How Storytelling Can Help You Craft An Investor Pitch That Stands Out

By Nathan Beckord

Every superhero needs an origin story. Robbie Crabtree’s is just a bit more Atticus Finch than Spider-Man.

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

With a mission to empower startup founders along 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 takes on creating a memorable opening hook, shaping a narrative, and drafting a pitch deck, while staying grounded throughout the process.

Sharing your journey with investors

Your founder story

First things first: the “founder story” (a personal narrative) and the “vision story” (the “what” and “why” about a company) are two different things, says Robbie.

Robbie’s own founder story coalesced when he realized that courtroom litigation skills could be taught and polished public speaking can make all the difference when closing a deal. “Instead of living in the world of nightmares, which is where lawyers tend to live, I said, Why don’t we live in the future where dreams are being 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 observed 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 begin building strong, trust-based relationships.

Robbie advises beginning your founder story by identifying what makes you special. How did you get to the place you are now? Why do you care about the particular problem your product solves?

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

If you’re unsure where to begin, “start when you were ten,” he suggests. (Ten is the age that evokes childhood most to Robbie.) “Don’t type it; turn on a recorder, whether it’s video or an audio recorder, and just speak out your answer.” This tactic typically nets 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 be focused on what Robbie calls emotional storytelling. “The vision story paints the big picture,” he says. “A founder should not try to prove they are right.” Instead, Robbie explains, founders should pique investors’ curiosity and suggest something more profound: “What if I’m right?”

Ideally, you want a potential funder to imagine themselves in a powerful position: 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 unseasoned startup to an IPO and/or an epic exit. Inevitably, every founder will experience pushback, objections, and skepticism. The anecdote is to appeal to investors’ deeper motivations. If they didn’t want to make an impact (and make money), they wouldn’t be in the venture capital game. So make your pitch big, bold, and ambitious. “That’s how we get venture capitalists excited to join the journey,” Robbie notes.

Telling your two stories

The founder story and the vision story should function as two stand-alone stories that can be told independently, but Robbie recommends structuring them so they can also be told as one narrative. A founder’s origin tale should lead into an engaging account of the larger vision; making the transition between the two stories seamless is fairly easy.

Robbie explains that we are acculturated to cliffhangers in movies and TV, and in the startup world “we invite the investor to say, Tell me more about that.” He thinks it’s a great way to “dismount” from one’s personal story and leap into pitching the company itself.

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Perfect your deck: Crafting a winning investor pitch

A compelling pitch needs a well-crafted deck. However, Robbie warns against following a preset formula for this or any other aspect of fundraising. Every founder and every company is different, so cookie-cutter, fill-in-the-blank approaches usually fail. One founder might have a personal story that’s tied directly to their startup’s product or service. Another company might have a value proposition that’s very much of the current moment—an attention-grabbing “why now” appeal to investors.

However, Robbie has strong opinions about what a deck should (and should not) do:

Do: Start strong with an opening hook

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

Another deal-breaker: Anything that’s too difficult to understand on its own. “If the first slide doesn’t make any 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 biggest thing in fundraising is to stand out to cut through the noise.”

Do: Plant a flag

Early in the deck, use strong, attention-grabbing declarative statements, rhetorical questions, shocking statistics, traction numbers, or even quotes from customers.

Don’t: Attempt to appeal to everyone

“We need to create filters,” says Robbie. “If the story is for everyone, it’s for no one. There’s no way every investor should hear it and be like, This is amazing. That’s just not the reality.”

Do: Create intrigue

Every slide should invite investors to dig deeper: “Make me say, Tell me more,” Robbie recommends.

Don’t: Go too text-heavy

Decks that are too overloaded with text are a recipe for “fractured attention,” says Robbie. “When you’re also speaking, 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 story arc of your entire presentation. If you physically printed your deck and dropped it on the ground, Robbie says anyone should be able to pick it up and put it back in the correct order just from the headlines alone.

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

Although he admits that it’s a “highly opinionated approach,” Robbie prefers pitch decks to be used as a “follow-on tool.” The initial meeting between a founder and potential funder shouldn’t be a pitch. Instead, he says founders should equip investors to become their champions and let them do the storytelling as they move to the next stage.

Now that’s a pitch-perfect strategy.

About the Author

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

RELATED: How to Create a Winning Pitch Deck for Investors: Tips From a Presentation Coach

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