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

Ninety days is optimal timeline for starting angel investing. It's long enough to learn fundamentals properly but short enough to maintain momentum and not procrastinate indefinitely.

This isn't casual exploration. It's structured plan requiring 5-8 hours weekly for three months. If you commit to the schedule, you'll be active angel investor with real portfolio by day 90.

The complete 90-day roadmap with specific actions each week.

Days 1-7: Education Week

Days 1-2 (4 hours total): Read comprehensive content about angel investing fundamentals. Focus on portfolio construction theory, power law returns, realistic expectations about failure rates, and 7-10 year timelines. Seek content from actual practitioners, not motivational entrepreneurs.

Key concepts to internalize: You can't pick winners reliably. Most investments (60-70%) return zero. Diversification is non-negotiable. Returns take a decade to materialize. These aren't discouraging facts,they're foundation for proper strategy.

Days 3-4 (3 hours total): Learn angel investing terminology. Study SAFEs versus convertible notes, pre-money and post-money valuations, cap tables and dilution, pro-rata rights, and liquidation preferences. You need basic literacy to follow conversations, not expertise.

Days 5-7 (4 hours total): Research angel investing communities. Identify 7-10 worth evaluating based on deal volume, educational structure, investment minimums, transparency, and member engagement. Create comparison spreadsheet with key factors.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Getting deal flow & education have been the bigger blockers to date" for new investors. Week one research identifies which communities solve these blockers best.

Days 8-14: Community Selection Week

Days 8-10 (5 hours total): Request conversations with current members of top 3-4 communities. Schedule 30-minute calls with 2 members per community. Ask specific questions: actual time commitment, real deal flow quality, whether education is genuinely helpful, frustrations or downsides, whether they'd recommend to others.

Take detailed notes. Current members reveal reality versus marketing claims. They'll tell you if deal volume is overstated, education is superficial, or hidden issues exist.

Days 11-12 (3 hours total): Analyze research and make decision. Which community best matches your goals, constraints, and budget? Consider: sufficient deal volume for building portfolio (10+ opportunities monthly), structured educational programming (weekly sessions), reasonable minimums ($1,000-2,000), transparent costs, and active member engagement.

Days 13-14 (2 hours total): Join selected community and complete onboarding thoroughly. Set up account, review getting-started materials, introduce yourself to other members. Schedule recurring calendar blocks: Tuesday evenings for education (90 minutes), Wednesday mornings for deal review (45 minutes), Saturday mornings for deep evaluation (90 minutes).

Make these calendar blocks non-negotiable recurring appointments for next 90 days minimum.

Days 15-28: Observation and Framework Development

Week 3 (Days 15-21, 6 hours total): Pure observation mode. Review 8-12 investment opportunities without pressure to invest. Read every pitch deck. Watch all founder presentations. Follow community discussions. Attend all educational programming.

You're building initial pattern recognition. What do experienced investors focus on? What questions do they ask? What raises concerns? Take detailed notes on evaluation patterns you observe.

Week 4 (Days 22-28, 7 hours total): Active evaluation practice. Continue reviewing opportunities but now develop your own opinions before seeing others' reactions. For each company, write down: Would I invest? Why or why not? What excites me? What concerns me? What additional information would I want?

Compare your initial reactions to how experienced investors evaluate same companies. What are they seeing that you missed? What concerns them that didn't worry you? These gaps reveal your learning priorities.

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 two weeks provide concentrated practice before risking capital.

Days 29-42: Investment Thesis Development

Week 5 (Days 29-35, 6 hours total): Develop loose investment thesis. Based on 20+ companies you've now seen, what patterns interest you? Consider: industries you understand from professional experience, business models that make intuitive sense, founding team profiles you can evaluate well.

Write initial thesis document (1-2 pages): What types of companies interest you most? What can you evaluate effectively? What's beyond your current competence? This framework prevents random decision-making while remaining flexible.

Week 6 (Days 36-42, 7 hours total): Identify first investment candidate. Review new opportunities specifically looking for potential first investment. Don't wait for perfect company. Look for: market you understand at basic level, founders you believe are capable, business model that makes sense, standard terms, and other experienced investors participating.

The goal is "good enough" for first investment, not perfect opportunity. Your first check is educational capital. Choose something reasonable and move forward.

Days 43-56: First Investment

Week 7 (Days 43-49, 8 hours total): Execute due diligence on your first investment candidate. Spend 3-4 hours on basics: Google founders thoroughly for any red flags. Verify LinkedIn backgrounds match claims. Research market briefly through industry reports. Talk to founders in pitch calls if possible.

Write investment thesis document before committing: Why are you investing? What do you expect over next 2-3 years? What are main risks? What would success look like? This documentation serves two purposes: clarifies your thinking now and creates record for future learning.

Week 8 (Days 50-56, 4 hours total): Make your first investment. Commit to $1,000. If investing through community like Angel Squad, indicate amount through platform (15-30 minutes). Community handles SPV paperwork. You receive confirmation and payment instructions.

Create detailed tracking record immediately: company name, date, amount, terms, your thesis, founder contacts, and space for quarterly updates. Update your budget tracking,you've now deployed $1,000 of your three-year $18,000-25,000 budget.

Recognize you've crossed important threshold. You're no longer aspiring angel investor. You're active angel investor with real portfolio started.

Days 57-70: Second and Third Investments

Week 9 (Days 57-63, 7 hours total): Identify second investment candidate using same process. Review opportunities, develop opinion, execute lightweight due diligence, write thesis. Make second $1,000 investment by end of week.

Two investments doesn't create diversification yet, but you're building toward it. You're also practicing evaluation process twice, which improves your frameworks.

Week 10 (Days 64-70, 7 hours total): Make third investment following established process. By end of week 10, you have three investments totaling $3,000. You've deployed 15-20% of year one budget, which is appropriate pace.

Continue attending all educational programming. Continue reviewing every opportunity even when not investing. This sustained engagement builds pattern recognition faster than sporadic participation.

Days 71-84: Systems and Reflection

Week 11 (Days 71-77, 6 hours total): Refine your tracking systems and processes. Are you capturing information you need? Is your calendar working? Are you spending time efficiently? Make adjustments based on first 10 weeks' experience.

Review your three investment theses. What commonalities exist? What differences? Are you diversifying appropriately or concentrating in similar areas? Plan how next investments will maintain or improve diversification.

Week 12 (Days 78-84, 7 hours total): Consider fourth investment if suitable opportunity exists, but don't force it. Four investments in 90 days is solid pace. Three is fine too,quality matters more than hitting arbitrary number.

Reflect on entire 90-day experience. What was harder than expected? What was easier? What surprised you? What would you do differently? This reflection improves your process going forward.

Days 85-90: Planning Year One

Final Week (6 hours total): Map out your next 9 months. You've made 3-4 investments in first 90 days. To reach 8-10 investments by year end, you need 4-6 more over remaining 9 months. That's roughly one every 6-8 weeks, which is sustainable pace.

Set quarterly targets: Q2: make 1-2 more investments. Q3: make 1-2 more. Q4: make 1-2 more. This builds toward 8-10 total by year end while maintaining learning time between decisions.

Plan your year two and three deployment similarly. Year two: 6-8 investments at $1,000 each ($6,000-8,000). Year three: 7-10 investments ($7,000-10,000). By end of year three, you'll have 20-28 total investments,proper portfolio diversification.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." Your developing frameworks over 90 days position you to recognize great founders as you continue building portfolio.

What You've Accomplished by Day 90

Knowledge Foundation: You understand angel investing fundamentals. You know terminology. You have frameworks for evaluating opportunities. This knowledge isn't deep expertise, but it's sufficient for making informed decisions.

Evaluation Practice: You've seen 40-60 companies over 12 weeks. You've practiced evaluation extensively. You've watched how experienced investors think. Your pattern recognition has started developing.

Active Portfolio Started: You have 3-4 investments totaling $3,000-4,000. You're active angel investor with real skin in game, not someone thinking about angel investing.

Systems Established: You have tracking systems set up. Calendar commitments are scheduled. Workflows are established. You can replicate this process for future investments efficiently.

Clear Path Forward: You know how to continue building portfolio over next 2-3 years. You understand pace of 1-2 investments per quarter. You have plan for reaching 20+ investment diversification.

Common 90-Day Mistakes to Avoid

Moving Too Fast: Don't make all investments in first 30 days. Space them out to allow learning between decisions. Your judgment improves with each investment if you give yourself time to reflect.

Moving Too Slow: Conversely, don't spend entire 90 days researching without investing. Analysis paralysis prevents progress. Make first investment by day 60 maximum.

Increasing Check Sizes: Keep all investments at $1,000 for first year minimum. Don't increase to $2,000 or $3,000 for companies you're more excited about. Consistency matters more than conviction.

Skipping Education: Don't stop attending educational programming after first few weeks. Sustained engagement is how you actually improve over time. Learning compounds through consistent participation.

The 90-Day vs. Longer Timelines

Some people need 120 or 150 days for first investments. That's fine. The 90-day plan is optimal for motivated individuals who can commit required time, but extending timeline is better than rushing.

The key is having structured plan with milestones rather than indefinite exploration. Without timeline, most people research for 12-18 months without ever investing. Ninety days forces action while maintaining appropriate learning.

After Day 90

Your angel investing practice is established but far from complete. Over next 18-24 months, continue making 1-2 investments per quarter. Keep attending educational programming. Help portfolio companies occasionally. Track everything systematically.

By month 30-36, you'll have 20-25 investments representing proper diversification. Some early investments will be showing progress or failure. You're seeing feedback on your decision-making. Your judgment has developed substantially from systematic practice.

Angel Squad's structure enables this 90-day timeline: immediate access to curated deal flow from Hustle Fund's pipeline of 1,000+ monthly applications means you're evaluating real opportunities from day one, weekly educational programming builds frameworks systematically rather than haphazardly, community of 2,000+ investors provides examples of others building portfolios successfully, and $1,000 minimums mean investments are meaningful but affordable. The infrastructure supports going from "interested in angel investing" to "active angel investor with portfolio foundation" in 90 days.

Ninety days from now, you can be active angel investor with 3-5 investments, established systems, and clear path to building proper portfolio. The question is whether you'll commit to the structured timeline or continue thinking about angel investing indefinitely without acting.