Alex and Annie: The Real Women of Vacation Rentals Alex and Annie

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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. He has worn many hats from development to property management before spinning off software companies like Keydata.

Jacobie has been immersed in the industry since childhood, born into a vacation rental family in the Florida Panhandle. After a stint away, he returned in 2017 and now leads C2G Advisors, providing strategic consulting and M&A advising.

With their decades of combined experience, Jason and Jacobie provide valuable insights on:

📈 How the industry has shifted from the post-COVID peak, and what this "normalization" means for acquisitions

💰 Key metrics buyers evaluate when valuing a business, including growth rate, staffing margins, churn rate, and more

🏡 The concept of building an "Airbnb empire" vs a sustainable, transferable business

🏨 The emergence of "house of brands" models as companies acquire strong regional players

🤝 How long owners should prepare before pursuing a sale (hint: start tracking metrics 3 years out if possible)

🗺️ Why national branding remains an elusive goal, and regional dominance is key

Whether you're an owner considering an exit, or just want to build a stronger business, Jason and Jacobie share priceless wisdom every vacation rental pro needs to hear. Tune in for their expert perspectives on setting up your company for long-term success!

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Connect with Jason Sprenkle

LinkedIn

Connect with Jacobie Olin

LinkedIn

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 discussion explores the challenges of scaling a vacation rental business while maintaining high-quality service. Marcus examines why most companies will likely remain small and owner-operated despite industry narratives.

Crafting Enriching Industry Events

Marcus provides a critique of the lack of tactical, actionable content at many industry conferences. He reveals plans for Hostaway's first user conference "Hostchella" aimed at fostering practical education.

Empowering Choice in Technology

Marcus emphasizes Hostaway's philosophy of giving users the freedom to choose the tools that work best for their business needs, rather than forcing an all-in-one suite. Hear his thoughts on striking a balance between integrated and open ecosystems.

Key Takeaways: 

🤝 Collaboration over Domination: Learn why Hostaway prioritizes being a humble partner rather than having an "ownership mentality" that hurts industry collaboration. 

💰 Unlocking Growth Opportunities: Uncover strategies for responsibly scaling your business while maintaining operational excellence. 

🎓 Cultivating Practical Education: Gain perspectives on crafting enriching educational experiences tailored to the diverse needs of vacation rental professionals. 

Join Alex & Annie for this insightful conversation with Marcus Rader as he shares his vision for shaping the future of the vacation rental industry.

Send a voice message to Alex & Annie: https://podcasters.spotify.com/pod/show/alexandanniepodcast0/message

Your message could end up on a future episode of this podcast!

Connect with Marcus Rader

LinkedIn

Connect with Hostaway

LinkedIn | Website

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 corporate world after 16 years to start his own company, PassPass. He shares the excitement and challenges of embracing the entrepreneurial mindset.

The PassPass Business Model Explained

Matt dives into the unique PassPass business model that aims to create a win-win for businesses and consumers. Businesses provide deals for free, while consumers pay a $5 monthly fee for access to discounts nationwide. Participating businesses then earn a revenue share from referred customers.

Empowering Small Businesses to Compete

A core mission of PassPass is leveling the playing field to help independent small businesses thrive against major corporate brands. Matt discusses how the revenue sharing model and subscription discounts enable small businesses to effectively compete.

Key Takeaways:

🔄 Career Pivots: Insights into making bold career transitions from corporate leadership to entrepreneurship.

⚖️ Aligning Incentives: Exploring PassPass' innovative model that aligns business and consumer incentives through revenue sharing and valuable discounts.

📈 Uplifting Small Business: Learn how PassPass aims to empower independent businesses to gain a competitive edge against big brands.

Tune in for an inspiring discussion about Matt's entrepreneurial journey, the PassPass concept, and its potential to shake up the deals/discounts landscape for the greater benefit of businesses and consumers alike.

Send a voice message to Alex & Annie: https://podcasters.spotify.com/pod/show/alexandanniepodcast0/message

Your message could end up on a future episode of this podcast!

Connect with Matt:

LinkedIn

Connect with PassPass:

LinkedIn | Website

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 rental company in the Lake Norman area of North Carolina.

From Unique Beginnings to Vacation Rental Success 

Caleb shares his unconventional path to the industry, working in marketing, teaching, and non-profit management before joining Stay Lake Norman as an Operations Coordinator during COVID. Despite having no prior hospitality experience, Caleb immersed himself in the industry through podcasts and immediately fell in love with the problem-solving nature of vacation rental operations. His dedication and passion propelled him to rise through the ranks, becoming COO and even purchasing a portion of the company.

Crafting Exceptional Guest Experiences 

Stay Lake Norman takes a meticulous approach to curating unforgettable guest experiences. Caleb discusses their robust tech stack, including Streamline, Breezeway, Turno, SiliconTravel, and PointCentral, emphasizing the importance of best-in-class solutions.

Standing Out with Targeted Marketing Strategies 

Caleb highlights Stay Lake Norman's impressive 73.5% direct booking ratio, crediting a strong focus on SEO, content creation, a dedicated podcast, and positioning themselves as the go-to resource for all things Lake Norman.

Key Takeaways: 

🏡 Operational Excellence: Discover the systems and processes Stay Lake Norman implements to ensure top-notch service and streamlined operations. 

📈 Effective Marketing Tactics: Learn valuable strategies for driving direct bookings, leveraging content marketing, and establishing a strong local presence. 

🛶 Curating Memorable Experiences: Gain insights into creating exceptional guest experiences by offering unique ancillary services and fostering community connections.

Join Alex and Annie as they delve into Caleb's journey, gleaning valuable lessons on operations, marketing, and guest-centric approaches that have propelled Stay Lake Norman's success.

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 became the queen bee of Hive Marketing. She discusses her early career in Tallahassee, Florida, working in the restaurant and catering industry, and her move to Denver, Colorado, which marked the beginning of her career in hotel management and marketing.

The Intersection of Hotels and Vacation Rentals:

The trio explore the relationship between hotels and vacation rentals, addressing the perception of competition and the potential for collaboration. They discuss the importance of offering a spectrum of lodging types and the need for hotels to recognize the impact of vacation rentals on the market.

Challenges and Opportunities in Hospitality:

The trio discuss the challenges faced by women in the hospitality industry, particularly in breaking through the "good old boy" network. Susan emphasizes the importance of recognizing systemic issues and the need for organizational support for women and people of color in hospitality.

Key Takeaways:

🌟 The Evolution of Hive Marketing: Susan's journey from catering to founding Hive Marketing and its growth over the years.

🔑 Challenges for Women in Hospitality: The systemic issues faced by women and the importance of organizational support.

🤖 The Impact of Technology and AI: Susan shares her thoughts on the role of technology and AI in hospitality, particularly in revenue management.

Connect with Susan Barry:

LinkedIn | The Top Floor Podcast

Connect with Hive Marketing:

Website

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 doors to invaluable experiences and connections. By saying "yes" to speaking engagements, industry events, and even hosting a podcast, she expanded her network and gained valuable insights.

Navigating Unique Market Challenges

Working with Outpost in Jackson, Wyoming, Meaghan offers a unique perspective on navigating regulatory hurdles near national parks and protected lands. She discusses strategies for educating guests, fostering community relationships, and promoting sustainable tourism practices.

Leveraging Technology and Innovation

The discussion explores the rapid technological advancements in the vacation rental industry. Meaghan shares her experiences with implementing new tech stacks, property management systems, and keyless entry solutions to enhance operational efficiency and guest experiences.

Key Takeaways:

👥 Building Meaningful Connections: Discover how cultivating an open mindset and actively networking can foster impactful relationships and collaborations within the industry.

🌳 Responsible Tourism Practices: Learn strategies for prioritizing environmental sustainability, community engagement, and regulatory compliance in unique vacation rental markets.

💡 Continuous Innovation: Gain insights into staying ahead of the curve by continuously adopting new technologies and operational tools to drive efficiency and enhance guest satisfaction.

Join Alex and Annie as they dive into Meaghan’s inspiring journey and glean valuable lessons for growth and success in the vacation rental space.

Connect with Meaghan:

LinkedIn

Workflows & Espressos Podcast

Connect with Outpost:

LinkedIn

Website