The sun wasn’t quite up yet—just that silent, steel-blue predawn light. I was out walking the dog (a routine mandated by life with early-rising children; you surrender your sleep schedule the moment they arrive). It was quiet, save for the rhythmic whir of expensive carbon fiber rolling down the street.

As is common on weekends, a group of dedicated cyclists were out: fully geared up, lights flashing, moving with meticulous, synchronized efficiency. Then, moving against the flow, close to the kerb, came a bloke on an old bike—probably heading out for a paper run or an early shift. While traffic was non-existent, he was definitely breaking the rhythm of the morning.

What happened next was an apoplectic “HEY!” from one of the decked-out dudes in tights. He was clearly startled first, then instantly irritated by the obstacle that A) he didn't expect to be there, and B) shouldn't have been there if everyone just followed the rules.

I had a little chuckle. I live in Singapore, where you do kind of expect minimal variance. If I were back in most other places, the cyclist would have simply moved over slightly, given a grin (or grunted in irritation, depending on his mood), and treated it as a non-event. But here, the unexpected—even a solitary bike rider—can provoke a minor existential crisis.

The Founder’s Lesson: Expect the Unexpected

The reason this moment stuck with me is simple: when you're carving out a path in the 0-to-1 stage, your default setting ought to be: expect the unexpected.

The world of a first-time founder is often like that of the cyclist in tights—assuming the road will be clear. They operate based on a rigid mental roadmap of how things should work: "This pitch deck should get funding," "This feature should achieve product-market fit," "The competitor shouldn't have done that."

The second-time founder? They are the ones who have ridden on many roads in many countries. They've already been yelled at. They’ve crashed once. They know the rules are merely suggestions to some, especially when you’re moving in the dark. They don’t allow obstacles to get them bent out of shape—unless it’s serious enough to warrant a full pivot.

While I'm sure the decked-out cyclist went back to focusing on his routine, and the encounter quickly became a non-issue for him, maybe, just maybe, the next time he takes his bike out, he'll remember that life—and building a company—will throw you a curveball every now and then, just to keep us all on our toes.

Happy building!