Why You Need to Tell Failure Stories

July 22, 2015

3:00 pm

When Airbnb got rejected by 7 investors, it was undoubtedly a big blow. But today – with over $2 billion in funding under their belt – that struggle has turned into an inspiring failure story (and a bit of sweet revenge).

And according to professor Craig Wortmann, failure stories are the most powerful way to sell your startup.

Stories of success are a dime a dozen, and that’s part of the problem. We sell ourselves by tooting our own horns – amassing flattering statistics, name-dropping, listing bullet points from our fluffed-up resumes. But without mentioning any failures or setbacks, all that positivity just sounds fake.

As a journalist, I’m constantly getting emails about the thousands of downloads, famous customers, and heaps of funding a startup has. Yawn. But send me an email about your visa issues or your panic attacks, and I might just read it.

In a recent video from the Kauffman Foundation’s Entrepreneurship.org, serial entrepreneur and University of Chicago professor of entrepreneurship Craig Wortmann explains why entrepreneurs need a toolbox full of different stories to tell their customers, investors, and potential employees – and why failure stories are the most powerful.

“Your ability to tell a compelling failure story is engaging and magnetic,” he says. “They demonstrate humility, they demonstrate the ability to learn, the ability to process, the ability to move quickly and adjust and pivot.”

They aren’t “Look what a moron I am” stories, he hastens to add. The point is to show how you gained all that knowledge and expertise you claim to have.

Wortmann suggests you sit down and create a story matrix, a table of stories divided up into rows and columns. The columns are the four types of stories you can tell: failure, success, fun, and legends. (Fun stories are simply funny or engaging, while legends are epic tales like the ones often told of Steve Jobs.)

failure stories

For each type, come up with stories about different topics (the rows in your story matrix). You might have stories about investment or hiring; you might even have specific stories related to qualifications or setting expectations. For example, one of Wortmann’s “failure of expectations” stories involved landing a big customer by completely overpromising what his company could deliver – and having to drop that customer later.

Your stories are like a quiver of arrows, Wortmann says – in the heat of battle, whether you hit the mark or not depends on picking the right weapon.

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Kira M. Newman is a Tech Cocktail writer interested in the harsh reality of entrepreneurship, work-life balance, and psychology. She is the founder of The Year of Happy and has been traveling around the world interviewing entrepreneurs in Asia, Europe, and North America since 2011. Follow her @kiramnewman or contact kira@tech.co.

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