Bill Faeth has built a career around identifying opportunities before the rest of the market catches on. After decades investing in residential and commercial real estate, he transitioned much of his portfolio into short-term rentals in 2015, building a multi-million-dollar business across highly desirable vacation markets. Today, through Build STR Wealth, he coaches investors and operators on everything from portfolio growth and self-management to building long-term wealth through vacation rentals.


In this first part of a three-part conversation, however, the focus shifts away from investing and toward the evolution of the vacation rental industry itself.


Lynell sits down with Bill to explore one of the industry's biggest points of tension: the perceived divide between traditional property managers and the rapidly growing co-host community. Bill shares why he believes both groups bring valuable perspectives, where misunderstandings have emerged, and why collaboration will ultimately strengthen the industry more than competition ever could. The conversation also explores ethical co-hosting practices, merchant-of-record responsibilities, mentorship, community building, and Bill's vision for creating more meaningful industry events.


What you'll learn:

• Why Bill believes professional property managers and co-hosts have more to learn from each other than compete over
• How co-hosting differs from traditional property management and where responsibilities should begin and end
• Why merchant-of-record responsibilities matter and how co-hosts can structure their businesses to better protect homeowners
• How mentorship and community have shaped Bill's career and why they're central to his vision for the industry's future
• Why Bill and Steve Schwab are creating a new conference centered on small-group learning, collaboration, and relationship building
• How content creators, educators, coaches, and operators each play different roles within the vacation rental ecosystem
• Why helping the industry grow has become more important to Bill than simply growing his own business
  
  

About Bill Faeth: Bill Faeth is the founder of Build STR Wealth and a veteran real estate investor with nearly three decades of experience across residential, commercial, and short-term rentals. After transitioning much of his portfolio into vacation rentals in 2015, he built a multi-million-dollar portfolio while helping thousands of investors improve profitability through smarter ownership and self-management. Today, Bill is a respected educator, speaker, and mentor who is passionate about strengthening the vacation rental industry through collaboration, ethical business practices, and community. 

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Book Time with Lynell at Streamline Summit: https://calendly.com/lynellgordon/the-vacation-rental-show-podcast-ss 

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show


The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Agentic AI is one of the most talked about, least understood terms in vacation rental technology right now, and Resha Shroff wants operators to slow down before they buy in. As CEO and founder of Lynx, a hospitality automation company that has scaled from a startup into a global platform, Resha has spent her career on every side of the property management equation: operator, guest, and now technology builder.


What you'll learn:

• Why buying software just because it's labeled "agentic AI" is the fastest way to waste a year of AI strategy
• What agentic AI actually means, and why one AI agent can't do the job of an entire team
• How to evaluate whether your AI vendor has actually trained its AI for hospitality, or just handed you a generic chatbot
• Why every AI deployment needs a job description and Key Result Areas (KRAs), the same way a new hire would
• How Resha built her own AI executive assistant in Claude, and what it does for her every single day
• Why starting your AI journey internally, before it touches guests, is the safer, smarter first move
  
  

Resha has been investing in and operating short term and midterm rental properties for more than fifteen years, and she now co-invests in boutique hotels alongside some of her own customers. That dual perspective, operator and vendor, shapes everything she builds at Lynx, where the focus is on centralizing fragmented data sources so AI actually has enough context to be useful. 

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show
The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Operations teams rarely get the spotlight, but they're the ones who make or break a guest's vacation. In this episode of The Vacation Rental Show, Lynell Gordon talks with Dave Roberts, VP of Operations and Strategy at Outer Banks Blue Realty Services, about why field staff are the true face of a property management company and how lean, data driven systems keep a 300 property portfolio running smoothly, even during the busiest turnover days of the year.


What you'll learn:

• Why field staff, not the office team, are the true face of a vacation rental company
• Where AI and automation genuinely help operations, and where the human element still leads
• How a Kaizen blitz took same day resolution from 63 percent to a sustained 100 percent
• Why a balanced scorecard across guest, owner, and employee metrics keeps every department accountable
• Why micromanagement fails in high volume operations and what to build instead
• How to solve real owner communication gaps, from HVAC accountability to handwritten thank you notes
  
  

About Dave Roberts: Dave Roberts is VP of Operations and Strategy at Outer Banks Blue Realty Services and Principal Owner of VRM Excellence. He brings more than thirty years of operational leadership experience across multiple industries, over a decade of it in vacation rentals, along with a Six Sigma certification and a lean management background that shapes how he approaches property management operations. 


This episode is sponsored by Streamline Summit 2026

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show
The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Annie Holcombe has been part of the vacation rental industry since 1992, building a career that spans property management, owner relations, OTA strategy, business development, hospitality technology, and industry leadership. Today, as Founder and Chief STRategist at Annie & Co. Solutions, she helps property managers strengthen owner relationships, improve business development, and build long-term growth strategies, while also serving as Brand Ambassador for Booking.com and co-hosting Alex & Annie: The Real Women of Vacation Rentals. Throughout her career, Annie has become one of the industry's most connected voices, known for bringing people together and helping businesses grow through meaningful relationships.


In this episode, Lynell sits down with Annie to reflect on how the vacation rental industry has changed, where it's heading next, and why relationships, not technology alone, will continue to determine who succeeds.


What you'll learn:

• Why the post-COVID boom created a knowledge gap between experienced vacation rental operators and newer short-term rental hosts
• Why owner retention may become a bigger competitive advantage than owner acquisition over the next few years
• How consistent, personal communication helps property managers build stronger, longer-lasting owner relationships
• Why diversification across multiple booking channels remains essential instead of relying too heavily on any single platform
• What smaller property managers should prioritize when choosing technology and building their operational foundation
• Why finding mentors and becoming active within the vacation rental community can accelerate growth far more than trying to figure everything out alone
• How Annie is helping Booking.com better understand the needs of property managers and bridge long-standing gaps between the platform and the vacation rental industry
  
  

About Annie Holcombe: Annie Holcombe is the Founder and Chief STRategist at Annie & Co. Solutions, Brand Ambassador for Booking.com, and co-host of Alex & Annie: The Real Women of Vacation Rentals. Since entering the industry in 1992, she has worked across property management, distribution strategy, hospitality technology, and business development, helping operators, suppliers, and technology companies grow through stronger relationships and smarter strategy. Annie also serves on the VRMA Board of Directors and is widely recognized as one of the vacation rental industry's most trusted and well-connected leaders. 

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show


The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Alex Zemianek has built his career around creating businesses that solve real operational problems. As CEO of JZ Vacation Rentals, he has spent years growing a vacation rental company while investing in real estate and developing systems that improve efficiency. Despite having no coding or technical background, Alex became fascinated with AI after attending an industry roundtable, leading him to rebuild much of his company's operations around custom AI agents and intelligent workflows. Today, he also serves as an advisor to several hospitality technology companies, helping shape how AI is being adopted across the vacation rental industry.


In this episode, Lynell sits down with Alex to discuss why AI is becoming much more than another productivity tool and how operators can begin using it to simplify operations without sacrificing hospitality.


What you'll learn:

• Why you don't need a technical background to build practical AI workflows for your vacation rental business
• The difference between using AI chat tools and creating custom AI agents that work autonomously
• How Alex uses AI for financial reporting, bookkeeping, marketing, meeting summaries, and project management
• Why connecting your existing software through APIs and AI workflows can replace constantly switching between dozens of platforms
• How to identify repetitive tasks that AI can handle while keeping humans focused on guest relationships
• Why the future of vacation rental operations will revolve around a single AI-powered "cockpit" instead of disconnected software tools
• How AI can help operators improve efficiency while doubling down on personalized guest experiences
  
  

About Alex Zemianek: Alex Zemianek is the CEO of JZ Vacation Rentals, a full-time real estate investor, developer, public speaker, and vacation rental entrepreneur based in St. Louis, Missouri. He advises several hospitality technology companies on AI adoption and automation, while building custom AI systems inside his own business to streamline operations, improve decision-making, and create better guest experiences. Alex believes success comes from being the most resourceful person in the room, surrounding yourself with people who know more than you do, and using technology to give teams more time to focus on what matters most. 

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show


The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Cassondra Liles has spent 25 years in real estate brokerage helping clients build wealth through smart, strategic property decisions. As the broker of The Key Team in North Carolina and the author of Real Life Monopoly, she combines deep local market knowledge with hands-on short-term rental (STR) experience, self-managing a portfolio of eight properties from the mountains to the coast. What started as an accidental first purchase near East Carolina University (ECU) became the foundation of a real estate investment strategy she now shares with clients, agents, and aspiring investors across the state.


In this episode, Lynell sits down with Cassondra to discuss what it really takes to build a profitable vacation rental income portfolio in today's market, and why so many well-intentioned investors get it wrong.


What you'll learn:

• Why emotion-driven investing fails and which investment property numbers to analyze before you commit to any property
• How to evaluate market saturation and determine whether a location has room for another short-term rental
• The true cost picture behind any vacation rental, from mortgage and cleaning fees to heating, ventilation, and air conditioning (HVAC) replacements and hidden ancillary expenses
• Why the hybrid rental model works as both a personal second home and a vacation rental income asset
• How the 1.25 rule applies to short-term rental investing and what it means for actual cash flow
• Why home equity is one of the most underused tools for building a real estate investment strategy
  
  

About Cassondra Liles: Cassondra Liles is an award-winning real estate broker, investor, and author with more than 25 years of experience in the industry. She is the broker of The Key Team, serving Wake and Johnston counties in North Carolina, and the author of Real Life Monopoly, available on Amazon. She self-manages a portfolio of eight short-term rental properties across multiple markets.


This episode is sponsored by Streamline Summit.

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show
The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

2025 produced a year of real conversations on The Vacation Rental Show, and in this special compilation, host Lynell Gordon goes back through her notes. She revisits sixteen of the year's most listened-to episodes and the advice that made listeners pull over and write something down, organized around four themes that shaped the year in short-term rental.


What you'll learn:

• Why standardizing your systems matters before you scale your inventory
• How leading with guest experience lets revenue follow naturally
• What luxury and personalization actually look like in practice
• Why guest safety, advocacy, and payment risk can't wait until something goes wrong
• How disaster preparedness starts with protecting your own team
• Why authentic relationships remain the long game in property management
  
  

This compilation features advice from founders, operators, advocates, and technologists across the industry, including Jonathan Fonvielle, Angie Leone, Sue Jones, Eric Moeller, Rachel Alday, Milad Ghods, Kory Rankine, Grace Souter, Justin Ford, Scott Leggat, the team behind Hospitality Heroes, Matthew Gurley, Annie Holcombe, Mike Norde, Anne Gardner, Sofia Rossato, and Derreck Kayongo. Together they cover scaling, guest experience, safety, regulation, payment processing, leadership, and purpose.


The through-line is simple: build the right systems, put the guest first, protect what you've worked for, and stay in the community, because at its very best this industry doesn't compete, it collaborates. Subscribe to The Vacation Rental Show wherever you listen, leave a rating and a review, and share this with someone who needs to hear it. New conversations every Tuesday.

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Kimberly Layton spent decades in corporate America working with Fortune 500 organizations in healthcare, finance, and retail, helping executive teams cut through noise and align their strategy with results. After leaving Dell Technologies, she applied that same discipline to a new challenge: vacation rental property management. As the owner of SkyRun Naples, Kimberly is building a short-term rental business grounded in honest homeowner communication, genuine accountability, and a willingness to have the hard conversations that many property managers avoid.


What you'll learn:

• Why setting false revenue expectations during onboarding is one of the most costly mistakes in vacation rental management
• How Kimberly's corporate background shapes her approach to every owner relationship and team-building decision
• The growing battle between property managers and Online Travel Agencies (OTAs) over guest data and who really owns the guest relationship
• How to build and maintain lasting owner trust, especially when something goes wrong
• Why the franchise model gave Kimberly the operational support to focus on what matters most: acquiring owners and serving guests
• How artificial intelligence (AI) tools and a structured monthly review practice are helping her scale more efficiently
  
  

About Kimberly Layton:
 Kimberly Layton is the owner of SkyRun Naples, a franchise location of SkyRun Vacation Rentals. Before entering the vacation rental industry, she spent decades in enterprise technology and strategic business development, most recently at Dell Technologies. She brings the same communication discipline, value-driven sales approach, and results-focused mindset from her corporate career into her day-to-day work as a property manager, business owner, and franchise operator.


This episode is sponsored by iTrip

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show


The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Rebecca Lombardo started her career as a backpack journalist, reporting from Namibia, Japan, and Ukraine before going on to shape brand narratives and marketing strategy for Fortune 500 companies including Kraft, Heinz, Revlon, and eBay. Today, through her Rebecca Lombardo Agency, she works as a fractional CMO for vacation rental companies, SaaS brands, and hospitality businesses that need senior-level marketing leadership without the overhead of a full in-house team. She's also an award-winning speaker, writer, moderator, and host of the podcast Vendor Vibes.


In this episode, Rebecca introduces the concept of owning your brand engine: a trained AI project that acts as an operating system for your marketing, constantly improving as you feed it more of your brand's voice, reviews, and strategy. She explains why letting an agency own your AI environment means losing your most valuable marketing asset, and how a properly built brand brain can cut your Google Ads cost per lead, tighten your messaging, and make every agency transition seamless.


What You'll Learn:

• Why brand is what people say about you when you're not in the room, not your logo
• How to build and train an AI brand engine that your company owns
• Why filtering your ad copy through a brand engine can lower your cost of acquisition by $100 per lead
• How AI platforms source answers from editorial articles and media mentions before they look at your website
• What clarity and consistency in messaging mean for homeowner trust
• How to strengthen your brand starting with outside perspective and real audience language
  
  

This episode is brought to you by BlueTent, providing vacation rental pros with direct booking optimization, strategic account management, email marketing, and channel management. Visit BlueTent.com to learn more.


If you're ready to stop competing on price and start building a brand that actually works for you, this episode is your starting point. Search for The Vacation Rental Show on Apple Podcasts, Spotify, or YouTube, and hit subscribe so you never miss an episode.


This episode is sponsored by Bluetent

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
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👉 RSS - https://feeds.fame.so/the-vacation-rental-show


The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →

Amber Erickson-Hurdle is a globally recognized brand and reputation strategist who helps founders and executives turn credibility and visibility into measurable business results. Recently ranked number two in the world for brand thought leadership, she's worked with leaders across industries and influenced billions in profitability. As the founder of BrandEdge Accelerator, Amber brings deep experience in helping operators align who they are with the goals they're chasing.


In this episode of The Vacation Rental Show, host Lynell Gordon and Amber dig into why reputation's the most valuable asset a property manager owns. They cover personal brand strategy, visible leadership, stakeholder trust, and the future of reputation in an AI-driven world.


What you'll learn:

• Why reputation's your currency and how to make it work overtime for you
• The stakeholder framework every property management leader should know
• How the emotional bank account model builds employee trust and culture
• Why empathy and mirroring create deeper homeowner relationships
• What AI's rewarding (and ignoring) when guests and homeowners search
• How to build a personal brand that's authentic and converts
  
  

Amber draws on her background in hospitality, public relations, and brand strategy to give operators practical guidance on building a reputation that compounds. From visible leadership inside your team to stakeholder management in your community, the episode lays out a connected system property managers can put to work right away.


🎧 Listen on Apple Podcasts | Listen on Spotify 📺 Watch on YouTube | Follow The Vacation Rental Show for weekly insights


This episode is sponsored by Streamline

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show


The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

• Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
• Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
• Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty

Got a question for The Vacation Rental Show?Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW 

Tune in to hear your answer featured on The Vacation Rental Show.


Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

• Scaling your vacation rental portfolio
• Optimizing guest experiences
• Revenue management strategies
• Industry trends and market insights

Express your interest in being a guest →