The Best Founders Don’t Move Forward. They Work Backward.
Most founders put one foot in front of the other: the next sale, the next feature, the next hire, hoping it all adds up.
The best operators do something different. They work backward.
At any given time, a startup is working toward one of three priorities: the next fundraise, profitability, or an exit. That destination shapes every move a founder makes. Most don’t know which one they’re chasing.
But picking a destination isn’t enough. The move most founders miss is this: once you know where you’re going, you have to gather intel. Talk to people. Look up primary sources. Not guess. Research.
The mechanics of working backward are the same no matter the destination. Let’s use fundraising.
Working Hard (But Blindly)
We’ll call her Gabby. She led a team of 12 and raised just over $5M in her seed round for her B2B Fintech business late last year. The team was working relentlessly. And they were completely confused.
Not openly dysfunctional, just not fully aligned. If you examined what each person was working on, you’d leave wondering: What is actually most important here? Why are they taking these actions?
Because the company was fully distributed, with every employee in a different city, the ambient communication that normally papers over misalignment just wasn’t there.
When we interviewed the team, four themes emerged:
- They believed in the long-term vision.
- They didn’t understand how they got there.
- They didn’t really know what was most important at that moment.
- Holy shit, we’re busy.
What Are We Optimizing?
The first question I asked: Are we working backward from the next fundraise, profitability, or an exit?
They wanted to build something large. That’s easier to do with other people’s money; relying on cash flows alone would slow them down. Profitability would give them more control but less speed. An exit? Not even close to being the priority.
Answer: Series A.
What Investors Need
Given their category, geography, and stage, what would they need to demonstrate to earn that fundraise?
Most founders answer this question themselves. They set targets that feel ambitious, assume investors will be impressed, and build toward numbers they invented. That’s a trap.
We went to the source. We talked to board members, current investors and prospective ones. We examined published data on category benchmarks across PitchBook, Crunchbase, and Carta. Not long after, we had a clear point of view grounded in what actual investors in this category were funding.
This is the step that changes everything. You’re not optimizing for what sounds good internally. You’re calibrating to what will move the specific humans who need to write the check.
Now we knew the destination: Series A. And we knew what would need to be true to earn it.
Startup to Machine
From there, the question became: What would have to change about the business to achieve those metrics? To go from seed, where everything kind of works, to a Series A company with a reliable, repeatable machine?
Gabby’s team needed to reach 3x growth in annual recurring revenue. That meant closing 20 new customers per quarter at their average deal size, while boosting revenue retention above 100%. The current lead channel was producing roughly 10 qualified opportunities per month. Nowhere near enough.
What actions would it take to actually realize those metrics?
- The product would have to improve to drive retention.
- We’d need to unlock a new lead channel, since the current one was tapped out.
- We’d need to move from founder-driven sales to a repeatable sales motion. Gabby couldn’t personally handle the volume we were targeting.
Three steps. A founder shifts from opacity to clarity by answering them in order:
- What milestone are we working backward from?
- What intel can we gather to get to crisp targets?
- What work has to happen to achieve those targets?
Don’t Work Harder. Work Backward.
Fifteen months later, the metrics were there. The investors said yes. Gabby raised her Series A.
According to Carta, less than 30% of seed-funded companies ever reach a Series A. Gabby is in that 30%, not because she outworked the other 70%, but because she worked in the right direction, calibrated against validated targets.
Don’t push blindly ahead. Pick the next destination, find out exactly what it takes to get there, and work backward.