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Stewart Butterfield: If You're the Kind of Person Willing to Tilt Your Umbrella, There's a Whole World of Opportunity

By Stewart Butterfield · Investing · 1 min read

Most people walk through the world oblivious to the problems other people have. And if they notice them, they can't think of a solution. Which means if you're the kind of person who's willing to tilt your umbrella — there's a whole world of opportunity out there.

Key Points

Look at your own experiences as a consumer — every frustration is an opportunity
Most people are oblivious to problems, and if they notice them, they can't think of solutions
Pay attention — especially to other people and what seems broken

If you're the kind of person who's willing to tilt your umbrella, there's a whole world of opportunity out there.

Every Complaint Is an Opportunity

Butterfield: I would definitely look at my own experiences as a consumer. It's very easy for me to see things that are frustrating. I complain about stuff a lot. My life is really good and yet every time I have to fly somewhere, I have at least 10 significant complaints and 50 minor complaints.

Every one of those is an opportunity. Some of those seem like someone else should see them and it should be really obvious — but they're often not.

My life is really good and yet every time I fly I have 10 significant complaints and 50 minor ones. Every one is an opportunity.

The Umbrella Story

Butterfield: I tell this story in our internal onboarding. Me and our head of product design going for a walk in Vancouver. Our office is in a neighborhood with really narrow sidewalks — sandwich boards, vendors, very crowded. It starts raining. Two-thirds of people had umbrellas. We didn't.

People are walking towards us and almost no one would move their umbrella so the pokey things wouldn't get us in the eye. The sidewalks are very narrow so we had to keep ducking.

There's only two explanations. Either they walk through the world and don't see that we're ducking to get away from their umbrella — even though they've had that same experience themselves. Or they see it happening and just can't think of anything they can do — despite the fact that it's a hundredth of a calorie worth of effort.

Either they don't see the problem, or they see it and can't think of a solution. Despite a hundredth of a calorie of effort.

Pay Attention

Butterfield: That's a sad way of looking at the world, but that's the way most people go through it. They're oblivious to the problems other people have. And if they notice the problems, they're unable to come up with any kind of solution.

If you're the kind of person who's willing to tilt your umbrella, there's a whole world of opportunity out there. Pay attention — especially to other people and what seems broken. In Y Combinator's history, when people have needed to come up with a new idea on the fly, it doesn't usually work. But when they really commit to paying attention to other people and what seems broken — that has worked.

Pay attention. Especially to other people. When YC founders commit to noticing what's broken — that has worked.