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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