Hospitable Hosts

Hosted by Hospitable

Business Entrepreneurship

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Episodes

153

Latest episode

Jun 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

June 16, 202624 min

Long-Term Vision for Short-Term Rentals

On this episode of the Hospitable Hosts podcast, our guest is Christopher John, a Hospitable Host.Christopher shares his journey from real estate investing to successful short-term rentals in Seattle, including strategies for pricing, guest experience, and leveraging technology during major events like the FIFA World Cup.Timestamps:0:10 - Introduction2:30 - Starting out with short-term rentals6:21 - Getting into the business long-term8:18 - World Cup impact on short-term rentals11:56 - Enhancing guest experiences15:00 - Lessons learned19:15 - Advice for getting started

June 11, 20261 hr 28 min

Vrbo Partner Connection - Hospitable Town Hall, June 10, 2026

On this Hospitable Town Hall, the company launched their new Vrbo Partner Connection. It's built on Vrbo's latest APIs and offers self-serve onboarding, faster connection speeds, and better reliability compared to the previous legacy connection used by most hosts. The integration is available across 44 countries on day one, including the United States, Europe, Mexico, Brazil, and Asia Pacific regions. Key features include fully integrated listing management from within Hospitable, payment terms with installment options, and the ability to set Vrbo discounts and promotions directly through the platform. Hospitable also announced its merchant-of-record capabilities for Vrbo payments in the US, UK, and Australia, where it will process payments, handle taxes and chargebacks, and provide chargeback protection.

June 2, 202626 min

Financial Management for Short-Term Rentals with Topkey

On this episode of the Hospitable Hosts podcast, our guest is Jonathan Sukhia, CEO of Topkey. Jonathan shares insights on expense management, trust accounting, and financial automation for short-term rental operators. Discover how to streamline your financial processes, avoid common pitfalls, and scale your business effectively.Timestamps:0:00 - Introduction1:50 - Why Topkey was created7:53 - The importance of financial management11:25 - Understanding trust accounting15:06 - Keeping STR accounting organized17:43 - Integration with Hospitable

May 28, 20261 hr 6 min

Product Updates - Hospitable Town Hall, May 27, 2026

This Hospitable Town Hall covered various product updates, including the launch of Optimize for Airbnb, updates to the MCP (AI integration) server, recent improvements to app performance, particularly in inbox load times, Vrbo official integration, and more.

May 19, 202620 min

Remodeling and Designing High-Performing Short-Term Rentals with STR Cribs

On this episode of the Hospitable Hosts podcast, our guest is Mark Lumpkin from STR Cribs.Mark shares expert insights on transforming properties into profitable short-term rentals, covering renovation timelines, red flags, design strategies, ROI, and guest experience enhancements.Connect with Mark on Linkedin.Timestamps:0:10 - Introduction2:10 - Preparing a house for short-term renting3:45 - Property red flags5:56 - Designing a lasting property8:10 - Maximizing ROI10:33 - Creating a memorable guest experience15:40 - Adding small upgrades on a budget18:05 - Avoiding costly mistakes

May 14, 20261 hr 2 min

Product Updates - Hospitable Town Hall, May 13, 2026

This Hospitable Town Hall covered company updates following their recent retreat in Montenegro and new product features.Key product updates included Hospitable MCP (Machine Learning Connect Platform), which allows integration with AI agents like ChatGPT; improvements to the Tasks app with a new list view and upsell displays; and updates to the Vrbo official integration, launching June 10th.

May 5, 202626 min

The Secret to a 65% Repeat Booking Rate with Encinitas Bungalows

On this episode of the Hospitable Hosts podcast, we’re talking to Keith Clarke, a San Diego-based host who has unlocked the secret to repeat business. With 10 properties in Encinitas and a 65% repeat-guest rate, Keith is here to tell us why he still prioritizes personal check-ins, why he never charges for an early check-out, and how treating people like individuals, not line items, is the ultimate growth strategy.Check out http://encinitasbungalows.com/Timestamps:0:10 - Getting started with the short-term rental business8:34 - Screening guests in person12:46 - Property portfolio15:11 - Getting repeat bookings22:00 - Solving business challenges

April 30, 20261 hr 7 min

Hospitable Property Insurance - Hospitable Town Hall, April 29, 2026

This Hospitable Town Hall focused on the launch of Align Insurance Services, a new sister company that provides asset protection services, including owner's insurance, entity setup, and property management insurance for short-term rental operators. Other updates included the Model Context Protocol (MCP) integration, new payment schedule features for team management, improvements to the Vrbo integration waitlist, and enhancements to the Direct guest portal for payment history and receipts.

April 16, 20261 hr 4 min

Property Manager Marketplace - Hospitable Town Hall, April 15, 2026

This Hospitable Town Hall was dedicated to the new Property Manager Marketplace, a platform that connects property owners seeking management services with qualified property managers. The team presented the marketplace's features, explaining how it addresses the challenges both owners and managers face in finding trustworthy matches. The system uses a readiness-and-fit scoring system to match owners with suitable managers, providing detailed information about properties and owners' goals to help managers make informed decisions.

April 21, 202620 min

Building A Data-Driven, Personal, and Community-Centric Rental Business

In this episode of the Hospitable Hosts podcast, we chat with Cathleen Cataldo - founder of Discovered in Travels. Cathleen shares her unique approach to short-term rental management, blending fashion industry insights with hospitality. She discusses branding, personalized guest experiences, leveraging family expertise, and future growth strategies in the competitive Poconos market.Timestamps:0:00 - Introduction2:25 - Applying trend forecasting to short-term rentals3:35 - Branding for short-term rentals5:35 - Boutique company vs large establishment7:50 - Creating unique guest experiences11:35 - Running a family-owned property management business13:03 - Future plans17:35 - Rapid fire round