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

Sixty days from now, you can complete your first startup investment. Not by rushing or cutting corners, but by following a structured learning plan that builds knowledge systematically.

Most beginners spend 12-18 months "learning about angel investing" without ever investing. They're not actually learning, they're procrastinating.

Sixty days is enough time to develop basic competency and make your first informed decision.

Days 1-7: Understanding Fundamentals

Day 1-2: What Angel Investing Actually Is

Spend 3-4 hours reading high-quality content about angel investing basics.

Focus on understanding:

• What are you buying when you invest? (Equity, SAFEs, convertible notes)
• Why do most investments fail? (Understanding base rates)
• How do returns actually work? (Power law, portfolio theory)
• What's realistic timeline? (7-10 years for exits)

Sources to read: blog posts from experienced angels, VC firm educational content, books by practitioners (not motivational fluff).

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 reality upfront prevents shock later when investments fail.

Day 3-4: Portfolio Construction Theory

This is most important concept to internalize before investing.

You're not picking winners. You're building a portfolio where some massive successes offset many failures.

Read specifically about:

• Power law returns in venture capital
• Why portfolio size matters (15-20 minimum)
• How diversification actually works
• Expected value thinking

This mindset shift—from picking winners to building portfolios—is crucial. Most beginners never make it.

Day 5-7: Learning the Language

Spend 3-4 hours learning angel investing terminology:

SAFEs vs. convertible notes vs. priced rounds. Pre-money and post-money valuations. Cap tables and dilution. Pro-rata rights and follow-on investments. Liquidation preferences and exit scenarios.

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

Days 8-14: Community Research

Day 8-10: Identifying Communities

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

What deal volume do they provide? Who are current members? What's the educational structure? What are the costs? What investment minimums?

Angel Squad, for example, provides access to Hustle Fund's curated pipeline of 1,000+ monthly applications, weekly educational programming, and community of 2,000+ investors with $1,000 minimums.

Create comparison spreadsheet with key factors for each community.

Day 11-12: Talking to Members

Request to speak with current members of 2-3 most promising communities.

Ask specific questions:

• How much time do you actually spend weekly?
• What's the quality of deal flow?
• How helpful is educational programming?
• Would you recommend this community?
• What are downsides or frustrations?

Current member perspective reveals what marketing material doesn't.

Day 13-14: Making Decision and Joining

Select community that best matches your goals and constraints. Join.

Complete onboarding process. Set up account. Review any getting-started materials.

Schedule recurring calendar blocks: 3-5 hours weekly distributed across the week. Make this commitment formal.

Days 15-30: Observation and Learning

Week 3: Pure Observation

Your first week in community, just watch. Don't feel pressure to invest.

Review 3-5 new investment opportunities. Read pitch decks. Watch any founder presentations available. Follow community discussions about deals.

You're starting to build pattern recognition. What do professional investors focus on? What questions do they ask? What concerns them?

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

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."

This observation week is foundational practice.

Week 4: Active Evaluation

Continue reviewing new opportunities, but now develop your own opinions.

For each company, ask yourself:

• Would I invest in this? Why or why not?
• What excites me about this opportunity?
• What concerns me?
• What additional information would I want?

Write down 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 are they seeing that you missed? What concerns them that you didn't notice?

Days 31-45: Framework Development

Week 5: Building Investment Thesis

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

Consider:

• Industries you understand (professional expertise, personal interest, etc.)
• Business models that make sense to you (B2B SaaS, marketplaces, consumer products)
• Founding team profiles you can evaluate well (technical founders, operators, etc.)

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

This doesn't mean restricting to narrow niche. Just having some initial focus areas.

Week 6: Deep Evaluation Practice

Choose 1-2 interesting companies from recent weeks. Practice deeper evaluation:

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

Research the founders. Check LinkedIn backgrounds. Google them for press mentions or prior companies. What have they built before?

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

You're learning due diligence process in low-stakes environment.

Days 46-55: Identifying First Investment

Day 46-50: Active Deal Hunting

Review new opportunities specifically looking for first investment candidate.

Criteria for good first investment:

• You understand the market at basic level
• You believe founders are capable (not necessarily exceptional)
• Business model makes intuitive sense
• Terms are standard
• Other investors you respect are participating

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

Day 51-55: Initial Due Diligence

Once you identify candidate, spend this week on basic due diligence:

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

Verify major claims. If they say they have 50 customers, can you confirm that's roughly accurate? If they claim strong technical team, do LinkedIn backgrounds support this?

Check who else is investing. Are there experienced angels or recognizable investors participating? This is positive signal for first investment.

Review terms carefully. Do you understand what you're actually buying? Are terms standard for stage and market?

Days 56-60: Investment Decision and Closing

Day 56-58: Final Decision

Make your decision. Are you investing or not?

Before committing, write down your investment thesis:

• Why are you investing in this company?
• What do you expect to happen over next 2-3 years?
• What are main risks or concerns?
• What would success look like?

This documentation is crucial. Six months from now, you'll review whether your thinking was correct or misguided.

Day 59-60: Execute Investment

Commit to investing. For most communities, this is straightforward—you indicate your investment amount and they handle paperwork through SPVs.

Confirm everything is finalized. You should receive:

• Confirmation of your investment
• Documentation of terms
• Instructions for payment (if not already made)

Update your tracking immediately. Create entry in spreadsheet with:

• Company name
• Investment date and amount
• Terms (SAFE cap, discount, etc.)
• Your documented thesis
• Next steps for staying updated

What You've Accomplished

Knowledge Foundation

You understand angel investing basics. You know terminology. You have frameworks for evaluating opportunities.

This knowledge isn't deep expertise, but it's sufficient to make informed decisions.

Evaluation Practice

You've seen 15-20 companies over 8 weeks. You've practiced evaluation. You've watched how experienced investors think.

Your pattern recognition has started developing.

First Investment Complete

You've made your first $1,000 investment. You're now an angel investor, not someone thinking about angel investing.

Clear Path Forward

You know your process. You understand what works for you. You can replicate this for future investments.

Common Concerns

"Is 60 days enough to make informed decision?"

For $1,000 first investment, yes. You're not betting the farm. You're starting learning process.

More time won't meaningfully improve your first decision. You need experience, which only comes from actual investing.

"Should I wait to see more companies?"

No. You'll see hundreds more over next 2-3 years. Your first investment is about learning the process.

Waiting doesn't help. Acting does.

"What if I pick wrong company?"

You probably will make imperfect choice. That's expected and fine.

The learning from making the investment and watching what happens is worth more than the $1,000 at risk.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." Your first investment teaches you to recognize founder quality, regardless of whether that specific investment succeeds.

After Day 60

Next Steps

With first investment complete, continue building portfolio:

Month 3-4: Make investments #2-3 Month 5-6: Investments #4-5 Month 7-12: Investments #6-10

By end of year one, you have 10 investments. You're building toward 15-20 investment minimum over 2-3 years.

Maintaining Momentum

The discipline of consistent participation matters more than perfect decision-making.

Continue attending educational programming weekly. Keep reviewing opportunities. Make 1-2 investments per quarter.

This sustained practice is how you actually develop as investor.

Why 60 Days Works

Enough Time to Learn Basics

Two months provides sufficient time to understand fundamentals, join community, and practice evaluation.

Not So Long You Procrastinate

Shorter timeline creates healthy urgency. You can't endlessly research. You must act.

Real Investment, Real Learning

Making actual investment by day 60 means you're learning through practice, not just theory.

The feedback from watching your investment develop over subsequent months teaches you more than any additional preparation time would.

Angel Squad's structure enables this 60-day timeline: from day one, you're seeing curated opportunities from Hustle Fund's professional pipeline of 1,000+ monthly applications, weekly educational programming builds frameworks systematically rather than haphazardly, community of 2,000+ investors provides examples of others making first investments successfully, and $1,000 minimums mean first investment is meaningful but not frightening. 

The infrastructure supports going from "interested in angel investing" to "active angel investor with first deal closed" in 8 weeks.

Sixty days is tight but achievable. Follow the plan. Put in the hours. Make the first investment. Everything compounds from there.