What 102 Jury Trials Can Teach You About Fundraising

What's going on founders and storytellers.

Welcome back to The Storyteller’s Playbook! In this issue, we’ll take a deep dive into the lessons I learned during my law career trying 102 jury trials that can turn you into a great fundraising founder. I’ll also share some recent examples of masterful storytellers—and how their craft propelled them into fame.

This one goes deep and if you get through it all, you might just look back after your next round and remember the day you read this...

I’m glad you’re here. Let's get after it.

— Robbie

DEEP DIVE: 5 Fundraising Lessons You Can Learn From Trial Lawyers

I spent the first seven years of my career as a trial lawyer. During that time, I tried 102 jury trials (handling thousands of cases), starting with misdemeanors and progressing into violent felonies—murder, child abuse, you name it. When I wasn’t in the courtroom debating my own cases, I sat in the gallery listening to other lawyers, picking up tips and tricks that I could test out the next day.

Many of the cases became national news, television episodes, or full blown series. It was a wild seven years.

Over the years, the lessons I learned from those cases made me very good at my job. I loved fighting for victims in a courtroom. Losing wasn't an option with these stakes. But it's a dark world and one that I still feel to this day. I still think about the cases, the victims, and their families.

And once I left the courtroom, I realized those same lessons could be applied to fundraising and help founders craft the perfect story and strategy to raise venture capital.

Here are five lessons I learned as a trial lawyer that can propel your fundraising skills from good to great:

Lesson 1: Develop a Poker Face

I remember one trial during my career when my partner cracked a joke during witness testimony. At the time, I thought I’d hidden my chuckle well, but after the case, the jury scolded me for laughing during such a serious case.

I spent hundreds of hours developing a poker face after that.

As executive coach Teri Citterman points out in a Forbes article, a leader’s demeanor is critical to success. In the modern business world, employees, clients, and prospective investors demand more emotion, authenticity, and transparency from leaders. When your nonverbal cues express happiness, confidence, and satisfaction, it transfers that feeling to your audience. But when things go wrong and it’s written on your face, the results can be disastrous.

Richard Nixon learned this the hard way during the 1960 presidential debates, when he faced off against the handsome Massachusetts Senator John Kennedy on national television. While those who listened to the debate on the radio felt Nixon had a strong command of the debate, the voters who watched it on television claimed Kennedy had won, citing Nixon’s dour expression and profuse sweating as off-putting. Some historians attribute Kennedy’s charming demeanor as the key to his narrow victory. Two years later, Nixon wrote in his memoirs: “I should have remembered that ‘a picture is worth a thousand words.’”

If you know you’re the type of person to wear your emotions on your sleeve, it’s important to understand how you come across to your audience. I don’t care how silly it sounds—study yourself in the mirror or film your pitch and watch it back. Examine your body language and be critical of how it presents. Do you hunch or furrow your brow? Do you litter your pitch with sighs and glances at the ceiling?

It might not sound fair, but your audience judges EVERYTHING. The more mindful you are of this, the more polished you’ll come across.

Lesson 2: You’re Never Fully Ready

I don’t care how much prep time you put in, there’s always going to be an unexpected twist.

That’s okay.

One of my very first mentors told me the key to trying cases is being comfortable with the chaos. He said it’s never about being “fully ready”—at a certain point preparation just becomes a form of procrastination.

In the courtroom, there are dozens of ways a lawyer can buy more time. One of the many reasons people hate lawyers is that they’re skilled at stalling. You’d be amazed at how many ways an effective lawyer can subtly tell the judge they’re not ready to proceed.

One part of the fundraising process that’s difficult to prepare for is the Q&A section. No matter how flawless your presentation is, it’s impossible to completely predict what a potential investor will ask (although I've got a nice list compiled at this point).

That’s not to say prep time isn’t important. Many founders I coach fail to understand that the fundraising process is a marathon with a 40 meter dash at the end. They focus so much on the sprint that they try to condense the endurance part leading up to it. Michael Jordan famously said: “Champions do not become champions when they win an event, but in the hours, weeks, months, and years they spend preparing for it.” Hard to argue with the greatest.

The key here is to prepare but also be comfortable with the fact that you won’t ever be FULLY ready. Find comfort in the chaos.

Lesson 3: Be Flexible and Adaptable

As I said above, the funding process is a marathon combined with a sprint at the end. Remember, that each round plays out like this. Each part of the process requires a different set of skills that you must showcase in order to be effective.

It was the same for me during trials. My approach during jury selection was friendly, intimate, and open-minded. My focus during my opening statement was performance and connection building. During my closing arguments, I emphasized expertise, conviction, and black-and-white thinking.

Since I had a different goal during each of these phases, I adapted the way I spoke and interacted. I altered my tone, my word choice, and my body language to better achieve my purpose.

Don’t fall into the trap of being a static, one-dimensional founder. Think about how your pacing, your volume, and your movements can impact the way your message is received. Do you want to build ethos by instilling confidence and trust? Speak slowly. When you want to emphasize a point, speak louder; when you want the audience to lean in, speak softer.

Think of the process as a symphony: there are many movements that create a larger piece and elicit different emotions from the listener.

Lesson 4: Confidence Creates Trust

Early in my career, I lost a misdemeanor domestic abuse case. When I talked to the jury afterward to find out what went wrong, they told me they thought the defendant was guilty, but my voice just didn’t sound like I believed what I was saying. I failed the victim, and from that day forward I made a promise to myself that I’d never let that happen again.

Not only did I study the way other lawyers presented their cases, I looked at how the greatest achievers of all time got to where they were. The common thread? Confidence.

One such example is pro surfer Kelly Slater, whose ascent to the top of the surf world is nothing less than inspirational. Slater often talks about his journey and how exuding confidence carried him to where he is today. “Find what you’re good at and go for it,” Slater said. “Don’t let anything or anyone tell you differently. You have to be your best critic and you have to be your best believer.”

Every founder deals with an element of fear as they’re building their business, but allowing that fear to drive your decisions results in you avoiding doing the things you know you should. As leadership coach Mark Green writes in his book, Activators, you must be aware of the fact that you are unconsciously motivated to favor fear. It’s the foundation of many decisions, but that’s okay. Trust yourself in the face of fear, and don’t let your audience see you sweat.

Lesson 5: Storytelling Wins

When you’re a trial lawyer and you don’t have a good story to tell, the jury makes up facts. It sounds crazy, but it’s 100% true. According to an article from the American Bar Association, when jurors can’t understand complicated evidence or can’t agree on facts, they rely on “stored scripts” from their own lives in order to understand the case and reach a verdict.

When a lawyer tells a great story, however, the jury stays focused. I made it a mission to watch the best storytelling lawyers every week I wasn’t in trial and learn from them.

Remember how I said earlier that you need to be flexible and adaptable in different situations? The one thing that stayed constant for me in every phase of a trial—jury selection, opening statement, closing argument—was storytelling.

So too is storytelling critical in the business world. I’m telling you—if storytelling helped me send child abusers to prison for life, or helped me defend a man wrongly accused of murder, it can absolutely help you raise venture capital.

That’s because storytelling actually affects us on a biological level. A 2011 scientific study found that listening to a narrative activates several different parts of the brain—especially during the emotional parts of the story. In another study, Princeton psychology professor Uri Hasson discovered that when you listen to a story unfold, your brain waves actually start to synchronize with those of the storyteller.

RESOURCES for Founders and Storytellers

I mentioned this briefly in last week’s newsletter, but I’m still reeling from Dave Chappelle’s new special on Netflix. It’s a 40-minute speech he gave at his former high school in Washington, DC, where a theater was supposed to be named after him. Believe what you will about Chappelle’s stances on controversial topics, it’s an absolute masterpiece. I don’t say this lightly: he’s the greatest storyteller alive. Plenty of others agree, including comedian Carter Morgan, who wrote this lengthy analysis for Medium breaking down exactly why. David Perell gave a similar stamp of approval on this Twitter thread.

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Harry Potter is the #2 best-selling book of the last 25 years, second only to The Bible. And as Nathan Baugh points out in this breakdown thread, author JK Rowling used one storytelling framework for the entire series. Storytelling doesn’t have to be complex in order to be good. In fact, the simpler it is, the better.

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MAYA Capital closed a $100 million Fund II. Two female founders, huge results from Fund I, and ready to keep deploying into great LATAM founders with a focus on female founders. I love seeing this. Great investors are out there ready to back great founders.

FINALLY...

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