Storytelling Tips for Startup

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  • The best storytelling is a form of entertainment
  • Emotions > Facts
  • Stories can be an incredibly powerful force, and their value is one of the core theses.
  • Storytelling is more effective when it builds trust

Why Stories Matter

Storytelling matters across all dimensions of a startup: pitching investors, recruiting talent, selling products, building a cult-like following. It's an undervalued art in most companies, and especially in technology.

When you are in a business driven by optionality, like the venture capital business, investing a lot of resources in creating spreadsheets is a waste of time since the assumptions in it are guesses. The best way to quantify the opportunity is actually with a story.

The art of storytelling is incredibly important. Learning to tell a story is critically important because that’s how the money works. The money flows as a function of the story. -Don Valentine (Sequoia)

For most VCs, It’s very hard in the early, nascent, embryonic stages of a business, to really know if somebody is going to be an absolute genius or a total fraud. Because the best storytellers are also the best con men. Amazing narrative storytelling ability that captures all of the best and worst things about humanity. It captures our aspiration, our virtues, our sense of status, desire, greed, and people that can tap into that, who understand people, I think are really influential with people, are almost always predictive of great success.

A founder/builder/designer who is a great storyteller is really good for a startup business because they can recruit really well. They are telling a story where you meet with that person, and one of my partners used to call it, somewhat inappropriately, the Pampers effect. You’re like, wetting yourself, you’re like, “Oh my god, I need to join this person. I need to invest with them".

Craft a Compelling Story

Great stories generally share some common traits — they’ve got interesting characters, an emotional plot, a set of challenging circumstances and (in some cases) a happy ending or hint of what’s to come. Your company story should be no different. The compelling characters might be the team and what drives you to do the work you do, or it might be the audience you are addressing. Think about your personal experience that has led you to where you are today.

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The critical point is to make sure that every stage in your story arc adheres to the ‘be interesting’ rule. If it’s not interesting, cut it out. You can always dive deep into the detail later.

If you tell them a story and they buy that, they also don’t care about what product you make but what story your product tells. Because, if it tells a good enough story it is a story they can then sell to consumers.

Be Prepared for Any Angle

Craft a pitch, and be fully prepared, for any of the following common situations:

  • 45-Second Pitch
  • 3-Minute Pitch
  • 30-Minute or 1-Hour Pitch

By preparing for your common pitching needs, you’ll have a library of slides and talking points that can be used in all types of situations.

Building this story, or structure, not only helps keep your pitch on time, but it can prevent the dreaded ‘pitch pause’ and keep your audience entertained at the same time.

The better this story ties everything together, the more your business will seem insightful. Ultimately we’re all human, and strong narratives that help explain the world around us are more compelling than a selection of disparate, albeit impressive, data points.

Remember, it’s a trust building exercise. In a relationship, trust is built over many interactions over a long period of time. You want to show some positive elements to get people interested, but leave surprises in reserve.