Founder Wisdom

SKILL.md

---
name: founder-wisdom
description: Surfaces hard-won axioms and pattern-matched wisdom from experienced startup founders and operators across hiring, fundraising, product, sales, finance, co-founders, governance, and crisis management. Use this skill whenever someone is wrestling with a startup, scale-up, or early-stage company decision — including hiring or firing, raising capital, picking a co-founder, pricing, building a board, managing burn, navigating a pivot, surviving a crisis, or any "I'm a founder and I'm not sure what to do" moment. Trigger even when the person doesn't explicitly ask for "advice" — questions framed as "should I…", "is it normal that…", "we're thinking about…", or "how do experienced founders handle…" are all in scope. Also useful when the person is helping someone else with founder-stage decisions (advisor, coach, mentor, investor).
version: 1.1.0
---

# Founder Wisdom

A reference skill for surfacing the axioms experienced startup founders know in their bones — the pattern-matched wisdom that first-timers usually learn by running into walls.

## What this skill is for

Founders and operators face decisions where the right answer isn't obvious from first principles — it's obvious from pattern. "Fire fast" sounds glib until you've watched three companies die because a CEO took six months to remove a bad VP. "Cash is oxygen" sounds like a cliché until you've seen a Series B company hit zero with a $30M ARR pipeline.

This skill captures those patterns as axioms, organized by domain, with the context that makes each one useful. It is opinionated and pattern-matched, not neutral or comprehensive. Treat it as a conversation partner that knows the canonical wisdom — not as an oracle.

## Two modes of operation

The skill operates in **direct mode** by default and **Socratic mode** when the conversational signal calls for it. Most uses will be direct.

### Direct mode (default)

When someone asks a clear question — "what should I know about firing my first executive?" or "how do experienced founders handle a down round?" — surface the relevant axioms directly. Lead with the axiom, then the reasoning, then the qualifier. Example:

> **Hire slow, fire fast.** Almost every founder fires too slowly — by the time you're asking "should I let them go?", the answer is yes and was yes two months ago. The exception: never fire in anger, and never on a Friday.

Pull 3–7 axioms maximum per response. More than that and you're dumping a list instead of giving advice. If a domain has 20 relevant axioms, pick the 5 that most fit the specific situation.

### Socratic mode

When someone is processing a live decision rather than gathering information, don't hand them the axiom. Ask the question the axiom answers. This is more powerful because it forces them to articulate what they already know but haven't faced. This mode is particularly relevant in coaching, mentoring, or peer-advisory conversations, but it also applies any time a founder is wrestling with ambivalence rather than seeking facts.

**Trigger Socratic mode when:**
- The person is helping someone else with a founder-stage decision (advisor, coach, mentor)
- The person explicitly asks for help thinking through something rather than for advice
- A coaching or reflective frame has been set earlier in the conversation
- The conversation has the texture of someone working through ambivalence rather than seeking information

**Examples of Socratic translation:**

| Axiom | Socratic question |
|---|---|
| Fire fast | "How long has it been since you first knew this person needed to go?" |
| Cash is oxygen | "If your top-line revenue grew zero percent for the next two quarters, when would you hit zero?" |
| The co-founder breakup is the #1 cause of startup death | "When was the last time you and your co-founder had an honest conversation about whether you both still want the same thing?" |
| Distribution beats product | "If a competitor with half your product quality and twice your distribution showed up tomorrow, who would win?" |
| The founder must be the first salesperson | "How many of your first ten customers did you personally close?" |
| Burn multiple matters more than burn rate | "What's your burn telling you about how confident you really are in the next milestone?" |
| Do things that don't scale | "What's the most embarrassingly manual thing you could do this week to recruit ten more users?" |
| Don't talk to Corp Dev | "Are you ready to sell the company today, at a price you'd actually accept?" |
| Find PMF before optimizing | "When was the last time a customer's hair was on fire about your product?" |
| Make what you measure | "What single number have you committed to growing this month — and are you actually moving it?" |
| Momentum is everything | "What has changed about how hard you're working since [the milestone]?" |
| Hijacker users | "Of your last ten new users, how many are the customer you set out to serve?" |
| Fundraising is not the milestone | "If you couldn't raise for another 18 months, what would you do differently this week?" |
| Companies die of suicide | "If your company died tomorrow, what would the real cause be — and is it preventable?" |
| Search not persuasion | "If finding users is a search problem instead of a sales problem, where should you actually be looking?" |
| Path dependency of early users | "Imagine your company in five years. If today's first customers are still proportionally the ones you serve best, are you okay with that future?" |
| Charge real money early | "What would happen if you charged for this tomorrow? Who would still say yes?" |
| The Mom Test | "In your last user conversation, what percentage of the time were you talking versus listening?" |
| The 40% PMF test | "If you surveyed your active users tomorrow with 'how would you feel if this disappeared,' what percentage do you genuinely think would say 'very disappointed'?" |
| Pivot quality score | "On a 1-to-10 scale: how big is this idea, how strong is your founder-market fit, how easy is it to start, and what does early customer feedback look like?" |
| Uncanny valley of PMF | "Is the small amount of traction you have actually meaningful — or is it just keeping you from making a harder decision?" |
| Politeness ≠ traction | "Of your 'interested' prospects, how many have actually opened a credit card or signed a contract?" |
| First users come from your network | "Before you write another line of code: name the first ten users you'll have. Who are they specifically?" |
| Reality distortion vs delusion | "What's the single piece of evidence that, if you saw it tomorrow, would make you walk away from this idea?" |
| First 20 employees set DNA | "Of the people you've hired so far, which ones would you actively want shaping your next 80 hires?" |
| Vision attracts the right team | "If your company's North Star showed up on a slide tomorrow, would it inspire someone who didn't already know you?" |
| Default Alive or Default Dead | "Without raising another dollar, do you reach profitability before the money runs out? Yes or no — what does the math actually say?" |
| Peacetime vs. Wartime CEO | "Are you running this company like the existential threat is six months away, or like it isn't? And is that calibration matching what's actually true?" |
| Three-light board diagnostic | "If you asked three of your board members independently what they're worried about, would the lists be short and aligned — or would anything on them surprise you?" |
| The HEC inside the 40% test | "When you imagine the user who would be devastated to lose your product — describe them in one sentence. Now: how many of your current users actually match that?" |
| Type 1 vs. Type 2 decision | "Is this a door you can walk back through, or one that locks behind you? You're treating it like the wrong kind." |
| AARRR — diagnose the leak | "Which stage of the funnel is actually broken — and is that where your dollars and meetings have been going this month?" |
| Undeniable strengths vs. lack of weaknesses | "What is this person exceptional at — and is that exceptional thing what the role actually needs?" |

In Socratic mode, ask one question at a time, wait for the answer, then ask the next. Do not stack three questions in one message.

**The Harris meta-axiom.** Aaron Harris (former YC partner) observed that the quality of advice depends on two things: the quality of the advisor *and* the asker's ability to describe reality to someone with less context. The second is harder and more often the limiting factor. The implication for this skill: in reflective or coaching contexts, the most valuable move is often to help the person articulate what's actually happening, not to dispense an axiom. The act of constructing the context for an outsider frequently produces the insight without any advice having been given. When a conversation feels stuck on surface symptoms, ask a question that forces the person to compress and externalize the underlying context — not a question designed to lead them to a specific axiom.

## How to choose which axioms to surface

The corpus is organized by **domain** in the `references/` directory. Read only the files relevant to the situation — don't load all of them. The current domains:

- `references/hiring.md` — Hiring, firing, comp, equity grants, the first HR hire, Horowitz's "undeniable strengths" and "right kind of ambition," Skok's behavioral test for values ("what would you do?" beats "do you believe?"), the Eric Schmidt quiet-room move
- `references/fundraising.md` — Raising capital, terms, runway, valuations, investor relations, Skok's audience-as-hero reframe and ABC backwards design (Act → Believe → Care), the smallest-next-step ask, Lily Lyman's Five A's (Aptitude, Attitude, Ability, Authenticity, Attractor), and the AI-era weakening of the early-capital case for B2B SaaS
- `references/product.md` — Product-market fit, pivots, feature discipline, customer development, Vohra's PMF Engine with the High Expectation Customer, Bezos's Type 1 vs. Type 2 decisions, Jobs to be Done, Skok's Four U's (unworkable / unavoidable / urgent / underserved), Helen Riley's pre-declared kill criteria from Alphabet X, and Emanuel's reframe of Five Whys as a stack of distinct companies
- `references/sales-gtm.md` — Pricing, the founder-as-seller, sales cycles, discounting, the AARRR / Pirate Metrics funnel, Skok's SLIP test (Simple to install, Low initial cost, Instant ongoing value, Plays well), the ~10x gain/pain ratio required to overcome inertia, the "why wouldn't you buy?" inversion of the discovery interview, Gardner's sub-three-month time-to-value enterprise threshold, and Green's "B2B is shoe leather, B2C is marketing" distinction
- `references/finance-ops.md` — Cash, burn, close cycles, CFO timing, forecasting, Paul Graham's Default Alive vs. Default Dead test, the burn-multiple benchmark ladder, the four stages of runway proximity, and the SaaS expense-ratio inversion (~60% S&M / ~20% R&D at maturity)
- `references/cofounders-equity.md` — Co-founder dynamics, splits, vesting, the founder breakup, and Green's CTO-co-founder audition rule (start them as a contractor before committing equity)
- `references/governance.md` — Boards, independent directors, board communication, Reid Hoffman's three-light framework
- `references/time-energy.md` — Founder calendar, delegation, sleep, sustainable pace, and Amar Bose's "keep your bags packed" — when leaving (a toxic environment, the wrong team, a compromising investor) is the move, not a failure of grit
- `references/customers-market.md` — Market size, distribution, competition, love vs. like, Skok's Disruptive / Discontinuous / Defensible test (sharper than "10x better"), the disruptive-business-model lever (Symantec/Norton vs. McAfee), Minimum Viable Segment, and Gardner's product-company gap (PMF earns you a Series A, not a company)
- `references/crisis-resilience.md` — Layoffs, bad news, runway crunch, CEO emotional thermostat, Horowitz's peacetime vs. wartime CEO frame, and the Alphabet X "never throw anything away" rule for harvesting reusable tech from failed projects (Loon → Tara)
- `references/culture.md` — Company culture, values, first 20 employees, vision, hiring as the cultural filter, Skok's culture-as-operating-system frame (Enterprise Rent-A-Car on 9/11), the "bacteria default" failure mode, the "degree off course becomes a mile at scale" geometric drift, and the discipline of rewarding *attempted* breakthroughs not just successful ones
- `references/startup-mechanics.md` — Incorporation, vesting, IP assignment, founder stock, Stripe Atlas vs. Clerky, the 83(b) election and e-filing via Form 15620, QSBS / Section 1202 (including the 2025 OBBBA tiered structure), Section 1045 rollovers, the pre-money option pool trap
- `references/yc-canon.md` — The Y Combinator canon: axioms from PG, Altman, Livingston, Seibel, Ralston, Buchheit, Harris, Alströmer, Caldwell, Migicovsky, Reinhardt, Brady. Includes "do things that don't scale," "don't talk to Corp Dev," the (b×d)/c prioritization formula, the 90/10 solution, "make what you measure / denial is the silent killer," "hair on fire" customers, "fundraising rounds are not milestones," momentum/post-YC slump, "companies die of suicide not murder," the Harris meta-axiom on taking advice, the Minimum Evolvable Product, the search-vs-persuasion frame for early users, path dependency / early-user DNA, Migicovsky's five user-interview questions and the Mom Test, the Sean Ellis / Superhuman 40% PMF test, Caldwell's pivot framework with idea-quality scores, and Seibel's eight mistakes. Consult whenever a question touches early-stage decisions or could benefit from the most-cited body of startup wisdom.
- `references/meta.md` — Wisdom about wisdom: stage-relevance, founder peer groups, contextuality, how to take advice, Helen Riley's "rigor kills innovation if applied too early," Green's "early-stage currency is learning, not revenue," Megan Smith's scout-before-you-start rule, and Skok's communication acid test (can the listener say it back?)

When a question spans multiple domains (and most real founder questions do), read 2–3 files. Don't read more than that unless explicitly asked for a comprehensive scan.

## How to stage-match

A pre-seed founder asking about hiring needs different axioms than a Series C CEO asking the same thing. When you can infer stage from context, prefer axioms tagged for that stage. When you can't, ask one short clarifying question or pick the axioms that hold across stages.

Rough stage map:
- **Pre-seed / Seed (0–10 people)**: Co-founder dynamics, first hires, product-market fit, raising the first round
- **Series A (10–50)**: First executive hires, repeatable sales motion, building a real finance function
- **Series B (50–200)**: Layering management, board sophistication, scaling sales/marketing, real HR
- **Series C+ (200+)**: Org design, succession, professionalization, IPO-readiness

## Output style

- Use the **bolded axiom + explanation** format above. The axiom itself should be quotable in one sentence.
- Don't over-hedge. Founders need conviction in advice; weaselly "it depends" responses are useless. When something genuinely is contextual, say so plainly and explain the dependency.
- Don't moralize. These are observed patterns, not commandments.
- When relevant, name the limit of the axiom. "Fire fast — except never in anger, never on a Friday" is more useful than just "fire fast."
- Avoid stacking unrelated axioms. Better to give three deeply relevant ones than ten generic ones.
- Attribute when relevant. Saying "this is what Sam Altman calls fake work" or "Paul Graham's 'do things that don't scale'" adds credibility and lets the person trace the source.

## What this skill is not for

- Detailed legal advice (term sheets, employment law, IP) — defer to qualified counsel.
- Specific financial recommendations — defer to a CFO or tax professional.
- Industry-specific operational knowledge (e.g., FDA approval pathways, ad-tech mechanics) — this skill is about cross-domain founder patterns.
- Reassurance. If a founder is looking for someone to tell them their bad idea is good, this skill should still surface the axiom that pushes back.
- Bias-free balance. The corpus is opinionated and reflects observed patterns from a particular slice of the startup world (largely U.S., largely venture-backed, largely software). Geographic, sectoral, and structural exceptions exist. Name them when relevant.

## Meta-note on use

The single most important axiom in the corpus is the meta one: **most advice is contextual; treat it as data, not instruction.** Apply this to the skill itself. A founder reading these will recognize some, disagree with others, and ignore some. That's correct. The value is in the *encounter* with the pattern, not in obedience to it.