From Product Management to AI Startup with Gavin McNamara
On the Predictable Revenue Podcast, Collin Stewart sat down with Gavin McNamara to unpack his product-market fit journey.
It didn’t start with a clear idea or a validated market. It started with messy consulting work, a personal problem, and a series of small signals that only made sense in hindsight. That’s the reality most founders don’t hear.
Product-market fit isn’t a single moment where everything clicks. It’s something you work toward by following real problems, real customers, and narrowing in on what actually works.
This is what that process actually looks like.
Don’t Wait for Certainty
Most founders think there’s a moment where everything lines up: a clear idea, a validated market, an obvious path forward. That moment doesn’t come.
Gavin didn’t quit because the business was proven. He quit because he saw enough signal. A few people were willing to pay. The problem felt real. That was it.
He still had a safety net in his head: If this fails, I can always go back.
Then reality hit: Three months, no revenue, a wife, and a kid on the way.
That’s the part no one talks about.
The gap between starting and working is longer and quieter than you expect.
You don’t validate your way into certainty and then leap. You leap when there’s just enough signal to believe, and figure the rest out on the way down.
Start Ugly
There was no polished product in the early days, just a series of small, messy projects.
Gavin helped people with whatever AI problems they had. Voice cloning, websites, and new tools, if someone asked, he said yes. It wasn’t scalable or structured, but it didn’t need to be.
Those projects created direct exposure to real problems. Instead of guessing what the market wanted, he saw it up close, how people described their needs, what they’d pay for, and where AI actually delivered value.
This is the phase most founders try to skip.
They jump straight to building a product, assuming they already understand the problem. In reality, this kind of unscalable work is what sharpens that understanding. It’s how you separate interesting ideas from real demand.
Consulting was just the bridge. Before you can build something scalable, you need to know what’s actually worth scaling.
Product-Market Fit Doesn’t Start With a Product
The breakthrough came from a personal moment.
Gavin was at his parents’ house, looking through a garage full of old items, things his dad insisted were valuable, but that looked like clutter. The question was simple: what is this stuff actually worth?
That became the foundation for one of the first real products under Why Not Us. He built a simple app that could take a photo of an item and estimate its value.
No big launch. No defined experience. Just something functional enough to test.
The first users weren’t the target market, they were friends and people who would actually try it and give honest feedback.
That’s where most founders get it wrong. They start with the product, then go looking for a problem. In practice, it works the other way around.
Product-market fit starts with a sharp, specific problem, something concrete enough that, when you show a rough solution, people immediately understand why it matters.
The PMF Moment
Up to a certain point, the product was getting the kind of response you’d expect early on: people were interested, they gave feedback, and some were willing to try it. It looked like progress, but it still required effort to explain the value. Then something changed.
A reseller tested the app on a rare item, something specific and difficult to price correctly. Within seconds, the app identified the exact product, recognized its rarity, and returned an accurate valuation.
The response wasn’t measured or analytical. It was immediate: “We need to talk right now.”
That moment is different from everything that comes before it.
There’s no convincing, no long explanation, no back-and-forth. The value is obvious, and the urgency comes from the customer, not the founder.
This is what product-market fit actually feels like in practice. It’s not gradual validation or polite interest. It’s a shift in behavior when people stop evaluating and start using the product as quickly as possible.
Instead of pushing the product onto customers, you feel them pulling it toward themselves.
Your First Customers Won’t Be Scalable (And That’s Fine)
The first customers didn’t come from a repeatable channel or a formal go-to-market strategy.
They came from people Gavin already knew, then from people those people knew. A friend shares it with a friend, who happens to run a niche business, who then sees immediate value.
That’s how the reseller connection happened, and with it, an entire vertical started to open up.
From the outside, this can look messy or even misleading. There’s no clear funnel, no predictable acquisition engine, no obvious way to “scale” what’s working. But that’s the point.
Early traction is almost always uneven.
It comes in bursts, through introductions, through moments you couldn’t have planned. One conversation leads nowhere, another unlocks a completely new use case.
Founders often dismiss this kind of traction because it doesn’t feel repeatable. They’re looking for something systematic too early.
In reality, this is how you find your way into a real market. Those early, non-scalable wins reveal where the product actually fits and who cares enough to use it. Only after that do you earn the right to think about scale.
Product-Market Fit Is a Multiplier
At a certain point, the question stops being “does this work?” and becomes “where does this work best?” The underlying product didn’t fundamentally change. What changed was who it was for.
Positioned broadly, it generated interest but inconsistent traction. Positioned narrowly, first with sneaker resellers, it became immediately valuable. The same core functionality, but now applied to a context where accuracy and speed directly impacted money.
This is where product-market fit starts to strengthen.
As Collin puts it, “product-market fit… is a multiplier of go-to-market efforts.”
When the fit is weak, even strong sales and marketing struggle to convert. When the fit is strong, even simple outreach starts working.
This pattern shows up across markets.
A generic offering spreads thin. A focused one resonates. The more specific the use case, the easier it is for customers to recognize the value without needing it explained.
Better targeting doesn’t just improve conversion, it changes how the product is perceived. And in many cases, that matters more than the product itself.
Focus First. Expansion Comes Later.
Sneaker resellers are an obvious fit, but so are everyday consumers. And then there’s insurance, where documenting and valuing items could become far more than a convenience.
The same product can serve multiple markets. This is where most founders make a mistake. They see optionality and try to pursue it all at once.
The result is predictable:
Diluted messaging, unclear positioning, and weaker traction across the board. The faster path to product-market fit is the opposite.
- Narrow the focus. Pick the use case where the value is most immediate and undeniable, and go deep there.
In this case, that meant leaning into a specific niche first, even while knowing the product could expand far beyond it.
What’s interesting is that expansion doesn’t come from brainstorming new ideas. It comes from following what the initial use case reveals.
The sneaker resale use case was clear from the start. But in solving for it, something else emerged, an inventory system. Every scanned item became part of a structured record: images, metadata, valuations. That naturally extended into a much larger opportunity around insurance and asset tracking.
The bigger market wasn’t planned. It was uncovered.
This is how product-market fit evolves. Not as a single moment, but as a progression, from a narrow, high-signal use case to broader applications that build on top of it.
Which is why it’s rarely a binary state. You don’t simply “have it” or “not have it.” The strength of the fit increases as you refine the market, the use case, and the positioning.
If you’re unsure whether you’ve reached it, you probably haven’t yet.
Strong product-market fit is hard to miss.
It shows up in how quickly people understand the value, how easily they adopt it, and how little convincing is required. And getting there doesn’t come from chasing every opportunity. It comes from focusing long enough for one to click fully.
Conclusion
Most founders are looking for confirmation. Product-market fit doesn’t give you that. It gives you pressure.
- Pressure to focus.
- Pressure to choose a market.
- Pressure to follow what’s working, even if it’s not what you planned.
The ones who get there aren’t the ones with the best ideas. They’re the ones who pay attention to that pressure and keep narrowing until the value is undeniable. That’s when it clicks.
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