This issue of Pillow Talk, our weekly newsletter, went out by email on August 6, 2026. Get the next one.Editor's note, October 2026: The live events mentioned in this issue have already taken place.
Hey friend,
Welcome to the 49th weekly edition of Pillow Talk! This is where I share my unfiltered thoughts on life, business, and property management.
This week, I’m breaking down a post from Todd Ortscheid about the cash yield trap, and why it matters to PMs.
I was reading a recent post from Todd Ortscheid and decided I need to add another reason to the list of why owners churn: Because they think they found a better investment vehicle.
Todd’s post starts out debunking a claim made by Chris Lopez, co-founder and CMO of Property Llama, on the Bigger Pockets podcast. Property Llama is a portfolio management and financial modeling tool for landlords. In the episode, Chris says:
“Paid off rentals often generate less cash flow than high-yield savings accounts and t-bills.”
While the claim is highly nuanced, what it communicates in the end is that rentals are not a good investment vehicle comparatively. You really should go read Todd’s post, because he laid the claim bare better than I could. But here are the key points:
- Chris’s claim ignores the tax advantages of real estate,
- that real estate produces growing returns (rent goes up every year),
- that leverage is cheaper in real estate,
- and the value of appreciation. Todd compares it to ignoring that a stock can increase in value and focusing only on dividends as a measure of the quality of an investment.
Other PMs Aren’t Your Only Competition
The problem with Chris’s claim is not that it’s generally false. There is a world (or a market) where it could be true. Todd points out that Chris invests in Colorado, where the math is more likely to support his claim.
The real problem is that your clients might take it at face value and cancel with you without first talking to you or doing their due diligence. Heck, they might sign with a realtor before ever saying a word to you about it. Accidental landlords and unintentional investors are particularly at risk here. Intentional, sophisticated investors likely understand there’s nuance to Chris’s claim. But unintentional investors and accidental landlords aren’t true believers in rentals, and could be more-easily persuaded to exit the asset class, especially if a smart guy on the internet is telling them there’s a lower-effort option.
Is Your Team Prepared?
If one of your clients emails their PM tomorrow and says they want to cancel for this reason, will your PM know how to approach the situation? Are YOU prepared to talk numbers and make the case for why real estate is likely a better investment vehicle for them? Does your offboarding even create the opportunity for that conversation?
The reality is most PM teams have never been trained for moments like these. Which is one reason we’ve partnered with Property Management University (PMU) to create the Owner Experience Management Certification. This is the first Client Success training program for residential PMs.
The curriculum includes education and scripts for retention scenarios, so your team knows exactly how to handle a client on the edge. I authored the program based on my experience at a BTR firm where I worked with 1000s of SFR owners. In that role, I learned what makes owners tick.
I’m co-hosting two upcoming webinars that train owner-facing employees on the basics of Owner Experience Management, as well as how to enroll in the certification course:
- Episode 2: Tuesday, August 18th: Love at First Impression - For Business Development Teams
- Episode 3: Tuesday, August 25th: From Service Provider to Trusted Advisor - For Property and Owner Management Teams
98 property management professionals are already registered! And we had a great turn out for Episode 1 for Broker/Owners this last Tuesday 😁 We will run episode 1 again soon. I’ll keep you posted!
Two Things for Staying Ahead of Churn
Here are two things you can start doing now to retain property owners, without taking a course or anything. They’re things I have preached for a while and things we see top PM firms doing:
- Establish yourself as the expert. You need to prove you know what you’re talking about as soon as possible. One way you can showcase your expertise in the asset class is by talking with prospects and clients about their goals with the property and creating tailored plans that help them reach those goals. You can also conduct annual performance reviews and publish educational content on your blog or newsletter.
- Get out ahead of the news. Use that newsletter and your performance review sessions to proactively talk to clients about market trends and what you’re doing to protect returns. This is something that would surprise and delight many owners. And not only will it help prevent owner churn, it will position you as an advisor.
The Roundup
Content worth the click
- Interesting post about farm real estate value
- Are you a viable market solution? - Deb Newell
- Fair Housing as a competitive advantage
- The 3 Levels of Accountability Every PM Business Owner Needs
Good night 😴
Lior Abramovich
Co-founder, CEO
Pillow Talk
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