The Vacation Rental Show, Hosted by Lynell Gordon

Dana Lubner believes short-term rental operators need to think about advocacy before a regulatory crisis forces them to. In this episode, she and Lynell Gordon discuss why regulatory risk deserves a place alongside the other risks property managers already manage. Dana shares how her own advocacy journey began after seeing STR hosts arrested in Denver and realizing that operators needed to organize, represent themselves professionally, and build relationships with the people making decisions about their businesses.


For operators who don't have time to become policy experts, Dana recommends finding a level of involvement they can realistically maintain. That could mean assigning someone on the team to community engagement, joining a local or state association, contributing a few hours each month, or supporting advocacy financially. She also explains why operators managing across multiple jurisdictions benefit from associations that already have systems in place to monitor local agendas and regulatory changes.


The larger message is that sustainable advocacy requires infrastructure. Dana explains why volunteer-led organizations can struggle with burnout and why associations need year-round funding and professional support instead of scrambling for resources when a crisis appears. For operators wondering where to begin, she offers three questions: Who's watching? Who's at the table? And how am I supporting them?


What you'll learn:

• Why Dana believes operators should build advocacy infrastructure before a regulatory crisis hits
• How her experience with regulatory uncertainty in Denver shaped her approach to STR advocacy
• How property managers can choose a level of advocacy involvement they can realistically sustain
• Why doing nothing can be one of the biggest mistakes when new STR regulations are proposed
• How local and state associations can help operators monitor regulatory changes across multiple markets
• Why relationships with policymakers should be built before operators urgently need them
• Why volunteer-led advocacy organizations need sustainable funding and professional support
• How operators can contribute through their time, talent, relationships, voice, or financial support
  
  

About Dana Lubner: Dana Lubner is Director of Community Development at Rent Responsibly, where she works with short-term rental operators and local alliances to strengthen their communities and representation. Her career in the vacation rental industry began in property management, which led to her work in STR advocacy and civic engagement. Before becoming Director of Community Development in 2023, Dana served as Rent Responsibly's Head of Advocacy and later Head of Leadership Development. She is also President of Denver's STR alliance, Mile High Hosts, and has experience helping launch and support short-term rental associations. Her work focuses on helping operators organize, develop sustainable advocacy infrastructure, and build relationships within the communities where they operate.

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 →

Scott Leggat believes advocacy should be treated as a standard part of running a vacation rental business, alongside insurance, payroll, and marketing. In this episode, he and Lynell Gordon look at the growing regulatory pressure facing short-term rentals and why operators can't afford to wait until restrictive legislation appears before getting involved. Scott explains how regulations are often copied from one city or town to another before their effectiveness has been tested, and discusses current examples including Alabama's merchant of record legislation, the complex situation in Maui, and the ongoing regulatory debate in Dallas.


Scott also explains how Inhabit is using AI to help operators understand regulatory risk before it becomes a bigger business problem. Its regulatory risk assessment tool can examine a city, ZIP code, state, or region and identify the current regulatory climate, potential changes, and the people involved in proposed legislation. That information is becoming particularly important in mergers and acquisitions, where buyers need to understand the regulatory exposure attached to a vacation rental company or market. 


The larger message is that property managers need to become active participants in the conversations shaping their markets. Scott says the industry needs to do a better job communicating the jobs, economic activity, and professional standards it brings to local communities while building relationships with officials before a crisis emerges. For Scott, protecting a vacation rental business increasingly means understanding both sides of the equation: what's happening with bookings and revenue today, and what regulatory changes could determine where that business can operate tomorrow.


What you'll learn:

• Why Scott believes advocacy should have a permanent place in every vacation rental company's business plan
• How short-term rental regulations can spread from one city or town to another before their effectiveness has been fully tested
• How AI-powered regulatory risk assessments can help operators and potential buyers evaluate a market
• Why regulatory risk can affect the long-term value and saleability of a property management company
• Why operators should build advocacy relationships before restrictive legislation appears
• How local alliances and programs such as Right to Rent can help fund advocacy efforts
• What current data suggests about booking windows, rates, and the broader vacation rental market
• Why Scott believes continued education, industry involvement, and relationship-building are essential as the vacation rental sector evolves
  
  

About Scott Leggat: Scott Leggat is Director of Government Affairs & Advocacy at Inhabit, bringing 26 years of experience in the vacation rental industry. His career has included managing some of the largest vacation rental companies on North Carolina's Outer Banks, as well as experience as a vacation homeowner, operator, technology leader, and supplier. Scott has served as Chairman of both the Outer Banks Chamber of Commerce and Outer Banks Tourism Bureau, Past-President of the North Carolina VRMA, and a member of the VRMA Board of Directors. His industry work has focused on advocacy, standardized data and analytics, membership growth, and professionalization. 

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 →

In the final part of this three-part conversation, Bill Faeth turns his attention to what comes next for the short-term rental industry. He compares AI's rise to the arrival of the internet: just as online information shifted power away from businesses and toward consumers, he believes AI will make travelers more informed and more selective. Operators with weak reviews, inconsistent service, or outdated processes will have a much harder time hiding those gaps.


For Bill, consistency may be the industry's biggest challenge. Hotels have built loyalty around predictability, while vacation rentals can still vary dramatically from one stay to the next. He believes every poor experience hurts more than one property because guests carry those memories into their next booking decision. At the same time, that creates an opening for boutique operators who can offer the kind of personal service large hotel groups and scaled property managers struggle to replicate.


Lynell and Bill also discuss how tools that once required developers and months of work can now be built in minutes. Bill expects scaling and management to become dramatically easier for operators who adopt these systems, but he doesn't believe human expertise disappears entirely. The technology may do more of the work, but people will still be needed to judge quality, improve outputs, and decide where automation actually belongs.


What you'll learn:

• Why Bill believes AI will shift more power toward travelers and make weak operators easier to expose
• Why consistency may be the biggest competitive issue facing the short-term rental industry
• How poor guest experiences at one property can influence future booking decisions across the entire category
• Why smaller operators may be able to compete with hotel brands through stronger personalization and service
• How Bill uses an AI-powered CEO dashboard to prioritize email, calendar commitments, and upcoming work
• Why Bill expects vacation rental businesses to become much easier to scale and manage as AI tools mature
• Why Bill believes AI will change the industry significantly within the next 18 to 24 months, not five years
• Why automation does not eliminate the need for people who can review, improve, and manage the quality of AI-generated work
  
  

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 →

In part two of this series, Alex Zemianek moves beyond the initial build and shows what happens once an AI agent starts working inside a real business. He walks through how agents can be shared by department, connected to tools such as Gmail, Google Calendar, Google Drive, and task management systems, and gradually given more responsibility. His advice is to start conservatively: use read-only access first, let AI prepare drafts, and keep human approval in place until you're comfortable with the quality of the work.


This conversation then focuses on training. Alex explains how an agent can study weeks of sent emails to learn your writing style, turn repeatable behaviors into reusable "skills," and even learn complex systems by reading their help documentation. For property managers, that opens up practical use cases across bookkeeping, owner reporting, support, and accounting, especially where information is spread across multiple platforms. 


Lynell and Alex also explore marketing and direct bookings. Alex says AI has taken over much of his technical SEO work and can now identify issues across hundreds of pages in minutes. He has also used AI to build websites end to end and optimize them for AI-driven search, which he believes could give direct-booking sites a stronger opportunity to compete with OTAs. The broader point is that AI is no longer useful only for drafting text; it can now support finance, operations, customer communication, reporting, and marketing across the entire vacation rental business.


What you'll learn:

• How to move from building an AI agent to actually deploying it across your daily operations
• Why Alex recommends starting with read-only access before allowing agents to take actions
• How AI memory works and why repeated use helps an agent become more useful over time
• How to train an agent on your writing style by having it study your sent emails and recordings
• What AI "skills" are and how reusable instructions help agents perform recurring tasks more consistently
• How AI can support bookkeeping, trust accounting, reconciliation, financial reporting, and owner communication
• Why Alex tells his team not to spend more than 10 minutes manually researching certain accounting issues before handing them to AI
• How AI-built websites and answer engine optimization could create new opportunities for direct bookings
• Why the real value of AI is often measured in time returned to your team, not just tasks completed
  
  

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

👉 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 →

Alex Zemianek believes the biggest barrier keeping property managers from using AI agents isn't the technology itself. It's the way people talk about it. In this episode, he strips away the terminology and gives agents a much simpler definition: ChatGPT can act like a consultant, while an agent works more like a digital employee. Just like hiring an executive assistant, you need to define the role, decide which systems it can access, and give it clear instructions about the problems it's supposed to solve.


Lynell and Alex then build an executive assistant agent in real time. The goal is practical: connect email, Google Calendar, Slack, and Asana so the agent can produce a daily briefing, identify commitments, prioritize tasks, and prepare drafts without taking actions that haven't been approved. Alex shows that operators don't need to write perfect prompts themselves. Instead, they can explain their goals and frustrations through voice, let AI turn that conversation into a detailed job description, and refine the result from there.


The larger lesson is to avoid trying to automate everything at once. Alex recommends starting with the systems you use most and the problems creating the most friction. From there, treat the agent like a new employee: review its work, correct it, and keep training it. His rule of thumb is equally practical: let AI handle roughly 80% of the work, then use your own judgment for the remaining 20%.


What you'll learn:

• How Alex simplifies the difference between an AI chat tool and an AI agent
• Why building an agent starts with the same questions you would ask when hiring a new employee
• How to create an executive assistant agent around email, Google Calendar, Slack, and Asana
• Why you should start with the business problem causing the most friction instead of trying to automate everything
• How voice dictation can turn a rough explanation of your goals and pain points into detailed agent instructions
• How connected apps give an agent context from years of team conversations, tasks, and commitments
• Why read-only access can be useful for research, FAQs, SOPs, and identifying recurring internal questions
• How to keep human approval in place before an agent sends messages or changes business systems
• Why AI agents need continued feedback and training rather than being built once and forgotten
  
  

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

👉 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 →

Sofia Rossato and Jennifer Cashier join Lynell Gordon to discuss what practical AI adoption should look like inside a vacation rental business. Sofia frames the broader challenge: AI adoption is accelerating, but operators risk creating what she calls “workflow slop” if they simply automate existing processes without first questioning whether those processes should exist in the same form at all. Her advice is to start with the business outcome, identify the real friction points, and then work backward into the data, systems, and automation required to solve them.


Jennifer then brings that thinking into the product layer. She explains how Inhabit’s LEO Agentic AI is being built around customer requests rather than generic AI features, with use cases ranging from bulk listing optimization and real-time product support to custom reporting, property insights, and conversational search. 


This conversation also looks ahead at how traveler behavior and product development are changing. Sofia and Jennifer discuss the shift from SEO toward AEO as more travelers use tools like ChatGPT, Gemini, and Claude to plan trips, the growing importance of natural-language and voice search, and why property managers need to think strategically about where their listings appear in these new discovery channels.


What you'll learn:

• What Agentic AI means and how it differs from a simple chatbot or standalone AI tool
• Why Sofia believes operators should avoid “workflow slop” and rethink processes before automating them
• How Inhabit is using customer advisory boards, focus groups, and direct feedback to prioritize AI development
• Why listing optimization became one of the first major use cases after customers reported that roughly 60% of listings were out of date
• How AI can generate channel-specific listing descriptions at scale while maintaining a property manager’s brand voice
• How support agents can combine code, knowledge bases, and recently resolved tickets to provide more current product guidance
• How property managers can access their own data through APIs to build custom agents, dashboards, and reporting
• Why AEO is becoming increasingly important as travelers use AI tools to search for and plan trips
• How natural-language and voice search could change the way guests find vacation rentals
• Why AI should be evaluated by its effect on owner retention, bookings, customer experience, and enterprise value
  
  

About Sofia Rossato: Sofia Rossato is Executive Vice President of Inhabit’s Short-Term Rental division and a technology executive with more than 25 years of experience growing companies across SaaS, FinTech, PropTech, and communications. Her career includes leadership roles with full P&L responsibility, scaling high-growth businesses, leading product and corporate strategy, and guiding organizations through major periods of transformation. She was named a HousingWire Woman of Influence in 2024, an Inman Best in Finance honoree in 2024, and Most Powerful Woman in FinTech by PROGRESS in Lending Association in 2025.


About Jennifer Cashier: Jennifer Cashier is VP of Product for Inhabit’s Short-Term Rental division, where she leads product vision, strategy, and execution across the portfolio. Her work focuses on aligning customer needs, market opportunities, and business goals while shaping AI-driven products that improve efficiency, customer experience, and growth. Across her career, Jennifer has led product and technology initiatives in healthcare, finance, entertainment, and real estate, with a particular focus on AI/ML, data-driven decision-making, and scalable product innovation.

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 

👉 Fame Host: 👉 Spotify: 👉 Apple Podcasts: 👉 YouTube: 
👉 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 →

Bill Faeth doesn't define a successful vacation rental by its size, amenity count, or occupancy alone. He defines a "super property" as one of the highest-performing properties in its market. Across his portfolio, Bill follows the same basic approach: buy something difficult to replicate, identify exactly who the property is for, and design, equip, and market the entire experience around that guest.


In part two of this three-part conversation, Lynell and Bill break down what creates that performance. Bill explains why strong marketing makes premium revenue management possible, why he designs every property around a single guest persona, and how his "fully loaded" approach uses thoughtful details to remove common guest frustrations before they happen. He also shares how competitor reviews, personalized welcome videos, and direct guest communication help smaller operators create an advantage that larger portfolios can struggle to reproduce at scale.


The conversation then moves from individual properties to the business itself. Bill challenges the industry's obsession with property count, arguing that operators should instead build around the personal, family, and financial outcomes they actually want. That means cutting low-performing properties, being more transparent with homeowners, and investing in relationships that go beyond a monthly owner statement. For Bill, the goal isn't simply to manage more properties. It's to build a stronger portfolio, better owner relationships, and a business that doesn't consume your life.


What you'll learn:

• What Bill means by a "super property" and why it doesn't need to be the biggest or most amenity-heavy rental in the market
• How buying something difficult to replicate can create an advantage that another operator can't simply copy with more amenities
• Why Bill designs, equips, and markets every property around one specific guest persona instead of trying to appeal to everyone
• How studying negative guest reviews can reveal the objections your own vacation rental should solve before guests arrive
• What Bill's "fully loaded" philosophy looks like across kitchens, bathrooms, primary suites, and other small details
• Why personalized welcome videos can create an advantage that becomes increasingly difficult for large portfolios to reproduce at scale
• Why operators should measure success by the outcome their business creates rather than the number of properties they manage
• How removing low-performing properties and difficult owner relationships can create more capacity for profitable growth
• Why owner dashboards, revenue forecasts, and greater transparency can help reduce churn and build homeowner confidence
• Why Bill believes turning clients into friends is one of the most valuable skills a property manager or co-host can develop
  
  

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 →

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. 

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

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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 →