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

People ask what daily life in a startup investing community actually looks like. Not the marketing pitch. The real time commitment, activities, and engagement.

Walking through a typical month so you know exactly what to expect.

Week 1: Deal Flow and Initial Screening

Monday morning starts with new deal flow. Angel Squad members receive 3-5 new investment opportunities that passed Hustle Fund's initial screening from their pipeline of 1,000+ monthly applications.

Each opportunity comes with an investment memo. You spend 20-30 minutes per company reviewing the deck, reading the memo, and deciding if it's worth deeper evaluation.

Most deals you'll pass on immediately. Wrong stage, outside your thesis, team doesn't excite you. That's fine. You're building pattern recognition about what interests you.

Tuesday evening might include a live pitch call. A founder presents for 15 minutes, then 30 minutes of Q&A. You listen to what questions experienced investors ask. How do they probe on customer acquisition? What concerns them about competitive dynamics?

You don't need to ask questions yourself. Just listening builds judgment about what matters versus what's noise.

Thursday you might discuss one of the week's deals with other community members. Someone with healthcare experience shares perspective on a digital health company. An engineer evaluates the technical approach. You're learning from peers' expertise.

Total time week one: 3-4 hours reviewing deals and attending one evening session.

Week 2: Educational Programming

Week two focuses on education. Tuesday evening features a session on understanding SAFEs and convertible notes. An experienced investor walks through actual term sheets, explaining how caps, discounts, and pro-rata rights actually work.

This isn't generic content. It's tactical guidance from someone who's negotiated hundreds of deals.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Investing requires practice like everything else. So you have to see a lot and invest a lot to get better." Educational sessions provide frameworks for that practice.

You spend an hour Tuesday evening in the session, then maybe 30 minutes afterward reviewing your own investments' terms. Do you actually understand what you bought? How would different scenarios affect your returns?

Wednesday you review new deal flow. Another 3-5 companies. You're getting faster at initial evaluation. Some patterns are obvious now. Weak founding teams. Unclear business models. Markets that seem too small.

Friday afternoon you participate in async discussion about one particularly interesting deal. Other members share their perspectives. You ask questions. Someone points out a risk you hadn't considered.

Total time week two: 4 hours including education session and deal review.

Week 3: Making Investment Decisions

Week three is when you might make an investment decision. One of the companies from week one looks genuinely interesting after deeper evaluation.

You spend an hour Monday evening doing lightweight due diligence. You check the founders' LinkedIn backgrounds. Google the company to see press coverage. Look at who else is investing.

Tuesday you talk to the founders during office hours. You ask about their burn rate, customer pipeline, and specific product roadmap. They're honest about challenges. You get a good sense of whether they're being realistic or overly optimistic.

Wednesday you commit to invest $1,000. Through the community, this is simple. You confirm your amount, and they handle all paperwork through their SPV structure.

You document why you're investing. Founders seem capable. Market is growing. Business model makes sense. You're not certain it'll succeed (you never are), but the risk-reward feels appropriate for a small check.

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." This investment is one piece of your broader portfolio strategy.

Thursday and Friday you review new deal flow as usual. The weekly rhythm is becoming natural.

Total time week three: 5 hours including due diligence and investment decision.

Week 4: Community Building and Deeper Learning

Week four emphasizes community interaction. Tuesday evening features a "portfolio review" session. The community examines companies funded 12 months ago. What happened? Did original theses prove correct? What did investors miss?

This feedback loop is incredibly valuable. You see real outcomes from real investment decisions. The company everyone was excited about is struggling. The one people were lukewarm on is crushing it. Why?

You learn more from these outcome reviews than from any forward-looking analysis.

Wednesday you connect one-on-one with another member who has similar investment interests. You're both interested in B2B SaaS. You discuss evaluation frameworks. What metrics matter most? How do you think about customer concentration?

These peer relationships become your most valuable resource over time.

Thursday you help a portfolio company by making an introduction to a potential customer. This takes 15 minutes but builds goodwill with founders and other investors.

Friday afternoon you reflect on the month. Four weeks in, you've evaluated 12-15 companies, attended two educational sessions, made one investment, and built several relationships with other investors.

Total time week four: 3 hours.

What the Month Reveals

Total time across four weeks: 15-16 hours. That's roughly 4 hours weekly, concentrated in evenings and one weekend afternoon.

For most people with full-time jobs, this is manageable. You're not sacrificing weekends or staying up late. You're investing time you might otherwise spend on professional development, side projects, or learning new skills.

The activities break down roughly as:

• 40% reviewing new deal flow
• 25% educational programming
• 20% community interaction
• 15% due diligence and decisions

This rhythm is sustainable long-term. It's not overwhelming in any single week, but the consistent exposure compounds. By month three, your pattern recognition is noticeably better. By month six, you're contributing valuable perspectives to community discussions.

What Changes Over Time

Your first month feels overwhelming. Everything is new. You don't understand half the terminology. You can't evaluate companies confidently.

By month three, the rhythm feels natural. You quickly identify interesting deals. You understand what questions to ask founders. You have opinions worth sharing.

By month six, you're helping newer members. You're making introductions between investors. You're participating more actively in due diligence.

The time commitment stays roughly the same (3-5 hours weekly), but the value you extract increases dramatically.

What You Don't Do

Notably, you're not spending time on things solo investors must handle:

You're not sourcing deal flow through networking events. You're not negotiating investment terms with founders. You're not managing cap table tracking. You're not organizing tax documents across multiple investments.

The community handles infrastructure so you focus on evaluation and learning.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." The community structure helps you find those founders without consuming your life.

The Realistic Picture

A month in a startup investing community isn't glamorous. You're not attending fancy events or meeting celebrity founders. You're reviewing pitch decks on your laptop, attending Zoom calls from your living room, and discussing due diligence findings in Circle threads.

But this steady, consistent practice is exactly what develops real investment judgment. The flashy parts of angel investing (closing deals, attending demo days) matter less than the boring discipline of systematic evaluation.

Angel Squad provides this structured monthly rhythm through Hustle Fund's curated pipeline, weekly educational programming, and community of 2,000+ investors learning together. The 3-5 hours weekly commitment is manageable alongside full-time work, and the consistent exposure to quality opportunities builds pattern recognition faster than sporadic solo investing. 

Members evaluate opportunities monthly, attend educational sessions from experienced VCs, and build relationships with other investors, all without the infrastructure burden that consumes solo investors' time.

A month inside a startup investing community is less exciting and more educational than most people expect. That's actually why it works.