Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Not everything about angel investing deserves equal study time before your first investment. Some topics are essential prerequisites. Others can wait until after you've started investing.

This is the prioritized curriculum covering what actually matters before writing your first check.

The Four Essential Knowledge Areas

Area 1: Portfolio Construction (Most Critical) This must come first because it shapes every subsequent decision. Without portfolio construction understanding, you'll make concentration mistakes, vary check sizes based on conviction, and build inadequate diversification.

Area 2: Investment Structures (Required) Understanding what you're signing prevents agreeing to bad terms and creates confidence during document review. You don't need comprehensive legal knowledge but must understand basic mechanics.

Area 3: Evaluation Frameworks (Important) Having structured approach to assessing opportunities prevents random decision-making. Framework doesn't need to be perfect but must exist.

Area 4: Operational Knowledge (Helpful) Understanding how SPVs work, what documents look like, and how wire transfers happen reduces anxiety during execution. Operational knowledge prevents logistical mistakes.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Most of your investments will return $0. You will lose money. So it's important to have great portfolio construction."

Portfolio construction is first because everything else depends on understanding this reality.

What to Skip Before First Investment

Advanced valuation modeling: Early-stage companies can't be valued precisely. Sophisticated models create false confidence. Basic understanding of reasonable ranges is sufficient.

Comprehensive legal knowledge: You don't need to understand every provision in SPV agreements. Communities use standard templates. Focus on key terms (valuation cap, discount) and trust operational infrastructure.

Sector-specific expertise: You don't need deep domain knowledge to start. General evaluation frameworks work for initial investments. Sector expertise develops through exposure over time.

Tax optimization strategies: Important eventually but not prerequisite for first investment. Tax implications are real but shouldn't delay starting.

Negotiation tactics: At $1,000 check sizes, negotiation is inappropriate and unnecessary. Accept standard terms. Focus on evaluation, not terms modification.

Area 1 Deep Dive: Portfolio Construction (10 Hours)

Concept 1: Power law returns. Small number of investments drive majority of portfolio returns. Understanding this dynamic is fundamental to everything else.

Concept 2: Failure rates. 60-70% of investments return zero. This isn't pessimism, it's statistical reality that portfolio strategy must accommodate.

Concept 3: Portfolio size. 15-20+ investments minimum for adequate diversification. Fewer investments means higher probability of missing the outliers that drive returns.

Concept 4: Check size consistency. Same amount for every investment regardless of conviction. Varying based on excitement produces worse outcomes than discipline.

Concept 5: Deployment timeline. Build portfolio over 2-3 years at quarterly pace. 1-2 investments per quarter. Sustainable rhythm alongside career.

Study method: Read 4-5 substantive articles on each concept. Take notes. Write summary explaining each concept in your own words. Test understanding by explaining to someone else.

Area 2 Deep Dive: Investment Structures (8 Hours)

Topic 1: SAFE mechanics (3 hours). What SAFEs are. How conversion works. Valuation cap implications. Standard terms by stage ($8-15M pre-seed, $15-25M seed).

Topic 2: Dilution math (2 hours). How ownership decreases through subsequent funding rounds. Modeling dilution through Series A and B. Setting realistic ownership expectations.

Topic 3: Exit scenarios (2 hours). Acquisition versus IPO mechanics. How proceeds distribute. What different outcomes mean for your specific investment.

Topic 4: Document overview (1 hour). What SPV agreements look like. What subscription documents contain. What to verify during document review.

Study method: YCombinator SAFE documentation provides excellent foundation. Supplement with blog posts explaining terms practically. Review sample documents to build familiarity.

As Eric Bahn, co-founder and GP of Hustle Fund, emphasizes: "For beginners, a bigger startup portfolio is better. It helps with diversification and helps you learn and get reps in. Investing requires practice like everything else."

Structure knowledge enables confident practice when you start writing checks.

Area 3 Deep Dive: Evaluation Frameworks (8 Hours)

Topic 1: Team assessment (3 hours). What to look for in founders. Background indicators that matter. How to interpret founder presentations and communications.

Topic 2: Market analysis (2 hours). Quick market sizing approaches. What matters at early stages versus what doesn't. How to assess market timing.

Topic 3: Business model basics (2 hours). Revenue model types. Basic unit economics assessment. Path to profitability evaluation.

Topic 4: Due diligence calibration (1 hour). Appropriate effort for $1,000 checks (2-3 hours total). Where to focus limited time. What to verify versus accept.

Study method: Read investor perspectives on evaluation. Note specific criteria they use. Develop personal framework synthesizing approaches that resonate with your thinking.

Critical output: Written evaluation criteria document. Your personal framework for assessing opportunities. Will evolve but having starting point is essential.

Area 4 Deep Dive: Operational Knowledge (4 Hours)

Topic 1: SPV mechanics (1 hour). How Special Purpose Vehicles aggregate investments. Why they exist. How ownership flows through SPV to underlying company.

Topic 2: Document signing process (1 hour). What to expect from electronic signature workflow. How to review documents efficiently. What to verify.

Topic 3: Wire transfer logistics (1 hour). How wire transfers work. What instructions look like. Common mistakes to avoid. Timeline expectations.

Topic 4: Portfolio tracking (1 hour). How to set up tracking spreadsheet. What information to capture. How to maintain records for tax and learning purposes.

Study method: Much of this knowledge comes through community onboarding materials. Angel Squad's structured onboarding covers operational mechanics comprehensively.

The 30-Hour Study Plan

Hours 1-10: Portfolio construction fundamentals. Read, note, synthesize. Create written deployment plan with specific numbers.

Hours 11-18: Investment structures. SAFE mechanics, dilution math, exit scenarios. Review sample documents.

Hours 19-26: Evaluation frameworks. Team, market, business model assessment. Write personal evaluation criteria.

Hours 27-30: Operational knowledge. SPV mechanics, document process, wire logistics, portfolio tracking setup.

Total: 30 hours over 3-4 weeks at 8-10 hours weekly.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere."

Your evaluation framework should reflect this reality, looking beyond traditional profiles.

Study Resources by Area

Portfolio construction: Hustle Fund blog posts. Power law analysis articles. Portfolio math explainers.

Investment structures: YCombinator SAFE documentation. Legal explainer blogs. Term sheet walkthrough articles.

Evaluation frameworks: Investor blog posts on deal assessment. Podcast episodes discussing evaluation approaches. Framework comparison articles.

Operational knowledge: Community onboarding materials. Wire transfer guides. Portfolio tracking templates.

How to Know You've Studied Enough

You're ready when: You can explain portfolio construction rationale clearly. You can read SAFE terms and assess reasonableness. You have written evaluation criteria. You understand basic operational process.

You're not ready when: You can't explain why 15-20+ investments are necessary. Investment structures confuse you. You have no evaluation framework. Operational process is mysterious.

You're over-studying when: You're seeking comprehensive expertise before starting. You're finding increasingly niche topics to research. You've been studying for months without joining community or evaluating real deals.

After Studying: Next Steps

Week 1 post-study: Join community providing deal flow and ongoing education. Angel Squad provides curated opportunities from Hustle Fund's pipeline alongside weekly programming.

Weeks 2-7 post-study: Active observation. Review real opportunities using your framework. Attend educational sessions. Build pattern recognition.

Weeks 8-9 post-study: First investment. Select opportunity meeting your criteria. Execute process. Document thesis.

Ongoing: Continue learning through community engagement, deal evaluation, and portfolio building. Study never completely stops but shifts from foundation to refinement.

Angel Squad supports the transition from study to practice: curated deal flow provides real opportunities for applying your framework, weekly education fills gaps your self-study might have missed, community discussion tests your understanding against experienced perspectives, and operational infrastructure handles complexity so you focus on decisions.

Study the right topics in the right order. Build sufficient foundation. Then start investing. Perfect preparation doesn't exist. Adequate preparation followed by action produces better investors than endless study.