Keeping a Little Crazy

I had the pleasure of spending some time with Patrick Collison in Dublin for the launch of Stripe Ireland a few weeks ago.

Stripe, to me, is the hallmark of a modern company. Every aspect of their business, from the outside at least, appears to be meticulously researched, and, to my taste, done just right. From their marketing, to their API design, to their systems, processes, and their willingness to rethink fundamental operations.

Stripe is a massive business role model for me. That’s why, during the few times that I’ve had a chance to talk to Patrick, I listen carefully.

The story he told that resonated with me most was about the foundation of the Stripe idea. The idea at the beginning was simple: to rethink payments on the internet. Having sold Auctomatic as teenagers, the Collison brothers had more access to influential people in the payments industry than most.

Unfortunately, when Patrick pitched the idea for Stripe to several influential figures in the payments industry, he got responses that he wasn’t expecting: “It’s too hard”, “it won’t work, and here’s why”, “you won’t be able to convince X or Y or Z”.

Rather than going away excited and full of advice from people he respected, he was disillusioned because of their lack of belief.

I remember similar conversations after Eamo and I decided to run “A conference on a bus for technology people”. We’d get the occasional snigger, or a comment that we were asking for trouble.

People tend to criticise new ideas from the point of view of their own experience. Sometimes not having that ingrained experience is the key to inventing new solutions to existing problems.

For me, keeping an open mind is the best way to prevent this kind of thinking. We try to keep an open mind when discussing the future of Tito. No idea is too shit. No existing work is immune to deconstruction. We try to create an atmosphere where anyone can say anything.

Sure, we’re building an app that’s ultimately being used by other people to help run their businesses. Crazy for crazy’s sake won’t cut it, but being a little crazy helps us bring ideas to the table that otherwise may have been shot down sooner. By allowing each other to pitch crazy, we often stumble upon the ideas that we’re most proud of.