Alex and Annie: The Real Women of Vacation Rentals

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

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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