Alex and Annie: The Real Women of Vacation Rentals

When Airbnb changes its policies, the ripple effect can shake operators everywhere. For many, the problem is deeper than one policy update. Relying too heavily on a single platform leaves businesses vulnerable, and the cracks are starting to show.

In this episode, Mark Simpson, CEO and founder of Boostly, shares why now is the time for vacation rental operators to double down on direct bookings. Drawing from more than a decade of helping hosts grow beyond OTAs, Mark brings practical steps that any operator can put into action.

We cover:
1️⃣ Why overreliance on OTAs creates long-term risk for property managers
2️⃣ How to turn guest data into a foundation for repeat bookings
3️⃣ Simple strategies that work even without a large marketing budget
4️⃣ Ways to use referrals, user-generated content, and email campaigns to build stronger relationships with guests
5️⃣ What Boostly is creating to make direct bookings more accessible and effective

Mark also opens up about the importance of creativity in marketing, sharing real stories of campaigns that cut through the noise at conferences and online. His approach proves that building direct channels is not only possible but powerful.

Connect with Mark:
LinkedIn: https://www.linkedin.com/in/mrmarksimpson/
Website: https://boostly.co.uk/

✨ Exclusive Offer to Alex & Annie Listeners:

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0  

Free Market Assessment from Track (valued at $400)

Get 3–5 actionable insights tailored to your business. Meet one-on-one with an expert to evaluate your market, identify opportunities, and build a winning strategy.

👉 https://calendly.com/dstephens-tnsinc 

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #directbookings

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What does it take to scale luxury vacation rentals while protecting the legacy of the brands that built them?

In this episode, Alex & Annie welcome back Scott Wiseman, CEO of Nocturne Luxury Villas, for an inside look at how Nocturne approaches acquisitions in the luxury vacation rental space. 

Instead of treating acquisitions as one-size-fits-all deals, Scott explains how his team works with founders to create personalized exit plans that honor their legacy, protect employees, and keep guests at the heart of the business.

We discuss:
1️⃣ How Nocturne has grown to nearly 1,200 homes across six markets
2️⃣ Why culture and relationships are as important as financial outcomes
3️⃣ How Nocturne’s concierge services give vacation rentals an edge over resorts
4️⃣ What he sees ahead for the luxury travel sector
5️⃣ Honest advice for owners considering selling their business

Scott brings a grounded, people-first perspective to what’s often seen as a purely financial process. His approach reminds us that growth can happen without losing the heart of a company — its people, its culture, and the relationships that built it.

Connect with Scott Wiseman:
LinkedIn: https://www.linkedin.com/in/scottfwiseman/ 

Connect with Nocturne:
Website: https://www.nocturneluxuryvillas.com/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0  

Free Market Assessment from Track (valued at $400)

Get 3–5 actionable insights tailored to your business. Meet one-on-one with an expert to evaluate your market, identify opportunities, and build a winning strategy.

👉 https://calendly.com/dstephens-tnsinc 

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #acquisitions

Send us a message!

Flexible cancellation policies are no longer optional in today’s vacation rental market. Guests expect them, OTAs prioritize them, and competitors are already adapting. But for property managers, relaxed policies often feel like a direct threat to revenue and owner trust.

In this episode, we talk with Sasha Lawler, CEO and Founder of Roam, about how her company is eliminating that trade-off. Roam’s embedded insurance model allows managers to offer flexible bookings that attract more guests while ensuring income is protected even if cancellations occur.

Sasha shares her 15+ year journey in hospitality and vacation rental tech, the conversations with property managers that inspired Roam, and why now is the moment for the industry to catch up with hotels and airlines in offering flexibility.

We discuss:

1️⃣ Why strict cancellation policies create tension between managers, owners, and guests

2️⃣ How Roam’s model differs from traditional travel insurance

3️⃣ The tech behind embedding refundable and non-refundable rate options into booking sites

4️⃣ Why smaller operators are leveraging Roam to stabilize revenue and win new owners

5️⃣ How turning cancellations into a strength can improve guest trust and long-term brand growth

If cancellations have ever kept you up at night, this episode will show you how flexibility can protect (not jeopardize) your revenue.

Connect with Sasha:
LinkedIn: https://www.linkedin.com/in/sasha-lawler-a4b33677/
Website: https://goroam.io/

✨ Exclusive Offer to Alex & Annie Listeners:

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0 

Free Market Assessment from Track (valued at $400)

Get 3–5 actionable insights tailored to your business. Meet one-on-one with an expert to evaluate your market, identify opportunities, and build a winning strategy.

👉 https://calendly.com/dstephens-tnsinc

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected]

#vacationrentals #shorttermrentals #cancellationpolicy

Send us a message!

In this week’s episode, we’re joined by Adrienne Clark (President & COO) and Caleb Yaryan (Chief Product Officer) of Xplorie, a trusted partner for vacation rental operators looking to enhance guest satisfaction while gaining a competitive edge.

For nearly 30 years, Xplorie has been connecting lodging providers with local attractions in more than 70 destinations across the U.S., creating seamless, curated activity experiences that guests actually value. But more than just a perks program, Xplorie is a strategic tool that helps property managers attract bookings, improve guest loyalty, and offer real hospitality that extends beyond the front door.

Adrienne and Caleb share their personal paths into the industry, the philosophy behind Xplorie’s business model, and the behind-the-scenes work that goes into ensuring every activity meets their high standards of quality and service.

We discuss:
1️⃣ How Xplorie supports PMs in creating meaningful guest experiences
2️⃣ Why activities are a powerful differentiator in a crowded market
3️⃣ Trends in traveler behavior post-COVID, from outdoor demand to last-minute bookings
4️⃣ How Xplorie helps guests and operators when things don’t go as planned
5️⃣ The importance of local partnerships and activity curation
6️⃣ Real-time integrations, guest support, and why call centers still matter
7️⃣ Why Xplorie limits the number of partners per market
8️⃣ What’s ahead for Xplorie as they approach their 30th anniversary

Whether you're looking to stand out without lowering rates, boost shoulder season bookings, or create memories guests will talk about long after check-out, this conversation is packed with actionable insights you won’t want to miss.

Connect with Adrienne:
LinkedIn: https://www.linkedin.com/in/adrienneclark1322/

Connect with Caleb:
LinkedIn: https://www.linkedin.com/in/caleb-yaryan-15447219/

Connect with Xplorie:
Website: https://xplorie.com/
LinkedIn: https://www.linkedin.com/company/xplorie/

✨ Exclusive Offer to Alex & Annie Listeners:

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Free Market Assessment from Track (valued at $400)
Get 3–5 actionable insights tailored to your business. Meet one-on-one with an expert to evaluate your market, identify opportunities, and build a winning strategy.

👉 https://calendly.com/dstephens-tnsinc

Considering an exit strategy?
Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected]

#vacationrentals #shorttermrentals #guestexperience

Send us a message!

In this special first-of-the-month bonus episode, Alex & Annie sit down with a longtime friend and industry leader Tyann Marcink Hammond to talk about a timely and much-needed initiative to support host education. 

Tyann shares how she’s leading an effort to prepare short-term rental operators ahead of the 2026 FIFA World Cup, starting in Kansas City and expanding to other host cities across North America.

Annie also shares a major personal announcement. After a successful career working with some of the biggest brands in vacation rentals, Annie is officially stepping into entrepreneurship with the launch of Annie & Co. Solutions.

Key topics discussed:
1️⃣ Annie’s big news: launching Annie & Co. Solutions
2️⃣ How Annie made the decision to go independent
3️⃣ Tyann shares her “word of the year” and what it led to
4️⃣ How the World Cup Hosting Crash Course began
5️⃣ Preparing hosts to be good neighbors during major events
6️⃣ Why advocacy and education go hand in hand
7️⃣ Potential impact on local regulations and STR reputation
8️⃣ The vision for a more organized and professional STR industry

From new ventures to community advocacy, this episode offers a thoughtful look at the opportunities and responsibilities that come with growing in the vacation rental industry.

Connect with Annie & Co. Solutions:
Website: https://anniecosolutions.com/
LinkedIn: https://www.linkedin.com/in/annie-holcombe-vrgal/

Connect with Tyann:
LinkedIn: https://www.linkedin.com/in/tyannmarcink/

✨ Exclusive Offer to Alex & Annie Listeners:

Get a free market assessment from Track with 3 to 5 actionable insights tailored to your business. (valued at $400)

You will meet one-on-one with an expert to help evaluate your market, identify opportunities, and build a strategy to help you stand out.

👉 https://calendly.com/dstephens-tnsinc

#vacationrentals #shorttermrentals #worldcup

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Airbnb’s evolving policies have become one of the most pressing conversations in vacation rentals today - sparking questions, frustrations, and new realities for property managers across the industry.

In this episode, Alex & Annie welcome Dennis Schaal, Founding Editor at Skift, to discuss what these changes mean for property managers and the broader short-term rental ecosystem. With more than 25 years of experience covering online travel, Dennis brings a sharp journalistic lens to the strategies shaping hospitality and why Airbnb’s moves demand close attention.

Together with Alex & Annie, the conversation explores:
✅ What are the changes in Airbnb’s terms and conditions
✅ Why Airbnb made this move now
✅ How property managers could be affected
✅ What it signals about Airbnb’s relationship with hosts and guests
✅ Broader implications for OTAs, regulation, and tech trends in the STR space

This is a must-listen for property managers looking to stay ahead of the curve and understand how policy shifts at the top can reshape daily operations on the ground.

Connect with Dennis:
LinkedIn: https://www.linkedin.com/in/dschaal/

✨ Exclusive Offer to Alex & Annie Listeners:

Get a free market assessment from Track with 3 to 5 actionable insights tailored to your business. (valued at $400)

You will meet one-on-one with an expert to help evaluate your market, identify opportunities, and build a strategy to help you stand out.

👉 https://calendly.com/dstephens-tnsinc

Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team:

👉 https://calendly.com/michelle-marquis-grandwelcome/30min

#vacationrentals #shorttermrentals #airbnb

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What if imposter syndrome wasn’t a weakness, but a sign you’re growing?

In this episode, Alex and Annie are joined by Michelle Marquis, founder of The Marquis Effect and now author of The Bossy Girl’s Guide to Leadership, which has just been released. Written for women navigating leadership and self-doubt, the book is part memoir, part guidebook, and 100% Michelle’s authentic voice.

Michelle reveals the mindset shifts that shaped her journey, including:

• Earn It While You Learn It – why progress comes from figuring it out as you go.
• The Support Squad Effect – how to build your personal “board of directors.”
• Blended Life vs. Balanced Life – a more realistic approach to work and family.
• Agile Leadership – evolving your leadership style through constant learning.

She also opens up about moments of rejection, how she reframed imposter syndrome into fuel, and why thriving as a leader often means being willing to feel uncomfortable.

If you’ve ever struggled with self-doubt or questioned whether you’re “enough,” Michelle’s story will encourage you to see those feelings as proof that you’re moving in the right direction.

Connect with Michelle:

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

The Bossy Girl’s Guide to Leadership: https://www.amazon.com/dp/1968250506 

✨ Exclusive Offer to Alex & Annie Listeners:

Get a free market assessment from Track with 3 to 5 actionable insights tailored to your business. (valued at $400)

You will meet one-on-one with an expert to help evaluate your market, identify opportunities, and build a strategy to help you stand out.

👉 https://calendly.com/dstephens-tnsinc

Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team:

👉 https://calendly.com/michelle-marquis-grandwelcome/30min

#vacationrentals #shorttermrentals #impostersyndrome

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This week, Alex & Annie sit down with Valerie Gangas, Founder & CEO of Juniper Holiday + Homes, for a conversation that blends business, design, and deep personal transformation.

Valerie shares how Juniper began with a personal real estate portfolio and evolved into a thriving multi-market vacation rental management company operating in Michigan, Wisconsin, Florida, and Utah. From navigating the early days of property management without industry experience to creating beautifully designed homes that guests love, she reflects on the mindset and adaptability that fueled her growth.

But Valerie’s story goes beyond entrepreneurship. Drawing from her background in hospitality, real estate development, and her work with the David Lynch Foundation and Oprah Winfrey Studios, she opens up about her journey through profound personal loss  and how it inspired her two books, Enlightenment Is Sexy and In Deep Shift.

In this episode, you’ll hear:

• How a pandemic pivot sparked the birth of Juniper Holiday + Homes
• Why design and hospitality go hand in hand in creating guest loyalty
• The life lessons behind Valerie’s books, and the courage to live with vulnerability
• How to notice and trust the “signs” that guide you toward the right opportunities
• Why detachment from outcomes can lead to more meaningful success

Whether you’re an entrepreneur, a creative, or someone navigating your own turning point, Valerie’s story is a reminder that the paths we never planned often lead us to our most fulfilling chapters.

Connect with Valerie:

LinkedIn: https://www.linkedin.com/in/valerie-gangas/ 

Website: https://www.juniperholidayandhome.com/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Get a free market assessment from Track with 3 to 5 actionable insights tailored to your business. (valued at $400)

You will meet one-on-one with an expert to help evaluate your market, identify opportunities, and build a strategy to help you stand out.

👉 https://calendly.com/dstephens-tnsinc

Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team:

👉 https://calendly.com/michelle-marquis-grandwelcome/30min

#vacationrentals #shorttermrentals #strinnovation

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What did it take to bring vacation rentals into the mainstream and what did we lose along the way?

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we’re joined by industry veteran and Finding Better podcast host John Suzuki, who reflects on the emotional and operational toll of the tech transformation that reshaped short-term rentals over the last two decades.

From the early days of fax machines and yellow page listings to the rise of e-commerce and AI, John helped lead the charge at Expedia Group during one of the most turbulent and defining chapters of the industry. But behind the progress came growing pains, confusion, fear, and a communication breakdown that left many property managers feeling left behind.

We dive into:
1️⃣ The emotional toll of industry-wide disruption
2️⃣ Why innovation without empathy nearly broke trust
3️⃣ The importance of clear communication during periods of change
4️⃣ How AI could finally simplify operations (if we let it)
5️⃣ Why “scrappiness” is the most important skill to build now
6️⃣ The rise of Finding Better and John’s mission to bring heart back to business

If you’ve ever felt overwhelmed by how fast things are moving or nostalgic for the days when hospitality was more human, this episode is for you.

✨ Exclusive Offer to Alex & Annie Listeners:

Get a free market assessment from Track with 3 to 5 actionable insights tailored to your business. (valued at $400)

You will meet one-on-one with an expert to help evaluate your market, identify opportunities, and build a strategy to help you stand out.

👉 https://calendly.com/dstephens-tnsinc

Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team:

👉 https://calendly.com/michelle-marquis-grandwelcome/30min

#vacationrentals #shorttermrentals #strinnovation

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In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Paul Kromidas, Founder & CEO of Summer, to talk about the growing need for asset intelligence in short-term rental investing, and why gut feel is no longer enough when deciding which properties to buy.

Paul shares his journey from building products at Airbnb to launching Summer, a powerful underwriting and asset management platform designed specifically for STR operators. Originally built as an internal tool while running his own rental portfolio, Summer is now helping operators and investors across the U.S. evaluate, acquire, and manage properties with more confidence and accuracy.

Key Topics Discussed:
1️⃣ Why post-COVID performance data is misleading and how to normalize it
2️⃣ The difference between pricing tools and true asset intelligence
3️⃣ How Summer helps operators know if a property will perform before they buy it
4️⃣ What investors, lenders, and operators are really looking for in STR data
5️⃣ Lessons from Paul’s time at Airbnb, including what makes a brand resilient

If you’re buying or managing STR properties without a reliable way to underwrite or track performance, this episode is a must-listen.

Connect with Paul:
LinkedIn: https://www.linkedin.com/in/paul-kromidas-a8343519/
Website: https://summeros.com/

✨ Exclusive Offer to Alex & Annie Listeners:

Get a free market assessment from Track with 3 to 5 actionable insights tailored to your business. (valued at $400)

You will meet one-on-one with an expert to help evaluate your market, identify opportunities, and build a strategy to help you stand out.

👉 https://calendly.com/dstephens-tnsinc

Go live with Homes & Villas by Marriott Bonvoy by August 4, 2025, and receive Marriott Bonvoy Platinum Status for one year, 36000 bonus points, and a marketing feature on a Homes & Villas marketing channel after you launch:

👉 https://partners.homes-and-villas.marriott.com/s/event-property-managers-contact-us?ev=AApod25

Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team:

👉 https://calendly.com/michelle-marquis-grandwelcome/30min

#vacationrentals #shorttermrentals #assetintelligence

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