Three pieces to trial lawyer level storytelling

Greetings, Chief Storytelling Officers.

This year I want to encourage you to tell more stories. I mean that in the most literal sense. Write more of them on LinkedIn. Tell more of them to your team. Sign up for one of The Moth’s storytelling slam events they host.

I believe we are entering into the golden age of real, raw, and most of all human storytelling.

This quote that starts off Robert Greene’s Mastery fits perfectly for this year and he titles it “The Ultimate Power.”

“Everyone holds his fortune in his own hands, like a sculptor the raw material he will fashion into a figure. But it’s the same with that type of artistic activity as with all others: We are merely born with the capability to do it. The skill to mold the material into what we want must be learned and attentively cultivated.” Johann Wolfgang Von Goethe

-Robbie

Three Pieces to Trial Lawyer Level Storytelling

In February of 2020 I tried the last jury trial of my career. It was only the second case of my career on the defense side. 

A murder case where I believed the defendant, who was my client, had acted in self defense. My client, in his 30s, had shot and killed his brother, also in his 30s, in a hallway inside of their house. There was no doubt about how the victim had been killed as my client had told the police everything. It was a tragedy but I did not believe it was a crime (and keep in mind that I tried 100 jury trials as a prosecutor where I put people in prison for murder on a regular basis).

I’d been brought onto the trial team a few months earlier specifically for a couple of reasons. The first was that both of the prosecutors on the case happened to be former bosses of mine. I’d studied them and knew the way they would play the case. 

The second was that I’d tried 101 cases up to that point and had huge verdicts to my name. That type of reputation went a long ways and I had a distinct personal style that I took into every case I tried. I don’t say this to brag, I say it because it was true. 

The final reason they brought me in is because I was always experimenting with ways to bring in psychology, science, and experts to strengthen my case. I did weird things that only made sense to me because I wasn’t afraid to go against norms and standards. 

In that case I decided to do two things nobody had thought of before. 

I came up with this idea that since this was a shooting in self defense, we could create an analogy to how the police officers arrived on the scene and arrested the defendant. I could pose how what the deceased had done would have caused the officers to shoot the defendant if he’d done the same thing. 

The police officer I chose to do that with was a seasoned and well respected officer. Step by step he helped me build the case that my client had acted in self defense and if he’d been an officer it would have been considered a clean shoot. 

Next I decided to use a psychiatrist to explain brain chemistry and the fight or flight response. I’d always loved studying the scientific literature and diving into obscure areas of how the brain affected the way people made decisions and acted.

Specifically I was using the psychiatrist to show how the chemicals that lead to fight or flight could transform a fairly docile man into a bravado filled one saying things that seemed outside of the ordinary. I went full scientific mode to explain the actions and help the jury put themselves in that situation. 

A week long trial and a day long deliberation later, the jury found the defendant not guilty of murder. My client went home to his family. 

I never tried another case. I left that world behind to take those lessons and skills to an entirely new one. Almost 4 years later and here I am.

Now I know that was alot about me and this newsletter is about how you can get better at storytelling. So let’s breakdown how you can do things similar to what I did in that case. 

Those 3 reasons I was brought into the case are all applicable to you in this storytelling journey. 

Piece One

The first piece of great storytelling is to know your audience. What are their motivations, expectations, and desires? 

Without an understanding of those pieces, your story is just for an audience of one…

You. 

And story is not meant to be for just one person. In fact I always tell people the goal of any story is that two people are moved by it. 

You and one other person. 

So if you’re pitching an investor, know what they care about. If you’re talking to a candidate, know what they care about. If you’re talking to your team, know what they care about. 

You get the idea. 

Piece Two

The second piece of great storytelling is to put in the work. I wasn’t great in my first trial. I wasn’t great in my 20th trial. 

I actually had a theory back in my trial days. 

It took 5 trials just to know what to do in a court room. It took trials 5-15 to learn how I wanted to show up in a courtroom. It took trials 15-25 to appear smooth in the courtroom. It took trials 25-40 to push the limits of what was possible in the courtroom. And finally it took trials 40-50 to see all the potential possibilities and pattern match everything in a courtroom. 

For me that took exactly two and a half years to get to jury trial number 50. I can tell you that the next 52 trials of my career went significantly smoother. My win rate went through the roof because of all the things I’d learned during those first 50.

This is why both storytelling and fundraising can be seen as a skill you can improve. Each investor meeting you get better. Where you want to ultimately get is what I call “Effortless Storytelling.”

It’s a flow state where you slow everything down. 

If you’re frustrated with your results, know that it’s natural to take time to reach mastery. 

I’ve been re-reading Robert Greene’s Mastery which gives all kinds of research and real examples of the path to mastery. None of the masters got there overnight. 

Piece Three

The third piece of great storytelling is to lean into your own idiosyncrasies and embrace doing things that make sense to you. 

You see the world a certain way and it’s bringing that authentic side into the story that makes it stick out. The worst thing you can do is sound like everybody else. 

My approach worked in that case because I knew I was different and could bring it all together. My boss at the time thought I was crazy when I told him what I wanted to do but he ultimately trusted me. It was a risk but it was calculated. 

One of my favorite movies is Gladiator. There’s a scene in the movie where Proximo is talking to Maximus when he’s still a slave fighting in the gladiatorial games. He says this…

“I wasn't the best because I killed quickly. I was the best because the crowd loved me. Win the crowd and you'll win your freedom.”

In so many ways that quote rings true. 

As a storyteller, investor, founder, executive, and leader your job is to tell the story that wins the crowd. 

Do that and you win your freedom to do whatever you want. 

Resources for you to check out

Marc Andreessen with Rick Rubin for 3 hours is quite the interesting listen when you have some time.

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Lots of people ask about how to become a better storyteller. One of my favorite ways is to read the speeches of great orators and then hand write them out. You will learn to feel rhythm and pick up on rhetorical devices that resonate with you. Here’s one that I love on JFK’s speeches.

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This 17 minute video breaks down how Interstellar perfectly hits all the marks of the Save the Cat story structure. It’s interesting as storytelling is a blend of science and art. You need to master both to become elite at it.

Ways to get help with your storytelling and fundraising

1. If you’re an early stage company looking to nail your fundraising story, check out Potential AI. Our ai will guide you through the exact process and then write your 3 minute founder origin story and 3 minute startup vision story.

2. If you’re raising at least 8m as a founder or 50m as a fund, apply to work with me here.

3. If you’re thinking that it’s time to write the perfect vision story for your growth or later stage company (might be a new strategic narrative, might be for a major company wide keynote, might be for a huge product launch you have coming up), you can email me at [email protected].

4. If you’re looking to have me speak to your organization, leadership team, or at an event, email me at [email protected].