Season 23: The Biggest Short-Term Rental Lessons from 10 Industry Leaders

Season 23: The Biggest Short-Term Rental Lessons from 10 Industry Leaders

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G’day Accommodation Professionals,

That’s Season 23 done.

Ten guests, from Chicago to Wanaka to the Poconos. Businesses ranging from a woman who started with no property and no track record, to a company running 700,000 listings on their Saas without ever taking outside money. On paper, almost nothing in common.

Then I went back through the lot, and they kept landing on the same handful of ideas from completely different directions.

The biggest company in our industry got there by refusing complexity. A villa operator in the world’s most oversupplied market held his rates by standing out instead of discounting. A B&B owner in New England built the top-rated property in the country by asking one question about every decision he made. And three separate guests, on three different continents, told me some version of “you can’t outsource local.”

None of it was new. That’s what struck me. The fundamentals of this business have barely moved. What has changed is how many shiny things are competing for your attention while you try to get them right.

The episodes that stood out

🔁 The Retention King: Rose Tipka, Your Family’s Place

Not the most viewed, but by a distance the most finished. People who started this one stayed for an average of fifteen minutes. It’s the episode with the clearest numbers we’ve ever put out: a $100,000 month on about $3,500 of marketing, versus roughly $15,000 had those bookings gone through the OTAs.
https://youtu.be/tHVb75wLY4w

👀 The Most Watched: Fred Cercena, Getaway VR
Managing roughly 70 properties across Vermont and Maine, from New York. The counterintuitive bit is that distance costs you more local infrastructure, not less.
https://youtu.be/FaLKlaHO-18

🗺️ The Close Second: Heather Schlabach, BNB Breeze
175 properties across 14 states, and the twist nobody expects: concentrating into a single market was harder than spreading across fourteen.
https://youtu.be/fK8pDDPPKjQ

🛁 The One I Keep Coming Back To: Marco DiDomizio
“Is that about you, or is that about the guest?” Plus a renovation loan he repaid in a single night. Second-highest completion rate of the season, which tells you something.
https://youtu.be/Uu_JJzgJDcE

🧾 The Sleeper: Kim Stewart, Lakeview Properties
Bought a management business, kept 95% of the owners, then a tax change six months in forced her to rebuild the back office. What took two people a month now takes ten minutes.
https://youtu.be/4JgwjfXOIWM

The full Season 23 lineup

🎙️ Anurag Verma & Richie Khandelwal, PriceLabs — 700,000 listings, zero VC funding, and why every tool you add has a hidden price tag
https://youtu.be/ili6S8ot0Y0

🎙️ Daniel Rouquette, Villa Finder — the Bali market dropped 20%, his dropped 6%
https://youtu.be/IWKweMHRYI0

🎙️ Cathleen Cataldo, Discovered In Travels — hung up on in her first sales call, nine properties three years later
https://youtu.be/yAHKJ60_8Eg

🎙️ Marco DiDomizio — how a sleepy nine-room inn became America’s top-rated B&B
https://youtu.be/Uu_JJzgJDcE

🎙️ Katie Klein, Second Home First — buying your second home first, and finding the advantage you can’t see
https://youtu.be/JgtOcGoZJ44

🎙️ Rose Tipka, Your Family’s Place — the real maths on direct bookings versus OTA commission
https://youtu.be/tHVb75wLY4w

🎙️ Kim Stewart, Lakeview Properties — buying a business, and the tax change that fixed it
https://youtu.be/4JgwjfXOIWM

🎙️ Heather Schlabach, BNB Breeze — 175 properties, 14 states, one central office
https://youtu.be/fK8pDDPPKjQ

🎙️ Miles Hobson, Hospitable — how to build a brand, in the right order
https://youtu.be/RvYEcvnh5LM

🎙️ Fred Cercena, Getaway VR — how to manage 70 properties remotely
https://youtu.be/FaLKlaHO-18

If you’ve got a quiet week coming, don’t start at the top. Pick the one closest to the problem sitting on your desk right now. That’s usually the one that pays for itself.

Thank you for listening, watching, replying and sharing this season. Genuinely. We’ll be back with Season 24 shortly.

And if you want the in-person version of all of this, STRive is back in Melbourne on 10 and 11 March and Auckland on 16 and 17 March.

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