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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

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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

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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

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In this episode, we are joined by Paul Wohlford and Amanda Szubert of Call Center Solutions to talk about staffing, guest services, AI, and the growing need for reliable support in vacation rental operations.

Paul and Amanda share how Call Center Solutions grew out of a real hospitality staffing challenge and how their nearshore team in Montego Bay, Jamaica now supports vacation rental and hotel companies with reservations, outbound calls, after-hours support, back-office work, and more.

The conversation also explores why human connection still plays such an important role in hospitality, even as AI becomes a bigger part of guest communication. Paul and Amanda break down how operators can use technology to support their teams while still creating the kind of guest experience that builds trust, drives bookings, and keeps people coming back.

We discuss:

05:59 - How Call Center Solutions got its start in the hospitality space

05:59 - Why staffing continues to be a challenge for reservation and guest service teams

12:00 - How nearshore support can help operators improve consistency and coverage

10:20 - The role of redundancy during storms, outages, and operational disruptions

14:40 - Where AI fits into guest communication and agent support

16:01 - Why human connection still matters in vacation rental hospitality

13:20 - The importance of training, knowledge bases, and quality assurance

44:41 - How support teams can help identify gaps in the booking experience

28:21 - What operators should consider when outsourcing guest services

Connect with CCS:

Website Link: https://www.ccssuccess.com/

LinkedIn Link: https://www.linkedin.com/company/my-call-center-solutions/

Facebook Link: https://www.facebook.com/ccssuccess

Instagram Link: https://www.instagram.com/call.center.solutions/

Connect with Paul:

Email: paulw@ccssuccess.com

Connect with Amanda:

LinkedIn: https://www.linkedin.com/in/amanda-szubert-8b26a033/

✨ Exclusive Offer to Alex & Annie Listeners:

Improve efficiency and customer engagement with Call Center Solutions.

Get all setup and implementation fees waived when you let them know you heard about CCS from Alex & Annie.

👉 Get started: https://www.ccssuccess.com/

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 #guestservices

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Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there.

In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools.

Chris shares what he has learned from nearly two decades in property management and how his experience as an operator led to the creation of Direct Booking Tools.

Through his own property management experience, Chris saw how important it is for guests to clearly understand the value of booking direct at the moment they are making a decision. Operators may know that value, but it has to be visible, trustworthy, and easy for guests to act on.

We discuss:

00:06:13 - Why trust is central to direct booking conversion

00:09:43 - How price transparency can influence guest decisions

00:15:16 - What website traffic can reveal about booking behavior

00:28:12 - How operators can use data to improve pricing decisions

00:49:26 - Why direct booking strategy needs more than awareness

00:28:12 - How to strengthen conversations with owners using real data

00:42:31 - Why Chris believes quality and intentional growth still matter

Whether you are trying to increase direct bookings, improve website conversion, or better understand how guests are making booking decisions, this episode offers a practical look at what operators can do to turn more interest into revenue.

Connect with Chris:

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

Website: https://directbookingtools.com/

✨ Exclusive Offer to Alex & Annie Listeners:

Strengthen your direct booking strategy with Direct Booking Tools.

Alex & Annie listeners get 50% off for the first 3 months.

👉 Get started: https://directbookingtools.com/alex-annie-landing-page/

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/

Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.

👉 Access the offer here: https://explore.lasoh.io/alex-annie

#vacationrentals #shorttermrentals #directbookings

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In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.

Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value.

The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and create value beyond the initial sale or stay.

Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.

Episode Chapters:

02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide

10:06 - How Marriott Vacations Worldwide thinks about loyalty

11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings

18:53 - What vacation rental operators can learn from timeshare

19:30 - How brand standards help build guest trust

28:20 - Why lifetime value matters in the customer journey

29:00 - Viewing vacation ownership as a subscription business

31:09 - Using experiences to strengthen loyalty and engagement

40:11 - How Marriott Vacations Worldwide is using AI in sales training

41:41 - How AI is changing digital search and hospitality marketing

47:52 - Why prepaid vacations create resilience

51:43 - What is ahead for Marriott Vacations Worldwide

Connect with Mike:

LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094

Instagram: https://www.instagram.com/thevacationdr/reels/

Connect with Marriott Vacations Worldwide:

Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/

Westin Vacation Club: https://www.instagram.com/westinvacationclub/

Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/

✨ 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/

Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.

👉 Access the offer here: https://explore.lasoh.io/alex-annie

#vacationrentals #shorttermrentals #timeshare

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Revenue strategy does not happen on autopilot.

Markets shift, booking windows move, owners ask harder questions, and guests become more price sensitive. For vacation rental managers, the strategy that worked last month may need a second look today.

That is the focus of Revenue Reality Check, a 6-part bimonthly series brought to you by Beyond. Each episode takes a closer look at the pricing decisions, demand trends, owner conversations, and revenue moves property managers should be paying attention to right now.

For the first episode, Alex & Annie are joined by Julie Brinkman, CEO of Beyond, to talk about one of the biggest topics in revenue management today: AI.

Julie shares how AI is already helping operators make sense of large amounts of data, reduce repetitive work, and give revenue managers more time to focus on strategy. She also explains why human oversight still matters, especially when it comes to pricing decisions, owner communication, and the revenue line of the business. For Julie, the opportunity is in using AI to support stronger decisions while keeping operators involved in the strategy.

We discuss:

00:37 - Why revenue strategy needs regular review

03:01 - How AI is being used in vacation rental revenue management

08:39 - Where automation can help reduce repetitive work

11:12 - Why owner communication needs market context

19:21 - How AI may affect OTAs, direct bookings, and listing visibility

28:22 - Julie’s Stop, Start, and Scale advice for using AI thoughtfully

31:43 - What operators should watch as World Cup demand develops

Tune in for the first episode of Revenue Reality Check, brought to you by Beyond, and follow along as we look at the trends, data, and revenue decisions vacation rental managers should be paying attention to now.

Connect with Julie:

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

Connect with Beyond:

Website: https://beyondpricing.com/

LinkedIn: https://www.linkedin.com/company/beyond-pricing/

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

Facebook: https://www.linkedin.com/company/beyond-pricing/

#vacationrentals #shorttermrentals #strindustry

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In this episode, Alex & Annie sit down with Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about the evolution of vacation rental software and why adoption across the industry still has so much room to grow.

Pierre-Camille shares how his own experience as an Airbnb host in Brussels led to the creation of Smartbnb, which later became Hospitable. What started as a solution for repetitive guest messaging has grown into a broader property management platform supporting communication, operations, channel management, direct bookings, payments, and more.

The conversation also explores why many hosts and operators still hesitate to adopt property management software, how Hospitable is working to make software more accessible, and what AI could mean for guest communication, support, direct bookings, and the future of vacation rental distribution.

In this episode, we discuss:

02:27 - How Pierre-Camille’s experience as an Airbnb host led to the creation of Hospitable

04:22 - Why guest messaging became the starting point for a larger software platform

09:45 - How Hospitable evolved from Smartbnb into a broader property management system

20:16 - Why software adoption remains low across parts of the short-term rental industry

21:55 - The challenges that keep smaller hosts and operators from adopting software

23:44 - Hospitable’s approach to making property management software more accessible

17:47 - How self-managers can grow into co-hosts or professional property managers

41:47 - The role of AI in guest messaging, customer support, and software usability

44:07 - Why AI should make tools easier to use, not simply add more complexity

53:07 - What AI agents could mean for OTAs, direct bookings, and property discovery

53:07 - Why strong owner service, guest experience, and operational consistency still matter as technology evolves

Connect with Pierre-Camille:

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

Connect with Hospitable:

Website: https://hospitable.com/partners/alex-annie

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

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

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

✨ 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/

Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.

👉 Access the offer here: https://explore.lasoh.io/alex-annie

#vacationrentals #shorttermrentals #pms