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

Starting something new is always challenging. Startup investing has specific learning curve that's manageable with proper structure. The first 90 days are crucial for building foundation that supports years of successful investing.

This is your structured guide to the first 90 days of startup investing.

Weeks 1-4: Foundation Building

Week 1: Understanding the basics

Days 1-2: Learn what angel investing actually is. Individual capital invested in early stage startups. Equity ownership in exchange for risk capital. High failure rates, long timelines, potential for outsized returns.

Days 3-4: Understand why portfolio construction matters. Power law returns mean most returns come from few investments. Diversification across 20+ investments required to capture outliers.

Days 5-7: Verify your qualification. Accreditation requires $200,000+ income or $1,000,000+ net worth. Review your situation honestly. Confirm you meet requirements clearly.

Week 1 output: Basic understanding of what you're getting into. Qualification confirmed.

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 this matters before you go further.

Week 2: Deepening knowledge

Days 8-10: Learn portfolio construction details. Why 20+ investments minimum. How to pace deployment over 2-3 years. Why consistent check sizes matter.

Days 11-12: Understand realistic return expectations. Median returns are 1.0-1.5x. Top quartile achieves 2.5-4x. Timeline is 7-10 years.

Days 13-14: Assess your financial readiness. Is capital genuinely surplus? Would loss affect lifestyle? Do you have 10-year time horizon?

Week 2 output: Deeper understanding of portfolio approach. Financial readiness confirmed.

Week 3: Learning investment structures

Days 15-17: Learn how SAFEs work. Simple Agreement for Future Equity. Conversion mechanics. Why SAFEs are standard for early stage.

Days 18-19: Understand valuation caps. What post-money caps mean. How to calculate ownership. Reasonable ranges by stage.

Days 20-21: Learn basic dilution concepts. How ownership decreases over funding rounds. Setting realistic expectations.

Week 3 output: Sufficient structural knowledge to understand term sheets.

Week 4: Developing evaluation framework

Days 22-24: Learn team evaluation basics. What to look for in founders. Capability indicators versus credential signals.

Days 25-26: Understand market assessment. Quick sizing approaches. What matters at early stage versus what doesn't.

Days 27-28: Develop personal evaluation criteria. What makes opportunity interesting to you? Write it down.

Week 4 output: Personal evaluation criteria document. Foundation complete.

Weeks 5-8: Community Joining and Observation

Week 5: Research and selection

Days 29-31: Research angel investing communities. Identify 3-5 options. Review deal sourcing quality, educational offerings, costs.

Days 32-35: Talk to current members. Reach out to 2-3 members of communities you're considering. Ask about actual experience.

Week 5 output: Community options evaluated. Clear preference identified.

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."

Community selection enables the consistent practice that success requires.

Week 6: Joining and onboarding

Days 36-38: Complete community application. Provide accreditation verification. Pay membership fees.

Days 39-42: Complete onboarding. Watch introductory content. Learn platform navigation. Understand community processes.

Week 6 output: Community membership active. Platform familiarity established.

Week 7-8: Active observation

Days 43-56: Review every opportunity presented without investing yet. Practice applying your evaluation framework. Note your reactions and questions.

Engagement: Attend educational programming. Participate in community discussions. Ask questions.

Documentation: For each opportunity, write brief assessment: would you invest and why? Track your thinking.

Week 7-8 output: 6-10 opportunities reviewed. Pattern recognition beginning. Community rhythm established.

Weeks 9-12: First Investment Execution

Week 9: Continued observation and preparation

Days 57-63: Continue reviewing opportunities. Your criteria sharpening. Confidence building. Looking for opportunity that fits your framework.

Preparation: Ensure banking is ready for wire transfer. Confirm calendar has time for investment process.

Week 9 output: Criteria refined. Operationally ready for investment.

Week 10-11: Investment selection and commitment

Identify opportunity: Select deal meeting your criteria. Team seems capable. Market makes sense. Terms are reasonable. Other investors participating.

Due diligence: Conduct appropriate diligence for $1,000 check (2-3 hours). Research founders briefly. Understand market basics. Confirm terms are standard.

Commit: Indicate your $1,000 investment commitment through community platform.

Week 10-11 output: Investment selected and committed.

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 backing founders across diverse backgrounds.

Week 12: Investment execution

Documentation: Review and sign SPV subscription documents. Verify your information is correct.

Fund transfer: Execute wire transfer following provided instructions. Confirm funds received.

Confirmation: Receive investment confirmation. Add to your tracking spreadsheet.

Reflection: Write brief thesis documenting why you invested. What excited you? What are main risks?

Week 12 output: First investment complete. You're now angel investor.

Day 90 Assessment

What you've accomplished:

• Built foundational knowledge across portfolio construction, structures, and evaluation
• Joined community providing deal flow and ongoing education
• Observed 10+ real opportunities
• Made first $1,000 investment
• Established tracking and documentation systems

Where you stand:

• Foundation established for long-term practice
• Portfolio started (1 investment of eventual 20+)
• Learning continues through community engagement
• Rhythm established for ongoing investment activity

What comes next:

• Continue quarterly investment pace (1-2 investments per quarter)
• Maintain educational engagement
• Build portfolio over next 2-3 years
• Wait patiently for outcomes (7-10 years)

Keys to Successful First 90 Days

Don't rush: Follow the timeline. Foundation building matters. Skipping to investment without preparation produces poor outcomes.

Don't delay: Follow the timeline. Extended preparation is procrastination. 90 days is sufficient for genuine readiness.

Engage fully: Community membership only works with active participation. Attend programming. Review opportunities. Participate in discussions.

Document everything: Notes on what you learn. Assessment of each opportunity. Thesis for each investment. Create feedback loop for improvement.

Maintain perspective: First investment is beginning, not culmination. 90 days starts the journey that continues for years.

Angel Squad supports successful first 90 days: curated deal flow from Hustle Fund's pipeline provides quality opportunities for observation and investment, weekly educational programming from active VCs builds knowledge, community of 2,000+ members offers peer support, and $1,000 minimums make first investment accessible.

Your first 90 days establish foundation. Follow this guide to transition from complete beginner to active investor with proper preparation.