The Invisible Opponent You Face Everyday

The high-stakes game to get funded

December 19, 2022
min read

Welcome to The Storyteller's Playbook,

I won't lie.

I did not expect the massive amount of interest in the live story redesign event I'm running this Wednesday at 1pm est.

Over 200 people have signed up. We had to purchase a one time zoom upgrade to host everyone. 63% of people have applied to be one of ten founders giving their company pitch for me to redesign.

I'm pumped for Wednesday to do this virtually.

2023 may even be the year to run some in person workshops. Maybe in Miami, maybe some other places.

Signups close on Monday to attend the free event. You can sign up here.

Now let's cue the Mortal Kombat music and dive into the deep dive.


DEEP DIVE: Storytelling Kombat

Back when I was a trial lawyer, I lost a pretty high-stakes case to a good defense attorney. I couldn’t understand why. I’d prepared like crazy and had all of my ducks in a row. My argument was tight. But I still lost.

I was pissed. I was frustrated. Most of all, I was embarrassed. How the hell did I lose?

When I listened to what the jury told the defendant in the hallway, I learned the most important lesson of my career.

They told him these words: "We know you were guilty and you know you were guilty. But we believed your story that you felt bad and wanted to do better. We want you to have the chance. Don't mess it up."

I walked up to them after hearing this and tried to maintain my composure.

"I'm sorry, did you say that you know he was guilty and you still voted to set him free?"

That's when they told me that I was right but they connected with the defendant. They didn't connect with me.

Because I told them the facts. The defendant told them a story.

That’s when I realized that it was a game.

I know that’s harsh to say, considering I worked murders, capital murders, child abuse cases. The stakes of the game were incredibly high. People’s lives were literally on the line. Many of the defendants who went against me in the courtroom are in prison for the rest of their lives. It was heavy.

At the end of the day, my trials came down to what I called Competitive Storytelling. There were winners and there were losers, and the winner was the attorney who told the best story.

If you think about it, most of our lives involve storytelling games. When someone tells a story at a party, our instinct is to one-up them with a better one. Part of our election process involves debates, where candidates tell their stories head-to-head, and analysts endlessly determine who “won.”

We thrive on head-to-head storytelling. Shows like Crossfire or Pardon the Interruption pit pundits against each other in debates over sports and politics. Competitive storytelling has also made its way into pop culture, with characters like Will Ferrell taking the stage in Old School to take down James Carville.

I personally like to think of Competitive Storytelling not as a debate, but a battle where losing isn't an option.

When I was growing up, I used to go to my friend’s house and play Mortal Kombat, the video game where two fighters battle head-to-head. To me, Competitive Storytelling is just like that game, no matter whether you’re a lawyer, politician, founder, investor, or CEO. They’re all stepping up and battling an opponent, and the best storyteller gets their pick of anything they want.

The Hidden Opponent

In a courtroom, it was very easy for me to identify my opponent and know whether I’d won or lost. I was on one side, the defense on the other. I’d tell a story, the defense would try to argue against it—objecting, interrupting. Then they’d tell their version of the story and say “no, he’s wrong, my story is better,” and that was what the jury had to decide on.

When you’re a founder though, the lines are much more blurred. You may not even realize that you’re playing against someone else, but you are.

You see, if an investor has a call with you, the odds are they ALSO have a call with ANOTHER founder later that day. That founder pitching their idea is your hidden opponent—you don’t see them, but they’re there.

That isn’t to say that I love the idea of founders competing against other founders. My mission is for ALL founders to win and get the funding they need to change the world. But the reality is that every VC only has so much capital that they can deploy. They only have so many deals that they can be a part of.

So if you really love a fund and you want them to invest in you, you have to out-compete that other founder vying for the same funds. Or rather, you have to out-storytell them. If you’re the best storyteller, you get the funding.

Again, I know it sounds harsh, because you want to think that all ideas can win and that the good ideas are going to rise to the top.

The reality is, good ideas only sing when they’re told in the most compelling ways. The best tech, the best products, they don’t matter. Silicon Valley graveyards are littered with hundreds of startups—all of whom had the best tech and most innovative products. But a product is only as good as the story behind it. That’s the world you live in.

Keep It Simple

The best ideas can be absolutely boring if they’re told incorrectly or shared in a confusing manner. You have to think about how you can simplify your message and bring it to life so you can tell that compelling story.

There are plenty of resources for you to figure that out and it's something I talked about this week in a LinkedIn Video about my favorite advertisement pitch ever from the show Mad Men. Remember, it needs to be simple so that you can tell it to different audiences in a clear way.

Think about how you can simplify that message and really bring it to life. Not the features, not all the tech jargon. None of that stuff is compelling. What sticks with an audience is the picture you paint. Think about where the world is today and where the world ends with the company that you’re building.


Once you’ve simplified your story and really focused on how everything will be different after your company changes the world, it’s time for your finishing move.

In Mortal Kombat, that was called the fatality, where your opponent swayed with fatigue and the omnipresent referee would implore you: “FINISH HIM!” Then you’d mash a specific set of buttons and execute a ridiculously violent special move. Even just writing that brings me back to my childhood and amps me up.

You have to get your story across the finish line and execute the fatality. Doing so in Competitive Storytelling means maintaining that presence, calm, and confidence in those final meetings. When you’re that close, you have to double down on your storytelling skills and elevate your position to get the funding you need.

Look, I get you might feel bad for the other founder you just drop-kicked into the pit of spikes. But they’re going to have to go somewhere else and compete with another opponent in the storytelling arena. That’s the way the game works.

At the end of the day, we’re all playing the game of Competitive Storytelling. Someone’s gotta win, and someone’s gotta lose. That’s the way games are played.

I f'ing hate losing.

If you're reading this, I bet you hate it too.

RESOURCES for Founders and Storytellers

Richard Branson is never dull in anything he does, and the new HBO Max docuseries, BRANSON, is no exception. The four-part series explores how his pursuit of the extreme served to grow his business and brands. It’s definitely worth a watch.

BONUS: Branson believes that storytelling is the competitive advantage you need to build a successful business. Read what he had to say about it in this Forbes article.

This tweet thread breaks down why AI won't be the end for creators, writers, and artists but instead will usher in a beautiful new era. I agree. After all, the camera allowed the rise of Monet and Van Gogh.


I hope you all have a wonderful Christmas, Hanukkah, and holiday season.

For next week, I'll be sending a special edition of the newsletter that will be more personal.

We will be back to our normal content on January 1, 2023 as we kick off an amazing new year. I'll leave you with one of my favorite quotes from one of my favorite Christmas movies

"Faith is believing in things when common sense tells you not to." -Miracle on 34th Street

To apply to work with me, you can go here.

We work with venture backed founders who are raising their series A and beyond.

We work with CEOs on their company narrative to implement both publicly and to implement throughout the organization.

To find out more about having me speak to your team, at your event, or run a workshop, reply to this email.

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