Software Episodes

In this week’s episode, Alex & 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...

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 o...

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 sh...

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 success...

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 ...

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 mark...

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In this exciting episode, Alex and 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 dri...

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 giv...

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, from living exclusively in Airbnbs during the pandemic to founding a company that's revolutionizing how travelers find and book vacation rentals. ...

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. With over two decades of experience, Simon has been at the forefront of innovation and strategy, guiding countless property management companies throu...

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 previous ventures and how they led to the creation and success of BnBFinder. He also talks about the challenges and opportunities within the ind...

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 into the growing pains of regulation across different markets and the underlying psychology behind it. The Quest for Quality at Scale The discus...

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 following an extensive career in the corporate world. Transitioning from Corporate to Startup Life Matt opens up about his motivations for leaving the c...

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 Real Women of Vacation Rentals," hosts Alex & Annie welcome special guest Caleb Hannon, COO of Stay Lake Norman - a professional luxury vacation renta...

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 hospitality marketing and management. Susan's Background and Journey: Susan Barry, originally from Panama City, shares her background and how she ...

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 Sendsquared, a pioneering communication platform tailored for the vacation rental industry. With a deep understanding of fostering meaningful connect...

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 Introduction: Nate Klatt, a seasoned CPA specializing in real estate investments, brings strategic financial acumen to HomeHop. Dan Mitchen, with a backg...

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 Software's Impact: Wes Smithe introduces Direct Software, a vertical SaaS platform revolutionizing asset management, booking, and back-office opera...

In this episode of "Alex and Annie, The Real Women of Vacation Rentals," we embark on a fascinating journey into the vacation rental industry with a panel of seasoned experts known as the OGs of the Panhandle. Our guests, including trailblazers like Jim Olin, Steve Caron, Lino Maldonado, and Paul Wolford, share their personal journeys from the industry's early days to the dynamic landscape it occupies today. The Early Days: Dive into the challenges and triumphs of being pioneers in the vacati...

Join Alex & Annie with a cute participation of Chloe, newest furry member of the family, as they delve into the current vacation rental market trends. They share their insights on the fluctuating booking rates and the explosion of Airbnb listings, particularly in the Myrtle Beach area. The duo discusses the critical need for property managers to diversify their booking strategies and the importance of direct bookings as a way to build resilience in an increasingly competitive market. Key Take...

In this episode, Alex had the opportunity to sit down with Jonathan Ruggles, the Director of Partnerships at Flip.to. They discuss three key points in hospitality marketing: building your digital presence on your own land, leveraging guest-generated content and audiences, and the power of being a first mover in adopting innovative strategies. Alex shares insights from her experience in the vacation rental industry, emphasizing the importance of owning data, creating authentic interactions, and s...

Join Alex, Annie, and special guest Margot Schmorak in this episode of "Alex & Annie, the real women of Vacation Rentals," as they explore the captivating journey of Hostfully over the past year and the crucial aspects of building a supportive community for women in the vacation rental industry. Listen as Margot shares her experiences in a powerful group, emphasizing the importance of mutual support, advice-sharing, and mentorship for women navigating both personal and professional challenges. ...

In this episode of "Alex & Annie: The Real Women of Vacation Rentals," we sit down with Vered Schwarz, the President and COO of Guesty, to not only delve into Guesty's new offerings but also shine a spotlight on the vital role of women supporting women in the vacation rental industry. AI in the Vacation Rental Industry: The implementation of AI goes beyond messaging for Guesty. We delve into how Guesty envisions AI playing a role in marketing and revenue management, personalizing communicatio...