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 merging

I 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 scenes

If 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 Boostly

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://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 Boostly

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://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 Boostly

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://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 Boostly

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠

🎙 Welcome back to the Episode 796 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 Ruben Kanya, co-founder of Invested Escapes and a nationwide leader in temporary housing. Together they unpack how short-term rental operators can pivot into the booming B2B market by targeting corporate relocations and insurance placements.

Ruben shares how he and his wife went from ordinary STR hosts to scaling a profitable business by focusing on relocation agencies and insurance companies. He reveals the data behind the $7.2 billion insurance housing market, why “monthly rentals” is now the keyword you need to win, and how four- to six-bedroom homes create premium opportunities. You’ll also learn his “duplicate listing” strategy for Airbnb, why visibility and searchability matter more than ever, and how to make your business easy to work with for corporations.

Let's jump in.

https://investedescapes.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 Boostly

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠

🎙 Welcome back to the Episode 795 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 Dr. Rachel to explore how AI tools are transforming the mid-term rental space. Building on Day 1 with Ryan Luke, this session dives into the opportunities hosts have when they pivot from short stays to 30+ day bookings.

Dr. Rachel reveals how she uses custom GPTs to uncover the most profitable guest avatars in any market — from displaced insurance families to construction crews, academic housing, seasonal workers, and even sports teams. She explains how AI can build a seasonality playbook for your property, map out which guest types to target, and give you insights into bookers’ budgets, must-haves, and decision-making processes.

Let's jump in.

www.shorttermgems.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 Boostly

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/5steps⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://instagram.com/boostlyuk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Boostly.co.uk/podcast⁠⁠⁠⁠⁠⁠⁠⁠