You're 3 stories away from raising millions of $$$

Get these right and watch the money flow in

Welcome back, Chief Storytelling Officers.

Earlier this week I got asked an interesting question by a VC.

They asked me what makes me different from other storytelling people out there.

My response was simple.

"I told stories in 102 jury trials where life and freedom were on the line."

Everything in this newsletter comes from that experience and all the lessons learned living in the trenches of a courtroom for 7 years.

Let's get into this week's deep dive.


DEEP DIVE: Rising Above the Noise

If you were to ask a room of founders to raise their hand if they were world-class, nearly the entire room would put their hands up.

It’s a nice sentiment, but of course, that’s statistically impossible. It’s tough to elevate yourself to become the best of the best, and as I’ve said before, most will never get there. Most will stay in the middle of the pack where it’s tough to get noticed.

I recently talked to a great VC, and they told me of the 1,000 decks they reviewed from funded companies, none of them jumped out.

If you’ve followed this newsletter for any amount of time, the reason they gave for why this was won’t surprise you: They felt like none of the decks made as deep of an emotional impact as the investors were looking for.

The first reason VCs weren’t wowed by these pitches was the delivery method. I’ve previously talked about why pitch decks will doom you more times than not. Decks are cold and impersonal. The characters won’t come to life, and your audience won’t be able to feel your WHY. World-class founders will NEVER rely on a pitch deck to close their funding.

The other reason is a bit more difficult to remedy. The truth is that most founders have a limited knowledge of storytelling. Most study the basics of how to get their point across. But true, world-class storytelling is complex and requires a good deal of study and practice.

World-class storytelling requires a deep understanding of psychology, neuroscience, classic rhetoric, oratory, history, and tonality. It must be studied from so many different sources—places most founders have never explored.

Sound overwhelming? It is.

It makes sense why most don’t pursue expertise in storytelling. Founders have been focused on constructing businesses out of thin air. They’re builders, dreamers, and innovators. So it’s not their fault that they can’t tell a compelling and inspirational story. It’s not their fault that they can’t raise their series A and beyond rounds because their story falls flat. It’s simply not their core competency.

World-class founders are different. They find a way to become storytelling experts.

Yes, it takes time and dedication to become a world-class storyteller, but everyone has to start somewhere. If you’re at the point where you feel like you have the basics down, but you aren’t sure where to go next, here are three main skills that will start you down the road to becoming an expert and elevate you above the rest of the pack:

Craft Your Founder Origin Story

Every superhero has an origin story, and as a world-class founder, so should you. Your mission in crafting your origin story is twofold:

1 — To build trust with your audience.

2 — To set your frame.

When you properly craft your origin story, you establish yourself as a character that your audience wants to root for. Do it right, and your audience will sympathize with you—no matter the circumstances.

A great example of this is the 2019 Todd Phillips movie Joker. It follows failed comic Arthur Fleck and how his descent into madness ultimately results in him becoming the arch villain, Joker.

This demonstrates the incredible power of the origin story because we KNOW Joker is a villain. We KNOW he goes on to cause death and mayhem in Gotham City at such high levels that only the Caped Crusader can stop him. And yet, we spend 122 minutes empathizing with him and understanding his plight. We actively ROOT for him to lash out at the world that has been so unkind and unfair to him.

In order to begin building your Founder Origin Story, start with answering these simple questions:

1 — How did you get here?

2 — What makes you special?

3 — Why do you care?

I won’t lie to you and tell you that answering these questions are easy. For many, it feels like bragging. And it may be scary to put yourself out there in such a vulnerable way. But by opening yourself up, you provide the opportunity for your audience to do the same.

Craft Your Startup Origin Story

Once you’ve established your personal origin story, it’s time to craft your company’s. This is all about showing why what you’re doing is important NOW, as well as demonstrating that people WANT what you’ve built.

This is one of the most difficult storytelling skills for founders to acquire. For some reason, as soon as people begin to describe their business, they go brain dead and start speaking in jargon, technicalities, and features.

I saw this happen in the courtroom all the time during my time as a trial lawyer. I’d watch attorneys get in front of a jury and speak about facts and data. More times than not, they’d lose the case. The trial lawyers who WON were the ones who crafted their cases using memorable, emotional, and results-driven stories.

If that tactic is powerful enough to convince a jury when a person’s life hangs in the balance, it can absolutely work for founders convincing a VC to write a check.

The way to craft your Startup Origin Story is by using the three Ps: Purpose, Passion, and Potential.

Purpose is all about identifying the problem and solution. What problem will your product solve, and why is now the right time to do it?

Passion gives you the opportunity to share your emotion and transfer it to your audience. You want to explain why you and everyone else involved—your team, your customers, and your investors—should too.

Potential is when you lay out how big this opportunity can be. You instill confidence by demonstrating how you will defend your vision and make sure you win.

Craft Your Future Vision Story

The final skill is one that works your creative muscles the most, because in a way, you’re crafting fiction.

Whether you realize it or not, you’re very familiar with Future Vision Stories. Pop culture is filled with them. “The Jetsons” told a Future Vision Story of what life would be like in the 21st century. Ditto The Matrix, Black Mirror, Demolition Man, Star Trek…the list goes on and on.

As such, our minds are primed to think fantastical things about the future. Take that instinct and run with it, painting a vision so massive and enticing that your audience would be crazy not to want to get on board. Let the investor’s imagination take over. Get them to start counting all of those dollars that will flow in when it becomes real.

The first step is to determine which Future Vision is right for you. Do you want to describe the short-term future—one-to-two years—or the long-term—five-to-10?

Once you do that, ask yourself what that future looks like if everything goes perfectly. What does the world around you look like?

Like I said before, this is the most creative skill of the three, and as such you should employ literary techniques just like novelists do. A great device to use is imagery, wherein you describe not just what things look like visually, but what they sound like, smell like, and taste like. Engage every sense however you can.

It may seem like a lot—to have to learn yet ANOTHER skill. But I’m telling you: investing in this learning is one of the primary ways that World-Class founders separate themselves from the pack. By mastering these three skills, you won’t ever have to worry about being lost in the stack of 1,000 pitch decks. In fact, if you do it right, you won’t be in that stack to begin with.

By reading this newsletter, you're taking a step in the right direction.

When you're ready to take the leap and become world-class...

You know who to call.

RESOURCES for Founders and Storytellers


If you want to learn more about the psychological effects that stories have on our audiences, Will Storr has an incredible book on the topic called The Science of Storytelling: Why Stories Make Us Human and How to Tell Them Better. The book is primarily intended for fiction writers, but as this Forbes article points out, there’s a lot that founders can learn from Storr’s principles as well.


"I was chasing perfection and excellence even though I knew I would probably never catch it. But just the fact that I was willing to chase it, I would defeat my opponents because they would never chase something that didn't have any guarantees."


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