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The Insider: Steve Barsh on 5-Star Experience and Success with Direct Bookings

  • October 21, 2025
  • 16 replies
  • 321 views
Petra Podobnik
Hospitable Team Member
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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 Steve

Steve Barsh is the founder of Parker Chase Properties, a boutique collection of ultra-luxury, ski-in/ski-out vacation homes in Park City, Utah. For over 20 years, Steve has personally designed, owned, and managed each residence to deliver a private hospitality experience that rivals world-class brands like the Four Seasons, Ritz-Carlton, and St. Regis. Every detail—from architecture and amenities to service and guest care—reflects his commitment to creating unforgettable, five-star stays.

Beyond hospitality, Steve is also a Venture Partner at Inception, advising pioneering AI startups, and a former NASA advisor and Wharton lecturer known for his ability to blend innovation, execution, and excellence across industries.

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16 replies

NickG
New Participant
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  • New Participant
  • October 22, 2025

What is the highest ROI activity or money spent for someone just building out their direct booking channel? In an ultra competitive market like Nashville, it’s becoming increasingly hard to stand out on Airbnb and VRBO. 
 


CozyRetreats
New Participant
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  • New Participant
  • October 22, 2025

What does your week look like in terms of the activities you consistently do that drives direct booking numbers? How much of your direct booking strategy is based on organic activity such as posting in groups vs running targeted ads?


Miles Hobson
Hospitable Team Member
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  • Hospitable Team Member
  • October 24, 2025

How did you make that initial decision to go after the ultra-luxury segment vs budget friendly? You’ve clearly made that firm decision early on and really leaned into that - interested to know how easy of a decision that was to make and if you might approach it differently in a different market.


LittleNorwayPA
New Participant
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  • New Participant
  • October 25, 2025

What actions do you take and what messaging do you put out to potential guests to increase their trust in direct booking?  I receive a fair deal of traffic to my direct booking site, but I suspect that customers are still choosing to book through Airbnb rather than my direct site due to trust in the brand.  What type of messaging might you suggest to both 1) educate your customers on the direct booking process and 2) build their trust in your brand?


TheLibrarian
Known Participant
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  • Known Participant
  • October 29, 2025

You’ve clearly built an impressive brand with a strong direct booking presence. I’d love to know more about your social media strategy. What platforms (Instagram, TikTok, Facebook, etc.) have been most effective for you in driving awareness and trust? Who does your marketing for you? Also, do most of your direct booking guests first discover you through Airbnb or Vrbo before transitioning to book directly, or are they finding you through other channels? How do you convert them to book directly w/ you?


Petra Podobnik
Hospitable Team Member
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  • Author
  • Hospitable Team Member
  • October 29, 2025

For those curious: Steve was a guest on the Hospitable Hosts Podcast two years ago. Head over to check out the episode: The 5 Most Underappreciated Aspects to Maximizing Vacation Rental ROI 

 


fazel.wassim
New Participant
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  • New Participant
  • October 29, 2025

Beautiful site—really clean and well done! Quick question: is this built with Hospitable Direct or another platform? If it’s Hospitable Direct, how are Apple Pay, Google Pay, and standard card payments enabled? I thought Hospitable uses Stripe only—are those wallets just enabled through Stripe, or is there an additional payment setup?


Petra Podobnik
Hospitable Team Member
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  • Author
  • Hospitable Team Member
  • October 30, 2025

Welcome everyone to this special Insider session! 💜 This one’s special as for the first time, we’re welcoming one of you in the spotlight, and in a slightly different format.

Right now, ​@SteveBarsh  — Hospitable Host, investor, and industry expert — is on a video call with ​@Miles Hobson from the Hospitable team, answering your questions.

Thank you to everyone who submitted questions in advance, they’re great! We’ll share Steve’s replies here soon, once the recording goes through a quick edit, so keep an eye out and check back in this thread once they’re posted.


Miles Hobson
Hospitable Team Member
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  • Hospitable Team Member
  • October 30, 2025

What is the highest ROI activity or money spent for someone just building out their direct booking channel? In an ultra competitive market like Nashville, it’s becoming increasingly hard to stand out on Airbnb and VRBO. 
 

 


Miles Hobson
Hospitable Team Member
Forum|alt.badge.img+2
  • Hospitable Team Member
  • October 30, 2025

What does your week look like in terms of the activities you consistently do that drives direct booking numbers? How much of your direct booking strategy is based on organic activity such as posting in groups vs running targeted ads?


Looking for more tips on how others are driving direct bookings? Check out our recent podcast episode with Damian Sheridan.

Damian points out that social media and your direct booking website are the channels where you can express yourself and tell your story. You should use social media not just to promote your property and offer deals, but to post engaging content and interact with potential guests.

“On social media, we shouldn't be just a pure sales hit every time you make a post. We've a great property; you should stay there. That’s not of interest to anyone. We need to engage them. We need to be like the local expert on Facebook groups and on creating really engaging videos, for example, on Instagram. There are a lot of things that can be done there.”

Listen to the full episode of the Hospitable Hosts podcast to get actionable insights from another short-term rental expert.


Miles Hobson
Hospitable Team Member
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  • Hospitable Team Member
  • October 30, 2025

How did you make that initial decision to go after the ultra-luxury segment vs budget friendly? You’ve clearly made that firm decision early on and really leaned into that - interested to know how easy of a decision that was to make and if you might approach it differently in a different market.

 


Miles Hobson
Hospitable Team Member
Forum|alt.badge.img+2
  • Hospitable Team Member
  • October 30, 2025

What actions do you take and what messaging do you put out to potential guests to increase their trust in direct booking?  I receive a fair deal of traffic to my direct booking site, but I suspect that customers are still choosing to book through Airbnb rather than my direct site due to trust in the brand.  What type of messaging might you suggest to both 1) educate your customers on the direct booking process and 2) build their trust in your brand?

 


Miles Hobson
Hospitable Team Member
Forum|alt.badge.img+2
  • Hospitable Team Member
  • October 30, 2025

You’ve clearly built an impressive brand with a strong direct booking presence. I’d love to know more about your social media strategy. What platforms (Instagram, TikTok, Facebook, etc.) have been most effective for you in driving awareness and trust? Who does your marketing for you? Also, do most of your direct booking guests first discover you through Airbnb or Vrbo before transitioning to book directly, or are they finding you through other channels? How do you convert them to book directly w/ you?

 


Miles Hobson
Hospitable Team Member
Forum|alt.badge.img+2
  • Hospitable Team Member
  • October 30, 2025

Beautiful site—really clean and well done! Quick question: is this built with Hospitable Direct or another platform? If it’s Hospitable Direct, how are Apple Pay, Google Pay, and standard card payments enabled? I thought Hospitable uses Stripe only—are those wallets just enabled through Stripe, or is there an additional payment setup?

Hey ​@fazel.wassim, Steve adds some context in the video but the reason he has those options is due to him using Hospitable Direct Premium (currently only available in the US, UK, and Australia) where Hospitable is the merchant of record and handling payment processing and any chargeback disputes, as well as adding $5 million damage protection to every booking, and guest vetting. You can find out more about the difference in Direct plans here >

 


Miles Hobson
Hospitable Team Member
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  • Hospitable Team Member
  • October 30, 2025

And that’s a wrap on all the answers to your questions! If you have any follow-ups off the back of Steve’s answers, please add them to the thread and we’ll try to get more insight from Steve when he has a chance to shoot us some replies 😄

The Hospitable team is also here as always to answer any queries you might have 👋


Petra Podobnik
Hospitable Team Member
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  • Author
  • Hospitable Team Member
  • November 4, 2025

Here’s a quick recap of the conversation. Thanks again, ​@SteveBarsh, for taking the time to share your experience and insights. 💜