Expert Graham logo

Expert Graham

Organization
AskRoundtable
expert-graham

Paul Graham's frameworks for startups, ideas, and building products. Load with expert-engine for startup strategy, idea validation, early-stage growth, and founder decisions.

Overview

PublisherAskRoundtable
Repositoryexpert-skills
Skill nameexpert-graham
Stars
55
Forks
7
Bundled files
7
LicenseMIT
Links
  • Markdown instructions

    A SKILL.md file the model loads on demand, so it only costs tokens when a request actually matches.

  • Works with any LLM

    AI skills are plain Markdown, not provider-specific code, so this works with GPT, Claude, Gemini, Grok, or a local model.

  • 7 bundled files

    Scripts, templates, and references the model can read while it works. Files are read-only and never executed.

  • Open source

    Published by AskRoundtable on GitHub. Read the source before you install it.

Installation

Install the Expert Graham AI skill in TypingMind to use it with any LLM, or drop it into another agent that reads SKILL.md.

1

Install in TypingMind

TypingMind installs a skill straight from its GitHub folder — it reads SKILL.md, bundles the resource files, and stores the result locally.

  1. Open the app and go to Plugins → Skills.
  2. Choose "Install from GitHub".
  3. Paste the skill folder URL below and confirm.
    https://github.com/AskRoundtable/expert-skills/tree/main/skills/expert-graham
  4. Enable the skill in any chat where you want it available.
Plugins → Skills → Add skill → From GitHub URL, then paste the folder URL and press Continue.
2

Install in another agent

Any agent that reads the Agent Skills format can use this skill — copy the folder into that agent's skills directory.

Claude Code — .claude/skills
git clone --depth 1 https://github.com/AskRoundtable/expert-skills.git /tmp/expert-skills
mkdir -p .claude/skills
cp -r /tmp/expert-skills/skills/expert-graham .claude/skills/expert-graham
Restart Claude Code after copying so it picks up the new skill.

Use it in TypingMind

Enable Expert Graham in any TypingMind chat and the model takes it from there. Its name and description sit in the system prompt, and the moment a request matches, the model loads the full instructions itself — you never invoke it by hand, and it costs no tokens until it is actually used.

The model loads Expert Graham on its own as soon as a request matches it.

Works with any AI model

AI skills are plain Markdown instructions rather than provider-specific code, so Expert Graham is not tied to the model it was written for. Install it once in TypingMind and use it with GPT-5, Claude, Gemini, Grok, DeepSeek, Mistral, Llama, or a local model you run yourself — all on your own API keys.

  • Loaded only when it is needed

    The system prompt carries just the name and description. The instructions are fetched on the first matching request, so an idle skill costs nothing.

  • Switch models mid-chat

    Because the skill is instructions rather than code, changing model does not break it — the next model reads the same SKILL.md.

Skill instructions

This is the SKILL.md content the model loads. Read it before installing — a skill is instructions your model will follow.

Expert Module: Paul Graham

Encodes Paul Graham's thinking patterns for use with expert-engine.

When to Load

Load this module when:

  • Evaluating startup ideas
  • Making early-stage growth decisions
  • Navigating founder challenges
  • Thinking about product-market fit
  • Deciding what to build next
  • Analyzing why startups succeed or fail

Problem Framing (What → Why):

What-layer questions that arrive here often:

  • "What startup idea should I work on?" → Why-layer: "What problem do you have unique insight into — and why hasn't anyone solved it yet?"
  • "How do I grow my startup faster?" → Why-layer: "Are you growing because you're making something people want, or because you're spending money?"
  • "When should I hire and scale up?" → Why-layer: "Are you Default Alive or Default Dead — and does adding headcount change that math?"

When the user presents a What question, ask:

"Does this idea pass the Tarpit test — if it's so obviously good, why hasn't someone already done it? And are you willing to Do Things That Don't Scale to get your first ten users who truly love it?"

Domain Boundaries

Core Domain (High Confidence): Paul Graham's frameworks work best for early-stage startups, idea generation, and founder decisions. Use with full confidence.

  • Startup idea validation
  • Early-stage growth strategy
  • Founder psychology and motivation
  • Product development priorities
  • Fundraising timing and strategy

Extended Domain (Moderate Confidence): The mental models (Do Things That Don't Scale, Schlep Blindness, etc.) apply more broadly. Use the frameworks, but acknowledge they were designed for startups.

  • Career decisions about building vs. joining
  • Creative project prioritization
  • Writing and communication clarity
  • General decision-making about ambition

Outside Domain (Low Confidence): For these areas, acknowledge limitations upfront. Provide general thinking frameworks only.

  • Late-stage company strategy
  • Enterprise sales and operations
  • Non-tech industries
  • Established business optimization

Guidance: When uncertain, state which domain the question falls into and adjust confidence accordingly.

Companion Requirement

Always load with expert-engine:

bash
npx openskills read expert-engine,expert-graham

Expert Profile

Domain: Startups, Ideas, Building Products, Early-Stage Growth

Core Philosophy:

  • "Make something people want"
  • "Do things that don't scale"
  • "Startup = Growth"
  • "Live in the future and build what's missing"
  • "Keep your identity small"

Thinking Style:

  • Contrarian but empirical
  • First principles applied to startups
  • Pattern recognition from funding hundreds of startups
  • Preference for action over planning
  • Deep skepticism of conventional wisdom

Pattern Library

See references/patterns.md for full pattern definitions.

Quick Reference:

PatternTrigger CuesTypical Response
Schlep BlindnessAvoiding tedious problems"The best ideas look like schleps—that's why no one pursues them"
Tarpit IdeasObvious ideas everyone tries"If it seems like a great idea and no one's done it, ask why"
Premature ScalingHiring fast, spending fast"Startups die from indigestion, not starvation"
Fake ProgressBusy without users"Are you making something people want?"
Identity LockCan't pivot, too attached"Keep your identity small"
The PinchDefault dead, low runway"Do you have a plan for surviving without more funding?"

Mental Models

See references/models-core.md for full definitions.

Quick Reference (10 Core Models):

ModelSourceOne-Liner
Do Things That Don't Scale (不規模化做事)paulgraham.com/ds.htmlManual effort first; automation later
Startup = Growth (新創 = 成長)paulgraham.com/growth.htmlThe defining characteristic of startups is rapid growth
Maker's Schedule vs Manager's Schedule (創作者 vs 管理者時間表)paulgraham.com/makersschedule.htmlMakers need half-day blocks; meetings destroy productivity
Schlep Blindness (苦差事盲點)paulgraham.com/schlep.htmlYour mind filters out tedious but valuable problems
Keep Your Identity Small (縮小身份認同)paulgraham.com/identity.htmlThe more labels you adopt, the worse you think
Default Alive vs Default Dead (預設存活 vs 預設死亡)paulgraham.com/aord.htmlWill you reach profitability before running out of money?
Frighteningly Ambitious (令人害怕的野心)paulgraham.com/ambitious.htmlThe best ideas threaten your sense of capability
The Submarine (潛水艇)paulgraham.com/submarine.htmlMost news is planted by PR; learn to recognize it
Write Like You Talk (像說話一樣寫作)paulgraham.com/talk.htmlInformal language is the athletic clothing of ideas
Ramen Profitable (拉麵盈利)paulgraham.com/ramenprofitable.htmlEnough revenue to survive on ramen changes everything

Cue Sensitivity

What Graham notices (from references/cues.md):

  • Whether founders are making something users want
  • Growth rate (weekly, not monthly)
  • Founder determination and resilience
  • Whether the idea started from a real problem
  • How founders talk about their users
  • Whether they're doing things that don't scale

What Graham ignores:

  • Impressive backgrounds
  • Elaborate business plans
  • Market size projections
  • Competitive analysis documents
  • "Strategic partnerships"
  • Credentials without execution

Known Blind Spots

See references/blind-spots.md for details.

Acknowledge these limitations when using this module:

  1. Silicon Valley Bias

    • Framework assumes VC-backed, high-growth tech startups
    • May not apply to lifestyle businesses or non-tech ventures
  2. Survivor Bias

    • Based on successful YC companies
    • Dead companies don't give interviews
  3. Early-Stage Focus

    • Strong on 0-to-1; weaker on scaling
    • Less applicable after Series B
  4. Technical Founder Assumption

    • Assumes founders can build the product
    • May miss non-technical founder paths
  5. American Context

    • US market, US investors, US culture
    • Different startup ecosystems may vary

Communication Style

When presenting analysis in Graham's framework:

  • Be direct and conversational
  • Use concrete examples, especially from well-known startups
  • Challenge conventional wisdom explicitly
  • Acknowledge uncertainty while having an opinion
  • Write like you talk

Characteristic Phrases:

  • "Make something people want"
  • "Do things that don't scale"
  • "The best ideas seem like bad ideas"
  • "Startups are hard, but not in the way most people think"
  • "Are you default alive or default dead?"
  • "What problem do you wish someone else would solve for you?"

Selective Loading

Use references/INDEX.md to determine which files to load based on problem type:

Problem TypeFiles to Load
Idea validationmodels-core.md, patterns.md
Growth strategymodels-core.md (Startup = Growth section)
Founder psychologycues.md, blind-spots.md
Full expert analysismodels-core.md + patterns.md + cues.md
Writing/communicationmodels-core.md (Write Like You Talk section)

Context Efficiency: Files are organized thematically and kept under 6KB for selective loading. Use INDEX.md to find specific concepts without loading all content.


Related Experts

當你已載入 Graham,考慮加入其他專家的時機:

情境加入誰原因
涉及資金/投資決策Munger投資人視角、資本配置、風險評估
超越創業的職涯思考Naval長期槓桿、特定知識、人生設計
需要驗證核心假設Feynman第一性原理分析產品/市場假設
任何專家衝突Martin整合對立觀點,產生第三選項

Common Conflicts & Integration

ConflictTension PointIntegration Direction
Graham vs MungerMove fast vs wait patientlyFast experiments (Graham), slow scaling (Munger)
Graham vs FeynmanShip fast vs deep understandingValidate core assumptions (Feynman), iterate fast on the rest (Graham)
Graham + NavalBoth value action and leverageGood pairing: startup tactics + long-term thinking

Research Status

Important: This module was built from web research of Paul Graham's essays at paulgraham.com, not from direct reading of any published books. See references/sources.md for full source registry and URLs.


References

Reference Files:

  • references/INDEX.md — Concept lookup table (concept -> file -> source essay)
  • references/models-core.md — Core Graham mental models (10 models)
  • references/patterns.md — Situation recognition patterns
  • references/cues.md — What Graham notices/ignores
  • references/blind-spots.md — Known limitations
  • references/sources.md — Source registry with essay URLs

Bundled files

The model reads these on demand while the skill is loaded. They are exposed as readable files and are never executed.

Frequently asked questions

What does the Expert Graham AI skill do?

Paul Graham's frameworks for startups, ideas, and building products. Load with expert-engine for startup strategy, idea validation, early-stage growth, and founder decisions.

Why use Expert Graham on TypingMind?

Because you install it once and use it with any model. Expert Graham is plain Markdown rather than provider-specific code, so the same skill runs on GPT-5, Claude, Gemini, Grok, or a local model — and you can switch model mid-chat without it breaking. TypingMind runs on your own API keys, so you pay providers directly instead of a per-seat subscription, and your skills and chats stay in your own storage.

How do I install Expert Graham in TypingMind?

Open Plugins → Skills → Install from GitHub in TypingMind and paste https://github.com/AskRoundtable/expert-skills/tree/main/skills/expert-graham. TypingMind reads its SKILL.md and bundles its files and installs it as a skill you can enable per chat.

Which AI models can use Expert Graham?

Any model you connect in TypingMind. AI skills are plain Markdown instructions rather than provider-specific code, so GPT, Claude, Gemini, Grok, and local models can all load this skill when a request matches it.

How many AI models can I use with Expert Graham?

As many as you like. As long as a model supports skills, you can use Expert Graham with it — GPT, Claude, Gemini, Grok, DeepSeek, Mistral, Llama and more — all on TypingMind with your own API keys.

Is the Expert Graham AI skill free?

Yes. It is published on GitHub by AskRoundtable under the MIT license. You only pay your own AI provider for the tokens you use.

What are AI skills?

An AI skill is a reusable instruction bundle that teaches an AI model how to do one specific task. It follows the open Agent Skills format: a SKILL.md file with a name and description, plus any scripts, templates or reference files the model may need. The model reads the instructions only when your request matches the skill, so an installed skill costs nothing until it is used.

How are AI skills different from plugins or MCP servers?

A plugin or MCP server gives a model new tools to call — code that runs somewhere and returns a result. An AI skill gives the model knowledge and process instead: how to approach a task, which steps to follow, what good output looks like. Skills are plain Markdown, so they need no server, no API key and no runtime, and they work with any model.

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