The Secret Ingredient to the Perfect Pitch: How to Tell a Compelling Story

We see so many startups struggle to raise a round. They think they’re doing everything correctly when they pitch, but there’s a subtle yet critical flaw -- they’re pitching, but not telling a compelling and believable “story.” A story has a strong arc with a captivating, well-connected, and (convincing) beginning, middle, and end. Thinking of your pitch as a story will help you shape and deliver something that is so much more powerful and convincing than just a “pitch.” Naturally, people love stories and connect with them. 

Making your pitch into a compelling story is easy once you understand the tweaks your deck and delivery need. Keep reading or watch the dose below for Steve’s easy-to-follow framework that will make your pitch a story that will draw in prospective investors. 



1. Think about your company’s story like a fairytale

Approach your early-stage pitch deck like a fairytale. In the earliest stages, startup pitches have a lot in common with fairytales. They start with some form of “Once upon a time…” and end with some version of “and they lived happily ever after.” In this context, a startup’s happily ever is often an IPO, acquisition, or generally dominating their respective market.


2. Make sure the story flows

Now that you’re thinking about your pitch like a fairytale another problem may come up. The core components of most startup pitch decks do not flow and build like a true “story.” A fairytale starts, builds, and flows across chapters. As you make your way through the chapters the story develops and holds together. What does it mean for a story to “hold together?” Well, in your typical fairytale the prince does not get his head cut off in chapter 3, then marries the princess in chapter 5. Yet, we see that level of inconsistency in many startup pitches. How so? Foundational slides like your problem, solution, total addressable market, competition, and go-to-market strategy slides are not conveying a consistent message. As a result, they don’t tell a convincing story. 

You may think this doesn’t apply to you. Test your pitch’s consistency using the examples. 

“You show your solution slide. Does it actually solve the problem as stated? What about your market sizing slide? There’s one problem...it doesn’t accurately measure the market size of the specific customers having the problem as stated.”

Now you see, your fairytale “pitch deck” is falling apart at the seams. Think critically about how your deck flows, whether or not your story holds together, and what core components must be consistent to support the story your deck is telling.


3. Starting your story

As you think about telling your story, choose carefully where you want your story to begin. What’s the objective of a compelling story opener? Obviously, you want investors to connect to you and your story as quickly as possible. Even if they don’t personally experience the problem you address, you want to bring them into your world so they’ll be able to relate to your prospective customers. If you don’t think investors are capable of understanding your customers’ needs, we can tell you what they will understand: traction. Traction provides evidence that there is a real need for your product or service.

Here are some examples of where to start your story:

  • You may want to start with your “back story.” Where did the idea come from? Did the problem impact you, or someone you know, personally? A concise explanation of your backstory may be a compelling way to start.

  • Do you think talking about your traction is the best way to start? You could start with something like this, “I want to tell you about our company. We are so excited to say that in our first 12 months organizations like Google, Amazon, and L’Oreal all signed as early customers.”

  • Or, do you think the most compelling way to start your story is by presenting the characters in your “play?” Yes, we’re alluding to your team slide. Steve mentions that he isn’t a fan of team slides at the start of your pitch. However, if your team is spectacular and traction is light, we understand that, in that case, investors ultimately are betting on the team. Then, it makes sense to highlight the team to draw them in.

  • At Dreamit, we generally believe that startups should begin by explaining the big and urgent problem they’re solving. Weave this into your pitch by providing the backstory on how you came upon this problem and why it’s important to you. If an investor doesn’t believe you are solving a major problem, your story will have a weak foundation.

  • One more idea for those with solid traction. You can start your story with a “flashback” summary as your first slide. This will immediately intrigue investors. For how to do this effectively, see our Dreamit Dose on flashback slides here.


4. Drip in traction to demonstrate credibility

So you start telling your story and you go through your slides like the “chapters” of a book. As you tell it, make sure to lightly drip in traction as you cover the core components of your pitch deck. Otherwise, your audience may start to think you really are telling a fairytale. 

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Are you covering the problem? Make sure you mention how many companies you’ve talked to about the problem, and how painful and urgent the problem is. When you mention these points, the problem will come alive for your investors even if they don’t experience it themselves.

Are you going over the solution? Mention who your key early adopters are. 

Are you covering your go-to-market strategy? Make sure you mention the evidence that supports why this strategy will be effective. 

Each of these points makes your story more credible, and your pitch more compelling as a result. Quick note, dripping traction does not mean the points are actually written on your slides. They may just be covered in your voiceover as you present.


5. Use case demo

You have a great beginning, you’ve worked through your core slides and dripped traction into your pitch. Now you need the story to come alive. It’s time for your demo. It may just be screenshots, a picture of your product, or maybe showing your physical product. This can be your opportunity to solidify your story, but you’ve got to be careful here. 90% of startups fall out of storytelling as they demo their product. They STOP telling a story and start on a feature-by-feature rundown of their product. That’s a big mistake. Go here to check out our Dose on use-case-based demos. It’s crucial that you do a use-case demo that weaves in a “day in the life” concept and uses an “actors in a play'' approach to talking about how people use your product.


6. End on a crescendo

As you come to the end of your story, make sure that you hit a few final critical points.

What’s the big vision for your company?

How is this just the beginning?

How is your company going to “live happily ever after?”

As a final note, when discussing your “happily ever after” we advise avoiding discussing getting acquired. Your vision should be something along the lines of your company dominating the market with your superior product and brand.


By Alana Hill, Securetech Associate at Dreamit Ventures

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