After years of running my own startups and mentoring others—across industries, stages, and continents—there’s one repeated failure I see that cuts deep into the root of startup success: designing a product in a vacuum.

Too often, the product vision is crafted behind closed doors by well-meaning founders with deep industry experience. And it’s exactly that confidence that becomes the problem. The founder thinks they know what their customer wants. After all, they’ve worked in the industry for 10, 15, 20 years. I know—I’ve been there myself. I’ve made this rather expensive mistake, and it was a humbling lesson. Founders like us have seen what’s broken, lived the pain, and so we build a product to solve what we assume our customers need.

But here’s the thing: experience is not a substitute for customer conversation. And assumption is not validation.

This plays out again and again, especially in enterprise B2B settings. A founder assumes that because their solution works for one enterprise, it’ll work for all of them. But enterprise customers are rarely homogeneous. Each has unique internal processes, decision-making quirks, stakeholder dynamics, compliance constraints, and success metrics. What seems like a “one-size-fits-all” product is often a friction-filled misfit. And in enterprise sales, even a sliver of friction is enough to kill the deal entirely.

Been There, Done That (And Paid the Price)

Earlier in my career, I lived in the Philippines for five years, serving as Southeast Asia Regional Director for a top-five global engineering consultancy. It’s also where I launched my first two startups. My love for the Philippines runs deep. So when I had an idea that I believed could improve the lives of artisanal fisherfolk by helping them become bankable, I threw myself into it completely. This was a chance to do something truly meaningful in a country that had given me so much.

The idea was simple, at least on paper: use fish catch landing data to assess the creditworthiness of artisanal fisherfolk. Banks could then use this information to offer fair financing terms based on historical catch patterns. For many of these communities, access to credit was virtually nonexistent. Without bank accounts or formal financial histories, fisherfolk were forced to borrow from middlemen at predatory rates—often with their homes, land, or boats as collateral. Add to this the inherent risks of seasonal fishing and the Philippines’ volatile climate—typhoons, monsoons, even volcanic eruptions—and the economic vulnerability was clear.

Despite these challenges, I’ve always said the Philippines is one of the happiest countries I’ve lived in. Not Finland—despite its annual title as the world’s happiest nation (and, ironically, one of the highest suicide rates). And yes, I lived in Finland too, for 4.5 years. But I digress.

The economic imbalance in the Philippines is stark: the rich get richer, the poor remain trapped. I wanted to make a dent in that cycle.

I pitched the idea to the World Wildlife Fund and Union Bank of the Philippines: a blockchain-enabled app that would track fish catch data, assess creditworthiness, and facilitate access to financing. They loved it. With WWF managing field operations and one of the country’s top banks ready to lend, I felt we had everything in place. All we had to do was build the app. “Build it and they will come,” I thought.

Turns out, that line works in movies—not in the real world.

Our service design process was shallow. We held one initial meeting with the fisherfolk to understand their needs and capabilities, then rushed ahead with development. It wasn’t from lack of care—time and budget were tight, and we were eager to deliver on the momentum we had with the bank and WWF.

But when we launched, reality hit hard.

IT literacy among fisherfolk was far lower than we had anticipated. Many didn’t own smartphones. Those who did often didn’t have Android devices, which our app depended on. We had assumed that even in poorer communities, phones would be common. They weren’t. WWF had to supply devices. In most households, it was the children—not the fisherfolk—who ended up logging the data.

We had built something that worked for the bank, but not with the fisherfolk. We had designed for only half of the customer base. We didn’t have product-market fit.

I was devastated. I had failed to deliver on my vision—and more importantly, I hadn’t managed to help the people I set out to support. That still weighs on me. I think about that project often. It continues to shape the way I lead Silta and how I coach the founders I work with today. When I talk about product-market fit, I don’t just stress its importance—I impress it, because I’ve lived the consequences of getting it wrong.

Start With the Problem, Not the Product

If I could offer one golden rule to early-stage founders, it would be this: do not build anything until you’ve had a dozen—preferably more—meaningful conversations with potential customers.

And I don’t mean surface-level chats. I mean real, open-ended, curiosity-driven interviews. Ask about their day-to-day pain points. Where are they losing time? Money? Patience? Don’t pitch. Just listen.

Better still, invite them into the design process. Let them sketch solutions with you. Show them early concepts and wireframes. Ask what resonates and what doesn’t. If you can co-create your MVP with a few target customers, you greatly increase the odds that what you’re building will matter.

The goal isn’t to build something usable. It’s to build something indispensable.

Your MVP Isn’t the End—It’s the Beginning

Shipping the MVP is not a finish line. It’s the starting gun. The most successful founders stay obsessively close to their users post-launch. They don’t just push features. They pull insights. That means running customer satisfaction surveys. Hosting feedback sessions. Picking up the phone.

This isn’t about polishing a UI. It’s about uncovering whether you’ve built something people truly need—and where the gaps still lie. What do customers love? What do they ignore? What frustrates them? What’s missing?

Every data point is a breadcrumb leading you toward greater product value. And more value means more sales.

Price Based on the Problem You Solve

Here’s another often-overlooked step: when talking to customers about pain points, ask how much those problems cost.

Whether it’s lost revenue, wasted staff time, compliance risks, or customer churn, understanding the financial cost of the problem gives you a powerful anchor for pricing. If you can save a company $500,000 annually, pricing your product at $50,000 is not just justifiable—it’s compelling.

This is the foundation of value-based pricing. Don’t set your price based on development costs or competitor benchmarks. Set it based on the tangible value you’re delivering.

Don’t Just Know Better—Remember to Act on It

Most of the time, the challenge for founders isn’t not knowing what to do—it’s forgetting to do it. When you’re moving fast, spinning plates, and battling fires, even the fundamentals can slip.

That’s where coaches and mentors come in. It’s not always about new ideas. Sometimes, it’s about old truths—remembered at the right moment. A great coach keeps you grounded, honest, and aligned with what really matters.

Final Thoughts

Product-market fit isn’t something you stumble into. It’s something you earn. Through empathy. Through iteration. Through a relentless focus on the customer. So whether you’re designing for a global enterprise or a rural fishing village, pause. Ask questions. Listen—really listen. Build with your users, not just for them. And if you need someone to help you stay on track, get a coach. Even the best founders need one.

If you’re a founder navigating early-stage growth, product-market fit, or enterprise sales—and want an experienced guide by your side—reach out to me at bensheppardxyz@gmail.com.