Martin O'Leary Startup Marketing

uncharted

You know the product works. You know the reasoning is sound. But every conversation feels like compressing months of context into minutes while the buyer quietly looks for reasons to say no.

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

I helped launch Ireland’s first digital bank.
Scaled a fintech across the Middle East.

I jumped into real estate with no background and built a digital revenue engine anyway. Now I’m deep inside fintech again, figuring out what AI actually changes and what it doesn’t.

For the last 15+ years, I’ve been the marketer in the room with founders and CEOs.
Often the only one. Usually in regulated, complex, high-pressure environments.

I’m not a founder.
I’ve never raised a round.
I’ve never sold a company.
No TED talk planned.

Just a front-row seat to what works, what fails, and what people quietly get wrong when the standard playbook stops applying.

What Uncharted Is About

Uncharted is about how to build and sell in uncertainty, especially when the product is hard to explain and getting it wrong is expensive.

I write about:

  • Why people say yes, stall, or walk away

  • How to sell things that are hard to explain

  • What kills deals after the meeting

  • Tech that works versus tech that performs

  • AI, strategy, and decisions under pressure

  • The myths founders and marketers keep paying for

Some posts are a teardown. Some are field notes from the work. Sometimes I’m just naming the thing everyone is pretending not to see.

The common thread is trust, in plain terms.

How belief gets built, how it breaks, and what makes a decision defensible when certainty is missing.

Who This Is For

Founders and marketers who are:

  • Building or scaling in complex, regulated, or fast-changing markets

  • Tired of silver bullets, growth hacks, and borrowed certainty

  • Making decisions without perfect data and owning the consequences

  • Trying to do real work without turning into a parody of their industry

If you’ve ever thought “none of this advice fits our situation”, you’re in the right place.

Over 5,000 founders and marketers read Uncharted because it doesn’t pretend there’s one right answer.

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P.S. I help teams figure out how to sell things that are hard to explain.

DM me on X or connect on LinkedIn.

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Why people trust. How to sell what’s hard to explain. No fairytales.

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