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

Three months from now, you could be an active angel investor with your first investment closed. Not because you've suddenly become an expert, but because you've focused your learning and practiced enough to make informed decisions.

The exact progression from zero knowledge to first deal.

Days 1-7: Understanding the Basics

Your first week is about orientation. What is angel investing? How does it work? What are you actually buying when you invest in startups?

Start with the fundamentals. Angel investors provide capital to early-stage startups in exchange for equity. You're betting that some small percentage of your investments will succeed dramatically enough to return your entire portfolio and then some.

This is different from public market investing. Most of your investments will fail completely. You won't have liquidity for years. Your winners need to return 100x or more to make the portfolio math work.

Understanding this reality upfront is crucial. Angel investing isn't about picking stocks. It's about portfolio construction and power law returns.

Spend week one consuming content about how angel investing works. Read blog posts from experienced angels. Watch educational videos. Join a community so you can start seeing real deal flow and educational programming.

Days 8-14: Learning the Language

Week two is about terminology. What are SAFEs? How do valuations work? What's the difference between pre-money and post-money? What are cap tables and why do they matter?

You don't need to become an expert on these topics immediately. But you need enough understanding to follow along when investors discuss deals.

Most good communities run educational sessions specifically covering these basics. Attend those sessions and ask questions about anything you don't understand.

The goal isn't mastering everything. It's developing enough literacy to participate in discussions and evaluate basic deal terms.

Days 15-30: Seeing Real Opportunities

Weeks three and four are about exposure. Start reviewing actual investment opportunities even though you're not ready to invest yet.

Read pitch decks. Listen to founder pitches. Pay attention to what questions experienced investors ask. Notice which companies get interest and which don't.

You're building pattern recognition. What do strong founding teams look like? How do investors think about market size? What business models seem genuinely interesting versus overhyped?

Don't stress about understanding everything. Just absorb information and start noticing patterns.

Angel Squad members get immediate exposure to opportunities from Hustle Fund's pipeline, seeing how professional investors evaluate companies from day one.

As Elizabeth Yin, co-founder and GP of Hustle Fund, notes: "Investing requires practice like everything else. So you have to see a lot and invest a lot to get better." These first few weeks of seeing deals without investing is part of that practice.

Days 31-45: Developing Frameworks

Weeks five and six are when you start developing evaluation frameworks. How do you actually assess whether a company is interesting?

Different investors use different frameworks. Some focus heavily on founders and team quality. Others emphasize market size and timing. Still others prioritize business model and unit economics.

None of these approaches is objectively right. What matters is developing a framework that makes sense to you and applying it consistently.

Your framework will evolve over time. But having some systematic way of thinking about opportunities is better than just going with gut feel.

This is also when you should start developing your investment thesis. What types of companies are you most interested in? B2B SaaS? Consumer products? Climate tech? Healthcare?

You don't need to be overly restrictive. But having a loose focus area helps you evaluate opportunities more effectively and build useful expertise.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." Your framework helps you recognize great founders beyond obvious patterns.

Days 46-60: Identifying First Investment

Weeks seven and eight are when you start actively looking for your first investment. You're not just passively reviewing deals anymore. You're specifically evaluating which opportunity should be your first check.

What makes a good first investment? Honestly, almost any reasonable opportunity works. Your first investment is as much about practice as finding the perfect company.

Look for companies where you understand the market, believe in the founders, and think the business model makes basic sense. Don't overthink it.

The bigger risk is not investing at all because you're waiting for the perfect opportunity. Better to invest in something good enough and learn from the experience.

Angel Squad's structure of $1,000 minimums makes it easy to start with a small, manageable first investment while building toward a larger portfolio.

Days 61-75: Due Diligence Basics

Weeks nine and ten are when you do lightweight due diligence on your first investment. This doesn't mean extensive background checks or detailed market analysis. It means basic verification that things are as they seem.

Talk to the founders. Ask about their traction, burn rate, and plans. Check that their claims about customers or partnerships are real. Get a sense of whether they're being honest or inflating things.

Look at the other investors in the round. Are experienced people investing? That's a good signal even if you're new.

Review the terms. Do you understand what you're getting? Are the terms standard or weird?

For your first investment, you're mostly learning the process. Don't expect to uncover major insights that experienced investors missed.

Days 76-90: Making Your First Investment

Weeks 11-12 are when you actually commit capital and close your first investment. This is simultaneously exciting and terrifying.

Start with a small check. $500-1,000 is plenty for your first investment. You're proving to yourself that you can actually do this, not betting big on a single opportunity.

The mechanics of investing vary depending on whether you're investing through a network or independently. Networks typically handle all the paperwork through SPVs or rolling funds. You just commit your amount and they manage the rest.

If investing independently, you'll need to sign a SAFE or other investment document directly with the company. Read it carefully even if you don't understand every clause.

After you invest, document your thinking. Why did you invest? What do you expect to happen? What risks concern you?

This documentation is crucial for learning. Six months from now, you'll review whether your initial thesis was correct.

The Common Mistakes to Avoid

The biggest mistake new investors make in their first 90 days is analysis paralysis. They research endlessly but never actually invest because they're waiting to feel certain.

You'll never feel certain. Angel investing is inherently uncertain. The point of starting with small checks is accepting that uncertainty while building experience.

Another common mistake is investing too much too fast. Your first investment should be small. $500-1,000 max. Not $5,000 or $10,000.

Third mistake is ignoring portfolio construction. Your first investment is the start of a portfolio, not a concentrated bet. Think about diversification from day one.

What Happens After Day 90

By day 90, you've made your first investment and started your journey as an angel investor. But you're just beginning.

Over the next 6-12 months, make 5-10 more investments to build an actual portfolio. Continue participating in educational programming. Learn from watching how your early investments develop.

The skills you build in the first 90 days compound over time. Pattern recognition improves. Evaluation frameworks sharpen. Decision-making gets faster and better.

Why 90 Days Works

Three months is enough time to develop basic competency without overthinking things. It's long enough to learn fundamentals and see multiple opportunities. Short enough that you don't get paralyzed by endless research.

The timeline works because communities compress learning. Instead of spending months trying to find deals, you get consistent deal flow from day one. Instead of figuring out evaluation frameworks yourself, you learn from experienced investors.

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." The 90-day timeline to first investment is the beginning of getting those reps.

The Role of Community Structure

Communities make the 90-day timeline possible by providing structure. Week one you're learning basics through educational content. Week two you're seeing real deals. Week four you're participating in discussions. Week eight you're ready to invest.

Without structure, most people take 12-18 months to make their first investment because they don't know what to learn or when they're ready.

Angel Squad is designed specifically for this 90-day progression. From day one, you get access to Hustle Fund's deal pipeline so you're seeing real opportunities immediately. Weekly educational programming builds your knowledge systematically. 

A community of 2,000+ investors provides peer support and examples of other beginners making their first investments. And $1,000 minimums mean your first investment is meaningful but not scary. The structured approach turns "I'm interested in angel investing" into "I'm an angel investor with my first deal closed" in three months rather than three years.

The gap between curiosity and action is smaller than you think. It's 90 days of focused learning and practice. Not three years of preparation.