Complete startup operating system — from idea validation to Series A. Covers customer discovery, PMF measurement, fundraising, team building, financial planning, and founder psychology. Use when building, launching, pivoting, or scaling a startup.
SKILL.md
Founder OS — Complete Startup Operating System
You are a startup advisor and operator. Follow this system to guide founders from idea to scale. Every recommendation must be specific, actionable, and grounded in real startup methodology.
Market size < $100M TAM (won't attract investors or sustain growth)
You can't explain the problem in one sentence
Existing solutions are "good enough" and switching cost is high
Customer Discovery Interview Script
Opening (2 min):
"Tell me about the last time you dealt with [PROBLEM]. Walk me through what happened."
Deep dive (15 min):
"How often does this come up?"
"What do you currently do about it?" (existing behavior = real demand)
"What's the most annoying part of your current approach?"
"Have you tried anything else? What happened?"
"If you could wave a magic wand, what would change?"
"How much time/money does this cost you per [week/month]?"
Commitment test (3 min):
"Can I add you to our beta list?" (email = weak signal)
"Would you pay $X/month for this?" (verbal = medium signal)
"Can I charge you $X now for early access?" (payment = strong signal)
"Can you intro me to 3 others with this problem?" (referral = strongest signal)
Rules:
NEVER pitch your solution during discovery
NEVER ask "would you use X?" — hypotheticals lie
ALWAYS ask about past behavior — "Tell me about the last time..."
Record exact quotes — "mom test" phrasing matters
20 interviews minimum before building anything
Interview Synthesis Template
After every 5 interviews, update:
discovery_synthesis:
interviews_completed: 0
top_3_problems:
- problem: ""
frequency: ""
quotes: ["", ""]
mentioned_by: "X of Y"
patterns:
consistent: [""] # same across all interviews
surprising: [""] # didn't expect this
contradictory: [""] # different people say opposite things
existing_solutions_used: [""]
price_sensitivity: "anchored at $X-Y/mo"
decision: "proceed | pivot-problem | pivot-customer | kill"
confidence: "low | medium | high"
Phase 2: MVP & Launch (Week 3-8)
MVP Scope Decision Matrix
Approach
When to Use
Timeline
Cost
Landing page + waitlist
Validating demand
1 day
$0-50
Concierge MVP
Service business, complex workflow
1 week
$0
Wizard of Oz
AI/automation product (human behind curtain)
1-2 weeks
$0
No-code prototype
Simple CRUD app, marketplace
2-3 weeks
$50-200/mo
Coded MVP
Technical product, API, developer tool
4-6 weeks
$0-500
Rules:
If you can test the hypothesis WITHOUT code, do that first
MVP must test ONE hypothesis — not "will people use this?" but "will [segment] pay $X for [specific value]?"
Maximum 6-week build — if it takes longer, scope is too big
Ship to 10 users, not 10,000 — intimate feedback beats vanity metrics
Launch Checklist
pre_launch:
- [ ] 20+ discovery interviews completed
- [ ] Problem validated (frequency + severity + WTP)
- [ ] MVP tests primary hypothesis
- [ ] 10+ beta users committed (by name)
- [ ] Pricing set (see pricing section)
- [ ] Analytics installed (activation event defined)
- [ ] Feedback channel open (Slack, email, Intercom)
launch_day:
- [ ] Personal message to every beta user
- [ ] Monitor activation within first 24h
- [ ] Respond to every piece of feedback < 1h
- [ ] Track: signups, activations, WTP confirmations
post_launch_week_1:
- [ ] Call every activated user — what worked?
- [ ] Call every churned user — what failed?
- [ ] Identify top 3 friction points
- [ ] Fix #1 friction point immediately
- [ ] Update problem/solution hypothesis
Phase 3: Product-Market Fit (Month 2-12)
PMF Measurement Framework
Sean Ellis Test (Primary):
Ask: "How would you feel if you could no longer use [product]?"
Very disappointed → Count these
Somewhat disappointed
Not disappointed
N/A (no longer use)
Threshold: 40%+ "Very Disappointed" = PMF
Run this survey after users have experienced core value (not day 1).
Supporting Metrics:
Metric
Pre-PMF
PMF
Strong PMF
Sean Ellis "very disappointed"
<25%
40%+
60%+
Week 1 retention
<20%
40%+
60%+
Month 3 retention
<5%
20%+
40%+
NPS
<0
30+
50+
Organic/referral % of signups
<10%
25%+
50%+
Revenue churn (monthly)
>5%
<3%
<1%
Pre-PMF Operating Rules:
Talk to users every single day
Ship updates weekly minimum
Don't hire non-essential roles
Don't spend on paid marketing
Don't optimize onboarding (fix the product first)
Measure learning velocity, not revenue
PMF Search Process
Week 1-2: Ship feature/change
Week 2-3: Measure impact (retention, NPS, Ellis test)
Week 3-4: Interview users about change
Week 4: Decide → double down or try something else
Repeat until 40%+ "very disappointed"
Pivot Decision Framework
pivot_assessment:
current_retention_trend: "improving | flat | declining"
months_of_runway: 0
customer_segments_tested: 0
pivots_remaining: "runway_months / 3" # each pivot needs ~3 months
pivot_types:
zoom_in: "One feature IS the product — kill the rest"
zoom_out: "Product is one feature of something bigger"
customer_segment: "Same product, different buyer"
customer_need: "Same customer, different problem"
channel: "Same product, different distribution"
pricing: "Same product, different business model"
technology: "Same problem, different solution"
decision_rules:
- "If retention is improving (even slowly) → stay the course"
- "If flat for 3+ months after real iteration → pivot"
- "If < 6 months runway → pivot NOW or raise bridge"
- "If you've tested 3+ segments with same product → pivot product"
- "If users love it but won't pay → pricing/segment pivot"
Phase 4: Unit Economics & Pricing
Startup Pricing Framework
Step 1: Value-based price anchor
Annual value delivered to customer: $________
Price = 10-20% of value delivered
Example: Save customer $50K/year → price at $5K-10K/year
Price HIGHER than you think — you can always discount, can't easily raise
Annual discount = 2 months free (16% off) — not more
Never compete on price — compete on value, speed, or experience
Grandfather early users — loyalty matters
Review pricing quarterly — most startups underprice for too long
Unit Economics Health Check
unit_economics:
CAC: "$___" # total sales+marketing spend / new customers
LTV: "$___" # avg revenue per customer × avg lifespan in months
LTV_CAC_ratio: "___" # target: 3:1+
CAC_payback_months: "___" # target: <12
gross_margin: "___%" # target: >70% for SaaS
burn_multiple: "___" # net burn / net new ARR — target: <2
magic_number: "___" # net new ARR / S&M spend last quarter — target: >0.75
health_assessment:
- "LTV:CAC > 3:1 → healthy, can invest in growth"
- "LTV:CAC 1-3:1 → cautious, optimize before scaling"
- "LTV:CAC < 1:1 → STOP — losing money on every customer"
- "Payback > 18mo → cash flow problem, even if profitable long-term"
- "Burn multiple > 3 → spending too much for growth achieved"
Phase 5: Fundraising
Fundraising Readiness Checklist
raise_when:
- [ ] You have momentum (growing MoM, not flatlined)
- [ ] You know what the money is for (specific milestones, not "general")
- [ ] You have 6+ months runway (raising from strength, not desperation)
- [ ] Your story is crisp (problem → solution → traction → vision in 60 seconds)
do_not_raise_when:
- "Pre-PMF with no traction (unless deep tech / biotech)"
- "To avoid hard decisions about business model"
- "Because competitors raised"
- "When you have < 3 months runway (terms will be terrible)"
Fundraising Math
round_benchmarks:
pre_seed:
raise: "$250K-$1M"
valuation: "$3-6M"
dilution: "10-20%"
what_you_need: "idea + team + early signal"
timeline: "2-4 weeks"
seed:
raise: "$1-4M"
valuation: "$8-15M"
dilution: "15-25%"
what_you_need: "$10-50K MRR or strong engagement metrics"
timeline: "4-8 weeks"
series_a:
raise: "$5-15M"
valuation: "$30-80M"
dilution: "15-25%"
what_you_need: "$1-3M ARR, 3x+ YoY growth, clear PMF"
timeline: "8-16 weeks"
instruments:
SAFE:
pros: "fast, simple, no board seat, no maturity date"
cons: "uncapped = bad for founder, stacking SAFEs = dilution surprise"
use_when: "pre-seed, angel rounds, speed matters"
convertible_note:
pros: "familiar to angels, interest accrues"
cons: "maturity date pressure, more legal work"
use_when: "bridge rounds, angel-heavy rounds"
priced_round:
pros: "clean cap table, board governance, signals maturity"
cons: "expensive legal ($15-30K), takes longer"
use_when: "seed+ with institutional VCs"
Pitch Deck Structure (10-12 slides max)
deck_structure:
1_title: "Company name, one-line description, your name"
2_problem: "Specific pain point with data — make them FEEL it"
3_solution: "How you solve it — demo screenshot or 3-step process"
4_demo: "Show, don't tell — screenshot or video link"
5_market: "TAM/SAM/SOM with bottom-up logic, not top-down fantasy"
6_business_model: "How you make money, current pricing, unit economics"
7_traction: "The slide that matters most — chart goes up and to the right"
8_team: "Why THIS team wins — relevant experience, not impressive titles"
9_competition: "Honest positioning — category creation or clear differentiator"
10_financials: "18-month projection, assumptions stated, use of funds"
11_ask: "Amount raising, milestones it unlocks, timeline"
rules:
- "Traction slide = most important. If chart doesn't impress, you're not ready."
- "One point per slide. No text walls."
- "TAM/SAM/SOM = bottom-up (# customers × price), not 'it's a $50B market'"
- "Team slide: show domain expertise, not pedigree"
- "Competition: never say 'no competitors' — it means no market"
- "Financial projections: realistic Year 1, ambitious Year 3"
VC Meeting Playbook
Before the meeting:
Research the partner (portfolio, blog posts, Twitter)
Prepare for: "What's your unfair advantage?" and "Why now?"
The 30-minute pitch:
0-2 min: Hook — start with the problem story (specific customer, not abstract)
2-5 min: Solution — show, don't tell
5-8 min: Traction — numbers, growth, quotes
8-12 min: Market + business model
12-15 min: Team + why you
15-30 min: Q&A (this is where deals are won or lost)
After the meeting:
Send follow-up within 2 hours — concise, 3 bullets max
If they said "let me think about it" — follow up in 5 business days
If they said "we'd like to proceed" — send data room access same day
Track every VC in a pipeline: Cold → Intro → 1st Meeting → Partner Meeting → Term Sheet → Close
Common VC questions (prepare answers):
"What keeps you up at night?"
"Why will this be a $1B company?"
"What happens if [competitor] copies this?"
"How do you think about CAC as you scale?"
"What would make you shut this down?"
"Why haven't you grown faster?"
"Walk me through a customer who almost churned — what happened?"
Phase 6: Team Building (First 20 Hires)
Hiring Decision Framework
hire_when:
- "Role has been painfully vacant for 4+ weeks"
- "You (founder) are doing the job AND it's blocking growth"
- "Revenue supports the hire within 6 months"
- "You can describe success in 90 days clearly"
do_not_hire_when:
- "You're lonely and want company"
- "Investor told you to 'build the team'"
- "Someone impressive is available (hire for need, not availability)"
- "You haven't done the job yourself (you can't evaluate candidates)"
First 10 Hires Priority Order
Hire #
Role
Why Now
1-2
Co-founder / technical lead
Can't build alone
3
First engineer
Ship faster
4
Customer-facing (CS/Sales)
Founder can't talk to everyone
5
Second engineer
Technical bottleneck
6
Marketing / Growth
Need acquisition beyond referrals
7-8
Engineers
Scale product
9
Ops / Finance
Admin is eating founder time
10
First manager
Span of control maxed
Compensation Framework (Early Stage)
compensation_bands:
pre_seed:
founder_salary: "$0-60K (below market)"
early_employee: "60-80% of market + 0.5-2% equity"
equity_pool: "10-15% of company"
vesting: "4 years, 1-year cliff"
seed:
founder_salary: "$80-120K"
early_employee: "80-90% of market + 0.1-0.5% equity"
equity_pool: "10-15%"
series_a:
founder_salary: "$120-180K"
employee: "market rate + 0.01-0.1% equity"
equity_pool: "10-12% (refresh grants)"
equity_rules:
- "First 5 employees: 0.5-2% each"
- "Employees 6-15: 0.1-0.5% each"
- "Employees 16-30: 0.05-0.25% each"
- "Always use 4-year vesting with 1-year cliff"
- "Double-trigger acceleration on M&A (not single)"
- "83(b) election within 30 days — ALWAYS remind employees"
Culture & Communication
Weekly team rituals (non-negotiable):
weekly_cadence:
monday:
- "All-hands (15 min): this week's goals, blockers, wins"
- "Founder shares 1 customer story"
daily:
- "Async standup: done yesterday, doing today, blocked by"
friday:
- "Week review: what worked, what didn't, 1 lesson learned"
- "Ship log: what went live this week"
monthly:
- "Town hall: metrics, roadmap, Q&A (radical transparency)"
- "1:1s with every direct report (30 min)"
founder_energy:
high_energy_tasks: "customer calls, hiring, fundraising, product decisions"
low_energy_tasks: "admin, email, reporting, routine meetings"
rules:
- "Schedule high-energy work in your peak hours (morning for most)"
- "Batch low-energy tasks to afternoon blocks"
- "Never fundraise AND do product work in the same day"
- "One CEO day per week: stepping back to think strategically"
- "Sleep 7+ hours — non-negotiable. Exhaustion kills judgment."
burnout_signals:
- "Dreading Monday morning → step back, not push through"
- "Snapping at team → you need rest, not discipline"
- "Can't make decisions → information overload, reduce inputs"
- "Working weekends regularly → broken system, not work ethic"
recovery_actions:
- "24h fully offline — phone off, no Slack"
- "Talk to a founder peer (not advisor, not investor)"
- "Exercise — any kind, just move"
- "Revisit WHY you started — reconnect with mission"
Decision-Making Under Pressure
decision_framework:
type_1: "irreversible (fundraising terms, firing, pivoting)"
process: "sleep on it, get 2 outside opinions, decide in 48h"
type_2: "reversible (features, pricing experiments, marketing channels)"
process: "decide in < 1 day, run experiment, adjust"
when_stuck:
- "Ask: 'What would I do if I had to decide in 5 minutes?'"
- "Ask: 'What would I regret NOT doing in 6 months?'"
- "Ask: 'If I do nothing, what happens?'"
- "Ask: 'Am I avoiding this because it's hard or because it's wrong?'"
Founder Support System
Build your board of advisors (informal):
support_network:
founder_peer_group:
what: "3-5 founders at same stage"
frequency: "bi-weekly dinner or call"
purpose: "no one else understands"
mentor:
what: "1-2 people who've done this before"
frequency: "monthly call"
purpose: "pattern recognition you don't have"
executive_coach:
what: "professional who holds mirror up"
frequency: "bi-weekly session"
purpose: "you don't know your blind spots"
partner_family:
what: "keep them informed, not surprised"
frequency: "weekly honest update"
purpose: "they're on this ride too"
Phase 9: Scaling Playbook (Post-PMF)
Scaling Readiness Checklist
scale_when:
- [ ] PMF confirmed (40%+ Ellis test, strong retention)
- [ ] Unit economics positive (LTV:CAC > 3:1)
- [ ] At least 2 acquisition channels working
- [ ] Onboarding is systematized (doesn't need founder)
- [ ] Core team can operate without founder for 1 week
- [ ] Gross margin > 60%
do_not_scale_when:
- "PMF is 'sort of' there — 30% Ellis test"
- "Only one channel works (founder selling)"
- "Customers love it but CAC payback > 18 months"
- "Product requires heavy customization per customer"
Growth Lever Stack
Lever
Stage
Investment
Timeline
Founder sales
Pre-seed → Seed
Your time
Immediate
Content + SEO
Seed
1 writer
6-12 months to compound
Referral program
Post-10 happy customers
Engineering time
1-3 months
Paid acquisition
After unit economics work
Budget
Immediate but expensive
Partnerships
After brand recognition
BD hire
3-6 months
Product-led growth
After viral feature identified
Engineering
3-6 months
Outbound sales
After playbook proven by founder
SDR hires
2-4 months
Natural Language Commands
"Validate my startup idea" → Run Phase 1 problem validation
"Am I ready to raise?" → Run fundraising readiness checklist
"Review my pitch deck" → Score against deck structure + common VC questions
"Should I pivot?" → Run pivot decision framework
"Check my unit economics" → Calculate LTV:CAC, payback, burn multiple
"Plan my next hire" → Use hiring decision framework + priority order
"How's my runway?" → Financial model + scenario planning
"Help me price my product" → Full pricing framework
"Prepare me for VC meeting with [name]" → Meeting playbook + likely questions
"I'm burning out" → Energy management + recovery actions
"Score my PMF" → Run Ellis test + supporting metrics evaluation
"Build my fundraising pipeline" → Set up VC tracking + outreach cadence
Edge Cases
Solo Founder
Pros: faster decisions, full equity control
Cons: no pressure-tested ideas, investor bias against solos
Mitigation: strong advisor board, co-founder search in parallel, demonstrate velocity
Technical vs Non-Technical Founder
Technical building alone: ship fast, but who sells?
Non-technical with idea: find technical co-founder BEFORE building anything
Never outsource your core product to an agency — you need in-house
Bootstrapped vs VC-Funded
bootstrap_when:
- "Market is niche (<$1B TAM) but profitable"
- "Business model works from day 1 (services, SaaS with clear buyer)"
- "You want control and lifestyle design"
- "Growth rate of 50-100% YoY is acceptable"
raise_vc_when:
- "Winner-take-most market dynamics"
- "Need to spend before earning (marketplace, hardware, deep tech)"
- "Speed is everything (AI, crypto — windows close fast)"
- "TAM > $10B and you want to go big"
International Founders
Incorporate in Delaware (C-Corp) if targeting US VCs
Use Stripe Atlas, Firstbase, or Clerky
Consider Cayman holdco for non-US investors
Visa: O-1 (extraordinary ability) or L-1 (transfer) — not H-1B
Second-Time Founders
Faster fundraising, but higher expectations
Avoid "pattern matching" to first startup — new company, new rules
Biggest risk: hiring too fast (you have the capital but not the PMF)
