YC Startup School — Module 7: Fundraising and Company Building
Official Curriculum
- 📺 How Startup Fundraising Works in 2022 — Brad Flora (YC Partner) ✅ transcript available
- 📺 How to Apply and Succeed at Y Combinator — Dalton Caldwell (YC Managing Director) ✅ transcript available
Instructions
- Read ALL transcript files from
${CLAUDE_PLUGIN_ROOT}/skills/yc-7-fundraising-and-company-building/references/:how-startup-fundraising-works.md— Brad Flora (YC Partner)how-to-apply-and-succeed-at-yc.md— Dalton Caldwell (YC Managing Director)
- Present key frameworks from each lecture with speaker attribution
- Assess the user's fundraising stage, YC interest, and legal/cap table hygiene
- Generate a workbook-style self-assessment derived from the lectures
- Save to
knowledge/yc-startup-school/module-7-assessment.md - Run the interactive Self-Assessment Workbook:
- Ask each question ONE AT A TIME using AskUserQuestion
- Wait for the user's response before asking the next question
- After each answer, provide brief feedback connecting their response to the module's frameworks
- After all questions, synthesize their answers into a personalized assessment
- Save the completed assessment (questions + answers + synthesis) to the appropriate knowledge path
Key Frameworks
How Startup Fundraising Works (Brad Flora)
- The fundraising journey: Bootstrapping → pre-seed (friends/angels) → seed (institutional) → Series A (VC)
- SAFE mechanics: Simple Agreement for Future Equity — valuation cap, discount, MFN clause. Post-money SAFE is the current standard.
- Valuation cap: The price ceiling at which your SAFE converts. Lower = better for investor. Higher = you believe more in your future value.
- Priced rounds vs. convertible: SAFEs and notes are faster/cheaper. Priced rounds set a definitive valuation with preferred stock.
- Investor psychology: Investors fund lines, not dots — show consistent trajectory. Warm intro > cold outreach by 10x.
- Fundraising process: Build the list → get intros → run parallel conversations → create urgency → close → wire transfer before celebrating
- Common mistakes: Raising too early (no traction), raising too much (dilution + distraction), taking bad money (misaligned investors)
How to Apply and Succeed at YC (Dalton Caldwell)
- What YC actually looks for: Founder quality first, idea second. "Do these founders understand their users? Are they building something people want?"
- Application questions that matter most: "What are you building?" (one clear sentence), "Why now?", "What's your traction?"
- Common application mistakes: Vague descriptions / overselling the market / no traction or fake traction / unclear why these founders
- The YC interview: 10 minutes, fast-paced, about your business. Not a pitch — a conversation. Expect hard questions about your weakest assumptions.
- When to apply: Apply even before you feel ready. YC invests in people who can figure it out.
- What YC provides: $500K, access to alumni network, YC brand, Demo Day — the network compounds over decades
Output Format
Part 1: Module Content
- The fundraising journey stages and when to move between them
- SAFE mechanics explained with a concrete conversion example
- YC application success factors and the questions that matter most
- The fundraising process: managing parallel conversations
Part 2: Apply to Your Situation
- Fundraising readiness: where are you in the journey and what's the next milestone?
- YC application fit: traction, one-sentence description, why these founders?
- Cap table and legal hygiene: IP assigned, incorporation clean, vesting in place?
- SAFE vs. priced round decision for current stage
Part 3: Interactive Workbook (AskUserQuestion)
- Ask questions ONE AT A TIME — do not list all questions at once
- Use AskUserQuestion tool for each question
- After each answer, give 1-2 sentence feedback connecting to the module's framework
- Provide multiple choice options where appropriate to make it easier to answer
- After completing all questions, generate a synthesis:
- Overall readiness score (1-10) for this module's topic
- Top strength identified from answers
- Top gap identified from answers
- One specific action item
- Save completed workbook to
knowledge/yc-startup-school/module-7-workbook.md
Questions to ask interactively:
- What is your one-sentence company description — would it make sense to a YC partner in 10 seconds?
- What is your current growth rate, and what traction can you show to back it up?
- Why now? What changed in the world that makes this the right moment?
- What stage of funding are you at, and what milestone will you hit before your next raise?
- Do you understand your cap table? Can you explain it simply?
- Have you decided between SAFE and priced round? What drove that decision?
- Who are your target investors and how will you get warm introductions?
- Have you assigned IP to your company? Is your incorporation paperwork clean?
- If applying to YC: what is the weakest part of your application right now?
Bonus Content
The bonus folder contains a foundational legal vocabulary lecture relevant to this module:
${CLAUDE_PLUGIN_ROOT}/references/bonus/starting-a-company-the-key-terms-you-should-know.md— Cap table, common vs. preferred stock, option pool, term sheet components, key documents
References
${CLAUDE_PLUGIN_ROOT}/skills/yc-7-fundraising-and-company-building/references/how-startup-fundraising-works.md— Brad Flora (YC Partner)${CLAUDE_PLUGIN_ROOT}/skills/yc-7-fundraising-and-company-building/references/how-to-apply-and-succeed-at-yc.md— Dalton Caldwell (YC Managing Director)