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 bus...
Mar 19, 2025•22 min•Season 3Ep. 46
This episode of the Hospitable Hosts podcast is a throwback. We're re-releasing some of our past masterclass webinars that were available in video format only for you to listen to on the go. The tips and tricks in this episode are still relevant today, but remember that any references to specific dates might be outdated. This webinar ran on June 30, 2023. For this episode, we were joined by Avery Carl, the CEO and Founder of the Short-Term Shop, the premier short-term rental acquisition company....
Mar 13, 2025•57 min•Season 3Ep. 45
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 expe...
Mar 12, 2025•24 min•Season 3Ep. 44
In this Town Hall, the Hospitable team discussed updates on the AI system for Mogul, including a voice-to-text feature and an AI auto-reply feature. The team also discussed the benefits of upgrading to Mogul, the integration of Airbnb's rule sets feature, and the expansion of upsells. Lastly, they addressed customer concerns and discussed potential new features for legacy customers. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking chan...
Mar 06, 2025•1 hr 5 min•Season 3Ep. 43
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! Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad direct booking gues...
Mar 05, 2025•23 min•Season 3Ep. 42
This episode of the Hospitable Hosts podcast is a throwback. We're re-releasing some of our past masterclass webinars that were available in video format only for you to listen to on the go. The tips and tricks in this episode are still relevant today but bear in mind that any references to specific dates might be outdated. This webinar ran on March 13, 2024. We invited tax-saving experts Amanda Han and Matt MacFarland from Keystone CPA to share their insights with Hospitable hosts on correctly ...
Feb 27, 2025•1 hr 1 min•Season 3Ep. 41
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 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. Sleep easy, host confidently ...
Feb 25, 2025•23 min•Season 3Ep. 40
In this Hospitable Town Hall, the team discussed various updates and features, including the automated inbox initiative, new AI features, and the launch of a new Chrome extension called Directo. Upcoming features for the Mogul plan, including AI-powered adjustment handling, customizable statements and invoices, and owner portals, were also covered. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad...
Feb 20, 2025•1 hr 4 min•Season 3Ep. 39
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 . Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your cal...
Feb 18, 2025•22 min•Season 3Ep. 38
Hospitable hosts Tracey and Aahil are short-term rental property managers in Ontario, Canada. In today’s episode, we discuss how Hospitable has helped them grow their property management business, the joys and challenges they face, how they choose which property owners to work with, and their advice on how owners should choose their property manager. Check out the case study we did about one of Tracey's and Aahil's properties. Follow Tracey and Aahil on Instagram and Youtube . Sleep easy, host c...
Feb 11, 2025•24 min•Season 3Ep. 37
In this Hospitable Town Hall, the team discussed updates on smart device integrations, including the launch of a thermostat integration and an increase in the number of free device connections available per active property. Also announced were new features for managing Booking.com reservations, improvements to the mobile app's connectivity and navigation, and the introduction of Stripe Link as a payment method. Additionally, the Hospitable team covered the launch of an incident detection feature...
Feb 06, 2025•1 hr 5 min•Season 3Ep. 36
Welcome back to the Hospitable Hosts podcast! The world of short-term rentals is constantly evolving, and insurance is no exception. Today, we have Darren Nix, Founder and CEO of Steadily , here to help us navigate the STR insurance landscape in 2025 and beyond. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad direct booking guests. Sign up today at hospitable.com/podcast and get 25% off your bil...
Feb 04, 2025•18 min•Season 3Ep. 35
Welcome back to the Hospitable Hosts podcast! In this episode, we're diving deep into the world of STR cleaning with Brooks Sparks of Turno , to learn how a top-notch cleaning strategy can unlock more bookings, better reviews, and a more profitable business. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad direct booking guests. Sign up today at hospitable.com/podcast and get 25% off your bill fo...
Jan 28, 2025•18 min•Season 3Ep. 34
The Hospitable team discusses the company's new roadmap for 2025, focusing on becoming a leading property management software provider in the short-term rental industry with an emphasis on AI integration and connectivity initiatives. The team highlights plans to enhance their product offerings, including improved listing management, dynamic pricing, expense management, and the introduction of a marketplace for service providers. They also emphasize their commitment to creating an owner-centric, ...
Jan 24, 2025•1 hr 4 min•Season 3Ep. 33
Join us as we sit down with Josh Baldovino, a real estate investor who juggles multiple roles with remarkable success. By day, he's a Marketing Manager for a California winery, but his entrepreneurial spirit doesn't stop there. Josh also runs his own marketing agency and manages an impressive real estate portfolio, including a 111-unit apartment complex, 8 long-term rentals, and 4 short-term rentals in Columbus, Ohio. He's mastered various acquisition strategies – from the BRRRR method to wholes...
Jan 23, 2025•21 min•Season 3Ep. 32
Welcome back to the Hospitable Hosts Podcast! Today, we're diving deep into the world of short-term rentals with a true expert in creating unforgettable guest experiences. Joining us is Steph Weber, founder of The Weber Co , a company that helps hosts transform their properties into sought-after destinations through strategic branding, impactful design, and savvy marketing. Steph is also a hands-on host herself, leveraging powerful tools like Hospitable to streamline her operations and maximize ...
Jan 16, 2025•28 min•Season 3Ep. 31
This episode of the Hospitable Hosts podcast features Sally Henry, Vice President of Business Development at Key Data. Sally will provide a deep dive into the latest short-term rental (STR) trends in Australia, sharing key data insights that can help property managers, investors, and hosts better understand the market dynamics. The discussion will focus on how to leverage data to make informed decisions, optimize revenue, and stay ahead in the competitive STR landscape. Sleep easy, host confiden...
Jan 09, 2025•32 min•Season 3Ep. 29
In today’s episode of the Hospitable Hosts podcast, we’re talking to Jeffrey Cottle, Senior Attorney at Anderson Business Advisors. Jeff and Miles dig into some key tax topics for short-term rental hosts in the US including how to decide on a business structure, how to maximize tax deductions, and some of the challenges that come with managing rentals across multiple states. Tax and Asset Protection Workshop Strategy Session Sleep easy, host confidently with Hospitable. Automate your guest messa...
Dec 20, 2024•37 min•Season 3Ep. 28
Today we're joined by Grace Gudenkauf, a real estate investor who took a leap of faith in 2021, leaving her engineering career to build a thriving rental business (including short, mid, and long-term rentals). Now owning and self-managing over 25 units across multiple states, Grace is a master of remote management and a champion for women in real estate. She's here to share her incredible journey, from taking the plunge to building a team and empowering others through her book and community. Get...
Dec 19, 2024•19 min•Season 3Ep. 27
Welcome to today's episode of the Hospitable Hosts podcast with Founder and CEO of Boostly , Mark Simpson. Mark is a stand-out professional in the industry, having worked in hospitality (across various roles) for decades, and understands the everyday challenges of hosts. In today's episode, Mark guides us through 6 tips to help you grow direct to be 65% of your bookings. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and pr...
Dec 05, 2024•33 min•Season 3Ep. 26
In this episode, we sit down with Jeff Usner, founder of STR Digital and a successful short-term rental host . Jeff shares his journey into the world of vacation rentals, highlighting the challenges he faced and how he overcame them with the help of Hospitable. Discover how Jeff leverages Hospitable's features to manage his diverse portfolio, maximize direct bookings, and streamline his operations & how he has grown 3 of the top 11 revenue properties in PA, including the #1 revenue property ...
Nov 28, 2024•27 min•Season 3Ep. 25
Join us for a fascinating conversation with Ethan Brown, a Sunshine Coast host who loved Hospitable so much, he joined the team! Ethan shares his journey from clueless newbie to automation-savvy host, revealing how Hospitable transformed his business and allowed him to manage his properties remotely while traveling Australia in a caravan with his wife and dogs! Discover how Ethan's firsthand experience as a host shaped his contributions to Hospitable's growth, from customer support to his curren...
Nov 21, 2024•25 min•Season 3Ep. 23
This episode of Hospitable Hosts dives deep into the world of co-hosting with a unique twist! Join us as we chat with Kevin, a member of the Hospitable customer support team, and his wife Natalia, who were successful Hospitable users before Kevin joined the company. Kevin and Natalia share their inspiring journey of becoming co-hosts, revealing the secrets to their successful partnership. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across bookin...
Nov 07, 2024•30 min•Season 3Ep. 22
Welcome back to Hospitable Hosts! Today we're diving into the dark side of short-term rentals – the horror stories that keep hosts up at night. But don't worry, we've also got the solutions. Joining us is Melissa Bernardo from Alertify to talk noise, smoke, and how to protect your property. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad direct booking guests. Sign up today at hospitable.com/pod...
Oct 31, 2024•21 min•Season 3Ep. 21
Welcome back to Hospitable Hosts! In this episode, we are discussing a great success story. Ekabo Home has made a name for itself in Atlanta, Georgia’s short-term rental industry, thanks to its founder, Niyi Adewole, and his vision for combining property appreciation with cash flow generation. Starting with just one rental property in April 2021, Ekabo Home has grown into a thriving property management business, utilizing Hospitable Direct and automation to streamline operations and achieve succ...
Oct 24, 2024•17 min•Season 3Ep. 20
Welcome back to the Hospitable Hosts podcast! Today, we're diving deep into the world of DSCR loans – a powerful financing tool for short-term rental investors. We're thrilled to have Jeff Ball, the CEO of Visio Lending , here to guide us through the ins and outs of DSCR, sharing his expert insights to help you make informed decisions for your rental portfolio. If you enjoy this episode, don’t forget to live, review, and/or subscribe to the Hospitable Hosts podcast to show your support! Sleep ea...
Oct 17, 2024•21 min•Season 3Ep. 19
Welcome back to the Hospitable Hosts podcast! Today, we're diving into the exciting world of direct bookings. We're thrilled to have Gil Chan, the CEO and Founder of CraftedStays , here to share his expertise on how to create a high-converting direct booking website. If you enjoy this episode, don’t forget to like, review, and/or subscribe to the Hospitable Hosts podcast to show your support! Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across bo...
Oct 03, 2024•24 min•Season 3Ep. 18
Today on Hospitable Hosts, we have a unique story about a Hospitable employee who turned host himself so that he could better understand the challenges that hosts face. Tune in to hear Toby's story of going from being a Hospitable team member to an entrepreneur and the valuable lessons he learned along the way. Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad direct booking guests. Sign up today ...
Sep 26, 2024•16 min•Season 3Ep. 17
In this episode of the Hospitable Hosts podcast, we are joined by Jodi Bourne. Jodi is a vacation rental business and marketing coach, educator, and website designer, with a rich background in business management, brand messaging, digital marketing, and customer service across various industries, focusing on tourism and vacation rentals since 2014. Jodi's passion for tourism and hospitality shines through in her work and everything she does. She is dedicated to helping savvy vacation rental host...
Sep 05, 2024•27 min•Season 3Ep. 16
In this episode of the Hospitable Hosts podcast, we are thrilled to have Jenn Boyles join us. Jenn is a seasoned expert with over 20 years of experience in design and marketing, and more than a decade as a holiday rental owner. She is dedicated to helping short-term and vacation rental property managers, owners, and hosts build and grow their businesses independently, without over-relying on online travel agents. Jenn’s wealth of knowledge and hands-on experience make her the perfect guide for u...
Aug 22, 2024•23 min•Season 3Ep. 15
