charlie
Your AI CFO for bootstrapped startups, named after Charlie Munger who embodied the principle that capital discipline is a competitive advantage. Provides financial frameworks for cash management, runway calculations, unit economics (LTV:CAC), capital allocation, hiring ROI, burn rate analysis, working capital optimization, and forecasting. Use for questions like "should we make this hire?", "how much runway do we need?", "what metrics should I track?", "how do I forecast revenue?", or any strategic financial decision at a self-funded company.
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Install
Works with every agent the skills CLI supports.
npx skills add https://github.com/everyinc/charlie-cfo-skill --skill charlie- 01
Install
Run the command in your project. The CLI asks which agents to install for.
- 02
Describe the task
Ask your agent for something this skill covers. It loads charlie automatically when relevant.
- 03
Review the result
The agent follows the SKILL.md steps, scripts and references bundled with the skill.
SKILL.md
The instructions your agent reads when the skill is triggered.
Charlie CFO: Bootstrapped Financial Management
Your AI CFO for bootstrapped, profitable companies. Named after Charlie Munger, who embodied the principle that capital discipline is a competitive advantage.
Core Mental Models
Profit is a constraint, not a goal. Bootstrapped companies succeed because capital constraints force better decisions. Every dollar has three costs: direct expenditure, opportunity cost, and runway impact.
Unit economics are survival requirements:
- LTV ≥ 3x CAC (best-in-class: 7-8x)
- CAC payback < 12 months (high performers: 5-7 months)
- Violating these creates a death spiral bootstrapped companies cannot survive
Revenue per employee is your efficiency scorecard:
- $110-150K at $1-5M ARR
- $200-250K at $10-50M ARR
- $400K+ at maturity
- Bootstrapped companies run 40-70% higher than VC-backed peers
Cash Management Rules
Runway targets:
- Minimum: 24-36 months
- Danger zone: <12 months (you've lost control)
- Never fundraise your way out of a cash crisis
Reserve structure:
| Reserve | Amount | Purpose |
|---|---|---|
| Operating | 3-6 months fixed costs | Payroll, rent, essential software |
| Contingency | 1-2 months expenses | Emergencies |
| Growth | Excess | Opportunistic investments |
Burn multiple = Net Burn ÷ Net New ARR
- <1x: Excellent
- 1-1.5x: Good
-
2x: Concerning
- Bootstrapped target: Zero or negative (profitable growth)
Capital Allocation Framework
Every investment question: What is the payback period? Target <12 months.
Rule of 40: Revenue Growth % + EBITDA Margin % ≥ 40%
- High growth path: 40% + 0%
- Balanced path: 20% + 20%
- Profit path: 10% + 30%
Hiring decisions:
- Will this hire directly contribute to revenue?
- What's the time-to-productivity? (Factor into ROI)
- What else could this salary fund?
- Does this make existing team more productive?
Never grow a department >50% at once — productivity drops to zero during training.
Working Capital Optimization
Cash Conversion Cycle (CCC): DIO + DSO - DPO
- SaaS target: Negative (-30 to -90 days)
- Every 10-day reduction frees significant working capital
AR discipline: Target 30-45 days DSO
- Reminder 7 days before due
- Follow up Day 1, 7, 14, 30 past due
AP strategy: Pay on due date, not early, unless discount > cost of capital
- 2% discount for 20 days early = 36.5% annualized return
- Negotiate Net 45-60 terms after proving reliability
Annual prepay: Offer 15-20% discount
- Produces 30% lower churn
- 27-40% higher LTV
- Customers finance your growth at 0% interest
Financial Review Rhythms
Weekly (60-90 min):
- Cash position
- AR aging
- Pipeline movement
- Revenue/bookings
Monthly:
- Full close (target 5-7 business days)
- Variance analysis
- 12-18 month rolling forecast update
Quarterly:
- Strategic recalibration
- Scenario refresh (base/moderate/severe)
- 18-24 month outlook
Key Metrics Dashboard
| Category | Metrics | Targets |
|---|---|---|
| Revenue | MRR/ARR, growth rate, NRR | NRR >100%, growth 15-25% YoY |
| Unit economics | LTV:CAC, CAC payback, gross margin | 3:1+, <12 mo, 70-80% |
| Cash | Burn rate, runway, operating cash flow | Runway 24-36 months |
| Customer health | Churn, concentration | Monthly churn <2%, no customer >10% revenue |
Customer concentration warning: Any customer >10% revenue OR top 5 >25% revenue
Forecasting Approach
Use driver-based planning — models built on operational drivers (headcount, acquisition rate, churn), not static percentages.
MRR buildup model:
Starting MRR + New Bookings + Expansion - Churn = Ending MRR
13-week cash flow forecast:
- Update every Monday
- Compare actuals to forecast weekly
- Cross-functional validation (sales confirms timing, ops verifies schedules)
Always maintain three scenarios:
- Base case: Expected trajectory
- Moderate downside: -15-20% revenue
- Severe downside: -30-40% revenue
For each: Calculate runway, define action thresholds (hiring freeze, cost cuts).
Spending Benchmarks ($3-5M ARR)
- Sales: 10-15% of ARR
- Marketing: 8-10% of ARR
- R&D: 25-30% of ARR
- Customer Success: 8-12% of ARR
- G&A: ~14% of ARR
- Total: ~95% (vs. 107% for VC-backed)
References
- See references/metrics-benchmarks.md for detailed metric calculations and industry benchmarks
- See references/case-studies.md for examples from Mailchimp, Zapier, Basecamp, ConvertKit, and Zoho
FAQ
What does the charlie skill do?
Your AI CFO for bootstrapped startups, named after Charlie Munger who embodied the principle that capital discipline is a competitive advantage. Provides financial frameworks for cash management, runway calculations, unit economics (LTV:CAC), capital allocation, hiring ROI, burn rate analysis, working capital optimization, and forecasting. Use for questions like "should we make this hire?", "how much runway do we need?", "what metrics should I track?", "how do I forecast revenue?", or any strategic financial decision at a self-funded company.
How do I install charlie?
Run npx skills add https://github.com/everyinc/charlie-cfo-skill --skill charlie in your project. The skills CLI detects the agents you use and copies the skill into the right folder. For Claude Code you can also place the skill folder at ~/.claude/skills/charlie/ (personal) or .claude/skills/charlie/ (project).
Which AI agents can use charlie?
Any agent that supports the open Agent Skills format (a folder with a SKILL.md file), including Claude Code, Codex, Cursor, GitHub Copilot, Gemini CLI, Windsurf, Cline, OpenCode and more.
Is charlie safe to install?
No partner security audit is available yet. Skills can run commands and scripts, so read the SKILL.md and any bundled files before installing.
Who maintains charlie?
It is published by everyinc in everyinc/charlie-cfo-skill. It has 565 recorded installs.
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