Start Angel Investing: Your 90-Day Learning Plan

Brian Nichols is the co-founder of Angel Squad, an angel investing community where aspiring and active angels learn from Hustle Fund’s approach, review curated deal flow, and connect with peers.

Starting angel investing involves unfamiliar terms, incomplete information, and decisions with real financial consequences. A weekly plan gives you a way to learn, find useful peers, and build an evaluation process. Use these 90 days as a learning schedule. Extend any phase when you need more time, and keep investing optional throughout.

Days 1-7: Education Week

Days 1-2: Understand the investment and your limits

Angel investors put their own money into private startups. You might buy shares directly, a security that can convert into shares later, or an interest in a vehicle that holds the investment. Each structure gives you different rights.

Publicly traded stocks have an exchange where buyers and sellers meet. Private startup investments generally have no ready market, less public information, and restrictions on selling.

The US Securities and Exchange Commission (SEC) warns in its private-placement guidance that you could lose your entire investment and may need to hold it indefinitely. A growing business can still leave you waiting for cash.

Before considering a check, write down:

• Affordability: What money could you lose entirely without affecting essential spending, emergency savings, debt obligations, or other financial goals?
• Liquidity: Could you leave that money untouched for years, with no promised date for getting it back?
• Budget: What total limit and per-company limit fit those constraints, after allowing for fees and any capital reserved for later investments?
• Eligibility: Which offerings are available to you under their rules and participation requirements?

In the US, an accredited investor meets specified financial or other qualifying criteria. Accreditation affects access to many private offerings; the SEC’s eligibility guidance explains those criteria and how offering requirements differ. Regulation Crowdfunding also permits non-accredited participation through registered intermediaries, subject to its rules and investment limits.

Joining our community for education doesn't require accreditation. Investing in our relevant offerings does. Membership never obligates you to invest.

Study portfolio construction, meaning how you spread capital across investments. Early-stage outcomes are uneven, and any individual investment can fail.

Our co-founder and general partner Elizabeth Yin wrote in Democratizing Knowledge: “Don't try to pick a co. Select a portfolio.” That perspective makes concentration part of every decision. Diversification still can't guarantee a profit or prevent losses.

Days 3-4: Learn the language

Build a short glossary you can use during deal discussions:

• Simple Agreement for Future Equity (SAFE): A contract with terms for future equity conversion and specified events. It doesn't give you shares immediately, and conversion isn't guaranteed.
• Convertible note: Debt that can convert into equity under its terms. Notes typically carry interest and a maturity date, though terms vary.
• Pre-money and post-money valuation: The company's value before and after new investment in a priced round. A SAFE's valuation cap is a conversion term, not a current market price.
• Capitalization table, or cap table: A record of company ownership and securities. Dilution is a reduction in your ownership percentage when additional shares are issued.
• Pro-rata rights: Contractual rights to participate in future financing to help maintain ownership, subject to their conditions.
• Liquidation preferences: Terms that affect how proceeds are distributed among shareholders when specified events occur.

Aim to follow the conversation and identify what you don't understand. One week of vocabulary study won't make you an expert.

Days 5-7: Compare learning communities

Create a comparison sheet for communities that fit your goals. Include education format, access to founder discussions and deal materials, investment minimums, costs, transparency, and member engagement.

Separate the learning experience from the investment opportunity. A minimum check size says nothing about whether a deal is affordable for you, whether you'll receive an allocation, or whether it deserves your money.

Days 8-14: Community Selection Week

Days 8-10: Interview current members

Request conversations with members of the communities you're considering. Ask:

• How much time do you spend, and which activities are useful?
• What does a typical deal review include? What information remains unavailable?
• Which educational sessions have changed how you evaluate a company?
• Can beginners ask basic questions and participate without investing?
• What costs, frustrations, or downsides surprised you?
• Would you recommend the community to someone with my goals and experience?

Take detailed notes. Specific examples from members are more useful than a general endorsement.

Days 11-12: Choose a learning environment

Compare what members described with your goals, available time, and budget. Look for understandable education, candid discussion of risks, transparent costs and terms, and enough relevant opportunities to practice evaluating businesses.

A paid community is optional. Public educational resources, local events, and conversations with investors can also support your learning. Choose the environment you'll use consistently, without treating deal volume as a quality score.

Days 13-14: Set up a workable calendar

If you join a community, complete onboarding, review its materials, and introduce yourself. Plan recurring time for education, deal review, and deeper evaluation.

For example, you could reserve Tuesday evening for a session, Wednesday morning for notes, and Saturday morning for research. Adjust those blocks to your life. Diligence can require more time than a calendar slot allows.

Days 15-28: Observation and Framework Development

Week 3: Observe before committing capital

Read pitch decks, watch founder presentations, and join educational discussions without pressure to invest. Notice which questions experienced investors ask about customers, founders, market demand, and terms. Ask basic questions when something is unclear.

Keep a record of the claims that attract you, the evidence behind them, and the unanswered questions. Investor Sandy Naidu's 5T evaluation framework offers one way to organize observations around team, target market, technology, traction, and terms. Your criteria can evolve with experience.

Week 4: Write your opinion before reading others'

For each company you review, write down:

• Would I invest, pass, or wait? Why?
• What excites me, and what concerns me?
• Which statements have supporting evidence?
• What additional information would change my decision?

Then compare your reasoning with experienced investors' reactions. Identify questions you missed and disagreements you can explain. Someone else's confidence doesn't resolve your unanswered questions.

As Elizabeth Yin wrote in Democratizing Knowledge, “Investing requires practice like everything else.” Written evaluations give you a record to revisit before you've risked money. Peer discussions also give you people to learn alongside, including at local gatherings.

Days 29-42: Investment Thesis Development

Week 5: Define your professional edge and its boundaries

Write a one- or two-page investment thesis, a description of the companies you want to consider and why. Use your observations and professional experience:

• Which industries and customer problems do you understand?
• Which business models can you evaluate effectively?
• What evidence would help you assess a founding team's ability to execute?
• Where does your knowledge end, and whose expertise would you need?

For example, a healthcare operator may understand a hospital's purchasing process while needing specialist help to assess a medical device's clinical evidence. Familiarity with a customer doesn't establish competence across the whole business.

Week 6: Apply the thesis to a candidate

Evaluate a new company against that thesis. Explain the customer problem, why the team might solve it, how the business could earn money, and what could derail it. Record the proposed investment structure and the terms you need to understand.

Experienced investors' participation is useful context, but their rights, incentives, and ability to absorb losses may differ from yours. Use your own reasoning. A candidate can move to deeper diligence, your watchlist, or your pass list. There's no requirement to select a first investment this week.

Days 43-56: A Conditional First Investment

Week 7: Review the company, documents, and open questions

Due diligence is the work of investigating the business and the proposed investment. Founder searches and market reports are starting points. The depth required depends on the company, structure, and unresolved risks.

• Company: Compare founders' background claims with available records. Examine customer evidence, competition, financial information, cash needs, and the planned use of the new capital. Ask the founders about gaps or contradictions.
• Security and rights: Obtain the actual SAFE, note, or share-purchase documents, relevant cap-table information, and any side letters. Understand conversion terms, dilution, information rights, transfer restrictions, and how proceeds could reach you.
• Vehicle and costs: If you invest through a special purpose vehicle (SPV), a separate entity pooling investors' capital, review its governing and subscription documents too. Understand what the vehicle owns, who controls decisions, fees, expenses, carried interest, and reporting. Carried interest is a manager's share of investment profits under the agreed terms.
• Unresolved issues: List missing information and the questions that remain. Obtain independent review from qualified legal and tax professionals where needed. A community memo or a lead investor's participation doesn't replace your review.

Write a pre-commitment memo while your reasoning is fresh. State why the company fits your thesis, what progress you expect, the evidence behind those expectations, the main risks, and what would change your view. Include the proposed amount, total cost, and its fit within your limits.

Week 8: Decide whether to invest, pass, or wait

Invest only when you're eligible, the cost fits your loss budget, you understand the documents, and the remaining uncertainty is acceptable to you. Pass when the business, terms, or risks don't fit. Wait when material questions or your own readiness remain unresolved. A closing deadline doesn't fix either problem.

If you proceed, complete the required eligibility process and subscription paperwork, use the platform's authenticated payment instructions, and retain the acceptance and closing confirmation. Paperwork, funding, and acceptance can be separate steps. Expressing interest doesn't guarantee an allocation.

Create a tracking record for every decision:

• Company, review date, and invest/pass/wait status.
• Amount committed, amount funded, fees, and remaining budget, if applicable.
• Security or vehicle, key terms, and saved documents.
• Your thesis, evidence, outstanding questions, and decision rationale.
• Founder or manager contacts and a place for updates and follow-up notes.

Days 57-70: Repeat Evaluation and Revisit Concentration

Week 9: Apply the same process to a new candidate

Review another opportunity, write your initial opinion, investigate the company and terms, and document the decision. Improve the process where the previous review exposed a gap. Continue educational sessions that address those gaps.

If you already invested, compare the candidate with your existing exposure. Two companies can depend on the same customers, technology, or funding conditions. Different company names don't automatically mean different risks.

Week 10: Review your pace and budget

Reconcile commitments, funded amounts, fees, and reserves before considering another check. Keep each proposed investment within your pre-set limits. Enthusiasm about a founder doesn't create additional loss capacity.

You can invest, pass, or defer again. Practicing on another company is useful even when no second or third investment follows.

Days 71-84: Systems and Reflection

Week 11: Improve your records and calendar

Review the system you've used so far. Are you capturing the evidence behind each decision? Can you find the documents? Is your calendar realistic? Adjust the parts that caused missed questions or incomplete records.

Compare your memos, including passed and deferred deals. Look for repeated assumptions, competence gaps, and concentration in similar sectors. If you have investments, consider how future choices could affect the portfolio's risks without committing to additional deployment.

Week 12: Reflect on your judgment

Write down what was harder or easier than expected, what surprised you, and what you'd do differently. Separate the quality of your process from what happened to a company afterward.

A later funding round doesn't prove the original investment was sound or put cash back in your account. A disappointing update can also follow a thoughtful decision. Outcomes remain uncertain, and 12 weeks rarely provides a complete picture. Choose a specific weakness to work on next.

Days 85-90: Planning Year One

Plan the next quarter's learning and evaluation work, then sketch the rest of the year. Include education topics, peer conversations, opportunities to review, and time to support founders where your skills are useful.

Keep learning goals separate from deployment decisions. If you plan to invest, record your remaining loss budget, per-company limit, expected fees, and any reserves for follow-on rounds, meaning later funding rounds. Follow-on participation depends on access, terms, and available capital; it's optional.

Plan how you'll avoid excessive concentration over time. No fixed number of startup checks establishes proper diversification, and you don't need to spend the full budget. If available minimums make sensible sizing impractical for you, continue learning without investing.

What You've Accomplished by Day 90

Assess your work against these outputs:

• Knowledge: You can explain the basic structures, risks, and eligibility requirements, and name the concepts you still need help with.
• Evaluation practice: You have written opinions, questions, and memos to revisit, plus examples of how peers' reasoning differed from yours.
• Documented decisions: You can explain your investments, passes, or decisions to wait. Choosing not to invest is a legitimate result.
• Systems: Your records and calendar support repeatable learning and evaluation.
• Next steps: You have a realistic learning plan and limits for any future deployment.

If an output is missing, return to that phase. Completing the calendar doesn't automatically make you ready to invest.

Common 90-Day Mistakes to Avoid

• Rushing to hit a date: Extend diligence or pass when material issues remain. Day 60 or day 90 has no bearing on a company's suitability.
• Letting research drift: Give open questions an owner and a next action, such as requesting a document or discussing a term with independent counsel. Record a pass when the answer makes the deal unsuitable.
• Escalating check sizes: Set limits before reviewing a pitch. A compelling story shouldn't override your affordability or concentration limits.
• Outsourcing judgment: Use other investors' work as input. Understand the investment you're making and retain your own rationale.
• Abandoning education: Keep addressing the weaknesses your evaluations reveal, whether you've invested or are still observing.

After Day 90

Continue reviewing businesses, discussing decisions with peers, and keeping records. If you've invested, track updates and reporting, and offer relevant help to founders without assuming an operating role you can't sustain.

Apply to Angel Squad to learn from Hustle Fund's approach, discuss curated opportunities with peers, and build your investing process without a requirement to write a check.

This material is for education and does not constitute investment, legal, tax, accounting, or valuation advice. Startup investments are speculative, illiquid, and long-term, with a risk of total loss. Seek independent advice from qualified professionals about your circumstances and the governing investment documents.