iBooked Online

Every business drifts.

The longer you run one, the further you get from the thing that made it work in the first place. You add a layer of software. You hand off guest contact. You put a process between yourself and the bit you used to do by hand. Each decision is sensible on its own, and then one day you look up and the operation feels corporate and cold and you can’t point to the moment it happened.

The drift runs the other way too. People trying to break into this industry often start by trying to look bigger than they are. Course frameworks, brand guidelines, a five-year plan, before they’ve ever cleaned a bathroom or fielded a 2am call about a broken air conditioner.

Twenty years in or twenty minutes in, the core drivers don’t really change. Execution beats strategy nearly every time.

This week I sat down with Cathleen Cataldo from Discovered In Travels. Three years ago she was doing corporate fashion trend forecasting in New York City. Today she runs nine short-term rentals in the Poconos with fourteen on the way.

Her start is a good story. She found the term “co-hosting” online, went down the rabbit hole, and told her dad, who builds homes for a living, “if you build one, I’ll learn how to manage it.” He said yes. So while the house went up, she went looking for co-hosting clients so she’d actually know what she was doing by the time it opened.

Her first sales call went badly. The prospect asked how many properties she managed. Cathleen, honest by default, said she was still in the process. The woman said she wanted someone who knew what they were doing, and hung up.

I love that she told me that. Most people would quietly edit that out of their own origin story.

So she went back to the Facebook group and asked it straight. How does anyone get their first property if they don’t have family in this? Someone answered. She was looking for an intern to shadow her and offered to show Cathleen the back end of her Airbnb account. Cathleen had never seen what a host account even looked like.

That woman became her mentor. And Cathleen still has that first client, three and a half years later.

A few things from the conversation worth your time, whether you’re taking on property one or auditing property fifty.

Humility is a shortcut. Instead of burning months making rookie mistakes on her own dime, Cathleen made them on somebody else’s. She asked to shadow, for free, and learned the reps before she needed them. That’s not just a beginner’s move. If you’re an experienced operator eyeing a new market or a new service line, a few days inside someone else’s operation will teach you more than any consultant’s report.

“You can’t outsource local.” She started in the Poconos because it’s her hometown. She knew the regulations, the parking, the working culture, and half the vendors already knew her family. When she rang cleaners and handymen, being local opened doors an out-of-state investor doesn’t get. Everyone is chasing remote management and offshore teams right now, and here’s a brand new operator telling me her single biggest advantage was being from there. If you’re a local operator, that’s a moat a remote company can’t cross. I haven’t stopped turning it over.

Tech should buy you time, not hide you from guests. She set up her PMS before she owned a single property, which is the shift worth noticing. When I started, the PMS was the thing you graduated to once the spreadsheet broke. For her it was the starting line. But she still writes every guest message herself at nine properties. She knows that has a ceiling. She’s holding it as long as she can because she can’t replicate herself yet, and the voice is the product. Newer hosts automate too fast and turn guest comms into robot sequences. Veterans automate and then forget they did. Both are the same mistake.

She kept her corporate job for two full years. Only went full-time in the past year. Built the whole thing on evenings and weekends while the salary kept landing. I want to sit on that, because the loudest voices in this industry sell the opposite. Quit tomorrow, no money down, passive by Christmas. That pitch has done real damage to real people. The honest version is less exciting and far more useful.

“Amenities get the clicks. The experience gets the five-star review.” The Poconos is one of the most saturated STR markets in the US and her answer isn’t price, it’s engineering specific moments guests will name in their review. Which is exactly where Daniel Rouquette landed in Bali last week. Two operators, opposite sides of the planet, same conclusion.

What you’ll learn in this episode:

🤝 How to land your first co-hosting client with no properties and no track record

💡 Why shadowing an established operator beats any course

🧰 The tech stack new operators set up before they own anything

📍 Why local knowledge is still a moat in the age of remote management

⏳ Why building alongside a salary for two years is a feature, not a failure

Cathleen founded Discovered In Travels, a boutique short-term rental management company in the Poconos, Pennsylvania. She came from corporate fashion trend forecasting in New York City, has stayed in over fifty short-term rentals around the world, and now manages nine properties with fourteen on the horizon. She also mentors first-time investors in her market, which given how she got started makes complete sense. discoveredintravels.com or @discoveredintravels on Instagram.

If you’re just getting started, Cathleen had no capital, no property, and no hospitality background. What she had was the willingness to say “I don’t know yet” out loud to a stranger on the internet.

And if you’ve got years under your belt, watch what a new operator reaches for by default. Lean overheads, a tight local network, and guest touchpoints that are still actually hers. The starting line has moved, and the people arriving now aren’t carrying anything they need to put down first.

📺Watch the episode here

🎙️Listen to the show here