Business How storytelling can help you create an investor pitch...

How storytelling can help you create an investor pitch that stands out


By Nathan Beckord

Every superhero needs an origin story. Robbie Crabboom‘s is just a little more Atticus Finch than Spider-Man.

Before he launched Founder FundraisingRobbie spent seven years in courtlitigating everything from gang and cartel violence to capital murders and child abuse. That’s when he started using the term “competitive storytelling,” which is now the name of Founder Fundraising’s parent company. As any fan of courtroom drama can attest, lawyers on both sides need to convince with facts as well as make emotional appeals.

With a mission to support startup founders through their fundraising journeys, Founder Fundraising trains entrepreneurs to become chief storytelling officers by honing their ability to communicate and connect with investors.

Read on for Robbie’s take on creating a memorable opening hook, crafting a story and crafting a pitch deck, all while keeping both feet on the ground throughout the process.

Share your journey with investors

Your Founding Story

For starters, the “founder story” (a personal story) and the “vision story” (the “what” and “why” about a company) are two different things, says Robbie.

Robbie’s own founding story came together when he realized that litigation skills can be learned in the courtroom and that polished public speaking can make all the difference in closing a deal. “Instead of living in the world of nightmares that lawyers often live in, I said: Why don’t we live in the future where dreams are built?he explains, adding that founders and venture capitalists are both big dreamers. In 2020, he began sharing his hard-won insights with other entrepreneurs, and Founder Fundraising was born.

In his experience, Robbie has noted that founders don’t leverage their own journeys nearly enough. That’s a big mistake, because most investors bet on the founders themselves, not just the products or companies. He sees a compelling origin story as a way to connect with investors And start building strong, trust-based relationships.

Robbie advises starting your founding story by identifying what makes you special. How did you get to where you are now? Why do you care about the specific problem your product solves?

“Those seem like very simple questions, but they allow a founder to do some really deep and meaningful work,” he says. Ultimately, the founder’s story illustrates three facets of a person’s personality and background: how they think, how they see the world and their hearts, and “how they feel and who they really are,” explains Robbie. “It creates a level of trust between the founder and the investor.”

If you’re not sure where to start, “start when you were ten,” he suggests. (Ten is the age most reminiscent of childhood for Robbie.) “Don’t type it; turn on a recorder, be it a video or an audio recorder, and just say your answer.” This tactic typically produces 20 to 60 minutes of content that can become a concise, evocative, and unforgettable personal history.

Your vision story

Your second story is the “vision story,” which should focus on what Robbie calls tell emotionally. “The vision story paints the big picture,” he says. “A founder should not try to prove that he is right.” Instead, Robbie explains, founders should pique investor curiosity and propose something deeper: “What if I am right?”

Ideally, you want a potential financier to feel in a position of power: on the right side of history. The one who saw it coming. The one who gambled and won.

But emotional storytelling isn’t a step-by-step blueprint for the journey from an unseasoned startup to an IPO and/or an epic exit. Inevitably every founder will experience setbacks, objections and skepticism. The anecdote is to appeal to investors’ deeper motivations. If they didn’t want to make an impact (and didn’t want to make money), they wouldn’t be in the venture capital game. So make your pitch big, bold and ambitious. “This is how we get venture capitalists excited to join the journey,” Robbie notes.

Telling you two stories

The founder story and the vision story should function as two self-contained stories that can be told independently, but Robbie recommends structuring them so that they can also be told as one story. A founder’s origin story should be initiate a compelling account of the larger vision; making the transition between the two stories seamless is quite easy.

Robbie explains that we have become accustomed to cliffhangers in movies and TV, and in the start-up world, “we invite the investor to say: Tell me more about that.He thinks it’s a great way to move away from someone’s personal story and start pitching the company yourself.

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Perfect your deck: Make a winning pitch to investors

A compelling pitch needs a well-made deck. However, Robbie cautions against following a preset formula for this or any other aspect of fundraising. Every founder and company is different, so approaches to fill in the blanks usually fail. A founder may have a personal story directly related to their startup’s product or service. Another company may have a value proposition that is very timely – an attractive “why now” that appeals to investors.

However, Robbie has strong opinions on what a card game should and shouldn’t do:

Do: Start strong with an opening hook

Think of the first slide in your pitch deck as priceless real estate. Your opening salvo should be irresistible – and fast. When we speak, we have about three to five seconds to pique an audience’s curiosity.

Another deal breaker: anything too hard to understand on its own. “If the first slide doesn’t make sense to me, I’m done,” says Robbie.

Don’t: Stick to the problem/solution binary

The classic problem/solution structure is just too commonplace. “[It] makes you sound like every other founder out there,” Robbie notes. “And the most important thing in fundraising is standing out to cut through the noise.”

Do: Plant a flag

Use strong, eye-catching statements, rhetorical questions, shocking statistics, traction numbers, or even customer quotes early in the game.

Don’t: Try to address everyone

“We have to make filters,” says Robbie. “If the story is for everyone, it’s for no one. It is impossible that every investor would hear it and say: This is amazing. That’s just not the reality.”

Do: Create intrigue

Each slide should invite investors to dig deeper: “Make me say, Tell me moreRobbie recommends.

Don’t: Go too text-heavy

Decks that are too overloaded with text are a recipe for “distorted attention,” says Robbie. “If you’re also talking, the human brain can’t keep up.”

Presenting your pitch deck

The headline (or title) of each slide should do its part to express the storyline of your entire presentation. If you physically printed out your deck and dropped it on the floor, Robbie says anyone should be able to pick it up and put it back in the right order just by the headlines.

The very first slide usually contains a startup’s one-line description or tagline, which is “super important to really establish,” adds Robbie. “One of my favorites. . . was ‘We’re like Mary Poppins, but for space.’ You wouldn’t know exactly what it is, but it’s enough to want to know more.” (If you’re also curious, the UK-based company helps manufacturers deliver goods via a parachute-like device — “whimsical and true to whoever the founder is,” says Robbie.)

Although he admits it’s a “very idiosyncratic approach”, Robbie prefers to use pitch decks as a “follow-on tool”. The first meeting between a founder and potential funder should not be a pitch. Instead, he says founders should equip investors to become and leave their champions them do the story as they move to the next stage.

Now that is a pitch-perfect strategy.

About the author

Nathan Beckord is the CEO of Founder suite. com, which makes software for startups raising capital. Nathan is also the CEO of, a new platform for VCs and investment bankers to both raise capital and help clients and portfolio companies. Users of these platforms have raised more than $9.7 billion since 2016.

RELATED: How to craft a winning pitch deck for investors: tips from a presentation coach

Shreya Christina
Shreya has been with for 3 years, writing copy for client websites, blog posts, EDMs and other mediums to engage readers and encourage action. By collaborating with clients, our SEO manager and the wider team, Shreya seeks to understand an audience before creating memorable, persuasive copy.

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