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 from now, you could have your first angel investment closed and a clear path forward. Not because you've become an expert, but because you've followed a systematic plan.

Week-by-week breakdown of exactly what to do.

Days 1-7: Foundation and Education

Monday-Tuesday: Understand the Basics

Read introductory content on angel investing. Focus on understanding:

• What angel investors actually do
• How startup funding works
• What returns to realistically expect
• Why most investments fail

Spend 2-3 hours total consuming high-quality content from experienced practitioners. Avoid generic "entrepreneur magazine" type content. Look for specific, tactical guidance from actual angels.

Wednesday-Thursday: Learn Portfolio Theory

This is crucial. Angel investing isn't about picking winners—it's about portfolio construction.

Understand power law returns. Why do VCs obsess about unicorns? How do portfolio size and diversification affect outcomes? What's the minimum number of investments needed for decent odds?

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."

This mindset shift prevents the biggest beginner mistake: putting too much capital into too few companies.

Friday-Sunday: Learn Terminology

Spend 3-4 hours learning angel investing vocabulary:

• SAFEs vs. convertible notes vs. priced rounds
• Pre-money and post-money valuations
• Cap tables and dilution
• Liquidation preferences and pro-rata rights

You don't need expertise. Just basic literacy to follow conversations and understand deal terms.

Days 8-14: Community Research and Selection

Monday-Wednesday: Identify Options

Research 5-7 angel investing communities. Don't just look at websites—dig deeper:

Talk to current members (most communities will connect you). Ask about actual deal volume, educational quality, time commitment, and costs. Request specific examples of recent investments.

Look for communities providing:

• High deal volume (100+ opportunities reviewed monthly)
• Structured education (weekly programming from experienced investors)
• Reasonable minimums ($1,000-2,000)
• Transparent costs
• Active member engagement

Angel Squad, for example, provides access to Hustle Fund's pipeline of 1,000+ monthly applications, weekly educational programming, and community of 2,000+ investors—checking all boxes.

Thursday-Friday: Evaluate Fit

Narrow to 2-3 communities that match your goals and constraints.

Consider:

• Can you afford the membership costs?
• Does the time commitment work with your schedule?
• Do current members seem engaged and helpful?
• Is the educational content at appropriate level?

Saturday-Sunday: Join and Onboard

Make your decision and join. Complete onboarding process. Set up account. Review any initial materials.

Schedule recurring calendar blocks for participating: 3-5 hours weekly distributed across week.

Days 15-30: Observation and Pattern Recognition

Week 3: Pure Observation

Don't invest yet. Just observe.

Review 5-7 new investment opportunities this week. Read pitch decks. Watch any founder presentations. Follow discussions about deals among community members.

You're building initial pattern recognition. What do strong teams look like? Which markets seem interesting? What business models make intuitive sense?

Attend at least one educational session. Take notes. Ask questions about anything confusing.

As Eric Bahn, co-founder and GP of Hustle Fund, emphasizes: "Investing requires practice like everything else. So you have to see a lot and invest a lot to get better."

This observation period is essential practice.

Week 4: Active Evaluation

Continue reviewing new opportunities, but now develop opinions.

For each company: Would you invest or not? Why? What excites you or concerns you? What questions would you ask the founders?

Document your thinking. You're building evaluation frameworks even though you're not investing yet.

Compare your initial reactions to how experienced investors evaluate same companies. What do they see that you missed? What concerns them that didn't worry you?

Days 31-45: Framework Development

Week 5: Build Your Investment Thesis

Start developing loose investment thesis. What types of companies interest you most?

This doesn't need to be restrictive. But having some focus helps:

• B2B SaaS? Consumer products? Infrastructure?
• Pre-seed? Seed? Both?
• Specific industries you understand?

Your thesis will evolve, but starting with some framework prevents random decision-making.

Week 6: Deep Dive on One Opportunity

Choose one interesting company from recent weeks. Do lightweight due diligence:

Research the market. Who are competitors? Is the market growing? What do customers say?

Research the founders. Check LinkedIn backgrounds. Google them. What have they built before?

Research the business model. How do they make money? What are unit economics? Does the math work?

You're learning the due diligence process without pressure of actually investing.

Days 46-60: Identifying First Investment

Week 7: Active Deal Hunting

Review 5-7 new opportunities specifically looking for first investment candidate.

What makes a good first investment?

• You understand the market
• You believe in the founding team
• The business model makes basic sense
• Other investors you respect are participating

Don't look for perfection. Good enough is sufficient for a learning investment.

Week 8: Selection and Initial Diligence

Select your first investment candidate. Spend this week doing basic due diligence:

Talk to the founders if possible. Attend any office hours or Q&A sessions. Ask about traction, burn rate, and specific plans.

Check who else is investing. Are experienced angels participating? That's a good signal.

Review the terms. Do you understand what you're getting? Are terms standard for the stage?

Days 61-75: Pre-Investment Preparation

Week 9: Document Your Thinking

Before committing, write down your investment thesis for this company:

Why are you investing? What do you expect to happen? What are the main risks? What would success look like?

This documentation is crucial for future learning. Six months from now, you'll review whether your thinking was correct.

Week 10: Final Decision and Setup

Make your final decision. Commit to investing $500-1,000.

Understand the mechanics. If investing through community, they typically handle all paperwork via SPVs. You just commit your amount.

If investing directly, you'll sign a SAFE or other investment document. Read it carefully even if you don't understand every clause.

Set up tracking. Create spreadsheet or use portfolio software to track all investments going forward.

Days 76-90: First Investment and Planning

Week 11: Complete First Investment

Execute the investment. Complete any required paperwork. Confirm everything is finalized.

Congratulations. You're now an angel investor.

Update your tracking immediately with all details: company name, amount, date, terms, your thesis.

Week 12: Plan Next Steps

With first investment complete, plan your next 6-12 months:

How many investments will you make? (Target: 6-10 over next year)

What capital will you deploy? (Target: $8,000-12,000 total)

How will you continue learning? (Maintain 3-5 hours weekly commitment)

Week 13: Reflect and Adjust

Take time to reflect on your first 90 days:

What did you learn? What surprised you? What was easier than expected? What was harder?

Adjust your approach based on learnings. Maybe you need more time for evaluation. Maybe you can move faster. Maybe your investment thesis needs refinement.

Critical Success Factors

Consistency: The 3-5 hours weekly commitment throughout 90 days matters more than sporadic intensity.

Community: Trying to do this solo dramatically slows progress. Community structure provides scaffolding for systematic learning.

Action: The plan requires actual investment at day 76. Many beginners never pull trigger. Commit to following through.

Documentation: Writing down your thinking at each stage creates feedback loops for future improvement.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." Your evaluation frameworks developed over 90 days help you recognize great founders beyond obvious signals.

What Happens After Day 90

You've made your first investment. You have evaluation frameworks. You understand the process. You're part of a community.

Next 6-12 months: Make 5-10 more investments to build actual portfolio. Continue participating in education. Help your portfolio companies where you can.

The 90-day plan gets you started. The next 1-2 years build on that foundation.

Angel Squad's structure aligns perfectly with this 90-day timeline: immediate access to curated deal flow from Hustle Fund's pipeline means you're evaluating real opportunities from day one, weekly educational programming builds your frameworks systematically rather than randomly, community of 2,000+ investors provides examples of others making first investments, and $1,000 minimums mean your first investment is meaningful but not scary. 

The structured approach transforms "I'm interested in angel investing" into "I'm an angel investor with my first deal closed" in three months rather than three years of wandering.

Ninety days is tight but achievable. Follow the plan. Put in the hours. Make the first investment. Everything else builds from there.