When I was at Intercom, I’d spend days—sometimes weeks—building a forecast.
Dozens of tabs.
Churn curves.
Pipeline assumptions.
Detailed hiring plans.
Everything tied out to our operating model and cash runway.
Then Eoghan, our CEO, would pull up a simple spreadsheet. One row. Maybe two.
He’d drag out a growth curve and say something like:
“We’re here. And I think we’ll grow like this.”
It was often just an extrapolation of our current trajectory. Or worse—an exponential curve with no basis in reality.
And I’d roll my eyes.
Because come on—where’s the funnel logic? The seasonality? The CAC assumptions?
But here’s the thing:
He was often right.
Two Types of Math
There’s finance math—and then there’s CEO math.
Finance math is grounded.
It’s skeptical.
It’s built from historicals. It looks for risk. It pressure-tests assumptions. It’s cautious because it has to be.
CEO math is intuitive.
It’s directional.
It doesn’t worry if CAC doesn’t quite make sense yet—because it believes it will. It sketches a world that doesn’t exist yet, but might if we push hard enough.
Finance math says, “Here’s what we can probably do.”
CEO math says, “Here’s what we’re going to do.”
Why CEO Math Sometimes Wins
As frustrating as it was in the moment, I’ve come to appreciate that there’s a kind of magic in CEO math.
It’s not logical. But it’s not dumb either.
CEO math bakes in ambition. It refuses to accept current constraints.
And that refusal creates a sense of inevitability that changes how the team operates.
People hire faster. Launch faster. Sell harder.
The company bends itself toward the forecast.
Finance math protects the downside.
CEO math creates the upside.
It’s a bet on belief over logic.
And sometimes, belief wins.
When It Goes Off the Rails
Of course, CEO math isn’t always right.
It can lead to overhiring.
To blowing through cash.
To goals so unrealistic they demotivate rather than inspire.
CEO math becomes dangerous when it disconnects from reality—when it’s immune to feedback or uninterested in learning.
That’s where most companies get into trouble. Not because the vision was too big—but because nobody was willing (or able) to challenge it.
The Role of the First Operator
As the first operator, your job isn’t to shut down the CEO’s curve.
It’s to ask the hard questions. Add the realism. Bring the grounding.
But also: to stay open.
Open to the idea that the crazy forecast might actually work.
That the team might rise to meet the ambition.
That the business might break in a good way—and become something better.
The tension between the two forecasts—that’s where the magic lives.
The Forecast Isn’t the Point
Over time, I’ve realized the point of a forecast isn’t to be right.
It’s to set a tempo.
To give the team a target that creates urgency.
To force clarity on what needs to happen to make the next chapter possible.
Sometimes that target comes from a 20-tab model.
And sometimes it comes from a CEO dragging a line upward with nothing but belief behind it.
Both are useful.
And if you’re doing it right, the First Operator learns to live in the space between the two.
As a former fractional CFO who made the transition to CEO, this piece really hits.
I’ve fallen victim to this in both directions: first, by getting frustrated with CEOs who wanted to manifest 4x YoY growth out of thin air. And second, by bringing a purely CFO mindset to the forecast I put in front of my team. I will definitely be thinking about this piece as I put together our company’s plan for 2026.