Alex and Annie: The Real Women of Vacation Rentals

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

💡 The Role of Brand and Humor in CanMonkey’s Marketing

🤝 Navigating Regulations in Vacation Rentals

📌 The Gig Economy Workforce

💬 Expanding Services Beyond Trash Curb Management

🎯 Looking Ahead to 2025

⭐ Advice for Entrepreneurs

Connect with Alex:

LinkedIn: https://www.linkedin.com/in/k-alexander-shapiro-74b47259/

Connect with CanMonkey:

LinkedIn: https://www.linkedin.com/company/canmonkeyinc/

Instagram: https://www.instagram.com/canmonkeyinc/

Facebook: https://www.facebook.com/CanMonkey

YouTube: https://www.youtube.com/channel/UCha6rByeYqvhNrTbA5fwUPg 

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.

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#VacationRentalTech

#PropertyManagementInnovation

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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:

🥚 The Origins of Industry Podcasts✨ Reflections on 200 Episodes🎙 The Power of Podcasting⭐ Trends in the Vacation Rental Industry💻 Technology Transforming the Industry🎧 Memorable Moments from Podcasting💬 Lessons for Aspiring Podcasters📌 The Future of the Industry and Podcasting

Connect with Sarah and T:

Sarah Bradford: https://www.linkedin.com/in/sarah-bradford-032129b1/

Tim Cafferty: https://www.linkedin.com/in/tim-cafferty-479b974/

Connect with Travis Wilburn

LinkedIn: https://www.linkedin.com/in/travis-wilburn-03057410/

Connect with Wil Slickers

LinkedIn: https://www.linkedin.com/in/wil-slickers/

Connect with Tom Goodwin

LinkedIn: https://www.linkedin.com/in/trgoodwinmlc/

Connect with Amber Hurdle

LinkedIn: https://www.linkedin.com/in/theamberhurdle/

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.

#AlexAndAnnieat200 #vacationrentals #podcasting

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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:

🍃 Managing Hurricane Recovery and Restoring Guest Confidence

💡 The Rise of All-In-One Solutions in Vacation Rental Tech

⚡ CRMs as the Backbone of Modern Property Management

🤖 AI and Automation’s Impact on Vacation Rentals

🧮 Trust Accounting and Its Growing Industry Importance

💻 Content Marketing Strategies for Direct Booking Success

🚪 The Growing Competition from All-Inclusive Resorts

🔮 Short- and Long-Term Predictions for Vacation Rentals

Connect with Terry:

LinkedIn: https://www.linkedin.com/in/terry-whyte-4540633b/

Website: https://annamariaislandbeachrentals.com/

Want to optimize your guest experience? Exclusive for our listeners: Get a free guest journey analysis at https://www.happyguestofficial.com/

#vacationrentals #propertymanagement #vacationrentaltech

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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:

💭 Reflections on 2024

🎧 Top 5 Podcast Episodes 2024

✨ Alex & Annie’s Words of the Year 2025

⭐ Insights on Industry Trends

🔮 Future Podcast Plans

🤝 Gratitude and Mentorship

📍 Conference Plans for 2025

#vacationrentals #newyear2025 #goalsetting

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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:

💭 The Vision for For the Love of Gatlinburg

✨ Mountain Laurel Chalets: A Family Legacy

🎯 Challenges and Insights from Acquiring Another Company

⭐ The Importance of Guest Experiences

⚡ Marketing and Branding Strategies

🤝 Community and Industry Collaboration

💡 The Role of Hospitality in Fostering Connection

📍 Future Goals and Inspirations

Connect with Tom Goodwin:

LinkedIn: https://www.linkedin.com/in/trgoodwinmlc/

Website: https://www.mtnlaurelchalets.com/

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!

#VacationRentals #ShortTermRentals #Gatlinburg

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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:

🔨 Building Personal and Employer Brands

🗺 Navigating Career Transitions

🔥 Confidence and Personal Power

🧹 Cleaning Out Your “Friend Closet”

🤝 The Role of Authenticity

⭐ Leadership and Empowerment

💡 Reflections and Lessons Learned

Connect with Amber:

Website: https://www.employerbrandcentral.com/

LinkedIn: https://www.linkedin.com/in/theamberhurdle/

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!

#PersonalBranding #EmployerBranding #CareerTransitions

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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:

🐣 The evolution and impact of Airbnb’s Co-Host Experience.

✨ Why diversifying your booking channels is critical for long-term success.

🍃 The critical role of advocacy in addressing regulatory challenges.

🙌 Building statewide coalitions to create sustainable solutions for hosts and communities.

📢 How small-scale operators can find their voice and make an impact.

🤝 John’s collaboration with Rent Responsibly to educate and empower hosts.

⭐ Bridging gaps between operators and local governments through open dialogue.

🔔 The importance of noise monitoring, safety measures, and compliance for professionalizing the industry.

Connect with John

LinkedIn: https://www.linkedin.com/in/johnhildebrandphoto/

Website: https://hildehomes.com/

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!

#vacationrentals #STRregulations #vacationrentaladvocacy

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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

📢 Using realtor referrals to grow a portfolio

🎯 Choosing and evolving a tech stack

🙌 Building and managing a strong team

💡 Benefits of community involvement with the Chamber of Commerce

📊 Plans for scaling to 250 properties

🎧 Insights from Declan’s podcast, STR Unlocked

Connect with Declan:

LinkedIn: ⁠https://www.linkedin.com/in/declan-mcgonigal/⁠

Website: ⁠https://mybeachrentals.com/⁠

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!

#VacationRentals

#PropertyManagement

#BusinessGrowth

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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:

🎯 The Vision for DARM 2024

⭐ Revolutionizing Revenue and Marketing Strategies

⚡ Tech Innovation and Challenges

📊 Industry Insights and Trends

💡 DARM’s Signature Battleground Competition

🤝 Building Connections and Community

Connect with Amy:

LinkedIn: https://www.linkedin.com/in/amymutual/

DARM Website: https://vrdarm.com/registration/

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!

#DARM #DARM2024 #VacationRentals

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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:

🚪 Steve’s Background in Luxury Hotels

🐣 Founding Tangy Management

🎙 Launching The Hospitality Mentor Podcast

✨ Event Organizing and Community Building

⚡ Innovative Approaches to Guest Experience

💡 Expansion Plans & Market Challenges

Whether you're a seasoned property manager or just curious about the evolving landscape of vacation rentals, Steve's insights into the business and his innovative projects are sure to inspire.

Connect with Steve:

LinkedIn

Website

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!

#LuxuryVacationRentals #HospitalityStandards #BotiqueBrand

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