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

You want to learn angel investing and start quickly. Sixty days from today, you can have first investment complete if you follow this systematic approach.

This is the accelerated path from beginner to active investor.

Days 1-7: Foundation Week

Day 1 (2 hours): Learn what angel investing actually is. Individual capital invested in early-stage startups. Equity ownership. High risk, long timeline. Basic mechanics.

Day 2 (2 hours): Understand why portfolios matter. Power law returns. Most investments fail. Few generate returns. Statistical necessity of diversification.

Day 3 (2 hours): Learn portfolio construction principles. Why 15-20+ investments minimum. Check size consistency. Building over 2-3 years at quarterly pace.

Day 4 (2 hours): Verify your qualification. Accreditation requirements ($200K income or $1M net worth). Review financial documents. Confirm you clearly meet thresholds.

Day 5 (2 hours): Assess capital availability. Do you have $15-20K over 2-3 years to risk? Calculate deployment budget. Confirm this is true surplus.

Day 6 (2 hours): Learn realistic return expectations. What 2-3x portfolio return means. Timeline to exits (7-10 years). What success actually looks like.

Day 7 (1 hour): Week 1 synthesis. Review notes. Write summary of key principles. Confirm you understand portfolio construction rationale.

Week 1 milestone: You understand basic mechanics and have verified qualification and capital availability.

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."

Week 1 establishes why portfolio construction matters before you start building one.

Days 8-14: Structures Week

Day 8 (2 hours): Learn SAFE fundamentals. Simple Agreement for Future Equity. Why it's standard. Basic conversion mechanics.

Day 9 (2 hours): Understand valuation caps. What post-money caps mean. How to calculate ownership. Reasonable ranges by stage.

Day 10 (2 hours): Learn discounts and additional terms. How discounts function. Pro-rata rights. Which terms matter at small check sizes.

Day 11 (2 hours): Understand dilution. How ownership decreases over funding rounds. Setting realistic ownership expectations.

Day 12 (2 hours): Learn exit scenarios. Acquisitions versus IPOs. How proceeds distribute. What different outcomes mean.

Day 13 (2 hours): Review sample term sheets. Read actual SAFE documents. Practice understanding what you're agreeing to.

Day 14 (1 hour): Week 2 synthesis. Create reference document summarizing structures. Confirm you can read and understand basic term sheets.

Week 2 milestone: You understand investment structures and can evaluate whether terms are reasonable.

Days 15-21: Evaluation Week

Day 15 (2 hours): Learn team assessment basics. What to look for in founders. Background indicators. Presentation evaluation.

Day 16 (2 hours): Learn market analysis approaches. TAM, SAM, SOM basics. What market size matters at early stages.

Day 17 (2 hours): Learn business model evaluation. Revenue models. Unit economics basics. Path to profitability assessment.

Day 18 (2 hours): Learn product and traction assessment. Product-market fit signals. Interpreting early metrics.

Day 19 (2 hours): Learn due diligence calibration. Appropriate effort for $1,000 checks (2-3 hours). Where to focus limited time.

Day 20 (2 hours): Develop personal evaluation criteria. Write document capturing what makes opportunity interesting to you.

Day 21 (1 hour): Week 3 synthesis. Review evaluation framework. Confirm you have criteria for assessing opportunities.

Week 3 milestone: You have written evaluation criteria and understand appropriate due diligence approach.

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."

Evaluation framework prepares you for practice reps.

Days 22-28: Community Week

Day 22 (3 hours): Research angel investing communities. Identify 5-7 options. Review websites and offerings.

Day 23 (3 hours): Evaluate communities against criteria. Deal flow quality, educational programming, investment minimums, cost structure, member satisfaction.

Day 24 (2 hours): Talk to current members. Reach out to 2-3 members of communities you're considering. Ask about actual experience.

Day 25 (2 hours): Complete member conversations. Gather perspectives on different communities. Note strengths and concerns.

Day 26 (2 hours): Make community selection. Choose based on research and member feedback. Prepare application materials.

Day 27 (2 hours): Submit application. Provide accreditation verification. Complete profile information. Pay membership fees.

Day 28 (2 hours): Complete onboarding. Watch introductory content. Learn platform navigation. Set up calendar blocks for weekly engagement.

Week 4 milestone: Community joined. Onboarding complete. Ready to begin active observation.

Angel Squad provides ideal structure for this timeline: clear application process, immediate platform access after approval, structured onboarding content, and curated deal flow ready for review.

Days 29-49: Observation Period (3 Weeks)

Weekly routine:

• Review all new opportunities presented (3-4 per week, 90 minutes total)
• Attend educational programming (60-90 minutes)
• Track evaluation thinking in spreadsheet (30 minutes)
• Participate in community discussions (30-60 minutes)

Total weekly time: 4-5 hours

What you're building: Pattern recognition through real opportunity exposure. After 3 weeks, you've reviewed 10-15 actual opportunities and developed genuine perspective.

Active engagement: Don't passively review. For each opportunity, write whether you'd invest and why. Compare your thinking to experienced investor perspectives.

Observation milestone: By Day 49, you've reviewed 10+ opportunities and can articulate what interests you about certain deals.

Days 50-60: First Investment Execution

Days 50-52: Opportunity Selection Identify opportunity meeting your criteria. You understand market basically. Team seems capable. Business model makes sense. Other experienced investors participating. Terms are standard.

Days 53-54: Due Diligence Conduct appropriate diligence (2-3 hours total). Google founders. Research market briefly. Review terms. Check other investors. Confirm nothing concerning.

Day 55: Decision and Documentation Make invest decision. Write 2-3 paragraph thesis explaining why you're investing, main risks, and what success requires.

Day 56: Commitment Indicate $1,000 investment through platform. Submit commitment before deadline.

Days 57-58: Documentation Review and sign documents electronically. SPV agreement, subscription agreement, investment terms. Verify your information is correct.

Days 59-60: Fund Transfer Receive wire instructions. Execute wire transfer. Confirm funds received. Receive investment confirmation.

Day 60 milestone: First angel investment complete. Portfolio construction begun.

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

Your first investment starts your journey of supporting those founders.

The 60-Day Time Investment

Weeks 1-3 (Foundation): 40-45 hours total learning Week 4 (Community): 15-20 hours research and joining Weeks 5-7 (Observation): 12-15 hours active observation Weeks 8-9 (Investment): 6-8 hours execution

Total: 73-88 hours over 60 days (approximately 10-12 hours weekly)

What Makes This Timeline Work

Sufficient foundation: Three weeks of concentrated learning provides adequate knowledge base. Not comprehensive expertise but enough for intelligent decisions.

Real exposure: Three weeks of opportunity observation builds pattern recognition. Seeing actual deals develops judgment faster than additional theory.

Commitment structure: Sixty-day deadline creates urgency. Open-ended learning timelines produce perpetual postponement.

Appropriate stakes: First $1,000 investment is meaningful but not catastrophic. You're learning with real money at appropriate scale.

Common 60-Day Timeline Obstacles

Obstacle: "I want more foundation time." Solution: Three weeks is sufficient. Additional preparation provides diminishing returns. Start observing.

Obstacle: "I haven't found the right opportunity." Solution: Good enough is sufficient for first investment. You're starting portfolio, not picking guaranteed winner.

Obstacle: "I don't feel ready." Solution: You won't feel completely ready. First investment is meant to be uncomfortable. Proceed anyway.

Obstacle: "Life got busy and I fell behind." Solution: Extend timeline to 90 days rather than abandoning. Maintain momentum even if slower.

After Day 60

Days 61-90: Continue observation and education. Plan second investment for within 90 days of first.

Months 4-12: Build toward 6-8 investments in first year. Maintain quarterly pace. Continue educational engagement.

Years 2-3: Complete portfolio construction (15-20 investments). Refine evaluation approach based on experience.

Years 4-10: Portfolio management. Wait for outcomes. Maintain engagement through boring years.

Angel Squad enables this 60-day timeline: structured onboarding gets you started quickly, curated deal flow from Hustle Fund's pipeline provides quality opportunities for observation and investment, weekly education from active VCs supports continued learning, $1,000 minimums make first investment accessible, and community provides accountability for maintaining timeline.

Sixty days from now, you can have your first angel investment complete. Follow the systematic approach. Maintain timeline discipline. Start your portfolio. The learning that matters most happens through actual investing.