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Storytelling as a Craft: 5 Experts on How to Tell a Business Story That Actually Lands
If you’re a startup founder, you’re already telling stories all day, every day. Pitching investors, marketing your product, rallying your team—storytelling is the glue holding your startup together. The thing is, most founders wing it. But how you tell your story can make or break everything: funding, sales, team morale, brand perception.
We pulled together the best advice on business storytelling from the Review archives—less fluff, more actionable frameworks you can actually use. Think Oren Jacob (Pixar storyboarding OG) meets Arielle Jackson (First Round’s Marketing Expert in Residence).
Why Storytelling Actually Matters
Storytelling isn’t just for marketers or content teams. It’s the secret weapon for founders.
“Visionaries succeed because they communicate a confident, coherent plan that makes people feel safe,” says Tyler Odean, longtime Google product leader. “We trust them not because their vision is perfect, but because they have it under control.”
Andy Smith, startup marketer and storytelling coach, adds: “Logic and specs are fine, but emotion sells. Well-told stories cut through the noise, humanize your brand, and spark action.”
In short: if your stories suck, your business will too.
4 Steps to Level Up Your Storytelling
1. Nail the Purpose
What’s the goal of your story? Convince investors to write a check? Get top talent to jump ship from BigCo? Before you start, define the why.
Arielle Jackson: “It all starts with positioning. Know your audience, your strengths, your competition. People are busy—you have to know who you are and why they should care.”
2. Get Specific on the Audience
Once the purpose is clear, zoom in on your audience. Treat it like a product persona: who are they, what do they care about, what pain points does your startup solve?
Jackson’s starter questions:
- What makes your product/service different?
- Why do you do what you do?
- Who’s your broadest set of prospective customers, and who is your ideal?
- What pain points are they facing, and what emotions are tied to them?
- Who else is solving these problems, and how do you stack up?
3. Build a Story Structure
No one likes rambling. Every story needs a beginning, middle, and end. But you don’t have to be chronological—emotion drives engagement more than timelines.
Oren Jacob: “Take the room on a journey. Your control is in the narrative arc, not the exact order of events.”
Andy Smith: “Events should build emotionally. Don’t start at the beginning just because it’s convenient.”
4. Weave It All Together
Take Uber’s origin story: frustrated with taxis, founders create a private driver app. Purpose? Solve a real pain. Audience? Urban professionals fed up with hailing cabs. Structure? Clear problem → solution. Add conflict, a relatable main character, and bam—you’ve got a business story that sticks.
Expert Tactics to Make Your Story Stick
Run the Bar Test
Nicole Kahn, VP of Design at Carta: “Tell your story like you’re at a bar. Direct, engaging, no corporate fluff. If a stranger gets it in 15 minutes over a coffee or beer, you’re on the right track.”
Lean Into Authenticity
Don Faul, CEO of Crossfit: “Share your failures, shortcomings, and what you’re working on. Being vulnerable builds trust—trust gets things done.”
Commit It to Memory
Oren Jacob: “A pitch is a live performance. Know it so well it feels spontaneous. Reading slides? Already lost.”
Bottom Line
Storytelling isn’t optional. It’s a skill you can practice, refine, and weaponize to win investors, hire talent, and build a brand people care about. Nail your purpose, target your audience, structure your story, and deliver it with authenticity.
And remember, the best stories inspire belief—not just in the product, but in the founder behind it.
