Become a Storytelling Icon

How to climb the 3 levels of storytelling mastery

September 5, 2022
min read

Welcome Back, founders and storytellers.

Do you feel it?

Change is here.

VCs are back from their summer long vacations. The weather is cooling. It's that time of year when the post Labor Day fundraising sprints pop off.

Like Bruce Buffer says before world championship UFC matches...


Because of that, this week we are diving deep into the 3 levels of storytelling mastery. If you can tell a great story, you can fundraise. Simple as that.

Let's do this thing.

DEEP DIVE: Climbing the 3 Levels of Storytelling

You already know how much I adore Steve Jobs. He is by far one of the most influential CEOs of all time, shaping the way we interact with the world. If it wasn’t for his vision, we’d still be carrying around those giant folders of CDs.

But there's a part of Jobs that’s sometimes overlooked: not only did he change society through technological innovation—he revolutionized the way products were sold.

For YEARS, I’d look forward to the annual Apple WWDC keynote, eager to see what new products Jobs would roll out. I’ve never worked in the tech industry, yet there I was, watching a two-hour presentation meant for techies. And I’m not alone. Even though Jobs passed away in 2011, MILLIONS of people still watch Apple keynotes live. According to StreamsCharts, 2.7 million tuned in live to watch Tim Cook roll out the iPhone 13 in 2021. That’s more than the average viewership of WWE Smackdown. How insane is it that people are watching a developers conference as a form of entertainment?

Over the years, other companies have tried to do the same by hosting their own special keynote events, but few have come close to capturing hearts, minds—and wallets—the way Apple is able to. Why? What made Jobs and Apple so unique?

If you’re reading this newsletter, the answer probably won’t shock you. It’s storytelling.

Just go watch the 2007 keynote when he introduced the iPhone. He uses silence and a ridiculously powerful hook at the beginning. He leans into a rule of 3 and misdirection. He perfectly executes an old world versus new world strategic narrative structure. (I might even do a full newsletter on his brilliance in this keynote and some of his others).

Steve Jobs was one of the most powerful storytellers of all time. This talent translated not only into the way he positioned Apple in the marketplace, but the way he was able to grow a little animation studio called Pixar into a Disney-slayer.

Jobs understood the importance of storytelling, as evidenced from his famous line: “The most powerful person in the world is the storyteller. The storyteller sets the vision, values, and agenda of an entire generation that is to come.”

My goal with each and every one of the founders I coach is to get them to Jobs-level storytelling abilities, but it’s not easy. Just like summiting Mount Everest isn’t for everyone, neither is climbing to the peak of Storytelling Mountain.

Over the years, I’ve discovered there are three levels of storytelling. Below, I’ll share each one—and ways to reach the top of your storytelling game.

Level 1: Knowing WHAT to Say

Humans are wired to be storytellers—it’s the primary way we share information and connect with others. But just because the impulse is in our DNA doesn’t mean everyone’s born with the skills necessary to do it effectively. The reason most kids’ stories are unbearable is that they haven’t yet learned which details are relevant to their story’s arc and which are extraneous. And while some people get better at storytelling as they grow up, some do not.

Knowing what to say is all about getting the content right. It’s the Goldilocks rule: not too much, not too little, but just right.

In the beginning stages of learning how to tell stories, we often think every detail and factoid is precious. But the best storytellers know that often, less is more. Think about Neil Armstrong in 1969. He was able to encapsulate the entire majesty of landing on the freaking moon in just 11 words: “That’s one small step for man, one giant leap for mankind.”

Or what about Abraham Lincoln, whose 1863 Gettysburg Address lasted all of two minutes. (Fun fact: this speech echoes a much earlier speech from The History of the Peloponnesian War by Thucydides. In Pericles' Funeral Oration there are similar themes and structures as in the Gettysburg Address. I point all this out to remind you that great artists borrow, remix, and find inspiration in many places).

Lincoln’s speech was preceded that day by former Harvard dean and renowned orator Edward Everett, who spoke for over two hours. Unless you’re a real history buff, I doubt you’ve even heard of him.

Good Level 1 storytellers are great distillers—they know exactly how to sizzle a story down to its essence. In his book On Writing: A Memoir of the Craft, horror novelist Stephen King shares an excellent revision formula: “Second Draft = First Draft - 10%. This premise of trimming the fat is echoed in English author Sir Arthur Quiller-Couch’s famous advice: “Murder your darlings.”

One of my good friends, Justin Mikolay, was the speech writer and comms director for General Petraeus and General Mattis. He would often find himself editing and re-working a speech 10 times. One of his quotes has always stuck with me around how to get the "what" right...

Preparation creates precision.

Level 2: Knowing HOW to Say it

Some of the world’s best storytellers will forever be trapped at Level 1 because even though they know how to masterfully craft a story, they cannot make it come alive. This is the second level of storytelling—HOW to say it. This is where things like tone, pacing, volume, and musicality come into play.

Take a look at the difference between these two sentences:

we’re in trouble.

We’re in TROUBLE!!!!!!

The words are exactly the same, but the phrasing changes the message being conveyed. Accenting the TROUBLE in the second sentence demonstrates a sense of urgency and fear not present in sentence 1.

Great storytellers can use Level 2 delivery tactics to manipulate their audience. In his “Finest Hour” speech, Winston Churchill used a slow, measured pace to convey calm and confidence to the British people in the face of Nazi bombardment. Martin Luther King, Jr. employed the musicality of Shakespeare and Southern preachers to compel his audience to action. And though he’s clearly not an ideological role model, Adolf Hitler spent hours practicing his facial expressions and gestures before speeches so he could whip his audience into a frenzy.

If you really want to see a master at work, look no further than Mr. Fred Rogers. Most of us grew up listening to his soft-spoken tones teaching us how to tie our shoes and be good neighbors. That guy’s demeanor is like a verbal hug—no matter what, you know everything is going to be okay.

Two other great places to see the "how" in action: Comedians and Rappers.

One of my favorites is Trevor Noah because of how he uses different voices. The other day I was listening to him talk about how he learns the accents. He said, "language is really about rhythm."

Without rhythm, a story will sound boring.

With rhythm, it sounds like music. And music sticks with people and moves them.

Level 3: Knowing how to FEEL the story

I’ve talked in previous issues about how an effective storyteller can actually sync their brain waves with their audience. That’s what’s happening when you get so engrossed with a story that your surroundings melt away.

At this highest level, you’re actually creating change within the brain, carving neural pathways that didn’t previously exist. The listener adjusts what they’re thinking and feeling at the same time.

The name of the game here is authenticity and vulnerability. The story isn’t just a story—it’s REAL. In order to get to this place, you must remove the mask you usually wear in the world and let your audience see who you really are—warts and all.

I’ll be honest with you: no matter how hard you work on your storytelling skills, you might never achieve this final level. There’s a level of talent needed to get to this stage that simply can’t be taught. It’s the X factor—the je ne sais quoi—that separates the great storytellers from the truly elite.

I’m saying this not to discourage you, but to set realistic expectations of your storytelling journey. A basketball player can practice thousands of hours and never become Michael Jordan, but that doesn’t mean they’re unsuccessful. I’m also not saying you can’t get there, but there’s only one way to find out: Master levels 1 and 2.

Storytelling is both an art and a science. It’s a science to learn what to do and how to say it, but level 3 storytellers are artists. There’s an evolution to it, which is why the world’s best storytellers have a massive advantage.

If you really want to become the next Steve Jobs, you have to start climbing the mountain.

The views will change your life.

RESOURCES for Founders and Storytellers

Most stand-up comedians are also fantastic Level 2 storytellers. They have to know how to shape their stories so it keeps the audience engaged and laughing. On this episode of Good One: A Podcast About Jokes, comedian Bert Kreischer discusses the evolution of his most famous bit, “The Machine” and how it rocketed him to stardom. A good deal of the show is devoted to Kreisher’s Level 1 storytelling revisions, deciding which elements he should tell and which darlings he needed to murder.

As I mentioned earlier, Fred Rogers captured the hearts and minds of millions of children over the course of his career, welcoming them into his home and asking them to be his neighbor. But Rogers didn’t just use his speaking abilities to inspire kids—he had the same success with adults, including in the late 1960s, when he petitioned Congress to fund public television. This short documentary breaks down how Rogers used the three tenets of persuasion—ethos, pathos, and logos—to get his funding.

VCs have been going crazy for blockchain tech over the last year or so, but Q3 data from Crunchbase and PitchBook suggests investment in blockchain-focused startups may be slowing. While companies have received around $10 billion in funding in recent quarters, the total dollar value of web3 investments could be cut in more than half in the coming quarters. It’ll be interesting to see if this trend continues, or if it’s just a part of the rapid business cycle associated with this type of business and continue this boom/bust pattern over time.

A founder asked me to share this anonymous survey around if founders have ever gone through coaching or therapy. Mental health is a huge issue inside of the founder community. I already took the survey (it takes 4 minutes) and hope a few of you can help out too.


What a beautiful tribute video from Nike to Serena Williams. An absolute legend and the epitome of greatness.

This line to finish the ad is pure class.

"By changing nothing, she changed everything."

That's the power of words.

See you next week.

I work with a small handful of founders to coach them through their fundraising and storytelling. We are highly selective and not cheap to work with. The only metric we care about is founders successfully fundraising. If you're interested to apply as a venture backed seed or later stage company, you can at the Founder Fundraising Program.

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