The key to storytelling for results

How to boost emotion and increase connection

March 19, 2023
min read

Greetings, Chief Storytelling Officers.

This week saw a 16 seed defeat a number 1 seed in the first round of the NCAA Men's Basketball Tournament. One thing really stood out.

The head coach for FDU (16 seed) told his players before the game that "the more I watch Purdue (1 seed), the more I think we can beat them."

They did exactly that. Belief makes anything possible.

Believe in yourself. Believe in your dream.

Believe that you can do it.


DEEP DIVE: Getting Heavy

There’s a scene in Back To The Future where Michael J. Fox’s character Marty is trying to wrap his head around time travel’s implications on future events.

“Woah, this is heavy,” he says, applying the perfect ‘80s teen affectation.

“There’s that word again, ‘heavy,’” the 1955 version of Doc replies. “Why are things so heavy in the future? Is there something wrong with the earth’s gravitational pull?”

Here in our present, we’ve come to understand the cultural meaning of the word heavy. We use it when describing heavy metal music, the kind characterized by brutal guitar riffs and crushing vocals. Others use “heavy” to indicate someone is carrying a firearm, a synonym for being “strapped.”

In any of the above connotations, the meaning is clear: heavy is serious, raw, real.

We often think about heavy as being somber or dark, and while it certainly can be, that’s not always the case. Heavy can be comforting as well—the hug Danny Tanner gives DJ and Stephanie at the end of a particularly poignant scene on Full House. Or, more literally, the heaviness of a weighted blanket, which research has demonstrated has therapeutic effects on stress and forms of ADHD.

So what can heaviness do for you, the storytelling founder?

I’ve talked in the past about the importance of emotion in storytelling. We like to pretend we make big decisions—say, investing millions of dollars in a budding startup—on logic, but that’s rarely the case. Far more often, we make decisions based on emotion, and we justify our decisions with logic. This is exactly why buyer’s remorse is a thing—we purchase something because of the way it makes us feel in the moment and regret it later when we can’t find logic to support the purchase.

When pitching a potential investor on your company, you can leverage this psychological inclination to tip the scales in your favor.

You can get heavy.

Heaviness is that moment when somebody hears a story and says, “wow, that was powerful.” Or they might say, “that founder won’t ever stop.” It can be the difference between a mediocre pitch that leaves investors on the fence and a powerhouse pitch that compels them to move heaven and earth to sign you.

You can absolutely use weight to transform your pitch, but a word of warning: There’s an element of knowhow and finesse required in order to use emotion correctly. I often see founders who try to make their stories “emotional” by over-indexing sadness or humor, thinking it is the secret to creating a connection. It doesn’t work that way. Heaviness can’t just be shoehorned in.

Few would argue that award-winning humor writer David Sedaris doesn’t know how to get a laugh. But by Sedaris’s own admission, his initial work was funny but lacked weight. “I look at some of my earlier writing, and I just see someone who’s so desperate for a laugh,” Sedaris says in his MasterClass. “And then after a while, I thought ‘well, okay, I know I know how to do that. What if I try for something more? What if I try to move people in a way? What if I try to engage them?”

While Sedaris’s more recent work still retains his signature wry observations and snark, the topics he’s tackled have significantly more weight—things like school shootings, navigating the dynamics of an aging parent, and his sister’s suicide.

How do you get heavy? Here are two ways to start.

Adjust your Diction

Diction is one of those fancy words you learn in English class and promptly forget, but when it comes to storytelling, it’s an incredible weapon to have in your arsenal.

Simply put, diction is your word choice, the understanding that the words you attach to your ideas affect the tone and mood of your story.

One major element of diction is speaking your audience’s language. I, for example, use the word y’all with Texans to show I was one of them. That’s actually part of my identity, so it’s authentic. Using y’all on purpose connects me to my audience. Or, if you’re speaking to surfers, you might use “dude” or “bro.” Depending on your industry, you might refer to a business owner as a founder, an entrepreneur, or a creator.

Using someone’s own terminology has an immediate positive effect. People expect to hear their in-culture members speak a certain way. Using your audience’s language signals that to them.

The goal here isn’t to be fake. If you’re from the Bronx and start throwing around a bunch of y’alls, it’s going to have the opposite effect. It’s all about expressing a part of yourself that your audience will embrace.

This is where it gets heavy. Diction goes beyond your persona. You need to choose words that will have impact when they’re delivered.

When I tell people to choose their words for impact, most often they begin peppering their sentences with adjectives and adverbs. Believe it or not, this has the OPPOSITE effect on your story.

Every time you find yourself using an adverb, replace it with a stronger action verb instead. Strong action verbs will ALWAYS make a bigger splash than a weak verb and an adverb.

Consider these examples. Which choice carries the most weight?

He walked confidently to the front of the room. He strode to the front of the room.

She loudly banged her fist on the table. She slammed her fist on the table.

They completely broke the sales record. They obliterated the sales record.

Action words are best because they give more weight to the meaning. Set the scene with sensory details and important emotional information. If your audience can FEEL your story, you’ve won them over.

Use the Emotional Storytelling Structure

Heaviness in a story comes out in different ways. That’s why it’s both challenging and beautiful.

While adjusting your diction is a good first step, another more advanced method of adding weight is structuring your story in an emotional way. It’s what I call the Emotional Storytelling structure. The genius of this structure is that you leave the details open-ended so the audience fills in the blanks with their imagination. You make the future vision so compelling that the audience does the work for you. You turn the unknown—an inherently scary and uncertain space—into a strength.

But executing a story like this is easier said than done, as the majority of the stories we tell on a daily basis follow what I call a Logical story structure. In Logical Storytelling, one event begets another in a logical way. The Hero’s Journey, a story structure popularized by Joseph Campbell, is a great example of Logical Storytelling. It’s the structure that sagas like Star Wars and Harry Potter follow closely, as well as just about every superhero movie you’ve ever seen.

If Logical Storytelling is like cooking an entree using a recipe, Emotional Storytelling is like crafting a dish the way a Michelin Star chef would. There are no measurements, no instructions—just feel. In this way, Emotional Storytelling is an art, not a science.

As such, teaching Emotional Storytelling is a double-edged sword. I can’t just send you a list of bullet points that you can implement into your upcoming pitch. The only way I can convey this structure is to show you how it’s used.

An incredible example of Emotional Storytelling comes courtesy of Tim Westergren, the founder of Pandora. In the early days, Westergren found himself unable to pay his employees. Their funding was running out, and they weren’t anywhere close to making money. At that point, they hadn’t even LAUNCHED their product.

Westergren needed a Hail Mary, and he found it in Emotional Storytelling.

“We all know here that what we have created is unique, and it’s solving a gigantic problem,” he told his team in a now famous speech. “No one on earth is going to do what we’ve done, and when you use this product, we all know how magical it is. It will find its home.

“Everybody on the planet loves music,” he continued. “There are millions of musicians who produce great music, and they can’t find each other. When this thing finally finds its home, it’s going to change culture. And how many times in your life do you have a chance to do that?”

The 50 Pandora employees gave Westergren a standing ovation. He didn’t say anything that was logical, didn’t lay out a step-by-step plan for how he’d get his sinking ship to float. He focused on the once-in-a-lifetime opportunity to fundamentally change the culture’s fabric.

That’s inspiring. That’s motivating. That’s company saving.

Because of his emotional portrayal of the future, Pandora employees deferred their salaries for TWO YEARS. Their gamble paid off, of course. Pandora went on to become hugely successful, and in 2019, sold for $3.5 billion.

At the end of the day, the only real way to tell stories with weight is practice and dedication. There are no quick fixes when it comes to becoming a world-class storyteller; You must fail and reflect, revise, and give it another go.

Find a trusted colleague—a friend, co-worker, coach, etc—who can become your test audience. This person must be willing to give you the tough, honest feedback on your story. As you practice your story, pay attention to when they’re really engaged—non-verbal cues like intense eye contact, or leaning toward you. That’s when you’ve got them, when their outer world melts away and they’re enveloped by the weight of your story.

Those moments are the ones that will make the difference in your pitches. They’ll solidify your audience’s belief that you are the founder to bring them to the Promised Land. They’ll make your audience sit up, pay attention, and leave your meeting going, “woah, heavy.”

RESOURCES for Founders and Storytellers

This is the second time that I’ve mentioned David Sedaris’s Masterclass in an issue of The Storyteller’s Playbook, and if you’ve already got a Masterclass subscription, it’s definitely worthwhile to check out. The 14-part course walks you through each step of Sedaris’s storytelling process, including structure, revision, and the musicality of language.

When you're leaning into emotional storytelling, one additional tactic to help you is what I call the Phase Approach. This keeps things big picture but provides a roadmap without getting into step by step logical storytelling. You can learn more here.


The story we tell ourselves is the most powerful story in our lives. If you're reading this, there are plenty of chapters ahead for you to write. Make it an epic tale of triumph.

See you next week.

P.S. Each week I post multiple videos on YouTube focused on storytelling and fundraising. Subscribe to keep up to date!

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