Tune into the Hospitable Hosts Podcast

In this episode of the Hospitable Hosts podcast, Waigwa shares his journey from a single room rental in London to managing over 20 properties. He discusses the evolution of his business, the challenges of maintaining high standards in guest experiences, and the importance of building trust with property owners. Waigwa emphasizes the need for patience and consistency in the short-term rental market and offers insights into how he differentiates his services to attract property owners.

For more information: https://www.hostmynest.co.uk/about-us

Timestamps:
0:00 - Introduction
4:15 - Evolution of the short-term rental business
7:00 - Scaling the Airbnb business
8:20 - Challenges of Airbnb hosting
10:00 - Challenges of working with property owners
11:47 - Pitching to property owners
13:15 - Using Hospitable for Airbnb management

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, we chat with Josh Difani, Licensed Realtor and Owner of Hidden JEM Hosting, offering full-service property management in Northeast Oklahoma, Northwest Arkansas, and Kansas City, KS.

With over a decade of experience in real estate investing and sales, Josh specializes in selling real estate and managing short-term rentals for clients who want to make their investments passive. Currently, Josh manages 26 STR properties and uses Hospitable to streamline operations.

Josh shares how he and his wife first got into short-term rental hosting, why they started managing STR properties for others, their business goals, and how they vet property owners to work with. He also shares what he loves about hosting and what makes their business different.

For more information: https://www.instagram.com/hiddenjemhosting/

Timestamps:
0:00 - Introduction
4:11 - Getting to 26 Short-Term Rentals
9:01 - Picking out great properties to manage
10:39 - Pitching to property owners
14:15 - Short-term rental tech stack
16:20 - Pros and cons of Airbnb hosting

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, Robert and Nicole from Wandermore Hosting share their journey of co-hosting 19 properties across the US. They discuss the challenges and strategies of managing properties remotely, the importance of guest communication, and the technology tools that help streamline their operations. They also delve into their process of finding and vetting property owners, the rewarding aspects of being short-term rental hosts, and how potential clients can connect with their services.

For more information: https://wandermorehosting.com/

Timestamps:
0:00 - Introduction
2:09 - Managing Properties Remotely
3:50 - Using Hospitable for Guest Communication
6:14 - The Tech Stack
7:52 - Growth Strategies
10:55 - Choosing the Right Property and Owners
14:50 - Red Flags to Notice
16:50 - Why Short-Term Rental Hosting

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On this episode of the Hospitable Hosts podcast, we're joined by Ryan Dumka and Sarah Crawford of Desert Concierge Management. They've scaled their short-term rental business to over $3 million in booking revenue. And they're here to share what it really takes to grow, automate, and thrive in this industry.

Timestamps:
0:00 - Introduction
7:46 - Building a hosting business
13:10 - Dynamic pricing strategies
17:10 - Advice for beginner hosts

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Today’s guest is Ehab, the powerhouse behind Rehab with Ehab—an academy that’s helping short-term rental hosts level up their game. He’s not just an educator; he’s a hands-on property manager who knows what it takes to build and scale a thriving STR business.

In this episode, we talk about how he got started, the lessons he teaches his students, and how tools like Hospitable help him streamline operations and focus on what matters most—growth and guest experience. Whether you’re a new host or a seasoned pro, this is an episode packed with actionable insight and inspiration.

https://www.instagram.com/rehabwithehab_/
https://www.rehabwithehab.com/

Timestamps:
0:00 - Introduction
1:11 - Ehab's portfolio
1:51 - Rehab with Ehab Academy
4:02 - Misconception about short-term rentals
5:03 - Mindset of a successful host
6:50 - Lessons learned in property management
8:24 - Finding the right tools
11:44 - Day-to-day operations
13:26 - Advice for beginner hosts

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On this Hospitable Hosts podcast episode, our guest is Amy Servis. She's a Hospitable customer on the Mogul Plan, and a property manager hosting in the Poconos area.

Timestamps:
0:00 - Introduction to Amy's journey
4:04 - Building the business
6:26 - Optimizing processes with technology
10:15 - Pros and cons of hosting
12:18 - Finding a property manager
17:20 - Building relationships with the owners
18:45 - Focusing on local properties

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On today's episode of the Hospitable Hosts podcast, we are speaking with Libby Ross of Co-host Oklahoma (https://www.cohostoklahoma.com/). Libby is a Mogul plan user with 40+ properties. She's here to tell us a lot more about her experience going into hosting and her experience with Hospitable.

Timestamps:
0:00 - Introduction
2:50 - Libby's team
4:00 - Growth plans
5:02 - Pros and cons of co-hosting
7:10 - How property owners can find a good co-host
9:27 - Qualities of a good co-host
10:35 - How co-hosts can choose the right property owners
13:35 - How Libby uses Hospitable

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On this episode of the Hospitable Hosts podcast, we are joined by Joanne Whitby-Lee, Area Manager at Booking.com. Joanne is responsible for the leadership of teams across Australia and oversees the management of Booking.com's accommodation partners.

We discussed Hospitable’s integration with Booking.com, and how that makes it easier than ever for hosts to list and manage their properties on Booking.com directly through the Hospitable platform.

Timestamps:
0:00 - Introduction
3:01 - Premier Partner Program
7:24 - Listing your property on Booking.com
8:52 - Booking.com's strategy for Property Managers
12:07 - Partner Program impact on guest experience
14:42 - Integration benefits for different types of hosts
16:53 - Short-term rental market trends (APAC)
21:24 - Why use Hospitable with Booking.com
25:37 - Maximizing your success on Booking.com

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On today's episode of the Hospitable Hosts podcast, our guest is David Hillar from Casa Co-host located in Toronto, Ontario, Canada. We're going to hear a bit more about how David has grown his business and how he became an investor in Hospitable as well as a customer.

https://casacohost.com/

Timestamps:
0:00 - Introduction
4:02 - Business processes now and at the start
6:10 - Property management automation
10:33 - Finding the right property manager
13:33 - Choosing the right property owner

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

What does it take to evolve from one of Airbnb’s very first hosts to running a thriving short-term rental business with a growing portfolio of luxury properties? Erika Sampaio, founder of Manage This Home, joins us to share her remarkable 16-year journey in hospitality—from navigating the chaos of early OTA management, to pivoting during the pandemic, to building a resilient, guest-first brand in New York’s competitive Catskills market.

You can connect with Erika via her website https://www.managethishome.com/ and Instagram https://www.instagram.com/managethishome/

Timestamps:
0:00 - Introduction to Erika's business
8:07 - Trips to drive more direct bookings
11:50 - The challenges of hosting
16:00 - Top Hospitable features
21:08 - Advice to owners for choosing a property manager

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On today's episode of the Hospitable Hosts podcast, we're speaking with James Varley from Host Planet. James will tell us a bit more about Host Planet and how you can use their resources to learn more about hosting, get some tips and tricks from them and from industry experts. James will also tell us more about the Host Planet Playbook, something that we're collaborating with them on over the next couple of months, and that you can get involved in.

Follow this link to learn more and sign up: https://www.hostplanet.club/post/host-planet-hospitable-launch-global-collaboration-to-spotlight-str-superstars

Timestamps:
0:00 - Introduction
2:38 - Overview of Host Planet
7:15 - Global reach and audience
9:36 - Host Planet Playbook initiative
11:53 - How can Hospitable hosts get involved

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Unlock the playbook behind Michael Elefante’s short‑term‑rental empire in this fast‑paced episode. We dive into how he’s using Hospitable’s AI, direct‑booking engine, and top‑notch support to automate away the headaches and boost profit. Michael also shares fresh 2025 STR trends - from shifting guest expectations to pricing tactics, and reveals why he launched BNB Investor Academy to help everyday investors scale just like he did. Tune in for actionable gems, market foresight, and a dose of host‑to‑host inspiration.

bnbinvestoracademy.com
https://www.instagram.com/melefante6

Timestamps:
0:00 - Introduction
1:45 - BNB Investor Academy
4:08 - Michael's property portfolio
6:14 - Michael's team
7:17 - Using Hospitable
8:50 - Why use a Property Management Software
10:21 - Most useful features
11:30 - Other software for STRs
13:10 - Upcoming industry trends
15:00 - Thoughts on direct bookings

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

On today's episode of the Hospitable Hosts podcast, we sit down with Jason Muth, an SDR entrepreneur, coach, and founder of Pride Away Stays (https://prideawaystays.com/).

Jason shares how he left behind the corporate media world and built a thriving short-term rental business in Provincetown, Massachusetts, with a strong mission to make hosting more inclusive and more efficient. From hitting $100,000 in direct booking revenue to co-hosting for others to running an SDR coaching business and podcasts, Jason is doing it all.

Timestamps:
0:00 - Introduction
2:24 - Going into hosting full-time
6:24 - Growing Pride Away stays
9:17 - Advice for new property managers
13:02 - Essential tools for hosting success
17:05 - Growing direct bookings to 100k
25:18 - Closing notes

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

We’re excited to welcome Dana Lynch to the Hospitable Hosts podcast. Dana is a short-term rental host based in Austin, Texas, with properties in Osage Beach, Missouri. Dana started her hosting journey while working full-time as a real estate closer—learning the ins and outs of the business by listening to podcasts during her 2.5-hour commute to work. Initially, she relied on a property manager but quickly realized that communication was lacking, pushing her to take control of her business with the help of automation tools like Hospitable. Now, she’s on a mission to scale her portfolio, aiming to add seven more properties this year.

Timestamps:

0:00 - Introduction
1:16 - Getting started with short-term rentals
3:30 - Real estate knowledge
4:22 - Learning from podcasts
8:50 - STR beginner challenges
11:00 - Most useful Hospitable features
13:53 - Future goals
15:40 - Advice for aspiring hosts

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, we are joined by the team behind Crewdogs, a veteran-owned vacation rental company that brings a whole new meaning to hospitality by leveraging their military backgrounds to build a strong brand centered on trust, excellence, and service. Crewdogs is proving that short-term rentals can be more than just a business. It can be a mission.

We are also joined by three hosts who use both CrewDogs and Hospitable.

Follow Crewdogs on Instagram: https://www.instagram.com/staycrewdogs/

Timestamps:
0:00 - Introduction
5:47 - Inspiration behind Crewdogs
8:08 - Veteran community response to Crewdogs
10:05 - Getting started with hosting
14:26 - Memorable guest stories
16:37 - The importance of technology in hosting
20:11 - Advice to military families considering hosting
24:42 - Future goals for Crewdogs
26:13 - Future goals for the hosts


============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In today's episode of the Hospitable Hosts podcast, we’re diving into the latest short-term rental trends with Daniel from Key Data. Key Data is at the forefront of tracking performance metrics for the vacation rental industry, and Daniel will give us an inside look at how the market performed in Q1 — from ADR and RevPAR shifts to booking patterns and guest behavior. Plus, he’ll share what hosts should expect for the rest of 2025 and how to stay competitive.

Timestamps:
0:00 - Introduction
1:39 - US short-term rental market Q1 performance insights
4:55 - Tariff impacts in Q2
7:25 - Average daily rates trend
10:15 - Changes in the length of stay
12:10 - Changes in the booking channels
13:50 - Communicating market changes to property owners
16:45 - Key data points to look at
19:20 - Potential future market shifts

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, we're speaking to Scott McAdara from Branson Lakes Lodging. Scott is a property manager with over 60 properties and growing. He is using our Mogul plan to help him automate many of the processes for his property management business.

Scott will tell us a bit more about how he's been able to grow his business and how Hospitable has helped him along the way.

Timestamps:
0:00 - Introduction
2:25 - Growing the short-term rental business
4:31 - Future growth plans
6:32 - The pros and cons of hosting
10:06 - Finding the right property manager
13:32 - Vetting STR owners
15:33 - How Scott uses Hospitable

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, we sit down with Eric Bell, founder of Milux and a dedicated Hospitable customer. Eric shares his inspiring journey from working as an electrical engineer to launching a thriving short-term rental business—all while managing properties remotely. From the challenges of arbitrage to the nuances of co-hosting, Eric walks us through his strategy for automating operations, scaling his business, and incorporating smart home technology to enhance guest experiences.

Eric recognizes that taking the time and effort to learn Hospitable features and utilizing them in his business processes will result in a value add for everyone involved. As owners/hosts, sometimes it’s difficult to identify what is important. Many tasks are urgent in this industry, but focusing effort on the important is essential, and tools are essential.

Whether you’re an aspiring host or a seasoned STR professional, Eric’s insights on systemization, risk mitigation, and the future of hospitality tech are not to be missed. You can find Eric on Instagram @ericbellreal or contact him via his website: https://www.miluxstays.com/

Timestamps:
0:00 - Introduction
2:20 - Balancing short-term rentals with a full-time job
4:49 - The growth of Eric's business
9:48 - Lessons learned about rental arbitrage and co-hosting
13:00 - Managing STRs in urban vs vacation markets
16:05 - Smart home tech for short-term rentals
22:26 - Closing thoughts

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

We have a special episode of the Hospitable Hosts podcast today. The CEO of Happy Guest, Mike O'Connell, helped us to gather up a panel of four hosts who are using Hospitable and Happy Guest to help them upsell and automate their guest experience. Listen in for tips on where to start with upsells, what kind of products and services you should be offering, and also some extra tips on guest experience and direct booking. You will also get to hear some crazy guest stories at the end.

Timestamps:
0:00 - Introduction
2:52 - Starting with short-term rental upsells
6:44 - Upsell demand from guests
7:20 - Early check-in process
7:58 - Navigating the upsell process
11:06 - The fine line between upsells and a 5-star guest experience
11:56 - Acting as a concierge for the guests
13:35 - Marketing upsells to the guests
16:06 - Upsell fulfillment
17:36 - Bad upsell experiences
19:52 - Upselling local experiences
22:27 - Upsell callouts in guest reviews and messages
24:45 - Tips for getting great guest reviews
28:14 - Enhancing guest experience
30:11 - Experiences with direct bookings
33:35 - Why set up a direct booking website
37:04 - Lessons learned from horrific guest stories

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, we’re joined by Natalie Painter, Broker at Preserve Realty Co. and Owner of Preserve Property Co., a boutique vacation rental management company in the Outer Banks—one of the most competitive and well-established vacation rental markets in the U.S.

Natalie has built a thriving business by leveraging technology, automation, and AI while maintaining a high-touch, personalized guest experience. In this episode, we’ll explore how she’s scaling her business efficiently, why software like Hospitable is crucial for hosts looking to grow while staying lean, and her best advice for homeowners who want to self-manage successfully.

Timestamps:
0:00 - Introduction
2:09 - Starting with short-term rentals
3:55 - Navigating a competitive real estate market
6:05 - AI and automation for short-term rental management
8:20 - Personalizing automated communication
10:00 - Challenges of growing an STR business
12:29 - Getting started in a competitive STR market
14:50 - Starting as a property manager in a competitive market
17:09 - Future STR trends
19:52 - Goals for 2025

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

In this episode of the Hospitable Hosts podcast, we explore the future of short-term rental management, hospitality, and guest experience. Today, we’re diving into a topic that’s reshaping the way hosts operate: AI and Human Power Combined: Transforming the Guest Experience with Real-Time Support.

Our guest is Nicholas Falldine, Head of Product at Extenteam, a company that specializes in helping short-term rental hosts fill staffing gaps with the right talent. Nicholas is here to share his expertise on blending AI efficiency with human touch, ensuring that hosts can deliver outstanding hospitality—at scale.

Timestamps:
0:00 - Introduction
2:50 - AI in Host-to-Guest Communications
4:41 - Balancing AI and Humans
7:12 - Mixing Human Teams and AI for a Seamless Guest Experience
10:50 - Example of Using Hospitable and Extenteam
12:40 - Guest Communication Mistakes
15:43 - AI-Driven Guest Communication for Short-Term Rentals
21:23 - Key Takeaway for Short-Term Rental Hosts


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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Welcome back to the podcast! Today, we're diving into the world of co-hosting short-term rentals with Brandon Pottebaum of BK Stays to uncover how to avoid those common beginner mistakes that can trip up even the most enthusiastic new hosts. Get ready to learn from Brandon's experience and set yourself up for co-hosting success!

Timestamps:
0:00 - Introduction
2:20 - BK Stays Co-Hosting Business
4:13 - Co-Hosting Lessons Learned
9:25 - Short-Term Rental Hosting Tips
12:36 - Favorite Tools for STR Management
17:58 - Future Plans for BK Stays

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Welcome back to another episode of the Hospitable Hosts podcast. Today we're diving deep into a topic that's on everyone's mind: Artificial Intelligence. The listeners who are already Hospitable customers and/or have watched our recent 2025 Roadmap Town Hall (https://www.youtube.com/watch?v=OFle4wurM5Q&t=2s) will know that Hospitable is going big on AI. Another company with a keen AI focus is TIDY, and we have Chris Hawkins, CEO of TIDY, here today to tell us more about his view on AI for STR operations management.

Timestamps:
0:00 - Introduction
1:54 - AI and Property Management for Short-Term Rentals
5:58 - Solving Operational Challenges with AI
8:44 - Future of AI in Short-Term Rental Operations
12:01 - Ensuring Quality Cleaning for Short-Term Rentals
15:30 - Predicting Maintenance Issues
18:45 - AI Use in Daily Operations for Short-Term Rentals

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Welcome back to the Hospitable Hosts podcast! In today's episode, we're diving deep into the future of guest experience management with Shiven Khera, CEO of LinkBase. We're going beyond the basics of automated check-in messages to explore the transformative power of rules-based digital guest journeys and automated upsells.

To get in touch with Shiven and get a copy of the Upsells Script, book a time here: https://calendly.com/shiven-7/30min

Timestamps:
0:00 - Introduction
2:20 - Rules-based guest journey
4:03 - Elevating the guest experience
5:31 - Automated upsells done right
10:17 - Optimal time for upsells
13:39 - Personalizing upsells
15:46 - Success metrics
17:43 - Balancing automation and personal touch

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable