HeyJaredPMAssist Industry Insights
In this newsletter, we will discuss topics impacting the property management industry, especially as related to revenue, profitability, systems, and automation.
- Indexed issues, last 90 days
- 21
- Latest publication
- Sep 29, 2026
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- Aug 25, 2026
Latest issues
Your Job Is to Think, Not Grind: What United's CEO Gets Right (opens the original)
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Last night, hundreds, perhaps thousands, of property managers were answering texts and emails from tenants and owners at 10pm. Meanwhile, the CEO of United Airlines, a company with 100,000 employees that literally had hundreds of airplanes in the air at the time, was asleep in his bed at home getting 8.5 hours of sleep, just like he does every night.What’s wrong with this picture? Scott Kirby is the CEO of United Airlines. Recently, he appeared on a podcast and discussed his work schedule and st
The Systems That Got You Here Won’t Get You There (opens the original)
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When a company is growing, revenue is increasing, and clients are being retained, it is natural to assume that the systems supporting that success are working well. In many cases, they are. The challenge is that systems should not be evaluated solely on their ability to support the business at its current stage. They should also be evaluated on their ability to support the next stage.One of the most dangerous assumptions in business is believing that success validates the way things are currentl
Dumb as a Bag of Rocks Until Proven Otherwise (opens the original)
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If you’re going to implement AI agents (and you’ll probably have to at some point, no matter how much it may irk you), then you should onboard those agents to your operation just like you’d onboard a new hire human employee. That’s what we’ll be talking about in today’s article for paid subscribers and Crane members: setting up your AI agents safely to interact with residents, owners, and applicants. Safely.We’ll be covering all of the following:What’s Changed for AI AgentsAI Agent PhilosophyOur
The Phone Is a Trap: Handling AI-Generated Legal Threats Without Handing Over Evidence (opens the original)
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Sometimes AI really is better at responding to someone than a human is. And when things are starting to go down a potential litigious path, I would argue it’s even more important to lean on AI instead of excluding it.Marc Cunningham recently put out a video talking about how to handle it when a tenant sends you a long, legalistic email that was obviously drafted by AI. While I agree with Marc on a lot of things, I do think he’s a bit too skeptical of AI in general, and definitely in this case. S
Don't Wait as Long as I Did: The Layoffs I Should Have Made Years Ago (opens the original)
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Normally these articles teach you about how you should do something based on my experience, but today is going to be a little different. Today I’m functioning as your bad example to not follow. And honestly, that may be even more valuable to you.Yesterday I had to end the employment agreements of three team members at my property management company. They were good employees, and frankly, they had done nothing wrong to deserve losing their jobs. But not every employment termination is for just ca
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