Through changing platforms, new technology, AI agents, and automation, one thing about hospitality hasn’t changed: people still want to connect with people.

In this episode, Jason Muth and Rory Gill sit down with Annie Holcomb, founder of Annie & Co., co-host of the Alex & Annie Podcast, VRMA board member, and longtime vacation rental industry leader. Annie takes us through more than 30 years in hospitality—from working a hotel front desk to vacation rental management, Expedia, Marriott Homes & Villas, channel management technology, and eventually launching her own company.

We also dig into Jason’s experience expanding onto Booking.com, why the platform can open the door to international and business travelers, what operators should understand about distribution, and how OTAs can help build a recognizable brand. Then we look at VRMA, the changing relationship between traditional vacation rentals and STRs, podcasting, AI, and where automation should—and shouldn’t—replace human interaction.

Things we discussed in this episode:

1. Annie’s 30-year hospitality career spanning hotels, vacation rentals, technology, OTAs, consulting, and entrepreneurship.
2. Why great guest service and strong owner relationships remain essential despite massive changes in technology.
3. How Booking.com can connect smaller operators with international travelers, business guests, and new audiences.
4. Why Jason’s Booking.com launch quickly generated more than ten percent of his company’s total bookings.
5. What operators should understand about Booking.com payments, monthly invoices, taxes, fees, and account setup.
6. How OTA exposure can strengthen brand recognition and ultimately support a successful direct-booking strategy.
7. Why building a company brand requires different decisions than building everything around one individual personality.
8. How VRMA is bringing traditional vacation rental managers and newer short-term rental operators together.
9. Why podcasting creates powerful relationships by letting operators share authentic experiences, lessons, and personal stories.
10. How AI should eliminate repetitive work while creating more time for meaningful human hospitality and relationships.

Get in touch with ANNIE:

Podcast - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.alexandanniepodcast.com/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://anniecosolutions.com/

#SmartStayShow #ShortTermRentals #VacationRentals #Hospitality #PropertyManagement #Bookingcom #DirectBooking #VRMA #HospitalityTechnology #ArtificialIntelligence #AI #GuestExperience #PropertyManagers #VacationRentalManagement #STR #Automation

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

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What happens when someone who spent 15 years in corporate HR sees his own layoff coming—and decides to build his next career before it happens?

In this episode, we sit down with Matt Marcelissen to unpack his move from corporate America into full-time real estate investing, short-term rental management, and brokerage. Matt shares how he went from flips and long-term rentals to building StayWell BNB and helping investors find high-performing short-term rentals across Texas.

We also dig into why Houston has become an interesting market for STR investors, including properties around $500,000 that can gross roughly $100,000 annually. Matt breaks down the demand, relatively low seasonality, regulations, and numbers that make Houston very different from traditional vacation markets.

Things we discussed in this episode:

1. Matt left corporate HR to pursue full-time real estate investing.
2. An approaching layoff pushed Matt to build new income streams.
3. Matt launched StayWell BNB to manage underperforming vacation rental properties.
4. Strategic improvements increased one property’s revenue from $90K to $165K.
5. Increasing guest capacity created significantly more revenue without major renovations.
6. Houston offers affordable properties, strong STR revenue, and limited seasonality.
7. Family visits, conferences, events, and staycations drive Houston rental demand.
8. Matt uses Slack, SOPs, Loom, and staff to streamline operations.
9. Mindset coaching changed how Matt approaches growth and business decisions.
10. Service animals, therapy dogs, and ESAs require different hosting approaches.

Get in touch with MATT:

Facebook - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/marcelissen

Instagram - ⁠⁠https://www.instagram.com/marcelissen/?hl=en

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.staywellbnb.com/

#SmartStayShow #ShortTermRentals #AirbnbInvesting #RealEstateInvesting #HoustonRealEstate #FinancialFreedomJourney #W2ToInvestor #STROptimization #CashflowProperties #MindsetForInvestors

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

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Ever wondered how to turn an Airbnb or Vrbo guest into a repeat guest you can actually market to?

In this episode, we sit down with Arthur Kolker, founder of StayFi, to explore how short-term rental operators can build stronger guest relationships and grow their direct-booking business. We dig into how StayFi uses the Wi-Fi login experience to capture guest information naturally, without adding extra forms or friction to the stay.

Rory shares his firsthand experience using StayFi across multiple properties, including some of the real-world challenges around Wi-Fi networks, mesh systems, and smart lock connectivity. Arthur also explains why building a guest database is one of the most important steps operators can take if they want to generate repeat stays and rely less on booking platforms.

We also explore StayFi Express, automated email marketing, anniversary campaigns, gap-night promotions, and StayFinder — a tool designed to help travelers discover direct-booking options from independent vacation rental operators.

Things we discussed in this episode:

Building a guest database for repeat and direct bookings
Using Wi-Fi to capture guest information naturally
How captive portals and splash pages work in vacation rentals
Why traditional email platforms can fall short for STR operators
Setting up StayFi with existing Wi-Fi and mesh networks
Wi-Fi connectivity challenges with smart locks and other devices
Why consistent email marketing matters more than one-off campaigns
Automated emails, anniversary campaigns, and gap-night promotions
Using guest data to increase repeat stays and occupancy
StayFinder and helping travelers discover direct-booking options
Comparing direct pricing while searching on major booking platforms
Creating additional revenue through upsells, experiences, and add-ons
Building stronger relationships with guests after their first stay
Reducing long-term dependence on third-party booking platforms

Get in touch with ARTHUR:

Facebook - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/a.colker/⁠

Instagram - ⁠https://www.instagram.com/a_colker/?hl=en⁠

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://stayfi.com/⁠

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #DirectBooking #BookDirect #EmailMarketing #GuestExperience #OwnYourGuest#StayFi #StayFinder #WiFiMarketing #HospitalityTech #PropTech

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

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💡 What if there’s a way to slash your tax bill while building real estate wealth—without buying a single new property?

In this episode, we turn the spotlight on one of the most powerful, yet often overlooked, wealth-building tools for investors: tax strategy. Eric Oliver of Maven Cost Segregation to break down, in plain English, how cost segregation and 100% bonus depreciation can dramatically reduce your taxes—especially if you own or plan to own short-term rentals.

Eric explains how accelerated depreciation really works, what the so-called “short-term rental loophole” is (and isn’t), and why material participation and intent are key in the eyes of the IRS. Jason and Rory go even further, sharing real numbers from their own portfolio, including how they used a look-back study and a “poor man’s reverse 1031” strategy to offset a large tax bill after selling a property.

If you’ve ever thought taxes were just an unavoidable cost of investing, this episode will make you see them as a strategic wealth-building tool.

Things we discussed in this episode:

1. Cost segregation basics – accelerating depreciation by breaking a property into components with shorter lives.
2. Bonus depreciation – how 100% bonus magnifies cost seg savings in year one.
3. STRs vs. LTRs – why short‑term rentals can offset W2 income but long‑term rentals usually can’t.
4. “Short‑term rental loophole” – a legal, code-based strategy, not a shady trick.
5. Material participation – key IRS tests, especially 100 hours and more time than anyone else.
6. Timing a purchase – buying late in the year to more easily document material participation.
7. Jason & Rory’s $900k deal – large depreciation created, especially from exterior work and landscaping.
8. “Poor man’s reverse 1031” – using cost seg to help offset capital gains from a property sale.
9. Look‑back studies & Form 3115 – reclaiming missed depreciation from prior years.
10. Tax planning strategy – using cost seg selectively to manage tax brackets and avoid wasting deductions.

Get in touch with ERIK:

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/people/Maven-Cost-Segregation-Tax-Advisors/61570153671981/

Instagram - https://www.instagram.com/mavencostseg/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://mavencostseg.com/erik/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #CostSegregation #BonusDepreciation #TaxStrategy#RealEstateTax #AirbnbHost #STRLoophole #WealthBuilding #MavenCostSegregation

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.