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

Everyone wants to know what happens when you join an angel investor network. Not the marketing promises. The actual experience month by month.

What your first year typically looks like, based on real investor journeys through communities like Angel Squad.

Month 1: Drinking from the Firehose

Your first month is overwhelming. You're exposed to 15-20 investment opportunities, attending educational sessions on topics you barely understand, and trying to keep up with community discussions using terminology you don't recognize.

Everything feels foreign. What's a SAFE? Why does the cap matter? How do you evaluate if a market is big enough? Who cares about unit economics?

The smartest thing you can do in month one is accept that confusion is normal. Don't try to invest immediately. Just absorb information and start building pattern recognition.

Most people make the mistake of trying to understand everything perfectly before participating. Better approach: participate actively while accepting you won't understand everything yet.

Attend pitch calls even if you can't evaluate the companies well. Join discussions even if you feel behind. Ask basic questions without embarrassment. Everyone was confused at first.

Month 2: Starting to See Patterns

By month two, things start clicking. You've seen enough pitches to recognize what strong founders sound like versus weak ones. You understand basic metrics like burn rate and runway. You can follow conversations about different business models.

You're probably still not ready to invest, but you're developing opinions. "This team seems unfocused." "That market feels too small." "I don't understand how they'll acquire customers."

These gut reactions are the beginning of investment judgment. They're not sophisticated yet, but they're data points you'll refine over time.

This is also when you might make connections with other new investors going through the same learning process. These peer relationships often become your most valuable resource. You can ask "dumb" questions to each other that you're embarrassed to ask publicly.

Month 3: First Investment Decision

Most investors make their first investment around month three. You've seen enough deals to have developed some basic frameworks. You understand the terms well enough to not be completely confused. You're ready to actually commit capital.

Your first investment probably won't be perfect. You might invest for the wrong reasons. You might miss obvious risks. That's fine. The goal is putting money to work and learning from the experience.

As Eric Bahn, co-founder and GP of Hustle Fund, emphasizes: "Investing requires practice like everything else. So you have to see a lot and invest a lot to get better." Your first investment is the start of that practice.

The amount matters less than the act of doing it. $500 or $1,000 is plenty. You're building experience, not betting the farm.

Angel Squad members often make their first investment around this timeline, with access to Hustle Fund's curated opportunities and $1,000 minimums making it easy to start building a portfolio.

Months 4-6: Building a Portfolio

Quarter two is when you transition from "I made one investment" to "I'm building a portfolio." You make 2-3 more investments across different sectors or business models.

This diversification is deliberate. You're learning what types of opportunities interest you, which markets you understand well, and what founder characteristics you value most.

You're also starting to track your thinking. Why did you invest in this company? What are you expecting to happen? What risks concern you?

Writing down your investment thesis before investing is crucial. Six months later, you can review whether your thinking was correct or misguided. This feedback loop is how you actually improve.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Don't try to pick a company. Select a portfolio. One of the biggest mistakes new investors make is thinking they can really pick well and putting a big chunk of cash on one company."

Communities help enforce this discipline by making it easy to invest across multiple opportunities rather than concentrating capital.

Months 7-9: Developing Judgment

By month seven or eight, your judgment is noticeably better than when you started. You can evaluate opportunities more quickly. You understand what questions actually matter versus which are noise.

You're also getting feedback on your early investments. Some companies are executing better than expected. Others are struggling. One might have already shut down.

These outcomes inform your future decisions. The company you were most excited about is flailing. The one you were lukewarm on is crushing it. Why? What signals did you miss?

This is also when you might start helping portfolio companies. Making introductions. Providing advice. Building relationships with founders that extend beyond just the initial check.

Months 10-12: Becoming an Active Investor

By the end of year one, you've probably made 6-10 investments. You've developed real opinions about what matters. You've built relationships with other investors and founders. You're an active participant in the community.

You still have a ton to learn. You'll make mistakes for years. But you're no longer a complete beginner. You have frameworks for evaluating opportunities. You understand portfolio construction. You can contribute meaningfully to discussions.

The progression from "I'm interested in angel investing" to "I'm an angel investor" happened gradually over twelve months. Not because you got smarter or luckier, but because you practiced consistently within a structured environment.

What Metrics Actually Matter

At the end of year one, don't judge success by financial returns. You won't have meaningful exits yet. Early-stage investments take 7-10 years to mature.

Better metrics:

Number of investments made (target: 6-12). Diversity of portfolio (different stages, markets, business models). Quality of relationships with founders and other investors. Frameworks developed for evaluating opportunities. Understanding of what you still need to learn.

If you've made 8-10 investments across diverse opportunities, built relationships with smart people, and developed some frameworks for decision-making, year one was successful regardless of financial returns.

Common Mistakes in Year One

The biggest mistake new investors make is waiting too long to invest. They spend 6-9 months "learning" without putting capital to work. They're not actually learning, they're procrastinating.

Another common mistake is concentrating too early. They find one company they love and invest $5,000-10,000 instead of spreading that across multiple opportunities. This defeats the purpose of portfolio construction.

Third mistake is ignoring education in favor of just making investments. You need both. The educational programming and community discussions are what help you make better decisions over time.

How Skills Develop Over Time

Month 1: Learning terminology and basic concepts. Month 3: Can follow pitch calls and understand basic metrics. Month 6: Developing frameworks for evaluation. Month 9: Can articulate why you're investing in specific opportunities. Month 12: Contributing valuable perspectives to community discussions.

This progression happens naturally through consistent exposure and practice. You don't need to force it or stress about whether you're learning fast enough.

The Compounding Effect

What's not obvious in year one is how the learning compounds. The relationships you build lead to future deal flow. The frameworks you develop make evaluation more efficient. The pattern recognition you build helps you spot opportunities others miss.

By year two, you're not just more experienced. You're part of a network that actively improves your investing. Other investors refer deals to you. Founders seek you out. Your judgment is genuinely better.

This compounding is why consistent participation in a good network is so valuable. Each month builds on previous months in ways that accelerate your development.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." By year's end, you're better at recognizing great founders beyond obvious patterns.

Beyond Year One

After your first year, the question becomes whether you want to continue and expand your angel investing practice or stay at current levels.

Some investors decide they enjoy it and want to increase their annual investment budget. They might go from $10,000 per year to $25,000 or $50,000. Their check sizes might increase from $1,000 to $2,000-5,000.

Others decide they prefer staying at lower levels. They like being involved but don't want angel investing to be a major focus. That's fine too. You can participate meaningfully with just $10,000-15,000 annually spread across 5-8 investments.

The first year gives you the information to make this decision intelligently. You know whether you enjoy the process. You understand the time commitment. You have realistic expectations about returns.

What Success Looks Like

By the end of year one in a good angel network, success means you've transformed from someone interested in angel investing to someone actively building a portfolio and developing as an investor.

You've made multiple investments across different opportunities. You've developed frameworks for evaluation. You've built relationships with other investors and founders. You've started to understand what you don't know.

The financial returns won't be clear for years. But the learning, relationships, and experience are immediate and valuable regardless of how individual investments perform.

Angel Squad provides the structure for this twelve-month progression. Weekly deal flow means consistent exposure to opportunities. Educational programming builds frameworks systematically. A community of 2,000+ investors provides peers at every stage of development. 

And $1,000 investment minimums let you build a real portfolio during year one rather than making just 1-2 concentrated bets. The consistent rhythm of programming, deal flow, and community interaction creates the practice cadence that transforms beginners into active investors over twelve months.

The year-one timeline is predictable if you participate consistently. Month one is overwhelming. Month six you're building confidence. Month twelve you're an active investor with a growing portfolio. The specific deals change, but the progression is remarkably similar across investors who engage seriously.