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 spend months circling angel investing before they ever write a check. They read articles, listen to podcasts, maybe attend a webinar or two. Then they get stuck at the same place: "Okay, but what do I actually do?"

Here's the thing about angel investing communities, they're not magic. They won't suddenly make you Warren Buffett. But they can compress what might take you two years of fumbling around into 30 focused days. That matters when every month of delay is a month of missed opportunities.

Let's map out what your first month in an angel investing community should actually look like.

Days 1-7: Getting Your Bearings

Your first week isn't about investing. It's about understanding the terrain.

Start by showing up to everything. Most communities like Angel Squad run weekly virtual events where you can hear directly from founders and see how experienced investors think about deals. The goal here isn't to invest, it's to observe patterns. What questions do veteran investors ask? What makes them excited versus skeptical?

Set up your deal flow system now. This sounds boring but it's crucial. A simple spreadsheet tracking companies, sectors, and your initial thoughts will save you later. You'll see dozens of pitches in your first month. Without a system, they blur together.

Find two or three people in the community who are one step ahead of you. Not the folks who've made 50 investments, they're too far ahead. Look for people who made their first angel investment 6-12 months ago. They remember what confused them. They'll answer your "dumb" questions.

Days 8-14: Learning the Language

Week two is vocabulary week. Angel investing has its own lexicon, and pretending you understand terms when you don't wastes everyone's time.

Dig into the basics: SAFEs, caps, pro rata rights, liquidation preferences. Most angel investing communities have educational content covering this stuff. Angel Squad, for instance, runs sessions breaking down cap table math and how different deal structures actually work in practice. Watch those. Then watch them again.

The difference between understanding these concepts in theory versus seeing them applied to real companies is massive. When a founder says they're raising on a $10 million cap SAFE, you need to instantly calculate what that means for your potential return. That kind of fluency only comes from repetition.

Start attending pitch sessions actively, not passively. Ask at least one question per session. Even if you think it's basic. Other new investors probably have the same question.

Days 15-21: Building Your Investment Thesis

By week three, you should start developing opinions. What sectors interest you? What stage of company? What check size makes sense for your situation?

This is where an angel investing community becomes invaluable. You can test your thinking against people who've been doing this for years. Say you're excited about climate tech, great. Someone in the community has probably invested in 10 climate tech companies and can tell you what worked, what didn't, and what signals to look for.

Your thesis doesn't need to be comprehensive. It needs to be honest. If you want to invest in B2B SaaS because that's what you understand from your day job, own that. Concentrated expertise beats scattered dabbling.

Most communities organize members around interests or sectors. Angel Squad members often become the go-to experts in specific domains, the person everyone asks about healthcare AI, or the expert on logistics tech. That happens because they focused, not because they tried to understand everything.

Days 22-30: Making Your First Investment

The final week is about pulling the trigger.

You've been watching deals. You've been learning. You've built relationships. Now you need to make a decision. This doesn't mean rushing into a bad investment, it means being ready when the right opportunity shows up.

Here's what de-risks your first check: investing alongside experienced investors through an angel investing community. When Hustle Fund shares a deal with Angel Squad members, they're essentially saying "we've done the work, we're putting our money in, and here's why we think this could be interesting." You still need to do your own analysis, but you're not flying blind.

Your first investment will probably be small. Maybe $1,000, maybe $5,000. The exact number matters less than getting over the psychological hurdle of becoming an investor rather than an observer. Once you write that first check, the learning accelerates dramatically because you have skin in the game.

Set up your investment entity if you haven't already. Most people start with direct investments from their personal accounts, but as you get more active, you might want an LLC. Your community can connect you with lawyers and accountants who specialize in this stuff.

What Happens After Day 30

Your first month sets the foundation, but angel investing is a long game. Companies take 7-10 years to exit. Your job is to keep learning, stay connected to the community, and gradually increase your activity as your pattern recognition improves.

The members who get the most value from angel investing communities are the ones who show up consistently. They attend events. They ask questions. They build reputations as people with specific expertise. That leads to better deal flow, stronger networks, and eventually, better returns.

Angel Squad's structure, weekly events, access to vetted deals, direct exposure to how a VC firm thinks, accelerates this process. But the structure only matters if you show up and do the work.

So here's your 30-day roadmap. Week one: observe. Week two: learn the language. Week three: develop your thesis. Week four: make your first investment. Then repeat the cycle, getting slightly better each time.

Angel investing isn't about finding the next unicorn in your first month. It's about building the skills and network that let you consistently identify good opportunities over the next decade. Start with 30 days. See where it takes you.