entrepreneurship-lessons

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," or is defaulting to cold email for a buyer who doesn't live in their inbox.

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 the investment-style memo in the thesis ledger.

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.

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 thesis", "what have I learned", or after a major decision in any venture.

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 career/career_strategy.md.

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]."

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-Stage 05).

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.

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.

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.

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.

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.

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).

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.

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 reframed before committing.

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.

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.

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.

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.

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 RDI or "prepared mind."

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.

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?"

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.

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 specific bet.

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."

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."