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A simple playbook for turning common guest requests into automated upsells.Many hosts focus on occupancy and nightly rates when trying to grow revenue. But there’s another opportunity hiding in plain sight: the extra things guests are already asking for.With Hospitable Upsells, guests can purchase add-ons like early check-in, late checkout, or amenities directly through the Guest Portal, without manual coordination or payment requests.Community member Matt McLean set this up across his properties and quickly turned those small requests into a smooth, automated workflow.Here’s how he did it; and what you can learn from it. Meet the hostMatt (​@mjm) currently hosts four properties in Southern California, including homes in Palm Springs and Big Bear. Two are his own properties, and two are managed for clients. He has been hosting for about six years, starting as a

We are getting ready to record our next Hospitable Hosts podcast episode, and we would love to feature some of your questions there as well!Our next guests are Alex Husner and Annie Holcombe - the hosts of a leading podcast for vacation rental professionals - Alex & Annie: The Real Women of Vacation Rentals. Alex is a seasoned vacation rental marketing expert with over 15 years of industry experience, who has played a key role as CMO in two enterprise vacation rental management companies in the United States, Condo-World and Casago. In early 2024, Alex left the corporate world to pursue her own initiatives as CEO/Founder of Directly Alex, a consultancy firm specializing in marketing and business growth strategies for vacation rental management companies and technology providers. Annie has 30+ years of experience in hospitality and tourism. She began her career in hot

We’re excited to host ​@Grace Gudenkauf, real estate investor, educator, and co-founder of Women Invest in Real Estate (WIIRE), for our next Insider session.Grace quit her engineering job in 2021 to go all-in on real estate and now owns and self-manages more than 25 units across eastern Iowa. As co-founder of WIIRE and author of The Self-Managing Landlord (BiggerPockets), she’s passionate about helping women gain financial freedom and confidence through real estate investing.💬 Ask Grace anything about investing, building wealth, and growing confidence as a self-managing host.Drop your questions in the comments anytime before the session. Or join us live on November 13 at 12pm ET, when Grace will be here answering directly in this thread.About WIIRE®

We are getting ready to record our next Hospitable Hosts podcast episode, and we would love to feature some of your questions there as well! Our next guest is Paul Stewart. ​@Paul of Cozy Cohost is the co-founder of Cozy Co-Host, a full-service short-term rental management company he runs with his wife, Ashley. Founded in 2020 in Atlantic City, Cozy Co-Host has grown from managing a single vacation home to overseeing more than 85 properties across the Jersey Shore—and even one in Florida. With a dedicated team of over 20 local professionals, Paul and Ashley provide end-to-end hosting services for property owners, handling everything from guest communication and design to maintenance and revenue management.If you have any questions or challenges that someone with Paul’s experience would be able to share some insights on, please c

We’re excited to welcome ​@SteveBarsh, Hospitable Host, investor, and industry expert, for our next Insider session.Steve has built a thriving luxury rental brand in Park City, Utah, and is now close to reaching $1 million in direct bookings. He’ll be available to answer your questions on strategies behind building trust with guests, delivering five-star experiences, and growing a direct channel that rivals the big platforms.💬 Ask Steve anything about direct bookings, brand building, and guest experience.Drop your questions in the comments! You have until Oct 30 at 9am PT / 12pm ET / 5pm CET. Steve will be replying a little later that day.About SteveSteve Barsh is the founder of Parker Chase Properties, a boutique collection of ultra-luxury, ski-in/ski-out va

We’re excited to welcome Emma Cole, Guest Experience Advisor at Touch Stay, for our next Insider: Partner Edition.Touch Stay is an all-in-one digital guidebook that helps property managers deliver a seamless guest experience, save time, and reduce guest questions. 💬 Ask Emma anything about guest experience, digital guidebooks, and practical ways to save time as a host. Drop your questions in the comments anytime before the session. Or join us live on October 16 at 12pm ET, when Emma will be here answering directly in this thread. Whether you’re new to guest guidebooks or looking to refine how you communicate with guests, join and learn directly from the team at Touch Stay.

We’re excited to host a special Insider session with ​@PC Hamana, founder and CEO of Hospitable.Pierre-Camille started Hospitable in 2016 to solve a problem he faced as a host himself: automating guest messaging for his rental. Since then, he has grown the company into a platform that empowers thousands of hosts to run their hosting business.To learn more about the $HOST token, watch the Town Hall (September 17), or check out the Investors Handbook.Ask Pierre-Camille anything about Hospitable, hosting, or the $HOST. Drop your questions in the comments ahead of time. Or join us live on October 2 at 12pm ET, when PC will be here answering d

We’re excited to bring you the next Insider session: Partner Edition with Arthur Colker, Founder and CEO of StayFi.StayFi is the leading provider of WiFi, marketing, and guest engagement tools for vacation rental operators. Used in more than 80,000 short-term rentals across 70+ countries, StayFi helps hosts increase profitability and guest loyalty by giving them access to something many OTAs keep out of reach: guest data.Arthur founded StayFi in 2018 to solve a core challenge in the industry: the lack of direct access to guest information. The company’s first product, branded WiFi, made it easy for operators to collect data from every guest in a booking, not just the person who made the reservation. Since then, StayFi has expanded into a suite of marketing and engagement solutions that help operators grow their direct bookings and strengthen guest relationships.Ask Arthur anything about WiFi, guest data, and the #BookDirect movement.How?

We’re excited to announce our very first The Insider conversation, the Ask me Anything series here in the Hospitable Community.In this series, we’ll shine a spotlight on inspiring hosts, partners, and Hospitable team members, giving you direct access to their stories, strategies, and insights.For our kickoff, we’re joined by ​@Abby Grous, Senior Product Manager for Hospitable Direct. Abby is on a mission to help hosts professionalize their direct booking offering, simplify the guest experience, and grow revenue; all with Hospitable’s powerful direct booking tools.Warm up with this podcast episode with Abby, where she shares how Hospitable Direct empowers hosts to reduce reliance on online travel agencies and take control of every stage of the guest journey.Now it’s your turn to ask Ab