Storytelling Tips for Pitching Investors

Your pitch is the most important story you’ll ever tell. Here are 8 tips to get started.

Hey gang,

While conducting research for #GreatFoundersWrite, I ran into Allison Byers, an entrepreneur and expert in raising venture capital.

She was generous enough to let me interview her on pitching investors. Follow Allison on Twitter and check out her company, Scroobious.

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Image source: bplans blog

Great pitch decks tell great stories. That makes Allison Byers a world-class storyteller.

Allison has been creating pitches, giving pitches, and coaching pitches for over 15 years. As a career entrepreneur, she has raised over $10M in venture capital for her startups.

Now her latest company, Scroobious, helps underestimated founders raise their seed and pre-seed rounds by focusing on their pitch.

“A pitch deck is the first step in fundraising. It’s what determines, in the eyes of the investor, if you are worth another meeting,” said Allison.

Scroobius teaches founders how to craft a clear and convincing story for investors. Here are 8 storytelling lessons for pitching investors from my interview with Allison:

1. Connect emotionally

Investors aren’t just investing in your business. They’re investing in YOU.

That’s why you need to share your personal story. Why did you start your company? What does it mean do you?

“An investor wants to know what ties you to your business,” said Allison. “They have to know you’re so passionate about it that you're not going to run away. You're going to stick with it.”

Allison tells the founders to open their pitch with their origin story. Make it’s personal, powerful, and authentic.

“Investors are also humans,” she said, “Connect with them on an emotional level.”

2. Vivid examples > numbers

“The goal of a first pitch is to convince someone you're worth another meeting—another conversation—not to get a check.”

Investors heavily scrutinize financial projections of early-stage founders—and especially women, Allison has found. That’s why she tells founders to NOT include financial projections if they are still pre-revenue.

Instead, use vivid examples to make the opportunity come to life. Talk about your specific customers and market opportunity.

“First convince the investor there’s a problem worth solving,” she said.

Save the financial projections for a later conversation.

3. Spheres of Context

Investors, generally speaking, are generalists. Founders, on the other hand, are experts in their domain.

This is something many first-time founders forget, and it comes at the cost of clarity.

“A lot of what I teach in my framework and in my workshops,” said Allison, “is how you clearly communicate what you do to an investor, who is a generalist and does not have your domain expertise.”

When writing, I use this phrase often: Spheres of context. It applies here, too.

Make sure you pitch investors with concepts and terms that fit in their sphere. Avoid acronyms that could be confused for something different.

4. Simplify

Investors aren’t impressed by big words. They want simplicity.

“Many founders think that talking in very high-tech or industry-specific terms will help them because it makes them seem smarter,” said Allison. “But it actually hurts them.”

Allison has a favorite exercise to force simplicity: Give your pitch to your grandmother and a fourth grader. Then ask them to explain what you do.

If they can’t clearly explain your business, your pitch is too complicated. Simplify.

5. Make Slides “Glance-able”

One of my favorite writing tips is “write for the skimmer.” Use headers, bold type, and bullets to make your writing easy to read quickly.

The same is true for your pitch deck. Allison calls it “making your slides glance-able.” Your slides need to be simple and descriptive enough that investors can understand them with just a glance.

“A person can’t read words and listen to what you’re saying at the same time. So the goal of your slide should be to communicate your information as quickly as possible,” said Allison.

How to make your pitch deck slides glance-able:

  • Use descriptive slide titles, not just “Problem” and “Solution.”

  • Make one point per slide.

  • Use infographics and illustrations, not blocks of text.

6. Write out your speaking notes.

Writing forces you to think clearly. That’s why Allison tells founders to write down their speaking notes.

“Even if you're not going to memorize it, the act of writing out what you're going to say for a slide is incredibly helpful.”

7. Take a bottom-up approach to calculating market size

Venture capital is all about hitting home runs. Since ~80% of investments fail to turn a profit, investors need at least one of their companies to reach a 10-100x valuation.

That’s why market size is such a critical piece of information. Does your startup have the opportunity to grow by 10-100x?

There are three ways to calculate market share:

  • Total Addressable Market (TAM) = All of your potential customers if you had 100% market share.

  • Serviceable Addressable Market (SAM) = Realistic percentage of TAM that you could reach or who could actually buy your product.

  • Serviceable Obtainable Market (SOM) = Realistic percentage of SAM that will become customers in the next 1-2 years.

Many first-time founders start with TAM and work their way down to actual customers.

If we capture just 0.5% of the Total Addressable Market, our company will make $7.5 BILLION a year.

This approach is highly speculative. It’s based on secondary information and not rooted in the reality of your business.

Instead, take a bottom-up approach by starting with your Serviceable Obtainable Market (SOM). This is the percentage of the market you can reasonably sell to in the next 1-2 years.

“[Bottom-up] is a very business-specific approach that starts with your customers,” said Allison.

The bottom-up approach will help you create more accurate and realistic projections. It also shows investors you understand your market.

8. Answer the question, “Why should I care?”

You may get frustrated when others don’t “see” your vision. But as a founder, your #1 job is to convince people that your business is legit.

“You need to separate yourself [from your business] enough to think like a generalist and not think like the expert that you are.”

Take off your founder hat and look at your business as an outsider. What do you do? Why should people care?

Keep asking yourself this question until you find an answer that resonates.

Tell stories like your business depends on it (because it does)

As a founder, your pitch is the most important story you’ll ever tell. It requires practice, patience, and guidance from people who have done it before.

These 8 tips barely scratch the surface of what it takes to create a great pitch. Allison Byers has spent years building curriculum on this subject. To learn more, follow her on Twitter and check out Scroobious’s resource section.

If you’re a founder looking for help pitching and raising capital, sign up for Scroobious’s Pitch It Plan.


If you find this story helpful, please hit the 🖤 and share with one person. Thank you!