A founder I work with walked into a law firm to demo his product to two paralegals.
He had built 20 features. He’s a serious engineer, ex big tech, and he’d spent more than a year on the core engine. It’s genuinely hard to replicate.
He showed them two features. They lit up. They started talking over each other about another tool they pay for and barely use, and the one that never worked.
The other 18 features never came up.
Think about what that cost. Nights and weekends, most of it spent on things nobody in that room needed. And he only found that out because he finally sat in front of a buyer and watched.
If you’re technical, you probably know this feeling. You don’t know what the customer wants yet, so you build. Building is the thing you’re good at, and building feels like progress. You ship something, show a few people, get a polite “interesting,” and go build the next version. Then the next one.
Every cycle feels productive. Most of them are a way to avoid the conversation that would end the cycle.
I don’t mean that as a knock. I mean it as a diagnosis.
Knowing better doesn’t fix it
Today I spoke with another engineer. Two well-known tech companies on her resume. Her first startup didn’t take off, and she told me that’s what taught her how much go-to-market matters.
So for her second company, she picked the go-to-market space on purpose. In her words, it was “a forcing function for me to learn.”
She decided to learn selling by building a product.
She started with a tool that turns blog posts into social content. As AI got better, the scope grew. Now it does everything end to end. She has thousands of users and about $1,000 a month in revenue.
Thousands of people will use something free. Only a handful have a problem painful enough to pay for it.
I listened to her pitch and played it back to her. Everything she’d told me came down to “you’ll get more, you’ll distribute more.” Then I asked her what I ask every founder: what’s the pain you’re solving that someone has to act on?
She didn’t have an answer yet. And she’s smart, self-aware, and has already been through one startup that failed for exactly this reason.
That’s what interested me. Someone who has paid for this mistake once was still reaching for the build.
What the build is protecting you from
She said something else that stuck with me: “I’m good at connecting with people, but I’m not good at selling.”
The first founder says nearly the same thing. He’s warm and people like him. But asking for the meeting, stating the price, and sitting in the silence afterward are the hard parts for him.
That’s the real reason technical founders build first. Code never tells you no. A buyer can. Every new feature puts off the moment someone tells you whether this matters to them.
Meanwhile the market keeps moving. While the first founder kept refining his engine, a well-funded team launched something that overlaps it. A prospect he’d been talking to hired someone to build their own version. Being technically better didn’t save him time. It cost him time.
Story first, then code
Here’s the order I push founders toward, and it’s the opposite of what feels natural.
First, write the sentence a buyer would say yes to. A specific person, a specific cost they’re living with, a specific result in a specific timeframe. “Live in a week” is a story. “AI-powered, end to end” is a feature list.
Then put that sentence in front of buyers before you write more code. If they lean in, they’ll tell you what to build. If they don’t, you just saved yourself the next six months.
The founder selling to law firms now pitches a three-week pilot on one slice of a customer’s data at a fixed price. Small, specific, and easy to say yes to. It isn’t closed yet. But for the first time, the conversation is about the buyer’s problem and not his feature list.
I’ve been in sales since I was the founding AE at a startup that went from zero to $10M. The founders who win aren’t the ones with the best product on day one. They’re the ones who figure out what problem they solve and how to say it before they’ve built too much.
Your product isn’t your strategy. Your story is. The code follows.
If you’re a technical founder caught in that loop, building, showing, iterating, and still not sure what you’re actually solving, that’s the work I do. I help founders lock down their story and test it with real buyers before they spend another quarter building. Book a conversation at daverubinstein.com.