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The Art of Storytelling

Let me tell you a story …

People like to think are logical and rational, or at least can be when they have to. That’s true for nearly anyone. But there’s a catch buried deep in our brains that makes it tricky.

We remember nearly everything in stories. We remember a web of images, smells, tastes, feelings, and yes, even numbers when we have to in a bigger context that makes them meaningful to us.


A duck walks into a bar. Maybe he’s a regular?

Learning how to build the web of connections isn’t hard because what you rely on is the imagination of the person you are telling a story to. They do all the work if you set it up right. And building a memory with a deep connection is critical for creating loyalty to a company, a product, or a vision of a new world.

Every start-up entrepreneur has to know how to tell a story. Exactly why becomes obvious if you think about what makes a story good.

It isn’t that hard if you think about the process and pay attention to the way you remember stories yourself. The setup is a lot like telling a joke in a way because basic elements are the same. Those are:

  • The Setup
  • The Twist

With a joke, the setup is critical because it tells someone, “Get ready to laugh!” That can be as simple as “Knock-knock!” or “A duck walks into a bar.” How many jokes have you heard that fell completely flat on the ground because you didn’t even know it was a joke coming your way? But it’s the twist that brings da funny, that’s the part that makes it memorable. Without the punchline running askew of the setup there’s no joke and no big laugh.

Not funny? Well, analyzing humor is like dissecting a frog – no one is interested and the frog dies. But these have a lot to do with storytelling.

The Setup

You have to start by opening up the mind of the person who you are telling the story to so that they are receptive. There are many ways of doing this, but the best way is to call the curiosity of your reader to mind. The best advice for this comes from Horace, a Roman poet who lived over 2,000 years ago:

In media res – Begin in the middle.

This is the moment it all got weird.

This is the moment it all got weird.

This is the hard part. Let’s start building a story based on something that happened to you. You lived it, so you know it well. You know when it starts, how the situation was setup, and when the big twist came that made you learn something, connect with someone, or otherwise do something so memorable you just have to tell the world. The only problem is that you don’t have the right setup that’s going to make that story register in the mind of the person you are telling it to.

Here is an example of how to draw someone in and setup the story:

WRONG WAY: I was driving to work pretty much like any day, taking Summit Avenue because I-94 was backed up badly. It wasn’t a street I normally took but everything was all crazy because the President was coming into town. Everyone was late for work like I was and tempers were short. It was obvious something bad might happen.

RIGHT WAY: In that moment when the steel started to crumble and a shower of glass fell like driving rain around me, I knew my life was about to change. The panic that ran hot in my blood in that brief instant shot through the worst that could happen – paralyzed, comatose, even dead. Little did I know that ahead of me was a meeting with the President – the moment that really did change my life.

So you may be thinking that the “right way” gave away the whole story, and it pretty much did. But the reader knows the point of the whole story and why they should keep reading or listening. They know there’s a big delivery at the end – but they still don’t know quite what.

It’s not quite the same as telling a joke because the twist may or may not be the big payoff – in tears, philosophy, idea, or product. But it’s there, and it’s what separates something worth telling as a story and a boring recap of a boring day.

What does any of this have to do with entrepreneurs?

Twisting it Deep into Memory

Telling a good story is all about the understanding the process by which an otherwise ordinary event becomes memorable. You want your business to be remembered, whatever you are pitching. It doesn’t matter whether it’s an idea, a product, an investment strategy, or maybe even a religion. It has to connect with people and stay in their heads. The most important part of this is understanding the basic elements of starting in the middle and putting your best hook up front so that you earn the space in the imagination of your reader or listener. From there, they write the rest.

Yes, Colbert invented the word - but the concept has been around a long time.

Yes, Colbert invented the word – but the concept has been around a long time.

The setup isn’t the only important part of a story, of course. There are many important concepts that you have to keep in mind:

  • The Moral – Yes, everything is a fairy tale. What’s the story about? What is the real punchline? You may remember details about how you got to the end, but if they don’t serve the point of the story they need to be left out.
  • Truthiness – Everything about the story has to feel real, even if it is made up. The characters have to act like real people would in the situation, no matter how bizarre it gets. The setting itself has to feel like something that might happen. The reader simply has to be able to put themselves into the story.
  • Progress – Your story has to move along, and do so in a way that gets the reader to the moral while felling true the whole time. Don’t let it get bogged down in detail – action and dialogue are always the key.

This is where storytelling is a lot more than telling a quick joke that leaves ’em rolling on the floor.  The twist is the progress of the story – which is a lot more than just one punchline.  A good story may have many twists and turns in its progress and that’s all good – assuming that it all feeds into the moral and doesn’t upset the truthiness.

How does this Work?

It’s time to show an example of how these come together with a strong setup to sell a product. Here is one that seems really far afield from the process of storyteling:

Flo, the Progressive Insurance Agent.

You know who she is.

You know who she is.

What does storytelling have to do with 30-second commercials, told in little pieces? All the elements are there, and over the course of many commercials the story is built. The medium for storytelling is lousy, but it’s all still there. How?

First of all, we have the setup. Each time we are thrown into the middle, at a place where the customer is walking in or somehow dealing with Flo. We don’t know who she is or any of her backstory. Everything that came before has to be invented in the mind of the viewer, and it’s going to be a little different in each case. There is a strong setup, and it’s a situation that is familiar to everyone who has had to buy insurance.

But in that setup something is just a little askew. Flo is personal and familiar, like someone you already know. She doesn’t look like an insurance agent – and is sometimes contrasted with guys in suits who do. The setup is a lot like a joke, and each little episode often has a joke built into it.

Yet the basic elements are there in each episode all the same. The moral is consistent – we are a different kind of insurance company, the kind you will like dealing with. There is a truthiness to it brought in mostly by Flo and her matter-of-fact personality. And there is progress in every little episode, advancing the characters and revealing just a little bit more about them.

It’s not like a long narrative of text, but it still has it all.

Flo is a good example of using the elements of storytelling to build a brand, but sometimes that’s not what’s called for. Storytelling is a powerful way to build interest in products, especially if each one has its own story of craftsmanship, creation, and love.

What Storytelling Brings

AHAlife is an online retail company that “curates” products from around the world. Each one has a story behind it that is critical to explaining why the product is essential for the life of any potential buyer. They saw tremendous growth in 2011 because of their attention to the principle of storytelling for each product that they sell.

It's the sizzle that gets your mouth watering.

It’s the sizzle that gets your mouth watering.

Let’s let founder Shauna Mei explain in her own words:

“It’s very important to hear where someone gets their start from and where the inspiration started. Every time a designer comes in I ask where they are from and where they studied. It’s not just about their product. It’s what got you to the product too.”
“You might not think this is interesting, but people who buy for quality really care about the process. Our customers care about a certain workmanship and quality with their purchases.”

This is a variation on the old saying, “You don’t sell the steak, you sell the sizzle.” Potential buyers can get products anywhere that fill whatever need they have and that’s fine. But to sell a particular product, particularly at the high end, the story behind it and why it’s superior is critical.

And by providing the story behind every product you are inviting your customers to be more than just buyers – they become a part of the story, too. An elegant piece of stemware may attract attention, but when your the host of the dinner party feels compelled to share the story of the artisan who crafted it and where it came from you have turned customers into advocates.

And You?

These are just examples of how storytelling can be used and how powerful it is. How do you get started telling your own stories?

Tell me a story ...

Tell me a story …

First of all, have a clear vision of the moral or point of the story. Forget for a moment how you got there and all of the details that propel the story along, develop a clear purpose for your story that you can remain true to paragraph by paragraph, minute by minute, as the story progresses.

Once you have that firmly in your mind, and ideally written in big letters on a whiteboard where you’ll see it constantly, you’re ready to start. It’s time to come back to details of the story that make it worth telling.

But what is that moment when the point of the story starts to crystalize? When did you feel that idea explode in your brain with a huge “Ahhhh!” that boiled in your blood? When did your life change in a way that told you there was no going back? That’s where you have to start.

Once you have the moral and the setup, you have the most basic elements in place.

How do you go on from there? One method that is very helpful for many people is to think about the progress of the story in terms of another story that you know very well. “Star Wars” and many other epics take the form of a very old kind of story called a “Hero’s Journey”. It’s very popular right now because of its power. These are stories of discovery, either an object or a great truth, and personal development through the journey.

Once you know just what your story is about and understand the moment of change you may want to think about what kind of story you have.

This is not cheating by any means, but a big part of the ancient process of repeating and refining stories. The main goal is to have a great setup that gets your reader’s attention right away, and what better way than to set it up with something that they already know?

Organizing the details of the story are then just a matter of putting in the details. They need to either enforce the moral, the truthiness, or the movement of the story – if they don’t, leave them out. Remember that the problem with real life is that it doesn’t have to make sense, but a story does. There are a lot of things that happened along the great adventure or revelation that you had which don’t really help a lot.

Is that all there is?

There are more things to consider, of course, but these are the essential elements. There are exactly two ways to become proficient as a storyteller, and they are by reading and by writing. The more you practice the art the better you will become. But if you pay attention to these elements and how they are used you can read a story or watch a movie with a much more critical eye that helps you understand the craft better

That moment.  That's what it's about.

That moment. That’s what it’s about.

Oh, and sorry if I just ruined most movies for you by saying that.

There are other considerations. Watch your adjectives so that they don’t get too “purple” on you – it’s important to make sure that the words you use aren’t outside the normal experience of your readers. And remember that spoken English is not the same as written English in that writing has to have some structure to it in order to make sense. If you write exactly how you talk it will naturally drift a bit, which is how you can lose readers.

But the most important thing remains that you are asking your readers or listeners to paint in their own minds the details that make your story memorable. They are building connections in their own mind, and you can’t always force that.

Once you have this down, you can use storytelling as a tool to sell just about anything. There is nothing more powerful than getting your story deep into the mind of the people that you need as customers, investors, or comrades. It’s not mind control, but it is an ancient way of getting more than just a point across – it’s a way of building trust, friendship, and even love.

Love your craft and all the rest will follow, including success in your goals as an entrepreneur.

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