How entrepreneurs can tell stories that sell
My name is Elaine Ramirez. Several years ago, I had the privilege of taking the helm of a magazine in South Korea called Groove.
It was the hardest but most rewarding experience of my career as a journalist, because we surfaced important social issues that the mainstream media didn’t cover. I also found my footing as a leader when I brought a group of talented people together to do valuable work. But as advertising stopped coming in, I felt helpless as the magazine failed.
After I left, I began writing about startups and tech entrepreneurs, who inspired me to take risks and learn from failure. That’s why I’m studying media innovation and entrepreneurship at Northwestern University, where I’m building the tools and networks I’ll need to one day successfully lead a media company that creates impact.
That’s me, as of today, in a 60-second story. (And when I graduate in a month, I’ll need to tweak it.) I’ve always found it awkward to talk about myself, but as a media entrepreneur-in-training, I’ve learned that storytelling as a sales technique is crucial.
The stigma of selling
The word “selling” often earns a negative connotation thanks to imagery of hoodwinking car salesmen or real estate agents. But every product, every service and even every vision, from a chat app to a political movement, needs to sell to succeed.
There’s a double standard, then, when it comes to entrepreneurs. They sometimes earn an inflated heroic image for pursuing their dreams, taking risks and leaving no stone unturned to succeed. Naturally, that requires selling. But for an entrepreneur, it’s more than selling a product or service you build from scratch: You sell your vision, your values and yourself. Selling becomes less of a transaction and more of a two-way empathetic conversation between buyer and seller to understand each other’s needs and how to fulfill them.
There may be no greater tool to create that personal connection than storytelling. Stories do not exist only to fill time and entertain. Facts are neutral until people put meaning to them; then they become stories, which can increase empathy between people who may be worlds apart by illustrating our shared humanity. They help us make sense of the world, with all its tragedies and joys, by creating meaning, which is the driver of emotion. Stories encourage people to cooperate and motivate generosity between strangers. They can create value and have the power to change minds when they help people reach common ground.
Selling becomes less of a transaction and more of a two-way empathetic conversation between buyer and seller to understand each other’s needs and how to fulfill them.
As a journalist, I have spent my career working to tell stories that move people and inspire change. And on some level, entrepreneurs, too, help people make sense of the world and move them to act.
Storytelling for entrepreneurial selling
That’s all according to Andrew Sykes from Habits at Work and Craig Wortmann from Sales Engine, two professors at Northwestern University’s Kellogg School of Management who recently delivered a lecture on entrepreneurial storytelling.
In the world’s simplest story line, something ordinary happens, then something extraordinary happens to change everything. Then there’s a new world that emerges because of it. There’s a technique to use this framework as a three-act entrepreneurial story arc.
In the ordinary act of the story, before something pivotal happens, you can establish credibility with self-deprecating humor, giving you the opportunity to show off your humor while establishing your credentials.
In the extraordinary act, consider what you realized or decided. Showcase your passion and commitment that prefaces why you’re doing what you do.
In the new world act, explain what is so meaningful about your work and what impact you hope to have.
By the end, the listener should understand not only the product you’re selling, but also the values and context that inspired you to take this leap. That makes your story not only more convincing, but also more memorable.
Measuring the risks and benefits of stories
Entrepreneurs have the gift of a natural story — they are by definition heroes in a struggle. Sykes and Wortmann say entrepreneurs can employ four types of stories to engage clients, investors and employees:
- Success
- Failure
- Fun
- Legend
Each type of story carries a benefit and a risk.
Success stories inspire and motivate, such as personal or company origin stories that showcase a person’s mission, values and vision. They allow room to humble-brag, but they risk displaying arrogance.
Failure stories show vulnerability, but risk losing people’s faith in your abilities and direction.
In the end, people want to be entertained. Fun stories lighten the mood and intensity, and are important when people need to feel good about themselves. But with too many fun stories, people might not take you seriously.
Legends are the rarest of the four, and the most epic success stories may become legend.
The great thing about this framework is that every story can be adapted to different categories. These lessons motivated me to reflect on the successes and (many) failures of my life and career. I believed for a long time that leaving Groove magazine was a story of my greatest failure, but I decided to turn it into my greatest success and, who knows, perhaps one chapter of a legend. By intentionally sharpening my story as a selling technique, I can use it as a tool to convey context to my values and goals as a media entrepreneur.
The right story at the right time
Sykes and Wortmann suggest that every entrepreneur develop stories of each type for their toolkit, each with a moral or takeaway. Using a matrix framework (below), we can learn to capture and tell the right stories at the right time, for the right reason. (Wortmann believes so strongly in this framework that his company is developing an app called Story Matrix to help entrepreneurs and sellers to shape and organize their stories.)
Each story should carry an arc: Context that pulls you in immediately, conflict that steadily builds a compelling argument, a climax that illustrates a clear high point, and closure that points the way to action.
Just as important as the chronological business arc is the emotional arc, which is where the empathetic connection between storyteller and listener is formed. The emotional arc allows you as the storyteller to modify the type of story you’re telling with the same information, turning a tragic failure into a fun tale or eventual success story.
Sykes and Wortmann must have told over 30 stories in three hours to illustrate their point. Of them all, I will long remember the founding story of PrettyLitter. (I am, admittedly, a cat person.)
Daniel Rotman just wanted answers to why his young cat suddenly died. After three years of researching and understanding the animal, he realized what stoic creatures they were. While dogs show their emotions clearly, cats will never let you know when something is wrong.
So Rotman went to work on developing a litter that would detect through the feline’s urine whether the animal is sick. It changes colors when a disease is detected to alert the pet owner, potentially saving the animal’s life. The litter uses lightweight silica gel mined in China, and Rotman, at the time of telling Wortmann this story, was seeking funding to create a new manufacturing and distribution network. The story, on top of sound business fundamentals, is apparently effective: Founded in 2015, PrettyLitter has three funding rounds to date.
Look for stories everywhere — in news articles you read and in your conversations with others. Sykes suggests to collect them, curate them and categorize them into a story matrix to use as your own.
In the end, Sykes says, telling a story is about creating connections and inspiring impact. Use stories to change minds, to move people, and to create the future you desire.
