Hospitable Hosts

Hosted by Hospitable

Business Entrepreneurship

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Episodes

171

Latest episode

Oct 2026

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About the show

Hospitable gifts hosts their time back. Our easy-to-use, AI-powered software helps property owners, self-managers, co-hosts, and property managers save time, grow their revenue, and protect their properties and business. In this podcast, Hospitable Hosts, we talk with leading industry experts, Hospitable integration partners, and short-term rental hosts to share valuable insights and ideas with the hosting community. Find out more about Hospitable and start a 14-day free trial: https://hsptb.com/hhpodcast

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60 recent

October 21, 202622 min

The Hidden Revenue Stream in Vacation Rentals with Localbird

On this episode of the Hospitable Hosts podcast, our guest is Ben Levy, Co-Founder and CEO of Localbird. Ben shares how their platform transforms the vacation rental experience by integrating seamless booking of local experiences, leveraging AI and human support, and scaling through strategic vendor vetting and automation. For more information, visit https://localbird.io/ Timestamps: 0:00 - Introduction to Localbird 3:35 - Scaling Localbird internationally 6:43 - The Localbird experience 10:14 - Revenue opportunities and profit potential for hosts 12:22 - Impact of concierge services on reviews and repeat bookings 14:03 - First-week tips for activating Localbird 15:46 - Mistakes hosts make with upsells 18:05 - Vetting vendors and ensuring quality

October 15, 20261 hr 0 min

Inventory Management - Hospitable Town Hall, October 14, 2026

At this Hospitable Town Hall, the team presented a major update to the Tasks app, introducing a voice-to-inventory reporting system for cleaners and a reimbursement workflow for restocking supplies via credit card. They also covered Booking.com updates, including a revamped account connection process, a new listing discount, improved Request to Book reminders, and other product updates.

October 7, 202649 min

From Daily Admin to Scalable Operations with DenverStays and Chekin

On this episode of the Hospitable Hosts podcast, we are joined by our partner Chekin, an automated guest check-in platform, and Manuel Vicente, Founder of DenverStays.co and a short-term rental host. Manuel shares his journey managing short-term rentals in Denver, as well as across the US and Europe, highlighting how automation and compliance tools like Hospitable and Chekin have transformed his operations. He discusses strategies for scaling, managing legal complexities, and optimizing guest experiences without being physically present at each property. For more information, visit: https://chekin.com/ and https://denverstays.co/ Timestamps: 0:00 - Introduction 2:23 - Managing properties in multiple locations 4:58 - Pre-automation challenges in rental management 7:02 - Starting to use Chekin 10:50 - The impact of automation on operations 15:50 - Automation process outline 25:14 - Direct booking and marketing strategies 30:50 - European regulation updates and compliance tips 34:25 - Managing properties across time zones 42:00 - Future trends in the short-term rental industry 45:10 - Advice on scaling your property portfolio

October 1, 20261 hr 2 min

Product Updates - Hospitable Town Hall, September 30, 2026

At this Hospitable Town Hall, the team covered several key updates, including the new bank account matching feature for owners that connects existing bank accounts to owner profiles for easier payout management, Vrbo's planned pricing changes effective October 29th that will consolidate fees to 12% for both partner and legacy connections, and improvements to the Task app including backup teammate assignment and new language support. The team also discussed updates to the guest portal, with added Wi-Fi details and trip insurance information, new partner integrations, and various platform improvements for Booking.com and Vrbo connections.

September 23, 202619 min

Understanding Trust Accounting for Short-Term Rental Businesses with Clearing

On this episode of the Hospitable Hosts podcast, we sat down with Ashley Hagel, the Customer Success Manager at Clearing. We discuss when property managers should move from spreadsheets to dedicated trust accounting software, the importance of compliance, and how automation can streamline financial reporting. For more information, go to: https://www.getclearing.co/ Timestamps: 0:00 - Introduction 0:44 - When does a host need trust accounting software 3:17 - Understanding trust accounting and compliance risks 5:30 - Common mistakes in owner reporting and audit challenges 7:06 - How Clearing automates trust accounting for property managers 10:50 - How to tell you've outgrown your setup 13:52 - Hospitable x Clearing integration 16:05 - Preparing infrastructure for scaling to 100 units

September 17, 20261 hr 0 min

Split Owner Payouts - Hospitable Town Hall, September 16, 2026

On this Hospitable Town Hall, the team announced the launch of Split Payouts, a new feature that allows property managers to automatically split payments with property owners on Direct Premium and Vrbo Partner Connection reservations. The team explained the history and technical foundation that made this feature possible, including Hospitable's role as a merchant of record and its tax remittance capabilities. Hospitable also provided updates on the Vrbo Partner Connection, the Tasks app, and the Home Dashboard, highlighting new features and improvements.

September 9, 202645 min

The Essential Role of Short-Term Rental Advocacy

This is a slightly different episode of the Hospitable Hosts podcast, where we delved into a very important topic: short-term rental advocacy. Our guests are representatives from the Right to Rent Collaborative, Florida Alliance for Vacation Rentals, and Colorado Short-Term Rental Association. We explore the often overlooked, yet vital role of advocacy organizations in shaping the future of short-term rentals across the US, the efforts of various state associations, their challenges, and the importance of community and professionalization in the short-term rental industry. For more information, visit: https://r2rcollaborative.org/ https://floridaavr.org/ https://coloradostra.org/ Timestamps: 0:00 - Introduction 3:55 - Right to Rent Collaborative 9:50 - STR advocacy in Florida 13:32 - STR advocacy in Colorado 16:00 - The importance of advocacy 21:05 - How Right to Rent Collaborative's grants work 24:45 - How the grants are used in Colorado 26:23 - How hosts can contribute to the Right to Rent Collaborative and local associations 32:00 - How the $1/stay contributions help FAVR 33:40 - How the $1/stay contributions help COSTRA 36:00 - Future trends in STR advocacy

September 3, 20261 hr 7 min

Product Updates - Hospitable Town Hall, September 2, 2026

At this Hospitable Town Hall, the team provided updates on the Task App, announcing its expansion to Portuguese language support. Hospitable shared updates on the Owner Portal, including new controls for sharing private guest feedback with owners, and the new Home Dashboard.

August 26, 202621 min

Building a Resilient Short-Term Rental Business with Hospitable Hosts

In this episode of the Hospitable Hosts podcast, our guest is Eli Stoughton, the owner of Lahaina Studio. Eli shares his extensive experience in short-term rentals, lessons learned from wildfire impacts, and how AI and multi-channel strategies are shaping his business. Discover practical insights on insurance, platform diversification, and leveraging AI tools like Hospitable MCP. For more information: https://lahainastudio.com/ Timestamps: 0:00 - Introduction to Eli and his hosting journey 1:21 - Eli's background and entry into short-term rentals 2:26 - Eli's involvement in the Hospitable community 4:01 - Lessons from wildfire impact and insurance strategies 6:21 - Expanding to Booking.com and Vrbo: Why diversify? 9:33 - Managing complexity with Hospitable software 10:51 - Differences in guest demographics across OTAs 12:19 - Tips for new hosts on Booking.com and Vrbo 14:53 - Understanding Hospitable MCP integration and AI 17:42 - AI's potential to transform property management 20:17 - Goals for Eli's rental business in the coming year

August 20, 20261 hr 7 min

The New Home Dashboard - Hospitable Town Hall, August 19, 2026

At this Hospitable Town Hall, the team introduced the new Home Dashboard, which prioritizes critical issues, daily operations, and growth opportunities for hosts. Hospitable explained how the dashboard now surfaces urgent alerts, highlights exceptions in check-ins, checkouts, and tasks, and recommends relevant features based on account data. The session also covered other product updates, including MCP, the guest portal, thermostats, and more.