Alex and Annie: The Real Women of Vacation Rentals

In this week’s episode, we're joined by Matt Gurley, Director of Sales and Partner Integrations at the Lynnbrook Group, for a deep dive into the payment side of vacation rentals that most property managers overlook until it’s too late.

From fraud prevention to faster checkouts to smarter cash flow tools, Matt breaks down how Lynnbrook is simplifying payment processing and helping operators keep more of what they earn. With a career that started in the OTA integration trenches and evolved into leading-edge fintech, Matt brings a unique perspective on why vacation rental companies need more than just a generic payment provider.

If you've ever dealt with chargebacks, payout delays, or struggled with reconciling your books, this one’s for you.

Key Topics Discussed:

1️⃣ Why payment processing is more than just a backend task in vacation rentals

2️⃣ Common blind spots property managers face when it comes to fraud and chargebacks

3️⃣ How modern checkout options like Apple Pay, Pay Later, and Venmo are shaping guest expectations

4️⃣ What property managers can do to protect profits and streamline payouts

5️⃣ The importance of industry-specific tools for high-risk booking scenarios

6️⃣ Lessons learned from OTAs, hurricanes, and helping PMs stay financially stable

7️⃣ What operators should ask when choosing a payment partner

8️⃣ The real cost of ignoring risk and compliance

Connect with Matt:
LinkedIn: https://www.linkedin.com/in/matthew-gurley-74688592/
Website: https://www.lynnbrookgroup.com/ 

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠

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/jessica-singer-grandwelcome/intro

#vacationrentals #shorttermrentals #paymentprocessing

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In this episode, we sit down with two industry powerhouses: Dennis Goedheid, CEO of Casiola, and Shahar Goldboim, CEO of Boom and founder of DesignedVR, to unpack the story behind their groundbreaking new partnership.

As the vacation rental industry continues to mature, operators are finding new ways to grow that prioritize sustainability, clarity, and control. This conversation explores the revenue-sharing agreement between DesignedVR and Casiola, a creative alternative to the traditional franchise or acquisition model.

Shahar shares his decision to step away from the day-to-day operations of DesignedVR to fully focus on growing Boom, the AI-powered property management system he built with his two brothers. Dennis explains how Casiola's clear focus on hospitality and operations made them the right partner to take over and grow the DesignedVR portfolio.

Key Topics Discussed:
1️⃣ Why Shahar chose to partner rather than sell or franchise
2️⃣ How Dennis and Shahar aligned on values, leadership, and long-term vision
3️⃣ What property managers can learn about letting go to grow
4️⃣ The operational and cultural challenges of integrating a new team and brand
5️⃣ How Casiola approaches expansion without sacrificing focus
6️⃣ Why the traditional "do it all" mindset often leads to burnout in STR
7️⃣ How Dennis views focus as a competitive advantage
8️⃣ Why Shahar sees clarity as a form of leadership
9️⃣ What role AI and automation will play as Boom continues to scale

You'll also hear how Casiola is managing the integration of DesignedVR's team, technology, and properties, and why this move is about more than just operations. At its core, it's a partnership built on aligned values and a shared vision for what vacation rental businesses can become.

Connect with Shahar:
LinkedIn: https://www.linkedin.com/in/shahar-goldboim-80820b95/
Boom: https://www.boomnow.com/

Connect with Dennis:
LinkedIn: https://www.linkedin.com/in/dennisgoedheid/
Casiola: https://www.casiola.com/

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠

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/jessica-singer-grandwelcome/intro 

#vacationrentals #vacationrentalfranchising #STR

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Is the short-term rental industry on the edge of a travel recession, or just entering a new phase of normalization?

In this episode of Alex & Annie: The Real Women of Vacation Rentals, AirDNA’s Chief Economist Jamie Lane joins us to explain what the data is revealing about the 2025 market. With demand softening among budget travelers, international bookings pulling back, and economic uncertainty on the rise, Jamie helps make sense of the mixed signals facing STR professionals today.

Jamie also shares how AirDNA is evolving to better support property managers in this climate, with new tools, smarter comps, and deeper forecasting capabilities. Whether you're adjusting pricing strategies, watching booking windows shrink, or wondering what’s next for growth, this conversation provides the clarity and context you need.

Key Topics Discussed:
1️⃣ Are we in a travel recession? Early signals from airline and STR data
2️⃣ Why summer 2025 bookings are slower, especially in budget and urban segments
3️⃣ Hotels gaining share in cities as STR growth is restricted by regulation
4️⃣ Supply growth slows across most markets and what that means for operators
5️⃣ Signs of guests trading down, shortening trips, and delaying decisions
6️⃣ The impact of fewer Canadian and European travelers this year
7️⃣ Airbnb’s urban inventory problem and the increasing presence of hotels on OTAs

Jamie also shares his outlook for the rest of 2025 and why, despite current challenges, the long-term growth of short-term rentals remains strong.

Connect with Jamie:
LinkedIn: https://www.linkedin.com/in/jamiehlane/

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠

#vacationrentals #travelrecession #shorttermrentals

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In this empowering episode of Alex & Annie: The Real Women of Vacation Rentals, Shelley Brown joins us to talk about how breaking outdated expectations and embracing your weird can lead to more authentic leadership and a deeper sense of belonging.

As the original "Rebel in a Gown," Shelley brings her signature blend of authenticity, artistry, and humor to a conversation that challenges the status quo on leadership, burnout, and belonging.

Shelley shares how an unexpected career detour and a serious spinal injury pushed her to redefine success. Not by how hard she could hustle, but by how deeply she could connect. 

That shift led her from hotel lobbies and sales calls to keynote stages, where she now helps teams rediscover purpose, vulnerability, and human connection.

Key topics discussed:

1️⃣ How Shelley’s WEIRD framework invites more inclusive and connected leadership

2️⃣ Why outdated ideas of success often lead to burnout and disconnection

3️⃣ What it means to “rebel” against norms without being loud about it

4️⃣ The power of journaling, mindfulness, and small daily choices

5️⃣ How to lead with legacy in mind and why it starts with you

This episode is an invitation for you to reconnect with the version of yourself that existed before the world told you who to be. And yes, we all wore gowns for it.

Connect with Shelley:
LinkedIn: https://www.linkedin.com/in/shelleybbrown/
Website: https://shelleybrownofficial.com/ 

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠

#vacationrentals #leadership #burnout

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Alex & Annie bring you behind the scenes at VRNation 2025 to explore direct booking strategies, industry growth, tech innovation, and the evolving role of associations in vacation rentals.

Recorded live in Austin, Texas, this special bonus episode captures real-time insights from the conference floor. Alex & Annie had on-the-spot conversations with some of the industry’s most influential voices and rising innovators to unpack the real story behind what’s shaping the vacation rental space today.

In true Alex & Annie fashion, they also asked some of the conference participants one powerful question: “In one word, what’s the biggest problem in vacation rentals?” The answers reveal a lot about where the industry stands and where it's headed.

Featuring interviews with:

• Heidie Henriksen – Executive Director of VRNation
• Orlie Benjamin – Founder of Lasoh
• Dylan Bozarth – General Manager of 30A Escapes
• Tera Lorimer – Founder of Luxury Getaways and VRNation Board Member
• Heather Van Wie – Founder of Cottages on the Key and VRNation Board Member
• Nicholas Wegener & Roy Collins – Founders of SendSquared
• Anne Gardner – Executive Director at VRMA

Whether you were at VRNation or following the buzz afterward, this episode captures the energy and insight straight from Austin.

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie 

#vacationrentals #Shorttermrentals #VRNation2025

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In this episode of Alex & Annie: The Real Women of Vacation Rentals, we’re joined by Ian Ackland, Managing Director of the Americas at Booking.com, for a candid look at how one of the world's largest travel platforms is evolving its approach to better serve property managers.

With more than 30 years in the travel industry and over a decade at Booking.com, Ian shares how the company is shifting from being just a distribution channel to becoming a true partner for vacation rental professionals. From reimagining payment systems and investing in connectivity, to expanding their U.S. market presence and leveraging AI, Ian walks us through the strategy behind Booking.com's efforts to reduce friction and drive more value for hosts at every stage of growth.

Whether you’re a large enterprise or just getting started, this episode is packed with practical insights on how to work smarter, tap into new guest demand, and build a more effective tech stack through stronger partnerships.

Key Topics Discussed:

1️⃣ Ian’s background in hospitality and why hosting is personal to him
2️⃣ The evolution of Booking.com's vacation rental strategy
3️⃣ Why connectivity partners like NextPax play a key role in host success
4️⃣ How Booking.com is supporting both enterprise and mid-sized property managers
5️⃣ What makes listings convert: content, rate plans, and smart distribution
6️⃣ The redesign of their payment system to solve real host pain points
7️⃣ How generative AI is helping streamline guest communication
8️⃣ Loyalty, trust, and the value of high-frequency guests
9️⃣ The tools and resources Booking.com offers to support property managers at scale

Connect with Ian:
LinkedIn: https://www.linkedin.com/in/ian-ackland-1b3b444/

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠ 

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie 

#VacationRentals #ShortTermRentals #OTA

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In this week’s episode, Matt Landau returns to the show to share one of the most personal and transformational shifts of his career — a journey from building systems and scaling success to rediscovering the power of human connection.

Long known as a community builder and founder of VRMB, Matt opens up about the moment everything changed. After years of being surrounded by the same ideas and doing the same routines, he stepped outside the norm and into a retreat that would forever alter his perspective on leadership, creativity, and authenticity.

Now leading his own immersive experiences through Here Goes Nothin’, Matt is helping business leaders from all industries explore their own breakthrough moments by leaning into discomfort, curiosity, and connection.

Key Topics Discussed:
1️⃣ The “aha” moment that shifted Matt’s trajectory
2️⃣ Why scaling isn't always the answer—and what comes next
3️⃣ The creative power of letting go of control
4️⃣ What it really means to lead with authenticity
5️⃣ How retreats are reshaping the future of leadership and hospitality
6️⃣ Why personal breakthroughs often unlock professional success

If you’ve ever felt stuck, uninspired, or simply curious about what else might be possible, this episode is your invitation to take the leap.

Connect with Matt:
LinkedIn: https://www.linkedin.com/in/landaumatt/
Website: https://heregoesnothin.com/ 

Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠ 

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie 

#vacationrentals #connection #heregoesnothin

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In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Boogie Wittenburg, the new CEO of TravelNet Solutions, makers of Track PMS. With a background in mission-critical technology powering global brands, Boogie brings a fresh, people-first perspective to the vacation rental tech space.

Building on the strong foundation laid by the company’s founders, Boogie shares how he’s guiding TravelNet Solutions into its next chapter — one that balances continuity with innovation. With a renewed focus on culture, customer experience, and thoughtful technology, Boogie brings a clear vision for scaling both the platform and the people behind it.

Key Topics Discussed:
1️⃣Boogie’s journey from global tech to short-term rentals
2️⃣Why servant leadership is at the core of his management style
3️⃣How TravelNet Solutions is improving customer support and answering the phone again (yes, really!)
4️⃣The rollout of the new Owner Mobile App and its impact on retention
5️⃣Track’s approach to product development: build, buy, or partner
6️⃣The role of AI in scaling support and internal operations
7️⃣What true team engagement looks like—and why it matters

Boogie also shares a powerful reflection on legacy, leadership, and building a company where employees, customers, and innovation thrive together.

Whether you’re a property manager, tech vendor, or industry leader, this episode offers valuable insight into what it takes to scale a software company without losing sight of people.

Connect with Boogie:
LinkedIn: https://www.linkedin.com/in/oduswittenburg/
Website: https://tnsinc.com/

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie

Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.

#VacationRentals  #TrackPMS  #ServantLeadership

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In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Julie Brinkman, CEO of Beyond, to explore how the company is transforming the way property managers approach pricing and profitability.

From dynamic pricing to market intelligence, Beyond has become a vital tool for short-term rental professionals looking to scale sustainably and outperform their competition. Julie shares how the company empowers property managers with smarter data, automation, and real-time insights to "beat the market"—no matter what that market looks like.

Key Topics Discussed:

1️⃣ Julie’s unique path to leadership and the lessons learned from her mother’s resilience

2️⃣ The evolution of revenue management in vacation rentals

3️⃣ How Beyond's tools help property managers maximize revenue while saving time

4️⃣ Lessons learned navigating COVID-19 and coming out stronger

5️⃣ The unique challenges of pricing single-unit properties vs. hotels

6️⃣ How global expansion is shaping Beyond's product innovation

7️⃣ The critical role of empathy, culture, and customer feedback in tech development

Julie also touches on the importance of industry collaboration, the rising need for smarter pricing strategies, and why AI alone isn’t enough to drive revenue in a human-centered business.

If you're a property manager, tech enthusiast, or hospitality professional looking to stay ahead in a competitive market, this conversation is packed with insight and inspiration.

Connect with Julie:

LinkedIn: http://linkedin.com/in/jrbrinkman/ 

Website: https://www.beyondpricing.com/ 

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie

Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.

#vacationrentals #revenuemanagement #shorttermrentaltech

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In this soul-stirring episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Brittany Blackman, former vacation rental business owner turned leadership coach and founder of Discover Freedom. Brittany gets real about what it took to walk away from the business she built and loved, after realizing that outward success came at the cost of her inner peace.

She opens up about her battle with burnout, the pressure to be everything to everyone, and how learning to set boundaries — and say no — led her to a life of greater alignment, fulfillment, and purpose. Now on a mission to help others do the same, Brittany shares how she's using her story and her coaching practice to support leaders in the vacation rental industry who are ready to rewrite their own rules.

Whether you're feeling stretched too thin, stuck in hustle mode, or simply ready to reconnect with your “why,” this episode is a powerful reminder that saying no is often the first step in saying yes to the life you actually want.

Key Topics Discussed:

1️⃣ Brittany’s leap into vacation rental entrepreneurship during the pandemic
2️⃣ What success really looks like and why it sometimes means walking away
3️⃣ How burnout led her to a life coach, self-work, and a values reset
4️⃣ The emotional impact of people-pleasing and perfectionism in leadership
5️⃣ Why boundaries are essential (not selfish)
6️⃣ The mindset shift behind Discover Freedom
7️⃣ What it means to lead, and live, with intention

Connect with Brittany:
LinkedIn: https://www.linkedin.com/in/brittany-blackman-384141216/
Website: https://discoverfreedom.life/

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie

Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.

#vacationrentals #leadership #burnout

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