Alex and Annie: The Real Women of Vacation Rentals

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: [email protected]

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

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In this special episode, Alex and Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo’s Vacation Rentals of the Year program and what it takes to earn that recognition.

Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year’s winning properties, the episode offers both a platform perspective and a firsthand look at the kind of hospitality Vrbo is celebrating.

Tim shares how Vrbo selects winners from millions of properties across its global network, using a mix of performance data, guest reviews, local market insight, and hospitality storytelling to identify homes that deliver standout guest experiences.

The conversation then shifts to David Rose, owner of Lakefront Escape, who shares how he transformed a dated lake house into an award-winning retreat designed with intention, warmth, and usability in mind.

From intuitive in-home tech and thoughtful labels to tailored recommendations and architectural details, this episode highlights how exceptional hospitality is built through the details.

In this episode, we cover:

03:50 - Why Vrbo created the Vacation Rentals of the Year program
04:39 - How Vrbo selects its Vacation Rentals of the Year
08:04 - What makes a vacation rental experience feel personal and memorable
13:35 - Meet David Rose and the story behind Lakefront Escape
16:42 - Why intuitive technology matters more than flashy features
23:00 - How David Rose designed Lakefront Escape for connection, comfort, and discovery
25:20 - Why David chose self-management and how Vrbo supports pricing and promotion
26:43 - How personalized recommendations can elevate the guest stay
30:34 - How labels, notes, and in-home guidance reduce guest friction
32:21 - The Japanese design influence behind the home’s guest experience
35:27 - How design, layout, and local insight help create repeat guests

This episode captures both the criteria behind Vrbo’s recognition and the real-world hospitality choices that help a property earn it.

Connect with:

David Rose / Lakefront Escape
https://www.squamlakehouse.com/ 

Tim Rosolio / Vrbo
https://www.linkedin.com/in/tim-rosolio-434b2a98/ 

✨ 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 #vrbovacationrentalsoftheyear

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Not every guest stay ends with a five-star review.

Some leave behind a mess. Some turn into a serious operational headache. And some become the kind of story you end up telling for years.

That is the idea behind Pour Decisions: When Stays Go Sideways, a special series presented by Safely. 

In this series, Alex & Annie sit down with the Safely team and industry guests to unpack the kinds of guest incidents that rarely make it into the marketing copy but often leave the biggest operational impact. Through real stories, practical insight, and a little cocktail-fueled commiseration, the series explores what went wrong, how it was handled, and what operators can do to better protect their homes, teams, and owners.

About Episode 1:

In this kickoff episode, Alex & Annie are joined by Amanda Martins, Vice President of Business Development at Safely, to introduce the series and set the stage for the conversations ahead. Amanda shares what Safely sees behind the scenes when guest-related damage claims come in and why these stories can be some of the most useful lessons in the business.

The episode also dives into one recent case involving a large home that became the site of a 50-person party, complete with police involvement, extensive damage, smoke remediation, and a long list of cleanup issues. Amanda walks through what happened, the documentation that helped support the claim, and what operators should be thinking about when it comes to guest screening, damage protection, liability, and owner communication.

It is a practical conversation that sets the tone for the series ahead, showing how real guest incidents can reveal where systems hold up, where they fall short, and what operators can do to better protect their business before the next stay goes sideways.

In this episode:
01:41 - Meet Amanda Martins of Safely
03:34 - Why Alex & Annie launched this special series with Safely
08:34 - A real story involving a party that caused major property damage
15:01 - How Safely’s claims process works
16:31 - What happens if an operator does not have damage protection
19:01 - When operators should involve police or pursue legal action
24:06 - Why guest screening can help deter the wrong bookings
28:28 - Protecting homeowners and reducing business risk
30:20 - How Safely works alongside homeowner insurance
36:55 - Why this matters for operators of every size

Have a story to share?

We want to hear your worst guest stories. If you have a stay that went completely sideways and a lesson to go with it, submit it for a chance to be featured on a future episode.

Submit your story here: https://form.jotform.com/261032817700044

Connect with Amanda:

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

Learn more about Safely:

Website: https://safely.com/alex-and-annie 

LinkedIn: https://www.linkedin.com/company/safely-stay/ 

This episode’s cocktail: Checkout 75

A little classy, a little dangerous, and apparently best enjoyed seated.

Ingredients:

• 1 oz tequila
• 0.5 oz GranGala
• 0.5 oz fresh squeezed lime juice
• 0.5 oz fresh squeezed orange juice
• Sparkling wine, such as prosecco or a dry brut, to top

How to make it:

Shake the tequila, GranGala, lime juice, and orange juice with ice. Strain into your favorite wine glass, then top with bubbly.

Amanda’s final tip:
Don’t stand up too fast when finished.

#vacationrentals #shorttermrentals #guesthorrorstories

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What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place?

In this episode, we are joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through a model built on local leadership, shared support, and strong operational foundations.

Instead of forcing every market into the same mold, Awayday supports growth through shared resources across accounting, HR, revenue management, business development, and technology, while local teams continue to lead the day-to-day business. Jakob also shares how that approach influences the way Awayday evaluates partners, supports local operators, and balances growth with owner and guest experience.

This conversation offers a clear look at how Awayday is building scale through stronger operations and support without losing the local identity at the core of each business.

Episode Chapters:

00:00 - Intro to Awayday CEO Jakob Dwyer

01:14 - Jakob Dwyer’s background in vacation rentals and RealJoy’s growth

05:52 - How Awayday scales local vacation rental companies

10:50 - Why local market knowledge matters in vacation rental growth

13:07 - What Awayday looks for in a vacation rental partner

18:17 - Founder transitions, succession planning, and exit options

23:15 - Why strong vacation rental operations matter more than growth at all costs

27:01 - Awayday’s onboarding process and value creation strategy

31:41 - Shared services, local leadership, and centralized support

37:05 - How Awayday is thinking about AI in vacation rental operations

46:11 - SOPs, company culture, and empowering vacation rental teams

50:57 - Awayday’s growth strategy for 2026 and beyond

58:43 - Why every team member plays a role in company growth

This episode is brought to you by Awayday. If you are interested in being part of a company that values local leadership, strong operations, and long-term growth, connect with Jakob at [email protected].

Connect with Jakob:

LinkedIn: https://www.linkedin.com/in/jakob-dwyer-19516033/ 

Connect with Awayday:

Website: https://www.awayday.com/
LinkedIn: https://www.linkedin.com/company/awayday-vacation-rentals/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Streamline your short-term rental operations with Hostfully.

Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ 

Reach more guests across top travel sites with BookingPal.

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

👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/ 

#vacationrentals #shorttermrentals #localidentity

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We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing.

Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relationships with every guest.

Together, they explore what it really takes to build stronger guest relationships, improve direct booking performance, and think more strategically about marketing in vacation rentals.

In this first episode, Orlie shares the thinking behind Lasoh and the problem she believes the industry still has not solved. While many of the core systems in vacation rentals are designed to manage properties, pricing, and distribution, far fewer are built to help operators understand guests, strengthen relationships, and market in a way that creates long-term value.

The conversation looks at what happens when hospitality gets overshadowed by operations, why guest data matters far beyond the initial booking, and why marketing deserves a bigger role in growth strategy.

Episode Chapters:

01:56 - Why Orlie Benjamin built Lasoh for vacation rental marketing

04:19 - What’s missing from most vacation rental PMS platforms

07:58 - Vacation rental tech vs. hotel tech: where the gaps still exist

09:47 - Asset management vs. guest experience in hospitality

11:01 - Why hospitality gets harder to scale in vacation rentals

13:42 - Why revenue management and marketing should work together

16:33 - The real levers of growth: customers, spend, and repeat stays

21:03 - How Lasoh helps operators capture guest data and personalize marketing

25:46 - Guest-first marketing vs. inventory-first marketing

This episode sets the tone for the series ahead and offers a valuable perspective for anyone looking to build a more thoughtful, guest-centered marketing strategy.

✨ Exclusive offer for Alex & Annie listeners ✨

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

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

Valid through May 31, 2026.

Learn more about Lasoh:

Website: https://tinyurl.com/52nvyw8t
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/lasoh.io/

#vacationrentals #vacationrentalmarketing #directbookings

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