Alex and Annie: The Real Women of Vacation Rentals

In this episode, Alex and Annie are joined by Dora Du, CMO of WYND - venture-backed startup that has built proprietary sensor technology that helps homeowners take control of the air in their properties. Their first use case is a product line that monitors and improves in-door air quality, and more recently they’ve released a new product that detects noise and smoke.

WYND was founded by MIT engineers and scientists, with their first focus being to create products for the residential market. During COVID, they ventured into the vacation rental space unintentionally - but as more property managers bought their initial line of products, WYND followed the market and have now changed their messaging, approach and product development to be more tailored towards the vacation rental industry.

Dora highlights that WYND is playing their role in the automation revolution of the vacation rental industry. With new remote technology becoming more prevalent and the short term rental space being democratized with the Airbnb boom, there’s both excitement on the horizon, and also lots of added pressure with the rapid increase in regulations. They know their product line will become less of a “nice-to-have” and more of a “must-have” as HOA’s and local governments push for more regulations.

When comparing the vacation rental and hotel markets, Dora mentions that the biggest difference is the speed of adaptation and implementation. Selling to vacation rental property managers happens at a much lower volume and with a less complex sales cycle, which puts vacation rentals ahead of the curve in regards to new technology adaptation.

Dora goes into detail on how WYND is changing the game for sensor technology, and talks on the many use cases and proprietary value of their product line. They are now developing new AI technology to help people improve their indoor environment by better understanding the air they breathe - which is super exciting.

Tune in to the full episode to learn about new technology that might be a great addition to your vacation rentals!

HIGHLIGHTS
00:30 How WYND Found Product Market Fit
08:54 Dora’s Career Trajectory
11:22 The Difference Between Serving STR’s and Hotels
13:29 How COVID Kickstarted Vacation Rental Technology Adaptation
15:25 How WYND’s Technology Works
19:30 Dora’s A-HA Moment in Her Career
20:59 What’s Next for WYND

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech.

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Dora:
Website | Linkedin

Connect with Alex and Annie:
Alex Husner | Annie Holcombe
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On the August 1st of the Month Bonus Episode, Alex & Annie welcome the return of Simon Lehmann - CEO and Co-Founder of AJL Atelier, a boutique consultancy that specializes in the international private accommodation and vacation rental industry. The topic of today is the shifting landscape of the short term rental industry, and what the current situation is in different STR hotspots around the world.

Simon has a 360 view of the global vacation rental market, as both his consultancy and the clients he serves operate around the world. One of his insights is that international airfares have reached unprecedented levels, while domestic travel has taken a backseat. European economic downturns typically arrive with a delay compared to the US, so this ripple effect is expected to drive down international demand in 2024 and return domestic travel back to status quo.

Simon mentions that the current macroeconomic situation with interest rates hiking is making short term rental investments less attractive to investors. The increased cost of capital has even shaken up giants like Airbnb, causing them to decrease the exorbitant fees they had climbed up to over the last few years. 

This isn’t necessarily a bad thing for the industry. With less people treating short term rentals as a goldmine investment opportunity, truly professional operators will have a chance to shine in a less crowded market and regain the market share they possessed prior to the Airbnb boom.

The way Simon sees the market shaping is that professional operators are now having a resurgence, as the barrier of entry for a successful short term rental property manager is increasing. He sees professional hosts getting their market share back by integrating the right technology, having better accessibility through book direct vendors, and most importantly - fostering stronger long-term relationships with homeowners. 

The current downturn isn’t affecting every destination equally. The markets that are most damaged right now are 2nd and 3rd tier destinations, with real estate companies reporting unprecedented churn rates as newer operators that placed investments into short term rentals during the Airbnb rise of the last few years are now looking to unload their properties due to shrinking profits. 

Tune in to the full episode to learn how to navigate the market changes of 2023 and avert future crises!

HIGHLIGHTS
04:39 The Market Has Softened - What Now?
08:43 Which Markets are Most Affected in 2023
11:01 Cost of Living Crisis in Europe
13:24 Climate Crisis - What’s Next?
16:02 Simon’s View of The Bear Market
23:28 How Professional Operators are Increasing Their Market Share
25:45 Building Trust Through Transparency
31:02 Homeowner Generational Changes
33:45 Simon’s Message for the Remainder of 2023

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech.

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Simon:
Website | Linkedin

Connect with Alex and Annie:
Alex Husner | Annie Holcombe
AlexAndAnniePodcast.com

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In this episode, Alex and Annie are joined by Mike Reinman, Owner of Casago Kona & Owner/GM of Casago Redwood Coast. Mike sold Redwood Coast Vacation Rentals to Vacasa at the end of 2019. After speaking with Casago CEO Steve Schwab, Mike decided to return to the industry and purchase a STR business in Kona. This is where his partnership with Casago began, and what laid the foundation for his next venture with Casago Redwood Coast.

Mike started in the short-term rental industry by converting his garage into a rental space. He then managed to scale this business to a staggering 142 properties before ultimately selling and taking a sabbatical from property management.

During his time running Redwood Coast Vacation Rentals, Mike had been approached for a franchise opportunity with Casago, but he ended up going in a different direction. When Mike sold his first STR business, Steve Schwab approached him with the opportunity to purchase a vacation rental business in beautiful Kailua-Kona, Hawaii, and so their partnership began.

Mike attributes his decision to invest in Casago Kona to the support system that Casago brings to the table for their operators. He had experienced dissatisfaction with the previous software providers and booking vendors he had used, and those experiences made him doubtful of ever wanting to get involved in the vacation rental space again, given the struggle of ensuring operational soundness and profitability.

A big selling point for Mike was the community aspect of being a Casago business. Having the ability to confide in other vacation rental owners and get their expertise on how to better run a vacation rental business has been a game changer and brought many new insights to Mike’s already astute understanding of the vacation rental industry.

Mike’s appreciation for the way Casago works with their property managers didn’t appear from thin air. When he sold his first business to Vacasa, he wasn’t a huge fan of the corporate atmosphere. To be a successful property manager, you must have a broad understanding of various aspects of the business, and Mike didn’t feel like this was reflected in the conversations he had with members of the Vacasa team.

Tune into this episode of Alex & Annie to hear more insights on what a proper support system can do for your vacation rental business!

HIGHLIGHTS:
02:01 Mike’s Journey to California and the Inception of His STR Business
06:58 How Mike Started Evaluating His First Casago Project
10:25 The Struggles of Running a STR Business in Hawaii During COVID
11:34 How Casago’s Support System Closed Mike
15:17 Growing Together With Other Successful Property Managers
19:25 The Importance of Consistent Coaching
25:05 Mike’s Experience Working with Vacasa
27:42 Mike’s Approach to Leadership


This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech.

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Mike:
Website | Linkedin

Connect with Alex and Annie:
Alex Husner | Annie Holcombe

AlexAndAnniePodcast.com

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In this episode, Alex and Annie are joined by Alex Shapiro, CEO and Co-Founder of CanMonkey - the very first Trash-To-Curb Service that handles the waste and recycling can duties of your vacation rental properties.

CanMonkey started 4 years ago with a business model that’s similar to Uber and DoorDash - employing gig economy drivers to ensure a seamless service across 13 different states. What differentiates them from Uber’s business model is that they’ve achieved profitability as a bootstrapped startup, instead of relying on funding and burning through cash.

Before Alex made the decision to go all-in, he chose to first see CanMonkey drive results in their local market. Luckily, this market was Scottsdale, AZ - one of the most thriving markets in the rental property space. His A-HA moment was during a meeting with a client who was converting his long-term rental into a short-term rental and had expressed his frustration with his current waste management setup. This conversation unlocked a deal that effectively doubled their business overnight - and Alex knew it was time to fully bet on CanMonkey.

The way CanMonkey develops their service has been a key factor in their rapid growth. Alex has always approached product development with feedback and flexibility in mind, letting their clients be the ones who inspire their product strategy and ultimately choose how they’re best served.

Another key factor has been their sublime approach to marketing. During the conversation with Alex, it’s apparent that his wheels are always turning when it comes to new ways to market their business. His approach to finding relevant and fun ways to create social media content stems from conversations he has with clients, and the tidbits that come through during those interactions. He’s also not afraid of “poking the bear” and creating campaigns that might receive negative feedback, which can often be a phenomenal strategy to gain brand awareness through a tiny sprinkle of controversy. 

Tune in to the full episode to learn what it takes to successfully scale a service-based business!

HIGHLIGHTS:

01:30 - CanMonkey’s Go-To-Market Strategy
03:16 - The A-HA Moment that Led Alex to Going All-In
05:49 - CanMonkey’s Main Use Case
11:49 - Their Approach to Growth & Product Development
15:45 - Building Brand Awareness Through Clever Marketing
21:34 - Alex’s Roots in the Fortune 500
27:14 - The Advantages of Being Bootstrapped
31:26 - The Future of CanMonkey

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech.

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Alex:

Website | Linkedin

Connect with Alex and Annie:

Alex Husner | Annie Holcombe

AlexAndAnniePodcast.com

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In this special edition of our “Spotlight on Exceptional Property Managers'' series, presented by Casago, we sit down with Stacy Wesson of Casago Cascara Vacations. Stacy shares her stories and experience in the industry running the family business in Sun River, Oregon that joined forces with Casago in April of 2022.

The story of Casago Cascara Vacations for Stacy is one that begins in her early childhood. Her parents opened the business when she was only 5 years old, so she’s seen the evolution of every aspect of the business - and now holds the title of General Manager.

A little over a year ago, Stacy joined forces with Casago to help streamline the business operations of Cascara Vacations. After 10 years in the industry, Stacy was feeling a bit frustrated with how the local business scene had evolved. New players were arriving in their local market and bullying them with aggressive, high-roller tactics, so a decision was made to get external help. 

Now, she’s seeing huge improvements in aspects such as new technology implementation, vendor selection and competitive analysis. Being part of a community of vacation rental professionals that are all working towards a common goal has been a game changer for their business, and has led Casago Cascara Vacations to see more positive reviews, avoid turmoil with homeowners, and bring solidarity to their internal team through the positive impact seen in their day-to-day operations.

Check out the full episode to learn more tips & tricks on how to add efficiency and excellence to your vacation rental business!

HIGHLIGHTS:

02:30 Stacy’s Leadership Philosophy
06:42 Navigating Around Bad Regulations and Unhappy Campers
12:08 Stacy’s Strategy for Avoiding Future Turmoil
16:23 What Went Into Stacy’s Decision to Join Forces With Casago
20:58 The Changes in Casago Cascara Vacations Over the Last Year
25:18 Casago’s Onboarding & Support Process
30:10 The Impact of Proper Training and Support

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech. 

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services. 

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Stacy:

Website | Linkedin

Connect with Alex and Annie:

Alex Husner | Annie Holcombe

AlexAndAnniePodcast.com

Send us a message!

In this episode, Alex & Annie are joined by a panel of experts to help guide you on a pressing topic - How to Explain Changes in Revenue and Bookings to Your Homeowners.

2023 is not turning out to be as profitable as expected for vacation rental managers, and naturally this is causing quite a bit of turmoil for property managers, especially those who got into the business during the golden years of 2020-2022.

That’s why today's Revenue Roundtable features Ben Coleman - Founder of Rev & Research, Vanessa Humes - Director of Sales & Marketing at InterCoastal Net Designs and Lance Stitcher - Broker/Owner at Seaside Vacations and Sales.

Some of the great insights discussed in this episode includes proactive, data-driven communication with your homeowners, as well as the importance of making sure you’re pricing appropriately for 2023 instead of making decisions like it’s still last year.

Whether you’re an individual property manager feeling the pressure of the current market, or a Vacation Rental company with hundreds of properties under management looking to safeguard your book of business - tune in to this episode to learn from our expert panel on exactly what steps to take to navigate the stormy seas of 2023 and beyond.

HIGHLIGHTS:

00:00 Introducing Today’s Revenue Roundtable
02:24 Setting Today’s Agenda - Revenue is Down, What To Do?
04:30 How a Data-Driven Approach Is Becoming a Necessity in This Market
08:42 Proactive Account Management is a Necessity & Homeowner Marketing Becoming a Priority
13:25 The Value of a Strong Social Presence
14:52 More on Proactive, Data-Driven Communication, and the Importance of Staying Ahead of your Homeowner
19:10 Understanding Local Market Conditions and Pricing Accordingly
20:10 Lance’s Approach to Educating Homeowners About Market Conditions
22:13 How to Set Expectations for The Upcoming Fall Season
24:16 Creating Demand as a Marketing Focus Point
26:54 Data As The Ultimate Revenue Team Alignment Tool
30:52 Ben’s and Lance’s Approach to Channels
35:05 The Value of Proper Communication Within Your Team
36:16 What Topics are Currently Underrepresented within Revenue Teams
38:24 Lances Prediction on How Inventory Will Shift From Investments to Residential Properties
40:30 Bens Predictions on How The Markets are Changing and his Strategy to Navigate What’s Ahead
45:02 How To Get In Touch With Today's Experts

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech. 

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services. 

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Ben:

Website | Linkedin

Connect with Vanessa:
Website | Linkedin

Connect with Lance:
Website | Linkedin

Connect with Alex and Annie:

Alex Husner | Annie Holcombe

AlexAndAnniePodcast.com

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Welcome to Episode 101 of Alex & Annie: The Real Women of Vacation Rentals - the celebration of passing the 100-episode milestone.

Today, we are joined by Ed the Ghost Host, who's interviewing us about this wonderful journey we've been on since January 2021, and passing us the microphone so we can unveil some new projects and initiatives coming your way.

To start, we'd like to thank everyone who has come along for the ride - from our wonderful guests to our plentiful listeners and those who engage with us on social media.

We also appreciate those who aren't strangers when seeing us at vacation rental conventions and events. Your support, feedback, and communication mean a lot to us. It has been amazing so far, and there's so much more to come.

It's beyond wild that we've been heard tens of thousands of times across six different continents and in almost 30 countries. This was not at all what we expected when we started this podcast two and a half years ago.

So, what's next?

We're now in the process of writing our first book that will highlight the stories of our guests. It's a passion project we've been thinking about for a long time, and we believe it's time that we create something tangible to further shine a light on the wonders that have been revealed during these 100 episodes.

We are beyond excited.

One thing is very apparent in our industry - there's a divide between the short-term rental space and the vacation rental space, and we're not fans of that at all.

We believe that a unified voice between the two sectors should be the common goal. This will help both industries grow and avoid unwanted regulations, and we're dedicated to doing our part in bringing alignment between these two similar but different industries.

We have a list of guests that we would love you to hear from on our show, such as:

• Marcus Räder from Hostaway
• Ed Mylett
• Heather Monahan 
• Rob Greyber from Vacasa
• Bill Faeth
• Brian Chesky from AirBnB

This has been a really rewarding journey for both of us. Building our personal brands, beginning and nurturing new friendships, and hearing direct feedback from people we never thought were even listening to us. We're happy, grateful, humbled, and insanely excited for things to come.

Stay tuned!

00:00 Welcome to Episode 101 - The Celebration of Passing 100 Episodes
00:45 Our First “Thank You” of the Episode
01:34 Introducing our Guest Host
03:37 What’s next for Alex & Annie?

05:04 Book Announcement!!
08:29 New Narratives in the Upcoming Episodes
11:28 What can STR’s Learn From Our Industry and Vice Versa
14:28 Dream Guest List - What To Expect
19:05 The Most Rewarding Parts of Our Journey as Hosts
22:26 Another Thank You!!
 
This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech. 

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Alex and Annie:

Alex Husner | Annie Holcombe

AlexAndAnniePodcast.com

Send us a message!

In this very special anniversary episode, Alex & Annie are joined by Travis Wilburn and Rebecca Lombardo - Co-Founders of The 100 Collection.

The 100 Collection is a prestigious evaluation program that recognises exceptional vacation rentals managed by industry-leading companies committed to excellence in hospitality across a multitude of destinations.

Travis and Rebecca are huge believers in the value that local brands bring to the vacation rental space and the importance of a “Doyen/Doyenne” - meaning the most well respected and knowledgeable person in their particular space - as the term relates to the absolute best local vacation rental manager.

Their approach to adding new members to The 100 Collection is centered around finding the local Doyen/Doyenne. During this evaluation process, the highest esteemed and most trusted local hosts are curated and often unbeknownst to them enter a research and evaluation process to potentially become part of The 100 Collection. 

The 100 Collection is going live mid-July - so their guest-facing launch is right around the corner!

We highly suggest you follow their journey and take the lessons discussed in this episode to heart when building your vacation rental brand.

HIGHLIGHTS:

00:00 - Welcome to Episode 100!

00:50 - How Today’s Guests Started The 100 Collection 

02:25 - What is The 100 Collection?

04:22 - The Meaning of “Doyen”

06:43 - How The 100 Collection Evaluates New Members

09:15 - The Importance of a Professional Vacation Rental Host

11:47 - How They Find a Doyen/Doyenne

15:40 - Current 100 Collection Portfolio 

18:15 - The Value of The 100 Collection Brand & More On Their Evaluation Process

22:43 - How Customers Make Buying Choices & How To Develop a Trustworthy Brand

25:50 - When The 100 Collection is Going Live and Their Marketing Strategy

31:17 - What’s Next for The 100 Collection

34:43 - The 100 Collection Potentially Collaborating with VRMA

35:58 - The Story of The 100 Collection Brand

39:20 - A BIG Thank You to Our Fans!!

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech. 

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services. 

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Travis:

Website | Linkedin

Connect with Rebecca:
Website | Linkedin

Connect with Alex and Annie:

Alex Husner | Annie Holcombe

AlexAndAnniePodcast.com

Send us a message!

Welcome back to another exciting episode! Today, we have a special guest, Bart Sobies, who is an expert in vacation rentals and technology. Bart is the visionary behind The Accommodation Show and iBooked.Online. He has a long history of success, starting his first online business at just 15 years old. With his passion for technology, marketing, and investment, Bart has helped many hospitality owners generate extra revenue through direct bookings and digital products. He is also the founder of a thriving Facebook community where over 2000 industry professionals share valuable insights.

In this episode, Bart shares practical tips for building a successful website and using direct booking strategies. He draws from his experience in helping restaurants with online ordering to highlight the importance of adapting to changes and recognizing the potential of direct bookings in vacation rentals. As the host of The Accommodation Show, Bart explores how emerging technologies like AI and Chat GPT are shaping the future of the industry. He discusses their impact on thought leadership, provides valuable tips for using Chat GPT effectively, and explores their implications for SEO.

Additionally, Bart stresses the significance of building a brand and reducing dependency on booking channels. He shares his best practices for identifying the ideal guest and employing effective communication strategies to foster guest loyalty and drive direct bookings. Join us for an enlightening conversation as Bart Sobies shares his expertise, recommendations, and visionary outlook on the vacation rental industry. Gain valuable insights that will empower you to navigate the evolving landscape and enhance your success as a hospitality owner or manager!

Highlights of the Episode:

02:21 - Guest Intro: Bart Sobies
03:46 – A little bit of history
06:10 – Highly encouraged direct booking strategies
09:12 – Focus on the audience you can speak to
10:42 – Direct bookings or homeowner marketing
14:19 – Getting into the vacation rental space
19:16 – Chat GPT and where it's taking the industry
23:52 – Will it replace original thought leadership?
28:36 – Best tips on learning ChatGPT
35:21 – How this applies to the future of SEO in the marketing world
38:00 – Working with people in vacation rentals
40:38 – Not depending on a channel and building a brand
49:25 – Tying it all in to the guest experience
53:15 – Closing

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech. 

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Bart:
Website | Linkedin | Facebook | Instagram | 5-Day AI Challenge

Connect with Alex and Annie:
Alex Husner | Annie Holcombe
AlexAndAnniePodcast.com

Send us a message!

Join us for an enlightening conversation with Jeff Iloulian, the CEO of HostGPO, a game-changing buying group for short-term rentals. Discover Jeff's remarkable journey from lawyer to successful vacation rental operator. He founded HostGPO to solve the challenge of sourcing high quality, affordable products for vacation rentals. By leveraging collective buying power, HostGPO transforms the industry, making it easier for operators to access top-notch products at discounted rates.

In this episode, discover how HostGPO helps vacation rental owners save money in the long run by sourcing durable, commercial-grade furniture. We explore the challenges of dealing with property managers and homeowners, along with the valuable consulting and design services offered by HostGPO. 

Dive into the delicate balance between standardization and uniqueness in unit aesthetics. We also discuss how the COVID-19 pandemic exposed vulnerabilities in the vacation rental industry and how GPOs, like HostGPO, help alleviate decision fatigue for owners. Furthermore, we delve into the advocacy work for industry safety in vacation rentals. Tune in for insightful discussions on these topics and more, providing valuable insights for vacation rental owners!

Highlights of the Episode:
02:22 - Guest Intro: Jeff Iloulian
02:49 – Jeff and the company
06:11 – Company size and its operators
07:04 – Working with hosts big and small
08:15 – The process
09:58 – Dealing with property managers and homeowners
14:20 – Consulting and design service
17:42 – Homeowners upgrading their units
21:51 – Balancing standardization of units and uniqueness
24:59 – Going to the all-white model
28:33 – Covid exposed vacation rentals’ weaknesses
30:23 – Conversation with parents about transitioning
from practicing law to short term rentals
37:41 – Solving the decision fatigue
40:57 – Advocacy work for industry
42:08 – People are sleeping on safety
49:44 – Closing

This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech.

Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.

Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.

Connect with Jeff:

Website | Linkedin

Connect with Alex and Annie:
Alex Husner | Annie Holcombe
AlexAndAnniePodcast.com

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