This episode is all about the leap. The grit. And the reality of building a startup from scratch in the short-term rental world. If you've ever stared at a clunky check-in system or juggled five tools just to welcome a guest, this one's going to hit close to home.

Our guest is Michael O’Connell, founder of Happy Guest; a smart, frictionless platform designed to simplify guest journeys from check-in to check-out. Before launching Happy Guest, Michael led strategic sales and partnerships at Turno and worked across the STR tech landscape. He knew the chaos operators were facing and decided to fix it.

This is a raw, honest chat about what it really takes to go from idea ➡️ execution. Michael opens up about the sacrifices, burnout, and brutal clarity needed to survive the startup rollercoaster, without a fancy VC cheque.

SHOW LINKS

Happy Guest – https://www.happyguestofficial.com

Michael O’Connell on LinkedIn – https://www.linkedin.com/in/happyguestmike/

#BuildingItSeries #RunwayToSuccess #GuestExperienceMatters

📋 In this episode, we discuss:

00:00 – Introduction and Background

01:02 – From Vegas to Strive: A Growing Connection

02:30 – Entering the STR Industry by Accident

04:06 – What is Happy Guest? Startup Origins Explained

05:54 – Do You See Yourself as an Entrepreneur?

07:01 – Launching the MVP: Testing with Real Guests

08:56 – Guest-Facing Tech: Why First Impressions Matter

10:42 – Lessons from Beta Testing: What to Launch and What to Kill

12:48 – Building Without VC: Bootstrapping and Personal Sacrifices

15:37 – The Mental Toll: Burnout and Startup Pressure

18:01 – Projections, Runway & Revenue Modelling

21:25 – When the Numbers Don’t Match the Plan

23:51 – Startup Life Is Not Glamorous

25:50 – Why Every Dollar Counts: Sacrifices and Strategy

27:25 – Burnout is Real: Balancing Hustle and Health

30:00 – What I’d Tell My Past Self

32:20 – Final Advice for Future Founders

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🥊 Hotel - BNB - STR Owners! 🥊

Need more direct bookings or a brand new website?

The trusted tech partner you can count on. We deliver results.

🥊 https://www.ibooked.online ​​​​​​​​​​​🥊 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

Don't forget to hit that subscribe button! This also keeps us going and creating more useful content for free!

ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!

📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/

🌍The Accommodation Owners and Managers Facebook Group: https://bit.ly/AMoFacebookCommunity

🗨 Connect with Bart Sobies for more industry insight: https://www.ibooked.online/bart/

🎙 Subscribe to the podcast to listen later: https://www.theaccommodationshow.com

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Disclaimer: The content shared on this YouTube channel, Podcast, or associated posts reflects personal opinions and insights. This content is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions. The hosts and guests disclaim liability for any consequences of using this content. Actions taken should be based on your personal due diligence.

Affiliate Disclaimer:

This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.

This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.

If you do purchase through my affiliate links; I want to thank you for your support.

Running an accommodation business doesn’t have to mean drowning in endless tasks and late-night guest messages. In this episode, I sit down with Lauren Heys and Dan White from Moxxi Property, Tasmania’s largest short-term rental management company, to uncover the systems and tech that allow you to scale without burning out.From automating with tools like n8n, to deploying AI agents, to building onboarding processes that actually save time, this episode is a must-watch for anyone looking to run a smoother, smarter operation. Whether you're managing 5 properties or 150+, you’ll walk away with real strategies and mindset shifts you can apply right now.👀 If you’re serious about building a sustainable STR or accommodation business — and tired of doing it all yourself — this one’s for you.SHOW LINKSMoxxi Property – https://www.moxxiproperty.com.au Resly PMS – https://resly.com.au PriceLabs – https://www.pricelabs.co Key Data Dashboard – https://keydatadashboard.com n8n Automation – https://n8n.io Gemini by Google – https://ai.google.dev/gemini Claude AI – https://www.anthropic.com/index/claude#SmartScaling#PracticalAI#OptimiseWithTech📋 In this episode, we discuss:00:00 Welcome to Building It: Meet Dan de Witte and Lauren Heys 01:05 The Early Days: Chaos, Growth and Lessons 04:18 Scaling STRs with Systems That Work 07:26 How Mindset Impacts Business Growth 10:49 Picking the Right Tech (and Ditching the Wrong Stuff) 14:12 Smart Systems vs. Tech Overload 17:08 Automating Without Losing the Human Touch 20:21 Hiring, Delegating & Building a Real Team 23:34 The Role of Coaching in the STR Journey 26:45 Lauren’s Lean Business Framework Explained 30:04 Future-Proofing: What Hosts Should Focus on Next 33:29 Final Thoughts: Tech, People & Playing the Long Game▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 🥊 Hotel - BNB - STR Owners! 🥊 Need more direct bookings or a brand new website? The trusted tech partner you can count on. We deliver results. 🥊 https://www.ibooked.online ​​​​​​​​​​​🥊 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬Don't forget to hit that subscribe button! This also keeps us going and creating more useful content for free!ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES! 📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/🌍The Accommodation Owners and Managers Facebook Group: https://bit.ly/AMoFacebookCommunity🗨 Connect with Bart Sobies for more industry insight: https://www.ibooked.online/bart/🎙 Subscribe to the podcast to listen later: https://www.theaccommodationshow.com▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬Disclaimer: The content shared on this YouTube channel, Podcast, or associated posts reflects personal opinions and insights. This content is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions. The hosts and guests disclaim liability for any consequences of using this content. Actions taken should be based on your personal due diligence.Affiliate Disclaimer: This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links. This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them. If you do purchase through my affiliate links; I want to thank you for your support.

👇 Ready to grow your short-term rental business without burning out? This episode is for you.

In this episode of The Accommodation Show, we continue our Building It series with Tim Mortimer, founder of BNB Made Easy, one of the fastest growing short-term rental brands in regional Australia.

What started in Tim’s garage with one listing has grown into a thriving operation with 200+ properties across four markets. But what makes his story so compelling is how he built it: thoughtful planning, community roots, operational discipline, and a strong sense of purpose.

🎯 If you're in the accommodation industry, whether it's short-term rentals, motels, hotels or boutique stays, this episode is packed with practical takeaways. Tim shares the exact strategies he used to scale smart, hire well, and systemise the business without losing what made it special.

🔗 Show Links

BNB Made Easy – https://bnbmadeeasy.com.au/

Tim Mortimer on LinkedIn – https://www.linkedin.com/in/tim-mortimer-b8a759190/

The Accommodation Show – https://theaccommodationshow.com/

iBooked.Online – https://ibooked.online/

💬 Drop a comment below and let us know your biggest takeaway.

👍 Like, subscribe and share if you’re building your own accommodation business!

#BuildingItSeries #ShortTermRentals #STRGrowth #BNBMadeEasy #TheAccommodationShow

📋 In this episode, we discuss:

00:00 Meet Tim Mortimer – From Backyard Builds to STR Success

01:05 How a Furniture Side Hustle Became a Full STR Business

04:45 Solving Real Problems in Property Styling & Guest Experience

07:30 Scaling from 1 to 100+ Units – Lessons in Rapid Growth

10:50 Building Systems, Teams & Tech to Run a Growing STR Biz

14:20 Why They Moved to Manufacturing & Built In-House

17:00 Managing Cashflow, Risk & Pressure While Scaling

20:30 Hiring for Culture, Staying Focused, and Letting Go

24:10 Advice for Hosts: Strategy, Simplicity & Scaling Smart

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

🥊 Hotel - BNB - STR Owners! 🥊

Need more direct bookings or a brand new website?

The trusted tech partner you can count on. We deliver results.

🥊 https://www.ibooked.online ​​​​​​​​​​​🥊 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

Don't forget to hit that subscribe button! This also keeps us going and creating more useful content for free!

ACCOMMODATION OWNERS AND MANAGERS FREE RESOURCES!

📧Join the mailing list for freebies and critical industry updates: https://news.theaccommodationshow.com/

🌍The Accommodation Owners and Managers Facebook Group: https://bit.ly/AMoFacebookCommunity

🗨 Connect with Bart Sobies for more industry insight: https://www.ibooked.online/bart/

🎙 Subscribe to the podcast to listen later: https://www.theaccommodationshow.com

▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬

Disclaimer: The content shared on this YouTube channel, Podcast, or associated posts reflects personal opinions and insights. This content is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions. The hosts and guests disclaim liability for any consequences of using this content. Actions taken should be based on your personal due diligence.

Affiliate Disclaimer:

This blog, podcast & youtube channel; will occasionally contain affiliate links, which means I receive a small commission on a purchase without additional cost to you, if you buy something through my links.

This show aims to educate viewers and share everything I know about improving your accommodation, STR and AirBNB business. I believe in the products and services we link to and that you may benefit from them.

If you do purchase through my affiliate links; I want to thank you for your support.