Alex and Annie: The Real Women of Vacation Rentals

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In this episode, we are joined by Ed Ulmer, CEO of Barefoot, for a conversation about trust accounting, vacation rental technology, and what operators need from their systems as their businesses become more complex. 
Ed shares how his background in tourism, destination marketing, real estate, and software all shaped the way he looks at vacation rental management today. For him, the industry has always come back to one core idea: trust. 
The conversation takes a deep dive into why trust accounting should not be treated as a back-office function. When vacation rental companies manage properties on behalf of owners, they are also managing funds, contracts, obligations, and expectations. As companies grow, that complexity only increases. 
Episode Chapters:
03:18 - Ed’s path from tourism, real estate, and software into vacation rental technology
11:56 - Why vacation rental management is built on trust
17:37 - What trust accounting really means for property managers
25:24 - Why managing owner and guest funds gets more complex as companies grow
27:27 - How state regulations and real estate requirements impact vacation rental operators
30:10 - Why loyalty programs are harder to build in vacation rentals than in hotels
33:48 - How PMS technology can support concierge services, rewards, and guest retention
39:17 - What operators should consider when choosing a PMS
47:55 - How AI and natural language search may change the booking experience
For operators evaluating their technology, this episode offers a practical look at why the systems behind the business matter just as much as the guest-facing experience. 
Connect with Ed & Barefoot:
LinkedIn: https://www.linkedin.com/in/ed-ulmer-150596/ 
Website: https://www.barefoot.com/ 
Facebook: https://www.facebook.com/mybarefoot 
✨ Exclusive Offer to Alex & Annie Listeners: 
Manage your vacation rental business with more control and confidence using Barefoot. Alex & Annie listeners get 10% off monthly fees through 2026.
👉 Get started: https://www.barefoot.com/alex-and-annie 
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/ 
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 #trustaccounting

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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