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

Most angel investing content assumes baseline knowledge. Complete beginners need roadmap starting from absolute zero and progressing systematically to first investment.

The step-by-step journey from knowing nothing to deploying your first $1,000.

Starting Point: Absolute Zero

You've heard about angel investing. Maybe you read article or heard podcast. You're curious whether you could participate. You don't know what SAFEs are, how valuations work, or what realistic outcomes look like.

This is normal starting point. Everyone begins here. The question is whether you can progress from curiosity to qualification to actual investment.

Timeline expectation from the start: From zero knowledge to first investment typically takes 3-4 months if you move systematically. This includes learning, verification, community joining, and observation. Don't try to rush it.

Phase 1: Basic Understanding (Week 1)

Learn what angel investing actually is: Individual investing personal capital in very early-stage companies in exchange for equity ownership. You buy small ownership stakes. If companies become valuable, stakes become valuable. If companies fail (most do), stakes become worthless.

Understand portfolio approach is mandatory. Angel investing requires 15-30 investments over 2-4 years, not 2-3 concentrated bets. High failure rates (60-70%) mean diversification is non-negotiable.

Grasp realistic outcomes early. Successful portfolios return 2-3x over 10 years. $20,000 invested becomes $40,000-60,000 after decade. Not life-changing wealth but decent outcome if you value learning and networks alongside money.

Know the timeline is long. 7-10 years from investment to meaningful exits. This isn't quick money. It's patient capital committed for decade.

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."

Understanding this harsh reality upfront is crucial before proceeding further.

Phase 2: Requirements Verification (Week 2)

Check accreditation status honestly. Do you earn $200,000+ individually ($300,000+ jointly) for past two years? OR is your net worth over $1,000,000 excluding primary residence?

Calculate net worth properly. Add retirement accounts, investment accounts, home equity excluding primary residence, other real estate, business value, savings. Subtract debts excluding primary mortgage. Does result exceed $1,000,000?

Income verification is straightforward. Review last two years' tax returns. Does income clearly meet threshold? Do you have reasonable expectation this continues?

If you don't meet requirements, stop here. Focus on reaching qualification over next 2-4 years through career advancement or asset accumulation. Use waiting time to learn. Return when qualified.

Phase 3: Capital Assessment (Week 2)

Determine risk capital availability honestly. Do you have $15,000-20,000 over next 2-3 years that you could lose completely without affecting lifestyle?

The honest test matters. If all angel investments returned zero tomorrow, would your life change materially? Would you delay major purchase, stress about money, or regret allocation? If yes, you don't actually have risk capital available.

Calculate deployment schedule. $6,000-8,000 annually for three years. Where does this come from in your budget? After all obligations (mortgage, retirement, emergency fund, family), do you have $700 monthly surplus?

If capital isn't clearly available, address this before proceeding. Build savings, reduce obligations, or wait until financial situation improves.

Phase 4: Systematic Learning (Weeks 3-5)

Invest 20-30 hours learning fundamentals before making any commitments. This foundation prevents costly beginner mistakes.

Week 3 focus covers portfolio construction theory, power law returns, realistic failure rates, expected timelines, and realistic return expectations. This conceptual foundation prevents unrealistic expectations later.

Week 4 focus covers investment structures (SAFEs and convertible notes), valuation mechanics (post-money caps and discounts), dilution concepts, and exit scenarios. This operational knowledge helps you understand deal terms.

Week 5 focus covers evaluation frameworks for teams and markets, appropriate due diligence for small checks, and how community operations work. This practical knowledge prepares you for actual investing.

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."

These weeks of learning prepare you for that practice.

Phase 5: Community Research (Week 6)

Identify 5-7 potential communities and research each systematically. This decision determines whether you sustain practice or quit within years.

Evaluation criteria include deal volume (10+ opportunities monthly), deal quality (institutional screening), educational programming (weekly sessions from experienced investors), investment minimums ($1,000-2,000), cost transparency (clear fees and carry), and member satisfaction.

Research actions required: Review websites thoroughly, attend information sessions, request conversations with 2-3 current members per community.

Questions for current members: What's actual weekly time commitment? Is deal flow quality consistently good? Is education genuinely helpful or superficial? What frustrations exist? Would you recommend to colleagues?

Phase 6: Joining and Onboarding (Week 7)

Select best-fit community and complete membership process thoroughly. Don't rush this step.

Application requires providing accreditation verification (tax documents or financial statements), completing profile information, and paying membership fees if applicable.

Onboarding execution means watching all introductory content, reading getting started materials completely, learning platform navigation, and understanding how to review opportunities and indicate investments.

Calendar scheduling is crucial. Set recurring blocks for angel investing activities. Tuesday evenings for education, Wednesday mornings for deal review, Saturday mornings for deep evaluation. Make these non-negotiable appointments.

Phase 7: Observation Period (Weeks 8-15)

Spend 6-8 weeks observing without investing. This patience prevents deploying capital before you develop judgment.

Weekly routine: Review 2-3 new opportunities (90 minutes), attend educational programming (60-90 minutes), track your thinking about each opportunity in spreadsheet.

What you're learning: What makes opportunity interesting versus mediocre, what experienced investors focus on, what questions are most important, how to evaluate quickly and efficiently.

Build decision framework during this period. After seeing 30-40 opportunities, develop criteria. What are your must-haves? What are automatic disqualifiers? What types of opportunities interest you most?

Resist impatience throughout. Observation period feels slow. You want to get started. Maintain discipline. Your first actual investment will be better because of this preparation.

Phase 8: First Investment (Week 16)

Select opportunity meeting your criteria. Good enough is sufficient. Don't wait for perfect deal that may never come.

Selection criteria: You understand market basically, team seems capable, business model makes sense, other experienced investors participating, terms appear standard.

Execution: Indicate $1,000 investment through platform, review and sign documents electronically (30-60 minutes), wire funds according to instructions, receive confirmation.

Document thesis before investing. Write 2-3 paragraphs explaining why you invested. What excites you? What are risks? What does success require? This enables learning later.

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.

Phase 9: Portfolio Building Continuation

Make second investment within next quarter. Maintain 1-2 investments quarterly pace. Build toward 15-20 total investments over 2-3 years.

Consistency matters more than speed. Use same $1,000 amount for investments 2-20. Maintain systematic approach even as process becomes routine.

Continue learning throughout. Attend educational programming, review all opportunities, help portfolio companies occasionally where you have expertise.

Track everything meticulously. Update spreadsheet when each investment closes. Document theses. Note outcomes as they develop over years.

Complete Timeline Summary

Week 1: Learn basic concepts. Week 2: Verify requirements and assess capital. Weeks 3-5: Systematic learning (20-30 hours total). Week 6: Research and compare communities. Week 7: Join and complete onboarding. Weeks 8-15: Observe without investing. Week 16: Execute first investment. Months 5-36: Build portfolio to 15-20 investments.

Total time from zero to first investment: 16 weeks (4 months). Total time to proper portfolio: 2-3 years. Total time to outcomes: 7-10 years.

Angel Squad enables beginner progression: clear requirements prevent unqualified participation, educational resources support systematic learning, transparent operations facilitate community evaluation, observation period through platform access builds judgment, and curated opportunities from Hustle Fund's pipeline provide quality first investment options.

The journey from zero to first investment is achievable in 3-4 months through systematic progression. Don't skip phases. Build foundation properly.