Martin O'Leary Startup Marketing

Marketing without a playbook

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, back when nobody quite knew what digital banking was supposed to look like, including the people building it. Then I joined a fintech startup before fintech was a word anyone used in a sentence.

Then I moved to Dubai, which everyone said was a terrible idea.

The whole real estate market sold through agents. I spent four years selling directly to buyers online instead. It worked, which surprised me about as much as it surprised anyone else. Now I’m deep inside payments across the GCC, a region still making up the rules as it goes.

I didn’t know what I was doing in most of those rooms. Neither did anyone else. That turned out to be fine.

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.

I came to all of it sideways. I’d studied to be a teacher, then spent years teaching myself design, then somehow ended up running marketing for a bank with no formal training in any of it. The qualifications came later. At some point I stopped being surprised by starting things I didn’t know how to do.

What uncharted is about

I write about

  • What kills deals after the meeting

  • AI and what it actually changes versus what it doesn’t

  • Marketing in markets where the playbook hasn’t been written yet

  • 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 ā€œnone of this advice fits our situationā€, you’re in the right place.

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P.S. I help teams figure out how to build and market in places where the playbook doesn’t exist yet.

DM me on X or connect on LinkedIn.

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What actually works when there's no playbook. No fairytales.

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