Storytelling to Success by Author & Master Storyteller, Jarie Bolander


How can storytelling lead you to success as a founder? There’s no better person to ask than Jarie Bolander, who has published six books and believes firmly in the power of storytelling. His latest book, The Entrepreneur Ethos, details how to build a more ethical, inclusive and resilient entrepreneur community. 

Get Your Message Out Into the World

Every entrepreneur has a goal of getting their message out into the world and above the din of noise. As humans, we’ve told stories since the dawn of time. Stories have taught us, warned us, supported us and propelled us farther. These days, it’s not about who has the best product or service — it’s about who has the best story. 

Stories Have Structure

You may not realize it, but every story has structure. Whatever you’re selling, it’s important to realize that you’re not actually selling the thing, but rather the story behind it. As entrepreneurs, all too often we fall into the trap of focusing on the technology, “this cloud-based SaaS that’s powered by X, Y and Z” is utterly meaningless because every product presented this way sounds exactly the same. It’s boring. 

The whole point of storytelling is to tell your story to someone, and get that person to tell that story to someone else. It has to have structure and simplicity.

This isn’t just something that was pulled out of thin air — it actually has a basis. Joseph Campbell’s book The Hero with a Thousand Faces, published in 1949, looked at mythology in order to formulate the monomyth or the Hero’s Journey story structure. Mythology has been how we passed down stories for centuries. Old wives tales, superstitions and the like might have had a grain of truth to them at one time, but most of the time, they’re embellished precisely so that we’ll remember them. And this is where the Hero’s Journey comes into play. 

The Hero’s Journey

The hero’s journey starts off on a quest or call to adventure – to bring something: an elixir, knowledge or what have you, to his tribe or his kingdom. From an entrepreneurial level, you can look at this as if you are bringing people along with you on this journey. There’s a difference though, and that it is that most people believe that they are the hero of the story. 

If you’re trying to get customers or investors, you want them to be the focus of this tale. They have to be able to picture themselves as an integral part of your story.

The Virgin’s Promise

Another common story doesn’t even involve leaving your tribe or kingdom to go on a quest. It can happen right in your own little ecosystem. This involves making a difference in the world right where you are by developing your gifts and then revealing them to the world where occasionally you are the hero of the story. The boxing movie Rocky is a great example of this.

The Six Types of Story

You can break each story down into six distinctive types:

  1. Rags to riches (someone rises from nothing to become something)
  2. Riches to rags (someone has everything and then loses it all)
  3. Man in a hole (someone falls and then rises to triumph)
  4. Icarus (someone rises and then falls)
  5. Cinderella (they rise, then fall, then rise again
  6. Oedipus (they fall, then rise, then fall again)

As you analyze stories and movies, you’ll see this play out time and time again.

Stories are hard-wired into our DNA as humans. We love stories, because they force us to break out of the status quo and challenge ourselves to do and become something different.

The Three Parts of a Story

In addition to the different types of stories, there are also three different parts of a story:

  1. The beginning hook
  2. The middle build
  3. The ending payoff 

There can be stories where there are lots of rises and falls, but from a business perspective, you want there to be lots of twists and turns, like a roller coaster, to keep people engaged and involved. 

Most importantly, you want them to be on your team.

You want them to help you win, and to see themselves as heroes in your story. The way to do that is to be sure that your story meshes with the rest of the world. Here’s how…

Understand the Trends

Have a finger on the pulse of trends and what’s happening in the world around you. That means subscribing to trusted sources, like Founder’s Network, The Hustle, CBInsights, HARO, and The Knowledge Project. With telling stories, pitching and marketing – timing is everything. News cycles are less than a day now which means that it might seem like no one is hearing your story.

It can also mean that you have to tell it and refine it. Just like telling a story around a campfire, you might start out with a few listeners, but gradually, you will pique the interest of those around you. So how can you make sure that your pitch is heard? Let’s imagine that you want to pitch a reporter and tell your story so that they, in turn, will tell others. What do you do? 

How to Pitch a Reporter

Reporters, just like anyone else, are inundated with stories. You might be surprised to learn that reporters love talking to company founders.

  • Respect their time: it’s best to contact them Tuesday through Thursday morning
  • Be brief: No more than three paragraphs
  • Get your story straight: ask for something specific
  • Make it about them: do your research
  • Give them exclusives: everyone wants to be special
  • Follow up with them: it might take 3-5 times to  be successful. 

Writing Your PR Narrative for Fun and Profit

What is a narrative? Essentially it’s the art of telling a story. Then what is a PR narrative? The art of telling your story to many, many people. Everyone is unique and everyone has a gift. With that in mind, some people have better luck than others sharing what their gift is. 

Your narrative has to be clear, concise, compelling. It also has to avoid the use of buzzwords like “next gen”, “SaaS”, “data mining”and all of those other terms that get scattered in to make a launch sound more important. In short, you want your grandmother to be able to tell her friend what it is that you do, and what your story is. 

Grab Some Paper and Create Your Narrative Right Now

1. First, write 1-2 sentences. Why does your business exist? Pick a word, just one word, that describes it. Take a few minutes to brainstorm and think about it. Consider Chubbies. It’s a clothing company that exists to bring you the best weekend clothing that has ever been conceived. It’s a simple yet powerful why.

2. How is your business unique? Write 1-2 sentences and then pick a specific word. Remember, uniqueness is how we get above the noise. Case in point: the Impossible Burger. The Impossible Burger is made with meatless meat — meat that has been grown in a lab rather than harvested from animals.In short, fake beef that looks and tastes real. Simple, yet powerful. If you’re a vegetarian and want a burger, this could be an option for you to consider because it fits within the narrative of “Impossible”. 

3. What pain does your business solve? Write a couple sentences and then pick a word that describes it. Consider Lyft as an example. What’s unique about Lyft? It solves a huge pain — getting a cab sucks! Everyone has experienced it. They solve that pain.

Great Examples of Company Storylines

  • Hyperloop is a new way to move people and things at airline speeds for the price of a bus ticket. 
  • The Hustle is a media company on a mission to inspire, educate and entertain an entire generation of people
  • Prolon: The Fasting Mimicking Diet gives you all the benefits of a 5-day fast…while enjoying food. Rejuvenate. Regenerate. Revive.
  • is mobilizing young people in every U.S. area code and in 131 countries. Sign up for a volunteer, social change, or civic action campaign to make real-world impact on a cause you care about. 

When you read these, you automatically think – tell me more, tell me how? They’ve got you hooked, they’ve built up the middle part, and the end result — the payoff.

Now that you’ve learned exactly how to structure your story and how to write a thrilling narrative, along with plenty of examples, the ball is in your court. Take time now to pull together each of these pieces and write your own narrative. Be the storyteller of your own success!  


Share With Your Network

Looking for startup advice, connections, and insights?

Tap into a global network that enables you to answer questions, build relationships, and gain the perspective you need to move faster.
Peer mentorship with fellow tech founders
Pitch practice with Tier 1 VCs
Accelerator grade discounts