Jacob Morgenstern didn't set out to build a property management company. He started with an e-commerce business, stumbled into short-term rentals in 2020 after reading a book about Airbnb optimization, did well enough to start managing for others — and never looked back.
Today, Jacob runs Stayshores, managing close to 20 properties across Florida, Arizona, and New York, with a target of 40 by end of year. He also runs a fast-growing WhatsApp community for short-term rental operators, sharing hard-won lessons twice a week.
When he switched to Jurny, it wasn't because his old software was broken. It was because he could see what was missing — and a conversation with Jurny's sales team made it impossible to ignore.
The Problem: Good Software That Couldn't Keep Up
Jacob had been using his previous PMS for five years. It was reliable, well-established, and worked — up to a point.
"Changing a PMS is not something you look forward to doing," he admits. "But there were certain bottlenecks that my old software didn't have answers for."
As Stayshores grew, those bottlenecks became friction. Managing reservations across multiple channels meant juggling ICAL links, chasing contact details across platforms, and manually reconciling everything. Guest communication required third-party AI tools to fill the gaps. And scaling to 40 properties on that stack wasn't something Jacob was excited about.
"I needed something more. The other PMS had a strong foundation — but it was clunky. My team needed a clean interface, and I needed something self-intuitive."
Why Jacob Chose Jurny
The switch started with a phone call. Jurny reached out and caught Jacob at the right moment — an hour and a half drive with nothing to do but talk.
"She just told me all about Jurny. I told her all my pain points. And every single one I raised, she said: we can handle this. I was like — really? This is so cool."
Two things stood out immediately. The first was the channel management and Rentals United integration — a direct solution to the cross-platform friction Jacob was tired of managing manually.
"That constant friction has been removed with Rentals United. That's something which was very exciting for me — to have all reservations come in cleanly without going through three different systems."
The second was the interface. After years of software that required workarounds and third-party tools to do basic things, Jurny just worked.
"Jurny has a nice user interface — way better. It's self-intuitive. With my old PMS, I needed tools like third-party AI to complement it. With Jurny, you have that AI built in."
What Changed: NIA, Smart Upsells, and Keeping 200 Guests Calm
Jacob's team handles the day-to-day. But Jurny's NIA has changed what that looks like — especially for guest communication.
NIA learns from your property's history. When a guest trips a breaker and thinks the fridge is broken, NIA knows to tell them about the breaker by the fireplace — because Jacob's team fed that information in. Next time it happens, no digging required. NIA steps in and handles it.
"That's amazing," Jacob says. "You can enable auto-response so you don't have to go digging through past tickets."
NIA's tone-matching feature — mirroring the guest's voice — also keeps interactions professional even in high-pressure situations. Jacob's team recently managed a property where a guest brought 200 people to what was booked as a 9-person stay.
"We had the cops there all night. But through NIA's messaging, we kept everything professional. No negativity. We put in a huge claim afterwards — every additional person, all the damages. But we kept it polite and clean. I think that really helped."
On the revenue side, Jacob is building out smart upsells through Jurny's AI-powered upsell engine. Instead of blasting a generic upsell link in the welcome message and hoping guests remember it months later, NIA detects the right moment.
"When there's a keyword — someone asks about late checkout, or says their flight leaves late — NIA recognizes the request and pushes the upsell right then. They don't have to remember a message from three months ago. It detects it and offers it at exactly the right time."
The Onboarding That Actually Felt Personal
For Jacob, one of Jurny's biggest differentiators isn't a feature. It's the way the company treats its customers.
"I don't think there's any other PMS where someone will actually care if you join — or care if you leave. I was with my old PMS for five years and no one ever sent me an email when I left. Nothing."
With Jurny, the experience was different from day one.
"One of your reps reached out and said: let's schedule an onboarding call. Then a week later again. They reached out again and said — let's have a call, just make sure there are no pain points. It's really, really personal."
Stayshores went from their old PMS to fully onboarded on Jurny in two weeks. And the support didn't stop there.
"Any pain point is just an email away. You have your designated person. They know who you are. That's good to know — and rare."
What Jacob Would Tell Other Operators
"I would recommend Jurny very, very much — just because of the onboarding and the connections. For management companies, the amount of integrations Jurny has is really amazing. Most other companies, it's just: this is what we have. Jurny is personable. They'll work with you. I've seen other PMSs — I'm not impressed. With Jurny, I'm looking forward to many years together."
With nearly 20 properties under management and a target of 40 by year-end, Jacob is scaling Stayshores on Jurny's platform — and building toward a future where every integration, upsell, and guest interaction runs smarter.
"I'm looking forward to many years together."
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