AI can answer a resident at midnight. It can also say something it should not, to someone it should not, in a way that breaks a rule. On August 13, 2026, Second Nature hosted a free session with Wolfgang Croskey about the difference.
What was the webinar about?
Second Nature's event page, titled "Level Up Your AI," set the session for August 13, 2026, 2:00 to 3:00 PM Eastern, for single-family property management operators and broker/owners. It listed these topics:
- How Wolfgang's AI work started, the software and AI tools he runs today, the results he can put numbers on, and the failures that taught him more than the wins.
- How to train your AI: where to start, how to build trust, and what to do when it gets something wrong.
- A live look at what happens when AI runs without guardrails, and what supervision catches.
- Five questions to ask any AI vendor before putting its tool in front of your residents.
- Wolfgang's view on compliance: what property managers need to know about Fair Housing, the Telephone Consumer Protection Act (TCPA) and the Fair Credit Reporting Act (FCRA) before AI communicates on their behalf, and how to train the AI so it knows the rules too.
The live question-and-answer was moderated by Andrew Smallwood. The page does not mention a recording, so check Second Nature's page for one.
Why do these three laws matter to an owner?
When a manager lets AI write to residents, applicants or owners, the manager's license and your property carry the risk. The Telephone Consumer Protection Act (TCPA, 47 U.S.C. section 227) governs automated calls and texts. The Fair Credit Reporting Act (FCRA, 15 U.S.C. section 1681) governs how consumer reports, including tenant screening reports, are used. Fair housing law governs how people are treated and what is said about a home. None of these is a technical problem. They are the manager's responsibility, and AI does not move that responsibility to the tool.
What can I ask my property manager?
The webinar's themes turn into plain questions for an owner: who reviews what AI sends, what it may not do, how automated calls and screening reports are handled, and what happens when it is wrong. Our guide to vetting a property manager has more questions to ask, and our guide to who regulates property managers explains what a California broker license covers.
Where does Croskey fit?
Croskey Real Estate, Inc. is a Pittsburg brokerage (DRE #01990430) managing rentals in East Contra Costa. Wolfgang is its CEO, and a co-founder of the PM Systems Conference. His NARPM 2026 session on building or buying AI tools is covered here, and his FUTURE 2026 debate on AI agents is covered too.
If you own rentals in East Contra Costa and want to talk through how your manager uses technology, schedule a call. Our pricing page shows what full-service management includes.
This post is general information, not legal advice. Laws and local ordinances change; confirm your situation with a California attorney.
Frequently asked questions
What was the Second Nature Level Up Your AI webinar?
A free session on August 13, 2026, 2:00 to 3:00 PM Eastern, with Wolfgang Croskey for single-family property management operators and broker/owners, covering how to train AI, guardrails, compliance and five questions to ask any AI vendor.
Which laws should AI follow when a property manager uses it with residents?
The webinar page names Fair Housing, the Telephone Consumer Protection Act (TCPA) and the Fair Credit Reporting Act (FCRA). The manager stays responsible for compliance even when AI sends the message.
Who moderated the live Q&A?
Andrew Smallwood moderated the live question-and-answer with Wolfgang Croskey, according to the Second Nature event page.
