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

Most guides explain what angel investing is but skip the practical mechanics of actually writing your first check. You need clear operational instructions for the entire process.

Here’s the step-by-step guide to executing your first angel investment.

Before Your First Check: Prerequisites

You've verified accreditation status and have $15,000-20,000 risk capital available. You've joined quality community providing curated deal flow. You've spent 6-8 weeks observing opportunities and learning fundamentals. You're ready to make first investment.

Mental preparation matters here. Your first check will feel significant even though amount is small. This is normal. You're transitioning from aspiring angel to actual investor with real capital deployed.

Set realistic expectations from the start. First investment probably won't be your best decision because you're still learning evaluation. That's fine. The goal is starting portfolio building process, not hitting home run immediately.

Step 1: Identify Your First Opportunity

Review current opportunities available through your community. You're looking for company where you understand market at basic level, founding team seems capable based on backgrounds, business model makes fundamental sense, other experienced investors are participating, and terms appear standard for stage.

Don't wait for perfect opportunity. Good enough is sufficient for first investment. Perfectionism prevents progress and keeps beginners stuck in observation mode indefinitely.

Attend pitch presentation if available. Most opportunities include founder pitch call (30-45 minutes). Attend live or watch recording. This gives you sense of team communication style and how they think about their business.

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."

Your first investment starts that portfolio construction even though outcome is uncertain.

Step 2: Conduct Appropriate Due Diligence

For $1,000 investment, appropriate diligence is 2-3 hours total. More time doesn't proportionally improve outcomes at small check sizes. The opportunity cost of your time exceeds marginal benefit of additional research.

Google the founders for 30 minutes. Verify backgrounds match what pitch deck claims. Check LinkedIn profiles. Look for red flags like fraud history or multiple failed startups with concerning patterns. You're doing basic verification, not comprehensive background checks.

Research market briefly for 30-45 minutes. Is market actually large and growing? Are there similar companies and what happened to them? You need basic market literacy, not exhaustive analysis.

Review terms for 30 minutes. Is valuation cap reasonable for stage (typically $8-15 million for pre-seed, $15-25 million for seed)? Is discount standard if offered? Are there unusual terms that concern you?

Step 3: Make Your Decision

Decision framework is simple. Does opportunity meet your basic criteria? Does anything concern you enough to pass? If answers are yes and no respectively, decide to invest.

Don't overthink this step. You can't predict outcomes with confidence at early stages. You're making educated guess based on limited information. That's normal for early-stage investing and even professionals get it wrong most of the time.

Document your thesis before committing. Write 2-3 paragraphs explaining why you're investing. What excites you about opportunity? What are main risks? What does success require? This documentation enables learning from outcomes later.

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."

Your decision starts that practice with real capital at stake.

Step 4: Execute Your Commitment

Log into community platform and navigate to opportunity. Look for investment indication section and enter amount: $1,000 (your standard check size for first 20 investments).

Commitment deadline matters. Most opportunities have deadline of 1-2 weeks. Your commitment needs to happen before deadline for deal to proceed. Mark it on your calendar.

Deals usually have minimum total raise threshold like $15,000-20,000. If minimum isn't reached, deal doesn't proceed and your commitment is canceled. If minimum is exceeded, deal moves forward to closing.

After indicating, you receive email confirming commitment. This confirms you're in for $1,000 pending final closing. Save this confirmation for your records.

Step 5: Review and Sign Documents

Community creates Special Purpose Vehicle for this investment. SPV aggregates all investor commitments into single investment to company. This structure handles complexity you'd struggle with independently.

Documents you'll receive include SPV operating agreement defining your ownership and relationship with other investors, subscription agreement confirming your $1,000 commitment with representations about accreditation status, and investment terms showing SAFE specifics like valuation cap and discount.

Document review takes 30-60 minutes. Read through everything. They look intimidating but communities use standard templates. Key things to verify: your investment amount is correct, your contact information is accurate, and terms match what was presented.

Electronic signature happens through DocuSign or similar platform. Review each page, sign electronically, and submit. Confirmation email arrives showing documents are complete.

Step 6: Transfer Funds

After document signing, you receive wire instructions including bank name and address, account number, routing number, and reference information with your name and deal identifier.

Wire deadline is typically 1-2 weeks from receiving instructions. Mark deadline on calendar and plan transfer several days early to avoid last-minute problems. Banks sometimes have delays.

Contact your bank to initiate wire transfer. Provide instructions exactly as written and double-check all numbers. Many banks charge wire fee of $25-35. Confirm fee in advance so it doesn't surprise you.

Bank provides confirmation number when wire completes. Save this. You'll receive email from community confirming they received your funds within 1-2 business days.

Step 7: Investment Confirmation

After SPV receives all committed funds, SPV transfers aggregate amount to company. Company issues SAFE or other instrument to SPV representing everyone's investment. Your ownership is now official.

Final confirmation email includes deal summary, your investment amount, number of investors in SPV, total SPV investment, and next steps for portfolio tracking. This is your official record of the investment.

Immediately update your portfolio spreadsheet. Include company name, investment date, amount, terms, investment thesis, and founder contact information if available. This tracking discipline pays dividends for years.

Emotional moment worth acknowledging: You've completed first angel investment. Capital is deployed. You're officially angel investor with portfolio started. This milestone matters regardless of amount.

What Happens Next

Company updates arrive quarterly if you're lucky. Founders send updates to investors and community forwards these to SPV investors. Read updates and note progress or concerns in your tracking.

Your involvement should be minimal but responsive. If founder reaches out with specific questions, respond helpfully. Offer assistance where you have expertise. Don't be demanding or expect frequent engagement since you're peripheral investor with small stake.

Patience is now required. Nothing exciting happens for years typically. Company builds, potentially succeeds or fails, and eventually exits or shuts down. You wait 7-10 years for outcome.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere."

Your first check starts your journey of supporting those founders and learning to recognize great ones over time.

Common First Check Mistakes

Overthinking decision by spending 20+ hours on due diligence for $1,000 investment. Appropriate diligence is 2-3 hours. More time doesn't improve outcomes proportionally at this check size.

Delaying unnecessarily by waiting for perfect opportunity instead of investing in good enough company. First investment doesn't need to be best decision. It needs to start portfolio.

Stopping after one investment then waiting to see outcome before investing again. Portfolio requires 15-20 investments minimum. Keep deploying capital quarterly regardless of early results.

Timeline Summary

Week 1: Identify opportunity and attend pitch. Week 1-2: Conduct due diligence (2-3 hours). Week 2: Make decision and indicate commitment. Week 3: Review and sign documents. Week 3-4: Transfer funds. Week 4: Receive confirmation.

Total elapsed time is 3-4 weeks from identifying opportunity to completed investment. Total time invested is approximately 4-5 hours including evaluation, documentation, and execution.

Angel Squad simplifies first check execution: professionally curated opportunities from Hustle Fund's pipeline ensure quality deals, standard SPV documentation means no surprises, electronic workflow makes signing efficient, clear wire instructions prevent confusion, and confirmation process provides certainty that everything completed properly.

Writing your first check transforms you from aspiring investor to active participant. Follow process systematically, maintain reasonable expectations, and continue building portfolio with subsequent investments.