Alex and Annie: The Real Women of Vacation Rentals

In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie to talk about the realities of running a vacation rental business in the Outer Banks, one of the most established and distinctive markets in the industry. They get into what makes the market different, from its geography and seasonality to its mix of inventory and long-standing operating norms.

Tom also shares what it takes to keep a legacy operation strong as market conditions change. The conversation explores weather and erosion challenges, guest and owner communication, selective growth, direct bookings, linen and laundry logistics, dynamic pricing, onboarding complexity, and the reset in owner expectations after the COVID boom. 

If you work in vacation rentals, especially in a mature or highly seasonal market, this episode offers a practical look at what long-term success requires behind the scenes. 

Episode Chapters:

04:20 - Tom Stewart’s path into vacation rentals

08:18 - What makes the Outer Banks such a unique vacation rental market

11:37 - Weather, erosion, road access, and operating through disruption

20:56 - Why legacy markets function differently from newer STR markets

25:05 - Professionally managed inventory and Resort Realty’s direct booking mix

27:18 - Growth vs. scale and why selective inventory matters

30:41 - Laundry, linens, and simplifying operations at scale

36:13 - How Resort Realty approaches dynamic pricing

44:16 - Expanding into long-term rentals and building steadier cash flow

49:01 - Why onboarding large homes is more complex than it looks

54:15 - How owner expectations changed after the COVID boom

58:43 - Why pricing and demand look different now

1:00:38 - Tom’s advice for people getting into vacation rental operations

Connect with Tom:

LinkedIn: https://www.linkedin.com/in/tom-s-8b607938/ 

Website: https://www.resortrealty.com/ 

✨ Exclusive Offer to Alex & Annie Listeners:

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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 #outerbanks

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Human trafficking is a complex and often misunderstood issue, and one that exists across communities, including within hospitality.

In this episode, we’re joined by Betsy Steckler, Regional Director of Partner Services at Booking.com, and Jennifer Easterday, Head of Human Rights at Booking.com, to talk about how their teams are approaching human trafficking through awareness, education, and partner support.

From building training programs to equipping operators with practical tools, they share how Booking.com is working to help partners better understand the signs, respond appropriately, and create safer environments for both guests and communities.

We then continue the conversation with Philippa King, Deputy CEO of It’s A Penalty, a global non-profit organization focused on raising awareness and preventing human trafficking through large-scale campaigns tied to major events like the Super Bowl and the upcoming World Cup.

Philippa shares how these campaigns work, why major events create both risk and opportunity, and how collaboration between platforms, organizations, and local communities plays a critical role in prevention.

Across both conversations, a few themes stand out: the importance of awareness, the need for practical action, and the role that individuals, teams, and communities can play in recognizing and responding to potential risks.
While the issue is complex, the conversation highlights practical ways to better understand it and take action when something doesn’t feel right.

Episode Chapters:
03:00 – Booking.com partner services and human rights overview
05:30 – Human trafficking awareness in hospitality
08:30 – Understanding human trafficking in lodging and guest environments
10:30 – How operators and teams can stay informed
13:00 – Signs of human trafficking in guest stays
18:00 – Reporting suspicious activity and escalation process
22:30 – Training and resources for hospitality teams
30:36 – It’s A Penalty overview and mission
31:00 – How It’s A Penalty campaigns started
34:10 – Human trafficking risks during major events
36:20 – Types of human trafficking explained
40:30 – Real-world example of trafficking in a rental property
43:00 – Why human trafficking is often hidden in plain sight
45:30 – Practical steps for awareness and prevention
47:10 – World Cup preparation and risk awareness

Connect with Betsy:

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

Connect with Jennifer:

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

Connect with Philippa:

LinkedIn: https://www.linkedin.com/in/philippa-king-04307b4a/

Website: https://itsapenalty.org/

✨ 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 #humantrafficking

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In this episode, we’re joined by Leo Walton, Co-founder of Truvi, and Sarah Nan DuPre, Strategic Partnerships Director at AirDNA. Leo and Sarah are also the co-hosts of The Check-In Podcast, and they join us for a conversation about the upcoming Short Stay Summit in London and the industry conversations surrounding it.

Leo and Sarah will be serving as emcees for this year’s event, and they share why the Short Stay Summit has become such an important gathering for the industry, especially as regulation, technology, and market dynamics continue to evolve across different regions.

If you’re curious about the conversations shaping the industry today, this episode offers a preview of what to expect from one of the sector’s most talked-about gatherings.

Episode Chapters:

06:34 – What attendees can expect from this year’s Short Stay Summit in London

07:06 – What makes the Short Stay Summit different from other industry events

14:43 – Why bringing operators and policymakers together matters

14:56 – Key conversations happening across the short-term rental industry

25:13 – Differences between US and European operator mindsets

25:13 – How operators approach technology and tech stacks in different markets

30:35 – The growing role of AI in hospitality operations

Connect with Leo:

LinkedIn: https://www.linkedin.com/in/leo-walton-aa59bb25/
Website: https://truvi.com/ 

Connect with Sarah:

LinkedIn: https://www.linkedin.com/in/sarah-nan-dupre-86815828/ 

Explore Short Stay Summit:

Website: https://www.shortstaysummit.org/ 

✨ 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 #shortstaysummitlondon

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Distribution in the vacation rental industry has never been more complex. Property managers today are balancing major OTAs, niche platforms, emerging luxury channels, and an increasingly layered tech stack, all while trying to deliver exceptional guest experiences.

In this episode, Alex & Annie sit down with Blake Warner, CEO of BookingPal, to talk about how distribution is evolving and what it takes to build scalable infrastructure in a rapidly maturing industry.

Blake shares how BookingPal operates at the center of the ecosystem, connecting property managers, PMS platforms, and global channels, and offers his perspective on where the industry is heading. The conversation explores how distribution strategies are expanding beyond the traditional OTA landscape, the opportunities emerging in luxury and niche channels, and why technology innovation must balance efficiency with simplicity.

Drawing from his background in investment banking and capital markets, Blake also discusses the realities of scaling technology companies in the vacation rental space and why consolidation across the tech landscape may be inevitable.

Episode Chapters:
03:01 Introducing Blake Warner, CEO of BookingPal
03:44 Blake’s background in investment banking and capital markets
04:26 What BookingPal sees across distribution channels heading into 2026
06:07 The realities of running a channel management business
12:32 New BookingPal features and product developments for 2026
15:30 Is vacation rental tech getting better or more complex?
17:05 The explosion of software tools in the STR tech stack
20:03 How many channels the average property manager distributes to
21:21 Which distribution channels are gaining traction
22:53 Luxury platforms and the blurring lines in the ecosystem
24:41 Why helping managers focus on hospitality still matters most
28:13 Travel agents, discovery, and how distribution expands the market
30:05 Why it’s difficult for vacation rental companies to go public
35:44 How the industry has evolved since pre-COVID

Connect with Blake:
LinkedIn: https://www.linkedin.com/in/blakewarner/
Website: https://bookingpal.com/

✨ 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 #distribution

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Growth in short-term rentals often gets framed as a numbers game. More properties, more markets, more tech, and more scale.

But what if growth isn’t about doing more but choosing better?

In this 1st of the Month Bonus episode, Alex & Annie sit down with Carly Traub, Co-Founder and CEO of Lazy Sunday Rentals, to talk about what it really looks like to build a business intentionally in a fast-moving, information-heavy industry.

Carly launched her company in 2022 alongside her husband, starting with a single property and quickly scaling to a growing portfolio. Like many operators, she said yes to everything early on. Over time, she realized that not all growth is aligned growth.

This conversation explores the shift from reactive expansion to thoughtful refinement.

Episode Chapters:
04:53 Moving from channel-dependent to brand-driven
06:15 Why saying “yes” to everything works at first and why it eventually doesn’t
07:15 Maximizing your existing tech stack before adding more tools
6:26 Evaluating return on time, not just return on money
18:23 Building a direct booking strategy that reflects your identity
27:58 How to define the kind of guest experience you actually want to deliver
31:59 Why smaller operators need a seat at the DMO table
41:26 The realities of operating in a “hot” investment market
45:29 Unrealistic investor expectations and the myth of easy remote hosting

If you’re building in a crowded market and want growth that fits your vision, this episode will help you pause, refocus, and move forward with intention.

Connect with Carly:

LinkedIn: https://www.linkedin.com/in/carly-traub-6a402325/ 

Website: https://lazysundayrentals.com/ 

✨ 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/

#vacationrentals #shorttermrentals #intentionalgrowth

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In this episode, Alex & Annie sit down with Tim Hubbard, CEO of Corzly, to break down how a virtual property management model actually works and what it takes to make it successful.

Tim started in long-term rental investing before shifting into short-term rentals more than a decade ago. As his portfolio grew across multiple states, and eventually internationally, he built the systems needed to manage properties remotely. That operational backbone became Corzly, a virtual management partner now supporting property managers in more than 40 cities.

Tim shares how their white-label backend model works, how they collaborate with on-the-ground teams, and where AI fits into real workflows. Not just automated check-in messages, but layered operational processes that involve owners, cleaners, early check-in requests, and revenue decisions.

Episode Chapters:
1:04 – From Long-Term Rentals to a 40-City Virtual Operation
4:02 – The Idea Behind “Core Operations”
5:28 – What Virtual Property Management Actually Means
6:08 – Why 10–60 Unit Managers Are Their Sweet Spot
7:22 – Running the Backend Without Owning the Listings
11:17 – How Much Can You Really Automate With AI?
11:58 – The Early Check-In Example That Shows How Complex Workflows Get
15:55 – 225 Units Today… 10X Growth This Year?
19:58 – The Hardest Part of Scaling Across Markets
22:21 – Building Culture With a Fully Global Team
27:44 – Developing a 20-Unit Resort in Medellín
29:08 – Two Years of Permitting and What It Took to Launch

If you are exploring growth, efficiency, or a different structure for your management business, this episode offers a clear look at another way to build.

Connect with Tim:
LinkedIn: https://www.linkedin.com/in/tim-hubbard-str/
Website: https://corzly.com/ 

✨ 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/

#vacationrentals #shorttermrentals #propertymanagement

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In this episode, Alex & Annie sit down with Krista Goodrich and Kymberlee Nguyen, the duo behind Salty Dog Vacations, to talk about what it really takes to build a vacation rental company that guests remember and a team that is proud to be part of it.

They share how Salty Dog grew from early investing decisions in Daytona Beach into a full-scale operation, and how their approach to branding goes beyond design choices. It shows up in the details, the guest experience, and the way they protect their people.

The conversation also expands into Krista’s work in local advocacy and zoning, their broader mission to help more women build wealth through real estate, and how their community has grown through retreats and education.

Episode Chapters:
08:20 – How local rules, zoning, and community involvement shape what it takes to operate responsibly
15:07 – Building a brand guests remember: personality, pet-friendly touches, and guest joy
19:37 – Krista’s “Boss Lady Investor” work, and why real estate education needs to feel accessible
25:00 – How retreats and community experiences can become part of a bigger platform, not just a side project
33:32 – What it looks like to build a company culture where your team feels protected and respected
35:44 – The moment they fired an owner, and why that decision mattered for the business long term
40:25 – Why consistency matters more than “cute ideas,” especially once you are scaling

If you’re trying to build a stronger guest experience and a business that holds up as you grow, this one’s worth a listen.

Connect with Kym & Krista:
LinkedIn: https://www.linkedin.com/in/krista-goodrich-2823198/
Podcast: https://www.thebossladyinvestor.com/
Website: https://mysaltydogvacation.com/

✨ 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/

#vacationrentals #shorttermrentals #bossladyenergy

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Midterm rentals are moving from a side option to a real strategy. In this episode, Alex & Annie sit down with Jeff Hurst, CEO of Furnished Finder and former HomeAway and Expedia Group leader, to explain why 30+ day stays are gaining traction as many STR markets move into a more mature phase.

Jeff breaks down what makes midterm rentals different from short-term rentals, what demand is actually driven by, and why midterm can be a strong fit for operators looking for stability, fewer turnovers, and a guest profile rooted in real-life transitions.

Episode Chapters:
01:04 – Jeff’s background and how he views category shifts in rentals
06:16 – What Furnished Finder is, and what “midterm” means in practice
07:24 – Why the category is still early, and what professionalization looks like
08:35 – Who midterm guests are and what they need from a stay
12:01 – How midterm works operationally: screening, leases, deposits, and payments
22:48 – “Return on furniture” and the investment logic behind midterm
26:58 – Regulation, market maturity, and why more operators are taking midterm seriously
32:15 – Why midterm is gaining ground in saturated (mature) STR markets
33:21 – What types of properties fit midterm demand, and what does not

Connect with Jeff:
LinkedIn: https://www.linkedin.com/in/jeff-hurst-atx/
Website: https://www.furnishedfinder.com/

✨ 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/

#vacationrentals #shorttermrentals #MTR

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Destination marketing is in a pressure test.

Short-term rentals have become a major part of how people travel, yet many DMOs still struggle with how (or whether) to include them. At the same time, AI is speeding up the research-to-booking journey and forcing destinations to rethink what “relevance” even means.

In this episode, Alex and Annie sit down with Stuart Butler (President of Visit Myrtle Beach) and Adam Stoker (President of Brand Revolt) to unpack what’s getting in the way, what alignment can look like, and why the next version of destination marketing is going to require better coordination across the whole destination economy.

You’ll hear practical takes on funding dynamics, stakeholder value, the “illusion of relevance” in reporting, and why the future may turn DMO websites into something closer to infrastructure than a traditional marketing channel.

Episode Chapters:
00:54 – Stuart’s background and how he landed in destination work
02:27 – Adam’s background and how he sees the DMO landscape
05:37 – The “illusion of relevance,” metrics, and why DMOs feel behind
07:44 – The Indianapolis example, why some DMOs leave STRs out
09:28 – Can DMOs stay relevant without vacation rentals
11:53 – Why STRs need a seat at the table and what it takes to get one
14:34 – What STR operators can do in markets without big PM groups
19:16 – Funding reality, stakeholder influence, and how STRs earn attention
22:27 – Why getting involved with a DMO teaches you more than you expect
23:51 – The bigger DMO question, purpose, scope, and identity
30:31 – How performance reporting shaped destination websites
30:54 – Why the booking engine path can be a strategic dead end
36:49 – Stewardship, community trust, and what destinations are accountable for
50:06 – AI as a watershed moment for travel discovery and decision-making
57:59 – What destination content needs to look like in an AI-first world
1:02:21 – Closing thoughts on websites, infrastructure, and the road ahead

Connect with Stuart:
LinkedIn: https://www.linkedin.com/in/stuart-butler-50aaa45/
Website: http://www.visitmyrtlebeach.com/

Connect with Adam:
LinkedIn: https://www.linkedin.com/in/adamstoker/
Website: https://thebrandrevolt.com/

✨ 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/ 

#vacationrentals #shorttermrentals #DMO

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Condo-hotels and resort-style properties sit in a tricky middle ground. They are not traditional hotels, but they are not quite vacation rentals either. Many still run on hotel tech stacks, charge hotel-style commissions, and operate with hotel mindsets.

Meanwhile, guests are increasingly searching on vacation rental channels, homeowners are asking why they cannot find their units online, and off-site managers charging half the commission are pulling inventory away.

In our February First-of-the-Month bonus episode, we sit down with Emmanuel Lavoie, CEO of Jetstream, to unpack why so many condo-hotels and resort operators still resist distribution on channels like Airbnb and Vrbo, what it really takes to service this category well, and how AI is starting to reshape channel management.

Episode Chapters:
01:17 - Leaving a 10-year engineering career for travel tech
03:33 - How a Canadian OTA accidentally became a channel manager
9:43 - Why resorts still hesitate to embrace Airbnb and Vrbo
12:00 - What full-service channel management actually includes
13:42 - Why a $10 billion company chose service over cheaper tech
15:18 - Off-site managers are winning the homeowner battle
16:56 - The challenge of selling non-unique inventory on Airbnb
24:12 - Why one listing with 300 reviews beats 50 identical listings
30:42 - Building an AI-powered guest communication system
35:27 - Using AI for listing content creation at scale
38:21 - Empowering frontline teams as AI champions
42:09 - The human side of AI disruption
44:02 - Where Jetstream is heading next

Connect with Emmanuel:
LinkedIn: https://www.linkedin.com/in/emmanuel-lavoie-5b89b924/
Website: https://jetstreamtech.io/

✨ 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/

#vacationrentals #shorttermrentals #distribution

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