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

Every new angel investor asks: should I join a community or go solo?

One sounds structured and supportive. The other sounds independent and flexible.

But which actually gets you to a functional portfolio faster?

Comparing both paths on speed metrics that matter.

Time to First Investment

Community Path: 2-3 months average

Month 1: Join community, consume educational content, observe deal flow Month 2: Continue evaluation, attend programming, build frameworks Month 3: Make first $1,000 investment in curated opportunity

You're investing quickly because infrastructure exists. Deal flow arrives consistently. Terms are standardized. Paperwork is handled.

Solo Path: 12-18 months average

Months 1-6: Learn basics, start networking, attend events, try to meet founders Months 7-12: Build some founder relationships, maybe see a few deals Months 13-18: Finally source opportunity you understand and can access

You're slow because you're building everything from scratch. Deal flow is sporadic. You don't know if terms are fair. Every step has friction.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Getting deal flow & education have been the bigger blockers to date" for new investors. Communities solve both immediately. Solo investing requires solving them yourself.

Winner on speed: Community by 9-15 months

Time to 10-Investment Portfolio

Community Path: 12-18 months

With consistent access to vetted opportunities, you make 1-2 investments per quarter. By month 18, you have 10-12 investments across different stages and markets.

Angel Squad members building portfolios typically hit 10 investments within 12-15 months because deal flow is consistent and evaluation frameworks are taught systematically.

Solo Path: 3-5 years

Deal flow is sporadic. Maybe you see 2-3 interesting opportunities per year through your network. Building to 10 investments takes much longer.

Many solo investors never reach 10 investments. They make 3-4 concentrated bets and stop because sourcing more opportunities is too difficult.

Winner on speed: Community by 2-3 years

Learning Curve to Competence

Community Path: 6-9 months

Month 1-3: Basic literacy and frameworks Month 4-6: Developing judgment and opinions Month 7-9: Contributing valuable perspectives to discussions

Accelerated learning comes from structured education, peer feedback, and high volume of opportunities evaluated. You see 50-100 companies in first six months.

Solo Path: 2-4 years

You're learning through trial and error. Every mistake is your own. Every insight you discover yourself. You see maybe 10-20 companies per year.

Eventually you develop competence, but it takes 3-4x longer because you're reinventing frameworks experienced investors already created.

As Eric Bahn, co-founder and GP of Hustle Fund, emphasizes: "For beginners, a bigger startup portfolio is better. It helps with diversification and helps you learn and get reps in. Investing requires practice like everything else."

Community members get those reps at much higher volume.

Winner on speed: Community by 18-30 months

Deal Flow Development

Community Path: Immediate

Day one you have access to curated deal flow. Hustle Fund's Angel Squad members see opportunities from pipeline of 1,000+ monthly applications immediately upon joining.

You're not building deal flow—you're accessing existing infrastructure.

Solo Path: 2-3 years

Building independent deal flow requires:

• Networking with founders consistently (6-12 months)
• Establishing reputation as helpful (12-18 months)
• Getting warm introductions to quality deals (18-24 months)
• Having founders actively seek you out (24-36 months)

This timeline assumes active networking. Passive approaches take even longer.

Winner on speed: Community by 2-3 years

Portfolio Quality

Community Path: Higher quality, faster

You're seeing deals that passed professional screening. Terms are standardized. Other experienced investors are participating.

Your early portfolio benefits from this curation even while you're learning. You make fewer terrible decisions because infrastructure guides you toward reasonable opportunities.

Solo Path: Lower quality initially, improving over time

Early solo investments often suffer from poor deal selection. You don't know what good looks like yet. You invest in friends' companies or random opportunities.

By year 3-4, your judgment improves and deal quality increases. But those early investments drag down portfolio returns.

Winner on speed and quality: Community significantly

Cost of Education

Community Path: $1,000-3,000 annually in membership

This covers curated deal flow, structured education, community access, and administrative infrastructure. Explicit cost but comprehensive value.

Solo Path: $5,000-15,000 in mistakes

You pay for education through bad investments. That friend's company that went nowhere. That random cold email opportunity with terrible terms. Those concentrated bets in one sector that all failed.

These expensive lessons cost far more than community membership would have.

Winner on cost efficiency: Community dramatically

Time Investment Required

Community Path: 3-5 hours weekly

Structured programming, curated deal flow, organized events. You know exactly when to engage and what to expect.

Solo Path: 10-15 hours weekly initially

Networking events, coffee meetings, cold outreach, research, administrative work. Much of this time doesn't directly improve your investing—it's just infrastructure building.

After 2-3 years, solo time commitment drops to 5-8 hours weekly as you have established systems.

Winner on efficiency: Community by 5-10 hours weekly initially

Independence and Flexibility

Community Path: Less flexibility

You invest in opportunities the community surfaces. Terms are standardized. Process is structured. Some investors find this constraining.

You can supplement with solo deals, but community is your baseline.

Solo Path: Maximum flexibility

You invest in whatever you want, whenever you want, on whatever terms you negotiate. Complete independence.

But this flexibility comes with massive time and learning costs.

Winner on flexibility: Solo (but this advantage is often overrated by beginners)

Long-Term Outcomes

Community Path: More investors reach 15+ investment portfolios

Communities push consistent portfolio building. Structure keeps you engaged. You reach critical mass for portfolio theory to work in your favor.

Solo Path: Most investors quit before reaching 15 investments

Without structure, many solo investors make 3-5 investments then stop. Sourcing becomes too difficult. Learning plateaus. Motivation fades.

The few solo investors who persist and reach 15+ investments often wish they'd started with communities to compress early learning.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." Communities help you find those founders systematically rather than depending on random network encounters.

Winner on outcomes: Community for most investors

The Hybrid Approach

Most successful angels actually use hybrid:

Start with community (Year 1-2): Build foundation, make 10-15 investments, develop judgment Add solo deals (Year 2-3): Supplement with opportunities from personal network Potentially go solo (Year 3+): If you've built strong independent deal flow

This hybrid captures community advantages for learning while building toward independence.

Decision Framework

Choose community if:

• You're new to angel investing (under 10 investments)
• You want to reach 15-investment portfolio quickly
• You value structured learning
• You have limited time (under 10 hours weekly)
• You don't have existing founder network

Consider solo if:

• You've already made 15+ angel investments
• You have exceptional founder network
• You can commit 10-15 hours weekly initially
• You highly value independence
• You're willing to accept 2-3 year slower timeline

Try hybrid if:

• You want best of both approaches
• You have some network but want additional deal flow
• You value learning from community while maintaining independence

The Speed Verdict

Community-based investing is dramatically faster on every metric that matters:

Time to first investment: 9-15 months faster Time to 10-investment portfolio: 2-3 years faster Learning curve to competence: 18-30 months faster Deal flow development: 2-3 years faster Portfolio quality: Higher from day one

The tradeoff is less independence and membership costs. But for most beginners, this tradeoff is obviously worthwhile.

Angel Squad exemplifies why communities win on speed: immediate access to Hustle Fund's curated deal pipeline means you're evaluating quality opportunities from day one rather than spending years building founder network, weekly educational programming from experienced VCs compresses learning curve dramatically, $1,000 minimums enable portfolio construction within 12-18 months, and community of 2,000+ investors provides peer support that maintains engagement.

 Members typically make first investment within 90 days and reach 10-investment portfolios within 12-18 months, timelines impossible for solo beginners.

If your goal is becoming a competent angel investor with a functional portfolio as quickly as possible, community-based investing wins decisively. Solo investing works, but it's objectively slower.