Swimming Naked: Why Safety Nets Kill Startups

From a distance, every venture-scale problem looks whole.

Massive. Inevitable. Obvious. Clean enough to draw on a slide.

You can point to the market size. The competitor grid. The entire industry doing something the wrong way and think: this sucks — let’s build a business around it.

And you’re probably right. At times, things indeed suck.

But “this sucks” isn’t a problem statement — it’s a feeling, a placeholder for frustration.

You can’t test it. You can’t measure it. You can’t build anything meaningful on top of it.

Having chased a few 0-to-1 runs, I’ve started to notice a clear pattern that separates companies destined for wandering from those built for winning. It comes down to what I call opinionated articulation — the founder’s ability to describe their customer’s problem so specifically, so concretely, that it becomes impossible to conflate with anything else.

The Billboard Test: Why Most Startup Problems Are Worthless

To understand why this matters, imagine your problem statement plastered across a giant highway billboard. Better yet, pick one of Silicon Valley's favorite catchphrases:

"Payments are broken. Healthcare is inefficient. Hiring doesn't work."

Thousands of drivers pass it every day. Ninety percent glance up, nod vaguely:

"Hmm, yeah, that's true."

As a founder, that nod feels like validation. You can almost see the TAM slide writing itself: $500B market, 15% annual growth. Most skeptics nodding along. Your co-founder lighting up. You can almost feel the momentum.

But your "problem" is so broad it's impossible to disagree with—and equally impossible to care about.

Now imagine a different billboard. One that 95% of drivers pass without a second glance. But 5% slam the brakes, point at it, and say:

"Oh my god. That's me."

Unlike the other 95%, these 5% feel like you've been living inside their heads, watching their exact struggle unfold.

This is the Billboard Test: the moment your problem statement stops being a vague category gripe and starts being something aimed at a specific person, in a specific moment, with a specific pain.

Pass that test, and you're no longer trying to win over the whole highway. You're locking eyes with the few who will actually pull over and take the product off your hands.

Think of problem definition like adjusting the focus on a camera lens. At the start, your problem is a "space"—messy, abstract, full of possibilities. You can see that something is happening, but the details are blurry.

Founding teams are evidence-seeking machines, and the real work of an early-stage founder is to get closer to the problem. Then closer again. And again. Until the edges stop being smooth and the details stop being vague.

Zooming in until the pixels disappear and the problem isn't a broad headline anymore, but a clear and opinionated articulation of someone at an exact point in time.

Stripe Didn't Start with "Expanding the GDP of the Internet"

Most founders resist getting this specific because they think precision is a self-imposed limiting belief. They worry that by focusing on one specific pain point, they're missing the bigger opportunity. This thinking confuses market size with market access.

A $100B market you can't reach is worth exactly $0 to your startup. A $10M market where you can identify, reach, and serve the first 100 customers is worth everything.

When you say "we're building productivity tools for engineering teams," you're pointing at a massive market—millions of engineers across thousands of companies. The TAM is enormous. The opportunity feels compelling.

But how do you find those engineers? How do you reach them? What's your entry point? Which specific pain do you solve first? What's your message? Who do you call? What conference do you sponsor? What blog do you guest post on? You're paralyzed by infinity.

Now compare that to: "We help remote startup CTOs with fewer than 10 engineers ship features twice as fast by eliminating CI/CD bottlenecks."

Suddenly, everything becomes concrete. You know exactly who to find, where they hang out, their exact pain, what they'll pay for. The market is smaller, but it's reachable. You can name companies. You can list individuals. You can craft a message that makes them stop scrolling.

Most importantly: you can actually get started. And you can fail fast. When your hypothesis is this specific, evidence-finding becomes surgical. You can interview 20 startup CTOs in two weeks and definitively know if CI/CD bottlenecks are actually their biggest pain point. If they are, you build. If they're not, you pivot to what actually keeps them up at night—or you find a different target entirely.

Compare this to "productivity tools for engineering teams." How do you even test that? You could spend months talking to random engineers across random companies and still have no clear signal. The evidence gets muddled because the hypothesis was never sharp enough to begin with.

Specificity doesn't just make markets more accessible — it makes them more falsifiable. And in early-stage building, the ability to prove yourself wrong quickly is the most valuable asset you can have.

How to Win Small Before You Win Big

On the flipside, most early-stage teams resist opinionated articulation because it takes away their optionality.

When you say, "We're building for everyone who struggles with productivity," you've built yourself a giant, cozy safety net. No one can really tell you you're wrong. Almost any user comment can be interpreted as validation. You can tell yourself you're "keeping options open."

But the moment you get specific, you've burned that safety net to the ground. Now everything can be tested and anyone can call your bluff. When you make a specific claim about the world, you become vulnerable.

And that's terrifying—because you might find out your beautiful idea doesn't work.

So founders and early-stage teams lean into optionality, chasing ubiquity. It feels safer. But it's not.

Being wrong quickly is the fastest path to being right eventually. The founder who discovers their initial thesis is wrong after two weeks of customer interviews is infinitely better positioned than the founder who spends six months building for a theoretical market.

Vagueness doesn't hedge your risk. It just delays the moment you find out if you have something worth building.

Strong Opinions, Loosely Held

Here's what most founders don't realize: the key isn't to have the right opinions — it's to have opinions at all.

Category-level gripes are cheap: "Payments are slow." "Hiring is broken." These are impossible to dispute but equally impossible to act on.

They require no legwork. You don't have to interview a single customer. You don't have to watch anyone work. You can have them as shower thoughts, and many do.

An opinionated framing is different. It's costly. It's painful. And it leaves you vulnerable.

It forces you to zoom so far in that you can see the texture of the problem. And now you've committed to a reality that can be proven wrong. And that's exactly why it's valuable.

Startups aren't rewarded for dodging wrongness—they're rewarded for finding how they're wrong, fast.

You can't test a vague, agreeable complaint. You can only test a sharp, risky opinion.

And real opinions only come from someone who's been in the trenches.

The Anatomy of Problems That Actually Matter

When you start getting specific about articulation, you realize there's a recurring pattern. They tend to hit four key dimensions that turn vague complaints into hypotheses you can actually test:

1. Who: The smallest possible specific group of people experiencing the problem.

   • Not "small businesses."
   • More like: "Independent coffee shop owners in cities under 500k population."

2. When/Where: The exact context in which the problem occurs.

   • Not "while working."
   • More like: "On Monday mornings during inventory restocking."

3. What: The precise pain in observable, measurable terms.

   • Not "it's inefficient."
   • More like: "They spend three hours manually counting and reconciling inventory sheets."

4. Why It Hurts: The tangible negative consequence.

   • Not "it's annoying."
   • More like: "Causing them to over-order perishables and lose ~10% of revenue each month."

If there are multiple "whos" or multiple "whats" or multiple "whys," you're probably not there yet. But the moment you feel uncomfortable with how narrow you've gotten—that's exactly when you're getting close to something real.

Put together, the structure looks like:

[Who] experiences [What] in [When/Where], which leads to [Why It Hurts].

Example: Independent coffee shop owners in cities under 500k population spend three hours every Monday morning manually counting and reconciling inventory sheets, causing them to over-order perishables and lose ~10% of monthly revenue.

Markets Have Doors, Not Floodgates

Here's something most founders don't realize: you don't grow by starting broad and hoping to capture everything. You grow by starting narrow, winning completely, then expanding from a position of strength. Every big company started opinionated and narrow. They won a wedge and expanded from there.

Markets aren't entered through floodgates—they're entered through doors. Small, specific, well-defined doors. And those doors are opened by founders who can articulate, without hesitation, exactly who's standing on the other side and exactly what's keeping them awake at night.

When you walk into any room with opinionated articulation, you're demonstrating three things:

1. You've done the work: You're not theorizing from a whiteboard. You've talked to real people with real problems.
2. You understand the pain intimately: You can describe the problem in the customer's own words, with their specific context and constraints.
3. You have a path to revenue: You know exactly whose door to knock on first, and you have evidence they'll open it.

Deploying Empathy: The Magic of Being Seen

When you can describe someone’s problem better than they can, you win their trust - they can identify you as one of their own, and there's an immediate empathy transfer.

Most people live with their problems in a fog. They feel the symptoms, but the boundaries are fuzzy. They know they’re frustrated, but they can’t fully articulate why.

Once you articulate them, you’re giving them a structure. You’re handing them language they didn’t have before. Your framing becomes their framing, and it earns you leverage.

And here’s the real unlock: this “empathy transfer” compresses the trust timeline. Trust normally builds over repeated interactions. But when someone feels deeply seen, it happens in minutes. You skip months of relationship-building because you’ve already passed the most important test: you understand them better than they understand themselves.

Opinionated Articulation turns strangers into allies, and allies into champions.

Why Sharp Edges Beat Soft Landings

In the early days of a startup, your single most valuable asset isn't your funding, your network, or even your product — it's your ability to articulate the problem you're solving. The question isn't whether you have a good idea. The question is whether you can articulate your idea precisely enough that the right people recognize their lives in your description.

Opinionated articulation might feel like swimming without a safety net. But in early-stage building, safety nets are an illusion anyway.

Wandering feels safer. It keeps options open. It avoids the vulnerability of being specific, being wrong, being proven right or wrong by the market. But wandering is just postponing the moment when the market tells you whether you have something. And the market will tell you eventually—the only question is whether you'll have time and resources left to pivot when it does.

The real safety comes from finding your sharpest edge—and pressing it against the real world until it either cuts through or snaps. Vagueness feels safe, but it's a false safety. The market will judge you eventually—the only question is whether you'll have the time and cash left to adapt.