Send us a message!

The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet.

In this episode, we are joined by John Suzuki, Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental technology, the pace of innovation, and what this next chapter could mean for property managers.

John brings a long-term perspective on how far the industry has come, along with a thoughtful look at where it may be headed as AI becomes more deeply connected to the way operators work, serve guests, and build their businesses.

Episode Chapters:

02:46 - John’s 20-Year Journey in the Vacation Rental Industry

03:31 - How Vacation Rentals Moved From Phone and Fax Reservations Into the Mainstream of Travel

04:47 - Why John Came Back to the Industry After Retiring

09:20 - How AI Is Changing Property Management Technology

10:53 - Why Property Managers Need Systems That Help Them Move Faster

21:22 - The Importance of Connected Operations, Accounting, Reservations, Housekeeping, Maintenance, and Guest Communication

27:17 - How AI Can Support Call Tracking, Reservation Inquiries, and Guest Service

28:43 - Why Guest Data Will Play a Bigger Role in Travel Personalization

35:06 - The Ethical and Security Questions Surrounding AI

42:54 - How Robotics Could Affect Hospitality, Housekeeping, and the Workforce

46:16 - Why Professionals Need to Stay Curious and Keep Learning

48:55 - How AI Can Help Property Managers Get Back to the Human Side of Hospitality

If you are trying to understand what AI means for the future of vacation rentals, this conversation offers both perspective and practical insight from someone who has seen the industry evolve through multiple waves of change.

Connect with John:

Website: https://www.johnsuzuki.com/

✨ Exclusive Offer to Alex & Annie Listeners:

Automate your short-term rental operations with Hospitable.

Start a 14-day free trial and get 25% off your bill for the first 6 months.

👉 Get started: https://hospitable.com/partners/alex-annie

Reach more guests across top travel sites with BookingPal.

Alex & Annie listeners get onboarding fees waived + 20% off the first two months.

👉 Get started: https://alex-and-annie-offer.bookingpal.com/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

#vacationrentals #shorttermrentals #ai

Send us a message!

In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered.

This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people?

For many vacation rental operators, marketing often defaults to the property itself. A home needs bookings, a calendar has gaps, or a listing needs more visibility, so the message becomes centered around the unit. While property marketing still has a place, Orlie explains why stronger results often come from understanding the guest first.

That means looking beyond the booking and thinking about who the guest is, why they are traveling, what they care about, and how operators can use that information to create more relevant communication.

The conversation also explores why guest data is only valuable when operators can actually use it. Orlie breaks down how Lasoh is building a guest marketing system that helps operators collect, organize, and activate guest data through AI-supported campaigns, smarter segmentation, and more personalized messaging.

Instead of expecting teams to manually sort through data, build every campaign from scratch, and figure out what message should go to which guest, Lasoh is working to make that process more accessible. The goal is to help operators create more meaningful marketing, drive repeat bookings, and grow revenue without adding more pressure to already busy teams.

Episode Chapters

01:16 - Stop marketing properties and start marketing to people

01:41 - Why guest-first marketing needs better data

03:53 - Property management systems vs. guest marketing systems

06:47 - Turning guest data into action with Lasoh

08:24 - Using AI to create revenue-driving campaigns

12:28 - Smarter segmentation and fewer, better emails

15:54 - How AI agents support vacation rental marketing

18:40 - Saving time and growing revenue without adding more work

23:42 - One-to-all, one-to-some, and one-to-one marketing

26:44 - Lasoh’s founding member program

30:35 - What founding members can expect

This episode is a valuable listen for anyone thinking about how to make vacation rental marketing more relevant, more efficient, and more connected to the people behind each stay.

Learn more about Lasoh:

Website: https://lasoh.io/
LinkedIn: https://www.linkedin.com/company/lasoh/
Facebook: https://www.facebook.com/people/Lasohio/61575721958679/
Instagram: https://www.instagram.com/lasoh.io

Connect with Orlie:

LinkedIn: https://www.linkedin.com/in/orliebenjamin/
Facebook: https://www.facebook.com/profile.php?id=61585160391720
Instagram: https://www.instagram.com/orlie.benjamin/

✨ Exclusive Offer to Alex & Annie Listeners:

Turn every guest interaction into more revenue with Lasoh.

Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through July 31, 2026.

👉 Learn more: https://explore.lasoh.io/alex-annie

#vacationrentals #vacationrentalmarketing #directbookings

Send us a message!

In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations.

James shares how InvitedHome evolved from a broader multi-market vacation rental company into a luxury brand focused on ski markets. After operating across different types of destinations, the company made the decision to narrow its focus and go deeper in the markets where it could build stronger operations, deeper owner relationships, and more consistent guest experiences.

That shift became one of the central themes of the conversation: bigger is not always better. James explains why going deeper in the right markets can be stronger than expanding everywhere at once, and why sustainable growth requires the right homes, the right owners, strong teams, and the operational discipline to support the experience being promised.

Episode Chapters:

04:00 - Choosing Focus Over Footprint

05:39 - The Challenge of Scaling Luxury Vacation Rentals

16:59 - Working with the Right Owners

20:04 - What Consistency Means in Luxury

21:32 - AI, Technology, and High-Touch Service

27:36 - Direct Bookings and Luxury Travel Advisors

39:22 - Regulation in Ski Markets

46:12 - Why Undercharging Can Hurt the Business

Connect with James:

LinkedIn: https://www.linkedin.com/in/jamesalansmith/

Connect with InvitedHome:

Website: https://invitedhome.com

Instagram: https://www.instagram.com/invitedhome/

Facebook: https://www.facebook.com/InvitedHome

LinkedIn: https://www.linkedin.com/company/invitedhome/

✨ Exclusive Offer to Alex & Annie Listeners:

Automate your short-term rental operations with Hospitable.

Start a 14-day free trial and get 25% off your bill for the first 6 months.

👉 Get started: https://hospitable.com/partners/alex-annie

Reach more guests across top travel sites with BookingPal.

Alex & Annie listeners get onboarding fees waived + 20% off the first two months.

👉 Get started: https://alex-and-annie-offer.bookingpal.com/

#vacationrentals #shorttermrentals #skimarkets