Bringing courtroom skills to tech

Before coming to tech, I worked as a trial lawyer on over a hundred jury trials. I also coached the national mock trial team at SMU law school. The world of a trial lawyer is all about competitive storytelling: whoever tells the best story tends to win the case. Understanding this was crucial when I was trying high-stakes cases like violent felonies or capital murders. I knew I needed to tell my story in a really impactful and meaningful way. To do this effectively, you have to understand human psychology, game theory, delivery dynamics, creative narratives, and even brain chemistry. All these elements go into compelling storytelling: my job required me to understand how people connect to stories and why they work.

In 2019, I began to realize that there was a need for these skills in the startup world and in particular for fundraising. For example, a closing argument is basically the same as a pitch: when you’re in a crucial meeting with investors, you’re trying to close the deal by convincing VCs that funding you is the right thing to do. Several months after my co-coach and I first discussed this opportunity, I began to get inbound leads from entrepreneurs who had read my articles and tweets on the overlap between trying cases and pitching a startup. They wanted my help crafting their fundraising narratives.

Here are some similarities I see and some actionable tips I have for founders:

Communicate why you care

When working with founders on how they talk about their companies, the most important question I try to have them answer is: Why do you care? That is, what is the story that made you want to build this business? Being a founder is inherently hard, stressful, and risky. What’s more, many founders could have chosen easier paths. I want to identify why founders chose to do something really difficult–what’s driving this?

Sometimes the story is personal, and other times it’s about a friend or family member going through a difficult problem. Or perhaps a current event triggered them, making them think “I can fix that! I know how to do this.” We have to nail this underlying story in order to effectively communicate why a founder cares about their business and why they’ll run through walls to solve their problem.

When I first begin working with a founder, they often give a fairly anodyne “problem plus solution” response to these questions. It almost sounds like a resume–there’s no life to the story that will hook investors and make a company stand out from all the others. But this is exactly what makes stories so valuable. People say having opposable thumbs is what makes us human, but I think it’s the ability to tell stories: opposable thumbs let us hold onto things, but stories tell us what’s worth holding onto. And if you can’t communicate that well, there’s no way to connect with investors.

The three elements of an elevator pitch

When you’re creating your story, there are three pieces that fit into an effective verbal pitch. I call these the Three Ps: purpose, passion, and potential.

Your purpose is an expression of your problem/solution and why they matter today. This is the most acute pain point.

Your passion communicates why you’re the right person or team to keep pushing forward through any challenges. Why will someone trust that you won’t give up?

The third piece of the story, potential, is where you set up your ideal future state. This is where founders often make mistakes: they minimize how large their potential actually is. What founders need to do is set the biggest, grandest, boldest vision possible for their business. However, I often get a lot of pushback against this idea since founders think they won’t achieve their loftiest goals. But it doesn’t matter! Setting a big, bold goal will force you to take steps to get there. Even if you come up short, you will have gotten further than if you had set a smaller goal.

Here’s an example: let’s say the TAM in a product is realistically $40 billion. A founder might undercut themselves and claim that the TAM is only $10 billion because it seems more achievable to them. This is the wrong attitude to adopt. Or consider Elon Musk: he sold the SpaceX vision by claiming we were going to put people on Mars and terraform the planet. We’re nowhere close to that scenario right now, but because people bought into that ambitious vision we now have SpaceX taking satellites into orbit or the Starlink internet system. These achievements came as a result of trying to get to Mars–had Musk set his sights lower we’d be even further behind.

Focusing on the Three Ps takes you through a narrative arc: people see that there’s a problem to be solved and that you’re the person to guide them through it. People want the safety of a guide but they also want a sense of adventure and excitement, and this is where your grand potential vision comes in.

Read the full post here for tips on going from from verbal story to written pitch deck, creating a A tight pitch deck that reflects your expertise, and how to think of context like a flashback.