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

A friend asked me recently if Angel Squad was "worth it" for someone making their first angel investments. She'd done the math, $3,500 per year plus actual investment capital. Was that going to lead to real returns?

Fair question. Let's talk about what "worth it" actually means when you're evaluating online angel investing communities.

The ROI Question Nobody Wants to Answer

Most angel investments fail. Even the smartest investors with the best deal flow will see 70-80% of their portfolio companies either die or return less than 1x.

So when you're asking if an angel investing community is "worth it," you can't just look at membership fees. You have to look at whether joining actually increases your chances of backing winners.

The answer is yes, but not for the reasons most people think.

What You're Actually Paying For

When you pay $3,500 per year for Angel Squad, you're not really paying for deal flow. You can find startups to invest in on Twitter for free. You're paying for four things that are much harder to get on your own:

Deal quality filtering. Hustle Fund reviews 1,000+ deals every month. They invest in 2-3 of them. That's a 0.2% acceptance rate. You're essentially outsourcing the hardest part of angel investing (sourcing and initial screening) to a professional team.

Education that's actually useful. Most angel investing content online is either too basic ("what is an angel investor?") or too advanced (modeling out complex cap table scenarios). Communities teach you the middle layer: how to actually evaluate a pitch, what questions to ask founders, how to think about market size.

Co-investment alignment. When you invest alongside a VC fund like Hustle Fund, you're on the same terms they negotiated. You're not getting worse pricing or different rights. That alignment matters more than people realize.

Network effects that compound. The person who invested in the same deal as you might become your co-investor in three other companies. Or they might introduce you to a founder raising their next round. These connections multiply your opportunities.

The Hidden Costs of Going Solo

Let's say you skip the community and try to angel invest on your own. What does that actually look like?

You'll spend dozens of hours sourcing deals through LinkedIn, Twitter, and cold intros. You'll evaluate companies without any framework or benchmarks for what good looks like. You'll negotiate terms yourself, probably getting worse pricing than a VC would get. And you'll likely make a bunch of rookie mistakes that cost you money.

The learning curve is expensive. I've met solo angels who invested $50,000 into their first five deals and lost money on all five. Not because they were unlucky. Because they didn't know what they didn't know.

Could you eventually figure it out? Sure. But how much time and capital are you willing to burn while learning?

The Math of Diversification

One of the biggest advantages of communities is they make diversification affordable. Professional angel investors typically aim for 20-30 companies in their portfolio. That's not arbitrary; it's what the math says you need to reliably catch a winner.

If you're writing $50,000 checks, building a 20-company portfolio means deploying $1 million. Most people can't do that.

But if you're writing $2,000 checks through a community, you can build that same 20-company portfolio for $40,000. Suddenly diversification is achievable instead of theoretical.

Angel Squad members who've been active for two years often have 15-25 companies in their portfolio. That's a real portfolio that might actually return capital, not a handful of lottery tickets.

What Success Actually Looks Like

Let's be specific about outcomes. Angel Squad has 2,000+ members who've collectively invested $30 million across 70+ companies. Some of those companies are already showing strong growth.

But here's what matters more: hundreds of members who joined knowing nothing about angel investing now have legitimate portfolios. They understand term sheets. They can evaluate a pitch deck critically. They have relationships with other investors and founders.

Some have started their own syndicates. Some have joined venture funds. Some have raised their own micro-funds. The community became a launchpad for their entire investing career.

Is that worth $3,500 per year? For most people, absolutely.

When Communities Don't Make Sense

I'll be honest about when you shouldn't join an angel investing community.

If you already have exceptional deal flow through your network, you might not need the community's sourcing. If you're already an experienced investor who's made 30+ investments, the education probably won't add much value.

If you can't afford to invest at least $5,000-10,000 per year beyond the membership fee, the math doesn't work. The membership is an expense; the investments are where you hopefully make returns. You need enough capital for both.

And if you're not willing to engage with the community (attending events, asking questions, building relationships), you'll get minimal value. The people who extract the most from these communities are the ones who actively participate.

The 2026 Landscape

The angel investing community space has gotten crowded. There are now dozens of groups offering various combinations of deal flow, education, and networking.

What separates the good ones from the mediocre?

Institutional backing. Communities attached to real VC funds (like Angel Squad with Hustle Fund) have better deal quality than communities run by individuals with no investing track record.

Educational depth. One workshop per quarter isn't enough. You want weekly content, live sessions, recorded resources, and direct access to experienced investors.

Real member outcomes. Ask communities for data on how many deals members have invested in, total capital deployed, and success stories of members who've progressed in their investing careers.

Culture fit. This is subjective but important. Do the current members seem like people you want to learn from? Is the tone welcoming or exclusive? Do people ask good questions?

Angel Squad hits on all four. That's not marketing; it's just accurate.

The Honest Bottom Line

Is an online angel investing community worth it in 2026? For most people interested in angel investing, yes.

The alternative is spending years trying to figure it out on your own, making expensive mistakes, and probably giving up before you see any returns. Communities compress that learning timeline and give you a real shot at building a portfolio that might actually work.

The membership fee is real money. But compared to the cost of bad investments made without guidance, it's a bargain. And if you're serious about angel investing as a 10-20 year activity, the upfront education investment pays dividends forever.

The question isn't whether communities are worth it. It's whether you're willing to commit to learning and engaging with the community you join. If yes, then absolutely join. If no, save your money.