Fundraising

Scope

Covers

• Deciding whether to raise venture funding (vs bootstrapping / delaying / alternatives) and articulating the trade-offs
• Designing a round (amount, timeline, milestone, target investor profile) without pretending to give legal/tax advice
• Building an investor-ready narrative and a pitch deck outline optimized for first impressions
• Running the fundraising process as a pipeline (target list, outreach, follow-ups, rejection handling, momentum)
• Preparing for diligence (data-room checklist + FAQs/objections) and reducing “unknown unknowns”

When to use

• “Should I raise venture capital or bootstrap?”
• “Help me build a pitch deck narrative and a strong first slide.”
• “I need an investor outreach plan and a pipeline tracker.”
• “I’m starting a pre-seed/seed raise; help me run the process end-to-end.”

When NOT to use

• You need to build a founder-led sales motion or close your first customers — use founder-sales (this pack raises capital; that pack generates revenue)
• You want to validate a startup idea before raising — use startup-ideation (validate the idea first, then raise)
• You need help with presentation delivery, storytelling mechanics, or slide design — use giving-presentations (this pack builds the narrative and deck outline; that pack covers delivery and design)
• You have a job offer to negotiate (not an investment round) — use negotiating-offers
• You need legal, tax, or securities advice (term sheets, SAFE/notes, incorporation, compliance) — involve qualified professionals
• You’re raising grants/donations or structured debt (use a fundraising/grants/debt-specific workflow instead)
• You only want visual slide design polish with no strategy/process work
• You’re in an immediate liquidity crisis where the only viable path is emergency financing within days (this skill can help structure messaging, but you should prioritize urgent financial triage with experts)

Inputs

Minimum required

• Company snapshot: what you build, who it’s for, and why now
• Stage + traction (or pre-traction proof), plus 1–3 key metrics (even proxies)
• Team snapshot (founders, key strengths, gaps you’re hiring for)
• Runway + constraints (cash, time, geography, intro network, fundraising window)
• Fundraising intent: why raise, target amount (or range), and what milestone it buys

Missing-info strategy

• Ask 3–5 questions at a time from references/INTAKE.md.
• If specifics are missing, proceed with labeled assumptions and ranges (never invent exact numbers).
• Do not request sensitive credentials or confidential customer/employee data; use anonymized examples.

Outputs (deliverables)

Produce a Fundraising Pack (Markdown in chat; or as files if requested) in this order:

1) Raise Decision Memo (VC vs bootstrap/delay; trade-offs; “if we raise” vs “if we don’t” plan) 2) Round Design Brief (amount, timing, milestone, use of funds, target investor profile) 3) Pitch Narrative + Deck Outline (including a high-signal first slide + talk track) 4) Investor ICP + Target List + Pipeline Tracker (with weekly activity targets) 5) Outreach + Follow-up Scripts (warm intro ask, cold email, post-meeting follow-up) 6) Diligence Prep (data-room checklist + FAQ/objection responses) 7) Operating Cadence (weekly dashboard, “100 no’s” resilience plan, next-14-days action plan) 8) Risks / Open questions / Next steps (always)

Templates: references/TEMPLATES.md Expanded guidance: references/WORKFLOW.md

Workflow (8 steps)

1) Intake + constraints snapshot

• Inputs: user context; references/INTAKE.md.
• Actions: Capture stage, runway, constraints, timing, and goal. Separate “must be true” vs “nice to have”. Identify what would make fundraising a mistake.
• Outputs: Context snapshot + assumptions/unknowns list.
• Checks: Timeline has dates; runway is stated (or explicitly unknown); constraints are explicit.

2) Decide whether to raise (and why)

• Inputs: goals, constraints, risk tolerance, business model.
• Actions: Write a Raise Decision Memo: why raise, why not, and the “venture treadmill” trade-off (growth expectations, dilution, speed). Propose alternatives (delay, revenue-first, angels, strategic, debt) where appropriate.
• Outputs: Raise Decision Memo with a clear recommendation + decision criteria.
• Checks: Recommendation is falsifiable (“we raise if X by date Y”); non-VC path is not hand-waved.

3) Design the round (make the plan fundable)

• Inputs: runway, burn (or plan), milestone, hiring needs, market timing.
• Actions: Define raise amount range, timing, and the milestone it buys. Specify investor profile (stage, check size, thesis, geography) and a simple “use of funds” narrative.
• Outputs: Round Design Brief.
• Checks: Amount ↔ milestone is coherent; plan fits constraints; assumptions are explicit.

4) Build the pitch narrative + first impression assets

• Inputs: product, ICP, wedge, traction/proof, insights from Steps 1–3.
• Actions: Draft a crisp one-liner, the “strongest point” for slide 1, and a deck outline that answers: problem, solution, why now, why you, why win, why invest.
• Outputs: Pitch Narrative + Deck Outline (+ talk track).
• Checks: First slide passes the 10-second test (what it is, for whom, why it matters); narrative has evidence, not vibes.

5) Build the investor pipeline (target list + math)

• Inputs: target investor profile; network; constraints.
• Actions: Create an ICP and a prioritized target list. Set pipeline math (how many intros/meetings/week) and define a tracking table.
• Outputs: Investor ICP + Target List + Pipeline Tracker.
• Checks: Targets match round design; outreach plan is schedulable; next 7 days have concrete outreach tasks.

6) Execute outreach + meetings (run the “100 no’s” process)

• Inputs: scripts; target list; calendar.
• Actions: Draft outreach messages, run outreach cadence, and standardize meeting flow + follow-ups. Track “nos” as data (rejection reasons) and iterate the pitch.
• Outputs: Outreach + Follow-up Scripts + meeting agenda + iteration log.
• Checks: Every meeting has a next step; follow-ups go out within 24 hours; learnings are captured weekly.

7) Prep diligence (reduce friction)

• Inputs: likely diligence asks; current docs.
• Actions: Create a lightweight data-room checklist and an FAQ/objection response sheet. Identify the 3–5 biggest diligence gaps and a plan to close them.
• Outputs: Diligence Prep checklist + FAQ.
• Checks: No claims without supporting artifacts; sensitive info is handled carefully.

8) Quality gate + finalize the pack

• Inputs: full draft pack.
• Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Tighten weak sections. Add Risks / Open questions / Next steps and a next-14-days action plan.
• Outputs: Final Fundraising Pack.
• Checks: Pack is decision-ready, narrative-coherent, and process-executable.

Quality gate (required)

• Use references/CHECKLISTS.md and references/RUBRIC.md.
• Always include: Risks, Open questions, Next steps.

Examples

Example 1 (pre-seed): “We’re 2 founders building a B2B workflow tool. We have 5 design partners and 2 pilots. We have 6 months runway and want to raise $1.5–2.0M. Use fundraising to produce the full Fundraising Pack including a deck outline and investor pipeline tracker.” Expected: decision memo + round design + deck outline (strong first slide) + target list + outreach scripts.

Example 2 (seed with traction): “We’re at $60k MRR and growing 10% MoM. We’re debating whether to raise now or wait 6 months. Use fundraising to help us decide and create an outreach plan if we choose to raise.” Expected: raise-vs-wait decision memo with criteria + round design options + pipeline plan.

Boundary example: “Draft a SAFE agreement and tell me what valuation I should take.” Response: out of scope for legal/pricing advice; offer to produce the negotiation inputs (round design assumptions, comps proxy approach, questions for counsel) and a fundraising process plan.

Anti-patterns

1. Raising without a thesis — Jumping into investor outreach without a clear “why raise, why now, why this amount” decision memo. The raise decision memo is not optional — it prevents raising money you don't need or raising too little to hit the next milestone.
2. Deck-first, narrative-last — Designing slides before having a crisp pitch narrative. The narrative (problem, wedge, why now, why you, why win) should drive the deck, not the other way around. Start with a strong one-liner and first-slide story.
3. Spray-and-pray outreach — Sending the same cold email to 200 investors without ICP filtering. Effective fundraising targets 30-50 high-fit investors with warm paths, not a mass blast. Track signal-to-noise and iterate weekly.
4. Ignoring the “100 no's” reality — Expecting a quick close and getting demoralized by rejection. The operating cadence should include resilience planning: rejection tracking, pitch iteration log, weekly learnings, and emotional support.
5. Diligence denial — Waiting for a term sheet to start preparing for diligence. Build the data room checklist and FAQ/objection responses in parallel with outreach, not as an afterthought.