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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