Charlie

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:

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:

1. Will this hire directly contribute to revenue?
2. What's the time-to-productivity? (Factor into ROI)
3. What else could this salary fund?
4. 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

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

Source: EveryInc/charlie-cfo-skill — distributed by TomeVault.