Thoughts on Retention

Over the last few months, I have spoken with 5+ founders from YC-backed companies and other early incubators. Every single one of them pointed to the same issue as their biggest problem: retention.

That alone should say something.

One conversation in particular stuck with me. A founder told me that retention was the company’s biggest challenge, and in the same breath mentioned that he was hiring a Founding GTM lead. Not a product hire. Not an engineer. A marketing person.

At first, it struck me as odd. Why would you focus on bringing more people in when you already know they are leaving? Why spend time and money filling a leaky bucket instead of fixing the holes? More users do not solve a broken experience. They just help you discover the problem faster.

But after sitting with it, I realized this mindset is not rare. It is incentivized.

Early-stage founders are not irrational. They are responding to what the market rewards. When you are raising a seed round, the core question investors are trying to answer is simple: will anyone actually pay for this? Not will they stay forever. Not will this become indispensable. Just is there demand at all.

Because of that, the numbers that get the most attention are growth metrics. User growth. Pipeline growth. Logo count. Charts that move up and to the right. These numbers look good in a deck and create the feeling of momentum, even if that momentum is hollow.

Retention does not photograph well. It is slow. It is boring. And most importantly, it is honest. Retention tells you whether your product actually earned a place in someone’s life.

Marketing a weak product does not fix it. It makes it worse. When you over-market something that under-delivers, you burn trust at scale. You get one strong first impression. After that, winning someone back is dramatically harder. A second impression rarely comes with the same optimism as the first.

This is why churn is often not a mystery. Churn is the natural outcome of over-marketing or under-producing. When expectations are set higher than the experience can meet, users leave. Not because they misunderstood the product, but because the product did not live up to the promise.

And once that happens, no amount of clever GTM can save you. Marketing is leverage. If the product is good, marketing amplifies that goodness. If the product is bad or unfinished, marketing just helps more people discover it faster and walk away disappointed.

Early growth can hide this problem for a surprisingly long time. You can brute-force acquisition. You can convince yourself that retention will improve later, once features ship or pricing changes or users “understand it better.” But eventually, the math catches up.

The best founders I have seen treat retention as a design constraint, not a metric. They think deeply about whether the product creates repeatable value. They care less about how many people sign up and more about how many would be genuinely annoyed if the product disappeared tomorrow.

Growth gets you attention. Retention earns you trust. And trust is what compounds.

If you know users are leaving, the answer is rarely to turn up the volume. Fix the product. Fix the experience. Fix the promise. Everything else can wait.