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 synergies I see and some 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.
From verbal story to written pitch deck
How can founders translate these principles into the non-verbal format of a pitch deck?
There are two main factors to consider when moving from verbal storytelling to the pitch deck. First, a pitch deck is meant to intrigue the investor, to get them to lean in just enough so that they say, “I need to talk to this person.” What some founders try to do is cram their entire company story into their deck and explain absolutely everything. This glut of information doesn’t sing as well in a two-dimensional format. A pitch deck like this is overwhelming for investors–what you want to do is give them enough to make them want to meet you and learn more. Your pitch deck should create a cliffhanger for investors. Why do we keep reading a book after finishing a chapter? It’s often because the author has left us with a crucial unanswered question that compels us to read on and learn what happens.
Humans hate a lack of resolution–if you open a loop and don’t close it, people will hang on. It’s why we have “to be continued…” at the end of TV episodes or season finales. Too many founders try to close every loop in their pitch deck and give investors the entire picture up front. Unless that picture is in perfect alignment with what a particular investor’s looking for, there’s nothing to make VCs feel like they need to learn more.
The second important factor is for founders to remember that their headlines tell the story. I should be able to remove everything else from your pitch deck and be able to follow your narrative arc just from your slide headings. Another big mistake founders make is not devoting enough time and attention to these headlines because they assume all the additional information will speak for itself. But if your headlines don’t tell a story, they’re boring. And if they’re boring, investors will check out and you’ve lost the chance to get the meeting.The headlines in your pitch deck tell the story. Investors should be able to remove everything else from your pitch deck and be able to follow the narrative arc just from the slide headings. Click To Tweet
A tight pitch deck reflects your expertise
It’s more important than ever for founders to have a crystal-clear understanding of the essence of their value proposition. Hitting this note in a very tight, concise way will help founders break through the noise in the fundraising marketplace. The problem we’re seeing today is that founders are always putting more out there: they’re putting more information in decks, they’re making decks longer, and they’re overloading investors. Doing this doesn’t tell me that you know your business really well.
There’s a reason people love Naval’s tweets: they cut to the heart of every subject. Jack Butcher’s visuals do the same thing: he had constraints embedded in his images and that’s partly why Visualize Value took off. Founders need to follow these leads. They need to ask themselves how they can make their pitches super tight in order to reflect their expertise rather than adding more information in the hope of avoiding more questions.
DocSend Startup Index note: Robbie rightfully insists that pitch decks need to be as tight as possible. According to our Pitch Deck Interest Metrics, investors are spending around 2 minutes, 30 seconds reading pitch decks these days. A tightly-constructed deck with no extraneous information will make busy VCs want to schedule a meeting to learn more.
A tight pitch deck goes hand-in-hand with the idea that founders have to be able to do multiple things well in order to cut through the noise these days. They need to get to the very essence of their business and pitch it well, as I’ve mentioned, and they also need to field questions and be nimble and flexible in their interactions with investors. Having these tools at your disposal (and knowing when to use them) instead of putting everything in your pitch deck allows you to showcase different sides of yourself and paint a fuller picture of who you are as a founder. You’ll show that you can lead a team, lead investors, build a product, sell that product, and drive your company’s narrative. By contrast, cramming too much information into your pitch deck doesn’t let you show off any other skills–in the end, you’ll remain as two-dimensional as your deck.
Think of context like a flashback
An important tip for founders that will help them avoid overloading investors with information is to wait for your audience to give you permission to contextualize your ideas and story. Founders often over contextualize when communicating with investors–this can happen in emails, pitch decks, or even during meetings. Rather than over communicating, you want someone to give you permission to go on.
The truth is that nobody cares about context when it’s provided up front. But here’s what can happen: if you remove the context from your story, you drop your audience directly into the material that matters most. If you do this effectively, your audience will ask, “How did you get here in the first place?” At this point, you get to provide all the context you want because your audience has just given you permission to share it.
Movies and television do a great job with this: they drop viewers into a scene, engage them, and then give a flashback explaining how they got there. But those flashbacks would have been boring as starting points! The same is true for a founder telling a story: when investors hone in on important “plot points,” it’s much likelier that they’ll want to know more about a founder’s background and how they arrived at their idea. This strategy will help founders turn one-way communication into actual conversations, and that’s exactly what you need to do to cut through the noise today.
For a step-by-step guide on putting these storytelling tips into action, download our pitch deck guide and templates.
At DocSend, we feature outside experts on our blog and in our Weekly Index newsletter to share unique and diverse perspectives from within the tech community. Have a story or advice to share with your peers? Join our Contributor Program.