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

You can learn angel investing the hard way or the slightly-less-hard way.

The hard way looks like this: you write checks into startups based on gut feeling and founder charisma. You invest $25,000 into one or two companies because you're "high conviction." You wait five years to discover that both companies shut down and you lost everything. You conclude angel investing is gambling and never do it again.

The slightly-less-hard way looks like this: you join a community of investors who've already made these mistakes. You invest smaller amounts across 20-30 companies. You learn evaluation frameworks from people who review thousands of deals. You get real-time feedback that helps you avoid obvious traps. Some investments still fail, but your winners more than cover your losses.

The difference between these paths is dramatic. Stanford research found that angels in structured groups had portfolio returns 2.5x higher than solo investors. That's not a small edge. That's the difference between breaking even and generating wealth.

Why Solo Investing Is Playing on Hard Mode

Let me explain why going solo is brutal. You're trying to compress 10 years of pattern recognition into your first deal evaluation. You don't know what good retention looks like. You can't spot red flags in founder dynamics. You can't tell if a market is actually big enough to support venture returns.

So you rely on superficial signals. The founder went to a good school. The product demo looks polished. Other investors you've heard of are in the round. These signals occasionally correlate with success, but they're not predictive.

Meanwhile, you're competing against investors who've evaluated 1,000+ companies. They know that polished demos often hide weak product-market fit. They know which questions actually reveal founder quality versus which questions just make you sound smart.

The information asymmetry is massive. And expensive. A solo investor who writes three $20,000 checks into companies that fail has lost $60,000 while learning what experienced investors already knew.

How Communities Compress the Learning Curve

Angel Squad members see 50-100 deals per year just by showing up to weekly pitch events. That exposure alone is worth thousands in tuition.

But the real learning happens in the discussion after each pitch. Someone points out that the customer acquisition cost is too high relative to lifetime value. Another person notes that the founding team doesn't have domain expertise in the market they're attacking. A third investor shares that they saw a similar company fail two years ago for specific reasons.

You're not just seeing deals. You're hearing experienced investors explain their thinking in real-time. When Shiyan Koh says she's concerned about competitive dynamics, you learn what meaningful competitive moats look like. When Elizabeth Yin explains why she thinks a founder has strong customer understanding, you internalize the actual questions that reveal this.

Over 12 months of active participation, you've effectively compressed 5 years of solo learning into one year of accelerated pattern recognition. That ROI is difficult to quantify but impossible to ignore once you experience it.

The Portfolio Construction Mistake That Kills Beginners

Here's a mistake new angel investors make: concentrating capital in too few deals because they think they're smarter than everyone else.

They find a company they love. The founder is charismatic. The market seems huge. They invest $50,000 because they're "high conviction." When the company fails (which happens 70% of the time), they've lost most of their angel investing budget on one bet.

The math is unforgiving. Angel investing follows power law distributions. Your best deal will generate more returns than all your other deals combined. But you don't know which deal that is upfront. So you need enough shots on goal to capture that one winner.

Professional angels invest in 30-50 companies over several years. They know that most will fail, a few will return 2-3x, and one or two might generate 50-100x returns. The strategy only works if you have adequate diversification.

Communities make this diversification possible through low check sizes. Angel Squad allows $1,000 minimums per deal. At that level, you can invest in 20-30 companies over 2-3 years without depleting your capital. You're building a real portfolio, not making one or two random bets.

The Value of Real-Time Feedback

Solo investors make decisions in a vacuum. They analyze a deal, decide to invest, and find out years later if they were right. There's no feedback loop to improve their judgment in the meantime.

Communities provide immediate feedback. At Angel Squad, members write investment memos explaining their thesis. Other investors review these memos and point out gaps in reasoning or overlooked risks.

This feedback is invaluable. Maybe you're overweighting market size and ignoring execution risk. Maybe you're too focused on the product and missing red flags in the business model. Getting this feedback before you invest saves capital.

The peer review also builds pattern recognition faster. When you see other investors' memos and the feedback they receive, you're learning from their analysis too. You're effectively 10x'ing your deal exposure because you're learning from everyone else's due diligence work.

Access to Domain Experts You'll Never Meet Otherwise

No one person can be an expert in fintech, climate tech, biotech, B2B SaaS, and consumer apps. But a community of 2,000+ investors definitely has deep experts in every vertical.

When you're evaluating a climate tech deal and someone in the community has spent 15 years in renewable energy, their perspective is worth way more than anything you could learn from googling. When you're looking at a fintech company and another member worked at Stripe for 6 years, their insights on go-to-market strategy are gold.

Angel Squad facilitates these connections through sector-specific channels and 1:1 matching. If you're interested in a specific vertical, you get connected with members who have domain expertise. This accelerates learning and helps you avoid obvious mistakes.

The Emotional Support Nobody Talks About

Angel investing is emotionally difficult. You invest in 20 companies. Fifteen fail over the next 5 years. Three churn along without meaningful traction. One gets acquired for a small exit that barely returns your capital.

When you're solo, these losses feel personal. You question your judgment. You wonder if you should quit. You don't have anyone to talk to who understands the timeline and power law dynamics of early-stage investing.

Communities normalize the experience. Everyone else is going through the same thing. Your failures don't mean you're bad at this. They mean you're playing the game correctly. The patient capital mindset is easier to maintain when you're surrounded by people who've been doing this longer and can reassure you that the wins take time.

Angel Squad members share their portfolio outcomes openly. When someone's investment goes to zero, others share similar experiences. When someone gets a meaningful exit, the community celebrates together. This social reinforcement matters more than people expect.

Making Community Work for You

If you're a beginner who's serious about angel investing, here's how to extract maximum value from community membership.

Show up consistently to pitch events. You're not just evaluating deals. You're learning frameworks by listening to how experienced investors think through opportunities. Take notes on the questions they ask and the concerns they raise.

Write investment memos for deals you're considering. Share them with the community and actively seek critical feedback. The goal isn't validation. It's stress-testing your thesis before you deploy capital.

Start small with $1,000-2,000 per deal. Build portfolio diversification over 2-3 years before increasing check sizes. The goal is developing judgment, not swinging for home runs on limited information.

Be patient. Your first investments won't exit for 5-7 years minimum. The community helps you maintain the long-term mindset necessary for early-stage investing to work.

For beginners ready to start angel investing intelligently, communities like Angel Squad provide the structure, education, and peer network that dramatically improve outcomes. You'll still lose money on most deals. But you'll develop the judgment and portfolio construction discipline needed to capture the winners when they hit.