The real reason startups fail

In Greek mythology, Sisyphus was condemned to a peculiar kind of hell: to push a massive boulder up a hill, only to watch it roll back down every time he neared the top, repeating this task for eternity.

On the surface, it’s a story of futility. But read differently, it’s a story of grit. Sisyphus never stops pushing. For many founders, startup life can feel just as Sisyphean. You pour your energy into launches that fail, hires that leave, and channels that flop. Every time you're near the top, traction, funding, or PMF slips away. And yet, like Sisyphus, you push again. Not because it’s easy, or rational, or guaranteed to work. But because belief, persistence, and movement are sometimes the only tools you have.

This essay is about those invisible forces, the thousand tiny cuts that wear you down, and the small, hard-won victories that keep you going. Enjoy!

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Startups do not die because of a lack of resources but from death by a thousand tiny cuts.

When you are building a startup, you are likely running hundreds of experiments across products, target audiences, markets, messaging, business models, and hiring all at once.

The vast majority of these experiments fail.

I literally visualize tiny injuries, individually harmless but collectively fatal. Anyone who's experienced startup life knows it's full of big and small setbacks, frustrations, and disappointments.

It’s an emotional roller coaster.

A small product launch that gets no traction, a channel that doesn't convert, a promising hire that leaves after a month, each one individually minor, but collectively, they feel exhausting.

Every tiny failure becomes a nail in the coffin.

Founders like to think the enemy is running out of money (and yes, many startups do die because of that), but often, money runs out because the team loses momentum and belief.

The operational problems are just symptoms.

The real damage is psychological.

These setbacks slowly erode your resolve. Morale dips. The team loses conviction and direction.

It's not just the financial or resource consequences of failed experiments that matter; it's the psychological toll.

It's the slow draining of emotional energy, enthusiasm, and, ultimately, belief you can reach product-market fit (PMF).

This psychological layer is what makes startups fragile.

Contrary to what many think, the damage isn’t always visible on a spreadsheet, it’s in the psyche. And over time, that leads to a loss of clarity, vision, and decisiveness.

The antidote to this downward spiral is to win big every once in a while.

You do not need to get everything right.

But every once in a while, you need to win in a meaningful way.

A spike in user growth. A key customer signing. Increased engagement. Reduced churn. You name it. Each of these, even if temporary or intermittent, can serve as a powerful reminder that "something here works." Small wins provide validation. They restore a sense of purpose, rekindling enthusiasm and commitment.

Most importantly, each tiny win serves as a validation that your judgment is right.

This means that, on a long horizon, you can navigate the idea maze.

Over time, these wins compound. They bring you closer to PMF. When you reach it, you’ll notice a shift. Even when parts of the experience are broken, minor flaws become tolerable because user value dominates.

Your goal is to reach that stage.

I've met founders at their third, fourth, or even sixth pivots. It's evident how drained they are. The thousand cuts have taken their toll.

It’s very hard to recover from such a state.

That’s why you must do everything possible to engineer small wins. Some examples:

Concentrate your efforts on a few channels with strong conviction. Running too many small experiments simultaneously might fragment focus. Narrowing attention allows the team to execute better, increasing the likelihood of meaningful results.

Focus on one persona and work intimately closer with them to uncover what they need, then be obsessed with building a great product. Deeply understanding a narrow target audience allows for clearer messaging, more relevant product features, and stronger feedback loops.

Borrow what works. Don’t waste energy reinventing the wheel. Adapting proven approaches, especially early, helps conserve precious attention and energy. Borrowing successful practices from other companies isn't cheating, it’s strategic and smart. It frees resources to focus on unique problems that no one has solved yet.

And above all, develop product intuition. These days, people call it taste. In turn, many often ask, how do you build intuition? It’s a hard question, but here’s my best attempt at answering it: Intuition comes from deep immersion in your product area, studying other great products, rigorous user interactions, and relentless attempts against the target. It's not just luck or talent; it's systematically built. Intuition is experience distilled into subconscious judgment.

The more wins you accumulate, the better your morale. The better your morale, the better your execution.

Which leads to more wins.

A virtuous cycle, essentially.

Teams that feel validated and see tangible success tend to invest greater effort and produce better results. Morale boosts performance.

Before you know it, you have reached PMF.

Suddenly, you're the talk of the town. Talent finds you on their own. Potential clients are knocking on the door. The media wants to write about you. VCs start reaching out. The work is still hard, but it feels lighter. You’re not fighting upstream anymore. You’re building something real.

You've set in motion a momentum that paves the way for building a great business.

For some reason, the boulder doesn’t roll back.

Sometimes, it tips just enough over the edge, and momentum takes over.

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