Humility gathers advocates

The Confession
Having gotten their attention by taking their money, we made our confession with a slide titled “140 Reasons Square Will Fail.” The slide listed all the potential fatal problems that our team could imagine, from predictable threats like fraud or bank regulations, to more outlandish possibilities, like a robot uprising. …

Our “140 Reasons” slide had a miraculous effect on our VC meetings.

Most VC pitches are nothing but sunshine and graphs moving up and to the right. To honestly examine all the hundreds of possible events that can kill a new company was just not done. But it showed we were thoroughly thinking through all the angles and unafraid to confront potential problems and future robot overlords.

It also had a strangely positive effect on the mood of the meetings. Normally, the company founders pitch an idea while the VCs try to find problems with that idea.

By presenting every possible problem that we could imagine, we changed this “attack and defend” vibe that often dominates such meetings.

By the time we got through the 140 reasons, the investors were ready to be led anywhere.

Source: The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time by Jim McKelvey