Still figuring it out?

I’ve spent 20 years in startups and big companies and I’m still figuring things out... and if you run a startup or lead a team, you probably are too.

Your customers switch to a product you think is way worse than yours, and you don’t know why, you’ve built something groundbreaking and nobody notices because you haven’t the contacts or the budget, the best idea in the room loses to the most senior person in it, and the important stuff gets pushed back again.

And then there’s AI. I remember thinking god mode in a terminal was amazing, and that was only 3-4 years ago... now you can reverse engineer almost any product or change your Android TV with Claude Code. I’ve lost count of the models and agents I’ve tried, some of it is seriously useful and some of it’s vapourware. So where do you actually put your time and money?

And do you really need to hire a creator or start another podcast because a VC said so on theirs? It’s hard to know which new thing deserves your time... remember NFTs?

That’s why I write uncharted.

Writing it down helps me work out what I actually think, and I get to follow my curiosity a bit. I love it when I come across a business in some other industry doing something a bit mad and I think, hang on, could that work for us? But an idea doesn’t have to be new to be useful... sometimes the thing we’ve overlooked for years makes more sense than the latest trend.

BTW I’m Martin O’Leary.

I’m Irish, based in Dubai, and lead marketing in fintech.

I’ve spent more than 20 years in startups and big companies across Europe and the Middle East, including management roles at three fintech businesses, and I helped grow Ireland’s first digital only bank.

I’ve been on both sides of plenty of arguments (including the side that turned out to be wrong) and honestly there’s a lot I wish I’d known earlier.

One free article a month, with shorter Notes in between.

Something to take back to your own work, even if it’s a question you hadn’t thought to ask.