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PillowTalk Sessions

Jessica Gillingham and Kristian Lupinski

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Welcome to Pillow Talk Sessions, where we dive into the heartbeat of hospitality, lodging, and living—the places where hospitality and real estate meet. Hosted by Jessica Gillingham and Kristian Lupinski, we are your guides on a journey through the ever-evolving landscape of global lodging technology. From the cozy comforts of your favorite boutique hospitality lifestyle brand to the cutting-edge innovations shaping the future of urban living, we're here to explore it all. Join us as we unco ...
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With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.
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Welcome to How We Grow. Consider this your playbook for all things vacation rental, as we deep-dive into the latest hot topics, technology, and strategies, to help you take your vacation rental business to the next level. Hosted by industry veteran, Lynell Gordon.
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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 in…
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In this episode of The Vacation Rental Show: How We Grow, host Lynell Gordon is joined by Amber Hurdle, founder of Employer Brand Central. Together they explore: Maintaining employee engagement during change Emerging branding trends Creating a “Brand Bible” Challenges faced by women in business today Amber is the founder of Employer Brand Central, …
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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 entrepreneursh…
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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, we sit down with Zach Busekrus, Founder/CEO of StayWatch and host of the "Behind the Stays" podcast. Zach shares his unique journey into the short-term rental industry, f…
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In this episode of The Vacation Rental Show - How We Grow, host Lynell Gordon is joined by John Stokinger, Director of Sales at Direct. Together, they explore: The camaraderie and communication of the vacation rental industry How some industry conferences could be improved to focus on education and cost efficiency Why it’s crucial for property mana…
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In this episode of The Vacation Rental Show: How We Grow, host Lynell Gordon is joined by Michael B. Rubin, General Manager of Streamline Vacation Rental Software at Inhabit. Together, they explore: Streamline’s recent innovations How good customer feedback provides a solid foundation for future innovation The upcoming Streamline Summit Since the b…
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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 Welcome to our August 1st of the month bonus episode! Today, we welcome back Simon Lehmann, a seasoned expert in the vacation rental industry and the co-founder and CEO of AJL Atelier. Wit…
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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 & Annie are joined by Linny and Kyle Jones, the dynamic duo behind Dwell Luxury Rentals. Tune in to hear how they have transformed the vacation rental landscape in th…
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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 insightful episode of Alex & Annie: The Real Women of Vacation Rentals, we are thrilled to welcome Mark Lumpkin, Director of Sales for STR Cribs. Mark shares his journey from a Fl…
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In this episode of The Vacation Rental Show - How We Grow, host Lynell Gordon is joined by John An, Founder and CEO at TechTape and President at Ohana Stay. Together, they explore: Why there is technology fragmentation in the industry How to implement tech solutions Revenue management in 2024 John is Founder and CEO of TechTape, providing short-ter…
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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 Join Alex & Annie as they dive into an enlightening conversation with Margenett Moore-Roberts and Gia Sharp, key figures in the short-term rental advocacy scene in New York City. This epis…
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In this episode of How We Grow, host Lynell Gordon is joined by Brian Olson of Beachcomber Vacation Homes. Together, they explore: The increasing trend of shortened booking windows The rebranding of Northwest Vacation Rental Professionals to VR Nation Fostering a culture of trust in your team Brian is the Owner of Beachcomber Vacation Homes, offeri…
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In this episode of How We Grow, host Lynell Gordon is joined by Cara Shimizu of VR Decor. Together, they explore: How to make listing photos stand out Why you should make your property Instagrammable What colors rent well Cara is the owner of VR Decor, a specialist decorating company committed to helping short-term rental owners achieve maximum rev…
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Get your Scale Italia 2024 tickets here: https://www.tickettailor.com/events/scalerentalsitalia/1074426 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 week’s episode, Alex & Annie welcome the team behind the Scale Italia - Gian…
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In this episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by Scott Wiseman, CEO of Nocturne Luxury Villas. Scott brings a wealth of experience from his journey through the hospitality industry, from hotels to luxury tour operators, and now leading the charge in high-end vacation rentals. Scott's journey in hospitality began …
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In this episode of How We Grow, host Lynell Gordon is joined by Randy Hall of Liquid Life Vacation Rentals. Together, they explore: Marketing to new owners Hiring the right people as you grow Targeting the right areas for growth Randy is Owner and Team Leader of Liquid Life Vacation Rentals, bringing over 25 years of marketing and small business ex…
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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 are joined by Eric Goldreyer, the CEO and owner of BnBFinder. Eric shares his journey in the bed and breakfast and vacation rental industry, discussing his …
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In this episode of How We Grow, host Lynell Gordon is joined by Jessica Gillingham of Abode Worldwide. Together, they explore how to boost your reputation through: Crafting your own narrative Becoming an expert in the industry Communicating interesting information regularly with owners Jessica is Founder and CEO of Abode Worldwide, a specialist pub…
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In this episode of How We Grow, host Lynell Gordon is joined by Fred Boothby of Enjoy Unique Stays. Together, they explore: The value of mentorship across the vacation rental industry Why you should view each business operation as a separate entity The opportunities for inspiration that come from opening up your home In 2019, Fred co-founded Enjoy …
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Welcome to Pillow Talk Sessions, the podcast that dives into the heartbeat of hospitality, lodging, and living—the spaces where hospitality and real estate meet. Join your hosts, Kristian Lupinski and Jessica Gillingham, as they guide you through the ever-evolving landscape of global lodging technology. From the tech that supports the cozy comforts…
  continue reading
 
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 week’s episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by two powerhouse guests in the vacation rental space - Jason Sprenkle, CEO of Keydata, and Jacobie…
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In this episode of How We Grow, host Lynell Gordon is joined by Justin Ford of Breezeway. Together, they explore: Taking appropriate safety measures for hot tubs and pools Where the real risks lie with fire pits Guests’ increasing focus on safety Justin is the Director of Short-Term Rental Safety and Certification Programs Director at Breezeway, as…
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In this episode, Alex & Annie are joined, for the third time, by Marcus Rader, CEO and co-founder of Hostaway - the largest all-in-one solution for vacation rental property managers. Regulatory Challenges & Unique Perspectives Marcus shares candid insights from his recent travels, including staying in an "illegal" rental in New York City. He dives …
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In this episode of How We Grow, host Lynell Gordon is joined by Justin Ford of Breezeway. Together, they explore: Why accidents are so common in vacation rentals The most common causes of injuries and fatalities and how to prevent them The toxic mindset many are plagued with Justin is the Director of Short-Term Rental Safety and Certification Progr…
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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 sit down with Matthew Renner, co-founder and CEO of PassPass, to discuss his latest entrepreneurial venture followi…
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Exclusive offer for Alex & Annie listeners: Get 50% off your onboarding fee when you partner with Extenteam using this link: https://www.extenteam.com/alexandannie Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this First of the Month Special Episode of "Alex & Annie: The Rea…
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In this episode of "Alex & Annie: The Real Women of Vacation Rentals," hosts Alex and Annie are joined by Susan Barry, the president + “queen bee” of Hive Marketing and the podcast host of the “Top Floor” Podcast. Susan shares her journey in the hospitality industry, her experiences with Hive Marketing, and her insights on the evolving landscape of…
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In this episode of How We Grow: The Vacation Rental Show, host Lynell Gordon is joined by Mahwussh Alam, the CEO of One Perfect Stay. Join them as they: Dive into Mahwussh’s journey from starting in the vacation rental space during Airbnb's rise in Dubai to her aspirations of managing thousands of units across the Middle East Uncover the strategies…
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In this episode of "Alex & Annie: The Real Women of Vacation Rentals," hosts Alex & Annie welcome special guest Meaghan Moylan, host of the "Workflows and Espressos" podcast and Executive Director of Outpost - a Vacation Rental and Property Management company located in the Jackson Hole, Wyoming. Meaghan shares her inspiring journey of embracing ne…
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In this episode of The Vacation Rental Show: How We Grow, host Lynell Gordon is joined by Vickie Storm of iTrip. Together, they cover: Why to consider using a franchise model Key benchmarks when scaling a franchise Advice for switching to a franchise model How franchising often exceeds expectations Since 2016, Vickie has been involved with iTrip, i…
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In this episode of "Alex & Annie: The Real Women of Vacation Rentals," hosts Alex & Annie explore the delicate balance between leveraging technology and preserving the irreplaceable human touch in guest communication for the hospitality industry with special guest Nicolas Wegener. Nicolas brings invaluable insights as the visionary leader behind Se…
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In this episode of How We Grow, host and vacation rental industry veteran Lynell Gordon is joined by Eric Goldreyer of bnbfinder. Together, they cover: Why property managers are driving direct reservations Eric’s advice for vacation rental managers: have a website How travelers are actively searching for the option to book direct Eric is CEO of bnb…
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In this episode of The Vacation Rental Show: How We Grow, host Lynell Gordon is joined by Adam Knight of Recreation Vacation Rentals. Together, they cover: The four ‘C’s of hospitality What makes good communication with owners How to grow when you can’t afford to hire new team members How negative experiences can improve your approach to hospitalit…
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In this insightful episode, Alex & Annie are joined by Elisabeth Yoho, Chief People Officer at Harris Vacation Rentals. Elisabeth dives into the critical role of corporate culture in retaining top talent and creating cohesive teams that thrive. She shares valuable strategies for understanding individual team members, leveraging events to build conn…
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In this episode of "Alex & Annie: The Real Women of Vacation Rentals” podcast, hosts Alex and Annie are joined by Pete DiMaio, COO of Travel Boom Marketing. Together, they dive into the latest trends and strategies shaping the hospitality industry, leveraging insights from Travel Boom's recent hotelier sentiment study. Aligning with Guest Preferenc…
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In this episode of The Vacation Rental Show: How We Grow, host Lynell Gordon is joined by Tim Woodward of Local Social. Together, they cover: Strategies for leveraging vacation rental analytics How to maximize property revenue in each quarter Demand and price sensitivity in revenue management Rental management differences in East versus West Tim se…
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In this episode of "Alex & Annie: The Real Women of Vacation Rentals," hosts Alex & Annie dive into the world of short-term rentals (STRs) with Nate Klatt and Dan Mitchen, the innovative minds behind HomeHop. Together, they explore the journey of HomeHop from house flipping to scaling a successful business in the Midwest's STR market. Guests Introd…
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Join Alex & Annie as they delve into the dynamic world of vacation rentals with Erin Booth, COO of Summit Mountain Rentals in Colorado. Erin's extensive background in the industry, from managing a single unit in Brooklyn Heights to her current leadership role, provides a wealth of knowledge and insights for listeners. Erin's Background: Erin Booth'…
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In this episode of How We Grow, host Lynell Gordon is joined by Lisa Stinnett of Inhabit. Together, they cover: ● Inhabit’s history from start-up to industry leader ● How Inhabit is bringing products from residential properties to vacation rentals ● How Inhabit is solving property manager pain points Lisa is CEO of Inhabit, a leader in both the vac…
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In this episode of How We Grow: The Vacation Rental Show, host Lynell Gordon is joined by Jim Bizily of I Love Vacations. Together, they cover: Why a solid team and inventory are key to successful growth How to refine hiring to ensure the right people are in the right seats Why it’s crucial to define your mission and goals early Jim Bizily is Found…
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In this episode of "Alex & Annie: the Real Women of Vacation Rentals," hosts Alex and Annie dive into the world of vacation and RV rental software with special guest Wes Smithe, the co-founder, CEO, and chairman of Direct Software. Join them as they explore Direct's evolution, innovations in direct booking, and Wes' entrepreneurial journey. Direct …
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In this episode of How We Grow: The Vacation Rental Show, host Lynell Gordon is joined by Lino Maldonado of BeHome 247 at the Streamline Conference 2023. Together, they cover: How to use technology wisely Why you should be aware of Hilton Hotel Group’s partnership with Tesla Why now is the time to introduce electric vehicle (EV) charging into your …
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In this episode, Alex & Annie welcome Rich Sippos, Head of Sales at Extenteam, to discuss how their dedicated remote staffing solutions can streamline vacation rental business. Rich shares valuable insights into Extenteam's philosophy, dispels common misconceptions, and reveals how they can support vacation rental businesses. Rich brings a wealth o…
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Welcome to our 1st of the month bonus episode. In this episode, Alex & Annie are not fooling around with April Fools' jokes; instead, they have significant announcements to share! Annie's New Role at NextPax Annie unveils her new role as the Director of Technical Supply for the Americas at NextPax. She discusses her responsibilities, the potential …
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In this episode, we welcome Lynell Gordon – vacation rental expert, partner at Inhabit, and host of "How We Grow: the vacation rental show." Lynell shares her powerful personal journey and how the practice of writing down goals and intentions has positively shaped both her life and career. Meet Lynell: Lynell's vacation rental expertise shines thro…
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In this episode of How We Grow: The Vacation Rental Show, host Lynell Gordon is joined by Rachele Hobbs of Hobbs Realty at the Streamline Conference 2023. Together, they cover: How to achieve high guest loyalty Why you need to know your business goals to grow Hobbs Realty’s unique care offering: Hobbspitality Rachele is CEO of Hobbs Realty, a famil…
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Join Lynell Gordon as she sits down with Tiffany Edwards of Coletta Consulting LLC to ask Governor DeSantis to veto Senate Bill 280. This bill should be vetoed because it: Will harm Florida tourism and property rights Lacks consumer protection measures Makes it harder for families to find accommodation due to its maximum occupancy rules Allows a ta…
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Welcome to "Alex & Annie: The Real Women of Vacation Rentals"! In this insightful episode, we sit down with powerhouse celebrity entrepreneur and personal development leader, David Meltzer. David reveals his profound journey and practical strategies for finding clarity, purpose, and unlimited potential. Learn the power of meditation to elevate your…
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In this episode of How We Grow: The Vacation Rental Show, host Lynell Gordon is joined by industry veteran Scott Leggat. Together, they cover: The current regulatory landscape facing short-term rentals The need for local alliances and trade organizations Why you can’t act like your business is safe from regulatory changes Scott is the Director of G…
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Get the inside scoop on the latest vacation rental technology trends! Alex & Annie are joined by DARM Battleground Baddies: Travis Wilburn, CJ Stam, and Julie Byrd to break down the groundbreaking innovations from this year's Battleground of Technology Providers. Learn why Key Data's data-driven tools were the clear winner and how AI is changing ho…
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