Martin O'Leary | uncharted

For people figuring it out as they go

You’re in a windowless meeting room and some consultant is presenting an AI strategy. It sounds impressive. You can feel it’s mostly nonsense but you can’t explain why. Everyone is nodding.

You Google ā€œhow to position a product nobody understands yetā€ and get advice from someone who’s never sold anything harder than a Substack subscription. Yes I get the irony.

You read that AI will replace your job and build your product while you drink martinis on the beach. Then you spend 40 minutes arguing with a sycophantic chatbot about a landing page.

Everyone can build something now. That bit is true. But building was never the hard part. Getting people to trust it, want it, choose it, and come back to it. That’s the hard part. It was always the hard part.

uncharted is about what’s real and what’s noise. New technology, new markets, and the strange human stuff that usually decides what works before the technology does. No fairytales.


I’m Martin. I tend to end up in places before there’s a map.

Helped launch Ireland’s first digital bank when nobody knew what it was supposed to look like. Joined a fintech startup before fintech was a word. Moved to Dubai, which everyone said was a terrible idea. Spent four years selling real estate directly to buyers online while the rest of the market worked through agents. Now I’m deep inside payments across the GCC, a region still making up the rules as it goes.

I love new technology. I genuinely find it fascinating watching what happens when fast moving tools meet slow moving humans. Some of it is transformative. A lot of it deserves to be laughed at. The interesting part is figuring out which is which.

Not a founder. Never raised a round. No TED talk planned. What I got instead was years of making new things believable before they could be bought. Turns out that’s the hard bit everyone skips.

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P.S. I do this work with teams too. New product, no category, trust needs building. DM me on X or connect on LinkedIn.

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Everyone's nodding in the meeting. You're not sure why. Uncharted is about what's real and what's noise in marketing, technology, and growth. No fairytales.

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