Martin O'Leary | uncharted

For people figuring it out before there’s a map

uncharted is my newsletter for founders, marketers and anyone trying to figure out AI, growth, product and B2B sales without a clean playbook.

Imagine 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. Later, you search for help positioning a product with no obvious category. The advice comes from someone whose hardest sale was a Substack subscription. I am aware of the irony.

AI has made building easier. Trust, demand, adoption and retention remain stubbornly human problems.

That is the territory uncharted covers.

I start with something that looks simple in a strategy deck and follows it until it meets customers, budgets, politics and reality. I use experience from inside the work, useful research and a point of view strong enough to be useful.

I want you to leave with a clearer way to see the problem and something worth taking back into the meeting.

I publish when there is something worth saying, usually once or twice a month.

No fairytales.


New here

For B2B trust, start with Great meeting. No reply. For creative judgement, read How to stand out from AI slop. For the strange politics inside growing companies, read Every startup needs a designated hater.

The Start here guide will take you through the rest.


I’m Martin

I’ve a habit of ending up where the map runs out.

For more than 20 years, I’ve worked in markets and technologies that were still being figured out.

I helped launch Ireland’s first digital bank. I moved to Dubai when everyone thought it was a terrible idea, then led digital marketing for the Burj Khalifa and Dubai Mall. I spent four years helping sell real estate directly to buyers online while most of the market still relied on agents. Today I work inside payments across the GCC, where technology, regulation and customer behaviour are changing at the same time.

I’m not a founder, but I’ve worked alongside founders in three startups. I’ve never raised a round, but I’ve been part of the process. And I’ve no plans to do a TED Talk.

My perspective comes from making unfamiliar products understandable and credible enough to be chosen. I love new technology. Some of it will change the world. Some of it deserves ridicule. Telling the difference is the interesting part.

p.s.

I also work with teams when the product is new, the category is unclear and trust has to be earned before anything can be sold. 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 for founders, marketers and operators figuring out what actually works when AI, growth, product and B2B sales meet customers, budgets and politics.

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