The Year of Crossings

A startup, an ocean, and the gradient in between

© Wren Halliday

It was a year of steep gradients. Last December I threw myself onto the founding side of the table; this December I am writing from a rented desk an ocean away from everyone I grew up with. Life rolled in directions I could not see one step ahead of, and getting through each day took everything my body and mind could lend it. Small wins sat next to a strange, unnameable unease, and the unease cost me more sleep than I want to admit. Maybe because of all that, I got to meet every version of myself this year — the sturdy one, and the clumsy, chipped one too.

Boarding the Rollercoaster

Why are rollercoasters fun? Nobody ever says a rollercoaster was great because it climbed so high. It is fun because it drops — steeply, all at once. And you don't feel the thrill in the drop itself; you feel it after you step off, once gravity feels normal again. Startups, I learned this year, are built on the same physics.

Joining a team as a co-founder when the company account was down to its last three hundred dollars was, in hindsight, not an entirely sane decision. What I fought during the first week was not the market but the helplessness soaking the room — a couple of pivots had already come back stamped as failures. Jonas, our CEO, had a talent for compressing panic into a deadline: “We ship this in two weeks.” So we did. Two weeks, one landing page, and a build held together with tape.

Driftnote started from that corner of desperation. I kept losing half of every customer interview to my second-language ears, and I wanted the words on the screen before they faded from the air. We built it for ourselves first — and then, three days after launch, a company we had never spoken to signed an enterprise contract. It was a small number on paper. It felt like a season changing.

A Land Seven Timezones Away

From the beginning we had two goals that were really one goal: build a product people quietly depend on, and become a company that isn't bounded by the map it started on. Saying “we will be an international company” out loud felt presumptuous at first. Then it started making our decisions for us.

In March we flew to San Francisco for two weeks of meetings that changed nothing on paper and everything in our heads. In June we made the hard call to spin Skerry off as its own product instead of keeping it a feature. And on September 15 — a date that had lived circled on the whiteboard for months — we kept the promise we had made to ourselves and moved.

The first weeks in a land seven timezones away were a course in small recalibrations. Grocery stores organized by a logic I hadn't learned yet. Small talk with strangers as a default setting rather than an exception. Sunlight that ended the workday before our hometown had woken up. None of it was hard, exactly; all of it was new, and newness by the kilogram is its own kind of weight.

Friends around a table on a warm game night — Photo by Pavel Danilyuk on Pexels
Saturday game nights kept us sane.

The Accelerator

I first read about the accelerator in high school, in a blog post I only half understood. Eight years later, after seven applications across three companies — three interviews, four silent rejections — we got into the autumn batch. I read the acceptance email three times before I said anything out loud.

Being in the batch feels like it will be one of the real hinges of my life. Some thirty thousand teams from everywhere apply; the ones who arrive are all carrying a version of the same unreasonable belief. Standing in a room where that belief is the ambient temperature does something to your own.

During one of the batch talks, our group partner Priya said something that has stayed pinned to the inside of my head.

“Most of what happens to you in the next few years will not follow the plan. That is not a flaw in the plan — the plan is just paper. What you are actually building is a team that can rewrite the paper faster than the world tears it. Build that, and be kind to yourselves while you learn how.”

Stripped of its warmth, that means the next few years are guaranteed to hurt. My head knows the long game rewards the ones who stay; it is still frightening to hear the pain described as a certainty rather than a risk. The consolation is that we have already walked through a few small hells of our own — we know how a pivot fails, what it costs, and what we would build next if this one goes down too.

So: with the patience of someone rolling a snowball. Start small, keep it moving, and don't mind packing it again when it cracks. The long, long walk has only just begun.

Night Tides — Low Season [M/V]
♫ Night Tides — Low Season