Don't be a basic...

How to craft your message so you'll stand out from the crowd

February 20, 2023
min read

Greetings, Chief Storytelling Officers.

I turned over the final manuscript to my editor this weekend and I'm so pumped to get the book out into the world in the coming months. This was one of the biggest projects of my life. I can guarantee you one thing, the book holds the key to becoming a world-class storyteller.

I'll be sharing more about the book as we get closer to release.

One quick note for those founders out there looking to raise. I had multiple founders I coach get term sheets this past week. The money is out there for great founders who know how to tell the winning story.

Let's dive in.


DEEP DIVE: Storytelling with Precision

I’ve got a question for you:

Why are you making your company sound so vanilla?

I know this is a bit harsh but I'm frustrated at what I'm seeing because it means the founders are going to struggle, their teams are going to suffer, and there's a high likelihood they fail to fundraise.

And this is across all stages. I'm seeing it from Seed all the way to Series C.

Let's get into why it's happening so you can make sure to do better.

A lot of it has to do with our psychology. At our core, we are tribal animals. Back when mastodons roamed the Earth, we needed to rely on our tribe to protect us from predators. If we stood out from the pack, we ran the risk of being cast out, thus lowering our chances of survival.

The best example of this tribalism manifested in a modern way is our allegiances to sports teams. Have you ever met a die hard Dallas Cowboys fan? They are devoted to the team on a primal level—despite the fact that, as Jerry Seinfeld once pointed out in a comedy bit, all they’re really rooting for is different-colored clothes.

Nowadays, there’s a pretty slim chance you’re going to be eaten by a saber-toothed tiger if you distance yourself from the pack, but that instinctual desire to fit in—that FEAR of being ostracized—is still firmly implanted in your brain.

So what happens? Rather than take a risk, you play it safe. You craft your founder story and model your pitch deck after all of the founders who have come before—and then you wonder why it’s rejected with the thousand others sitting in the slush pile.

I’m here to tell you that in order to get where you want to go—to get funding, to hit your sales goals, to change the world—you need to be bold. You need to be intriguing.

The Problem With The Apple Model

In 2018, Apple became the first publicly traded US company to hit a $1 trillion valuation. Since 2010, they’ve climbed to the top of almost every product vertical—smartphones, tablets, wearables, services. Until his death in 2011, Steve Jobs seemed to do no wrong. He was an entrepreneurial hero, forever emblazoned on the Mount Rushmore of tech.

That type of success inspired a whole generation of entrepreneurs to set out in search of their own greatness.

But for a generation that idolized Jobs, it’s crazy to see how few learned from him. Countless startups have dissected and repurposed Apple’s playbook, trying to capture that same magic for themselves. But they’ve all focused on the wrong elements.

The result? A sad facsimile of Apple’s branding, UX, and marketing. Check out this picture of a Microsoft retail store. Look familiar?

What about Tesla?

That’s not to say that Microsoft and Tesla aren’t wildly successful in their own right, but mimicking what others have done isn’t going to get you noticed—ESPECIALLY if you’re starting from scratch.

The reason Apple soared to the top of the mountain wasn’t its clean aesthetics and intuitive UX—those things were the RESULT of a mindset. The slogan “Think Different” feels like a cliche in today’s world, but back when Apple debuted it, it was revolutionary.

While developing the Mac in the early ‘80s, Jobs flew a pirate flag in the Macintosh building, saying “it’s better to be a pirate than join the Navy.”

To the developers on the project, this was a significant motivator. “Being a pirate meant moving fast, unencumbered by bureaucracy and politics,” Macintosh engineer Andy Hertzfeld told Quartz. “It meant being audacious and courageous, willing to take considerable risks for greater rewards.”

But that type of audacity wasn’t without its repercussions. We sometimes forget that Steve Jobs was very publicly ousted from Apple in 1985 because his vision was so radical that it clashed with then-CEO John Sculley’s.

Jobs didn’t let up or concede his vision that would have returned him to the center of the pack He founded NeXT—and oh, a little studio called Pixar. Apple eventually bought NeXT, and you know the rest of the story...

When it comes to you taking pages out of Jobs’ book, you need to look beyond the results and understand HOW they came to be. Don’t wear the black turtleneck—adopt the mindset that caused Jobs to put the turtleneck on.

Don’t Serve Diluted Kool-Aid

The other way I see founders craft their message is with a desire to be liked by as many people as possible. They homogenize their stories to try and appeal to a wide audience.

In theory, this makes sense. The more people you get to hear your story, the better chance you have of success, right? That’s the law of averages.

What’s actually happening is that by broadening your audience, you’re diluting your message. You’re trying to appeal to everyone, and you end up appeasing no one. Remember when you were a kid and your parents tried to stretch a packet of Kool-Aid so it could serve more people? Yes, the batch yielded more glasses, but it was bland and undrinkable. The sweetest, most appealing Kool-Aid was from the batch that served fewer but was more concentrated.

This is the same principle you should use when constructing your story. You want it to be precise and selective. It’s not going to hook every investor—and it shouldn’t!

Your story should act as a filter, sifting out the people who are not meant to hear it. I live this principle myself. When I post something on LinkedIn or film a YouTube video that says “some founders don’t have what it takes to become world-class,” it rubs some people the wrong way. They’ll push back in the comments, telling me that I’m wrong for feeling that way or irresponsible for putting what they perceive as “negative thoughts” out into the world.

But rather than soften my stance and attempt to deliver more “approachable,” content, I stand firm. I maintain my point of view because I understand that my beliefs aren’t for them. And that’s okay!

The audience I’m trying to reach and inspire will be ENERGIZED when I tell them some people can’t do it. They’re the ones who want to knock down walls and prove that they’re world class.

After all, that’s why you’re here reading this, isn’t it?

At the end of the day, the way you’ll stand out from the crowd is not being afraid to do so. Sure, there’s a small chance you’ll get caught in a mastodon stampede, but by playing it safe, you’ll never differentiate yourself from the rest of the pack.

Be better than the rest. Be bold and stand out.

As Teddy Roosevelt said, “The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

RESOURCES for Founders and Storytellers

Earlier I mentioned the danger of taking pages from other people’s playbooks, and that’s a topic legendary music producer Rick Rubin addresses in his new book, The Creative Act: A Way of Thinking. Rubin states that the “rules” of art—whether that’s music, writing, painting, or creating a business—can be extremely limiting if you follow them too closely. This is an amazing book that can help you to get into that creative mindset of going boldly where no person has gone before.  

When you need to give a big public talk, there's a structure that will help you make sure you get it right. You can check it out here in Speak Like A Pro.

Speaking of Steve Jobs, he knew how to handle a tough question better than anybody. He understood how to take a big pause, address the challenge, and then reframe everything so he gave a winning answer. Here's a breakdown of a classic Steve Jobs masterclass.


"I'd be more frightened by not using whatever abilities I'd been given. I'd be more frightened by procrastination and laziness." -Denzel Washington

I saw that quote earlier this week and it reminded me of one of Kobe's. That's the mindset.

See you next week.

Know someone who might enjoy it? Please pass it along!

Know someone who might enjoy this?

Read other issues: