Why do the bad guys keep winning?

How to avoid going to The Dark Side

December 12, 2022
min read

Welcome to the 23rd edition,

We are all playing the game of Competitive Storytelling.

I know there are lots of resources out there around storytelling. Books, podcasts, newsletters, and more that cover traditional storytelling.

This isn't one of those. I'm not interested in traditional storytelling.

You're here to win and win big. That's the type of storytelling I care about.

So let's get into this week's deep dive on Jedi Storytelling.


DEEP DIVE: Jedi Storytelling

There’s no way that you missed the news about FTX and CEO Sam Bankman-Fried’s epic collapse. Correction...fraud and theft.

How does a fraud like that get billions in capital and other great founders struggle to get any support?

I mean it's still appalling to see the numbers for female and diverse founders when it comes to funding. But that's a rant for another day.

I often talk about how there are levels to storytelling. There are good storytellers and great storytellers.

SBF found a way to sell a story to investors. It's like he was one of the Sirens from Greek mythology singing to attract sailors to crash onto the rocks. He manipulated people and got investors to dive in without doing due diligence. He convinced his circle that FTX didn’t need oversight by selling a fantasy.

As a result of his very talented storytelling skills, lots of people got hurt.

The interesting thing to me about the FTX meltdown was that if you looked closely, all the signs were there. One thing I learned during my time as a child abuse prosecutor was to look for sensory details—things that could only be true if the thing had actually happened. SBF crafted a masterful facade, but upon closer examination, his story lacked some key sensory details that could have revealed the true picture.

I’m sure the company’s story will serve as a cautionary tale for founders and investors alike for years to come, but it’s also a testament to the power of storytelling. You see, storytelling is like a chainsaw: When wielded by a skilled craftsman, it can build and shape our world for the better. Or it can end up like The Texas Chainsaw Massacre.

Tools are not evil. Tools are not good. Tools are tools and it's the person who wields them that decides what type of impact they will have.

SBF isn’t the first person to use storytelling for evil. Elizabeth Holmes and Bernie Madoff are two recent examples in the business world, but history is littered with personalities who weaved narratives in a way that convinced people to believe in and perform unthinkable atrocities.

I don’t even need to name names because you know them: The dictators, the rulers, the genocidal maniacs. All of them have used storytelling in one way or another to manipulate their audiences into adopting their points of view.

One of the strangest parts of my life is studying the terrible examples in history. How does a leader convince an entire nation to demonize a group of people?

Sadly, it's not that hard and the same formula gets used time and time again. This is why I see it as my mission to make sure the good men and women come out on top in this world of competitive storytelling.

It reminds me a bit of Spiderman. Throughout his entire life—even before becoming Spiderman—Peter Parker’s Uncle Ben continually issued one piece of advice: With great power comes great responsibility.

Storytelling is a great power, which means it is ALSO a great responsibility. This is why it’s never been more important to make sure that we lift up the storytellers who are using it to change the world in a positive way.

It may sound silly, but I like to think about storytelling as The Force in Star Wars. There’s the Light Side and the Dark Side. Just as it was to Anakin, the Dark Side can be an intoxicating way to validate some of the ways you’ve felt wronged. The Dark Side can feel more powerful, but only because it results in raising you above others in unethical ways.

But here’s the thing; Just like in Star Wars—or the litany of leaders who have used storytelling for evil over the years—at some point, people are going to figure it out. They’re going to catch you in the lie and realize that you manipulated them. And it’s all going to come crumbling down.

The Yodas and Obi Wans, on the other hand, are the ones who want to bring balance to the universe. These real-life Jedi are people like Malala Yousafzai, who, as a teenager, told stories that have impacted and inspired human rights advocacy across the globe.

There are dozens of others who used storytelling to propel humankind forward. JFK told the story of putting a man on the moon. That led to 400,000 people rallying behind a mission and pulling it off. Changing the course of history.

MLK told the story of a dream he had for his children. He told the story of the promised land that he had seen. He changed America and inspired leaders across the world.

Gandhi told the story of how non-violent protest could free a country. India's independence resulted from his belief.

Nelson Mandela told the story of bringing together a fractured country and ending apartheid. He changed South Africa and his story took him to the presidency.

Mother Theresa told the story of the value of the poorest among us. She changed the hearts and minds of the world.

These are just a few examples of stories used for good. The ones that create lasting impact.

Why did they succeed?

They tapped into the human spirit. They touched raw human emotions. They made people feel, see a different and better future, and they played to the best in each of us.

And they never stopped believing in that story. They had that inevitable mindset.

Through their stories they knew they could and would change the world.

I hope if you’re reading this that you’re a Jedi. I’ve made it my life’s mission to create an army of ethical storytellers. An army of the best competitive storytellers and an awakening of the unimaginable power when yielded for good.

What I want to do is show you the best ways to tell a story and how you can make the greatest impact on the world. I also want to remind you to use it for good, to enact positive change that makes a difference and inspires new generations.

I challenge you to go out there and pick the Light Side. Choose the side that’s going to use storytelling to make the world better.

It's going to take work. It won't be easy. You will want to give up. You will curse me for pushing you.

It won't stop me from pushing you and helping you get there.

Leia once said, "help me, Obi Wan Kenobi. You're my only hope."

Today, we need you to step up.

Welcome to the rebellion.

RESOURCES for Founders and Storytellers

If you really want to get into the weeds of ethical storytelling, Hanna Meretoja has an incredible book called The Ethics of Storytelling: Narrative Hermeneutics, History, and the Possible that you might want to check out.


“What are your expectations surrounding valuation?” Need help answering it? This TechCrunch article provides some tips.


One of my favorite books is Ender's Game. Here's a quote from it's author I've been thinking about recently.

"There are times when the world is rearranging itself, and at times like that, the right words can change the world." -Orson Scott Card

How you can work with me:

My storytelling coaching is for venture backed founders, multi-time founders, investors, and CEOs. I only coach 5 of these at any time. To apply to work with me, simply reply to this email with a brief bit of background and why you'd be a good fit.

My fundraising consultancy is for series A and beyond. If you're raising a seed, the round needs to be at least 5m. This program has led to founders raising over $330,000,000 in venture capital the past 18 months. You can apply here at Founder Fundraising.

If you're looking for me to speak at your event, speak to your team or portfolio, or run a workshop, please reply directly to this email.

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