OM DENNE EPISODE
She Got Hung Up On. Three Years Later She Has Nine Properties.
Cathleen Cataldo's first sales call ended when the prospect asked how many properties she managed. She said she was still in the process. The woman said she wanted someone who knew what they were doing, and hung up.
Three years later she runs nine short-term rentals in the Poconos, with fourteen on the way.
In this episode we get into the honest version of starting a short-term rental business. Not the guru version. How she landed her first co-hosting client with no properties and no track record, the tech stack she set up before she owned anything, why she kept her corporate job for two full years, and why local knowledge is still a moat in an era of remote management.
If you've been thinking about starting, Cathleen had no capital, no property, and no hospitality background. And if you've been doing this for a decade, watch what a new operator reaches for by default. The starting line has moved.
Cathleen Cataldo — Founder, Discovered In Travels
🌐 discoveredintravels.com
📋 In this episode, we discuss:
00:00 – Meet Cathleen Cataldo: from corporate fashion to short-term rentals
01:36 – Why she operates in the Poconos, not New York
02:15 – "You can't outsource local": the hometown advantage
03:22 – Competing in one of America's most saturated STR markets
04:28 – Amenities get the clicks, experience gets the five-star review
05:25 – How reviews drive the OTA algorithm and your rankings
07:03 – Co-hosting vs owning: how her portfolio is actually structured
07:50 – Leaving corporate America to build something of her own
08:50 – "If you build one, I'll learn how to manage it"
10:03 – The first sales call that ended with a hang-up
11:27 – Faking it till you make it (and why that never really stops)
12:46 – The internship that changed everything
15:22 – The truth about STR gurus and no-money-down promises
16:29 – Why hospitality mindset beats hospitality experience
17:30 – Keeping her corporate job for two years while building
18:28 – Stay in short-term rentals before you run one
20:15 – Setting up a PMS before owning a single property
20:59 – The full tech stack for a new STR business
23:52 – Why PriceLabs over her PMS's built-in pricing
24:36 – Direct booking sites for owned vs co-hosted properties
25:03 – Automating cleaning and keyless check-in
26:30 – Her advice: start in a market you actually know
28:07 – The local logistics most new operators overlook
SHOW LINKS
Discovered In Travels — https://www.discoveredintravels.com
Hospitable — https://hospitable.com
PriceLabs — https://hello.pricelabs.co
Turno — https://turno.com
Schlage — https://www.schlage.com
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Disclaimer: The content shared on this YouTube channel, Podcast, or associated posts reflects personal opinions and insights. This content is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions. The hosts and guests disclaim liability for any consequences of using this content. Actions taken should be based on your personal due diligence.
