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

Should you angel invest solo or join a community?

The data says most people choose communities. That shift isn't random. Communities solve specific problems that solo investors struggle with for years.

But the community versus solo decision isn't about one being universally better. It's about understanding what you're optimizing for and what stage you're at in your investing journey.

The Deal Flow Reality Check

The biggest difference between community and solo investing is deal volume. In an angel network, you see dozens or hundreds of deals filtered through screening processes. Solo, you see whatever comes through your personal network.

Neither is inherently better. It depends on the quality of your network versus the quality of the angel network.

If you're well-connected in startup ecosystems, know founders, have friends at top companies, and stay active in the right communities, your solo deal flow might be excellent. Elizabeth Yin's deal flow at Hustle Fund includes companies that come in cold with no referral. But she's built that reputation over years of sharing tactical investing advice publicly.

If you're just starting or don't have those connections, communities provide access you can't get otherwise. Angel Squad members get to invest alongside Hustle Fund on the same terms when the fund backs companies. You're not negotiating. You're not leading. You're just deciding if you want in on deals a professional VC team already vetted.

Learning Curves Cost Money

Solo investing has lower overhead but higher learning costs. You're not paying membership fees, but you're making more mistakes early on because you don't have experienced investors helping you avoid obvious pitfalls.

Think about what you learn by watching someone evaluate a hundred deals versus doing it yourself. Nicole DeTomasso, speaking at an Angel Squad event about breaking into VC, emphasized that your number one job as an investor is to source and invest in the best deals. But how do you know what "best" looks like when you're new?

Communities compress that learning timeline. Instead of making every mistake yourself, you watch others work through the questions: How do you evaluate a pre-revenue SaaS company? What valuation makes sense for seed-stage biotech? When should you push back on terms? You get pattern recognition from volume without writing every check yourself.

Data backs this up. Portfolios of 10+ startups delivered average returns of 3.5x in 2025 compared to about 2.6x for smaller portfolios. Communities help you build that portfolio size faster. Solo angels might take years to reach 10 companies. Networks give you access to that volume in months.

Sourcing Skills Matter Long-Term

Some community members source deals and bring them to the network. Others just select from deals the network surfaces. The sourcers often get better treatment, priority allocation, better terms, sometimes even carry on deals they bring.

Solo investors are forced to source everything themselves. That skill development is valuable if you ever want to raise a fund or work in VC professionally. Your ability to source and pick winners is your track record.

But sourcing is hard. It requires building relationships with founders, being active in startup communities, and developing a reputation that makes founders want you in their rounds. Most angels aren't good at this initially. Communities provide a bridge while you develop those skills.

Most venture firms have partners who write checks into deals they didn't source. They just saw it as the best deal that came through and wanted to do it. There are two skill sets. One is sourcing and finding deals. The other is being able to diligence deals and figure out why you want to invest.

If you're really good at picking deals and you get a unicorn investment as an angel investor, nobody's questioning where you sourced it. People see thousands of deals. To choose the one in 1,000 deal that ends up going to a unicorn, nobody's questioning you.

The Economics of Membership Fees

Communities charge fees. That's the obvious cost. But you need to look at what you're getting for those fees.

If the network gives you access to deals you wouldn't otherwise see, the math works. If you're seeing the same deals you could access solo, you're paying for nothing.

Some networks add value beyond deal flow. Education, events, connections to other angels who become co-investors or friends. These soft benefits are hard to quantify but matter for long-term success.

Calculate it this way: if a community costs you $2,000 per year but saves you from making one bad $10,000 investment through better due diligence or education, you're ahead. If it connects you to a deal that returns 10x on a $5,000 check, the membership fee is noise.

The real economic question isn't the fee. It's opportunity cost. What could you accomplish solo with the same time and money you'd spend on community involvement?

Speed of Portfolio Building

Networks help you build track record faster through volume. You can invest in more companies, get more reps, and learn faster.

This matters if you have aspirations beyond just being an angel. If you want to raise your own fund, work at a VC firm, or build credibility in the investing world, you need a portfolio. Communities accelerate that timeline.

One Angel Squad member spent three years meeting weekly with Ann Miura-Ko from Floodgate, learning deal evaluation before starting his own syndicate. That kind of apprenticeship used to require top MBA programs or family connections. Now it happens through communities where you show up consistently and add value.

When Solo Makes Sense

Solo investing works better when you already have the assets communities provide. If you have:

• Strong founder networks from operating at high-growth startups
• Domain expertise in a specific sector
• Reputation that attracts deal flow organically
• Time to build relationships and source deals yourself

Then you might not need a community. You're paying for infrastructure you already have.

Eric Bahn built Beat the GMAT and worked as a Product Manager at Instagram before co-founding Hustle Fund. Shiyan Koh scaled NerdWallet from 10 to 450 employees. They had networks and credibility before they started investing. That's different from someone making their first angel investments.

Solo also makes sense if you're investing very part-time and don't want commitment. Communities often expect participation. If you want to write one check per year when the perfect opportunity comes through your network, joining a community might be overkill.

The Hybrid Approach

The most sophisticated angels don't choose. They do both.

They join communities to see volume, learn, and build relationships. But they also cultivate their own deal flow and bring opportunities to the network. They use communities as a platform to develop sourcing skills, not as a replacement for them.

How Angel Squad Bridges Community and Solo Investing

Angel Squad demonstrates how the best communities support both approaches. Weekly virtual events give members consistent exposure to vetted deal flow without the rigid commitment some groups demand. Miss a session? Catch the recording. Traveling for three months? Jump back in when you're ready.

The co-investment structure lets you participate at whatever level makes sense. Write $1,000 checks to build volume and pattern recognition, or go bigger on deals where you have conviction. When Hustle Fund backs a company, members invest on the same terms with no carried interest added. That's community infrastructure that doesn't penalize you for accessing it.

What separates Angel Squad from pure education platforms is the Venture Fellows Program. Members who want deeper involvement can join quarterly cohorts, participate in actual pitch calls with Hustle Fund's team, and help evaluate deal pipeline. 

It's apprenticeship-style learning that develops sourcing skills, not just selection skills. Fellows have gone on to raise their own funds, join VC firms, and build syndicates. That's the hybrid model working: using community to develop capabilities that eventually give you independent deal flow.

Making Your Decision

Don't choose based on what sounds more impressive. Choose based on where you are and where you want to go.

If you're new to angel investing, communities compress your learning curve and give you access you can't build quickly on your own. If you have strong networks and clear deal flow already, solo might make more sense. If you want to develop as an investor while maintaining optionality, hybrid approaches work.

The question isn't "community or solo forever." It's "what do I need right now to get better at this."

Most successful angels started somewhere, learned through volume and mistakes, and built the networks that eventually gave them independent deal flow. Communities just make that progression faster and less expensive in terms of costly mistakes.

Ready to compress your learning curve and start building your track record? Angel Squad gives you immediate access to Hustle Fund's deal flow, educational programming from operators-turned-investors, and a community of ambitious angels building portfolios together. Learn more at hustlefund.vc/squad.

The most successful investors aren't the ones who choose between community and solo. They're the ones who use communities as launchpads to build the skills, networks, and credibility that make solo investing possible. Start where the infrastructure exists, then build from there.