Startup Corner #12: Understanding Customers
How great startups get closer to what people actually need
Hey friends,
Lately I’ve been thinking about something that seems basic — almost obvious — but still trips up so many startups:
Do we really understand our customer?
It’s one of those things that’s easy to say — “of course we do, we’ve done interviews, we’ve got personas, we have feedback.”
But the deeper I look at companies that actually break through, the more I realize this is where the gap usually is.
Not in vision. Not in execution.
In understanding.
And not just listening — really understanding.
So I wanted to jot down a few things I’ve been observing and thinking through. About what it really means to understand the people you’re building for — and what it looks like when startups get it right.
Customers usually don’t say what they mean — and that’s okay
One of the first traps I see (and honestly, fall into myself sometimes) is taking people’s words at face value.
You ask someone if they’d use your product.
They say yes.
You get excited.
You build.
And then… nothing.
The truth is, most people are nice. They want to be encouraging. They also don’t always know what they want — especially if you’re working on something new.
The best founders I’ve seen don’t just listen to what customers say — they watch what they do. And they pay attention to the stuff people mention casually, or emotionally, or offhand — that’s usually where the gold is.
Real insight lives in behavior
One thing I love about the early Superhuman story is how they measured product-market fit. Instead of asking “Do you like this?” they asked:
“How disappointed would you be if you could no longer use this?”
They weren’t chasing compliments — they were looking for signs of dependence.
That shift in thinking — from asking people what they think, to observing how they behave — makes all the difference.
If someone tries your product, brings it up unprompted, asks questions, or complains when it’s buggy — that’s a real signal. If they say “this is cool” and disappear, that’s just… noise.
You’re not the customer — even if you’ve felt the same pain
You’ve felt the pain. You get it. You’ve been there.
But the second you become a builder, you start seeing the world differently — and solving problems from a different lens.
The way you think about tools, decisions, friction — it changes. You have more context, more control, more optimism.
Your customer might not. They might be stuck with outdated systems, annoying approval layers, and five tabs open just to do a simple task.
Stripe figured this out early. They didn’t build for every developer. They built for a specific kind — fast-moving, product-minded engineers who wanted to move quickly and hated red tape. That clarity shaped everything they did.
Good startups listen once. Great ones listen constantly.
This is something I’m noticing more and more: the best teams don’t treat customer understanding like a box to check.
They don’t say “we talked to 20 users, we’re good now.” They build it into the rhythm of how they operate.
Some do it through support conversations. Some join onboarding calls. Some just check in casually with power users every month.
But the common thread? They stay close.
Notion is a great example — their community isn’t just a nice-to-have, it’s a constant feedback engine. Same with Figma. These companies don’t just react to feedback — they live in it.
Understanding your customer isn’t about what they want — it’s about how they live
This might be the most important thing I’ve learned just from watching others do this well.
If you really want to understand your customer, you need to understand:
What their day actually looks like
What they’re trying to do (not just with your product, but in general)
What’s annoying them quietly that they’ve stopped even noticing
What language they use to describe their own world
You can’t always get that from a 30-minute call. Sometimes it takes shadowing them. Or watching recordings. Or just hanging around long enough to notice the little stuff they don’t even mention.
That’s where great products come from.
Not big eureka moments. Just small, repeated observations that finally click.
Final thought: The fewer guesses you have to make, the better your odds
There’s always going to be uncertainty.
But when you really understand your customer — not just in theory, but deeply — everything gets a little easier.
You start building things that actually get used.
Your copy sounds like something they’d say.
Pricing feels obvious.
Growth doesn’t feel like pushing a boulder uphill.
You’re not guessing anymore (less bets?).
You’re just serving.
That’s the kind of understanding I want to get to more consistently — and the kind of thinking I think we all get better at by practicing.
Talk soon,
— RB
Startup Corner