From Fit to First Customers: What Product-Market Fit Really Looks Like in the Wild

Product-market fit is one of the most talked-about milestones in startup life and one of the least agreed-upon. Is it a feeling? A metric? A moment when growth suddenly feels easier?

At Startup Boston Week, a candid panel of founders, operators, and investors pulled back the curtain on what it actually looks like to move from early traction to first real customers and why the journey is messier than most pitch decks suggest.

Moderated by Shawn Harris, CEO and co-founder of CoWorked, the session brought together voices who’ve seen product-market fit from every angle: Steve Walsh of Hands-On Angel, growth expert and author Anuj Adhiya, and Jordyn Bonds, co-founder and CTO of consumer voice-messaging startup Hollerhype. 

The full event video is embedded below if you’d like to watch the conversation start-to-finish, or keep reading for an overview.

Together, they challenged tidy definitions and replaced them with something more honest and more useful for founders in the room.

Product-Market Fit Isn’t a Feeling, But It Doesn’t Ignore Reality Either

Founders often hear that product-market fit is when the market “pulls” your product out of you. Bonds doesn’t disagree, but she warns against relying on vibes alone. In her experience, real product-market fit shows up when demand outpaces your ability to serve it.

“You go from begging people to try your product to deciding who doesn’t get access,” she explained. “That’s a very weird shift and a very real one.”

Adhiya offered another lens: when your absence hurts more than your presence helps. He shared a moment from his time leading a growth community, when a brief outage sparked immediate backlash from users. That reaction, he argued, was the clearest signal possible, people weren’t just using the product, they depended on it.

Walsh brought the discussion back to customers themselves. Rather than asking founders how product-market fit feels, he pointed to a simple but uncomfortable test: ask customers whether they’d be genuinely disappointed if your product disappeared. If 40–50% say yes, you may be onto something. If not, you have more work to do.

Retention Tells the Truth Faster Than Growth

Across the panel, one theme kept resurfacing: retention matters more than early excitement. Anyone can get users to try something once. Getting them to come back again and again, is what separates curiosity from necessity.

Adhiya emphasized “stable retention,” especially repeated use across consistent time periods. A user who shows up four times isn’t experimenting anymore, they’re forming a habit. That’s where real learning begins.

And early on, founders should resist the urge to accept every interested customer. “If you’re doing all the selling,” Adhiya warned, “you’re probably talking to the wrong people.” The right customers chase you, follow up, and push to get access faster.

Why Product-Market Fit Changes Everything

While venture-scale outcomes dominated part of the conversation, the panel was quick to note that product-market fit isn’t just for VC-backed companies. Even for bootstrapped or lifestyle businesses, it’s the foundation for efficiency.

When you have fit, customer acquisition gets cheaper, retention improves, and overhead drops. Your product becomes easier to sell because customers already understand its value and tell others for you. Without fit, scaling only magnifies inefficiencies.

Still, the panel cautioned that product-market fit isn’t permanent. Markets shift. Customer expectations evolve. What worked yesterday can quietly stop working tomorrow.

Maintaining fit requires staying close to customers long after the early discovery phase ends, a challenge that only gets harder as companies grow.

If You Have Six Months of Runway, Start Here

When asked what founders should do now - especially those with limited time and capital - the advice was refreshingly direct.

Start with hypotheses. Who exactly has the problem you’re solving? What is the problem, in concrete terms? If you can’t answer those questions, no amount of feature development will save you.

Then, pressure-test monetization early. Not later. Not “once we grow.” If no one is willing to pay even a small amount, that’s data you can’t afford to ignore. As Walsh put it, free users are easy. Paying customers are the real signal.

Design partners can help (especially in B2B) but they come with risk. One partner can turn into a custom services engagement if founders aren’t careful. The goal isn’t building something perfect for one customer; it’s finding repeatability across many.

Above all, the panel encouraged founders to move fast but learn faster. “The biggest reason startups fail,” Adhiya said, “isn’t lack of ideas or money. It’s learning too slowly.”

The Takeaway: Fall in Love With the Problem, Not the Solution

As the session wrapped, Harris offered a reminder that resonated with the room: product-market fit starts with obsession, not with features, but with the problem itself. Founders need the humility to kill ideas they love and the discipline to keep listening even when growth feels strong.

Product-market fit isn’t a finish line. It’s a fragile, moving target and the companies that survive are the ones willing to keep earning it.

The full event video is embedded above (or you can watch it directly on YouTube) to catch the complete Q&A and founder stories shared from the stage.