Hospitable Masterclasses: STR Tips You Must Know in 2023


By The Hospitable Team

We know that being a short-term rental host can be like a game of Tetris… guests, bookings, and cleaning schedules are constantly falling from the sky and you have to fit them all together perfectly. 

To help our hosts slot everything into place, we organize Hospitable Masterclasses that are jam-packed with inspiration and insight. Invited industry experts cover a variety of topics to help you maximize your rental income and minimize your working hours, making it an all-around win-win situation.

And for those of you who missed any of the sessions last year or just want to have the recordings handy, we’ve now compiled all the best bits into this one convenient summary.

Mark Simpson (Boostly), Ela Mezhiborsky (Autohost), Sarah Karakaian and Annette Grant (Thanks for Visiting), Leo Walton (SUPERHOG), and Tony J. Robinson (Alpha Geek Capital) have already shared their secrets, tips, and tricks to make your short-term rental hosting journey a little bit smoother. All that’s left is to watch and learn. 

So, grab a cup of coffee and dive in as we bring you the insight highlights below, or jump straight to our all-in-one playlist to watch the full recordings. 

How to boost your direct bookings with Mark Simpson


Mark Simpson, the founder of Boostly and the author of The Book Direct Playbook, provided a whole set of guidelines on how to boost direct bookings as a short-term rental host. Mark shared his expertise on saving thousands in commission costs and building a hospitality business that is independent of third parties and is profitable. 

The so-called “Billboard Effect” became one of the highlights of Mark’s talk. This marketing strategy is used by hosts to make sure they are highly visible on various media platforms. Mark emphasized that a significant part of direct booking success lies in being present online when people start to think about their new travels. The idea is to be top of your guests’ minds when they are ready to book a stay. 

“The reason why we post online, the reason why we send an email, the reason why we do anything is that when the guest is at that booking stage, they think of you.” 

Curious to learn more from Mark Simpson? Watch our full Masterclass here

Mistakes to avoid when screening short-term tenants with Ela Mezhiborsky


Ela Mezhiborsky, Co-Founder and CPO of Autohost, shared her vision of a successful guest screening strategy. Ela discussed the guest screening as a part of quality assurance of the vacation rental experience for both guests and hosts, as well as the dangers of personal bias and discrimination in the screening process. She also provided practical tips for what hosts can ask their guests during the screening process and highlighted privacy and data protection aspects. 

Ela also focused on the differences in incentives between using an OTA like Airbnb or Vrbo versus using a direct booking website. Expanding the topic, the Masterclass provided a brief overview of the Direct Booking solution by Hospitable.com, which includes a payment processing mechanism, Autohost’s guest screening service, and insurance for property damages caused by guests.

“We want to move away from you looking at your guests, saying ‘They look sketchy.’ Because ‘sketchy’ is not a parameter. Guest screening has quite a lot of data points that are not so much about who the guests are but rather what their intention is. Are they being honest about their identity? Can you collect enough information in case something happens? And so on.” 

Curious to learn more from Ela Mezhiborsky? Watch our full Masterclass here

How to beautify your listings with Sarah Karakaian and Annette Grant 


Sarah Karakaian and Annette Grant of Thanks For Visiting showcased their expertise in designing, staging and operating short-term rental properties to attract more high-value bookings and increase revenue. Together, they covered topics such as tips for decorating and elevating the property, ideas for styling and picking the right interior design style, the importance of good photos, and understanding traveler behavior and preferences. 

The central theme of the Masterclass was offering maximum value for money by providing a seamless guest experience and personalization. Sarah and Annette made sure to provide a checklist for a 5-star guest experience and expanded our hosts’ toolkit with tips and tricks on each of the following points: 

  • Needs anticipation
  • Surprise and delight 
  • Enhancing the mood via design 

“The key to attracting high-value bookings is to make your property stand out and offer a unique and personalized experience for your guests.”

Curious to learn more from Sarah and Annette? Watch our full Masterclass here

Guest Screening & Damage Protection with Leo Walton


Leo Walton, Co-founder and VP of Growth at SUPERHOG, revealed his professional insights on how to effectively screen guests and prevent damage to short-term rental properties. The Masterclass focused on a truly insightful range of topics, including fraud within the short-term rental sector, the value of guest screening, balancing guest experience and security, and alternatives to traditional damage deposits.

Leo outlined SUPERHOG’s screening processes in detail, with a specific focus on party bookings and guest chargeback prevention. He stressed that the balance between guest experience and security is of particular importance for a successful short-term rental business. 

“If you are to give people the option between a traditional security deposit and a damage waiver, our research would suggest 85 of the time they’ll choose the waiver. Why? Because who needs the hassle of £500 coming out of their bank account? They’ll pay the waiver fee and they’ll forget they’ve even paid it by the time they arrive…but it’s there, you know it.”

Curious to learn more from Leo Walton? Watch our full Masterclass here

Tips & Tricks for Short-Term Rental Investments with Tony J. Robinson


Tony J. Robinson, the founder of Alpha Geek Capital, whom some of you may already know from The Real Estate Rookie podcast or The Real Estate Robinsons YouTube channel, shared his wisdom on how to succeed in the world of short-term rental investments. In our Masterclass, he discussed the importance of understanding the laws and regulations surrounding the market and explained how popularity is one of the most important characteristics to consider when making investment decisions.

Tony put a huge emphasis on having long-term partnerships, particularly in property investment and short-term rental industries. Becoming a “problem solver” yields great returns for your clients and a great business model for you, but how to find those lasting partnerships? Be vocal and consistent about what you do in your own media. 

“The sooner the investors realize that real estate is really about relationships, the sooner they’ll find success.”

Curious to learn more from Tony J. Robinson? Watch our full Masterclass here

More in 2023

Excited to see more webinars this year? 

Industry experts and pro-hosts will keep on sharing the best tips live and on our YouTube channel

Got inspired by all the exciting details of the hosting world and want to generate additional income without sacrificing your free time and energy? 

Streamline your short-term rental business!

Hospitable is here to support a world where short-term hosting is just as simple as long-term.

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