You Can Survive Chaos. You Can’t Survive Misalignment
Reflecting on my year in a pre-seed tech startup
In the summer of 2022, I found myself in Boom, Belgium — shoulder to shoulder with thousands of Europeans at their annual techno pilgrimage: Tomorrowland. I had recently caught the travel bug and spent the past year bouncing around as a digital nomad, chasing sunshine and decent Wi-Fi. But even then, I was never fully unplugged. I was always tethered — to my laptop, to Slack, to the slow drip of corporate obligations.
This time was different. No Zoom calls. No spreadsheets. No inbox to manage. Just movement and a little indulgence. A soft reset.
But this wasn’t just a vacation. It was a layover between two lives.
Two weeks earlier, I’d left behind a well-paying job, a reputable title, and the steady predictability that comes after being the acquisition target of a Fortune 500 company. I’d spent years building credibility inside a scaling startup — and doubled down on this approach in its corporate afterlife, but in my heart I felt our mission had been accomplished. I could’ve stayed. I could’ve coasted. But I wasn’t built for coasting.
So, I threw myself into something riskier: a five-person startup with few customers, a half-formed product, and a founder I hadn’t met in person. The mission was vague. The plan was thinner. But the challenge? It was real. And I was hungry for it.
On the flight back from Lisbon to Toronto, I tried to shake off the backpacker mindset. It was time to go from “passenger” to “pilot.” Game on.
Into the Deep End
By day two, I was already pitching — learning on the fly, scrambling to define our ideal customer profile. At first, it felt energizing — engaging conversations, positive signals. But when you’re Head of Sales, signals aren’t enough. Conversations without outcomes start to feel like failures.
Every day, the same question echoed:
“Have you closed anything yet?”
The answer? Not really.
Because the more honest question was this:
Who the hell are we actually building for?
Not All Revenue Is Created Equal
One of the toughest lessons we were learning was that revenue isn’t necessarily proof of success — not at this stage. Revenue comes in a variety of different forms. And not all revenue is created equal.
I started thinking of it like a traffic light:
Green money is aligned. It grows. It compounds. These are the customers you want to serve.
Yellow money is cautionary. It might stick around, but you have to be careful. These customers will request random features and eventually they may weigh you down requests and meetings that lead nowhere.
Red money is dangerous. It’s distracting. It burns cycles and steals your focus.
The tricky part? Red money looks just like green money when it hits your bank account.
At the time, we didn’t even have an ideal customer profile. No filters. No language. No real definition of the problem we were solving — just vague belief that “we’re onto something.”
And so, I spun. Not forward. In circles.
Alignment Isn’t a Luxury. It’s Survival.
When you’re spinning your wheels, grasping for traction, there’s only really one remedy that can get you out of your death spiral: Your team. And your team has to be in alignment on what you’re aimed at. The tricky paradox is you can’t really force alignment. Everyone has to make the decision to buy-in. And if it isn’t there, the lack of it hangs over everything you do, like a dark cloud of startup depression.
I had conviction. But conviction alone doesn’t yield results. Not if your product team doesn’t feel your customer’s pains. Not if your founder doesn’t hear the customer’s voice for themselves. Insight doesn’t translate if it’s stuck inside Slack threads or slide decks.
Misalignment doesn’t kill you overnight. It’s slower than that. It’s decay. A team working on different songs, each one slightly off-key.
Focus is the Antidote
When chaos sets in — and it will — the only thing that saves you is focus.
Focus on the right customer.
Focus on the problem worth solving.
Focus on building something that’s repeatable.
Sounds obvious, right? It’s not. Because distractions don’t show up looking like distractions. They show up dressed as opportunity:
A surprise RFP from a massive brand
A flashy investor request
A “quick win” feature for a potential partnership
Each one is potentially a short-term, one off revenue spike. None of them builds long-term, compounding growth.
Bet on the Whisper
Even now, I hesitate to go all-in — not from doubt, but because early signals are rarely obvious. Growth doesn’t scream. It whispers. And you’ve got to be tuned in to hear it.
Product-market fit? It’s not a moment. It’s a murmur. A pattern. A handful of people using something the same way — repeatedly, without being told.
When you hear that? Double down. That’s the thread you pull. That’s where growth lives.
The Real Playbook
Looking back, here’s the simplest equation I learned during that tumultuous year — and re-learned the hard way over and over again:
Know your customer
Solve a painful, high-value problem
Say no to distractions
Move in sync: product, GTM, and leadership
Repeat what works. Relentlessly.
Simple? Yes.
Easy? Never.
But if you’ve got even half of this in place, you’re ahead of the pack. If your team can agree on the song and play it in tune — again and again — you have a shot.
We were close. I see that now. I’ve spoken to some of those early customers we nearly won or had worked with briefly. The pain was real. The opportunity was real. We just didn’t move in unison.
And that’s what separates startups that scale from startups that fail.
Not brilliance. Not luck. Just alignment. Execution. Repetition.
I went into that startup thinking I’d be the hero. The closer. The one who unlocked revenue.
But startups don’t just need heroes.
They need harmony.