Sell Yourself Without Feeling Sleazy

3 steps to perfect story selling

November 21, 2022
min read

Greetings, Chief Storytelling Officers.

Last week I was in Sao Paulo where I spoke to 150 Latam founders about storytelling, fundraising, and the iron mindset it takes to win.

I also got to experience my first ever Formula One race in person down there. Watching those drivers perform at those speeds is incredible and I left with a new level of respect for their craft. This was greatness on full display.

Back in Miami this week I reflected on some big takeaways from my time in Sao Paulo.

One thing kept coming up and that's what I want to get into today with all 1,507 of you reading.

How can you show people how great you are without it sounding like you're bragging?

How can you show people how special you are without it sounding like you're an a-hole?

I've always known there's a way, and today I want to share it with you.

Today, let's dive into how to brag without bragging.


DEEP DIVE: Brag Without Bragging

It’s easy to talk about other people. That’s why we like to gossip—it psychologically rewards the brain. But when it comes to talking about ourselves, things get much trickier.

Studies suggest we also get a dopamine hit when we talk about ourselves, but for many, it comingles with a conditioned guilt response that comes from societal pressure and upbringing. We learn from a young age that bragging about ourselves is bad and that praise should come from demonstrating our worth, not talking about it.

But often, we swing the humility pendulum too far, and it prevents us from showcasing our abilities, skills, and experience. If you’ve ever felt uncomfortable talking about your accomplishments in a job interview, you know exactly what I mean.

The problem for founders, of course, is that you’re not going to be able to skate by on just pitching your company or product. Investors aren’t buying that. They’re buying you. And no one else is going to sell them on you but YOU.

I see founders struggle with this all the time. They either sell themselves so short in a pitch that they come across as unremarkable, or they come off as egotistical and end up pushing people away instead of drawing them in.

The balance is admittedly tricky, but I have a solution: Storytelling.

Shocking, right?

But don't worry, this newsletter is going to show you how to do it and examples that will help you see how people you love do it.

Once you find and create your story, you can leverage it to build your ethos (more on that later) and wow your audience—without coming off like a pompous jerk.

Here’s how to do it in three steps:

Step 1: Find What Makes You Special

Here’s a hard truth about being a successful founder—or really, life in general: “Greatness is not for everybody.”

That’s a quote from Kobe Bryant, but it’s something I wholly believe in as well. It may be harsh to hear, but not everybody is cut out for certain things. Some people aren’t cut out to be great founders just like they aren’t cut out to be great athletes or musicians or painters.

We’re often told that we can be anything if we put our minds to it, but that’s not true. Just because I want to be Michael Jordan doesn’t make it so. I could eat the same food he does, wear the same clothes, work out in exactly the same way, but I still wouldn’t be him.

Trust me, I tried. I sat out on my driveway dribbling, driving, and shooting game winners for hours every day as a kid. As you can see, I didn't get to be MJ.

Just because you WANT something doesn’t mean you get to do it. Instead, you have to discover what makes YOU special.

This is something the best founders in the world understand. Part of being a founder is embracing the things that make you unique, that make you stand out. They’re the things that make other people say, “This is the type of person I want to bet on—the person I can see building the future we want to live in.”

Sometimes that means embracing your own weirdness and leaning in. This is exactly what podcaster Chris Williamson discusses in his Ted Talk. Williamson says we’ve been conditioned to hide what makes us unique out of fear we’ll be ostracized and cast out of the pack. But our weirdness is our unique strength, and it’s the key to becoming more popular and more desirable.

I found this funny the other day when James Roycraft-Davis (founder of Luna) replied to a comment I had left on Jesse Randall's post about Elon. I dropped a quote from Harvey Dent in The Dark Knight.

James commented the following: "I've never met someone who recites so many lines from films before."

And he's right. I do it all the time. It's uniquely me. It's part of what makes me special. I can find a movie or tv scene or quote that ties into any conversation or subject.

Here's how this applies to you.

Ask yourself: What makes you special? What’s the one thing you can bring to the table that no one else can?  

Step 2: Craft Your Origin Story

The most important story you need in your arsenal is your origin story. It’s the story of your journey, how you got to where you are today.

Since you're reading this, you know I believe that the Founder Origin Story (and yes Founder can apply to your role as a VC or executive too) is the most important story for any leader to share. I've gone over this before but the 3 core questions for my version of the FOS is the following:

  1. How did you get here?
  2. What makes you special?
  3. Why do you care?

Simple questions but there's a ton to unpack there. It's why I spend 2-4 weeks with a founder, CEO, or VC to get this perfect. Once it's perfect, it's a game changer.

Inside of the Founder Origin Story there are a few frameworks for how to structure it.  

The ones I like to use with my coachees are the following:

  1. Hero's Journey (more below)
  2. Acute Event
  3. Lifetime Journey
  4. Pieces in Reverse

These are my frameworks (except for number 1) which I'll be writing on much more in this newsletter and in my future book. But let's dive into a bit of the first one which is a classic.

Popularized by mythological researcher and writer Joseph Campbell, The Hero’s Journey is a storytelling structure wherein the hero is called to adventure from the ordinary world, is guided through trials and tribulations by a mentor, and then emerges victorious against a final and most dangerous foe.

You may have never heard of it, but I guarantee that you’ve seen it in action thousands of times. It’s the same structure used by Star Wars, Finding Nemo, Harry Potter, and The Hobbit. And you can apply it to your own origin story too.

As a founder, your origin story is critical. It’s the story you’re going to tell at every step of your journey to success—when you’re pitching pre-product; when you’re starting to get traction and finding product-market fit; when you’re growing and building toward the next stage; when you’re preparing for the IPO; when you’re ringing the Stock Exchange bell; when you’re telling your grandkids about your wildly successful life as a founder.

Your origin story is the one who lets people know who you are and what makes you special. It tells them why they should bet on you.

Step 3: Learn to Brag Without Bragging

So you’ve determined what makes you special and you’ve folded that into your origin story. Now what?

It’s time to take those two elements and use them to build your ethos.

Ethos is one of Aristotle’s three modes of persuasion, wherein the speaker establishes their authority and credibility. Ethos is often tied to moral character, but it can also be associated with trustworthiness, expertise, and pointing out similarities with the intended audience—what Aristotle called phronesis, arete, and eunoia.

In other words, establishing ethos is all about sharing with people WHY you’re great. But how do we do that without bragging?

We tell a story.

Simple. And it works like magic.

An incredible example of this is from Brene Brown. In her Ted Talk, Brown tells a story about a time she showed up for a speech and needed to be introduced. The person hosting the event asked how he should introduce her, and Brown tells a 60 second anecdote about researcher storytelling.

What she’s doing in that moment is sending a message to the audience: I am a professional speaker. People pay me to talk to them. They listen to me. They respect me. I’m credible. I’m an authority.

If you listen to the talk, you’ll notice she never says any of those things explicitly. They’re all IMPLIED through the anecdote. The audience understands that Brown has spoken before, that she’s a researchers storyteller, and people have paid to see her before. By hearing that anecdote, the audience is automatically more receptive to what she has to say.

Telling your origin story allows you to brag without bragging. It’s the old mantra show, don’t tell.

Once you’ve accomplished those three steps, you’ll be much closer to sharing your greatness with the world, and you won’t have to feel like a jerk doing it.

If it worked for Brene Brown...

Why not give it a shot?

RESOURCES for Founders and Storytellers

If you really want to get into nerdy storytelling mode, I’d definitely recommend checking out Joseph Campbell’s seminal book, The Hero With a Thousand Faces. It combines the insights of modern psychology surrounding storytelling with Campbell’s research into mythology. To me, it’s fascinating to know that stories push the same buttons in our brains that they did at the beginning of civilization.

For those of you early in your founder journey, here's a twitter thread with a whole bunch of pre-seed VCs to check out.

How much will the rest of the crypto world suffer after the FTX fallout? I wrote this the other day on LI and I'll say it again, I'm pissed at how this played out. The virtue signaling, the manipulation through storytelling, and most of all the fraud that hurt so many people. Read the full article here.


Holmes got sentenced to 11 years in prison this week. SBF destroyed lives with his fraud.

I see those actors as the Dark Side of the Force. They use words and stories to steal.

I want to see a rise of the Light Side of the Force. Luke, Lea, Han, Obi-Wan, and Yoda. I know we can turn the best founders and VCs, the ethical founders and VCs into storytelling machines.

So with that in mind, a reminder to embrace the Yoda mindset.

"Do or do not, there is no try."

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Want to learn more about working with us at Performative Speaking? You can check out our site and apply to talk with our team by going to Founder Fundraising.

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