The real reason your message doesn't deliver

How to leverage audience-centric messaging

January 23, 2023
min read

Happy Sunday Chief Storytelling Officers.

A founder I work with sent me a message on Saturday. You see he was playing around with chatGPT and asked this question, "what are examples of unorthodox executive roles?"

The first answer...Chief Storyteller.

It went on to say the Chief Storyteller is responsible for crafting the company's narrative and communicating its vision to internal and external stakeholders.

Well said chatGPT.

Let's dive into making you the Chief Storyteller.


DEEP DIVE: Speaking Your Audience's Language

Everyone has a boss.

We’ve spent our entire lives beholden to one party or another: our parents, our teachers, our supervisors. Even as entrepreneurs—the section of the population that is supposed to “be your own boss”—we must answer to customers and investors.

What we often forget, though, is that the buck doesn’t stop with VCs. They have bosses that they’re beholden to also—their LPs.

Part of the reason that’s forgotten is because it’s historically not common practice for VCs to discuss their investors or finances. It’s kind of like eating at a restaurant and not knowing where the chefs source their food.

That’s changed for some funds—and farm-to-table restaurants—but for most, LPs are still the wizard behind the curtain.

But I assure you, the LPs are there, and whether you realize it or not, they’re watching. And not taking their needs into account when delivering your pitch often results in a failure to land funding.

There are levels to this game and it goes deeper than most founders realize. They've never studied the way venture capital works. They've never studied the way the wealthy in the world operate. They've never studied the shadows where power and influence live.

As a trial lawyer, I watched as cases would get handled differently if certain influential figures were involved. As a prosecutor, I saw how politicians played the game to play dirty but keep their hands clean.

Fortunately I left that world behind and now the shadow games aren't as nefarious but it's important to know how to speak the language of VCs so they can speak the language of their LPs. Because I can guarantee one thing, VCs are always thinking about their LPs and how to raise that next fund.

Here are some things you need to keep in mind to keep the bosses happy:

Know where LPs and VCs are Coming From

In order to effectively communicate during a pitch, everyone needs to be speaking the same language.

I see this all the time in business. The CFO’s language is centered around money, the COO’s language is centered around logistics, and the CXO’s language is centered around UX. Sure, there are places where each of these languages intersect—just as there are English cognates in French—but with so many different priorities in the room, it can go pear-shaped fast.

When it comes to funding, you need to take it upon yourself to speak the VC’s language—and, by proxy, their LP’s. It is not their responsibility to come to you; you must come to them.

Language choices like "double click", "dig deeper", and "I'm curious" show up on every founder-investor call I've reviewed. I bring this up to remind you that the words people use matter and should be incorporated into your own vocabulary if you want to connect.

So where do you start?

Start by understanding what both VCs and LPs need. In the current market, many LPs are either pissed or scared. They don’t want to send the money they committed to the VC fund back when times are good. And VCs don’t want to upset their LPs or make them look bad.

Also remember how VCs get paid. Usually, they get a percentage of the AUM plus carry. This explains why VCs want to deploy capital and get winners. They do that with the goal of raising a NEW, BIGGER fund—because the bigger the fund, the more money for the firm—and for them personally.

This isn't evil. This isn't bad.

Wanting to make a ton of money is perfectly fine. In fact, I want to and so do the founders, executives, and investors I work with. Simply put, money creates freedom and opportunity.

How you feel about money is how it feels about you.

Understand these two critical things: VCs answer to LPs. And the VCs get paid from raising future funds.

The big takeaway here? If you want to get that VC’s capital, you have to figure out how you can help the VC succeed with those two goals. Think about it like Jerry McGuire: help me, help you.

Practice Audience-Centric Communication

Now that you know your audience isn’t just the VC partners in the room and that you need to come to them, you must tailor your messaging accordingly.

This is called audience-centered speaking, when you build your message around the audience’s experience, knowledge, and goals. By taking these elements into account, you have a much better chance at connecting with your audience.

The first step of crafting an audience-centered presentation is by executing on exactly what I shared with you above. Understand their language, and incorporate it into your pitch.

Then decide how you can make sure the VC will look good when talking about the deal with the fund’s LPs. Your goal is always to make the VC feel like they’re going to miss out if they don’t get on the train now. How can you translate that message into the language of an LP?

A word of warning: this does NOT mean that you attempt to pitch a game of inside baseball. The fundamentals of storytelling still apply here. All the things I continually talk about—your origin story, your framing, your closer—are INFINITELY more important than chucking out a bunch of terms you think will appeal to LPs.

This is why I first developed what I call the Competitive Storytelling Framework back when I was a trial lawyer and then coaching the national mock trial team at SMU Law School. It was also the core piece of the edtech I built that was acquired back in 2020.

It's 5 questions to answer before any pitch, presentation, or talk.

  1. What's your goal?
  2. What emotion does the audience need to feel?
  3. What's your hook?
  4. What's your theme?
  5. What's your dismount?

The first two questions give you the strategy for talking to investors.

The last three questions give you the tactics to make it memorable and intriguing.

The key here is to find the balance. How can you demonstrate a basic understanding of your audience’s language without sounding like an old person pretending to be a teenager?

At the end of the day, it’s important to realize that just because the VC partners are the ones hearing the pitch, it doesn’t mean they have the final say. Everybody’s got someone to answer to, and as long as you keep that audience in mind and speak their language, you’ll have a better chance at success.

The real magic comes when you understand the way the game is played and then deliver the perfect emotional experience for investors to believe in you and your vision.

Remember, perfect storytelling comes down to a transfer of 3 things.

A transfer of emotion. A transfer of confidence. A transfer of conviction.

ChatGPT won't ever be able to do that. You have to step into that role and become the Chief Storyteller.

You have to win the game of Competitive Storytelling.

RESOURCES for Founders and Storytellers

Audience-centric communication is really at the heart of any good pitch. For more tips on how to craft one, check out this great Duarte blog on the topic.


I love breaking down tv and movie scenes as they relate to storytelling, selling, and pitching. We've touched on Mad Men and The Dark Knight the past few weeks.

What's your favorite scene or real talk that you'd like me to break down in the coming weeks to pull out all the lessons you can take from it?

Want to become a world-class storyteller and fundraiser? You can learn more at our website and apply to talk with our team about how we can help. (it's not cheap)

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