Brand Storytelling

Brian Chesky: "One of the first things we do is figure out what the story is. The story often dictates the product. A story is a helpful way to develop a cohesive product." Define the narrative before finalizing features.

Find the five-second moment

Matthew Dicks: "Every story is about a singular moment—I call it five seconds. A moment of transformation or realization. 98% of the story provides context to make that moment clear." Identify the single moment of change.

Start in the middle of the action

Merci Grace: "Every pitch should start in the middle of the action, like Mission Impossible. Tom Cruise is always doing crazy shit before the actual mission. It gets attention." Skip the boring setup—hook them immediately.

Problems beat successes

Jason Feifer: "Success stories aren't interesting. Problem-solving stories are. Frame your story around a specific challenge you faced and the counterintuitive way you solved it."

You're Obi-Wan, not Luke

Mike Maples Jr: "The customer is the hero (Luke Skywalker), the founder is the mentor (Obi-Wan) providing the tools. Position your product as the lightsaber—the tool the hero needs."

Make it repeatable

Lulu Cheng Meservey: "Make it memorable. Make people want to say it of their own volition. Use analogies, colorful mental images, jokes. Replace adjectives with anecdotes people can repeat at dinner."

Paint emotional pictures

Camille Ricketts: "Effective storytelling paints an emotional picture of the vision. Convey the emotional quality of the mission, not just technical details, to enlist hearts and minds."

Hook, message, celebration

Christina Wodtke: "A beginning, middle, and end. Intrigue with a hook—a mystery, secret, or surprise. The middle delivers the message. Always end with success and celebration."

Memify your insights

Yuhki Yamashata: "The goal is 'memification'—synthesize insights so they're catchy enough for execs to cite in meetings. Use metaphors to explain complex concepts."

Questions to Help Users

• "Who is your audience and what do you want them to do after hearing this?"
• "What's the transformation or realization at the heart of your story?"
• "What problem did you face that others can relate to?"
• "Can someone repeat your core message at a dinner party?"
• "Are you the hero of this story, or is your customer?"

Common Mistakes to Flag

• Starting with your company - Start with the audience's problem or the world's change, not "We are..."
• Feature lists instead of stories - Stories are about change; lists are forgettable
• Hero syndrome - Position yourself as the mentor, not the hero
• Vague vision - "Making the world better" isn't a story; be specific
• No stakes - If nothing's at risk, there's no tension

Deep Dive

For all 50 insights from 30 guests, see references/guest-insights.md

Related Skills

• Positioning & Messaging
• Giving Presentations
• Fundraising
• Media Relations