Tristan Kavanagh helps run two stargazing dome stays in NSW. He also built Host Port after struggling to find affordable booking management software for small hosts. He joins Ray and Silvia to talk about hosting, direct bookings, and building the tools he needed.

We discuss his path into hosting, managing bookings across different platforms, guest communication, and how much to automate when you run a small accommodation business.

Connect with Tristan

• Host Port website
• Host Port on Instagram — @host_port

Tristan’s stays

• Romantic Stargazing Dome Retreat — Megalong Valley
• Beyond Bubbles Stargazing Dome with Hot Tub — Bucketty

Stay with Ray and Silvia

• Ray’s properties
• Silvia’s Sydney Airbnb

Follow the hosts

• Ray on Instagram — @rayzworld
• Superhosts Down Under on Instagram

Follow Superhosts Down Under for more conversations with hosts across Australia and beyond.

This week Silvia and Ray open with a myth worth killing: that hosting and property management run on autopilot, and that anyone in the business is really just a rent collector. Ray goes back to collecting cash rent from a roofer at twenty one, Silvia makes the case that it is a job that takes real experience, and Carlos adds the line that frames the rest of the episode. Automation does not remove the work, it just moves it. The judgment layer is the real job.

From there we turn to Carlos Castillo, co-founder of DirectBookMe, a subscription based direct booking platform he and his wife launched in October 2024 with no tech background, no real estate background and no outside funding. Around 150 hosts are on the site today.

Carlos is candid about the parts most founders leave out: the valley you walk into after the idea high, hiring web development agencies when you cannot write the code yourself, and the fact that growth has been slower than he expected. He is equally clear that he is not asking anyone to leave Airbnb. Run direct alongside it, move fifteen to twenty percent of your bookings across, and own the guest relationship that the big platforms keep for themselves.

What we cover

• The myth that hosting runs on autopilot, and why the labour never disappears
• Ray on collecting cash rent at twenty one, and why doing the job yourself makes you a better client later
• Whether AI can take over hosting, and where the human part starts
• The moment Carlos realised he was building on rented land
• How DirectBookMe works, with no commission on either side
• The two pricing tiers, and why subscription rather than per booking
• How payments work, with Stripe for subscriptions and the booking left to the host
• What stays on the host: rental agreements, deposits, insurance, damage coverage
• Why the platform is deliberately not algorithm driven
• Owning your guest data, and capturing repeat guests
• Trust and safety, and the gap where AirCover sits
• Running direct alongside the OTAs, iCal sync and PMS integration
• Building a platform with no technical background
• What is next: ID verification, easier onboarding, and a vetted partner resources page

Find Carlos
DirectBookMe: https://www.directbookme.co
Instagram: @directbookme

Sponsor
This episode is recorded with Riverside. Use code RAY15 for 15% off.

Stay with us
Ray's place, Scandinavian Suite in South Yarra: https://www.raymondyee.com.au/airbnb
Silvia's Airbnb: https://www.airbnb.com/slink/Kpse4K4X

Follow the hosts
Ray on Instagram: https://www.instagram.com/rayzworld

This week, we head to the other side of the world to meet Ruben de Bruin. For the past four years, Ruben has run Cozy Maisonette by the Sea, a one-bedroom beachside retreat in Boscombe West on the UK’s south coast—all while living in London.

Ruben has turned long-distance hosting into a reliable system, combining a trusted local team, automation where it counts, and a personal touch where it matters. That same attention to detail also inspired a business: The Curated Host, which creates digital and printed guest handbooks for short-term rental hosts. These thoughtfully designed guides help reduce late-night questions like, “How does the heating work?” while improving the guest experience and supporting better reviews.

Silvia and Ray talk with Ruben about remote property operations, the realities of the UK coastal market, and why a well-designed welcome book is one of the highest-leverage investments a host can make.

• How Ruben got into hosting—and why he chose Boscombe West on the Bournemouth coast
• The types of guests a one-bedroom beachside retreat attracts and the seasonality of the market
• Ruben’s biggest surprises during his first year compared with now
• Managing changeovers, maintenance, and day-to-day operations from London
• How to find and vet reliable cleaners and handymen from a distance
• Building a remote property team that can handle problems when they arise
• Where Ruben draws the line between automation and the personal touch
• The gap in the market that led him to create The Curated Host
• Digital versus printed handbooks—and why guests use both
• How clear, well-designed communication can improve reviews and star ratings
• The essential sections every guest welcome book should include
• Handling awkward guest conversations, including linen changes during longer stays
• Why investing in quality pays off in short-term rentals
• Ruben’s number-one tip for buying your first remote investment property

• Cozy Maisonette by the Sea on Airbnb
• The Curated Host
• Follow Ruben on Instagram

• Ray’s Airbnb
• Silvia’s Airbnb