Alex & Annie: The Real Women of Vacation Rentals

Send us a message!Is your short-term rental business growing, or just getting harder to manage?In this episode, we sit down with Patrick Stewart, CEO of Grand Welcome, to explore how franchising offers property managers a scalable and sustainable path to success in today's competitive STR market.Grand Welcome is one of the fastest-growing franchise-based vacation rental management companies in the U.S. The brand provides local operators with the tools, systems, and support they need to grow efficiently while delivering exceptional guest experiences and building strong homeowner relationships.With a background in fashion retail franchising, Patrick shares how those same principles of consistency, structure, and support can transform how short term rental rental businesses operate. At Grand Welcome, his mission is to help local operators grow profitably, simplify their operations, and build a business they enjoy running.Key Topics Discussed:1️⃣ Why franchising is a smart strategy for scaling in the vacation rental industry2️⃣ How Grand Welcome reduces operational load in guest services, pricing, and tech decisions3️⃣ Ways the model supports both new and experienced operators4️⃣ Approaches to navigating regulation, owner demands, and market shifts5️⃣ The role of shared best practices and peer collaboration in franchise success6️⃣ Grand Welcome's current trajectory and upcoming international expansionWhether managing 20 properties or 200, this episode offers a new perspective on what it means to scale. With the right partner, growth becomes more strategic, more profitable, and far less overwhelming.Connect with Patrick & Grand Welcome:LinkedIn: https://www.linkedin.com/in/patrickstewartceo/ Website: https://www.grandwelcomefranchise.com/Exclusive Offer to Alex & Annie Listeners: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/jessica-singer-grandwelcome/intro#vacationrentals #franchisebusiness   #propertymanagement 

Send us a message!In this week's episode, we're taking you back to Miami Beach for a special look at one of the most talked-about events in the industry this year, the 2025 VRMA Executive Summit.It's been a few weeks since the event, but the insights we gathered still feel just as relevant. Alex & Annie bring you candid interviews with some of the brightest and most respected voices in the vacation rental industry to talk through the wins, the growing pains, and the ideas shaping how we lead and grow in this business.Featuring interviews with:Tom Goodwin – CEO of Mountain Laurel Chalets, on co-chairing the summit, uniting vendors and PMs, and leading with intention.Rachel Alday – Co-founder of Abode Luxury Rentals, reflecting on curating content that builds stronger industry conversations.Sarah Bradford – Industry veteran, educator, and consultant, sharing candid “diary entries” from her 20-year career, and the lessons behind them.Valerie Gangas – Founder & CEO of Juniper Holiday + Homes, on fast growth, partnerships, and the power of mentorship.Patrick Stewart – CEO of Grand Welcome, explaining how franchising can help operators scale smart and reclaim their time.Steve Trover – CEO of Better Talent, discussing frontline hiring challenges, team dynamics, and how to embrace AI without fear.Jeff Iloulian – Founder of HostGPO, highlighting how smart procurement systems are helping operators work more efficiently at scale.Whether you were in the room or just hearing the buzz, this episode captures the vibe, vision, and voices that makes this year's VRMA Executive Summit the best one yet!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=AApod25Get 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 #VRMAexecutivesummit2025

Send us a message!When media veteran James Varley stepped away from a decade-long career working on the FIFA World Cup, he had no idea that a single Airbnb stay would spark his next chapter: empowering short-term rental hosts through education.In this episode, James joins us to share how that experience and the glaring lack of accessible resources for new hosts led to the creation of Host Planet, one of the UK's fastest-growing media platforms for STR professionals.This conversation hits close to home for Alex & Annie, who started their podcast with the same mission: to bridge the information gap in the vacation rental industry. Together, they dive into why so many hosts still struggle to find trusted guidance and how platforms like Host Planet and the Alex & Annie Podcast, among others, are helping change that by delivering clear, practical content that hosts can truly put to use.Key Topics Discussed:00:00:00 Intro00:04:04 From global media to local hosting: James' unexpected pivot  00:09:46 Podcasting as a tool for connection and collaboration  00:14:31 The blind spots new hosts face and why dynamic pricing was his wake-up call  00:18:43 Shared values with Alex & Annie: education, accessibility, and transparency  00:20:40 The rise of Host Planet and its mission to offer free, valuable content  00:26:27 Behind the scenes of UK-based STR events and future expansion  00:36:16 The challenges and opportunities of growing media platforms in STRConnect with James:LinkedIn: https://www.linkedin.com/in/jdsvarley/ Website: https://www.hostplanet.club/ 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/jessica-singer-grandwelcome/intro #vacationrentals #shorttermrentals #propertymanagement

Send us a message!What happens when one of the world's most trusted hotel brands steps into the vacation rental space?In this episode, we're joined by Jane Gavin (Senior Director of Brand Marketing & Guest Experience) and Keven Wishard (Senior Director of Global & Continent Operations) from Homes & Villas by Marriott Bonvoy.With decades of hospitality experience between them, Jane and Keven take us inside Homes & Villas by Marriott Bonvoy's bold approach to short-term rentals. One built on consistency, elevated design, professional management, and the power of one of the largest loyalty programs in the world.If you've ever wondered how Homes & Villas selects properties, enforces its standards, or attracts millions of Bonvoy members to luxury homes, this conversation will give you a whole new understanding of what it means to raise the bar in vacation rentals.Key Topics Discussed:1️⃣ Homes & Villas' unique position at the intersection of hotels and vacation rentals2️⃣ How trust, consistency, and personalization drive guest satisfaction3️⃣ What Homes & Villas' brand standards really look like for property managers4️⃣ The power of Bonvoy's 200M+ members to drive bookings5️⃣ “Curated Collections” and how Homes & Villas highlights one-of-a-kind stays6️⃣ Why professional management is non-negotiable on the platform7️⃣ How Homes & Villas is helping raise the bar for the entire STR industryConnect with Jane:LinkedIn: https://www.linkedin.com/in/jane-gavin/ Connect with Keven:LinkedIn: https://www.linkedin.com/in/kevenwishard/ 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=AApod25Get 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 #HomesandVillasbyMarriottBonvoy, 

Send us a message!In our first-of-the-month bonus episode, we are joined by Orlie Benjamin, founder and CEO of Lasoh, a marketing technology platform designed to help vacation rental operators own their guest relationships and drive direct revenue. Lasoh provides a branded digital guest portal and integrated CRM that allows operators to engage with guests from the moment of booking, offer upsells, and run smart, automated campaigns.Orlie shares how her background in corporate marketing and her own experience as a vacation rental operator shaped her approach to building Lasoh, and how it's helping operators take back ownership of their guest experience in a platform-dominated landscape.Key Topics Discussed:1️⃣ Why guest communication should begin at booking, not check-in2️⃣ How Lasoh helps operators deliver a more cohesive and elevated digital experience3️⃣ Navigating Airbnb's restrictions while still building direct guest relationships4️⃣ The role of retention marketing in improving occupancy and profitability5️⃣ Lessons from corporate hospitality that apply to short-term rentals6️⃣ How operators can build their own ecosystem for upsells and experiences7️⃣ The future role of AI in guest communication and CRM8️⃣ Why operators of all sizes need to think like brands, not just businessesConnect with Orlie:LinkedIn: http://linkedin.com/in/orliebenjamin/ Website: https://lasoh.io/ 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 #guestexperience

Send us a message!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 rentals2️⃣ Common blind spots property managers face when it comes to fraud and chargebacks3️⃣ How modern checkout options like Apple Pay, Pay Later, and Venmo are shaping guest expectations4️⃣ What property managers can do to protect profits and streamline payouts5️⃣ The importance of industry-specific tools for high-risk booking scenarios6️⃣ Lessons learned from OTAs, hurricanes, and helping PMs stay financially stable7️⃣ What operators should ask when choosing a payment partner8️⃣ The real cost of ignoring risk and complianceConnect 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

Send us a message!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 franchise2️⃣ How Dennis and Shahar aligned on values, leadership, and long-term vision3️⃣ What property managers can learn about letting go to grow4️⃣ The operational and cultural challenges of integrating a new team and brand5️⃣ How Casiola approaches expansion without sacrificing focus6️⃣ Why the traditional "do it all" mindset often leads to burnout in STR7️⃣ How Dennis views focus as a competitive advantage8️⃣ Why Shahar sees clarity as a form of leadership9️⃣ What role AI and automation will play as Boom continues to scaleYou'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

Send us a message!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 data2️⃣ Why summer 2025 bookings are slower, especially in budget and urban segments3️⃣ Hotels gaining share in cities as STR growth is restricted by regulation4️⃣ Supply growth slows across most markets and what that means for operators5️⃣ Signs of guests trading down, shortening trips, and delaying decisions6️⃣ The impact of fewer Canadian and European travelers this year7️⃣ Airbnb's urban inventory problem and the increasing presence of hotels on OTAsJamie 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

Send us a message!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 leadership2️⃣ Why outdated ideas of success often lead to burnout and disconnection3️⃣ What it means to “rebel” against norms without being loud about it4️⃣ The power of journaling, mindfulness, and small daily choices5️⃣ How to lead with legacy in mind and why it starts with youThis 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

Send us a message!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 VRNationOrlie Benjamin – Founder of LasohDylan Bozarth – General Manager of 30A EscapesTera Lorimer – Founder of Luxury Getaways and VRNation Board MemberHeather Van Wie – Founder of Cottages on the Key and VRNation Board MemberNicholas Wegener & Roy Collins – Founders of SendSquaredAnne Gardner – Executive Director at VRMAWhether 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

Send us a message!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 him2️⃣ The evolution of Booking.com's vacation rental strategy3️⃣ Why connectivity partners like NextPax play a key role in host success4️⃣ How Booking.com is supporting both enterprise and mid-sized property managers5️⃣ What makes listings convert: content, rate plans, and smart distribution6️⃣ The redesign of their payment system to solve real host pain points7️⃣ How generative AI is helping streamline guest communication8️⃣ Loyalty, trust, and the value of high-frequency guests9️⃣ The tools and resources Booking.com offers to support property managers at scaleConnect 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

Send us a message!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 trajectory2️⃣ Why scaling isn't always the answer—and what comes next3️⃣ The creative power of letting go of control4️⃣ What it really means to lead with authenticity5️⃣ How retreats are reshaping the future of leadership and hospitality6️⃣ Why personal breakthroughs often unlock professional successIf 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

Send us a message!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 rentals2️⃣Why servant leadership is at the core of his management style3️⃣How 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 retention5️⃣Track's approach to product development: build, buy, or partner6️⃣The role of AI in scaling support and internal operations7️⃣What true team engagement looks like—and why it mattersBoogie 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/alexandannieReady to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.#VacationRentals  #TrackPMS  #ServantLeadership

Send us a message!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 resilience2️⃣ The evolution of revenue management in vacation rentals3️⃣ How Beyond's tools help property managers maximize revenue while saving time4️⃣ Lessons learned navigating COVID-19 and coming out stronger5️⃣ The unique challenges of pricing single-unit properties vs. hotels6️⃣ How global expansion is shaping Beyond's product innovation7️⃣ The critical role of empathy, culture, and customer feedback in tech developmentJulie 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/alexandannieReady to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.#vacationrentals #revenuemanagement #shorttermrentaltech

Send us a message!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 pandemic2️⃣ What success really looks like and why it sometimes means walking away3️⃣ How burnout led her to a life coach, self-work, and a values reset4️⃣ The emotional impact of people-pleasing and perfectionism in leadership5️⃣ Why boundaries are essential (not selfish)6️⃣ The mindset shift behind Discover Freedom7️⃣ What it means to lead, and live, with intentionConnect 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#vacationrentals #leadership #burnout

Send us a message!In this special episode, Alex & Annie sit down with the original queens of vacation rentals: three powerhouse women who helped shape the industry from the ground up. Meet Jeanne Dailey (Founder & CEO, Newman-Dailey Resort Properties), Valerie Hawkins (Co-Owner & CEO, Perdido Key Realty), and Audrey Miller (Co-Founder & CFO, Cottage Connection of Maine) - each with a story full of grit, heart, and game-changing innovation.From starting with whiteboards and spiral notebooks to pioneering tech adoption and leading through legislative battles, these trailblazers reveal how they built thriving companies in a male-dominated industry - before vacation rentals were even “a thing.”Key Topics Discussed:1️⃣ Jeanne Dailey's Story2️⃣ Valerie Hawkins' Story3️⃣ Audrey Miller's Story4️⃣ The Early Days of Vacation Rentals5️⃣ First Software, Systems & Tech Innovation6️⃣ Being Women in a Male-Dominated Industry7️⃣ Finding Community in the Industry8️⃣ Early Networking, Software Choices, and Mentors9️⃣ The First Leap into Property Management Software

Send us a message!In this episode, Alex & Annie sit down with Jason Gann, a well-established figure in vacation rentals who has carved out a unique path as both a sales executive and an emerging comedic talent. Jason takes us through his fascinating career journey - from selling hair-cutting shears to stepping into the world of vacation rental technology, navigating the fast-changing landscape of property management software, and now leading conversations around revenue management at Beyond Pricing.Jason shares heartfelt insights on how personal branding, humor, and authenticity have helped him build meaningful industry relationships. He also discusses his upcoming role as the co-host of VR Nation, how imposter syndrome almost held him back from stepping into the spotlight, and why embracing vulnerability has become a powerful tool in his career.Key Topics Discussed:1️⃣Jason's transition from the beauty industry to vacation rentals.2️⃣The rapid evolution of vacation rental technology over the past decade.3️⃣The importance of personal branding and authenticity in career growth.4️⃣How humor and content creation helped Jason stand out in the industry.5️⃣Insights into revenue management and dynamic pricing strategies.6️⃣The challenges of imposter syndrome and how Jason overcame them.7️⃣Behind the scenes of Jason's viral ‘Finish the Lyric' video at industry events.8️⃣What to expect from VR Nation 2024, including Jason's role as co-host.Connect with Jason:LinkedIn: https://www.linkedin.com/in/jason-gann/Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.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 #revenuemanagement #personalbrand

Send us a message!As the hospitality industry evolves, guest screening and verification have become essential components of a safe and seamless guest experience. In this episode, we sit down with Ela Mezhiborsky, President and Co-Founder of AutoHost, to explore how cutting-edge technology is reshaping the way hotels and short-term rental operators manage risk, prevent fraud, and enhance security.Ela shares her insights on the growing role of AI and cybersecurity in guest verification, the challenges of "bad AI" in fraud prevention, and the regulatory changes driving the need for stronger screening solutions. From mandatory ID checks to advanced biometric verification, this conversation unveils the future of trust and safety in hospitality.Key Topics Discussed:1️⃣ The Evolution of AutoHost & Guest Screening2️⃣ The Role of AI in Fraud Detection & "Bad AI" Risks3️⃣ Regulatory Changes & Compliance Trends4️⃣ Hotels vs. Short-Term Rentals: Who's Leading in Security?5️⃣ The Future of Guest Verification & Embedded Security Solutions6️⃣ Addressing Human Trafficking & Ethical Responsibility7️⃣ Where AutoHost is Headed Next8️⃣ Final Thoughts & How to Connect with ElaConnect with Ela:LinkedIn: https://www.linkedin.com/in/elamezhiborsky/ Autohost Website: https://www.autohost.ai/ Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.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#guestscreening #vacationrentals #fraudprevention

Send us a message!We've got BIG news to share! In this special bonus episode, we welcome back industry powerhouse Amy Hinote to reveal all the exciting details about the 2025 Women's Summit!What better time to celebrate this announcement than during International Women's Day on March 8, 2025? This global day of recognition honors the achievements of women in every industry—including the incredible women shaping the vacation rental space. And what better way to continue that celebration than by gathering in person this August?Taking place August 19-21, 2025, at the historic Francis Marion Hotel in Charleston, SC, the Women's Summit has become a must-attend event, bringing together property managers, vendors, thought leaders, and trailblazing women from across the industry. Don't miss out on this exclusive update from Amy Hinote as she shares insider details on what to expect at this year's event!Key Topics Discussed:1️⃣ The Women's Summit 2025 – What to Expect & Why You Should Attend2️⃣ Keynote speakers3️⃣ The event's focus on mentorship, leadership, and career growth4️⃣ How the summit fosters cross-generational conversations in the industry5️⃣ An inside look at the session tracks6️⃣ Volunteer and Sponsorship Opportunities – How to Get InvolvedConnect with Amy Hinote:LinkedIn: https://www.linkedin.com/in/amymutual/ Register for the VR Women's Summit and use code ALEXANDANNIE at checkout to save $100 on your registration: https://vrwsummit.com/ Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.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#WomensSummit2025 #VacationRentals #ShortTermRentals

Send us a message!In this episode, we are joined by some of the most influential leaders in the vacation rental industry. From VRMA (Vacation Rental Management Association), we welcome Executive Director Anne Gardner and Chair of the Board of Directors Jodi Refosco. Representing VR Nation, we have President Matt Tisdall and Executive Director Heidie Henriksen. Together, we dive into the exciting evolution of both organizations, their upcoming conferences, and the importance of collaboration in shaping the future of vacation rentals.With two major events on the horizon: the VRMA Foundations: Frontline Excellence Training in Savannah and the VR Nation National Conference in Austin, we discuss what attendees can expect, how these events foster industry-wide education, and why networking is more critical than ever. Beyond conferences, the conversation highlights the growing need for unified advocacy, support for small and large operators, and the push toward greater professionalization of the industry.Whether you're a seasoned property manager, a new entrant in short-term rentals, or a vendor supporting this space, this episode is packed with valuable insights into where the industry is headed and how we can all work together for collective success.Key Topics Discussed:1️⃣Introducing the panel: Key leaders from VRMA & VR Nation2️⃣What makes each association unique & where they collaborate3️⃣Upcoming conferences: What to expect in Savannah & Austin4️⃣The importance of advocacy and professionalization in vacation rentals5️⃣How VRMA & VR Nation are supporting both small and large operators6️⃣The role of vendors & suppliers in the evolving vacation rental landscape7️⃣Educational initiatives for short-term rental operators8️⃣The need for industry-wide collaboration in an ever-changing marketUpcoming Events Mentioned:VRMA Foundations: Frontline Excellence Training  – April 14-15, 2025 | Savannah, GAVR Nation National Conference – April 27-28, 2025 | Austin, TXVRMA Executive Summit – May 28-30, 2025 | South Beach, FLConnect with our Guests on LinkedIn:Matthew Tesdall: https://www.linkedin.com/in/matthewtesdall/Heidie Henriksen: https://www.linkedin.com/in/heidieh/ Anne Gardner: https://www.linkedin.com/in/anne-gardner-mba-cae/ Jodi Refosco: https://www.linkedin.com/in/jodirefosco/ Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.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 #vrma #vrnation

Send us a message!In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Expedia Group, to discuss VRBO's vision for 2025 and beyond.Tim shares insights on VRBO's evolving strategy, including how the platform has transformed since its transition from HomeAway, its commitment to professional property managers, and its focus on delivering exceptional guest experiences. He also provides an inside look at VRBO's marketing direction, technology advancements, and key initiatives that will shape the future of the vacation rental industry.We explore how VRBO is leveraging its One Key loyalty program, improving traveler targeting, and refining its platform to drive better results for property managers. Plus, Tim gives a candid take on the OTA landscape, regulatory challenges, and the evolving role of trust and safety in the industry.For anyone looking to stay ahead in the short-term rental space, this episode is packed with valuable insights from one of the industry's top leaders.Key Takeaways: 1️⃣ The evolution from HomeAway to VRBO and what it means for property managers2️⃣ How VRBO is enhancing technology to create a seamless experience for partners and travelers3️⃣ The impact of One Key and how it's shaping guest loyalty4️⃣ VRBO's marketing strategy for 2025 and adapting to the changing digital landscape5️⃣ Trust, safety, and guest verification: How VRBO ensures quality stays6️⃣ What's next for VRBO's promotions suite and marketplace design7️⃣ How VRBO is engaging in advocacy efforts and regulatory discussions to support the industryConnect with Tim Rosolio: https://www.linkedin.com/in/tim-rosolio-434b2a98/Learn more about VRBO's One Key program: https://partner.expediagroup.com/en-us/solutions/distribute-your-inventory/one-key-travel-rewards Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.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 #vrbo

In this episode, we sit down with Wil Slickers - an industry legend who transformed a single podcast into Hospitality.FM, a full-fledged media company. Wil shares how he scaled his brand from a passion project into a thriving network of nearly 40 hospitality-focused podcasts.Wil discusses the challenges and breakthroughs in building a media empire, from securing sponsorships to expanding into new content formats like video, book publishing, and event management. He also shares his insights on why podcasts alone aren't enough - you need an entire content ecosystem to drive engagement, audience growth, and monetization.Whether you're a hospitality professional, content creator, or entrepreneur looking to scale your brand, this episode is packed with valuable lessons on business growth, media strategy, and the future of hospitality content.Key Topics Discussed:1️⃣The importance of media in shaping the hospitality industry.2️⃣How podcasting serves as a platform for industry education and networking.3️⃣Monetization strategies for podcasters and media creators.4️⃣ The shift from traditional hospitality marketing to digital-first strategies.5️⃣ Wil's personal journey and the lessons he's learned in media entrepreneurship.6️⃣ The future of industry conferences and the role of intimate, curated events.7️⃣How Hospitality.FM is providing value to creators and listeners alike.Connect with Wil:LinkedIn: https://www.linkedin.com/in/wil-slickers/ Hospitality FM: https://hospitality.fm/ Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/ to learn more.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 #hospitalitypodcast #hospitalitymarketing

In this special episode, Alex & Annie take you to the heart of the Track NEXT25 Conference, TravelNetSolutions' premier annual conference, held in the vibrant city of Nashville. This annual user conference brings together company representatives, executives, vendors, and customers for a blend of fun, fellowship, and educational sessions designed to maximize the value of Track software. Alex teamed up with Justin Panzer, VP of Marketing for TravelNet Solutions, to delve into what made this year's conference a standout. They discuss the event's engaging format, which included inspiring keynote speakers, hands-on workshops, peer-led discussions, and insights into the latest industry innovations.Alex & Annie also bring you exclusive conversations with industry experts, innovators, and property managers, offering insights into the latest trends, tech advancements, and strategies shaping the vacation rental industry.Key Topics Discussed:1️⃣ Michael Ohanian (VP of Product Management, Track) – The power of Track's in-house Distribution Manager and how it's helping property managers optimize revenue in tough economic times.2️⃣ Kelly McNeil (Senior Strategic Program Director, Track) – Breaking down Track's Payments System, how it's reducing processing fees, and making transactions seamless for property managers.3️⃣ Lui King (Safely) & Ashley Ching (Inhaven) – A new partnership that's innovating linen insurance to protect properties against guest-related damages.4️⃣Rosita Hernandez (Product Manager, Track) – An exclusive look at Track's Owner Portal revamp and mobile-first approach, improving transparency and communication for property managers and owners alike.5️⃣ David Stephens (Lead Data Scientist, Track) – How AI and dynamic pricing are driving smarter revenue decisions in vacation rentals.6️⃣ Daniel Leifield (Key Data) – The importance of real-time industry data and insights into what top-performing property managers are doing differently.7️⃣Tim Schutts (VP of Sales, Track) – How Track is positioning itself to bridge the gap between vacation rentals and traditional hotels, catering to hybrid hospitality models.Connect with our Guests:Justin PanzerLinkedIn: https://www.linkedin.com/in/justinpanzer/ Michael OhanianLinkedIn:https://www.linkedin.com/in/michael-ohanian/ Kelly McNeilLinkedIn: https://www.linkedin.com/in/kelly-mcneil-18614886/ Rosita HernandezLinkedIn: https://www.linkedin.com/in/rositadhernandez/David StephensLinkedIn: https://www.linkedin.com/in/david-stephens-bb54241b5/ Tim SchuttsLinkedIn: https://www.linkedin.com/in/timschutts/ Lui King & SafelyLinkedIn: https://www.linkedin.com/in/lui-king/ Website: https://safely.com/Ashley Ching & InhavenLinkedIn:https://www.linkedin.com/in/ashley-ching-7569a5240/ Website: https://inhaven.com/Daniel LeifeldLinkedIn:⁠https://www.linkedin.com/in/daniel-leifeld-87a31547/⁠Ready to take your operations to the next level? Visit⁠⁠https://tnsinc.com/podcasts-alex-and-annie/⁠ ⁠ to learn more.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#TrackNEXT25 #VacationRentals #PropertyManagement

In this week's episode, we sit down with two of the most influential voices in the short-term rental (STR) advocacy space - David Krauss, CEO & Founder of Rent Responsibly, and Alexa Nota, COO & Co-Founder. With regulations and housing discussions at the forefront of industry challenges, Rent Responsibly is leading the charge in empowering hosts, owners, and managers to unite, educate, and advocate for fair policies. From community-building to data-driven insights, David and Alexa share how they're working to close the information gap between policymakers and operators, ensuring that STR professionals have a seat at the table. Key Topics Discussed: 1️⃣ Strengthening the STR community through advocacy and education. 2️⃣ Addressing policy misconceptions and affordability concerns. 3️⃣ Why hosts must engage in local and state policy discussions. 4️ Key findings from Rent Responsibly's 130,000+ data points. 5️⃣ How state and local groups are organizing for policy impact. 6️⃣ Combating misinformation in STR regulations. 7️⃣ Why local hosts' voices matter in regulatory decisions. 8️⃣ How hosts can partner with Chambers of Commerce & DMOs. 9️⃣ Debunking the idea that banning STRs solves housing issues.

In this week's episode, Alex and Annie sit down with Fred Boothby, CEO of Enjoy Unique Stays, to explore how he's breaking the mold in the vacation rental industry. What started as a small side business has grown into a thriving portfolio of 140+ properties across multiple states, redefining what it means to create experiential stays that go beyond the ordinary. Fred shares the bold strategies and innovations that have shaped his success, from crafting unique guest experiences to navigating the challenges of multi-market property management. He also dives into the hard lessons learned from industry risks like natural disasters, the power of branding and culture, and the role of technology in streamlining operations. Whether you're a property manager, real estate investor, or hospitality enthusiast, this episode is packed with game-changing insights to help you stay ahead in an evolving industry. Key Topics Discussed: 1️⃣ Fred's journey to founding Enjoy Unique Stays 2️⃣ The importance of branding, culture, and team alignment in scaling a hospitality business. 3️⃣ Lessons from hurricane recovery and business resilience. 4️⃣ Fred's hands-on experience with Streamline, Guesty, and Boom, and the role of technology in managing diverse properties 5️⃣ Why secondary and tertiary markets offer hidden opportunities 6️⃣ The rise of experiential stays in hospitality Connect with Fred Boothby: LinkedIn: https://www.linkedin.com/in/fred-boothby-777096a/ Connect with Enjoy Unique Stays: LinkedIn: https://www.linkedin.com/company/unique-stays-llc/ Instagram: https://www.instagram.com/_enjoyuniquestays_/?hl=en Website: https://www.enjoyuniquestays.com/ Want to optimize your guest experience? Exclusive for our listeners: Get a free guest journey analysis at https://www.happyguestofficial.com/alexandannie Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/ to learn more. #ExperientialStays #VacationRentals #HospitalityIndustry

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we're thrilled to welcome back Alex Shapiro, CEO and co-founder of CanMonkey. Alex joins us to share exciting updates on how his company has continued to revolutionize trash management for vacation rentals and beyond. CanMonkey, which started as a bootstrap idea in 2018, now operates in 28 states and services over 5,000 properties across 350 cities. With innovative solutions, a gig-based workforce, and a deep understanding of industry challenges, Alex and his team are solving problems many didn't even know had solutions. This conversation dives deep into the evolution of CanMonkey from a simple service idea to a full-fledged logistical technology company. From their distinctive brand strategy to their ability to tackle city regulations and homeowner frustrations, Alex offers insights that are not just valuable for vacation rental operators but for any entrepreneur looking to scale a business. Key Topics Discussed: ⚡ Can Monkey's Origin and Growth ⚙ How Can Monkey Solves Trash Management Challenges

It's a milestone moment for Alex & Annie: The Real Women of Vacation Rentals as we celebrate our 200th episode together with some of the most brilliant and influential podcasters in the vacation rental industry. To make this occasion extra special, Amber Hurdle and Travis Wilburn take over hosting duties, flipping the script by putting Alex & Annie in the guest seats. This episode is a tribute to the journey of not just Alex & Annie but the entire podcasting community that amplifies the voices of vacation rental professionals, pioneers, and enthusiasts. Joining the celebration are some of the industry's key influencers: Sarah and T, Wil Slickers, Tom Goodwin, Amber Hurdle, and Travis Wilburn. Together, they represent a collective history of over 1,100 episodes and more than 6 million listeners. This lively and inspiring conversation delves into the trends shaping the vacation rental industry, the origins of some of your favorite podcasts, and the transformative power of podcasting on careers and lives. Key Topics Discussed:

In this week's episode, we are thrilled to welcome back Terry Whyte, owner of Anna Maria Island Beach Rentals and a renowned expert in vacation rental technology and operations. As one of the leading voices in the vacation rental industry, Terry dives into the evolving landscape of vacation rental software, sharing his predictions and practical insights on what's driving innovation in the field. From the rise of "all-in-one" solutions to the growing dominance of CRM platforms, this episode sheds light on the tools and strategies reshaping how property managers operate and thrive in an increasingly competitive market. Terry also shares his firsthand experiences navigating the challenges of hurricanes, offering valuable advice on resilience, recovery, and rebuilding trust with guests. Whether you're a property manager, tech enthusiast, or vacation rental professional, this episode is packed with actionable takeaways to help you stay ahead in a dynamic industry. Key Topics Discussed:

Welcome to the first episode of the year! What better way to kick off 2025 than with our tradition of reflecting on the past year's highlights and setting an inspiring tone for the year ahead. In this episode, Alex & Annie revisit the most listened-to episodes of 2024, unveil their “Words of the Year” for 2025, and outline their bold goals and exciting plans for the months to come. Whether you're looking to reflect on your own journey, draw inspiration for the year ahead, or stay updated on the latest trends in vacation rentals, this episode is packed with valuable insights, actionable strategies, and the motivation you need to start your year strong. Key Topics Discussed:

In this week's episode, we're thrilled to welcome back Tom Goodwin, CEO of Mountain Laurel Chalets and host of For the Love of Gatlinburg Podcast. Tom shares insights into his family-run vacation rental business in Gatlinburg, which has been a beloved destination for over 50 years. We dive into his journey of preserving the essence of Gatlinburg through his podcast and discuss how it celebrates the community's rich heritage and unique stories. Tom also gives an update on Mountain Laurel Chalets, including the lessons learned from a recent business acquisition and how they've grown their portfolio while staying true to their brand's values. From creating meaningful guest experiences to forming deep community ties, this episode is packed with inspiration for anyone in the vacation rental or hospitality industry. Key Topics Discussed:

In this special throwback episode, we revisit a powerful conversation with Amber Hurdle, CEO and founder of Employer Brand Central. Originally aired around this time last year, this episode marks a pivotal moment for Alex & Annie as they navigated career transitions and personal growth. Amber's wisdom, energy, and insights set the tone for what was to come, not just for the hosts, but for countless listeners. Amber reflects on the importance of building strong personal and employer brands, overcoming self-doubt, and unlocking potential by “getting out of your own way.” With actionable advice and heartfelt stories, this episode will resonate with anyone standing at the edge of a new beginning or deep in the trenches of change. Whether you're rethinking your career, building your personal brand, or simply seeking inspiration, this episode is packed with insights to guide you forward. Key Topics Discussed:

This week, we're thrilled to welcome back John Hildebrand, founder of Hilde Homes and a leading advocate in the short-term rental industry. From his early days as a property manager to becoming a leading voice in vacation rental advocacy and education, John shares his inspiring journey with authenticity, humor, and valuable insights. With firsthand experience navigating the challenges of hosting, John highlights the vital role of advocacy in driving positive change for operators, guests, and local governments. He discusses how grassroots efforts, statewide coalitions, and collaboration with groups like Rent Responsibly are helping to elevate the industry's standards while fostering more balanced and fair regulations. Key Topics Discussed:

In this week's episode, we sit down with Declan McGonigal, the dynamic owner-operator of My Beach Vacation Rentals, based in North Myrtle Beach. Declan's story is one of grit, growth, and ingenuity, as he shares how he went from managing just two properties to overseeing a thriving portfolio of 70 vacation rentals in just a few years. Declan opens up about the lessons he's learned along the way, from the early challenges of starting his business to the strategies that helped him scale successfully. He shares how realtor referrals and local meetups powered his growth, the role of technology in streamlining operations, and the importance of building a strong team. Whether you're a seasoned property manager or just starting out in the vacation rental industry, Declan's journey offers invaluable insights and actionable advice. Key Topics Discussed: ⚡ Transitioning from engineering to vacation rentals

In this week's episode, we sit down with Declan McGonigal, the dynamic owner-operator of My Beach Vacation Rentals, based in North Myrtle Beach. Declan's story is one of grit, growth, and ingenuity, as he shares how he went from managing just two properties to overseeing a thriving portfolio of 70 vacation rentals in just a few years. Declan opens up about the lessons he's learned along the way, from the early challenges of starting his business to the strategies that helped him scale successfully. He shares how realtor referrals and local meetups powered his growth, the role of technology in streamlining operations, and the importance of building a strong team. Whether you're a seasoned property manager or just starting out in the vacation rental industry, Declan's journey offers invaluable insights and actionable advice. Key Topics Discussed: ⚡ Transitioning from engineering to vacation rentals

Register at https://vrdarm.com/registration/ and get $200 off when you use the promo code alexannieVIP In this exciting episode, we are joined by the dynamic Amy Hinote, founder of the Vacation Rental Data and Revenue Management Conference (DARM). Amy shares her vision for DARM 2024, revealing exciting details about the venue, agenda, and the groundbreaking educational sessions planned for property managers and industry professionals. Tune in to learn about innovative strategies for revenue and marketing integration, the role of AI in the evolving tech landscape, and how to master direct booking strategies for long-term growth. Whether you're a seasoned attendee or new to DARM, this episode is packed with insights you won't want to miss. Key Topics Discussed:

In this episode, we sit down with Steve Turk, founder of Tangy Management, a vacation rental management company known for its unique hotel-inspired approach to hospitality. With over 24 years of experience in luxury hotels, Steve brings a fresh perspective to the vacation rental industry, blending high standards from the hotel world with the flexibility of short-term rentals. Steve shares the story of how he shifted from a career in luxury hotels to founding Tangy Management, and the unique value his team brings to the vacation rental market. Steve also discusses his journey as the host of Hospitality Mentor podcast, which he started as a way to connect with industry leaders and share insights about careers in hospitality. From this, he has grown a vibrant community and organized popular networking events. Steve opens up about the challenges of managing vacation rentals in competitive markets like Miami, adapting to market shifts, and the importance of building community among guests and property owners alike. Key Topics Discussed:

This week, we're coming to you live from the heart of Florence, Italy, where Alex & Annie attended Scale Italia 2024! In this special on-the-ground episode, we bring you a dynamic mash-up of conversations with some of the most influential figures in the vacation rental and property management industries. Hear firsthand perspectives from Italy's vibrant conference floor, where the future of global property management, tech trends, and regulatory changes in the short-term rental space were top of mind. From unique regulatory hurdles in Italy to the latest advancements in AI and PMS technology, this episode captures the pulse of Europe's growing vacation rental market. Join us as we sit down with conference organizers, tech innovators, and industry leaders to unpack the challenges and opportunities facing property managers worldwide. Key Topics Discussed:

In this special re-air of one of our most popular episodes, Alex & Annie brings together a powerhouse panel of industry experts, known as the OGs of the Panhandle. Our guests—James Olin, Steve Caron, Lino Maldonado, and Paul Wohlford—share invaluable insights from their decades-long journeys in the vacation rental industry, reflecting on where it all started, where it is now, and where it's headed. Episode Highlights: The Early Days: Travel back with our panel as they recount the challenges and successes that marked their early years in vacation rentals. Hear the stories of navigating uncharted territory with passion, resilience, and a vision for the future. The Industry Today: Explore how mergers, acquisitions, and new technologies are reshaping guest experiences and operations. Our experts discuss balancing innovation with the personal touch that defines hospitality and reveal the tech innovations that have made the biggest impact. Looking Ahead: The conversation shifts to the future, delving into topics like potential industry standardization, the role of larger players, and the value of a boutique approach. Hear insights on how advocacy and regulatory involvement are shaping what's next for vacation rentals. Key Takeaways:

In this special re-air of one of our most popular episodes, Alex & Annie revisit our insightful conversation with Tom Goodwin, CEO of Mountain Laurel Chalets. Tom's remarkable journey in the vacation rental industry, from unexpected beginnings to building a brand rooted in community, continues to inspire. Tom's Journey: Discover how Tom's unexpected entry into the vacation rental world, through his wife's family-run business in Gatlinburg, evolved into a thriving venture. His initial 18-month commitment turned into an 11-year commitment, filled with challenges and triumphs. Community and Branding: Explore Tom's insights into the profound impact of community involvement and branding in the hospitality industry. Learn how his diverse background seamlessly translated into revitalizing the Mountain Laurel Chalets brand. Looking to the Future: Tom shares his excitement for the future, including the acquisition of a new business and plans for a local podcast. Stay tuned as he promises to keep us updated on his journey throughout the year. Key Takeaways:

Exclusive offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & Annie listeners also receive free Jini for Property Managers.  Claim this offer here: ⁠⁠⁠https://www.ownerpoint.io/alex-and-annie⁠⁠⁠ - Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit ⁠⁠⁠⁠https://www.boomnow.com/⁠⁠⁠ to claim this limited-time deal! In this week's episode, we welcome back Dennis Goedheid, founder and CEO of Casiola Vacation Homes. Dennis returns to share exciting updates on his company's growth, including the launch of a new franchise model. Since its inception, the franchise has rapidly expanded into key markets, including Aruba, where Casiola has seen tremendous success. Dennis also dives into the challenges and opportunities in the vacation rental space, from navigating property management in international markets to the importance of local partnerships. He provides insight into Casiola's unique franchise approach, which aims to create a global brand for vacation rentals, much like Marriott did for hotels. The conversation touches on the critical issue of short-term rental regulations, with Dennis discussing his advocacy efforts in Florida and Aruba to ensure fair regulations that support both property managers and local communities. Key Topics Discussed:

Exclusive offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & Annie listeners also receive free Jini for Property Managers.  Claim this offer here: ⁠⁠https://www.ownerpoint.io/alex-and-annie⁠⁠ - Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit ⁠⁠⁠https://www.boomnow.com/⁠⁠ to claim this limited-time deal! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Ian Carter, the former CEO of Hilton International and current Chair of the Board for Watches of Switzerland, Eataly, The Boston University School of Hospitality and Administration, and Boom. Ian shares his remarkable career journey, from his early days at General Electric to leading Hilton International through its historic merger with Hilton Hotels Corporation. We also dive into the vacation rental market, where Ian reflects on the challenges and opportunities this sector presents, especially in comparison to his experience in the hotel industry. He highlights the increasing role of AI and technology in managing vacation rentals and the importance of personalizing guest experiences.  Key Topics Discussed:

Exclusive offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & Annie listeners also receive free Jini for Property Managers.  Claim this offer here: ⁠https://www.ownerpoint.io/alex-and-annie⁠ - Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit ⁠⁠https://www.boomnow.com/⁠ to claim this limited-time deal! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by Rebecca Ballart, COO of Rev & Research, a leading revenue management consulting firm for vacation rentals. Rebecca shares her deep insights into the current state of the vacation rental market, discussing the challenges and opportunities that property managers are facing as we head into 2024. We dive into the key trends, including increased supply, softening demand, and how international travel options are affecting domestic bookings. Rebecca provides actionable advice on navigating tough homeowner conversations, adjusting pricing strategies, and enhancing guest experiences to drive long-term success. Key Topics Covered: ⭐ The current challenges in vacation rental markets and strategies to stay ahead in 2024.

Exclusive offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & Annie listeners also receive free Jini for Property Managers.  Claim this offer here: https://www.ownerpoint.io/alex-and-annie - Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit ⁠https://www.boomnow.com/ to claim this limited-time deal! In this special 1st of the month bonus episode, Alex & Annie are joined by Ari Eryorulmaz, founder and CEO of Extenteam, to discuss their exciting new staffing program designed for vacation rental hosts of all sizes.  Ari shares insights into the company's journey, from humble beginnings as a side gig to becoming a leader in providing virtual staffing solutions for property managers worldwide. He highlights the evolution of staffing needs in the hospitality industry post-COVID and introduces Extenteam's newest service, Tailwind, which enables smaller operators to access professional staffing on a flexible, per-unit subscription basis.  This game-changing program is set to help hosts operate efficiently and elevate guest satisfaction, regardless of property size. Key Topics Discussed:

Exclusive offer for Alex & Annie listeners: Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit boomnow.com to claim this limited-time deal! In this week's episode, we're joined by Eric Moeller, the visionary founder and CEO of Freewyld, a brand creating nature-inspired cabin communities. Eric takes us on his entrepreneurial journey from real estate investment to building luxury short-term rental brands and developing Freewyld.  With decades of experience in real estate and vacation rentals, Eric has a fresh perspective on how to elevate the short-term rental experience. His passion for thoughtful design, personalized hospitality, and creating spaces that encourage guests to unplug from technology and reconnect with nature sets Freewyld apart from other rental brands. In this conversation, Eric breaks down how Freewyld combines modern amenities, reclaimed materials, and nature-centric properties to craft unforgettable guest experiences. Key Topics Discussed:

In this exciting episode, Alex & Annie sit down with Larry Hoffer, CEO of Rentalz, a company specializing in breakthrough growth solutions for vacation rental managers.  Larry takes us on a journey through his two-decade career, starting from a personal double-booking mishap in Vail, Colorado, to becoming a key figure in the vacation rental industry.  He shares how Rentalz, with its innovative services like OwnerPoint, ContactPoint, AnswerPoint and the recently launched TravelPoint, is driving exponential growth for property managers across North America. Key Topics Discussed:

In this week's episode, we sit down with Shahar Goldboim, CEO of Boom, to discuss the world's first AI-driven Property Management System (AiPMS). Shahar shares the story behind Boom's inception and how his passion for innovation in real estate led to the creation of a cutting-edge solution for property managers.  By blending AI with the complexities of property management, Boom is revolutionizing the way companies scale, optimize operations, and enhance the guest experience. Shahar also gives us an inside look at how Boom's AiPMS seamlessly integrates property management tasks like guest communication, work orders, review management, and upselling—all in one platform. Key Topics Discussed:

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex and Annie sit down with Heather Bayer, a veteran in the vacation rental industry.  Heather shares her journey from running a management training company in England to becoming a prominent figure in the vacation rental space. She discusses her current role as the Director of Training for the Vacation Rental Formula Business School and her experiences as a podcast host. Throughout the episode, the discussion touches on the importance of understanding different personality types and communication styles in the workplace, the challenges of online education, and the evolving landscape of networking and knowledge-sharing in the vacation rental industry. Key Topics Discussed:

In this special first-of-the-month episode, Alex and Annie bring back one of their most impactful discussions from June 2022, perfect for the peak of hurricane season. This re-airing of Episode 36 features Pete DiMaio from TravelBoom, who shares vital strategies for preparing vacation rental managers and hoteliers for potential disasters, particularly hurricanes. Pete walks through his comprehensive "Six P's of Disaster Planning," a methodical approach to ensure that vacation rental businesses and hotels are ready to handle the chaos and communication challenges that arise during a disaster. He emphasizes the importance of proper planning and the critical role of effective communication before, during, and after such events. Key Topics Discussed:

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are thrilled to welcome Rachel Alday, co-owner and co-founder of Abode Luxury Rentals. Rachel shares the fascinating journey of how she and her husband built a successful luxury vacation rental business that spans multiple high-end markets, including Park City, Jackson Hole, and Sun Valley. Rachel's story is one of perseverance, vision, and adapting to the ever-changing landscape of the vacation rental industry. From navigating the complexities of luxury property management to strategically expanding into new markets, Rachel shares the invaluable lessons she has learned along the way.  Key Topics Discussed: .

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Alexis Rivera Scott, the dynamic founder of Fairy Job Mom.  Alexis shares her journey from a career in hospitality sales to becoming a powerhouse on LinkedIn with over 81,000 followers. She opens up about her transition from traditional employment to entrepreneurship, the challenges she faced along the way, and the importance of building a personal brand. Key Topics Discussed: 

In this episode, we dive deep into the world of public relations with industry expert Jessica Gillingham, CEO and founder of Abode Worldwide. Jessica shares her unique journey into the vacation rental space, from her early days in Canadian tourism to launching her own booking platform, and eventually founding Abode Worldwide. She offers valuable insights into the role of PR in shaping brand narratives and building trust within the industry. Key topics discussed: