The Boostly Podcast

In this episode of the Boostly Podcast, I joined the Stay Direct monthly meet-up to talk about where AI is really heading in the short-term rental industry, and what hosts, property managers and direct booking businesses should be paying attention to right now.Skool Group - https://www.skool.com/drive-direct-bookings-for-strs-5526This was a thorough deep dive into AI, WordPress, PMS platforms, direct-booking websites, guest communication, content, search, community, and the future of hospitality tech.Big shoutout to Stay Direct for inviting me into their monthly session and for leading such a strong conversation around what is changing in the industry.We also mentioned and discussed:Graeme from Forge, and the work they are doing with AI agentsNeely Khan, and the importance of storytelling and being chosen, not just discoveredRichard VaughtonBoris from OnseasonGil from Crafted StaysGareth, who joined the discussion around AI search and discoveryGareth's Linkedin https://www.linkedin.com/in/ACoAABnNNhwBMQ1NDdjPM8JO3TjGvDSe0NZB50c?skipRedirect=trueGuesty, and how PMS platforms are moving into AIHospitable, including an example of a host using AI to find booking opportunitiesClaude, ChatGPT, Perplexity, OpenClaw, Lovable, Replit, HubSpot and other AI tools are changing how operators workThe main message from the session is simple:AI is not here to replace your story, your brand, or your relationships.But it can help you remove boring work, spot missed revenue, follow up with guests, review costs, research leads, and make better decisions faster.We talked about:Whether WordPress is still the best option for direct booking websitesWhy AI website builders are exciting but not always ready for proper booking flowsHow PMS companies are adapting to AIHow hosts can connect PMS data to AI toolsHow one host generated $7,000 in bookings within 72 hours using AIWhy AI generated content is often weakWhy community and brand are becoming more importantHow ChatGPT, Claude, Gemini and Perplexity are changing online discoveryWhy niche brands will be easier for AI tools to recommendWhat short-term rental hosts should focus on over the next 12 monthsThis session was part of the Stay Direct monthly meet-up.You can join the Stay Direct school group using the link in the description below.Watch this if you are a host, property manager, website builder, PMS user, or short-term rental business owner trying to understand how AI fits into your direct booking strategy.Alistair's Linkedin https://www.linkedin.com/in/alistairmalins/

👋 Welcome to Boostly, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings.In this episode, Gil Chan of Crafted Stays and I explore how SEO is changing in the age of AI search. We break down the rise of AEO and GEO, why guests are asking tools like ChatGPT, Gemini, and Perplexity for recommendations, and what accommodation businesses need to do to stay visible.You’ll learn why deep, niche content matters more than generic landing pages, how schema and crawlability affect AI discovery, why Bing Webmaster Tools should not be ignored, and how AI is becoming the new “influencer” in the booking journey.

In this episode, we’re joined by Amber Knight from Bookings Cloud to discuss how vacation rental managers can move beyond reactive marketing and start building a stronger, more profitable direct booking strategy.Amber shares her experience across the short-term rental industry and explains why guest acquisition can no longer be treated as an afterthought. We dive into the difference between boosting posts and running effective Meta ad campaigns, how clean property data can improve ad performance, and why your website and property detail pages are critical assets for converting qualified traffic.Amber also breaks down the data points that many operators overlook, including booking pace, booking-source dynamics, OTA fee impact, revenue per property, and profit per property. She shares a real example of how a North Carolina client increased RevPAR by $60 while the wider market declined by 17%.Whether you manage one property or a large portfolio, this episode offers practical advice on preparing your listings, improving website trust, and using marketing to drive higher-quality bookings instead of simply filling last-minute gaps.Learn more about Bookings Cloud at http://bookingscloud.com/ or connect with Amber Knight on LinkedIn.

👋 Welcome to Boostly, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings Check out Stayfinder here https://www.stayfinder.com/Stayfi is https://stayfi.com/💡 This video is part of our free training series to help you grow your short-term rental business and take control away from OTAs.🎟️ Save Your Spot: Boostly’s Free 90-Minute WorkshopMaster the systems top hosts use to hit 65%+ direct bookings:👉 https://boostlybootcamp.com/workshop/📊 Try the Bookings Booster Score Card15 questions. Instant insights. Personalized plan.👉 https://www.bookingsbooster.ai/📞 Ready to scale your direct bookings? Let’s talk.Book a free strategy call with our team:👉 https://boostly.co.uk/call🤖 Ask the Boostly AI, anytime.Your 24/7 hospitality chatbot:👉 https://boostly.co.uk/bot📢 No gatekeeping. No ads. Just the tools to help you build the hospitality brand you deserve.DISCLOSURE Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies, and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary.Copyright © 2026

In this episode of the Boostly Podcast, I’m joined by voices from across the industry to break down what’s coming next and what hosts and property managers need to prepare for now.Drawing on insights from operators, tech leaders, consultants, and founders, we cover the biggest shifts already happening beneath the surface, including:• AI moving from hype to table stakes• Direct bookings becoming a survival strategy, not a nice-to-have• Automation reshaping guest communication, marketing, and operations• Rising guest expectations and the return of high-touch experiences• Consolidation across software and management companies• Regulation, tourist taxes, and what they could mean for supply• Longer stays, digital nomads, and stronger shoulder seasons• Why revenue management and marketing are finally mergingI also share my own prediction for 2026 and why I believe this is the year the industry fully crosses into a new operating model.If you’re a host or property manager who wants to stay profitable, future-proof your business, and reduce reliance on OTAs like Airbnb and Booking.com, this episode will help you see what’s coming before it hits.Listen now and decide which side of the change you want to be on.

Hiring is the single biggest decision that either scales your STR business or silently destroys it. Most hosts wait too long, hire too cheap, or onboard the wrong way. In today’s episode I sit down with Matt Metros of CS Outsource, who works with more than 500 property management companies worldwide, to break down exactly how to hire properly, avoid the common traps, and build a team that actually frees you up.You’ll learn:• When to hire your first assistant• Why cheap VAs cost you more• The real onboarding process hosts never do• The traits of great operators• How to stop micromanaging and actually lead• Why your SOPs are simpler than you think• What agencies like CS Outsource really offer behind the scenesIf you’re managing 5 to 10 properties and feeling stretched, this video is the one that will save you months of headaches.Work with the team I trust for all my hiring:https://boostly.co.uk/hiring

Welcome back to the Episode 801 of Boostly Podcast! 🎙👋 Welcome to the Boostly Spotlight, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings — no fluff, no ads.In this Boostly Spotlight episode, we shine the spotlight on Garrett Brown from BiggerPockets — diving into his insights on real estate investing, short-term rental growth, and how community-driven education empowers everyday investors to build wealth through property.Let's jump in.https://www.biggerpockets.com/💡 This video is part of our free training series to help you grow your short-term rental business and take control away from OTAs.Connect with Boostly⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠

🎙 Welcome back to the Episode 800 of Boostly Podcast! 🎙👋 Welcome to Boostly, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings — no fluff, no ads.Episode 800 of The Boostly Podcast is a celebration of eight years behind the mic—starting with a Skype setup in 2017 and growing into a global community with over a million YouTube views. Mark Simpson and co-host Liam Carolan sit down in person for the first time to reflect on the journey so far: hundreds of guest interviews, thousands of minutes of direct booking tactics, and the lessons learned from scaling hospitality businesses through consistency, better follow-up, smart systems, and a relentless focus on guest experience.Let's jump in.https://boostly.co.uk/💡 This video is part of our free training series to help you grow your short-term rental business and take control away from OTAs.Connect with Boostly⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠

🎙 Welcome back to the Episode 799 of Boostly Podcast! 🎙👋 Welcome to Boostly, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings — no fluff, no ads.In this Boostly Spotlight episode, Liam is joined by James King, Senior Marketing Manager for Eviivo in the US and Canada. With over 20 years of STR and hospitality experience, Jamey unpacks how Eviivo has grown into one of the leading all-in-one PMS platforms for independent hosts, boutique hotels, and professional managers.You’ll hear how Eviivo simplifies operations across diverse portfolios — from cabins and RVs to boutique hotels — and why automation, integrations, and a unified dashboard save hosts hours every week. Jamie shares how Eviivo helps operators grow direct bookings, cut down OTA reliance, and deliver five-star guest experiences consistently. He also explains why the US market is unique, what hosts often get wrong about tech, and how to use integrations like PriceLabs to maximize occupancy and ADR.Let's jump in.https://eviivo.com/💡 This video is part of our free training series to help you grow your short-term rental business and take control away from OTAs.Connect with Boostly⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠

🎙 Welcome back to the Episode 797 of Boostly Podcast! 🎙👋 Welcome to Boostly, where we give STR and MTR owners and managers the tools, strategies, and support to win more direct bookings — no fluff, no ads.In this Boostly Bootcamp session, Mark Simpson is joined by Hailey Marie Anderson, a 22-year-old Airbnb entrepreneur who built a 7-figure arbitrage business with 58 properties — all fully remote. Hailey reveals how she went from high school side hustles to running an empire by mastering three key steps: automate, delegate, and scale.She breaks down the difference between CEO vs operator mindset, how to run time audits to spot your biggest time wasters, and why burnout, micromanaging, and limited scalability disappear once you hire a remote team. You’ll discover the exact roles she outsourced first (VAs, cleaners, handymen, runners), where to find them, and how to train and retain them with SOPs and checklists.Hailey also shares her tech stack — Hostaway, PriceLabs, Turno, Truvia, TouchStay, Bestie AI, and Discord — and explains how she integrates teams and tools to keep occupancy above 90% while traveling the world as a digital nomad. From guest communication automations to video guidebooks and guest verification, every process is systemized for five-star consistency.Let's jump in.💡 This video is part of our free training series to help you grow your short-term rental business and take control away from OTAs.Connect with Boostly⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠