A tenant at Adam Willis's company recently disputed a $1,500 security deposit deduction by filing a small claims suit, reading a script straight off ChatGPT to the judge. He lost in about three sentences. It's a small story, but it's a preview of something bigger: AI is now working both sides of this business, and it's changing how we have to run it.
Adam is CEO of Nestwell Property Management in Utah, and he's been on my show before. This time we got into how his team is rethinking tenant and owner communication from scratch, why he runs an in-house real estate brokerage, how he rebuilt an in-house maintenance company for the second time, what a fractional CFO actually does with 90 days, and (the part that stuck with me most) what it looks like when AI starts generating the lawsuits landing on your desk.
One Phone Number, One Inbox
Adam's team used to build tenant and owner-facing knowledge bases: search a keyword, get a list of help articles. He's moving away from that model entirely. The goal now is something closer to how Delta Airlines handles support: one point of contact that can flex between chat, text, and video, with every interaction logged in order so nothing gets lost.
On the inbox side, Nestwell has already consolidated down to essentially one shared inbox in Help Scout, handling around 300 queries a day, routed by conditional logic to whoever's covering that shift. I liked how he framed the ideal end state: a tenant or owner should be able to save one contact in their phone and reach a human, at an ownership level of sophistication, no matter what they need or which channel they use.
The Trademark Fight Behind an In-House Brokerage
Nestwell has run its own real estate brokerage since long before Adam took over the company, and it's grown to three full-time agents under a "hub and spoke" model: property management is the hub, brokerage is one of several spokes run by someone whose full-time job is exactly that. It operates as a DBA under the same Nestwell brand rather than a separate name, because Adam has found that managing multiple brands across tax filings, disclosures, and marketing isn't worth the trouble.
The naming decision matters more than it looks. Adam told me a common name like his has drawn attention from other companies' trademark attorneys, and he mentioned a friend actually sent him a cease-and-desist years ago over a name he'd been using before he landed on Nestwell. It's a detail worth remembering before you name anything you plan to put on a real estate sign: your management company's name might not be the right name for the brokerage.
Rebuilding In-House Maintenance, Twice
Nestwell has run its own general contracting arm on and off for years, largely because Adam wanted more control over turn times and pricing than outside vendors were giving him. The first version limped along for years with a small, inconsistent crew. It didn't really take off until he brought in Josh, a retired military operator, to run it as its own branded entity with his own equity stake.
That's now a standalone company with seven or eight technicians handling turns and work orders in-house, and Adam's evaluating which third-party vendors to bring in-house next. He was candid that it's genuinely hard: more liability, more oversight, and a level of daily hands-on management that a strong operator like Josh makes look easier than it is.
What a Fractional CFO Actually Does With 90 Days
Adam recently brought on a fractional CFO, Ben Farbowitz, after interviewing several candidates and getting a referral through his EOS implementer. Ben started with a paid diagnostic, then delivered a 14-to-15-page playbook of specific fixes, working on a retainer tied to hitting those items by the end of the quarter.
Two examples stood out: cleaning up a 401(k) rollout that Nestwell's team didn't have the internal bandwidth to finish, and pushing the company off paper checks toward real-time payments instead of ACH. It's a useful model for anyone who needs senior finance help but can't justify a full-time hire: pay for a defined scope, see if it delivers, then decide whether to keep the relationship going.
The Bonus Plan That Punished a Bad Year
One of the more useful admissions in this conversation: Adam had built a company-wide bonus pool tied to year-over-year net income growth. It worked fine while the company was growing, but the year growth flattened, the pool shrank to nothing, even for team members who'd had a genuinely strong year individually. He's since moved to a structure split across KPI performance, peer review, and quarterly priorities, so a company-wide down year doesn't automatically zero out someone who did their job well.
The Takeaway
Every one of these threads traces back to the same instinct: build the thing yourself, on purpose, rather than accept the default. Adam didn't like the fragmented tenant experience, so he's building his own communication layer. He didn't like outside vendor pricing on turns, so he brought maintenance in-house, twice. He didn't like a bonus plan that punished a bad year, so he rebuilt it.
The ChatGPT lawsuit is the same instinct playing out on the other side of the table. Tenants now have access to tools that make filing a claim nearly free, whether or not the claim has merit. Adam's team is winning these cases, but winning still costs time, legal exposure, and morale. And if your property management agreement doesn't already spell out who pays for that, now's a good time to check.
Watch the full conversation with Adam:
Connect with Adam: Nestwell Property Management · Adam on LinkedIn →