Warmth And Competence
Audits a draft on Susan Fiske's two-axis model of social judgment — warmth (do I like and trust this person?) and competence (do I respect this person?) — and rewrites the lines that signal the wrong thing on either axis. Implements Kramon's hardest rule: "show competence AND warmth in a single sentence." Use when a draft reads cold-but-impressive (high competence, low warmth — the "consultant tr…
Yourself Story
Drafts and critiques bios, LinkedIn About sections, intro slides, "tell me about yourself" interview answers, and personal-essay openers using Adam Bryant's 500-CEO research and Lauren Weinstein's warmth+competence frame. Different from pitch-coach (which is product-shaped) and cold-email-coach (which is recipient-shaped). This skill is for the format where you ARE the subject. Use when writing a…
Sent Mail Outcome Tracker
Read the user's recent cold-outreach sent mail, look up which messages got replies, classify reply sentiment, and produce an outcome report that surfaces what the responders had in common. Use when the user says "did my cold emails get replies," "what's my reply rate," "sent-mail outcomes," "track outcomes," or "/sent-mail-outcome-tracker." Requires a connected Gmail MCP. Read-only. Never contact…
Humanize
Makes a draft read like a real human typed it — adds asymmetry, light contractions, and (rarely) one safe typo. Use only when a draft is technically correct but reads polished beyond plausibility, when the user wants to "rough it up," "make it more human," or "less AI-clean." Does NOT run on high-stakes writing (see "When NOT to humanize"). Triggers on "humanize," "rough it up," "less polished,"…
Bluf Rewriter
Reorganizes a memo, email, status update, or report so the bottom line is up front. Implements Kramon's BLUF (Bottom Line Up Front) rule. Use when a draft buries the lede, opens with context instead of conclusion, or builds up to the point with "organ music." Triggers on "BLUF," "lede," "buried," "memo," "status update," "exec summary," "TL;DR.
Op Ed Coach
Drafts and critiques op-eds, opinion pieces, and LinkedIn long-form posts using Glenn Kramon's framework, Katie Kingsbury's NYT Opinion guidance, and Nicholas Kristof's storytelling rules. Use when the user is writing an op-ed, an opinion piece, a Substack essay, a LinkedIn long-form post, or pitching one to a publication. Triggers on "op-ed," "opinion piece," "essay," "column," "pitch to NYT," "…
Performance Review Coach
Drafts and critiques performance reviews using Glenn Kramon's seven rules from Stanford GSB's Winning Writing course. Use when the user is writing an annual review, mid-year check-in, self-review, 360 feedback, peer review, or any written feedback for an employee, boss, partner, or themselves. Triggers on phrases like "performance review," "annual review," "self-review," "write up my feedback for…
Voice Update
Update `context/voice-and-style.md` or `context/about-me.md` from one of three sources. Manual (user dictates a single new rule, sample, or career fact). Memory (batch pull from Claude Code's auto-memory in `~/.claude/projects/<slug>/memory/`). Sent-mail (analyze the last 20-50 sent Gmail messages and propose updates from observed patterns). Always proposes diffs and requires per-file approval; n…
Recipient Research
Builds a research dossier on a cold-outreach target before drafting. Pulls LinkedIn, podcasts, blog posts, news, portfolio (if VC), and any specific personal details that would let an email feel hand-written rather than templated. Use when the user says "I want to email X" or "research Y before I write to them" or "build a dossier on Z." Triggers on "research," "dossier," "before I email," "backg…
Compression
Cuts a draft to a target word count without losing substance. Two modes behind one skill. target-count hits a specific number (200 for a cold email, 500 for an op-ed, 6 for a product summary). redundancy catches the specific failure where a phrase says what the verb or context already implied — "going forward" after a future-tense verb, "as I mentioned earlier," "reduce so they are smaller." Impl…
Cross Model Review
Independent second-model gate for cold emails before send. Must run on a DIFFERENT model than the one that drafted (e.g., draft on Opus, review on Sonnet — or vice versa). Acts as a binary pass/fail gate, not a regrade or rewrite. Names the specific failure mode from a 14-mode catalog (strategy / personalization / posture). Always surfaces the most likely counter-question the recipient will reply…
Speech Coach
Drafts and critiques speeches, talks, keynotes, lightning talks, demo-day pitches, all-hands updates, conference presentations, wedding toasts, and any spoken-delivery piece using Glenn Kramon's 12 wowing-the-crowd rules from Stanford GSB's Winning Writing. Use when the user is preparing a talk, presentation, keynote, panel opener, board presentation, all-hands, town hall, demo-day pitch, toast,…
Headline As Claim
Rewrites section titles, slide titles, op-ed headlines, email subject lines, and chapter headings from category labels into bold arguable claims. Implements Constine's "punchy slide titles that tell the story" rule and Kingsbury's NYT Opinion guidance that headlines should make a bold claim, not a neutral description. Use when the user has titles like "Product," "Market," "Background," "Why this…
Feedback Rephraser
Rewrites blunt downward or peer feedback as "what I like plus what I would like," focused on the work rather than the person, ideally phrased as a question. Use whenever the user is drafting a performance review, a Slack message to a report, a 1:1 talking point, an HR conversation script, a peer-review comment, or any line where they're tempted to criticize a colleague directly. Triggers on "give…
Pitch Coach
Drafts and critiques business pitches, investor decks, mission statements, and personal pitches using the 7-part pitch framework, S.H.I.T., and the six-word test. Use when the user is writing a VC pitch, a deck narrative, a "tell me about yourself," a LinkedIn bio, a one-pager, a founding story, or any pitch about themselves or their company. Triggers on "pitch," "deck," "investor," "mission stat…
Style Tells
Scrubs the three surface tells that make prose feel AI-generated, padded, or jargon-heavy. Three targets behind one skill, picked via the --target arg. em-dashes (default off in cold email / memo / Slack, max one per page in op-eds), adverbs (the -ly and intensifier pile), jargon (the Silicon Valley / consultant kill-list plus AI-tell phrases). Use when the user says "kill the AI tells," "scrub j…
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 script for walking through a deck in a meeting. Triggers on "pitch memo," "investment memo," "fundraise memo," "memo for…
Winning Writing Critic
Grades any draft against the full Winning Writing rubric (Kramon + Konrad + Kingsbury) and rewrites it. The orchestrator skill — invoke when you don't know which specialized skill applies, when the user just says "review this" or "make this better," or when the draft spans multiple forms (e.g., a pitch email that's also kind of an op-ed). Triggers on "review," "critique," "feedback," "make this b…
Dealing With Reporters
Drafts and reviews answers to reporter questions, on-the-record statements, crisis-comms responses, and press-inquiry replies. Implements Andrew Ross Sorkin's 11 rules (taught with Kramon at Stanford GSB) plus AP attribution definitions for off-the-record / background / deep background conversations. Use when a journalist is calling, when a story is about to break, when a competitor has just been…
Cold Email Coach
Drafts and critiques cold emails using Rachel Konrad's 10 rules, Heidi Roizen's mailing rules, and Danny Hertzberg's six elements. Use whenever the user is writing a cold email, LinkedIn DM, intro request, hiring-manager outreach, VC pitch email, or any unsolicited message to someone with more power than them. Triggers on phrases like "cold email," "reach out to," "intro request," "DM," "outreach…
Winning Writing
Mode-aware writing critic. Distilled from Rachel Konrad's Stanford GSB "Winning Writing" course (spring 2026), the 10 rules of cold outreach, Heidi Roizen's mailing rules, and live class critiques. Loads a rule catalog (rules/catalog.json) and a mode definition (rules/modes.json) at invocation. Use whenever drafting or critiquing a cold email, outreach message, LinkedIn intro, exec memo, personal…
Warm Intro Finder
Finds the human bridges between the writer and a target — mutual contacts, alumni networks, ex-colleagues, podcast connections, board overlaps — and ranks them by how likely they are to make a useful introduction. Different from connection-finder (which finds "like you" content hooks). This one finds *people* who can vouch. Use whenever the user is about to send a cold email and hasn't checked wh…
Irrelevant Detail Killer
Cuts cinematic details that don't serve the main point. The opposite move from vividness. Vividness adds sensory detail; this skill removes detail that's vivid but distracts from the argument. Use when a narrative paragraph has impressive sensory texture (sounds, colors, weather, mechanics of an unrelated scene) that the reader has to push past to get to the point. Triggers on "eliminate irreleva…
Ent Idea Coach
Help the user harvest insights from research and convert them into a falsifiable bet (Stage 01). Pushes back on wishes, ideas masquerading as insights, and consensus thinking. Use when the user has finished discovery / RDI and is trying to commit to a specific opportunity, or when they say "I have an idea" and need to test whether it's actually an insight.
Ent Design Partners
Help the user identify, qualify, sign, and manage design partners — 2–5 early B2B customers who co-create the MVP. Pushes back on tire-kickers, big-logo traps, and free-pilot programs. Use when the user is preparing to sign design partners, qualifying a candidate, structuring the partnership terms, or troubleshooting an existing design-partner relationship.
Ent Pmf Evaluator
Run an honest, structured PMF self-check on the user's current data — Sean Ellis test, retention curves, organic acquisition %, the "tell" tests. Pushes back on wishful interpretation. Use when the user asks "do we have PMF?" or "how do we know if we're at PMF?" or when they're claiming PMF without strong evidence.
Ent Intake
Conversational placement and state capture. Interviews the founder to work out where they are on the 00→07 journey and writes the venture workspace for them, instead of asking them to hand-fill files. Use at cold start (no founder-state.yaml yet), when someone says "set me up", "where do I start", "onboard me", or to refresh state after time away.
Ent Synthesis Coach
Help the user synthesize a batch of interviews or research into clusters, patterns, and insights. Uses Pile Building, Cluster Analysis with active insight labels, stakeholder comparison, 2x2s, and hypothesis tracking. Use after every 5–10 interviews, when the user feels overwhelmed by their research, or when they say "help me synthesize" or "what patterns am I seeing?
Ent Interview Debrief
Capture, structure, and score a customer interview immediately after it happens — score desperation markers, distinguish facts from interpretation, surface surprises, and update the hypothesis tracker. Use within 30 minutes of completing a customer interview. Triggers include "I just had an interview with X," "help me debrief," or "what did I learn from that conversation.
Ent Thesis
Maintain the founder's cross-venture learnings ledger and synthesize it into a PMF-insights view, an investment/founder-style memo, or a sharpened value-hypothesis stance. Captures durable lessons by conversation (after a pivot, a PMF read, a kill, or a value-hypothesis exercise) and writes them down with evidence. Use when the user says "log a learning", "what's my investing style", "build my th…
Ent Pmf Memo
Synthesize the founder's whole journey into a 1-2 page PMF memo — insight, value hypothesis, desperation evidence, validation, metrics, the surprise, and an honest verdict. The capstone artifact you hand an investor, co-founder, or early hire. Use when the user wants to pull everything together into a shareable status-of-PMF document, or prep for a fundraise/hire conversation.
Ent Mvp Review
Run a two-week MVP product review during the build phase — what was built, what was learned from customers, what's next, and whether there's enough evidence to pivot/persevere/keep building. Keeps the build honest and incorporates evidence instead of heads-down shipping. Use at the end of each two-week sprint during MVP build (Stage 05).
Ent Problem Statement
Turn customer-discovery notes into a defensible, falsifiable problem statement (Stage 03). Forces specificity on the desperate customer, the single pain, the trigger, frequency, magnitude, alternatives, and behavioral evidence of desperation. Use when the user has finished a batch of discovery and needs to crystallize what they found before designing a solution.
Ent Red Team
Pressure-test a hypothesis, value proposition, pitch, strategy, or pivot decision by arguing the strongest case against it. Surfaces blind spots and consensus-thinking the user can't see. Use when the user is about to commit to a major decision, has fallen in love with a hypothesis, or asks for "honest feedback" or "tell me where I'm wrong.
Ent Customer Discovery
Track and steer a customer-discovery sprint across many interviews — surface recurring patterns, score desperation across the batch, and flag when the user is talking to needy vs. desperate customers or has stopped too early. Use when the user is in the middle of customer discovery (Stage 02), running multiple interviews, and wants to know what the data is telling them so far.
Ent Value Hypothesis Builder
Help the user write a PMF-grade value hypothesis — three components (what / who / how) plus a separate leap-of-faith statement. Pushes back on vague *whos*, compound *whats*, and confusing the value hypothesis with the leap of faith. Use when the user is in Stage 04, when they say "help me write my value prop / hypothesis," or when they've finished customer discovery and need to commit to a speci…
Ent Interview Prep
Prepare the user for a specific customer interview — building a focused script, surfacing the right questions for their current hypothesis, and enforcing Mom Test discipline. Use before any customer discovery / RDI conversation. Triggers include "I have a customer interview with X tomorrow," "help me prep for an interview," or specific mentions of an upcoming conversation.
Ent Mvp Scoper
Help the user decide what's in v1 of their MVP — given the value hypothesis and leap of faith, work out the smallest possible build that tests the leap of faith. Aggressively pushes back on overbuilding. Use when the user has a value hypothesis (Stage 04) and is about to build, when they ask "what should I build first," or when their MVP scope is exceeding 3 months.
Ent Career Coach
Coach a career decision for someone who wants to end up building or joining startups — which job to take, how to evaluate offers, whether to take a chief-of-staff role, when to leave. This is the OFF-SPINE career layer, separate from the 00→07 venture journey. Use when the question is "where should I work / which offer / should I take this role," NOT "how do I build my company." Full reference in…
Ent Concept Test
Design a cheap, fast concept test that proves whether a desperate customer would WANT a candidate solution — before building it. Picks the right format (landing page, video, concierge, follow-me-home, wizard-of-oz), defines the behavioral pass threshold, and keeps the user from drifting into an expensive build. Use when the user has a solution shape and needs to validate demand (Stage 03 / pre-St…
Ent Prompt Troubleshoot
Help the user fix AI prompts that aren't working — generic output, hallucinated facts, instruction-ignoring, output that's too long/short, no actionable conclusions. Use when the user complains about AI giving "slop," when they say "this prompt isn't working," or when they're frustrated with generic AI output.
Ent Rdi Coach
Coach the user through the Research Driven Inspiration (RDI) methodology — building a "prepared mind" in a new industry or space through team alignment, secondary research (industry primer), and 100+ stakeholder conversations. Use when the user is exploring a space and doesn't yet have a specific problem to solve, when they're considering a pivot to a new market, or when they explicitly mention R…
Ent Pivot Coach
Run a structured pivot-or-persevere decision. Diagnoses the failure mode in the user's data, identifies the over-performing slice if any, drafts the new value hypothesis if pivoting, and forces a written commitment with thresholds. Use when the user's PMF self-check is failing, when they say "should we pivot?", or when the data is telling them something isn't working.
Tell Them Something New
Cuts opening sentences that recap what the recipient already knows about themselves, their company, or their own work. Implements Konrad's rule 2 ("begin with something they don't know — tell me a secret about the future") and Kramon's rule 4. Use when a draft opens with flattery, a summary of the reader's accomplishments, restating their stated thesis, or reciting biographical facts they already…
Ent Cold Email
Write a winning cold email or outreach message — for RDI research, customer discovery, fundraising, hiring, or any cold outreach. Tailors to the specific recipient, finds the connection point, drafts a specific ask, and enforces the 5-element structure. Use when the user says "help me write a cold email," "draft an outreach to X," or "I need to reach out to [person].
Ent Unit Econ Check
Run a back-of-envelope unit-economics sanity check — LTV, CAC, LTV/CAC ratio, payback period — to catch a structurally broken business model before building. Not financial modeling; a directional check. Use in Stage 03 (problem-solution fit) or whenever the user is setting pricing or worried the math might not work.
Rhythm Killer
Fixes two sentence-rhythm tells that mark prose as AI-generated. Two targets behind one skill, picked via the --target arg. fragment-chain (three or more short sentences back-to-back) and uniform-length (two or more consecutive sentences within ~2 words of each other, especially with parallel structure). Use when the user says "reads like AI," "too choppy," "same length sentences back to back," "…
Connection Finder
Finds specific, genuine "like you" hooks between the writer and a cold-outreach target — the bridges that turn a generic email into one that feels hand-written. Takes the recipient dossier and the writer's profile (about-me.md) and surfaces ranked angles. Use after recipient-research is done, before drafting. Triggers on "like you," "find a connection," "what do we have in common," "common ground.
Fun Angle
Finds the unexpected, dry, or self-deprecating angle that makes an email memorable. Turns "professional and polite" into "this person sounds like a real human." Use when a draft is technically correct but forgettable, when the user wants humor without slapstick, or when they need a subject line or sign-off with personality. Triggers on "make it funny," "more personality," "less corporate," "humor…
Vividness
Pushes a draft from abstract toward concrete at two scales. Noun-level (replaces "dog" with "German shepherd," "customer" with "Sarah at JPMorgan's options-trading desk," "many" with "47 of 100") and scene-level (turns "I was angry" into the body signal, room, and dialogue). Implements Kramon's "specific over abstract" rule, Kristof's "real names, real numbers, real interviews," and Lauren Weinst…
Graveyard Historian
When pitching an idea, researches the graveyard — companies that tried something similar in the past 5–25 years and failed, what specifically killed them, and which operators or investors lived through those failures and would be valuable to talk to. Use before pitching to a VC, a customer, or a hiring manager — the graveyard reframes the pitch from "this is a great idea" to "this is a great idea…
Ent First Customers
Coach a founder to get their first ~10 paying customers — the tactics of early founder-led sales, not research interviews. Starts from where the buyer actually spends their day, works the warm-network → unscalable → tools ladder, and writes outreach with one clear ask. Use when the founder has something to sell and asks "how do I find / reach / close my first customers," "where do I get customers…
Ent Stage Router
Diagnose which entrepreneurship stage the user is in (from prepared mind / RDI through PMF measurement) and route them to the right framework, playbook, template, and skill for that stage. Use when the user asks for general help with their venture, says "where should I focus next," or describes their current situation without specifying what they need.
Pick A Lane
Diagnoses drafts that tell three half-stories instead of one full story, and rewrites them around the single strongest narrative thread. Implements Konrad's rule 7 and Adam Bryant's "stay in your lane" advice — distinct from compression (which cuts words) because pick-a-lane cuts whole stories. Use when a bio, cold email, op-ed, or pitch reads as a resume regurgitation, when the writer is dumping…
Ent Diligence
Run verification-first diligence on a set of factual claims — verify / flag / discard with sources, a what-must-be-true frame, and a gap list. Two directions; use when the founder is preparing their own memo or pitch for sharp scrutiny ("diligence my memo", "am I ready for investors"), or when they're evaluating someone else's claims (a company, a deal, a partnership) — the discipline that feeds…
Ent Office Hours
The front door. Take a half-formed product idea and interrogate it YC-office-hours style — listen to the pain not the feature request, reframe what the user is actually building, challenge premises, generate 2-3 implementation approaches with effort estimates, and recommend the narrowest wedge to test first. Use when someone shows up with "I want to build X" and needs it pressure-tested and refra…
Gratitude Note Coach
Helps draft cinematic, specific gratitude notes — Kramon's favorite assignment. Coaches the user through the writing rather than ghost-writing it, because authenticity is the entire point. Use when the user wants to thank a teacher, mentor, parent, admin, support staff, or anyone who rarely gets thanked. Triggers on "thank you note," "gratitude note," "thank-you letter," "appreciation note," "rec…