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 people overestimate how long it takes to start angel investing and underestimate how long results take. Getting both timelines right prevents false expectations.

Here’s the realistic timeline from curiosity to outcomes, phase by phase.

Timeline Myth vs. Reality

Common belief holds that angel investing takes years of preparation and network building before you can make first investment. Then exits supposedly happen within 2-3 years.

Actual reality is different. You can make first investment within 3-4 months of starting from zero. But meaningful exits take 7-10 years from investment.

The timeline paradox: Getting started is much faster than expected. Getting results is much slower than expected. Understanding both prevents disappointment and premature abandonment.

Phase 1: Learning and Verification (4-6 Weeks)

Week 1 covers learning basic concepts. What is angel investing? How does it work? What are realistic outcomes? This fundamental understanding takes 5-10 hours of reading and video watching.

Week 2 handles verifying requirements. Check accreditation status ($200,000 income or $1,000,000 net worth). Assess whether you have $15,000-20,000 risk capital available. This verification takes 2-3 hours of reviewing financial documents.

Weeks 3-6 involve systematic learning. Invest 20-30 hours total learning portfolio construction, investment structures, evaluation frameworks, and community operations. This is 5-8 hours weekly over 3-4 weeks.

Total time is 4-6 weeks from absolute zero to ready for community selection. Many people expect this takes 6-12 months. It doesn't if you're systematic.

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."

Learning this fundamental truth takes weeks, not months.

Phase 2: Community Selection and Joining (1-2 Weeks)

Week 1 involves researching 5-7 communities. Review websites, attend information sessions, talk to 2-3 current members per community. This takes 8-12 hours total spread over week.

Week 2 handles selecting best-fit community and completing onboarding. Submit application, provide accreditation verification, complete profile, pay fees, watch introductory content. This takes 4-6 hours total.

Total time is 1-2 weeks from starting research to being active community member. People often overthink this decision and spend months deliberating. That's unnecessary if you evaluate systematically.

Phase 3: Observation Before Investing (6-8 Weeks)

This is phase people want to skip. Don't. Observation period is crucial for developing judgment before deploying real capital.

Weekly activities include reviewing 2-3 opportunities (90 minutes), attending educational programming (60-90 minutes), and tracking thinking in spreadsheet (30 minutes). Total commitment is 3-4 hours weekly.

What you're accomplishing matters. After 6-8 weeks, you've reviewed 40-60 opportunities, attended 6-8 educational sessions, and developed informed perspective on evaluation. Your first investment will be more thoughtful because of this preparation.

Total time is 6-8 weeks from joining community to making first investment. Many beginners invest within 2-3 weeks. This impatience leads to weak early decisions.

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."

Observation period prepares you for that practice.

Phase 4: First Investment Execution (2-3 Weeks)

Week 1 covers identifying opportunity, conducting due diligence (2-3 hours total), making decision, and indicating commitment through platform. This takes 3-5 hours spread over week.

Week 2 handles reviewing and signing documents electronically (30-60 minutes) and initiating wire transfer (30 minutes). This takes 1-2 hours total.

Week 3 involves confirming funds received and investment complete. Receive final documentation. Add to tracking spreadsheet. This takes 30 minutes.

Total time is 2-3 weeks from deciding to invest to completed first investment. The actual execution is quick once you're ready.

Complete Timeline to First Investment

Week 1-6: Learning and verification. Week 7-8: Community selection and joining. Week 9-16: Observation period. Week 17-19: First investment execution.

Total is 17-19 weeks (approximately 4 months) from absolute zero to completed first investment. This is faster than most people expect. You don't need years of preparation. You need 3-4 months of systematic progression.

Phase 5: Portfolio Building (2-3 Years)

Quarterly pace means making 1-2 investments per quarter (every 12-13 weeks). This sustainable pace builds portfolio without overwhelming you alongside career.

Year 1: 6-8 investments (including first investment from month 4). Year 2: 6-8 investments. Year 3: 6-8 investments. Total: 18-24 investments over three years.

Why this pace works: It's sustainable alongside demanding career (3-5 hours weekly commitment). It allows learning between investments. It's proven to work for thousands of angels.

Why not faster: Making 20 investments in year one prevents learning between decisions. Your earliest investments are weakest. Spacing them out improves quality over time.

Phase 6: The Waiting Years (Years 4-7)

This is phase nobody warns you about. Portfolio is built (15-20 investments complete). Now you wait for outcomes with minimal activity.

What happens: Companies are building products, acquiring customers, potentially raising additional funding. Most make incremental progress. Some struggle. Few show exceptional traction.

What doesn't happen: Exits. Meaningful returns. Clarity about which investments will succeed. Years 4-7 are uncertainty and waiting.

The psychological challenge is real. Maintaining engagement when nothing interesting happens is where most angels quit. They've invested 3 years building portfolio, nothing exciting has happened, and they abandon practice right before outcomes materialize.

Phase 7: Exit Activity (Years 8-12)

Year 8-9 brings first meaningful exits. Companies that have been building for 5-7 years get acquired or occasionally go public. You start seeing actual returns from 1-2 investments.

Year 10-12 is main exit activity period. Several companies from your portfolio exit via acquisitions typically. Some for modest amounts (2-3x returns). Maybe one for meaningful amount (10-20x return) if you're lucky.

Portfolio outcomes clarity emerges. By year 10, you know actual returns. Portfolio returned 2-3x if you're successful. Top quartile might achieve 3-5x. Bottom quartile lose money or barely break even.

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

Learning to recognize them requires seeing outcomes over full 7-10 year cycle.

Complete Timeline Summary

Months 0-4: Learning to first investment. Years 1-3: Building portfolio to 15-20 investments. Years 4-7: Waiting with minimal activity. Years 8-12: Exit activity and realized returns.

Total is 8-12 years from curiosity to knowing actual portfolio returns.

Why Timeline Understanding Matters

Prevents false expectations. Knowing meaningful exits take 7-10 years prevents disappointment during years 2-5 when nothing happens.

Enables commitment. Understanding complete timeline helps you decide whether you can sustain engagement. If 10-year commitment isn't feasible, don't start.

Maintains discipline. Knowing waiting years are normal prevents premature abandonment during boring period when you question everything.

Sets pace. Understanding 2-3 year portfolio building timeline prevents rushing through investments without learning between them.

Timeline Accelerators

Systematic learning in focused 20-30 hours during weeks 3-6 is faster than casual reading over months. Intensity beats duration.

Community infrastructure through joining immediately after verification is faster than trying to source deals independently for months while building networks.

Consistent deployment by making 1-2 investments quarterly for three years is faster path to proper portfolio than sporadic investing over 5-6 years.

Angel Squad enables appropriate pacing: structured onboarding gets you started in weeks not months, curated deal flow from Hustle Fund's pipeline supports consistent quarterly investing, educational programming maintains engagement through waiting years, and community of long-term members demonstrates what sustaining practice through full timeline looks like.

The timeline from curiosity to first investment is faster than you think (3-4 months). The timeline to meaningful outcomes is slower than you think (7-10 years). Get both expectations right and you'll maintain appropriate pace through entire journey.