• Needs to build or review a pitch deck for investors
• Asks about term sheet terms, investor rights, or negotiation strategy
• Is preparing a data room for due diligence
• Wants to write an investor update or board update
• Needs to model dilution, pro-rata, or ownership across multiple rounds
• Is deciding between a SAFE, convertible note, or priced round
• Asks about valuation, cap table management, or option pool sizing
• Needs to build or manage an investor pipeline and outreach strategy

• SaaS metrics analysis or revenue modeling - use the saas-metrics skill
• Legal document drafting or securities law advice - recommend engaging counsel

1. Raise when you don't need to - The best time to fundraise is when you have leverage: strong metrics, multiple term sheets, or a credible alternative path to profitability. Fundraising from a position of desperation forces bad terms. Extend runway, cut burn, reach a milestone - then open the round.
2. Fundraising is a full-time job - timebox it - A founder running a process while also running the company will do both poorly. Set a defined window (6-8 weeks for seed, 8-12 weeks for Series A), run all investor conversations in parallel to create urgency, and close fast. Drag kills momentum and leaks information.
3. SAFE > convertible note for early stage - SAFEs have no maturity date, no interest accrual, and no debt on the cap table. Convertible notes accrue interest and have a maturity date that creates pressure to convert or repay. For pre-seed and seed, default to a YC SAFE (post-money valuation cap, MFN clause). Use convertible notes only if investors insist or if you need bridge financing on an existing priced round.
4. Dilution compounds - be strategic - Every round dilutes all prior shareholders proportionally. A 20% seed round, 20% Series A, and 20% Series B leaves founders with 51% of what they started with before any option pool refreshes. Model dilution through your target exit before agreeing to any terms. The option pool shuffle (investors requiring a larger pool pre-money) is the single most founder-dilutive mechanic in term sheets.
5. Investor-market fit matters - The wrong investor is worse than no investor. A consumer VC leading a B2B enterprise deal, or a growth fund leading a seed round, creates a board dynamic and expectation mismatch that will resurface at every decision point. Research every investor's portfolio, check-size history, and founder reputation before taking a meeting.

• One idea per slide; if a slide needs two headers it is two slides
• No more than 30 words of body text per slide
• Use real data over projections wherever possible
• Market size must be bottom-up: Total Addressable (universe) > Serviceable Addressable (reachable) > Serviceable Obtainable (realistic 3-year target)

Avoid bullet-point walls. Investors scan decks in 3-4 minutes before deciding whether to read deeply. Every slide must work as a visual first.

1. Get term sheets from multiple investors before engaging on terms
2. Use competing terms as leverage - never share the other term sheet directly
3. Focus on 3-5 material terms only; fighting every clause signals inexperience
4. Ask for explanation on any term you don't understand before agreeing
5. Have counsel review before signing - term sheets are binding on exclusivity

references/term-sheet-guide.md

/corporate
  Certificate of Incorporation, Bylaws, Prior financing docs, Cap table (Carta export)
/financials
  Monthly P&L (24 months), Balance sheet, Cash flow statement, Financial model
/legal
  IP assignments, Customer contracts (anonymized), Employment agreements, Key vendor contracts
/product
  Product roadmap, Architecture overview, Security documentation, Key metrics dashboard
/team
  Org chart, Key employee offer letters, Founder backgrounds / LinkedIns
/customers
  Reference customer list (name, contact, tenure, ARR), Case studies, NPS data
/market
  Competitive landscape, Market research, Press coverage

• Cap table has missing IP assignments or unvested founder shares without a cliff/schedule
• Revenue recognition is inconsistent (mixing cash and accrual)
• Open litigation or IP disputes without documented resolution
• Customer concentration: one customer > 30% of ARR needs a narrative

Send the data room link only after an investor has expressed intent to move forward. Broad distribution of financials before interest is confirmed leaks sensitive data to potential competitors in your space.

Subject: [Company] - [Month Year] Update

TL;DR: [2-3 sentences: key wins, key challenges, key ask]

METRICS
- MRR: $X (+Y% MoM)
- Customers: N (+Z this month)
- Runway: N months at current burn
- [1-2 stage-appropriate metrics: DAU, conversion rate, NRR]

WINS
- [Concrete achievement #1]
- [Concrete achievement #2]

CHALLENGES
- [Honest challenge #1 and what you are doing about it]

PRIORITIES THIS MONTH
- [Focus #1]
- [Focus #2]

ASK
- [Specific intro request: "Looking for a VP of Sales with PLG background"]
- [Specific advice: "Know any reliable tax counsel in Delaware?"]

• Send on a predictable cadence (same week each month/quarter)
• Be honest about challenges - investors who find out later feel blindsided
• Always include a specific ask; it gives investors a way to add value
• Keep to under 300 words; use the template above as a hard cap
• Reply to investor responses within 24 hours

Pre-money valuation: $8M
Investment: $2M
Post-money valuation: $10M
New investor ownership: $2M / $10M = 20%

Existing shareholders retain: 80% of prior holdings

If founders owned 100% before:
  After seed: 80%
  After Series A (20% dilution): 80% * 80% = 64%
  After Series B (15% dilution): 64% * 85% = 54.4%
  After option pool refreshes (~5% each round): subtract 5pp per round

Investor requires 15% option pool post-round on a $10M post-money round.
  Pool sized pre-money: 15% of $10M = $1.5M comes from existing shareholders
  Founders bear $1.5M of dilution before the round closes
  Effective pre-money valuation is reduced by $1.5M
  Prefer: size the option pool post-money, or negotiate a smaller pre-money pool

• Founder % at each round close
• Founder % at exit (after all dilution events)
• Return multiple to founders at different exit valuations ($50M, $100M, $500M)

• Pre-product or pre-revenue with high valuation uncertainty
• Rolling close across multiple angels ($25K-$500K checks)
• YC batch companies raising alongside Demo Day

• Leading institutional VC with $3M+ check size requires priced terms
• Company is profitable and has negotiating leverage on valuation
• Prior SAFEs are at multiple different caps creating cap table complexity

• Valuation cap (sets maximum conversion price - lower benefits investor)
• Discount rate (5-20% off next round price - standard is 10-20%)
• MFN clause (most favored nation - ensures this SAFE gets best terms if you issue future SAFEs at better terms; include on uncapped SAFEs)
• Pro-rata rights (right to invest in next round to maintain %)

Target -> Intro Requested -> First Meeting -> Follow-up/Diligence -> Term Sheet -> Closed

• Firm name, partner name, contact email
• Stage (above)
• Date of last contact
• Next action + due date
• Check size range / typical first check
• Portfolio relevance (companies they have backed in your space)
• Warm intro source
• Notes on fit / reservations

1. Identify 50-75 target investors (not 200; quality over quantity)
2. Prioritize by: thesis fit > portfolio fit > check size > brand
3. Lead with warm intros (investor > investor intro is highest conversion)
4. Send a concise cold email if no warm path: 3 sentences max, attach deck
5. First meeting: 30-45 min, no slides - tell the story conversationally
6. Follow-up within 24h with deck and data room link if interest shown
7. Create artificial scarcity: all term sheet conversations happen simultaneously

Never give an investor an indefinite timeline to decide. Set a soft close date ("We are planning to close this round by [date]") and hold it.

1. Term sheets are binding on exclusivity, not economics - Signing a term sheet typically triggers a no-shop clause (30-90 days) that prevents you from soliciting other investors. You are not committed to accepting the deal, but you are committed to not running a competing process. Read the exclusivity clause carefully before signing.
2. Post-money SAFE valuation cap is not the same as company valuation - A $10M post-money SAFE cap means the investor's ownership is calculated as if the company is worth $10M after their investment. If you raise $1M on a $10M post-money SAFE, you have given away 10% - not a fraction of $10M minus $1M. Model this explicitly before issuing multiple SAFEs at different caps.
3. Option pool shuffle happens before close, not after - If a lead investor requires a 15% option pool "post-round" but structures it pre-money, the existing shareholders (founders) absorb the full dilution of creating the pool before the round closes. The effective pre-money valuation is reduced by the pool value. Always model both scenarios before agreeing.
4. Data room access given too early leaks competitive intelligence - Sharing your full data room with investors who are still in early conversations exposes your customer list, pricing, and financial model to potential competitors in your space (many VCs hold portfolio companies that compete with you). Gate data room access until a term sheet or strong letter of intent.
5. Pro-rata rights compound dilution in down rounds - Pro-rata rights allow investors to maintain their ownership percentage in future rounds. In a strong up round this is manageable. In a down round, investors exercising pro-rata to avoid dilution may force founders to take worse terms or face a harder close. Negotiate pro-rata rights to apply only above a minimum round size.

references/

• references/term-sheet-guide.md

  - Complete term-by-term breakdown with founder-friendly vs investor-friendly ranges and negotiation tactics. Load when reviewing or negotiating a specific term sheet.

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