Once upon a time, waiting for an Uber

In the first season of StartUp, Alex Blumberg talks about an early pitch to Chris Sacca, for what would later become Gimlet Media. On a sidewalk, under pressure, it doesn’t go well. Chris Sacca steps in and translates. He plays the conversation back with the contemporary constraint “in the two minutes it’ll take for an Uber to arrive”.  Compelling and to the point, its pitch perfect.

The ‘pitch’ is a modern form of storytelling. And the pitch itself can be enough; to win investors, partners, even customers. In business, as in life, stories matter. A lot.

The value of authenticity and narrative arc are widely acknowledged in shaping how compelling a story is. In ‘A Debate with Malcolm Gladwell from WorkLife with Adam Grant’, however, Malcolm Gladwell and Adam Grant focus-in on another quality of storytelling “interestingness”.

For Malcolm, “…that quality of being specific and being able to illustrate your larger points with… precision is the quality of what makes something interesting.”

For Adam, interestingness has its origins in a certain kind of… pause. Drawing on the work of sociologist Murray Davis he suggests that “If someone just affirms your assumptions, you don’t get curious, you don’t get intrigued, there’s no surprise… when you’re interested is when it’s like ‘huh’, that’s the opposite of what I would have thought, or that’s different from what I would have believed”.

So if M. Sanjayan’s right and storytelling is a way to rule the world, well that’s a craft to master. Time to take “Once upon a time” and crank up the ‘interesting’.

Try this at home kids!

  1. Pocket full of stories: without little eyes watching, pop four or five everyday items into the pocket of a coat. This is now the storytelling coat. Get the kid(s) to put it on, check their pockets and then tell a story incorporating the objects they find.
  2. First half / second half: begin by telling a story out loud. Right after you get to a critical point, stop and let the kid(s) take over.
  3. The pitch over dinner: at breakfast time, ask the kid(s) to keep an eye out during the day for a ‘problem’ they encounter and to come to dinner with an idea to solve it.  The problem doesn’t need to be enormous – a top that’s hard to get on, pens and socks that keep disappearing – anything that doesn’t go smoothly will do.

In each case, encourage the kid(s) to make the story as interesting as possible. Talk about what might help with this. Perhaps by incorporating a real story, something they have experienced, getting very specific or getting characters to do the opposite to what you might expect.

Thank you for the inspiration Alex Blumberg (@abexlumberg), Chris Sacca (@sacca), Adam Grant (@AdamMGrant), Malcolm Gladwell (@Gladwell), Guy Raz (@HowIBuiltThis) and M. Sanjayan (@msanjayan) ℅ Tim Ferriss (@tferriss). All masters of their particular storytelling craft.

Postscript

For more inspiration, Nancy Duarte‘s Resonate is a masterclass, and modern take, on “Once upon a time…”.

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