Why Measure Anything If You're Crushing It?

The best time to build your measurement process is before you need it.

A few months ago, I met a founder who was riding high. They’d just raised a Series A, they were hitting their targets, and growth was solid. They had no reason to take a meeting with me… except that I’d sent them a quirky outbound gift that piqued their curiosity.

They got on the call and asked me, point-blank:

“Why would I need Equals? What do I need to measure? We’re doing great.”

It’s a fair question. When things are going well, it’s easy to deprioritize rigor. The business feels like it’s working. But that’s exactly when you should be investing in measurement. Not because things are broken. But because one day, they will be. And when that day comes, you’re going to wish you.

That conversation lasted an hour. I didn’t convince them that day. But a few months later, they came back. They’d started to feel the friction. Now they’re one of our most vocal users. Because they saw what I was trying to explain.

Here’s the crux of what I said to them. Three main points.

First, you won’t always be hitting plan.

Every startup runs into headwinds. Eventually you’ll miss a target. And when that happens, you’re going to want to understand why. Was it top-of-funnel? Sales execution? Onboarding? A change to the funnel? Pricing? Expansion? Churn? Without some kind of measurement discipline already in place, you’ll be stuck guessing. Worse—you’ll be stuck reacting, instead of diagnosing. Building that feedback loop early gives you a baseline for what’s working and what’s not, so when things shift, you’re ready.

Second, you’re almost certainly leaving growth on the table.

Just because the numbers are up doesn’t mean they’re optimized. Measuring your business isn’t just about catching problems—it’s about finding upside. Are certain channels more efficient than others? Are there segments with higher LTV or shorter sales cycles? Is churn hiding in a specific cohort? You don’t get those answers by gut. You get them by looking under the hood. And once you do, you start operating with intention—not momentum.

Third, you’re setting the tone for how your team operates.

Even if you’re small, the habits you build now will shape your culture later. If all your team sees is high-level revenue goals, they’ll optimize for that. But eventually you’ll need more granularity: leads, pipeline, conversion, activation, engagement. And if your team isn’t used to tracking and owning those metrics, you’ll struggle to scale accountability. Great teams don’t just celebrate results. They understand what drives them. And that starts with measurement.

The biggest mistake you can make is waiting until something breaks to care about how it works.

If you're crushing it today, congrats. That’s the best time to start instrumenting the machine. Not because you’re trying to fix it. But because it’s running well, and you want to keep it that way.

Don’t wait for the numbers to stop working to start understanding them.

Build the habit now. Build the system now.

So when things get hard, and they will, you’re not scrambling. You’re operating.

Next time you encounter a founder like that in the wild, send them this post. 🙂