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  • Writer's pictureJohn Washington

Four Ways Storytelling Empowers Entrepreneurs - Takeaways from the Business of Software Conference

Nick and John attend the 2023 Business of Software conference in Raleigh, NC.
Nick and John attend the 2023 Business of Software conference in Raleigh, NC.

Once Upon a Time

When was the last time you were on the receiving end of a good story? The story may have been relayed to you via a book, a movie, a discussion over coffee, or, in my case, by a speaker at a conference. How did the story impact you? What message did you walk away with, or what emotion did you feel as a result of the story?

This past week in Raleigh, NC we had the pleasure of attending the Business of Software conference, a single track conference for operators of, you guessed it, software companies. The three day event included a robust lineup of speakers covering a wide range of subjects, such as forming defensible business strategy, building an enterprise sales process, navigating acquisitions as a seller, and how to price software.

Business of Software 2023 - April Dunford presents on differentiated value in a sales pitch.
Business of Software 2023 - April Dunford presents on creating differentiated value in a sales pitch.

But the topic that left the greatest impression wasn’t one that is commonly thought of as an arrow in the quiver of the entrepreneur. Instead, it’s a topic that is more closely associated with campfires, movie theaters, and rehashing memories with friends. That topic is the power of stories.

Jamie Woolf, who spent ten years with Pixar, and Christopher Bell, a screenwriter and professor of media studies, articulated the power of stories during a compelling hour-long presentation. As it turns out, stories not only have a place in the quiver of the entrepreneur, stories may be the most important arrow a business person can deploy from that quiver.

50% of The Time, Humans Pay Attention Every Time

The human brain has limitations, especially when it comes to attention span. When we want to learn and store information in long-term memory, we must force ourselves to focus on the topic at hand. In today’s environment of rapidly replenished information and easily consumable media, we face a constant barrage of demand for our attention. By some estimates, the human brain spends up to half of its awake hours wandering, searching for a reward that’s deemed to be sufficient. Until the mind finds that sufficient reward, it flutters from thought to thought.

How can we limit distraction on the quest to find the best in-the-moment reward? By forming an emotional connection with a thought, an idea, or a story. Consider a time that you’ve been lost in a great story. Now recall the strength of connection to the characters, the narrative, or the excitement associated with uncovering what comes next. Storytelling is an effective way to momentarily limit the mind’s sauntering and to create an emotional connection between listeners and a storyteller.

Woolf and Bell, the Business of Software presenters, shared that mirror neurons, a special class of neurons that activate during stories, are a key reason that we connect with a well crafted narrative. When these neurons are active, as they are during a good story, we connect with the characters in the story in greater depth because we mirror the characters’ emotions. We feel sadness when the protagonist struggles, we feel happy when the protagonist succeeds, and we feel motivated when the protagonist overcomes challenges.

In those moments of strong connection, we forgo the desire to seek a new mental reward and we immerse ourselves in the story at hand. In a follow up post we’ll share the framework that Woolf and Bell provided for crafting a compelling story arc. But for now, let’s explore four ways that 37th & Moss believes entrepreneurs can use storytelling to form deep connections with customers, investors and teams.

Business of Software conference attendees networking after the second day of presentations.
Conference attendees networking after the second day of presentations.

Four Ways Storytelling Can Benefit Entrepreneurs

1. Acquiring New Customers or Channel Partners

Although touting your company’s capabilities, product price point, or track record for success may seem like a logical talk track in a sales presentation, we’d venture to say that the recipient of these facts is likely not retaining this information at a depth that bodes well for their championing your product or company internally to their team.

Rather than spouting off facts about your product and how capable it is, which we’d submit leads to audience mind wandering and therefore low retention of information, can you wrap a story around your company’s “why” to establish a meaningful connection with your audience? In doing so, your narrative may stand out relative to that of competitors by forming a connection between you and your listener. The more meaningful the connection, the more likely follow on conversations will have high levels of productivity.

Dollar Shave Club’s story, as told by founder Michael Dubin, is a great example of successful customer acquisition through storytelling. Dubin launched Dollar Shave Club in 2012 with much fanfare, thanks in large part to the video linked above. According to Bloomberg, by 2016 the company is reported to have generated $200 million in annual sales. Great story, great outcome.

2. Raising Capital or Exploring a Company Sale

Investors are notoriously busy people who are inundated with pitches and preoccupied by important commitments to portfolio companies. The challenge of standing out among the myriad of decks and investor time constraints is real, especially among early stage businesses for which traction has yet to point to a breakaway success.

In our experience, telling a clear and compelling story is key to completing a capital raise. Credibility is important in this context. Investors may be less likely to connect with a dramatic vision that culminates in the entrepreneur leading the company to spectacular heights. Doesn’t every entrepreneur believe they have a category defining idea that will generate millions of dollars in revenue by acquiring a paltry 1% of the market?

A more likely scenario is that an investor connects with a logical story that engenders trust, humility, determination, interest in a problem and an unwavering commitment to solving that problem. In the case of a pitch for a later stage business, using data to support your story is also a good idea because it lends credibility to claims of traction.

3. Motivating Employees and Teams

The benefits of storytelling are not limited to external use cases, such as sales or capital raising. Great company leaders are often also capable communicators who use stories to connect teams with a mission and a culture. Engaging and inspiring a team is critical for empowering a group to succeed. This is especially true today as remote work appears to be here to stay. Developing connections between team members who interact exclusively via digital channels is hard, and further emphasizes the need to facilitate connections that would otherwise be created via an in-person office setting.

Team alignment is another benefit that stories can have on a company. Teams that are aligned around a common goal are a formidable force. When rallying behind a shared cause, people tend to maintain high levels of focus and determination because the connection formed with the group creates loyalty. For example, stories about successful customer outcomes can be a great way to align teams by showing how a company shapes a positive result for users of the company’s product or service.

Some of the most productive cultures we have had the pleasure of contributing to are cultures that were built around stories of possibility. As individuals, it’s not uncommon to occasionally, or frequently, doubt our capabilities or our potential. Thus, teams can derive especially strong benefit from mirror neurons when connecting with stories that communicate capabilities and encourage healthy levels of confidence. As a leader of a business, you never know when a story about possibility pulls a team member out of a rut and inspires confidence.

Admiral William McRaven motivated the 2014 graduating class of his alma mater, The University of Texas, with this compelling story. To this day, we believe many beds are made each morning as a result of Admiral McRaven’s motivating speech.

4. Educating the World About Your Product

Capturing the attention of your ideal customer is hard, regardless of product type. There is no shortage of competition for consumer mindshare, and standing out relative to the droves of content and marketing messages that flood our daily lives is quite the challenge. Even if a company has capital to allocate towards high volumes of marketing messages, it’s worth exploring whether a lower volume approach that strives for an emotional connection with users would yield a higher return on spend.

Product education is particularly well suited for stories due to the ability to craft a protagonist that replicates an ideal customer. If research shows that your ideal customer faces a specific problem, creating a protagonist with patterns similar to those of the ideal customer is a great way to illustrate your product’s effectiveness while activating mirror neurons. In a world in which we’ve become immune to many marketing campaigns due to volume of messaging, stories can be used to craft a compelling narrative and may be key to differentiating your product.

Whether you’re sharing the story of an existing product or a new product, forming a bond with users by appealing to their unique needs or problems builds strong connections. Marketing messages that extend beyond the product and incorporate values or beliefs that are core to customers may enhance the impact of a story.

Steve Jobs’ 2007 presentation introducing the first iPhone is an example of a well crafted product story, and one that successfully captivated Apple’s ideal customer.

Practice, and Reflection, Makes Perfect

Christopher Bell ended his presentation at the Business of Software conference by sharing a three minute story about his life. At the story’s completion, Bell received an enthusiastic ovation from the audience. His story did exactly what he and Jamie Woolf said it would do. It created an emotional connection between Christopher and his listeners.

Of course, Christopher is an accomplished screenwriter with years of experience crafting stories. Easy for him to connect with his audience! But fittingly, the story detailed his initial struggles as a writer and the years of challenges he faced while trying to make a living telling stories. Chris has accumulated decades of moments that he effectively incorporates into a relatable and inspiring story.

Reflection is a key part of crafting stories. What moments can you capture, save, and craft into a great story? Understanding which components of your personal or professional life should make the cut for your stories is a challenging part of storytelling. Fortunately, we can start small by finding a welcoming audience, like a friend or relative, to bounce story ideas off of as we work to become proficient at the craft.

Although we don’t typically associate stories with strategic business tools, we should. Stories are perhaps one of the most powerful ways that humans can form connections. Whether the target audience is a prospective customer, an investor, your team, or a packed theater, stories are an impactful way to make a differentiated and emotional connection with an audience. Next time you’re on the receiving end of a good story, make note of the attributes that draw you to the story and the arc that the storyteller follows. With reflection and practice, you too can captivate an audience.

The Autbooks team shares the story of the implementation of Jobs to Be Done, a customer acquisition framework.
The Autbooks team shares the story of the implementation of Jobs to Be Done, a customer acquisition framework.



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