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

There's a difference between education designed to make you knowledgeable about venture capital and education designed to make you effective at deploying capital. Most content serves the first goal. This guide serves the second.

This is venture capital education specifically for people who want to write checks.

The Check-Writer's Mindset

Knowledge serves action. Every concept learned should connect to decisions you'll make. If knowledge doesn't improve decisions, it's entertainment rather than education.

Adequate beats comprehensive. You don't need to know everything. You need to know enough to make intelligent decisions at your check size. Over-education delays investing without improving outcomes.

Practice develops judgment. Reading about investing develops knowledge. Actually investing develops judgment. Judgment matters more than knowledge for long-term success.

Portfolio thinking dominates. Individual deal analysis matters less than overall portfolio strategy. Education should emphasize portfolio construction first, deal selection second.

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."

Check-writers internalize this reality and build strategy around it.

What Check-Writers Must Know

Essential 1: Portfolio Construction (Non-Negotiable) Why 15-20+ investments minimum. Power law return dynamics. Check size consistency. Deployment timeline and pacing. This knowledge shapes every subsequent decision.

Essential 2: Investment Structures (Required) SAFE mechanics and conversion. Valuation cap implications. Reasonable terms by stage. Enough to understand what you're signing, not enough to be lawyer.

Essential 3: Evaluation Calibration (Important) What's evaluable at early stages and what isn't. Appropriate due diligence for $1,000 checks (2-3 hours). Where to focus limited time. How to reach decisions efficiently.

Essential 4: Operational Execution (Necessary) How commitment process works. Document signing basics. Wire transfer logistics. Portfolio tracking setup. Enough to execute without anxiety.

What Check-Writers Can Skip (Initially)

Advanced valuation modeling: Pre-revenue companies can't be valued precisely. Sophisticated models create false confidence. Basic reasonableness assessment is sufficient.

Comprehensive legal knowledge: Communities use standard documents. Focus on key terms (cap, discount). Trust infrastructure to handle complexity.

Deep sector expertise: Valuable eventually but not prerequisite for first investments. General evaluation frameworks work initially.

Tax optimization strategies: Important for portfolio management but not for getting started. Learn later as portfolio develops.

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

The Check-Writer's Curriculum

Week 1-2: Portfolio Construction (10 hours) Power law returns. Failure rate reality. Portfolio size requirements. Check size discipline. Deployment strategy.

Week 3-4: Structures and Terms (8 hours) SAFE mechanics. Valuation caps. Dilution basics. Exit scenarios. Document overview.

Week 5-6: Evaluation Calibration (8 hours) Team assessment essentials. Market sizing basics. Business model viability. Due diligence scoping. Decision frameworks.

Week 7-8: Community and Execution (6 hours) Community selection. Operational preparation. First investment planning. Execution logistics.

Total: 32 hours over 8 weeks. Sufficient for intelligent first investments.

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."

Check-writers prioritize getting to practice rather than extending preparation.

Evaluation for Decision-Making

The check-writer's question: Is this opportunity good enough to include in my portfolio? Not "is this the best opportunity?" but "does this meet my minimum criteria?"

Time-boxed assessment: 2-3 hours maximum for $1,000 investment decisions. More time doesn't improve outcomes proportionally at small check sizes.

Decision criteria clarity: Written criteria before evaluation begins. Does opportunity meet criteria? If yes, invest. If no, pass. Minimize deliberation beyond criteria application.

Conviction irrelevance: Your excitement about specific deals doesn't predict outcomes. Maintain consistent approach regardless of how you feel about particular opportunities.

The Decision Framework

Filter 1: Basic comprehension. Do you understand what company does and why it might succeed? If market or model is incomprehensible, pass.

Filter 2: Team assessment. Does founding team have relevant capability for this specific opportunity? Not general impressiveness but specific relevance.

Filter 3: Terms reasonableness. Are valuation cap and terms within normal ranges for stage? If dramatically outside norms, investigate or pass.

Filter 4: Social proof. Are other experienced investors participating? Not required but useful signal. Lack of other investors is yellow flag.

Decision: Passes all filters? Invest $1,000. Fails any filter? Pass. Don't deliberate beyond filter application.

Building Check-Writing Muscle

First 5 investments: Follow framework mechanically. Don't override with intuition. Build discipline before developing nuanced judgment.

Investments 6-15: Notice patterns in your decisions. Which filters do opportunities commonly fail? Refine criteria based on experience.

Investments 16+: Framework becomes intuitive. Evaluation speeds up naturally. Judgment develops through accumulated pattern recognition.

Common mistake: Abandoning framework when conviction is high. Discipline matters most when you're most excited about a deal.

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

Check-writers maintain open criteria that don't filter based on founder backgrounds matching narrow expectations.

Operational Readiness

Before first investment:

• Tracking spreadsheet created and ready
• Calendar blocks for weekly engagement
• Bank account set up for wire transfers
• Documentation templates prepared
• Community membership active

Execution checklist:

• Indicate commitment through platform
• Review and sign documents (verify your information)
• Execute wire transfer (follow instructions exactly)
• Confirm receipt and completion
• Update tracking immediately

Post-investment routine:

• Read company updates when received
• Note developments in tracking
• Provide help only when asked and relevant
• Maintain patience for 7-10 year outcomes

The Check-Writer's Resources

Primary learning: Community education from active VCs. Angel Squad provides weekly programming from Hustle Fund GPs covering check-writer essentials.

Deal flow: Community provides curated opportunities. Angel Squad sources from Hustle Fund's pipeline of 1,000+ monthly applications.

Execution support: Community infrastructure handles SPV creation, documentation, and administration. Focus on decisions, not logistics.

Peer support: Other check-writers at similar stages. Shared experience and accountability.

Measuring Check-Writer Readiness

You're ready when:

• You can explain portfolio construction rationale in 2 minutes
• You can evaluate opportunity in 2-3 hours using clear criteria
• You understand SAFE terms enough to assess reasonableness
• You have operational systems prepared
• You've set specific first investment deadline

You're not ready when:

• Portfolio construction logic is fuzzy
• Evaluation approach is undefined
• Investment structures confuse you
• No deadline exists for first investment

You're over-prepared when:

• You've been studying for months without investing
• You keep finding new topics to research before starting
• Perfect understanding feels like prerequisite
• First investment deadline keeps moving

The Check-Writer's Path

Weeks 1-8: Complete check-writer curriculum (32 hours) Weeks 9-12: Active observation through community Weeks 13-16: First investment execution Ongoing: Quarterly investment pace building portfolio

Total time to first check: 16 weeks from starting education Total preparation investment: Approximately 50-60 hours

Angel Squad serves check-writers specifically: curriculum-aligned education from Hustle Fund GPs teaches exactly what check-writers need, curated deal flow provides opportunities for applying knowledge immediately, operational infrastructure handles complexity so you focus on decisions, and community of fellow check-writers provides accountability and shared experience.

Education for check-writers is education that produces checks. Learn what you need to decide and deploy. Skip what doesn't serve that goal. Start writing checks.