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Pitch memo

Skill kalyvask/winning-writing/skills/pitch-memo

Agentic writting toolkit built from Glenn Kramon's Winning Writing at Stanford GSB and Rachel Konrad's cold-outreach guest lectures. 31 Claude skills, a browser Coach with span-level inline critic and refinement chat, plus a Chrome MV3 extension that runs the same critic in the Gmail side panel.

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npx -y skills add kalyvask/winning-writing --skill pitch-memo

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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."

SKILL.md

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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 paraphrase. Cite a specific number, don't say "significant."
  • A "secret about the future" belongs in the Why-Now section. (See tell-them-something-new.)
  • Address the strongest counterargument in Competition, not a strawman.
  • Adverb hygiene. No empty intensifiers ("very," "really," "actually"). Use style-tells --target adverbs.

Length

A pre-seed memo is typically 800–1,500 words. A seed memo can run 1,500–3,000. Anything beyond 3,000 means the founder is hiding something behind volume.

If you can't compress to 1,500 words at pre-seed, it's a thinking problem, not a length problem. Cut.

Output format

When invoked from scratch:

# [Company name]: [Tagline]

[3-line opener: a "secret about the future" about the market, then the company name, then what you do. Lead with the insight, not the credentials.]

## Problem
...

## Solution
...

[continue through all 15 questions in order]

## Highlights (TL;DR for the impatient investor)
- [Single most important number]
- [Single most important customer or partnership]
- [Single most important "why-now" data point]

## Closing
[2-3 sentences: what you're raising, what kind of investor you want, the small specific ask.]

When invoked to critique an existing memo:

  1. Score each of the 15 sections on (a) presence, (b) specificity, (c) BLUF
  2. Flag the weakest 3 sections — those are where investors will dig
  3. Rewrite the weakest one fully, leave the others as bulleted critiques
  4. Identify any of the 15 that are missing entirely — most early-draft memos skip Competition's graveyard, the moat, or the Why-Now

Common failure modes

  • Skipping the graveyard in Competition. Investors love founders who name dead startups in the space and explain why each died. Most memos pretend nobody tried this before.
  • Vague "why now." "AI is transforming everything" is not a why-now. A specific tech / regulatory / behavioral shift in the last 18 months is.
  • TAM theater. Listing a $50B TAM with no SAM derivation is a tell. Bottom-up beats top-down.
  • Vanity metrics. Total downloads, total signups, total impressions. Replace with retention or revenue.
  • No superhero origin story. Investors back people, not just markets. The team section without a founder arc is dead.
  • Trying to do too much at once. A memo that lists 4 product lines reads as unfocused. Pick the wedge; show the roadmap.

Companion skills

  • pitch-coach — covers the spoken pitch and the deck. Use both: memo first, then deck.
  • graveyard-historian — feeds the Competition section's graveyard
  • warm-intro-finder — produces the forwardable blurb that gets the memo in the right inbox
  • winning-writing-critic — final rubric pass before sending

The Constine litmus test

"It's very difficult to hide [weak thinking] in a memo."

Read your memo cold a week later. If you can't defend a claim in 30 seconds without checking your notes, the claim is decoration. Cut it or get the data to back it.

Keep looking

Skills are one crate of 328,083. Ordering is by how many stacks a row turns up in, so the top of any crate is what has actually been picked rather than what has the most stars.