,000 doors across 50+ markets. We dig into how they’re structured, what they’ve learned from buying 17 PM companies in six months (!), and why the “property manager” job title is making a comeback.

Matthew breaks down their tech stack, AI experiments, and how they think about scaling operations without sacrificing owner experience. We also talk about churn (especially from mid-sized investors), how valuation multiples have shifted, and what he wishes more property managers understood about communication vs. execution.

If you’re rethinking org charts, prepping to sell, or just trying to reduce chaos, this one’s worth your time.

In this episode, Jennifer Stoops shares how she scaled a PM company to 3,600+ doors before transitioning into her current role as SVP of Industry Relations at PetScreening.

We dig into that journey - from building systems and PM pod structures at scale to managing an office with 30 dogs (yes, really).

Jennifer explains what most PMs get wrong about pet policies, how unreported pets erode NOI, and why PetScreening has become the “Carfax for pets.” We also cover M&A pitfalls, vendor risk, breed restrictions, and why the portfolio model often breaks past a certain door count.

We discuss:

• (00:02:04) - Jennifer’s background and career
• (00:11:35) - Incident tracking
• (00:14:59) - Breed restrictions in insurance policies
• (00:16:51) - Sponsor - ⁠Crane⁠
• (00:19:04) - Discrimination by weight and breed
• (00:20:32) - Americans spending more on pets than kids
• (00:22:19) - Jennifer’s time at Park Avenue Properties
• (00:23:47) - How to organize a larger PM company
• (00:34:11) - Sponsor -⁠ RentEngine⁠
• (00:36:04) - Multi-market operations
• (00:50:00) - Advice to PM owners considering selling
• (00:53:59) - Non-obvious things to improve sales prospects
• (00:58:24) - Advice for considerations to take seriously in 2025 if you’re looking to acquire other companies
• (01:01:05) - How to approach an owner when you want to acquire them
• (01:07:26) - Getting in touch with Jennifer

Learn more & connect with me here:

• ⁠Crane⁠, the private community for property management business owners.
• ⁠My Free PM Newsletter⁠
• ⁠RL Property Management⁠ 

Learn more and connect with Jennifer here: 

• Jennifer on LinkedIn
• PetScreening

Monica Gilroy is the founder of the Gilroy Law Firm and a legal powerhouse in the property management space.

In this episode, she shares what to do if ICE shows up, how to bulletproof your application process, and why short leases are fine (if your systems are solid). We also dive into lawsuits, insurance gaps, and why you can say no to Section 8 in some markets (if you do it right).

If you’ve ever felt legally exposed running your PM biz, this episode brings clarity - and a few fun “ask me how I know” moments.

Chapters:

• (00:00:00) - Intro
• (00:01:56) - Monica’s background and career
• (00:04:09) - How PMs can handle ICE enforcement
• (00:08:09) - Approving renters
• (00:14:19) - Emotional Support Animals
• (00:16:00) - Sponsor - CallRail
• (00:17:18) - Appealing PM laws
• (00:23:33) - Waiving late fees
• (00:25:32) - Insurance
• (00:32:32) - Sponsor - RentEngine
• (00:34:26) - Putting a non-disparagement clause in a lease
• (00:43:02) - ADA Website lawsuits
• (00:48:38) - Section 8 nuances
• (00:54:31) - What are property managers afraid of that they shouldn’t be, and what are they not thinking about that should worry them?
• (01:00:41) - Getting in touch with Monica

Learn more & connect with me here:

• ⁠Crane⁠, the private community for property management business owners.
• ⁠My Free PM Newsletter⁠
• ⁠RL Property Management⁠ 

Learn more and connect with Monica here: 

• The Gilroy Firm
• Monica on LinkedIn

In this episode, I sat down with Lisa Horner, Chief Marketing Officer at AppFolio - LIVE at the AppFolio FUTURE Conference. We talked about what’s actually working in property management marketing today, digging into AI hype vs. real impact, why understanding your customer beats clever tactics, and how to market without sounding like… well, a marketer.

Lisa shares how AppFolio stays close to operators (literally - engineers on the tradeshow floor), why branding starts with asking “who are we?” and “what do we care about?”, and how the best marketing campaigns begin with deep empathy and strategic constraints.

We also touch on leadership transitions, the role of experimentation, and how business owners can prepare for AI-powered change (without panicking).

We discuss:

• (00:00:00) - Intro
• (00:01:44) - AI in Property Management
• (00:06:03) - Marketing Strategies in the AI Era
• (00:09:17) - Understanding Customer Needs
• (00:16:31) - Sponsor - PropertyManagement.com
• (00:20:53) - Leadership and Management Insights
• (00:30:41) - Reflecting on Personal Beliefs and Values
• (00:30:53) - The Fear of Defining Your Brand
• (00:31:33) - Strategic Planning and Constraints
• (00:32:16) - The Importance of Targeted Marketing
• (00:33:00) - Sponsor - RentEngine
• (00:34:54) - The Impact of AI on SEO and Digital Marketing
• (00:37:47) - Embracing Experimentation in Marketing
• (00:40:23) - Understanding Your Customer Base
• (00:46:45) - Balancing Inbound and Outbound Marketing
• (00:49:15) - Leveraging Technology for Business Growth
• (00:55:34) - The Role of Marketing Beyond Lead Generation
• (00:57:21) - Conclusion and Final Thoughts

Learn more and connect with Lisa here: 

• Lisa on LinkedIn
• AppFolio

Learn more & connect with me here:

• ⁠⁠⁠Crane⁠⁠⁠, the private community for property management business owners.
• ⁠⁠⁠My Free PM Newsletter⁠⁠⁠
• ⁠⁠⁠RL Property Management⁠⁠⁠ 

In this episode, I’m joined by Jordan Coleman, loan officer at Live Oak Bank - one of the few banks that truly understands property management.

We break down how SBA loans can unlock 100% financing for acquisitions, the hidden pitfalls in seller notes, and what lenders really look for in both buyers and sellers. Jordan also shares practical tips for navigating SBA terms, structuring clawbacks, and avoiding red flags (like client concentration risk).

We even cover how to refinance a seller note and why time kills deals more often than you think. If you’re considering buying, selling, or just want to understand your options, this episode is packed with insight.

Timecodes:

• (00:00:00) - Intro
• (00:01:39) - Meet Jordan Coleman from Live Oak Bank
• (00:01:53) - Understanding Live Oak Bank's unique offerings
• (00:02:15) - Jordan Coleman's background and role
• (00:03:21) - Live Oak Bank's industry focus
• (00:04:45) - Live Oak Bank's property management focus
• (00:05:55) - Importance of SBA loans and preferred lenders
• (00:07:22) - Qualifying for an SBA loan
• (00:08:47) - Live Oak Bank's loan products for property management
• (00:11:05) - Analyzing buyers and sellers for acquisitions
• (00:18:37) - Sponsor: PropertyManagement.com
• (00:20:31) - Loan terms, interest rates, and closing process
• (00:28:44) - Understanding SBA loan trade-offs
• (00:29:23) - Pros and cons of SBA loans
• (00:31:38) - Importance of clawback clauses
• (00:34:13) - Sponsor: AppFolio
• (00:35:50) - Navigating SBA lenders
• (00:38:57) - Pre-qualified buyers and sellers
• (00:46:23) - Refinancing seller notes
• (00:48:38) - Horror stories and lessons learned
• (00:53:44) - Building relationships with lenders
• (00:54:53) - Conclusion and final thoughts

Learn more and connect with Jordan here: 

• Jordan on LinkedIn
• Live Oak Bank

Learn more & connect with me here:

• ⁠⁠⁠Crane⁠⁠⁠, the private community for property management business owners.
• ⁠⁠⁠My Free PM Newsletter⁠⁠⁠
• ⁠⁠⁠RL Property Management⁠⁠⁠ 

In this episode of Peter Lohmann’s Podcast, I’m joined by Allison DiSarro, SVP of Property Management Banking at Enterprise Bank & Trust. We break down what every property manager really needs to know about trust accounts, FDIC protection, and compliance risks (yes, even if your state auditor says you’re fine).

Allison explains why most banks get this wrong, how “analysis banking” works (and why it’s not interest), and the real risk of having your accounts frozen due to liens or garnishments.

We also dig into how Enterprise structures its earnings credit program, why longevity matters more than flashy rates, and what to ask your bank to protect client funds.

Chapters:

• (00:00:00) - Intro
• (00:02:20) - Alison's journey into property management banking
• (00:03:42) - The importance of sticky deposits in banking
• (00:07:19) - Federal compliance in trust accounts
• (00:08:14) - Challenges with state regulations and banking expansion
• (00:10:08) - Why Enterprise Bank stands out in property management
• (00:11:49) - Earnings credits and analysis banking explained
• (00:16:50) - Sponsor - Second Nature
• (00:18:21) - Setting earnings rates
• (00:30:06) - Sponsor - Rentvine
• (00:31:28) - Navigating state compliance and interest regulations
• (00:35:17) - Understanding client trust accounts
• (00:36:32) - Federal compliance and bank account structure
• (00:37:23) - Key questions to ask your bank
• (00:39:37) - Impact of governing entity liens and lawsuits
• (00:41:09) - Challenges with bank compliance and account management
• (00:45:25) - Recent changes in banking regulations
• (00:46:32) - Finding the right bank for property management
• (00:54:00) - Integrating technology with banking
• (01:03:31) - AI's impact on banking and fraud
• (01:06:15) - Conclusion and contact information

Learn more and connect with Allison:

• Enterprise Bank & Trust (PM Division)
• Allison on LinkedIn

Learn more & connect with me here:

• ⁠⁠Crane⁠⁠, the private community for property management business owners.
• ⁠⁠My Free PM Newsletter⁠⁠
• ⁠⁠RL Property Management⁠⁠ 

In this episode of Peter Lohmann’s Podcast, I’m joined by Janine Steiner Jovanovic, CEO of LeaseLock - a company rethinking how the multifamily industry handles security deposits, risk, and renter experience.

Janine shares how LeaseLock replaces traditional deposits with true lease insurance, protecting property owners and improving affordability for renters.

We also talk about leadership, data, and what it means to build renter-first products in a profit-driven world.

If you care about PropTech innovation, risk analytics, or the next wave of AI in property management, this one’s a must-listen.

Jump to a topic:

• (00:01:47) - Janine's background in property management
• (00:03:21) - The evolution of technology in property management
• (00:05:33) - Challenges with security deposits
• (00:08:53) - How LeaseLock works
• (00:15:48) - Sponsor - Utility Profit
• (00:17:12) - Janine's early career and innovations
• (00:19:53) - Current trends and data insights
• (00:27:34) - Ledger-based information and property focus
• (00:27:47) - Empowering renters to screen themselves
• (00:29:15) - Zillow's influence in the rental market
• (00:31:01) - Renter-first approach and product design
• (00:32:51) - Sponsor - Second Nature
• (00:35:09) - Economic health and long-term strategy
• (00:37:14) - LeaseLock's insurance model and partnerships
• (00:42:54) - PropTech landscape and funding challenges
• (00:50:56) - AI integration in property management
• (00:52:29) - Conclusion and contact information

Learn more and connect with Janine here: 

• Janine on LinkedIn - ⁠https://www.linkedin.com/in/janine-steiner-jovanovic/⁠
• LeaseLock - ⁠https://leaselock.com/⁠

Learn more & connect with me here:

• ⁠Crane⁠, the private community for property management business owners.
• ⁠My Free PM Newsletter⁠
• ⁠RL Property Management⁠ 

In this episode of Peter Lohmann’s Podcast, I’m joined by Gail Phillips, the retiring CEO of NARPM (National Association of Residential Property Managers), after more than 20 years of leadership.

We dig into how NARPM evolved from a few hundred members to the national force it is today - from the early “mom-and-pop” days and paper rent checks to COVID-era virtual everything.

Gail shares the real story behind NARPM’s antitrust saga, how fee models and tech reshaped the industry, and what she’s learned about leadership, delegation, and culture after decades in the trenches.

We also talk about why some local chapters thrive while others struggle, what the “haters” get wrong about NARPM, and her advice for the next generation of association leaders.

If you’re a property management operator or NARPM member, this episode is a must-listen.

• (00:00:00) - Intro
• (00:03:07) - Gail’s background and career
• (00:08:17) - The early day’s of NARPM conferences and the industry as a whole
• (00:16:30) - The state of conferences in the early days
• (00:18:23) - Sponsor - PropertyManagerWebsites.com
• (00:20:00) - Late 2000’s concerns and focuses
• (00:22:02) - How NARPM has evolved
• (00:27:47) - Success and Failure amongst different NARPM chapters
• (00:29:38) - Behaviors of great NARPM leaders
• (00:31:56) - Sponsor - SecondNature.com
• (00:33:27) - The state of the industry in 2025
• (00:36:01) - Antitrust philosophies
• (00:41:15) - FTC guidance for Trade Groups
• (00:47:53) - Effective membership drives
• (00:53:41) - What the haters get right about NARPM
• (00:59:14) - Thoughts for the incoming NARPM CEO
• (01:01:05) - Gail’s future

Learn more and connect with Gail here: 

• Gail on LinkedIn - https://www.linkedin.com/in/gailphillips/
• Organization Management Group - https://www.managegroup.com/
• NARPM - https://www.narpm.org/

Learn more & connect with me here:

• ⁠Crane⁠, the private community for property management business owners.
• ⁠My Free PM Newsletter⁠
• ⁠RL Property Management⁠

In this episode of Peter Lohmann’s Podcast, I’m joined by DD Lee, former owner of Skyline Property Management, now Industry Liaison at PURE and President-Elect of NARPM National.

DD shares her path from managing 12 personal rentals to running a 500-door PM company with a 3,000-door HOA division, and what it was really like to sell that business to PURE. We get into the emotional side of selling (“detach” became her mantra), how HOA management differs from single-family, and what she’s focused on now as NARPM transitions into its “2.0” era.

If you’ve ever thought about selling your management company, navigating NARPM leadership, or just trying to scale without burning out, DD’s story will hit home.

Chatpers:

• (00:00:00) - Intro
• (00:01:39) - DD’s career and background
• (00:03:59) - Challenges and differences in property management
• (00:07:40) - HOA management
• (00:10:10) - NARPM involvement and designations
• (00:12:57) - Sponsor - PropertyManagement.com
• (00:14:53) - NARPM leadership and election process
• (00:17:18) - NARPM 2.0 and organizational changes
• (00:25:32) - Comparing small business to NARPM
• (00:30:50) - Continuing education and licensing challenges
• (00:32:14) - Sponsor - Rentvine
• (00:33:35) - The emotional journey of selling a property management company
• (00:38:26) - Detachment and transitioning after the sale
• (00:42:23) - Advice for selling your property management business
• (00:45:40) - Finding purpose post-sale
• (00:48:43) - Working with Pure and future plans
• (01:00:00) - Conclusion and final thoughts

Learn more and connect with DD here: 

• PURE Property Management - ⁠https://www.purepm.co/⁠
• DD on LinkedIn - ⁠https://www.linkedin.com/in/ddlee-purepm/⁠

Learn more & connect with me here:

• ⁠Crane⁠, the private community for property management business owners.
• ⁠My Free PM Newsletter⁠
• ⁠RL Property Management⁠ 

PropertyManagement.com’s “Top 100” list is coming!

Apply before 11/30/2025 to get verified, build credibility, and win your market: https://propertymanagement.com/verification

In this episode of Peter Lohmann’s Podcast, I sit down with Matt Speer of PropertyManagement.com (yes, greatest domain ever) to unpack their “TrueMatch” score, or what Matt calls the “Carfax of property management.”

We talk about why credibility is the new currency, how AI search like ChatGPT and Google’s AI Overviews are changing local lead flow, and what it takes to get your company verified without paying a dime. Matt also reveals new details on their Top 100 Property Managers campaign.

Here’s what we go deep on:

🔎 How the TrueMatch scoring model works by looking at performance, trust, experience, and verification

🤖 The AI search shift and why zero-click results are pulling away the “best property manager in [city]” leads that used to land on your site

✅ How verified profiles and owner survey data can help you close faster and keep more clients

🚫 Why PropertyManagement.com refuses to be a pay-to-play lead gen marketplace and what their actual monetization looks like

🌍 If you’re in multiple markets, how the system creates city-specific scores instead of lumping you under one grade.

Want your spot on the Top 100? Apply and get verified for free before 11/30/2025: https://propertymanagement.com/verification

Programming note: This is a mid-season sponsored podcast special with PropertyManagement.com. I accepted support to take a deeper look at their platform, but the conversation, opinions, and questions are my own.

⏱️ Chapters

• 00:00 – Intro
• 01:27 – What is PropertyManagement.com?
• 02:58 – The vision behind PropertyManagement.com
• 04:16 – Building trust in property management
• 08:01 – Navigating the AI search era
• 19:26 – Matt’s journey and industry insights
• 26:49 – Verified performance data
• 32:11 – Monetization strategy and AI search
• 37:35 – Top 100 property managers list
• 40:44 – Balancing integrity and business growth
• 44:49 – Handling large property management companies
• 49:10 – Credibility platform: A new category
• 51:37 – Conclusion and call to action

Resources for Property Managers & Real Estate Entrepreneurs

• Crane – Private PM Owner Community → Join a private network of property management owners and operators: https://joincrane.co/
• Free Weekly Newsletter → Property management insights, strategies, and industry updates direct to your inbox: https://peter.beehiiv.com/subscribe
• RL Property Management → Learn more about Peter’s company and services in Columbus, Ohio: https://rlpmg.com/