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/pitch-memo

Drafts and critiques a text-first investor pitch memo for pre-seed and seed founders, structured around the 15 questions every investor asks. Use as an alternative or complement to a pitch deck — memos are faster to iterate, harder to hide weak thinking inside, and serve as the

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winning-writing
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$ npx -y skills add kalyvask/winning-writing --skill pitch-memo --agent claude-code

How it fires

How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/pitch-memo

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The summary Claude sees to decide when to auto-load this skill.

Drafts and critiques a text-first investor pitch memo for pre-seed and seed founders, structured around the 15 questions every investor asks. Use as an alternative or complement to a pitch deck — memos are faster to iterate, harder to hide weak thinking inside, and serve as the

SKILL.md

pitch-memo.SKILL.md
name: pitch-memo
description: Drafts and critiques a text-first investor pitch memo for pre-seed and seed founders, structured around the 15 questions every investor asks. Use as an alternative or complement to a pitch deck — memos are faster to iterate, harder to hide weak thinking inside, and serve as the script for walking through a deck in a meeting. Triggers on "pitch memo," "investment memo," "fundraise memo," "memo for investors," "pitch document," "alternative to deck," "memo not deck."

Pitch memo

Source: Josh Constine's *Fundraising & Pitch Deck Guide* — specifically his 15-question memo template — plus Kramon's BLUF rule, Konrad's "tell me a secret about the future," and the existing `pitch-coach` framework.

Why a memo (not a deck)

For pre-seed and seed companies, a memo can outperform a deck:

  • **No design wrangling.** No fiddling with slide layouts or hiring a designer.
  • **Pretty design can hide weak thinking; a memo can't.** If the founder can't write the 15 answers cleanly, they're not ready to pitch.
  • **It's the deck script.** Even if you eventually build a deck, the memo is the narrative spine — write it first, design slides to support it, not the other way around.
  • **Decks leave investors with questions; memos answer them upfront.** Less follow-up email cycle.

A memo replaces a deck for: pre-seed, founders who think in text more than imagery, and any raise where you're competing on *substance* over *presentation*. A memo complements a deck for everyone else.

The 15 questions (Constine)

Every investor asks the same 15 things. A memo that answers all of them in order is the most efficient possible pitch artifact.

1. Company name

Ideally, if you hear it you can spell it; if you read it you can pronounce it. You should be the top Google or App Store result for your name + a relevant keyword.

2. Tagline

One-line description. Plain English. No buzzwords. *"AI co-pilot for notaries."* / *"Forward-deployed engineers, but as software."* / *"Stripe for healthcare data."*

3. Problem

  • What's wrong with the world?
  • How acute is the pain?
  • Who specifically has it? (A must-have for a small niche beats a nice-to-have for a wide market.)
  • Show emotional resonance — your own first-customer story or a named person's story, not abstractions.

4. Solution

  • Core functionality of the product
  • How did you come up with it (origin story matters)
  • How does it make a few people's lives a lot better, or a lot of people's lives a little better?
  • One screenshot or a short demo video walking the most common use case
  • Why is this *exponentially* better, not linearly better?

5. Big vision

  • If you succeed, how does the world change?
  • What's the path from beachhead → $10B company?
  • Why is this your legacy?
  • Why do you want to spend the next 10 years on this?

6. Team

  • Specific roles + companies for each founder (not just logos)
  • LinkedIn for each
  • Why are you the best team in the world to tackle this?
  • The "superhero origin story" — the personal arc that means you'll never quit
  • Co-founder dynamic (this is what kills early-stage startups)
  • Advisors only if they're high-quality — max 2 or 3, never lean on their credibility

7. Market size

  • Serviceable Addressable Market — bottom-up, not vague TAM
  • TAM only as a layer for adjacent products you'd launch later
  • How fast is the market itself growing?
  • How much are people spending on or losing because of the problem today?

8. Business model

  • How do you earn money?
  • Pricing model
  • Margin
  • What's your affordable customer acquisition strategy?

9. Go-to-market / customer

  • Who specifically do you sell to (named segments, not "SMBs")?
  • Demographic
  • Channels — direct, partnerships, PLG, etc.
  • Who on the team owns sales/growth?
  • Marketing strategy
  • How does the product grow itself?

10. Traction

  • Current state — customers, users, revenue, growth rate
  • Day-30 / Day-90 retention
  • Dollar and logo retention
  • Top customers + spend + room for expansion
  • Pipeline
  • Focus on the **north-star metric**, not vanity metrics

11. Competition

  • Direct startups attacking the same problem
  • Big incumbents who could move in
  • Status quo / old-school way customers solve this today
  • 2×2 matrix or differentiation checklist
  • **The graveyard** — what have you learned from past failures in this space? (See `graveyard-historian` skill.)
  • Why is this a winner-take-all or winner-take-most market?
  • Your defensible moat / accruing advantage as you grow

12. Why now

  • Tech, behavior, macroeconomic, or regulatory shifts unlocking this
  • Why couldn't this have been built 5 years ago?
  • What changed in the last 18 months that makes the timing work?

13. Raise history

  • Total raised to date, round by round
  • Lead investors, angels, valuations, SAFE vs. priced
  • Most helpful people on the cap table
  • Burn rate and runway

14. Raise

  • How much you're raising
  • SAFE or priced round
  • Ballpark valuation cap (or no, if you'd rather investors price it)
  • What you're looking for in your investors (operator help, recruiting, GTM, regulatory expertise, etc.)

15. What's next

  • Hiring plan
  • Key hires that complement founders' skillsets
  • Specific milestones you'll hit before raising the next round
  • Common targets: $200K ARR before seed, $1M before A, $9M before B, then doubling

Writing rules — apply across all 15

These come from `points/` and apply to every section of the memo:

  • **BLUF.** Each section opens with the conclusion, not the buildup.
  • **Specific over abstract.** "47 of 100 PMs interviewed" beats "many people we talked to." Use `vividness --mode noun-level`.
  • **Banned jargon.** No synergy/leverage/drive/strategize/empower/at the intersection of. Use `style-tells --target jargon`.
  • **No em-dashes in the deliverable.** Use commas, periods, colons. (See `style-tells --target em-dashes`.)
  • **Show, don't tell.** Quote a customer with attribution, don't paraphras
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Ships withwinning-writing

31 Claude skills for cold outreach, op-eds, pitches, press inquiries, bios, exec memos, performance reviews, spoken-delivery talks, fact-checking, and reply-rate tracking.

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Repo: kalyvask/winning-writing

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