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Martin πŸ‘€

@martinoleary

Fintech CMO. Built Ireland's first digital bank. Scaled startups to $300M+ (Dublin/Dubai). Sharing lessons in 'Uncharted': Real growth, no fairytales. Dubai-based πŸ‡¦πŸ‡ͺ My Uncharted Newsletter -> https://www.dotmartin.io

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Latest posts by Martin πŸ‘€ @martinoleary

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Plaid raised $575M at $6.1B.

That's less than HALF their $13.4B peak in 2021.

This isn't growth money. It's financial housekeeping.

This money is covering employee tax bills on expiring RSUs.

Not exactly rocket fuel for a fintech darling.

05.02.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Startup motto should be: β€œBuild what hurts, not what looks cool on Product Hunt.”

04.02.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Getting into Google is cool. Making them feel threatened is cooler.

03.02.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

AI won’t disrupt SaaS overnight. It’ll show up as a line item in some VP’s budget and suddenly five roles go missing.

02.02.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Most business failures aren't market failures or execution failures. They're imagination failures.
Entrepreneurs hit invisible ceilings they've built in their own minds long before hitting actual market ceilings.

30.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Most startup marketing problems aren’t funnel problems.

They’re identity crises. If you can’t name your customer in one sentence, you’re already lost.

29.01.2026 14:27 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

All the APIs in the world will not save you from the curse of marketing to β€œeveryone.”

28.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Hit 40% MoM growth? VCs suddenly "believe in your vision"

Land a $50M exit? Industry crowns you "visionary genius."

Meanwhile, Mom still asks when you'll get a job with dental insurance.

27.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Startup trauma is character development. You’re just building lore for your future podcast.

26.01.2026 14:27 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Every founder thinks they’re building a product company. They’re not. They’re building a psychology company with a backend.

23.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

The bugs you fix in people take way longer than the ones in production.

22.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Love seeing startups with $150k+ executives doing $15/hour tasks because "we're not ready to hire for that yet." The most expensive way to run a company is having your best people do your simplest work.

21.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

You can't A/B test your way to product-market fit or discover breakthrough features by testing small variations.

The best insights come from customer conversations, not dashboard metrics.

20.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

First-time founder:

6 months building, 58-page deck, 12 rejections, $500K raised.

Second-time founder:

"I'm doing a thing again" in a whatsapp.

$5M committed before appetisers.

VCs fetishise past exits.

19.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Agentic workflow:

because saying β€œautomated to-do list” wasn’t sexy enough for a deck.

16.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Running your own biz: 50% thrill, 50% therapy bills. Clocking in suddenly sounds like a spa day.

15.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Most people think startups are risky. But betting your whole life on one boss’s mood? That’s the real gamble.

14.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Your job is stable… until Dave from Finance gets promoted and suddenly you’re β€œnot a culture fit.”

13.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Want honest feedback on your product?
Add a buy button.

12.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Weird Ideas Win

2025+ is about knowing what weird idea to build, not how to build it.

With modern tools, anyone can launch a product.Β 

The space is crowded with capable builders.

Distribution still matters.

But creativity is the magnet that attracts users organically.

09.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Every founder has two browser windows open during investor calls:

Window 1: The pitch deck they spent 200 hours perfecting

Window 2: Google search for "[insert whatever the investor just asked] + definition + example"

08.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

"We're angel investors who hold a permanent board seat, can never be diluted, and require weekly status updates"

This is what your parents think when you tell them you're starting a company.

07.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

The startup that 'came out of nowhere' and landed that big company as their first client? The founder's college roommate is the VP of Product. The most valuable startup asset is the web of favors you've accumulated over the years. This is how things actually work.

06.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Companies: "People are our greatest asset!"

Also companies: Delays hiring for months to "save money"

Then: Pays 3x more when senior talent quits from burnout

This never appears on the quarterly report.
Penny wise, future foolish.

05.01.2026 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

High-performing teams aren't built through consensus or forced proximity. They're built by interesting characters who can fight over ideas Monday and still choose to grab drinks together Friday.

02.01.2026 14:27 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

"Product-led growth" rarely works without relationship-led sales. The founders claiming they "grew without salespeople" usually had phenomenal customer success teams doing sales without the title.

01.01.2026 14:27 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Love watching founders dismiss their engineers' concerns only to blame "technical debt" six months later. Same founder who said "just make it work" now wondering why everything breaks. Meanwhile the engineering team has that group chat nobody knows about where they called it all.

31.12.2025 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

The biggest reason businesses fail isn't lack of funding or poor timing. It's experts being ignored by leaders who don't want to hear "no."

30.12.2025 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Tech startups keep chasing AI features while basic user problems sit unfixed. Your customers don't want machine learning. They want their password reset to work the first time. Solve the boring problems before building the exciting ones.

29.12.2025 14:27 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Everyone obsesses over what VCs think but nobody pays attention to what early customers actually say. Founders spend months perfecting pitch decks while ignoring support tickets. The funding isn't the validation. The repeat purchase is.

26.12.2025 14:27 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0