As AI tools and automated platforms flood the short-term rental industry, the greatest risk to your business isn't lack of software, it's the rapid erosion of trust. In this episode of The Accommodation Show, Bart Sobies sits down with Margot Schmorak, CEO and co-founder of Hostfully, to examine what it takes to build a truly resilient accommodation business heading into 2027.

Margot opens up about Hostfully's internal tech evolution, candidly discussing why they refocused on product after underinvesting in engineering for several years, why they strictly hire senior engineers in an AI-driven environment, and why they are completely comfortable letting 1,000-unit enterprise clients walk away to focus obsessively on growing 5-to-30-unit managers.

Drawing from her recent stays across Colombia and Greece, Margot also breaks down why operators must stop orienting strictly around physical inventory and start designing their operations around traveler personas. Plus, we explore the reality of AI adoption: why true automation is still unfinished, why operators must "squint" at data, and how to maintain authentic human accountability.

Guest: Margot Schmorak, CEO & Co-founder of Hostfully
Website: https://www.hostfully.com

In this episode, we discuss:
00:00 - Conference Season Wrap-Up & Global STR Stays
02:30 - Hostfully's Engineering Overhaul & Strategic Investment
05:15 - Why Hostfully Refuses to Hire Junior Engineers in the AI Era
08:40 - The "All-in-One" Myth: Why Hostfully Doesn't Target 1,000-Unit Enterprise Portfolios
12:10 - Apple vs. Google: Curating In-House Tech vs. Wild West Marketplaces
16:00 - Travel Insights: Cartagena, Athens, and Bogota
19:30 - Orienting Around Clientele vs. Physical Inventory
23:15 - The Two Waves of Tech: Unfinished Automation vs. Sentiment Listening
27:00 - Why AI Is Never "Set and Forget": Training Intercom's Fin
30:45 - Looking Ahead to 2027: The Erosion of Trust in Data & Software
34:20 - The Importance of "Squinting" at AI Outputs and Self-Assessment

Show links
Hostfully: https://www.hostfully.com
The Accommodation Show: https://www.theaccommodationshow.com
Join the mailing list: https://news.theaccommodationshow.com/
Accommodation Owners and Managers Facebook Community: https://bit.ly/AMoFacebookCommunity
Connect with Bart Sobies: https://www.ibooked.online/bart/
Come to STRIVE: https://www.striveconferences.com

Hotel, BNB and STR owners: need more direct bookings or a brand new website? https://www.ibooked.online

Disclaimer: The content shared on this podcast reflects personal opinions and insights. It is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions.

Most software companies supporting 9,000 clients carry 120 to 150 employees on the payroll. OwnerRez manages it with roughly 50.

In this episode of The Accommodation Show, Bart Sobies sits down with Paul Waldschmidt, CEO and co-founder of OwnerRez. Paul breaks down the operational philosophy that allowed OwnerRez to bootstrap to 9,000 customers without taking a single dollar of venture capital, seed money, or outside investment.

We dive deep into why OwnerRez intentionally feels the friction of scale before hiring, how their tenure-based Employee Profit Sharing (EPS) program has paid out for 28 consecutive quarters, and why shipping 1,000+ software updates a year keeps their engineering team light years ahead of bureaucratic competitors.

Paul also shares the personal turning points of the business: the framed text message from his wife in 2012 that kept him from shutting down, giving away 50% equity to his childhood friend Chris Hines on pure trust, and how designing onboarding into a "pit of success" for 1–30 unit operators reignited rapid growth.

Guest: Paul Waldschmidt, CEO & Co-founder of OwnerRez
Website: https://www.ownerrez.com

📋 In this episode, we discuss:
00:00 - Introduction & Company Philosophy: Creating Happiness
03:40 - The History of OwnerRez: From Cabin Renovations to 9,000 Customers
07:15 - The 2012 Turning Point: The Framed Text That Saved the Business
10:30 - Splitting Equity 50/50: Bringing on Co-Founder Chris Hines
15:10 - The Power of Bootstrapping: Why Profit Equals Freedom
19:45 - 9,000 Customers with 50 Employees: The Lean Headcount Strategy
24:10 - Inside the Employee Profit Sharing (EPS) Program (28 Quarters Strong)
28:50 - Speed as a Feature: Shipping 1,000+ Software Releases a Year
32:40 - Post-COVID Normalization vs. Reigniting Rapid Growth in 2025/2026
36:15 - The "Pit of Success": Doubling Down on 1–30 Unit Operators
40:30 - Paul's Number One Advice for Founders and Operators

#ShortTermRentals #OwnerRez #PropertyManagement #Bootstrapping #SaaS

SHOW LINKS
OwnerRez — https://www.ownerrez.com
The Accommodation Show — https://www.theaccommodationshow.com

Don't forget to hit that subscribe button! This keeps us going and creating more useful content for free!

ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!
📧 Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/
🌍 Join the Accommodation Owners and Managers Facebook Community: https://bit.ly/AMoFacebookCommunity
🔗 Connect with Bart Sobies for industry insights, tools, and resources: https://www.ibooked.online/bart/
🎙 Catch every episode of The Accommodation Show here: https://www.theaccommodationshow.com
✨ Ready to take things up a level? Come to STRIVE: https://www.striveconferences.com

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🥊 Hotel - BNB - STR Owners! 🥊
Need more direct bookings or a brand new website?
The trusted tech partner you can count on. We deliver results.
🥊 https://www.ibooked.online 🥊

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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.

Affiliate Disclaimer:
This blog, podcast & youtube channel will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links. This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them. If you do purchase through my affiliate links, I want to thank you for your support.

Managing from a distance works fine. Operating from a distance doesn't. In this episode of The Accommodation Show, Fred Cercena from Getaway VR breaks down how he manages 70+ vacation rentals across Vermont and Maine from his base in New York.

Fred shares why remote management requires physical local hubs for supplies, how he built an internal promotion track that turned a local housekeeper into a General Manager running two states, and why keeping your tech stack small beats constantly chasing new software.

We also dive into his lean tech setup—including Streamline PMS, SendSquared CRM, dynamic pricing with a dedicated revenue manager, and using Claude AI via MCP connectors to run nightly audits across system data.

Guest: Fred Cercena, Founder of Getaway VR

Website: getawayvr.com

📋 In this episode, we discuss:

00:00 - Introduction & Managing 70 Properties from NY

03:10 - Car Sales Marketing Tactics Applied to STR Photos

07:25 - Doubling Portfolio Size via Business Acquisition

11:40 - The Reality of Remote Management: Why You Still Need a Local Hub

16:15 - Building a Team: Promoting Housekeepers to General Managers

20:50 - Why You Must Earn the Right to Step Out of Daily Operations

25:30 - Being Known in the Community (Chamber of Commerce)

30:10 - The Lean Tech Stack: Streamline, SendSquared, & SMS Agreements

34:45 - Dynamic Pricing: Treating PriceLabs Like a Ferrari

39:00 - Running Nightly AI Audits on PMS Data via Claude MCP

43:15 - 3 Rules for Expanding Into Remote Markets

#ShortTermRentals #RemotePropertyManagement #PropertyManagement

SHOW LINKS

Getaway VR — getawayvr.com

Streamline PMS — streamlinevrs.com

SendSquared — sendsquared.com

PriceLabs — pricelabs.co

Don't forget to hit that subscribe button! This keeps us going and creating more useful content for free!

ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!

📧 Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/🌍 Join the Accommodation Owners and Managers Facebook Community: https://bit.ly/AMoFacebookCommunity🔗 Connect with Bart Sobies for industry insights, tools, and resources: https://www.ibooked.online/bart/🎙 Catch every episode of The Accommodation Show here: https://www.theaccommodationshow.com✨ Ready to take things up a level? Come to STRIVE: https://www.striveconferences.com

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬🥊 Hotel - BNB - STR Owners! 🥊Need more direct bookings or a brand new website?The trusted tech partner you can count on. We deliver results.🥊 https://www.ibooked.online 🥊▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

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.

Affiliate Disclaimer:This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.If you do purchase through my affiliate links; I want to thank you for your support.

Every operator eventually hits the stage where they decide it’s time to stop relying on OTAs and build a real brand. But hiring a designer and building a website isn't enough. In this episode of The Accommodation Show, Miles Hobson, Head of Marketing at Hospitable, breaks down what a real short-term rental brand actually is and how to build one that drives repeat direct bookings.Miles shares the "Nike vs. Hyatt" branding framework, explains why custom direct booking websites fail without a traffic strategy, and reveals how Hospitable scaled to 24,000+ hosts and 200,000+ doors largely through organic word-of-mouth.We explore practical, low-cost grassroots tactics to build brand equity—from local coffee shop partnerships and in-home QR codes to using AI tools to define your brand voice.Guest: Miles Hobson, Head of Marketing, HospitableWebsite: hospitable.com📋 In this episode, we discuss:00:00 - Introduction & Hospitable's Global Scale03:10 - How Hospitable Scaled to 24,000+ Clients via Word-of-Mouth07:45 - What is a Brand? The Nike vs. Hyatt Framework12:15 - Why Your Direct Booking Website Isn't the First Priority16:40 - Low-Cost Grassroots Tactics for Local Brand Building21:10 - Using AI to Refine Your Brand Voice & Values26:30 - In-Home Touchpoints That Turn OTA Guests Into Direct Bookers31:00 - 3 Steps to Start Building Your STR Brand Today#ShortTermRentals #DirectBookings #PropertyManagementSHOW LINKSHospitable — hospitable.comDon't forget to hit that subscribe button! This keeps us going and creating more useful content for free!ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/🌍 Join the Accommodation Owners and Managers Facebook Community: https://bit.ly/AMoFacebookCommunity🔗 Connect with Bart Sobies for industry insights, tools, and resources: https://www.ibooked.online/bart/🎙 Catch every episode of The Accommodation Show here: https://www.theaccommodationshow.com✨ Ready to take things up a level? Come to STRIVE: https://www.striveconferences.com▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬🥊 Hotel - BNB - STR Owners! 🥊Need more direct bookings or a brand new website?The trusted tech partner you can count on. We deliver results.🥊 https://www.ibooked.online 🥊▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬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.Affiliate Disclaimer:This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.If you do purchase through my affiliate links; I want to thank you for your support.

Most broken processes survive in business for years because fixing them means stopping work that pays to do work that doesn't. When new tax laws hit Wanaka, Kim Stewart turned a 200-invoice monthly nightmare into a 10-minute automated sync.In this episode of The Accommodation Show, Kim Stewart from Lakeview Properties shares how she bought a 25-property business running on spreadsheets, kept 95 percent of owners during the transition, and tripled her portfolio.We explore how she navigated major New Zealand GST changes, modernized her PMS and dynamic pricing stack, and trained herself to stop reacting to every guest message.Guest: Kim Stewart, Owner, Lakeview PropertiesWebsite: lakeview-properties.com📋 In this episode, we discuss:00:00 - Buying an STR business and keeping 95% of owners03:15 - Why year one is about not rocking the boat08:40 - Running 25 properties on manual spreadsheets14:20 - The New Zealand GST tax shift that broke the business20:10 - Slashing 200 manual invoices down to a 10-minute sync26:35 - Building the tech stack: Hostaway, PriceLabs, Sweeply33:15 - Why small-town operators need to leave the building38:00 - Training yourself to stop reacting to guest comms#PropertyManagement #STRGrowth #ShortTermRentalsSHOW LINKSLakeview Properties — lakeview-properties.comHostaway — hostaway.comPriceLabs — pricelabs.coXero — xero.comSTRive — striveconferences.comDon't forget to hit that subscribe button! This keeps us going and creating more useful content for free!ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/🌍 Join the Accommodation Owners and Managers Facebook Community:https://bit.ly/AMoFacebookCommunity🔗 Connect with Bart Sobies for industry insights, tools, and resources:https://www.ibooked.online/bart/🎙 Catch every episode of The Accommodation Show here:https://www.theaccommodationshow.com✨ Ready to take things up a level? Come to STRIVE:https://www.striveconferences.com▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬🥊 Hotel - BNB - STR Owners! 🥊Need more direct bookings or a brand new website?The trusted tech partner you can count on. We deliver results.🥊 https://www.ibooked.online 🥊▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬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.Affiliate Disclaimer:This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.If you do purchase through my affiliate links; I want to thank you for your support.

Conventional logic says you must dominate one market before expanding. BNB Breeze ignored that rule and built a 175-property business across 14 states.

In this episode of The Accommodation Show, Heather Schlabach (COO of BNB Breeze) explains why following real estate investors across 14 states created a resilient national portfolio, and why taking on 50 properties in a single local market (Sarasota) was actually harder than operating nationally.

Heather shares how her team recruits boots-on-the-ground cleaners using local community networks, standardises spec sheets across hundreds of listings, and relies on three core values to empower remote contractors to make decisions independently.

Guest: Heather Schlabach, Co-Owner & COO, BNB Breeze

Website: bnbbreeze.co [confirm URL]

📋 In this episode, we discuss:

00:00 - Scaling 175 properties across 14 states centrally

05:54 - Following investors instead of chasing single markets

08:03 - Finding cleaners on street corners and church networks

11:38 - Why acquiring 50 homes in Sarasota broke their systems

14:33 - Warehouse logistics vs direct cleaner shipping

18:29 - Standardising setup spec sheets and biannual deep cleans

21:23 - The 3 company values that replace micromanagement

25:15 - How to evaluate multi-market expansion

#STRManagement #PropertyManagement #ShortTermRentals

SHOW LINKS

BNB Breeze: bnbbreeze.co [confirm URL]

Don't forget to hit that subscribe button! This keeps us going and creating more useful content for free!

ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!

📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/

🌍 Join the Accommodation Owners and Managers Facebook Community: https://bit.ly/AMoFacebookCommunity

🔗 Connect with Bart Sobies for industry insights, tools, and resources: https://www.ibooked.online/bart/

🎙 Catch every episode of The Accommodation Show here: https://www.theaccommodationshow.com

✨ Ready to take things up a level? Come to STRIVE: https://www.striveconferences.com

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

🥊 Hotel - BNB - STR Owners! 🥊

Need more direct bookings or a brand new website?

The trusted tech partner you can count on. We deliver results.

🥊 https://www.ibooked.online 🥊

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

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.

Affiliate Disclaimer:

This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.

This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.

If you do purchase through my affiliate links; I want to thank you for your support.

Sourcing all your bookings from OTAs is costing you thousands in hidden commission fees. In this episode of The Accommodation Show, Rose Tipka from Your Family's Place breaks down how spending $3,500 on direct marketing generated over $100,000 in direct bookings in a single month: saving up to $20,000 in platform commissions.

Rose shares her exact ad budget breakdown, how she caught OTAs bidding on her personal name on Google Search, and why niche family-first hospitality creates a 70% direct booking rate.

Guest: Rose Tipka, Founder, Your Family's Place

Website: yourfamilysplace.com

📋 In this episode, we discuss:

00:00 - Introduction & Building 15,000 Sq Ft Custom Rentals

03:15 - Turning $3,500 Marketing Spend Into $100,000 Direct Revenue

08:40 - Why OTAs Were Bidding on Rose's Personal Name

14:20 - The "Waist-Down Rule" for Stress-Free Family Stays

20:10 - Splitting Meta and Google Ads for Maximum ROI

26:35 - The "Friendly Aunt" Email Marketing Strategy

33:15 - How Interactive Floor Plans Increase Website Conversions

38:00 - 3 Simple Steps to Start Collecting Guest Emails Today

#DirectBookings #VacationRentalMarketing #HospitalityManagement #AccommodationShow #BookDirect

SHOW LINKS

Your Family's Place: yourfamilysplace.com

Hosting in the Motherhood: instagram.com/hostinginthemotherhood

Don't forget to hit that subscribe button! This keeps us going and creating more useful content for free!

ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!

📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/

🌍 Join the Accommodation Owners and Managers Facebook Community:https://bit.ly/AMoFacebookCommunity

🔗 Connect with Bart Sobies for industry insights, tools, and resources:

https://www.ibooked.online/bart/

🎙 Catch every episode of The Accommodation Show here:

https://www.theaccommodationshow.com

✨ Ready to take things up a level? Come to STRIVE:

https://www.striveconferences.com

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

🥊 Hotel - BNB - STR Owners! 🥊

Need more direct bookings or a brand new website?

The trusted tech partner you can count on. We deliver results.

🥊 https://www.ibooked.online 🥊

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

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.

Affiliate Disclaimer:

This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.

This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.

If you do purchase through my affiliate links; I want to thank you for your support.