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

Can you really go from knowing nothing about angel investing to completing your first investment in thirty days?

Yes, if you commit to it fully. This isn't casual exploration. It's intensive sprint requiring 1-2 hours daily for a month.

Most people should take longer. The 60-90 day timeline is more comfortable. But if you're highly motivated and have time to dedicate, thirty days works.

Days 1-5: Intensive Education Week

Day 1: Understanding the Fundamentals

Spend 2-3 hours understanding what angel investing actually is. You're buying equity in very early-stage companies through SAFEs or convertible notes. Most investments (60-70%) will fail completely. Time horizon is 7-10 years. Returns follow power law distributions where few massive winners carry portfolio.

Read content from actual practitioners: experienced angels and VCs writing about their investment experiences, frameworks they use, and realistic expectations about outcomes. Avoid motivational content or generic startup advice, you need tactical understanding from people who've actually invested.

Day 2: Portfolio Construction Theory

Spend 2-3 hours learning why diversification is non-negotiable at early stages. You need 15-20+ investments minimum because you can't reliably predict which companies succeed. Concentrated bets are gambling. Portfolio approach is only viable strategy.

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." Internalize this before investing a dollar. It shapes every decision going forward.

Study power law returns. Understand why VCs need 100x+ outliers to return funds. See how this math applies to your individual portfolio even at smaller scale.

Day 3: Angel Investing Terminology

Spend 2 hours learning the language: SAFEs vs. convertible notes vs. priced rounds, pre-money and post-money valuations, cap tables and dilution, pro-rata rights, liquidation preferences, and common exit scenarios. You need enough literacy to follow conversations about deals without being lost.

Use online resources efficiently. Don't get lost in rabbit holes. Focus on understanding core concepts well enough to function, not achieving expertise.

Day 4-5: Community Research

Spend 3-4 hours total researching angel investing communities. Identify 5-7 worth evaluating. Look for: high deal volume (100+ opportunities reviewed monthly), structured education (weekly programming from experienced investors), reasonable minimums ($1,000-2,000), transparent costs, and active members.

Request conversations with current members of top 2-3 communities. Ask directly: How much time do you spend weekly? Is deal flow quality high? Is education genuinely helpful? Would you recommend this? What are the downsides?

Make your decision by day 5 end. Join immediately and complete onboarding.

Days 6-10: Rapid Observation and Evaluation

Days 6-8: Intensive Deal Exposure

Spend 1-2 hours daily reviewing new investment opportunities in your community. You should see 10-15 companies in this three-day period. Read every pitch deck. Watch every founder presentation available. Follow all community discussions about deals.

You're not investing yet. You're building rapid pattern recognition about what investors focus on, what questions they ask, and what raises concerns. This compressed exposure accelerates learning that typically takes weeks.

Attend at least two educational sessions in these three days. Take detailed notes. Ask questions actively. You're absorbing frameworks faster than typical pace, embrace the intensity.

Days 9-10: Framework Development Sprint

Spend 2-3 hours over these two days developing initial evaluation framework. Based on 10-15 companies you've seen, what patterns emerge? What makes teams seem strong or weak? Which markets look interesting? What business models make intuitive sense?

Write down your emerging thesis: What types of companies interest you? What can you evaluate well based on your experience? What feels beyond your current competence?

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 ten days provide concentrated practice that enables informed first decision.

Days 11-15: Active Deal Hunting

Days 11-13: Identifying Your Candidate

Review 5-7 new opportunities over these three days, specifically looking for your first investment. You're not waiting for perfect company. You're looking for company where you understand market, believe in founders, think business model makes sense, and terms are standard.

Narrow to 2-3 candidates by day 13 end. These should be companies you're genuinely interested in, not settling for mediocre options. But don't wait for obvious unicorn either.

Days 14-15: Initial Due Diligence

Pick your top candidate. Spend 3-4 hours over these two days on due diligence: Google founders thoroughly, check for any red flags or concerning patterns. Verify LinkedIn backgrounds match what they claim. Research market quickly, read industry reports, understand competition and growth dynamics.

Talk to founders if possible. Attend pitch calls or office hours. Ask about traction, burn rate, and capital plans. You're assessing whether they seem honest, thoughtful, and capable of learning.

This is lightweight diligence appropriate for $1,000 investment. You're not conducting institutional-grade analysis. You're verifying basics and checking for obvious problems.

Days 16-20: Decision and Documentation

Days 16-17: Writing Investment Thesis

Spend 2-3 hours writing detailed investment thesis for your chosen company. Why are you investing? What do you expect over next 2-3 years? What are main risks? What would success look like?

This forced articulation clarifies your thinking. If you can't write coherent thesis, you don't understand opportunity well enough. The writing process often reveals gaps in your analysis.

Be honest about weaknesses in your thesis. You're not trying to convince yourself or others. You're documenting your actual thinking for future learning.

Days 18-20: Final Decision Making

Review your thesis. Review the due diligence findings. Consider the risks honestly. Then make decision: invest or pass.

If passing, return to your candidate list and repeat process with second choice. You should be able to evaluate backup option in 1-2 days since you've already developed frameworks.

If investing, commit to it fully. Don't hedge or second-guess endlessly. You've done appropriate diligence for check size. Trust your analysis and move forward.

Days 21-25: Closing Your Investment

Days 21-22: Initiating Investment Process

If investing through community like Angel Squad, indicate your investment amount through platform. The community handles SPV creation and paperwork. You'll need 15-30 minutes to complete required forms and confirm investment details.

If investing directly (less common for first investment), founder sends you SAFE document. Review it carefully. Confirm terms match what was discussed. Sign digitally and prepare wire transfer.

Days 23-25: Finalizing and Documenting

Complete any remaining administrative tasks: wire funds if required, receive confirmation documents, and get copies of all investment paperwork for your records.

Create detailed investment tracking record immediately. Use spreadsheet or portfolio software. Document: company name, date, amount, terms, your thesis, founder contacts, and space for quarterly updates. This tracking system is critical foundation for managing portfolio as it grows.

Update this record quarterly as you receive company updates. You're building database for learning from outcomes over time.

Days 26-30: Reflection and Planning

Days 26-28: Processing Your First Investment

Spend time reflecting on the experience. What was harder than expected? What was easier? What surprised you? What would you do differently for second investment?

Review your decision-making process. Were there points where you hesitated unnecessarily? Were there shortcuts you took that you shouldn't have? This reflection improves your process for future investments.

Recognize that you've accomplished something significant. You went from zero knowledge to active angel investor in one month. Most people never make this leap. You did.

Days 29-30: Planning Your Portfolio Strategy

Map out your next 12 months. You need 15-20 total investments for proper diversification. At $1,000 per investment, that's $15,000-20,000 over 2-3 years. Plan how you'll build toward this goal.

Set quarterly targets: 1-2 investments per quarter feels sustainable. This builds portfolio systematically without rushing decisions or deploying capital too quickly.

Continue attending educational programming weekly. Schedule recurring calendar time for reviewing opportunities. Make community participation routine part of your schedule.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." Your developing frameworks help you recognize great founders as you see more opportunities.

The Thirty-Day Reality Check

This timeline is aggressive. Most people should take 60-90 days for first investment. The thirty-day version requires:

Genuine commitment to 1-2 hours daily without exception. Ability to make decisions quickly with incomplete information. Comfort with compressed learning timeline. $1,000 you can afford to invest immediately.

If you can't commit fully to this pace, extend the timeline. There's no prize for speed. The goal is making informed first investment, not rushing to invest for its own sake.

Why It Works (When Done Right)

The compressed timeline works because you're focused entirely on fundamentals needed for first investment, not comprehensive angel investing education. You learn just enough to make informed $1,000 decision, then continue learning through practice.

The intensive daily commitment creates momentum that prevents procrastination. You don't have time to overthink or get paralyzed by analysis. The pace forces action while maintaining appropriate diligence.

After Day 30

Your first investment is complete, but journey is beginning. Over next 18-24 months, make 10-15 more investments at same pace (1-2 per quarter). Continue educational participation. Help portfolio companies where you can.

The skills you developed in thirty intense days provide foundation for everything else. You compressed what often takes 6-12 months into one focused month. Now you build on that foundation systematically.

Angel Squad's structure enables thirty-day timeline for motivated investors: 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, daily review of opportunities provides concentrated exposure needed for rapid pattern recognition, weekly educational programming compresses learning timeline dramatically, community of 2,000+ investors provides instant peer network and examples, and $1,000 minimums mean first investment is accessible without requiring massive capital or extended saving period.

Thirty days from zero to first check is aggressive but achievable. It requires full commitment and focused effort. For those willing to invest the time, it transforms interest into action in one month rather than one year of indefinite exploration.