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

Six months ago, Sarah had never evaluated a startup. She worked in product management at a healthcare company, had saved about $50K, and kept hearing her colleagues talk about angel investing. She wanted in but had no idea where to start.

Today, she's made three investments, serves as an advisor to two companies, and is actively building relationships with founders in the digital health space. Her transformation isn't unique. It's exactly what happens when communities provide the right structure.

The Cold Start Problem for New Investors

Here's what stops most people from becoming angel investors: they don't know where to begin.

You can't just wake up and start investing in startups. You need deal flow, which requires a network. You need judgment, which requires experience. You need confidence, which requires seeing your reasoning validated by people who know what they're doing.

It's a catch-22. You can't get good without investing, but you shouldn't invest until you're good. Most people get stuck in this loop and never start.

Communities solve the cold start problem by providing structure. Instead of fumbling around trying to find deals and figure out evaluation frameworks, you're given a clear path from complete beginner to active investor.

Phase One: Build Your Foundation

The first thing communities do is give you a baseline understanding of how early-stage investing actually works.

At Angel Squad, new members start by attending weekly virtual events where they see real companies pitch. This isn't theory. It's watching a founder explain their business, hearing investors ask questions, and seeing how experienced people evaluate opportunities.

After your first few events, you start to notice patterns. Every founder talks about market size, but the good ones can explain exactly how they'll capture their initial segment. Every company has competition, but the strong ones articulate their differentiation clearly. You're building pattern recognition without realizing it.

The education piece matters more than people think. Angel Squad brings in speakers like Turner Novak and Ann Miura-Ko who explain their evaluation frameworks. You're learning from people who've written hundreds of checks and seen the outcomes. When Elizabeth Yin breaks down why customer acquisition cost matters more than total addressable market at pre-seed, that's not academic. It's wisdom from backing 800+ companies.

This foundation phase usually takes 2-3 months. You're not writing checks yet. You're absorbing how to think about startups, learning the vocabulary, and getting comfortable with the pace of early-stage investing.

Phase Two: Start Evaluating Deals

Once you've got the basics, communities push you to actively evaluate opportunities.

This is where things get real. You're no longer passively watching pitches. You're writing investment memos, articulating your thesis, and defending your reasoning to peers.

Here's what that looks like in practice. Angel Squad shares deals from Hustle Fund's pipeline. Members can choose to co-invest, but first, they need to do the work. That means reading the deck, researching the market, identifying risks, and deciding if the opportunity makes sense.

The forcing function is critical. When you know you'll have to explain your thinking to others, you can't be lazy. You can't just invest because the founder seemed smart or the market is hot. You need coherent reasoning.

What's fascinating is how fast people develop judgment. After evaluating 10-15 companies, you start to see things you missed before. The founder who dodges questions about competition. The financial projections that don't account for customer churn. The market that's actually way more saturated than it appears.

Communities accelerate this because you're not learning alone. When you think a deal looks great and someone points out a fatal flaw you missed, that's a lesson that sticks. When you spot something problematic and experienced investors validate your concern, that builds confidence.

Phase Three: Make Your First Investment

The transition from evaluating deals to actually writing checks is psychological as much as financial.

New investors often feel paralyzed. What if I pick wrong? What if I lose all my money? What if I embarrass myself?

Communities help because you're not making decisions in isolation. You're co-investing alongside experienced people who've done the diligence. If Hustle Fund is backing a company and allocating space for Angel Squad members, that's a signal that the opportunity has been vetted by professionals.

This doesn't mean you should blindly follow. It means you can make your first investment with more confidence because you're not alone in your assessment.

Sarah's first investment was in a digital health startup building remote patient monitoring tools. She saw the deal through Angel Squad, did her own research, talked to three members who had healthcare experience, and decided the founder's domain expertise and early traction justified a $5K check.

Was it scary? Absolutely. But she had a community to lean on. When she had questions about the cap table structure, someone explained it. When she worried about the competitive landscape, another member with 15 years in health tech walked her through why this approach was differentiated.

That support system is the difference between making your first investment and staying on the sidelines forever.

Phase Four: Build Your Portfolio Strategy

After your first investment, communities help you think strategically about portfolio construction.

Most first-time angels make random investments. They hear about a cool company and write a check without considering how it fits into their broader strategy. This is a mistake. Angel investing requires diversification, and that requires intentionality.

Communities like Angel Squad expose you to enough deal flow that you can actually build a coherent portfolio. Instead of making 2-3 random bets, you can deploy capital across 10-15 companies over 2-3 years in a way that balances risk and opportunity.

This is where the Venture Fellows Program becomes relevant. Members who want to get serious about investing join quarterly cohorts where they work directly with Hustle Fund on deal evaluation. You're seeing the same deal flow that professional investors see, learning how they think about portfolio strategy, and building relationships with founders.

The goal isn't to become a VC. It's to build a track record that demonstrates you can source, evaluate, and support early-stage companies. For some people, that's an end in itself. For others, it's the foundation for raising their own fund or joining a firm full-time.

Phase Five: Contribute Back to the Ecosystem

The most successful community members don't just take. They contribute.

This happens organically. After you've made 5-10 investments, you have experience worth sharing. When new members ask about how to evaluate a SaaS startup, you can point them to patterns you've noticed. When someone's considering a deal in your domain, you can offer perspective.

At Angel Squad, members who've built expertise in specific sectors become go-to resources. Someone asks about climate tech, and the community knows to tag the member who's made eight investments in that space. Someone's evaluating an AI startup, and the former ML engineer jumps in with technical questions that nobody else thought to ask.

This contribution creates a flywheel. The community gets stronger as members level up, which attracts better deals, which helps more people become better investors. Everyone wins.

What This Actually Requires

Let me be direct about what it takes to go from beginner to active investor through a community.

Time commitment. You can't show up once and expect to transform. Plan on attending weekly events, reading deal memos, asking questions, and engaging with other members. Figure 5-10 hours per month minimum.

Capital to deploy. Communities give you access to deals, but you still need money to invest. Most people start with $25K-$50K they can deploy over 2-3 years. You don't need millions, but you do need something.

Willingness to look dumb. You're going to ask basic questions. You're going to evaluate deals wrong. You're going to miss obvious things. That's fine. The people who succeed are the ones who ask anyway and learn from their mistakes.

Active participation. Passive consumption doesn't work. You need to write memos, debate deals, and share your thinking. The learning happens in the doing.

Why Most People Don't Do This

If communities make angel investing accessible, why doesn't everyone join one?

Partly because people don't know they exist. Angel investing still feels like an exclusive club, and many communities don't do a great job of marketing themselves.

But mostly it's inertia. Most people interested in angel investing stay interested without taking action. They think about it, talk about it, maybe read a book about it, but never actually start. Communities force you to start.

That activation energy matters. When you've committed to a community, paid membership fees, and scheduled time for weekly events, you're way more likely to actually make investments than if you're just thinking about it abstractly.

The Long-Term Impact

The transformation from beginner to active investor isn't just about making a few investments. It's about joining an ecosystem.

Sarah, the product manager from the beginning, didn't just invest in three startups. She's now advising two companies, has built relationships with 20+ founders in digital health, and is actively sourced by other investors for her domain expertise. Her network and knowledge compound over time.

That's the hidden value of communities. You're not just learning to invest. You're becoming part of a network that creates opportunities for decades. The founders you back introduce you to other founders. The investors you meet become collaborators on future deals. The expertise you build opens doors you didn't know existed.

Angel investing communities don't just turn beginners into active investors. They turn isolated individuals into connected participants in the startup ecosystem. That's a fundamentally different outcome than writing a few checks and hoping for the best.