Avoid this recipe for failure

How to persuade like a trial lawyer

April 23, 2023
min read
Greetings, Chief Storytelling Officers.

This week I'm co-hosting a special free pitch practice event. We have around a dozen active angels and VCs who will be there to listen to founders and give them feedback on their ideas and pitch.

The event is Friday at 1p est and you can sign up here.


DEEP DIVE: Why Most Storytelling Fails

Early in my career as a trial lawyer I'd win some cases and I'd lose some cases. Luckily those cases were low level driving while intoxicated cases where nobody had been hurt. That's why every prosecutor started at that level.

Once I hit around 30 trials which was in my 3rd year as a lawyer, things changed. I started winning a lot and losing only a little. This mattered because I was trying domestic violence cases at this point where real people had been hurt and lives had been ruined.

Once I hit 54 trials, I was promoted to the felony cases where people would go to prison for decades if I did my job right. In fact, that's exactly what happened. I tried robberies, murders, and child abuse cases where people are now in prison with sentences of 60 years, 99 years, and even life without parole. I didn't lose these cases.

And yet, from a degree of difficulty each level got harder. The defense attorneys were better on the serious felonies. The cases were tougher to prove with more complexity. But there was an inverse relationship between my results and the difficulty of the cases.

A few of my colleagues saw the same progression play out. Most of my colleagues did not. Most of them accepted that they would lose cases. They said it was okay to lose. They passed blame onto other factors.

It wasn't until I looked back that I saw the progression and understood why this happened.

What I saw is that most of my colleagues approached storytelling in a straightforward and formulaic way. I could listen to their opening statement and it sounded like one they gave a few months earlier. I could listen to their closing argument and see how they used the same emotion, analogies, and references. I understood why they failed as they approached it like a cookie cutter experience.

I did not.

I'm fortunate that a few of my mentors took me under their wing and showed me the right way. It wasn't the easy way but it was the right way. I felt like Mike Ross having his Harvey Specter.

Every case was unique and each story should be obsessed over to bring it to life. I'd see them in their offices working all hours of the day. On the weekends when I was at the office, so were they. On any given weekend there might be 15-25 lawyers out of over 200.

It was in those quiet moments I got to absorb everything they knew. I got to test ideas and approaches on them. I got to workshop everything with some of the most brilliant narrative minds I know.

Part of what makes storytelling effective is a deep understanding of persuasion and influence. What moves people? How do we get them to listen to us? Where is our psychological hook into their brain?

If you've ever watched the movie Inception, it's a damn good analogy for what it looks like.

We would sit there and think about how to get our ideas to take hold in the juries mind and have them feel like it was their own. We'd have to think in multiple levels to make it stick. We'd prepare and come up with the perfect strategy, knowing that when we got into the trial chaos would ensue and we needed to stay calm to get the job done.

What Leo's character says in that movie is true: "An idea is like a virus. Resilient. Highly contagious. And even the smallest seed of an idea can grow. It can grow to define or destroy you."

Most storytelling fails because most people don't understand the audience psychology, how to influence, and what it takes to pull that off.

What I see from entrepreneurs is cookie cutter storytelling. It's a word vomit of everything the entrepreneur wants to say instead of thinking about what the audience needs to hear. It's force feeding information to an investor instead of making them lean in and beg for more.

The simple truth is that the storytelling fails because there is no persuasion inside of it.

This is why I say that lots of people tell stories but very few people are storytellers.

Storytelling is about inspiring action and sadly few people do this well. The reality is that I did it poorly in those early days of my lawyer career. I was wandering and trying to figure out my way. I hadn't done the work it took to be great. I hadn't studied enough, tested enough, and become comfortable enough with the art form.

Some of the common flaws I see with entrepreneurs these days:

  • Too much education
  • Getting into features
  • Poor frame control
  • Zero or wrong analogies
  • Too long or too short
  • Not inviting a conversation
  • Too little future pacing
  • Not understanding both the micro and macro future
  • Delivery that feels boring, dry, or lacking confidence
  • Cheap storytelling "hacks" that reek of an amateur

Could I give more? Of course. I could write out 99 problems I see but these 10 are enough for today.

Maybe you realize the stakes for your business and are finally taking storytelling seriously. If that's true, well done. I challenge you to dig deeper. Are you really taking it seriously?

I'm built to hate losing. Absolutely despise it so when I lost some of those early cases in my career, I never wanted to feel that again. I also knew I wanted to try cases where the stakes where life and death. To operate in that world, I couldn't rest until I was the best. That stress and pressure plus internal drive is why I got here.

For you, you need to think about your future. Where do you want to be in 3 years?

What will it take to make that future a reality?

The idea has been planted. We will see if it takes hold and launches you to greatness.

RESOURCES for Founders and Storytellers

One more reminder to sign up for the free pitch practice event here.

Video on the difference between storytelling for entertainment and storytelling for business by looking at Sara Blakely and what she's been able to do.


"Cobb: Now, before you bother telling me it's impossible...

Eames: No, it's perfectly possible. It's just bloody difficult."

Learn more about the work we do with founders to raise capital ($545m to date) at Founder Fundraising.

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