Telling Failure Stories in a Successful Way


Entrepreneurs are always selling. When you're the founder of a startup, you are your company. You're in a constant state of pitching. And one of the most important tools to have at your disposal while selling is a matrix of stories.

In Craig Wortmann's video on Entrepreneurial Selling, he talks about the story matrix, likening it to a metaphorical quiver resting on an entrepreneur's back with arrows marked for specific purposes. Each arrow represents a story type meant to convey a specific, captivating message to a targeted audience. Hopefully, this story will elicit action from its audience, forging a partnership, buying a product or making an investment.

It can be a little overwhelming to think of and remember an entire collection of compelling stories related to your business, but Craig’s matrix calls out the most important story types (success, failure, funny, and legend) and topics (investment, hiring, qualifications and expectations), giving entrepreneurs an easy-to-complete grid. He’s narrowed it down for you, now you just have to document and become familiar with your stories in a way that makes telling them second nature.

One of the categories that I absolutely love is failure. There are more and more narratives coming out about not just entrepreneurial failures themselves, but the benefits (not to mention the value of actually talking about them) of them as well. Craig makes it clear that this is by no means a “look what a moron I am” category, but a lessons learned category.

Stories in the failure category can be pretty powerful. Here were a few I found:

-       Losing a Battle, and Focusing on Winning the War: Entrepreneur Andy Sparks talks about moving on from a failed startup in this very transparent series on failure.

-       Postmortem of a Venture-backed Startup: This one’s all about the lessons learned from @Sonar, a mobile app that raised nearly $2 million and still failed.

-       The Decline and Fall of Flowtab, A Startup Story: This widely-read chronicle of death detailed the short-lived life of an iPad-driven technology for ordering and paying for drinks at bars.

All of these stories give the entrepreneurs credibility, humility, and experience. They don’t make them look like idiots. In fact, they make them look like smarter entrepreneurs who have learned from their failures and aren’t afraid to let others do the same.

What’s been the most effective story in your matrix?

Was this helpful?
  • Amanda Schnieders