Generate investor updates, board decks, portfolio financial reports, cap table scenarios, runway modeling, and fundraising pipeline tracking
npx claudepluginhub cure-consulting-group/productengineeringskillsThis skill uses the workspace's default tool permissions.
Before starting, gather project context silently:
Generates design tokens/docs from CSS/Tailwind/styled-components codebases, audits visual consistency across 10 dimensions, detects AI slop in UI.
Records polished WebM UI demo videos of web apps using Playwright with cursor overlay, natural pacing, and three-phase scripting. Activates for demo, walkthrough, screen recording, or tutorial requests.
Delivers idiomatic Kotlin patterns for null safety, immutability, sealed classes, coroutines, Flows, extensions, DSL builders, and Gradle DSL. Use when writing, reviewing, refactoring, or designing Kotlin code.
Before starting, gather project context silently:
PORTFOLIO.md if it exists in the project root or parent directories for product/team contextcat package.json 2>/dev/null || cat build.gradle.kts 2>/dev/null || cat Podfile 2>/dev/null to detect stackgit log --oneline -5 2>/dev/null for recent changesls src/ app/ lib/ functions/ 2>/dev/null to understand project structureInvestor communications for a multi-product venture studio. Monthly updates, board decks, portfolio financials, cap table modeling, runway scenarios, and data room preparation. Optimized for Cure Consulting Group's portfolio: Vendly, Autograph, The Initiated, Antigravity, and TwntyHoops.
Investors remember two things: how honest you were when things were hard, and whether you delivered on what you said you would. This skill ensures both.
| Need | Output | Audience |
|---|---|---|
| Monthly investor update | 1-page email with metrics, wins, losses, asks | Angels, pre-seed/seed investors |
| Quarterly board deck | 12-15 slide deck with portfolio health + decisions | Board members, lead investors |
| Portfolio financial report | Consolidated P&L, burn, runway, unit economics | CFO, board, institutional investors |
| Fundraising data room | Organized document checklist for due diligence | Prospective investors, VCs |
| Cap table modeling | Pre/post money, dilution, waterfall, SAFE conversion | Founders, legal, prospective investors |
| Runway & scenario modeling | Burn analysis, revenue scenarios, decision framework | Internal leadership, board |
| Ad-hoc investor request | Custom data pull or narrative for a specific investor | Individual investor or fund |
Before generating any investor artifact, collect:
The single most important investor communication. Send it on the same day every month, no exceptions. Even — especially — when things are bad.
Delivery: Plain-text email (not a PDF, not a deck, not a Notion link)
Length: Under 1 page, 5-minute read maximum
Frequency: Monthly, same day each month (1st or 15th)
Tone: Direct, honest, no spin. Bad news first if there is bad news.
Subject line: [Company] Monthly Update — [Month Year]
SUBJECT: Cure Consulting Group — [Month Year] Update
TL;DR (3 bullets max)
- [Biggest win this month — be specific with numbers]
- [Biggest challenge or miss — be honest]
- [One-line cash/runway status]
HIGHLIGHTS
List 3-5 wins. Each must be specific and measurable:
Good: "Vendly processed $47K GMV in March, up 32% MoM"
Bad: "Vendly is growing nicely"
Good: "Signed LOI with Baptist Health for Autograph pilot — 12 providers"
Bad: "Autograph had a good month for partnerships"
LOWLIGHTS
List 2-3 challenges. Never bury bad news. Never spin.
Good: "Missed Vendly merchant acquisition target (got 8, target was 15).
Root cause: onboarding flow too complex. Fix shipping next week."
Bad: "Merchant growth was slower than expected but we're optimistic"
Rules:
- Every lowlight must include: what happened, why, what you're doing about it
- If you missed a target from last month's update, call it out explicitly
- Investors respect honesty. They do not respect surprises at board meetings.
KEY METRICS
┌────────────────────┬──────────┬──────────┬──────────┬─────────┐
│ Metric │ Vendly │ Autograph│ Initiated│ Studio │
├────────────────────┼──────────┼──────────┼──────────┼─────────┤
│ MRR / Revenue │ $X,XXX │ $X,XXX │ $X,XXX │ $XX,XXX │
│ MoM Growth │ X% │ X% │ X% │ X% │
│ Users / Customers │ XXX │ XXX │ XXX │ — │
│ Key Product Metric │ GMV: $XX │ Scribes: X│ Coaches: X│ — │
│ Monthly Burn │ $X,XXX │ $X,XXX │ $X,XXX │ $XX,XXX │
├────────────────────┼──────────┴──────────┴──────────┼─────────┤
│ Cash Position │ │ $XXX,XXX│
│ Runway (months) │ │ XX │
└────────────────────┴────────────────────────────────┴─────────┘
Always include runway. Investors check this number first.
If runway < 6 months, flag it explicitly and state your plan.
PRODUCT UPDATES (per product, 2-3 sentences each)
Vendly: [What shipped, what's next]
Autograph: [What shipped, what's next]
The Initiated:[What shipped, what's next]
Antigravity: [What shipped, what's next]
TwntyHoops: [What shipped, what's next]
ASKS (always include at least one)
Be specific. Investors want to help but need direction.
Good: "Looking for intros to LATAM fintech operators, specifically anyone
who has scaled merchant onboarding in Mexico or Colombia"
Bad: "Let us know if you can help with anything"
Good: "Hiring a senior ML engineer for Autograph. Ideal: experience with
medical NLP. If you know anyone, reply and I'll send the JD."
Bad: "We're hiring"
Categories of asks:
- Introductions (to customers, partners, hires, other investors)
- Advice (specific strategic questions, not vague "what do you think")
- Follow-on or bridge (only when appropriate, with clear terms)
NEVER DO THESE:
- Skip a month because "nothing happened" (something always happened)
- Send it late without acknowledging the delay
- Use vanity metrics (total signups instead of active users)
- Hide bad news in the middle of a long paragraph
- Send a 3-page update (nobody reads past page 1)
- Use jargon your angels won't understand
- Forget the ask (you're leaving value on the table)
- Report metrics differently than last month (consistency builds trust)
- Round numbers up to make them look better
- Promise things you can't deliver by next month's update
12-15 slides maximum. Every slide has one message. If a slide needs a paragraph of explanation, it is a bad slide.
QUARTERLY BOARD DECK — Q[X] [YEAR]
Cure Consulting Group
[Date]
Slide 1: TITLE + AGENDA
Cure Consulting Group — Q[X] [YEAR] Board Review
Agenda: Portfolio Overview | Financials | Product Deep Dives | Decisions
Slide 2: EXECUTIVE SUMMARY
3-5 bullet points covering the quarter. Same TL;DR energy as the
monthly update, but for the full quarter.
Traffic light status per product: Green / Yellow / Red
Slide 3: PORTFOLIO HEALTH SCORECARD
┌─────────────┬────────┬──────────┬──────────┬───────────┬───────┐
│ Product │ Stage │ Revenue │ Growth │ Health │ Trend │
├─────────────┼────────┼──────────┼──────────┼───────────┼───────┤
│ Vendly │ [X] │ $XX,XXX │ XX% QoQ │ Green │ Up │
│ Autograph │ [X] │ $XX,XXX │ XX% QoQ │ Yellow │ Flat │
│ Initiated │ [X] │ $XX,XXX │ XX% QoQ │ Green │ Up │
│ Antigravity │ [X] │ $XX,XXX │ XX% QoQ │ Yellow │ Up │
│ TwntyHoops │ [X] │ $XX,XXX │ XX% QoQ │ Green │ Up │
└─────────────┴────────┴──────────┴──────────┴───────────┴───────┘
Health criteria:
Green: On track or ahead of plan
Yellow: Behind plan but recoverable, or facing known risks
Red: Significantly behind, requires board-level discussion
Slide 4: CONSOLIDATED FINANCIALS
- Total revenue (MRR breakdown by product)
- Total burn (allocated by product + shared costs)
- Cash position and runway
- Quarter-over-quarter comparison
- Use bar charts, not tables. One data story per chart.
Slide 5: REVENUE BREAKDOWN
Stacked bar chart: revenue by product over last 4 quarters
Show trajectory, not just this quarter's snapshot
Include revenue mix % (which products are driving growth)
Slide 6: BURN & RUNWAY
- Monthly burn trend line (last 6 months)
- Burn by category: engineering, marketing, infrastructure, G&A
- Runway at current burn rate
- Runway if revenue hits target
- Runway if revenue misses by 25%
Slides 7-10: PRODUCT DEEP DIVES (one per active product, 1 slide each)
For each product:
- Key metrics (3-4 max, with QoQ change)
- Top milestone achieved this quarter
- Top risk or blocker
- Next quarter's #1 priority
- 1 chart showing the metric that matters most
Per-product focus:
Vendly: GMV, merchant count, take rate, merchant retention
Autograph: Provider count, scribes completed, time saved per provider, pilot conversions
The Initiated: Coach accounts, athlete profiles, matching rate, platform engagement
Antigravity: Downloads/signups, DAU, agents deployed, community activity
TwntyHoops: Events held, attendance, social reach, sponsorship revenue
Slide 11: STRATEGIC DECISIONS
Frame 1-3 decisions the board needs to weigh in on.
Format per decision:
Context: [Why this decision matters now]
Options: [Option A] vs [Option B] (vs [Option C])
Recommendation:[What management recommends and why]
Ask: [Vote / Feedback / Approval needed]
Example decisions:
- Should we raise a bridge round or extend runway by cutting Product X?
- Should we pursue enterprise vs SMB for Autograph?
- Should we spin out Antigravity as a separate entity?
Slide 12: NEXT QUARTER PRIORITIES
Top 3 priorities for the studio. Tied to metrics.
Priority 1: [Goal] — measured by [metric] — target: [number]
Priority 2: [Goal] — measured by [metric] — target: [number]
Priority 3: [Goal] — measured by [metric] — target: [number]
Slide 13: APPENDIX — DETAILED FINANCIALS
Full P&L table, balance sheet summary, detailed burn breakdown.
This is the "for the record" slide. Board members who want detail will ask.
Slide 14: APPENDIX — PRODUCT ROADMAPS
High-level roadmap per product (next 2 quarters only, no 5-year fantasies)
Slide 15: APPENDIX — CAP TABLE SUMMARY (if relevant)
Current ownership, option pool remaining, next round implications
ONE message per slide. If you can't summarize the slide in 8 words, split it.
Data visualization over tables. Bar charts > line charts > tables.
No walls of text. Max 6 bullet points per slide, max 10 words per bullet.
Consistent color coding. Green/Yellow/Red for health. Same color per product everywhere.
White space is your friend. Crowded slides signal unclear thinking.
Every number needs context. "$50K MRR" means nothing. "$50K MRR (up 30% QoQ)" tells a story.
Consolidated financials across the full venture studio. This is the CFO's document.
CURE CONSULTING GROUP — PORTFOLIO FINANCIAL REPORT
Period: [Month/Quarter] [Year]
Prepared: [Date]
1. CONSOLIDATED P&L
┌──────────────────────┬──────────┬──────────┬──────────┬──────────┬──────────┬──────────┐
│ │ Vendly │ Autograph│ Initiated│ Antigrav │ TwntyH │ TOTAL │
├──────────────────────┼──────────┼──────────┼──────────┼──────────┼──────────┼──────────┤
│ Revenue │ $X,XXX │ $X,XXX │ $X,XXX │ $X,XXX │ $X,XXX │ $XX,XXX │
│ COGS │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($XX,XXX)│
│ Gross Profit │ $X,XXX │ $X,XXX │ $X,XXX │ $X,XXX │ $X,XXX │ $XX,XXX │
│ Gross Margin │ XX% │ XX% │ XX% │ XX% │ XX% │ XX% │
├──────────────────────┼──────────┼──────────┼──────────┼──────────┼──────────┼──────────┤
│ Engineering │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($XX,XXX)│
│ Marketing │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($XX,XXX)│
│ Infrastructure │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($XX,XXX)│
│ G&A (allocated) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($XX,XXX)│
├──────────────────────┼──────────┼──────────┼──────────┼──────────┼──────────┼──────────┤
│ Net Income (Loss) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($X,XXX) │ ($XX,XXX)│
└──────────────────────┴──────────┴──────────┴──────────┴──────────┴──────────┴──────────┘
2. SHARED COST ALLOCATION
Studio-level costs must be allocated. Use this framework:
Engineering shared services (DevOps, infra, code review): by engineering hours
G&A (legal, accounting, office): equal split or by revenue share
Marketing shared (brand, website): by attribution or equal split
Leadership time: by hours logged per product
Rule: Never let shared costs hide a product's true burn.
Every dollar must be attributed to a product or to "Studio Overhead."
3. REVENUE DETAIL
Per-product MRR/ARR breakdown:
Vendly: GMV $XXX,XXX × take rate X.X% = revenue $X,XXX
Autograph: XX providers × $XXX/mo = MRR $X,XXX
The Initiated: XX subscriptions × $XX/mo + sponsorships = $X,XXX
Antigravity: XX users × $XX/mo (freemium conversion X%) = $X,XXX
TwntyHoops: Events $X,XXX + Sponsorships $X,XXX + Media $X,XXX = $X,XXX
4. CASH POSITION & RUNWAY
Opening cash balance: $XXX,XXX
+ Revenue received: $XX,XXX
- Total expenses paid: ($XX,XXX)
- One-time costs: ($X,XXX)
= Closing cash balance: $XXX,XXX
Monthly burn rate: $XX,XXX
Runway at current burn: XX months
Runway if revenue grows 10% MoM: XX months
5. UNIT ECONOMICS PER PRODUCT
┌─────────────┬─────────┬─────────┬─────────┬─────────┬──────────┐
│ Metric │ Vendly │ Autograph│ Initiated│ Antigrav│ TwntyH │
├─────────────┼─────────┼─────────┼─────────┼─────────┼──────────┤
│ CAC │ $XXX │ $X,XXX │ $XX │ $XX │ N/A │
│ LTV │ $X,XXX │ $XX,XXX │ $XXX │ $XXX │ N/A │
│ LTV:CAC │ X.Xx │ X.Xx │ X.Xx │ X.Xx │ N/A │
│ Payback (mo)│ XX │ XX │ XX │ XX │ N/A │
│ Gross Margin│ XX% │ XX% │ XX% │ XX% │ XX% │
│ Churn (mo) │ X.X% │ X.X% │ X.X% │ X.X% │ N/A │
└─────────────┴─────────┴─────────┴─────────┴─────────┴──────────┘
TwntyHoops uses event-based economics, not SaaS metrics:
Revenue per event, cost per event, margin per event, sponsorship yield
6. INFRASTRUCTURE COSTS BY PRODUCT
┌─────────────────┬─────────┬─────────┬─────────┬─────────┬──────────┐
│ Service │ Vendly │ Autograph│ Initiated│ Antigrav│ TwntyH │
├─────────────────┼─────────┼─────────┼─────────┼─────────┼──────────┤
│ Firebase/GCP │ $XXX │ $XXX │ $XXX │ $XXX │ $XXX │
│ AI APIs │ $XX │ $X,XXX │ $XX │ $XXX │ $XX │
│ Stripe fees │ $XXX │ $XXX │ $XX │ $XX │ $XX │
│ Vercel/hosting │ $XX │ $XX │ $XX │ $XX │ $XX │
│ Other services │ $XX │ $XX │ $XX │ $XX │ $XX │
├─────────────────┼─────────┼─────────┼─────────┼─────────┼──────────┤
│ TOTAL │ $XXX │ $X,XXX │ $XXX │ $XXX │ $XXX │
└─────────────────┴─────────┴─────────┴─────────┴─────────┴──────────┘
Flag any product where AI API costs > 20% of revenue.
Flag any product where infra costs are growing faster than revenue.
7. SCENARIO MODELING
What if we pause Product X?
- Savings: $X,XXX/month (team reallocation, infra reduction)
- Lost revenue: $X,XXX/month
- Net impact on runway: +X months
- Strategic cost: [what do we lose beyond revenue?]
What if Product Y hits target?
- Revenue increase: $X,XXX/month by Month X
- Impact on runway: +X months
- Required investment to hit target: $X,XXX
- ROI: X:1 over 12 months
Model ownership, dilution, and exit scenarios. Get this wrong and founders, employees, and investors all lose.
1. CURRENT CAP TABLE
┌────────────────────┬──────────┬────────┬─────────────┐
│ Shareholder │ Shares │ % │ Type │
├────────────────────┼──────────┼────────┼─────────────┤
│ Founder 1 │ X,XXX,XXX│ XX.X% │ Common │
│ Founder 2 │ X,XXX,XXX│ XX.X% │ Common │
│ Angel Investor A │ XXX,XXX │ X.X% │ Preferred │
│ Angel Investor B │ XXX,XXX │ X.X% │ SAFE (conv) │
│ Employee Pool │ XXX,XXX │ XX.X% │ Options │
│ - Allocated │ XXX,XXX │ X.X% │ Options │
│ - Unallocated │ XXX,XXX │ X.X% │ Options │
├────────────────────┼──────────┼────────┼─────────────┤
│ TOTAL │ X,XXX,XXX│ 100.0% │ │
└────────────────────┴──────────┴────────┴─────────────┘
2. PRE/POST MONEY VALUATION SCENARIOS
┌──────────────────────┬───────────┬───────────┬───────────┐
│ │ Low │ Base │ High │
├──────────────────────┼───────────┼───────────┼───────────┤
│ Pre-money valuation │ $X.XM │ $X.XM │ $X.XM │
│ Round size │ $XXX K │ $XXX K │ $X.XM │
│ Post-money valuation │ $X.XM │ $X.XM │ $XX.XM │
│ New investor % │ XX.X% │ XX.X% │ XX.X% │
│ Founder dilution │ XX.X% │ XX.X% │ XX.X% │
│ Price per share │ $X.XX │ $X.XX │ $X.XX │
└──────────────────────┴───────────┴───────────┴───────────┘
3. OPTION POOL SIZING
Standard: 10-20% of fully diluted shares
Pre-seed/Seed: 10-15% (smaller team, fewer hires planned)
Series A: 15-20% (investors will require refresh)
Rule: Create or expand the pool BEFORE the round, not after.
The dilution comes from existing shareholders, not new investors.
Investors know this. You should too.
Current pool: X,XXX,XXX shares (XX.X% of fully diluted)
Allocated: X,XXX,XXX shares
Remaining: X,XXX,XXX shares
Recommended: [Expand to XX% if raising, current is sufficient if not]
4. SAFE/CONVERTIBLE NOTE CONVERSION
For each outstanding SAFE or note:
┌────────────────────┬───────────┬────────────┬───────────┬───────────┐
│ Instrument │ Amount │ Val Cap │ Discount │ Converts │
├────────────────────┼───────────┼────────────┼───────────┼───────────┤
│ SAFE — Investor A │ $XXX,XXX │ $X.XM │ — │ At next │
│ SAFE — Investor B │ $XXX,XXX │ $X.XM │ 20% │ priced rnd│
│ Conv Note — Inv C │ $XXX,XXX │ $X.XM │ 20% │ + interest│
└────────────────────┴───────────┴────────────┴───────────┴───────────┘
Conversion math:
SAFE with cap: shares = investment / (cap / fully diluted shares)
SAFE with discount: shares = investment / (price × (1 - discount))
Use whichever gives the investor MORE shares (investor-favorable)
Convertible note: same as SAFE, but add accrued interest to principal
Interest: principal × rate × (days elapsed / 365)
5. DILUTION WATERFALL — PROPOSED ROUND
┌────────────────────┬───────────┬──────────┬───────────┬──────────┐
│ Shareholder │ Pre-Round │ Pre % │ Post-Round│ Post % │
├────────────────────┼───────────┼──────────┼───────────┼──────────┤
│ Founder 1 │ X,XXX,XXX │ XX.X% │ X,XXX,XXX │ XX.X% │
│ Founder 2 │ X,XXX,XXX │ XX.X% │ X,XXX,XXX │ XX.X% │
│ Existing Investors │ XXX,XXX │ X.X% │ XXX,XXX │ X.X% │
│ SAFE Conversions │ — │ — │ XXX,XXX │ X.X% │
│ New Option Pool │ — │ — │ XXX,XXX │ XX.X% │
│ New Investors │ — │ — │ X,XXX,XXX │ XX.X% │
├────────────────────┼───────────┼──────────┼───────────┼──────────┤
│ TOTAL │ X,XXX,XXX │ 100.0% │ X,XXX,XXX │ 100.0% │
└────────────────────┴───────────┴──────────┴───────────┴──────────┘
6. EXIT WATERFALL (WHO GETS WHAT)
Model at 3 exit values: $5M, $20M, $50M (or use actual scenarios)
Liquidation preferences matter:
1x non-participating preferred: investor gets back their money OR converts (whichever is more)
1x participating preferred: investor gets back their money AND their pro-rata share
No preference (common): everyone splits pro-rata
┌────────────────────┬──────────┬──────────┬──────────┐
│ Shareholder │ $5M Exit │ $20M Exit│ $50M Exit│
├────────────────────┼──────────┼──────────┼──────────┤
│ Founder 1 │ $X.XM │ $X.XM │ $XX.XM │
│ Founder 2 │ $X.XM │ $X.XM │ $XX.XM │
│ Investors (pref) │ $X.XM │ $X.XM │ $X.XM │
│ Employees (options)│ $XXX,XXX │ $X.XM │ $X.XM │
├────────────────────┼──────────┼──────────┼──────────┤
│ TOTAL │ $5.0M │ $20.0M │ $50.0M │
└────────────────────┴──────────┴──────────┴──────────┘
Studio-specific consideration:
If Cure holds equity in each product entity separately, model the waterfall
per entity. If Cure is a single entity with product lines, model once.
This distinction matters enormously at exit. Decide the structure early.
The most important financial exercise for an early-stage studio. Know exactly when you run out of money under every scenario.
1. CURRENT BURN ANALYSIS
Fixed costs (don't change with revenue):
Salaries & contractors: $XX,XXX/month
Office / coworking: $X,XXX/month
Tools & subscriptions: $X,XXX/month
Legal & accounting: $X,XXX/month
Insurance: $XXX/month
Total fixed: $XX,XXX/month
Variable costs (scale with usage/customers):
Infrastructure (Firebase, GCP): $X,XXX/month
AI API costs (OpenAI, etc.): $X,XXX/month
Payment processing (Stripe): $XXX/month
Marketing spend: $X,XXX/month
Total variable: $X,XXX/month
Total monthly burn: $XX,XXX
Monthly revenue: $XX,XXX
Net burn: $XX,XXX
Cash position: $XXX,XXX
Runway at current net burn: XX months
2. REVENUE TRAJECTORY SCENARIOS (12-month projection)
┌───────┬───────────────┬───────────────┬───────────────┐
│ Month │ Conservative │ Base │ Optimistic │
├───────┼───────────────┼───────────────┼───────────────┤
│ 1 │ $XX,XXX │ $XX,XXX │ $XX,XXX │
│ 3 │ $XX,XXX │ $XX,XXX │ $XX,XXX │
│ 6 │ $XX,XXX │ $XX,XXX │ $XX,XXX │
│ 9 │ $XX,XXX │ $XX,XXX │ $XX,XXX │
│ 12 │ $XX,XXX │ $XX,XXX │ $XX,XXX │
├───────┼───────────────┼───────────────┼───────────────┤
│ Runway│ XX months │ XX months │ XX months │
└───────┴───────────────┴───────────────┴───────────────┘
Conservative: current growth continues, no new products launch
Base: planned launches hit, moderate growth
Optimistic: all targets hit, viral growth or enterprise deal closes
3. SENSITIVITY TABLE — WHAT MOVES THE NEEDLE
┌─────────────────────────────┬───────────────┬───────────────┐
│ Change │ Monthly Impact │ Runway Impact │
├─────────────────────────────┼───────────────┼───────────────┤
│ Cut 1 engineer │ -$X,XXX burn │ +X months │
│ Pause TwntyHoops │ -$X,XXX burn │ +X months │
│ Vendly hits 50 merchants │ +$X,XXX rev │ +X months │
│ Autograph closes enterprise │ +$XX,XXX rev │ +X months │
│ Raise $250K bridge │ +$250K cash │ +X months │
│ Cut marketing 50% │ -$X,XXX burn │ +X months │
│ Move to cheaper infra │ -$X,XXX burn │ +X months │
└─────────────────────────────┴───────────────┴───────────────┘
4. BREAK-EVEN ANALYSIS PER PRODUCT
For each product, answer: what does it take to cover its own costs?
Vendly: XXX merchants at $XX avg monthly revenue = break-even
Autograph: XX providers at $XXX/month = break-even
The Initiated: X,XXX subscribers at $XX/month = break-even
Antigravity: X,XXX users at $XX/month = break-even
TwntyHoops: XX events/year at $X,XXX avg net per event = break-even
5. DECISION FRAMEWORK
When to RAISE:
- Runway < 6 months and metrics trending up
- Clear use of funds (hire X, launch Y, scale Z)
- Favorable market conditions for your stage
- Never raise out of desperation. Investors smell it.
When to CUT:
- Runway < 4 months with no raise in progress
- A product's metrics have been flat for 3+ months despite investment
- Cost to acquire next customer is rising, not falling
- Cut fast. Cut once. Then focus.
When to DOUBLE DOWN:
- Product shows clear PMF signals (organic growth, low churn, NPS > 50)
- Unit economics are improving month over month
- Marginal cost of growth is decreasing
- Capital deployed here has higher ROI than other products in portfolio
Investors will request these documents during due diligence. Have them ready before you start fundraising, not after the first meeting.
DATA ROOM STRUCTURE
Organize in a shared drive (Google Drive or DocSend). Number folders for order.
01 — CORPORATE
[ ] Certificate of Incorporation / Articles of Organization
[ ] Bylaws / Operating Agreement
[ ] Board meeting minutes (all)
[ ] Board consent resolutions
[ ] Stockholder/member agreements
[ ] Cap table (current, fully diluted, with all SAFEs/notes)
[ ] 409A valuation (if applicable)
[ ] State registrations / qualifications
02 — FINANCIALS
[ ] Profit & loss statement (trailing 12 months, monthly)
[ ] Balance sheet (current)
[ ] Cash flow statement (trailing 12 months)
[ ] Bank statements (last 6 months)
[ ] Financial projections (12-24 months, with assumptions documented)
[ ] Revenue breakdown by product
[ ] Burn breakdown by product
[ ] Accounts receivable / payable aging
03 — FUNDRAISING
[ ] Pitch deck (current version)
[ ] Executive summary / one-pager
[ ] Previous term sheets (if any)
[ ] Outstanding SAFEs / convertible notes (copies)
[ ] Use of funds plan (this round)
[ ] Prior investors list with amounts and terms
04 — PRODUCT
[ ] Product demos (recorded or live links)
[ ] Architecture overview (1-2 pages, not a novel)
[ ] Product roadmap (next 6-12 months)
[ ] User/customer testimonials or case studies
[ ] Screenshots / UI walkthroughs
[ ] App Store / Play Store links (if live)
05 — METRICS
[ ] Cohort retention analysis (by month, by product)
[ ] Growth charts (users, revenue, GMV — trailing 12 months)
[ ] Unit economics summary (CAC, LTV, LTV:CAC per product)
[ ] Funnel metrics (signup to activation to payment)
[ ] NPS or satisfaction scores (if collected)
[ ] Churn analysis with reasons
06 — TEAM
[ ] Org chart
[ ] Founder bios / LinkedIn profiles
[ ] Key hire profiles
[ ] Hiring plan (next 12 months)
[ ] Employee stock option grants (summary, not individual)
[ ] Advisory board (if any)
07 — LEGAL
[ ] IP assignment agreements (all founders and contractors)
[ ] Employee/contractor agreements (template)
[ ] Material contracts (customers, vendors, partners)
[ ] Pending or threatened litigation (disclose or confirm none)
[ ] Insurance policies (D&O, E&O, general liability)
08 — COMPLIANCE (product-specific)
[ ] HIPAA BAA and compliance documentation (Autograph)
[ ] Privacy policies (all products)
[ ] Terms of Service (all products)
[ ] Data processing agreements (if handling EU data)
[ ] SOC 2 status or roadmap (if applicable)
[ ] COPPA compliance (if applicable, The Initiated — if minors)
09 — TECHNICAL
[ ] Security review summary (see /security-review skill)
[ ] Infrastructure overview (cloud providers, architecture diagram)
[ ] Uptime / reliability metrics (if tracked)
[ ] Open source license compliance
[ ] Data backup and disaster recovery plan
READINESS RULES:
- All documents must be current (within 30 days)
- Label every document with date and version
- Redact sensitive PII where possible
- Use view-only links with tracking (DocSend preferred over raw Google Drive)
- Have a "data room ready" date on your fundraising timeline
- Budget 2-3 weeks to assemble from scratch, 2-3 days to refresh
Define exactly what to measure per product. No vanity metrics. Every KPI must be actionable — if it moves, you know what to do.
VENDLY — LATAM MERCHANT OS (Marketplace Model)
┌──────────────────────┬──────────────────────────────────────────────┬───────────┐
│ KPI │ Formula │ Target │
├──────────────────────┼──────────────────────────────────────────────┼───────────┤
│ GMV │ Total transaction volume processed │ $XXX K/mo │
│ Take Rate │ Revenue / GMV │ 2-5% │
│ Active Merchants │ Merchants with 1+ transaction in last 30 days│ XXX │
│ Merchant Retention │ Merchants active this month / active last mo │ > 85% │
│ Avg Revenue/Merchant │ Revenue / active merchants │ $XX/mo │
│ TPV Growth (MoM) │ (This month GMV - last month GMV) / last mo │ > 15% │
│ Merchant CAC │ Sales + marketing spend / new merchants │ < $XXX │
│ Merchant LTV │ Avg revenue/merchant / monthly churn rate │ > $X,XXX │
│ Onboarding Time │ Median days from signup to first transaction │ < 7 days │
│ Support Tickets/Merch│ Monthly support tickets / active merchants │ < 1.0 │
└──────────────────────┴──────────────────────────────────────────────┴───────────┘
AUTOGRAPH — AI MEDICAL SCRIBE (SaaS / Healthcare)
┌──────────────────────┬──────────────────────────────────────────────┬───────────┐
│ KPI │ Formula │ Target │
├──────────────────────┼──────────────────────────────────────────────┼───────────┤
│ MRR │ Active providers × price per provider │ $XX K/mo │
│ Active Providers │ Providers who completed 1+ scribe this month │ XXX │
│ Scribes Completed │ Total AI scribes generated this month │ X,XXX/mo │
│ Time Saved/Provider │ Avg minutes saved per provider per day │ > 60 min │
│ Accuracy Rate │ Scribes accepted without major edits / total │ > 95% │
│ Pilot Conversion │ Pilots converted to paid / total pilots ended │ > 60% │
│ Provider NPS │ Net Promoter Score from provider surveys │ > 50 │
│ Churn (monthly) │ Providers lost / providers at start of month │ < 3% │
│ NRR │ (Start MRR + expansion - churn) / Start MRR │ > 110% │
│ HIPAA Incidents │ Security/privacy incidents in period │ 0 │
│ AI Cost/Scribe │ LLM API cost per scribe generated │ < $0.50 │
└──────────────────────┴──────────────────────────────────────────────┴───────────┘
THE INITIATED — WOMEN'S BASKETBALL RECRUITING PLATFORM
┌──────────────────────┬──────────────────────────────────────────────┬───────────┐
│ KPI │ Formula │ Target │
├──────────────────────┼──────────────────────────────────────────────┼───────────┤
│ Coach Accounts │ Verified college coach accounts on platform │ XXX │
│ Athlete Profiles │ Complete athlete profiles (video + stats) │ X,XXX │
│ DAU / MAU │ Daily active / monthly active users │ > 25% │
│ Matching Rate │ Athletes contacted by coaches / total athletes│ > XX% │
│ Coach Engagement │ Avg profiles viewed per coach per session │ > 10 │
│ Platform Stickiness │ DAU / MAU ratio │ > 20% │
│ Athlete Completion │ Profiles with video + stats + GPA / total │ > 70% │
│ Subscription Revenue │ Paid subscriptions × price │ $X,XXX/mo │
│ Recruiting Outcomes │ Offers/commits attributed to platform │ XX/season │
│ Coach Retention (Q) │ Coaches active this quarter / last quarter │ > 80% │
└──────────────────────┴──────────────────────────────────────────────┴───────────┘
ANTIGRAVITY — AI AGENT ORCHESTRATION IDE (Dev Tools)
┌──────────────────────┬──────────────────────────────────────────────┬───────────┐
│ KPI │ Formula │ Target │
├──────────────────────┼──────────────────────────────────────────────┼───────────┤
│ Total Signups │ Cumulative accounts created │ X,XXX │
│ DAU │ Users who opened IDE in last 24 hours │ XXX │
│ Weekly Active │ Users active 3+ days in last 7 │ XXX │
│ Agents Deployed │ Total agent workflows deployed to production │ X,XXX │
│ Retention (D7) │ Users active on day 7 / users signed up 7d ago│ > 40% │
│ Retention (D30) │ Users active on day 30 / signed up 30d ago │ > 20% │
│ Freemium Conversion │ Paid users / total active users │ > 5% │
│ MRR │ Paid users × avg price │ $X,XXX/mo │
│ Community PRs │ Open source contributions per month │ XX/mo │
│ NPS │ Net Promoter Score from user surveys │ > 40 │
│ Avg Session Duration │ Median minutes per IDE session │ > 20 min │
└──────────────────────┴──────────────────────────────────────────────┴───────────┘
TWNTYHOOPS — BASKETBALL MEDIA & EVENTS
┌──────────────────────┬──────────────────────────────────────────────┬───────────┐
│ KPI │ Formula │ Target │
├──────────────────────┼──────────────────────────────────────────────┼───────────┤
│ Events Held │ Total events this period │ XX/quarter│
│ Avg Attendance │ Total attendees / events held │ XXX/event │
│ Revenue per Event │ (Tickets + sponsorships + merch) / events │ $X,XXX │
│ Cost per Event │ Total event costs / events held │ $X,XXX │
│ Margin per Event │ (Revenue - cost) / revenue per event │ > 40% │
│ Social Reach │ Total followers across platforms │ XX,XXX │
│ Engagement Rate │ (Likes + comments + shares) / impressions │ > 3% │
│ Sponsorship Revenue │ Total sponsorship deals closed this period │ $XX,XXX/Q │
│ Sponsor Retention │ Returning sponsors / total sponsors last period│ > 70% │
│ Content Pieces │ Videos, articles, posts published │ XX/week │
│ Email List Size │ Total newsletter subscribers │ X,XXX │
│ Email Open Rate │ Opens / emails sent │ > 30% │
└──────────────────────┴──────────────────────────────────────────────┴───────────┘
DASHBOARD RULES:
- Update every KPI weekly, report monthly (at minimum)
- Every KPI needs a target. A number without a target is just a number.
- Show trailing 3-month trend, not just current value
- Red/yellow/green status based on % of target achieved
- If a KPI has been red for 3 months, escalate to board or kill the initiative
- Never add a KPI without removing one. Dashboard bloat kills focus.
- Source of truth: one spreadsheet or dashboard tool, not scattered across Notion/Sheets/Slack
Generate using Write:
docs/investor-updates/{YYYY-MM}.md — populated templatedocs/board-deck-outline.md — slide-by-slide structuremonitoring/investor-kpi.json — dashboard templateanalytics/investor-metrics.sql — queries for each KPIRelated skills for investor reporting workflows:
/saas-financial-model — Deep unit economics and pricing analysis/engineering-cost-model — Build costs and infrastructure forecasting/sdlc — Product roadmap artifacts for board decks/analytics-implementation — Event tracking to feed KPI dashboards/security-review — Security posture for data room/legal-doc-scaffold — Legal docs for data room compliance section