Writing & Speaking: The Pitch DeckSequoia Skeleton · Problem-Solution Arc · Why Now · Airbnb 2009

Skeleton first, flesh later. Sequoia compresses a funding story into ten slides, each answering one unavoidable question in the investor's head — and the order is the argument. From "who are we" to "why now" to "why you."

The value isn't the "template" — it's that the skeleton forces you to think in the investor's order of attention. Meeting anything new, a mind silently runs a queue: What is this? Whose pain? Why now? How big is the pool? Why you? Sequoia's ten slides arrange that queue into a chain you cannot skip — drop a link, and the listener's mind snags exactly there.

• Fundraising pitches, internal budget asks, new-project proposals, promo packets ("problem — solution — why now — why me" holds everywhere)
• Don't open with architecture or résumés — the investor doesn't yet know what you do, so why care about your stack?
• Don't scramble the order: solution before problem leaves the listener asking "a cure for what?"
• Don't fill ten slides like a form — the skeleton is a narrative order, not a table

Sequoia Capital, Pitch Deck Template / Writing a Business Plan (sequoiacap.com) · Reid Hoffman, the "Annotated Pitch Decks" series on LinkedIn

Before you introduce the solution, make the problem ache. No conflict, no story; no pain, your solution is merely a "better" — not a "must." Investors buy painkillers, not vitamins.

Without conflict the story is silent. In a pitch, the conflict is the problem that keeps the audience squirming in their seats.

A pitch's energy comes from the gap between the pain of the problem and the relief of the solution — the wider and more concrete the gap, the more indispensable the solution feels. Most pitches fail because they rush to show off the solution and gloss over the problem; the audience never builds desire, and even a great answer earns only a polite "nice." McKee names the truth: what people remember isn't the solution, it's the conflict it resolved. So write the problem real — who, how often, how much it hurts — then let the solution arrive like a long exhale.

• Any pitch, project proposal, persuading a leader to change the status quo, the hero text of a landing page
• The vitamin illusion: the problem is only "could be better," not "hurts now" — no one funds "better"
• Too abstract ("low efficiency, poor experience") — no person, no frequency, no number, no ache
• Jumping to the solution before the pain lands — the gap was never built
• Exaggerating the problem into fiction — once a knowledgeable listener catches it, all trust collapses

Robert McKee, Story: Substance, Structure, Style (1997); HBR interview Storytelling That Moves People (2003) · Chip & Dan Heath, Made to Stick, the "Concrete" chapter

Don't open with your product — open with an irreversible change in the world. That change creates winners and losers, and your solution is the only path to the winning side. It answers the sharpest question in the room: why now, and not three years ago or three years from now?

"Why now" is the most underrated, most fatal slide in a pitch. A change — in technology, regulation, behavior, or cost curves — opens a window that didn't exist five years ago and will close five years from now; the window itself is the momentum. Dissecting top decks, Andy Raskin distilled a five-step strategic narrative: name the change, reveal the winners and losers, paint the promised land, frame features as the "magic gifts" for getting there, and close with evidence. The genius is in the order: make the audience anxious about the change first, and your solution becomes a cure rather than a sales pitch. Same root as Thiel's "what important truth do very few agree with you on?"

• Fundraising pitches, category-creating launches, driving a major internal strategy shift
• "Why now" absent — the investor instantly fires back, "why didn't someone do this three years ago, and why won't it be too late in three?"
• The change is too small or too obvious ("everyone's busier these days") — it can't carry high stakes
• You paint the promised land but leave the audience/customer out of it — they're spectators, not the hero
• Use with care: manufacturing a "world-changing shift" in a mature, stable market just sounds grandiose

Andy Raskin, The Greatest Sales Deck I've Ever Seen (Medium, 2016) · Peter Thiel, Zero to One (2014), the chapter on "secrets" and contrarian truths

Airbnb's famous 2009 seed deck had no fancy design, yet it's treated as a textbook. For one reason only: one slide says one thing; one number serves one judgment. Problem, solution, and market each compress to a page, understood in under three sentences.

Watch how Airbnb perfected the first few slides. The Problem page lists just three pains. The Solution page is one line of positioning — "book rooms with locals, rather than hotels" — plus three benefits (save money, make money, cultural connection). The Market page doesn't shout "trillion-dollar blue ocean"; it narrows through three numbers: 2 billion trips worldwide → 560 million booked online → 10.6 million serviceable short-term rentals. Every page passes the "grasp it at a glance" test. This is the first three principles made real: a clear skeleton + a true pain + restraint beats any animation.

• Any outward-facing material that must "land at a glance": pitches, one-pagers, landing pages, external updates
• Cramming several points onto one slide — eyes and ears fight for bandwidth, and none of it sticks
• Sizing the market in adjectives, not numbers ("huge," "blue ocean") — adjectives can't help an investor judge
• Copying its "plain design" but not its "structure and restraint" — plainness isn't the goal; clarity is

Airbnb 2009 Seed Pitch Deck (public; dissected repeatedly by Slidebean, TechCrunch) · Geoffrey Moore, Crossing the Chasm positioning template ("For …who…, X is a…that…, unlike…")