What does it take to build not just one successful vacation rental business, but 14 different companies? Sébastien Grosjean joins The Vacation Rental Show to share entrepreneurial wisdom gained from over two decades in the industry and a family legacy spanning four decades.
What you'll learn:

• Why ego is both essential for starting a business and your biggest blind spot as you grow
• How 90 percent of listings are losing 10-20 percent of revenue due to underoptimized photos and descriptions
• The difference between urgent fires and important needle-movers in your daily operations
• Why working ON your business instead of IN it requires daily learning as a practice
• How cross-pollinating with other industries creates breakthrough innovations you can't see from inside vacation rentals
• The two critical delegation challenges that stop property management companies from scaling
  
  

Sébastien brings a unique perspective as someone who launched the industry's first channel manager and has continued to innovate across multiple businesses. He breaks down why most property managers ignore low-hanging fruit, how to distinguish between problems that need solving and problems that can wait, and why your strongest "doers" often shouldn't be promoted into management roles.

Drawing from personal experience that includes overcoming a severe mental health crisis through his family's successful vacation rental business, Sébastien emphasizes the importance of building a business that creates both financial freedom and time freedom. He shares why having a clear "why" is more important than motivation, how AI will separate thriving businesses from failing ones by 2030, and why investing in expert guidance is the fastest path to growth.

Whether you're just starting out or scaling an established property management company, this conversation delivers practical wisdom on building a sustainable business that serves your life instead of consuming it.

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
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show

For the free photo improvement for your audience (offer valid for 1 month post release of the Podcast, aimed to release mid-February). Offer is valid till 17th March 2026

Use the link https://www.smily.com/r/thevacationrentalshow


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 this episode of The Vacation Rental Show, host Lynell Gordon speaks with Ann Marie O'Rourke, owner of Sandpiper Management, about building a boutique property management company through superior cleanliness standards, transparent owner communication, and personal touches that create repeat guests who eventually become property owners themselves.


What You'll Learn:

• Why cleanliness is the most overlooked aspect of property management and how one unclean discovery makes guests search for every other problem
• The controversial staffing decision that transformed Ann Marie's business: replacing all cleaning teams and paying staff more to ensure everyone became more profitable
• How to balance owner loyalty and guest satisfaction without sacrificing either relationship through customized management approaches
• Small personal touches that cost almost nothing but create lasting memories: handwritten notes, tailored recommendations, and celebration gifts
• Communication strategies that build trust even when you don't have immediate answers to owner questions
• Why treating properties as customized investments rather than one-size-fits-all assets creates competitive advantages against corporate competitors
  
  

Ann Marie O'Rourke purchased Sandpiper Management without traditional property management experience, bringing instead a background in clinical social work and freelance writing. Drawing on her father's forty years in commercial cleaning, she understood the difference between appearing clean and truly clean. She made the bold decision to replace her entire inherited cleaning staff and pay new teams more than competitors, betting that superior cleanliness would drive profitability for everyone. Six years later, many original team members remain, creating consistency that generates reviews consistently stating "this is the cleanest property I've ever stayed in." Her company now manages properties across Kiawah Island and Seabrook Island near Charleston, South Carolina, competing successfully against larger corporations by focusing on quality over quantity and relationships over scale.


This episode is sponsored by Lynbrook Group.

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 →

Ready to capture massive revenue increases during major events while building strategic systems that compound over time?


Sofia Rossato, Executive Vice President at Inhabit overseeing the vacation rental division, shares the playbook property managers need for 2026 and beyond. With her background managing billion-dollar divisions and receiving recognition as one of the most powerful women in fintech, Sofia brings a strategic lens to operational challenges.


What You'll Learn:

• How to prepare for the 2026 World Cup and capture 55% average rate increases with surge pricing strategies
• The 300 mile zone approach for attracting event attendees across multiple markets
• Why RevPAR is 16% higher for operators using Inhabit products and Streamline compared to other systems
• The three-step process for implementing AI in your property management business starting today
• How the IDS framework helps leaders bring teams along in problem solving
• Strategic thinking time versus tactical firefighting and why morning hours matter most
  
  

Sofia Rossato has spent her career at the helm of influential companies in fintech and proptech, managing teams and negotiating multi-million dollar acquisitions. As Executive Vice President at Inhabit, she oversees the vacation rental division and brings together experts across the ecosystem from revenue management to digital marketing services. She's also a dedicated advocate for inclusion and mentorship through her work with organizations like the Broker Action Coalition and Habitat for Humanity.


In this episode, Sofia shares practical strategies property managers can implement immediately, from adjusting rates months before event announcements to using ChatGPT to solve business problems without needing technical expertise. Her emphasis on community connection and making the pie bigger for everyone reflects the collaborative spirit driving the industry forward.


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 →

In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Shervin Jamshidpour, founder of RestNest, about building a luxury vacation rental business through creative property acquisition, authentic guest relationships, and intentionally capping growth to protect service quality that corporate competitors cannot replicate at scale.

What You'll Learn:

• How to leverage unmet guest demand to onboard properties by approaching owners with concrete booking opportunities rather than abstract revenue projections
• Why Shervin's $40,000 first booking validated that luxury travelers book differently than budget tourists and don't primarily discover properties through OTAs
• The foreclosure courthouse strategy where Shervin sat for four hours waiting to pitch property management to whoever won the auction
• Why luxury guests are actually easier to serve than mid-market travelers despite paying $4,000 average nightly rates
• How 99% direct bookings at $4,000 nightly beats OTA dependence that cut rates in half while taking 20% commissions
• The intentional growth cap philosophy - why Shervin plans to stop between 30-50 properties before service quality deteriorates
• Competing against established companies in markets like Whistler where incumbents actually do good work
• The honesty principle - why radical transparency about problems builds more trust than perfect operations ever could
• Building authentic friendships with guests who text for real estate advice year-round, not just vacation bookings
• Creative acquisition tactics that differentiate from competitors sending generic email outreach
  
  

Shervin Jamshidpour quit his compliance officer job during COVID after impulsively telling a friend he could manage vacation rentals better than the current company. With zero professional experience beyond managing two nightmare low-end Vancouver apartments that attracted homeless guests, he moved to Kelowna, set up proper systems from day one, and landed a $40,000 direct booking as his first reservation. He used guest inquiries he couldn't accommodate as leverage to onboard properties one at a time, growing RestNest to 26 luxury homes across Kelowna, Whistler, and Vancouver by being selective about which properties fit his ultra-high-end positioning rather than chasing volume growth.

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 →

In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Steve Zimmerman, CEO and owner of Beach House Logos and Chief Cup Officer at Bar Cups, about building lasting brand impressions that transform one-time vacation rental guests into loyal advocates who return year after year and recommend your properties to friends and family.

What You'll Learn:

• How kitchen amenities like branded spices and K-cups keep your name on guests' dinner tables for months after their stay
• The custom destination map strategy that creates keepsake tote bags, canvas prints, and koozies guests actually want to keep
• Strategic homeowner acquisition approaches using "wow gifts" that get attention in markets flooded with generic postcards
• The "oops gift" service recovery system that turns check-in disasters and operational failures into relationship-building opportunities
• Why one Oregon property manager built a 200-home portfolio focusing exclusively on pet-friendly branding and shoulder season demand
• The underrated power of premium pens, notepads, and simple daily touchpoints that travel with guests everywhere they go
• Post-stay retention campaigns timed strategically for fall when families begin planning next summer's vacations
• Working with marketing teams to integrate branded amenities with digital campaigns and overall brand positioning
• How 25 years of industry experience reveals what actually works versus what sounds good but falls flat in execution
  
  

Steve Zimmerman left corporate America 22 years ago after his sixth or seventh relocation in fifteen years, wanting to watch his kids grow up and coach their field hockey teams rather than chase another promotion. What started as a simple idea about people who name their vacation houses evolved into Beach House Logos, a comprehensive branding partner for professionally managed vacation rental companies across every major destination market in the United States. Steve's team brings almost 75 years of combined vacation rental industry experience, showing up consistently at every major conference and developing products by listening carefully to what property managers actually need rather than pushing generic solutions.

This episode is sponsored by Bluetent.

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

Chapters:[00:00] Intro[02:05] Building Meaningful and Memorable Brand Impressions[06:16] Kitchen Amenities That Travel Home: Custom Spices and K-Cups[08:27] Custom Destination Maps: From Tote Bags to Canvas Art[13:12] Strategic Homeowner Acquisition Through Wow Gifts[19:27] The Yellow Cooler Strategy: Spotting Your Guests on the Boardwalk[21:30] Oops Gifts: Turning Service Failures Into Loyalty Wins[23:34] Building a Pet-Friendly Business Model Around Four-Legged Guests[29:27] Why Guests Remember Stuffed Animals and Take Home Spices[31:36] The Underrated Power of Premium Pens and Simple Daily Touchpoints[34:42] Strategic Advice for Property Managers Elevating Their Marketing Game[38:11] Twenty-Five Years in Vacation Rentals: From Corporate Life to Industry Partner


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 this episode of The Vacation Rental Show recorded at Streamline Summit, host Lynell Gordon speaks with three industry leaders — Koen Roelens, Larry Hoffer, and Mishan Andre — about scaling vacation rental businesses across multiple markets without creating operational chaos, choosing technology partners who actually deliver, and why the people behind your tools matter as much as the features themselves.


What You'll Learn:

• When to invest in operational processes as you scale (Koen's inflection point was 200-250 properties)
• Why acquiring local companies beats building new markets from zero every single time
• The communication foundation that makes everything else work with owners, guests, and teams
• How to use comprehensive property data to target the right homes before competitors do (all 125 million U.S. residential properties)
• Why vendor consistency at trade shows signals credibility better than any sales pitch
• The automation strategies that free up 30-40 daily tasks for strategic work instead of manual operations
• Building leadership teams that are smarter than you in critical areas where you're weak
• Why the people behind your technology matter as much as the platform features
• The real learning curve of PMS implementation and why momentum compounds over time
• Taking time to work on your business through conferences rather than staying in the weeds
  
  

Koen Roelens scaled a hotel industry side hustle to 600 properties across Florida by openly admitting he's terrible at operations and building a young leadership team that excels where he struggles. Larry Hoffer from Z-Point helps property managers grow strategically using data enriched from 15 sources covering every residential property in the United States. Mishan Andre runs luxury properties in Cabo ($15,000+ per night) using Streamline's trigger automation to handle dozens of daily operational tasks automatically, freeing his team to focus on relationships and growth. Together, they reveal that sustainable scaling requires intentionality — building infrastructure that supports expansion rather than just signing more properties and hoping operational systems magically appear.


This episode is sponsored by Streamline.

If you enjoyed this episode, make sure to:

• Subscribe, rate, and review
• Share this episode

Chapters:
[00:00] Intro[02:36] When Operations Become Non-Negotiable: Koen's 200-Unit Inflection Point[04:40] Strategic Market Entry: Why Acquisition Beats Starting from Zero[07:13] The Communication Foundation That Makes Everything Work[08:27] Building Leadership Teams Smarter Than You[10:00] Data-Driven Growth: Finding the Right Properties First[13:37] Vendor Relationships: Why Consistency Builds Credibility[15:12] Implementation Reality: The Learning Curve Is Real But Worth It[17:43] Automation That Works: 30-40 Daily Triggers That Create Freedom[19:27] Why People Behind Technology Matter As Much As Features[22:26] The Personal Touch: Knowing Your Vendor Partners By Name


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 this episode of The Vacation Rental Show, host Lynell Gordon speaks with Jason Gann, Account Executive at RevMax, about his surprising transition from competing against Inhabit's revenue management platform to recognizing it as the industry's most comprehensive solution, the game-changing power of length-of-stay pricing, and why property managers need more than basic dynamic pricing to truly maximize revenue.


What You'll Learn:

• How length-of-stay pricing generates premium revenue from shorter bookings while maintaining owner restrictions and regulatory compliance
• Why RevMax's comprehensive platform outperforms basic dynamic pricing with comp sets, yield mapping, and automated optimization strategies
• The fractional CRO advantage of professional revenue manager support at $30K annually versus $90K+ for full-time hires
• How automated rental projection reporting transforms hours of manual data work into one-click owner communications
• RevMax's expansion beyond Inhabit PMSs to serve property managers across nine integrated systems with direct OTA data
• Real-world results from automated revenue management that captures bookings property managers didn't even know they were missing
  
  

Jason Gann is an Account Executive at RevMax with ten years of vacation rental industry experience and previous work with competing pricing platforms. His transition from viewing RevMax as a non-competitor to recognizing it as the industry's most comprehensive solution offers valuable insights for property managers evaluating their revenue strategy. Jason's enthusiasm stems from discovering features like length-of-stay pricing that he'd never encountered despite years of working with data and revenue management tools. After just four months with RevMax, his perspective shifted from skepticism to genuine excitement about capabilities that go far beyond basic dynamic pricing—including premium lift strategies, automated compliance features, comprehensive data tools, and professional revenue manager support that acts as a true extension of property management teams.


Ready to transform your revenue strategy?


This episode is sponsored by RevMax.

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 this episode of The Vacation Rental Show, host Lynell Gordon speaks with Jay Sudowski, owner of Beachside HHI, about transitioning from managing critical IT systems to vacation rentals, running thirty properties with minimal staff through strategic automation, and defending brand standards even when it costs revenue.


What You'll Learn:

• Why tech industry experience makes vacation rental problems feel comparatively low-stakes and manageable
• The exact staffing model for running thirty properties with just three full-time employees
• Which property types generate the highest ROI in vacation rental markets
• Strategies for shifting legacy week-to-week markets toward flexible stay lengths using concrete data
• When firing a homeowner protects your business more than their revenue helps it
  
  

Jay Sudowski managed IT services for Denver's transportation system and various school districts, where downtime meant hundreds of thousands of people were impacted. When he bought Beachside HHI in 2022 during an exceptionally busy year that also included selling his tech company and training for a half Ironman, he brought systematic thinking and automation expertise that transformed the operation. His team consists of himself, his wife, and one full-time maintenance person, with part-time inspectors, outsourced cleaners, and remote admin support filling the gaps.


Growth happens accidentally through homeowner word-of-mouth and real estate agent referrals rather than aggressive acquisition. Jay deliberately adds properties slowly, ensuring his systems can handle them without compromising quality. He's achieved forty-five percent direct bookings in a traditionally Saturday-to-Saturday market showing that sixty-nine percent of summer stays are now two to five nights. His contrarian advice includes firing homeowners who want "time capsule" service with items in exact positions between stays, because operational chaos isn't worth any amount of revenue.


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 →

In this episode of The Vacation Rental Show, host Lynell Gordon speaks with brother-sister duo Taylor Moore and Danielle Giancola, founders of Nomadic Vacays, about building a vacation rental business from scratch during COVID-19, prioritizing infrastructure before growth, and creating systems that make operations plug-and-play.


What You'll Learn:

• Why building infrastructure for 100 properties from day one accelerates growth even when you start small
• The 18-month immersion strategy where founders work 16-hour days learning every business aspect firsthand
• How a 22-step onboarding process with video tutorials eliminates dependence on key personnel
• Brother-sister partnership dynamics and the good cop bad cop approach to managing family employees
• Creating service businesses within your business ecosystem for family members with different passions
• The partnership alignment mistakes that led to their third partner departing and how to avoid them
• Balancing automation and templates with personalized guest communication touches
• Why vendor selection and relationship management took years to refine properly
• Proactive communication strategies that reach out to guests and owners before they contact you
• Growing into technology features over time rather than activating everything immediately
• The corporate careers they left behind to build a vacation rental legacy
• Why they showed up at 4 AM when guests got locked out instead of sending a service provider
  
  

Taylor Moore and Danielle Giancola are the brother-sister founders of Nomadic Vacays, managing 57 vacation rentals in Naples, Florida. They left high-level corporate careers in sales and consulting in New Jersey during COVID-19 to relocate their entire family and build a vacation rental business from scratch. Despite being told by Streamline initially that they were too small for the platform, they insisted on implementing enterprise-level systems from day one, understanding that having everything in one central location would become their competitive advantage. They partnered with Thorough Accounting, Rental Guardian, and RingCentral to create integrated back-end functions designed for 100+ properties even when they were just starting. Their first 18 months involved working side-by-side 16 hours daily, learning every operational aspect personally so they could train teams effectively. They've built comprehensive video tutorial systems covering all 22 steps of property onboarding, making operations plug-and-play for team members with zero experience. While they've experienced turnover and learned hard lessons about partnership alignment, their infrastructure-first approach has enabled sustainable growth while maintaining genuine hospitality and personal connections.


This episode is sponsored by Rental Guardian.

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
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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 →

In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Amanda Look, founder of Salt Air Properties, about building a 100-property portfolio in Bar Harbor, Maine with a fully employed team rather than contractors, maintaining culture in seasonal markets, and learning when to say no to growth opportunities.


What You'll Learn:

• Why hiring cleaners as W-2 employees costs more but delivers stronger reviews and higher quality control
• How to solve the isolation problem that drives turnover in cleaning positions
• Creative employee appreciation programs that build loyalty in seasonal markets
• The suggestion box system that captures frontline insights from 100 properties daily
• Why Amanda refuses to onboard new properties after June 1st in her market
• How leadership training programs prepare seasonal workers for expanded management responsibilities
• Building proprietary trash and concierge programs when national vendors don't service rural markets
• The transition strategy from owner-operator to CEO with delegated daily operations
• Why running occasional field shifts keeps you connected to operational realities
• How to become selective about growth after proving your business model
• Managing compressed booking windows that shift from 180 days to 36 days
• The support systems required to balance business scaling with family and personal sanity
  
  

Amanda Look is the founder of Salt Air Properties, managing 100 vacation rentals in Bar Harbor, Maine with two office locations and a staff of 30 people. She started in 2009 while working full-time at a bank, managing long-term rentals on the side before testing short-term rentals with her first property. When it booked solid within three days, she knew the model worked. By the time she attended her first major industry conference, she had grown to 40 properties and realized she could transition to full-time property management. Amanda made the strategic decision early to hire all cleaners as employees rather than subcontractors, believing that presentation and quality control are everything in this industry. She now focuses on leadership development for her management team, building proprietary service programs, and transitioning from day-to-day operations to strategic ownership while staying grounded through occasional field work.


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 →