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

The angel investing education market is filled with instructors who studied investing, wrote about investing, or invested years ago. Learning from people currently writing checks is fundamentally different.

Why active practitioners make the best teachers.

The Practitioner Difference

Current market reality: People writing checks today know current valuations, competitive dynamics, and market conditions. They see what's happening now, not what happened when they were active years ago.

Tested frameworks: Active investors test their evaluation frameworks against real decisions with real consequences. Their teaching reflects what actually works, not what sounds good theoretically.

Honest perspective: People with ongoing skin in the game maintain intellectual honesty that retired educators may lack. Their reputation depends on results, not course sales.

Pattern recognition currency: Active investors see hundreds of opportunities annually. Their pattern recognition stays current with evolving market conditions. Retired investors' patterns may be outdated.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Most of your investments will return $0. You will lose money. So it's important to have great portfolio construction."

This perspective comes from actively managing portfolio where losses are real and ongoing.

What Theoretical Instructors Miss

Market evolution speed: Markets change faster than curricula. Instructors not actively investing teach frameworks that may have worked previously but don't match current conditions.

Emotional reality: Writing checks involves uncertainty, fear, and commitment that teaching doesn't replicate. Theoretical instructors may underestimate emotional dimensions of real investing.

Practical constraints: Time limitations, information gaps, and decision pressure that active investors face daily are absent from theoretical teaching. Real investing is messier than classroom versions.

Feedback loops: Active investors receive constant feedback on decision quality through outcomes. Theoretical instructors lack this correction mechanism. Their errors persist unchallenged.

Identifying Practitioner Educators

Question 1: Are they currently deploying capital? Not "have they invested" but "are they actively investing now?"

Question 2: How much capital have they deployed in past 12 months? Active investors should have recent investment activity.

Question 3: How many opportunities do they see monthly? Active practitioners see high deal volume. Occasional investors see few deals.

Question 4: Can they discuss current portfolio companies? Active investors have ongoing relationships and recent developments to reference.

Red flags: Past tense descriptions of investing career. No mention of recent investments. Inability to discuss current market specifics. Revenue primarily from teaching rather than investing.

The Hustle Fund Approach

Active deployment: Hustle Fund GPs (Elizabeth Yin, Eric Bahn, Shiyan Koh) actively invest across hundreds of startups annually. Teaching reflects current investing practice.

Deal volume exposure: Reviewing 1,000+ applications monthly provides pattern recognition that occasional investors cannot develop. Education includes insights from massive deal flow.

Ongoing portfolio: Current portfolio companies provide real examples. Not historical case studies but active investments with developing outcomes.

Combined credibility: Elizabeth's experience building companies (LaunchBit) and investing (500 Startups). Eric's entrepreneurial background (Beat the GMAT, Instagram). Shiyan's operational experience (NerdWallet). Diverse perspectives from active practitioners.

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."

This advice comes from actively watching portfolio construction outcomes, not theoretical analysis.

What Practitioner Education Includes

Current valuation benchmarks: What caps and terms look like today, not what they looked like five years ago. Active investors know current market pricing.

Recent examples: Investments made in past months provide teaching material. Current decisions illustrate frameworks in action.

Evolving frameworks: Active investors refine approaches based on ongoing experience. Teaching reflects latest thinking, not static historical models.

Market trend awareness: What's emerging in deal flow now. Which sectors are active. Where competition is heating up. Real-time market intelligence.

Honest outcome discussion: Active investors discuss failures alongside successes because they're still experiencing both. More balanced perspective than success-focused theoretical teaching.

How to Access Practitioner Education

Angel investing communities: Quality communities like Angel Squad provide education from active VCs alongside deal flow. Primary access point for most aspiring angels.

Investor podcasts and content: Active investors share perspectives through blogs, podcasts, and social media. Free access to practitioner thinking (though without interaction).

Direct relationships: If you know active angels, they may share insights. Network-dependent access that most beginners lack.

Premium programs: Some active investors offer educational programs. Expensive but provide direct practitioner access. Evaluate whether instructor is genuinely active.

Angel Squad democratizes practitioner access: weekly education from Hustle Fund GPs who actively invest across hundreds of startups, combined with deal flow from their institutional pipeline, at fraction of cost charged by exclusive programs.

Practitioner Wisdom vs. Theoretical Knowledge

On portfolio size: Theoretical: "Diversification reduces risk according to portfolio theory mathematics." Practitioner: "I've watched too many concentrated portfolios fail when the 'sure thing' didn't work out. You need 20+ investments because you can't predict which will succeed."

On evaluation: Theoretical: "Assess team, market, and product using this comprehensive framework." Practitioner: "With limited time, I focus on founder capability and market timing. Everything else is noise at early stages."

On terms: Theoretical: "Understand all provisions and negotiate optimal terms." Practitioner: "At $1,000 checks, terms mostly don't matter. Don't waste time negotiating. Standard terms are fine."

On outcomes: Theoretical: "Expected returns based on historical data suggest X." Practitioner: "Most of my investments have returned zero. Two drove all my returns. That's just how it works."

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere."

This insight comes from actively investing in diverse founders, not theoretical inclusivity statements.

Evaluating Educational Sources

Tier 1: Active fund managers. Currently deploying institutional capital. Highest credibility and current perspective. Hustle Fund GPs exemplify this tier.

Tier 2: Active individual angels. Currently making personal investments. Good perspective but smaller deal volume than fund managers.

Tier 3: Recently retired investors. Stopped investing within past 2-3 years. Perspective somewhat current but beginning to date.

Tier 4: Long-retired investors. Haven't invested actively in 5+ years. Historical perspective may not match current reality.

Tier 5: Theoretical educators. Never invested meaningfully or stopped long ago. Teaching from research and observation rather than practice.

Recommendation: Prioritize Tier 1-2 sources. Use Tier 3 selectively. Approach Tier 4-5 with skepticism about practical applicability.

Maximizing Practitioner Learning

Active engagement: Ask questions during sessions. Challenge frameworks. Request current examples. Passive consumption wastes practitioner access.

Apply immediately: Connect insights to opportunities you're evaluating. Theory without application produces less retention.

Track over time: Follow practitioner perspectives over months and years. See how their thinking evolves. Notice what stays consistent.

Compare practitioners: Different active investors have different approaches. Exposure to multiple perspectives develops nuanced judgment.

The Value Proposition

Theoretical education: Learn frameworks that may or may not apply to current conditions. No deal flow. No community. Often expensive.

Practitioner education through community: Learn from active investors while accessing deal flow, building peer network, and developing through practice. Better outcomes at lower cost.

The comparison: Angel Squad membership ($3,500 lifetime) provides education from active VCs plus deal flow plus community. Premium theoretical courses charge $10,000+ for inferior content without deal access.

Starting With Practitioner Education

Step 1: Join community providing practitioner education. Angel Squad offers weekly programming from Hustle Fund GPs actively investing across hundreds of startups.

Step 2: Attend sessions consistently. Take notes. Engage actively. Ask questions about current market conditions.

Step 3: Apply frameworks to real opportunities through community deal flow. Connect practitioner insights to actual decisions.

Step 4: Build portfolio while learning. Combine practitioner education with practice for optimal development.

Learn from people writing checks, not people writing books about writing checks. The difference in practical value is substantial.