The Art of StorytELLING

by / ⠀Entrepreneurship Podcast / June 19, 2015

Entrepreneur Storytelling

In 2009, Joshua Glenn and Rob Walker decided to put a price on storytelling. The pair would buy “junk” worth little to nothing and then re-sell it for 300 times its original value. All the proceeds were donated to charity. Why did they do this?

Simply put, making a killer profit wasn’t their point. I believe the point was to reveal the value of StorytELLING in the process of selling.

They didn’t do this just once; they did it time and time again. There are even examples where the markup they achieved went well beyond 300% of the initial purchase price.

In one case, Josh and Rob bought a globe paperweight for $1.49, which they then proceeded to sell for $197.50! Then there was the wooden apple core they bought for $1 and sold for $102.50, and the time they bought a fake banana for 25 cents and sold for $76. You can read about all their crazy adventures and achievements in their book, Significant Objects.

How did Josh and Glenn manage to sell what was essentially junk for so much money? By attaching great stories to the objects.

But that’s enough about Josh and Rob.

A Stanford study found that stories are 22 more times memorable than facts.

How does one tell a memorable story?

Start with the ARCH

Many people considered me stupid in school. Heck, there was a time when I even considered myself stupid.

However, one must be aware, because the stories we tell ourselves about our character become our reality.

Now, why did I tell you that part about being stupid?

Because I knew it would catch your attention. You may still be wondering why you’re bothering to read something by a writer who is clearly still honing his craft (how in the world did this guy even become a writer…?).Stick with me because the point is important even if the writing isn’t world-class.

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Always start with the most interesting point in the story. This is what I call the ARCH. The arch can be at the beginning, middle, or end of a story, but always start with it.

Then move through the story.

Become Vulnerable

Last week I felt such pain. I came across a story about Madison Holleran. She was an extremely bright student at UPenn, stunningly beautiful, a star collegiate athlete and…depressed.

The tragic story ends with her death. A constant theme in the story was how we all filter our lives via social media, which allows us to create fake lives.

These ideal lives are illusions bearing little resemblance to what is often a painful reality.

If you want to tell a compelling story, be AUTHENTIC, be VULNERABLE, and be REAL.

When you contemplate sharing a personal story where all three are present, your heart rate increases because you fear no one will like you. In reality, the exact opposite occurs. You just might not be aware of the effect as few will ever tell you about it.

Our ability to connect lies in our willingness to be seen in all our authenticity.


Laughter is a lot like happiness. You can’t be commanded to be happy, nor can you be commanded to laugh. “LAUGH or you’re grounded!” It just doesn’t work.

I’m convinced that laughter is the key to success (or at least my definition of success).
Laughter means you’re deeply present in the here and now, and that is always the surest path to happiness.

Every great story is told in the now. A big part of the art of storytelling is merging the past with the now to have some kind of effect on the future.

Did you know that children laugh on average 300 times a day? Adults, on the other hand, only manage to laugh 5 times a day. That’s great for the kids, and rather sad for the adults.

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People want added value from your stories, so find ways to add value. Bring clarity to an idea. And while you’re at it, make sure your story answers the question your audience is thinking: “What’s in it for me?”


I walked right up to her, which put me about half-a-foot away, and her personal space alarms were clearly sounding a loud warning message. It was dark and the music was blaring. I was asking her to dance, but she couldn’t hear me!

I can guess what was probably going through her mind: Something to the effect of “Why is this creep so close to me?”

Dancing and storytelling are surprisingly similar. You have to know not only how to start a story, but when to tell a story in the first place.

And when you are telling a story, you also need to know when to speed up and when to slow down. That’s what I mean by tempo.

A big part of the magic that can happen in storytelling lies somewhere in-between those moments of speeding up and slowing down.

It’s hard to explain, so you just have to feel it.


Have you heard of mirror neurons? This is a fairly new scientific discovery revealing new insights on a daily basis.

You see a person trip and fall and your own body simultaneously clenches up as if you yourself had tripped, or the rush you feel watching something amazing happening on the field at a sporting event. Both cases are examples of mirror neurons in action – exploding in your body like fireworks on Independence Day!

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The lesson is simple: You get what you give. Give people your passion and you’ll get passion back from them. 

It’s that simple.

Love & Death

Two universal factors that contribute to all beauty are love and death. One of them no one has eluded, while the other is something many will die for. It behooves you to work them into your story (in an authentic way, of course).

The Last Class

Always end with a twist. The last thing in your story is what people will remember most!

This article in 29 words: Remove the mask and show the real you. The key to storytelling is caring. People will only listen to those they care about. Give them a reason to care. 

If you have a story to tell, a message to share, or value to deliver, do it! The world needs more of this. Don’t wait another day to tell your story.

Tom became an entrepreneur after leaving college (Penn State). He is the author of “How to Find Your Passion: 10 Simple Steps to Living A Purpose Driven Life.” Today he owns and runs businesses in publishing, Self Publishing System, a course where you learn how to write and publish a book in 3 months or less. Even with limited time, no writing skills, or clue where to start. Visit, where you can learn to craft your story into a book from which the whole world will benefit!

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.