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 join angel investing communities for the wrong reasons. They hear about someone who invested $1,000 and turned it into $500,000, then rush to sign up for the first program they find. Six months later, they've paid membership fees but haven't made a single investment they feel confident about.

The problem isn't angel investing communities. It's choosing the wrong one. Some networks charge thousands in fees but give you access to deals you could find yourself on LinkedIn. Others promise education but deliver recycled blog posts you could read for free. A few actually deliver on helping you become a better investor.

Here's how to separate signal from noise.

Questions About Deal Flow

1. How many deals does the community see monthly, and how many do members actually get access to?

Volume matters. A community that sees 1,000 deals per month but only shares 2-3 with members (like Angel Squad does with Hustle Fund's pipeline) is applying serious filtering. That pre-vetting saves you dozens of hours reviewing mediocre opportunities. Communities that dump 50 unfiltered deals on you each month are shifting the work to you without adding much value.

2. What's the typical check size, and can I invest as little as $1,000?

Lower minimums mean you can diversify faster. If a community requires $25,000 minimums, you need $250,000 just to build a 10-company portfolio. With $1,000 minimums, you can test investing with $10,000 spread across 10 companies. You learn faster with more reps.

3. What stage are most deals? Pre-seed, seed, Series A?

Match the stage to your risk tolerance. Pre-seed deals offer the most upside but highest failure rates. Series A companies have more traction but lower multiples. Know what you're signing up for.

Questions About Education

4. Who teaches the curriculum, and what's their track record?

Learning from someone who's invested in 500+ companies (like Hustle Fund's team) beats learning from someone with 10 investments. Check if instructors are active investors making real decisions with real money, not just educators who've never written a check.

5. Are sessions live or pre-recorded, and can I ask questions?

Pre-recorded content is fine for basics, but live sessions where you can ask specific questions about deals you're reviewing matter more. Angel Squad runs live deal reviews where GPs Elizabeth Yin, Eric Bahn, and Shiyan Koh walk through actual decisions. That's where you actually learn.

6. Do you cover legal basics, cap tables, and term sheets?

You need to understand what you're signing. Communities that skip the boring but critical stuff (liquidation preferences, anti-dilution protection, pro-rata rights) leave you vulnerable to getting wiped out even when companies succeed.

Questions About Community

7. How many active members are there, and what's the retention rate?

Active is the key word. A community with 10,000 members but only 100 who actually engage won't help you. Look for smaller, highly engaged groups. Angel Squad has 1,500+ members across 40+ countries, with active local chapters that organize monthly meetups.

8. Can I co-invest with other members, or is it just me and the lead?

The best learning happens when you can discuss diligence with peers who are also evaluating the same deal. Communities that facilitate co-investing and peer discussion help you build your network while making better decisions.

9. Is there a "no assholes" policy, and how do they enforce it?

This matters more than you think. Angel investing is already stressful. Communities that let aggressive, know-it-all members dominate discussions make newcomers afraid to ask basic questions. Good communities actively moderate for inclusivity.

Questions About Structure and Costs

10. What's the total cost, including membership fees and carry?

Some communities charge quarterly fees. Others charge lifetime fees. Some take carry on deals. Add it all up. A $3,500 lifetime membership with no carry might be cheaper than $800/quarter for three years.

11. Can I try before committing, and what's the cancellation policy?

Solid communities offer trial periods because they're confident you'll stick around. Angel Squad offers a 14-day free trial. If a community won't let you sample the experience first, that's a red flag.

12. Do I need to be accredited to join, and do you help non-accredited investors get certified?

Some communities are learning-only for non-accredited investors. Others (like Angel Squad) welcome non-accredited members and even cover the cost of the Series 65 test to help you become accredited. Know the rules before you join.

Why This Matters

The difference between a good angel investing community and a mediocre one isn't just deal flow or education. It's whether the community actually helps you develop judgment. Anyone can send you deal memos. Not everyone can help you understand why Hustle Fund passes on 997 out of 1,000 deals they see, or what makes those 3 special.

Angel Squad built its model around this. Members get access to Hustle Fund's Deal Assessment Framework, attend monthly pitch events where founders present live, and participate in deal reviews where GPs explain their thinking in real time. That combination of structured education, curated deal flow, and active community has helped over 1,500 members build portfolios they actually understand.

If you're evaluating communities, start with these 12 questions. The answers will tell you whether you're joining a network that will make you a better investor, or just a network that will make you a member.

Want to see how Angel Squad answers these questions? They offer a 14-day free trial where you can attend live sessions, review current deals, and meet other members before committing. It's worth checking out if you're serious about learning to invest in startups.