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 as a courtroom litigator in Dallas, Texas. He served as an assistant district attorney and in private practice for 102 jury trials in all — 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 the 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 the mission to empower startup founders along their fundraising journeys by honing their ability to communicate and connect with investors, Founder Fundraising trains entrepreneurs to become "Chief Storytelling Officers.”
Read on for Robbie’s takes on creating a memorable opening hook, shaping a narrative, drafting a pitch deck — and staying grounded throughout the process.
Dare to dream
First things first: The “Founder story” (a personal narrative) and a “vision story” (the “what” and “why” of a company itself) 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. But most people (Robbie included) “probably don't want to spend the rest of [their] lives around lawyers,” he says. Although his first business built adtech for the law profession, he realized he wanted to think bigger.
“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. After he sold his adtech firm in late 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.
Own your story
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 — “how they feel and who they really are,” Robbie adds. “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.”
That tactic typically nets 20 to 60 minutes of content that can be burnished into a concise, evocative and unforgettable personal history.
The 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, the 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 appealing 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.
The founder story and the vision story should function as two standalone 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 their larger vision.
Making the transition between the two stories seamless is fairly easy. We’ve all been acculturated to cliffhangers in movies and TV. In the startup world, “we invite the investor to say, tell me more about that,” says Robbie. He thinks it’s a great way to “dismount” from one’s personal story and leap into pitching the company itself.
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.
“That 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.”
Next step: Slide on to the next meeting
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.
He is also the CEO of Fundingstack.com which is a platform for VCs and investment bankers to both raise capital and assist clients and their portfolio companies.
Users of these platforms have raised over $15 billion since 2016.
This article is based on an episode of Foundersuite’s How I Raised It podcast, a behind-the-scenes look at how startup founders raise money.