If you’ve ever had an idea nagging at you, something you wish existed but doesn’t, this one’s going to resonate with you. Sometimes, the best businesses aren’t born from grand visions; they’re born from friction. From frustration. From late nights staring at a screen thinking, “There has to be a better way.”

Michael O’Connell didn’t just think it, he built it. After most recently leading strategic sales and partnerships at Turno, he saw the chaos that accommodation operators were enduring just to check guests in. Five different tools. Manual signatures. Midnight messages. And that’s before the stay even begins.

So he made the leap. Sacrificed certainty. Backed himself. And built Happy Guest: a smart, clean platform that helps thousands of operators streamline guest comms, check-ins, house rules, agreements and more without the chaos.

In this episode, Michael shares what it looks like to go from idea to launch. Not just the wins, but the missteps, mindset shifts, and brutal clarity you need to get there. We unpack his product process, how he kept overhead low, why building something users want before they ask for it matters, and how to let go of perfection to just start.

What you will learn from this episode:

How downsizing can fuel your startup runway 💰
The mental pivot from employee to founder mindset 🧠
Why MVPs aren’t about perfection, but progress 🚀
How to build without outside funding 🔧
The burnout traps many business owners face and how to avoid them ⚠️
What most founders get wrong about building tech 💻
 

Michael O’Connell is the founder of Happy Guest, a guest experience platform disrupting the STR space. With a background in communications, theology, and partnerships, he blends heart and hustle in equal measure. Michael isn’t here to talk about vanity metrics or buzzwords, he’s here to build things that work. His work at Turno shaped how he thinks about scale, ops, and relationships and now, with Happy Guest, he’s doubling down on simplifying the parts of hospitality that most overlook.

If you’ve ever made sacrifices to build something better or thought about what’s truly worth investing in, this episode is for you. It’s a raw, honest look at startup life in the accommodation world, and why building slower and smarter often leads to the best results.

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