Entrepreneurship Episodes

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 Olin, President of C2G Advisors. Jason has over 20 years of experience in vacation rentals, previously running 360 Blue in the Panhandle area. ...

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...

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 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 new opportunities in the dynamic vacation rental industry. The Year of Yes Mentality Meaghan highlights how adopting a "year of yes" mindset opened d...

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” podcast, hosts Alex and Annie are joined by Pete DiMaio, CEO 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 Preferences Drawing from Travel Boom's recent hotelier sentiment study, they unpack the misalignment between guest preferences and hotelier perceptions, emp...

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, 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 through her work with Inhabit and her podcast, "How We Grow: the vacation rental show." Her dedication to sharing industry knowledge and personal exper...

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 mindset, plus the value of a "be interested, not interesting" approach that will reshape how you live and lead. Key Takeaways: 🧘‍♀️ The Powe...

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 how properties are booked. Darm Conference Highlights Discover the standout technologies showcased at the DARM Conference and get the judges' expert ...

In this episode of "Alex & Annie, The Real Women of Vacation Rentals," hosts Alex & Annie welcome back and dive deep into the extraordinary journey of Jen Ford, a trailblazer in the vacation rental industry. Join us as we uncover the highs, lows, and unexpected turns that shaped her remarkable career. Jen's Evolution in the Vacation Rental Industry: Jen shares her transition from the fast-paced world of high tech to becoming a finance executive at HomeAway, and her decision to take some time ...

Join Alex and Annie in this insightful episode of "Alex and Annie, The Real Women of Vacation Rentals," recorded live from Panama City Beach, as they welcome Michael, a seasoned vacation rental expert, to discuss his journey in the industry. From starting a business with a solid plan to exiting and now embarking on a new venture with a focus on accessibility, Michael shares his wealth of knowledge and experience. Michael's Journey: Michael recounts his move to the 30A area in 2004 and the lau...