iiinova — where your digital self keeps evolving

Martin 👀 @martinoleary.bsky.social · 05/02/2026

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.

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Martin 👀 @martinoleary.bsky.social · 04/02/2026

Startup motto should be: “Build what hurts, not what looks cool on Product Hunt.”

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Martin 👀 @martinoleary.bsky.social · 03/02/2026

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

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Martin 👀 @martinoleary.bsky.social · 02/02/2026

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.

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Martin 👀 @martinoleary.bsky.social · 30/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 29/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 28/01/2026

All the APIs in the world will not save you from the curse of marketing to “everyone.”

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Martin 👀 @martinoleary.bsky.social · 27/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 26/01/2026

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

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Martin 👀 @martinoleary.bsky.social · 23/01/2026

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

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Martin 👀 @martinoleary.bsky.social · 22/01/2026

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

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Martin 👀 @martinoleary.bsky.social · 21/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 20/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 19/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 16/01/2026

Agentic workflow: because saying “automated to-do list” wasn’t sexy enough for a deck.

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Martin 👀 @martinoleary.bsky.social · 15/01/2026

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

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Martin 👀 @martinoleary.bsky.social · 14/01/2026

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

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Martin 👀 @martinoleary.bsky.social · 13/01/2026

Your job is stable… until Dave from Finance gets promoted and suddenly you’re “not a culture fit.”

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Martin 👀 @martinoleary.bsky.social · 12/01/2026

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

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Martin 👀 @martinoleary.bsky.social · 09/01/2026

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. The space is crowded with capable builders. Distribution still matters. But creativity is the magnet that attracts users organically.

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Martin 👀 @martinoleary.bsky.social · 08/01/2026

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"

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Martin 👀 @martinoleary.bsky.social · 07/01/2026

"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.

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Martin 👀 @martinoleary.bsky.social · 06/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 05/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 02/01/2026

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.

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Martin 👀 @martinoleary.bsky.social · 01/01/2026

"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.

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Martin 👀 @martinoleary.bsky.social · 31/12/2025

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.

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Martin 👀 @martinoleary.bsky.social · 30/12/2025

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."

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Martin 👀 @martinoleary.bsky.social · 29/12/2025

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.

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Martin 👀 @martinoleary.bsky.social · 26/12/2025

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.

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Martin 👀 @martinoleary.bsky.social · 25/12/2025

The founder grinding 80 hours weekly often loses to the founder having coffee with the right VC for 30 minutes. Success is about who takes your call.

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Martin 👀 @martinoleary.bsky.social · 24/12/2025

The biggest startup mistake is love with a clever idea that solves nothing. If nobody’s already duct-taping a workaround for your “big vision” it’s probably not urgent enough.

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Martin 👀 @martinoleary.bsky.social · 23/12/2025

Watching your finance team simultaneously tell investors you're "efficiently deploying capital" while creating elaborate spreadsheets to justify why engineers can't have second monitors.

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Martin 👀 @martinoleary.bsky.social · 22/12/2025

Your CFO explaining to investors that $1M ARR means you're crushing it while simultaneously telling the team that instant coffee is now considered a luxury workplace perk.

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Martin 👀 @martinoleary.bsky.social · 19/12/2025

Product managers don't become founders because they're visionaries. They become founders because they're tired of watching their current founders make idiotic decisions while ignoring their advice.

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Martin 👀 @martinoleary.bsky.social · 18/12/2025

Is AGI Techs version of nuclear fusion? always ten years away, endlessly funded, and conveniently too complex for anyone to call the bluff.

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Martin 👀 @martinoleary.bsky.social · 17/12/2025

The fastest way to lose trust? Acting like you already have it.

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Martin 👀 @martinoleary.bsky.social · 16/12/2025

So trust is like a startup bank account—takes forever to grow, and one dumb move can wipe it out overnight.

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Martin 👀 @martinoleary.bsky.social · 15/12/2025

Bootstrapping is like hiking up a mountain with a fridge on your back, but scaling is just taking the ski lift down.

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Martin 👀 @martinoleary.bsky.social · 12/12/2025

DTC was supposed to kill retail, but the best DTC brands now realise they need retail to actually make money. The platform tax from Meta and Google makes scaling past a certain point brutal, and retailers know it.

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Martin 👀 @martinoleary.bsky.social · 11/12/2025

I'm convinced Andrej Karpathy (@karpathy) single-handedly accounts for 80% of all Grok Explainer usage on X. The rest of us: "What's for lunch?" Karpathy: "Here's how self-attention in transformers creates emergent capabilities through gradient-based optimization."

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Martin 👀 @martinoleary.bsky.social · 10/12/2025

Enterprise buyers are like dungeon masters. They set the rules, move the goalposts, and somehow always walk away with the best deal.

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Martin 👀 @martinoleary.bsky.social · 09/12/2025

The most dangerous phrase in software isn't "we should rewrite it" -> it's "wouldn't it be cool if..."

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Martin 👀 @martinoleary.bsky.social · 08/12/2025

In 2020, Vietnam threatened to shut down Facebook unless they removed political content the government didn't like. Facebook caved. Imagine that were your startup. One policy shift and your entire market is gone.

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Martin 👀 @martinoleary.bsky.social · 05/12/2025

Enterprise sales isn't a funnel. It's a maze of internal approvals, silent research, and trust-building moments that happen long before you ever get on a call.

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Martin 👀 @martinoleary.bsky.social · 04/12/2025

The best B2B startups don't chase leads. They manufacture trust at scale. Website builds credibility. Demos build relationships. Content arms champions. In-person meetings accelerate deals.

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Martin 👀 @martinoleary.bsky.social · 03/12/2025

When you're running on 4 hours of sleep and your last three meals were coffee, picking clothes becomes a Series A level decision.

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Martin 👀 @martinoleary.bsky.social · 02/12/2025

Everyone's a visionary in a bull market. In a bear market, that same strategy is suddenly "reckless gambling with investor money."

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Martin 👀 @martinoleary.bsky.social · 01/12/2025

70% of international expansions fail. Not from lack of funding but from underestimating strategy. If Uber and Airbnb can't brute-force their way into foreign markets, what makes you think your startup can?

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Martin 👀 @martinoleary.bsky.social · 28/11/2025

84% of enterprise buyers still want a human demo. Not your slick product tour. Not your Loom video. A real person who can answer "how does this not blow up our workflow?" without sweating.

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