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

I started angel investing 10 years ago. Unlike most content about whether angel investing is "worth it," I can now answer with actual outcomes rather than projections or theory. The results are more nuanced than either promoters or skeptics suggest.

This is what a decade of actual angel investing returns taught me about whether it's worth doing.

The Portfolio Overview

Investment period: 2014-2017 (active deployment). 2017-2024 (portfolio maturation).

Total investments: 24 companies at approximately $2,000 each. Total deployed: approximately $48,000.

Current status: 16 companies failed completely (returned $0). 4 companies returned modest amounts (0.5-2x). 2 companies returned meaningful amounts (3-5x). 2 companies still operating with uncertain outcomes.

Total realized returns: Approximately $78,000 from the 22 companies with determined outcomes.

Return multiple: 1.6x on invested capital (excluding 2 pending outcomes).

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."

My portfolio confirms this precisely: 67% of investments returned nothing.

Was It Financially Worth It?

The honest math: $48,000 invested over 3 years, $78,000 returned over 10 years. Net gain: $30,000. Annualized return: approximately 5-6%.

Compared to alternatives: If I'd put same capital in S&P 500 index fund in 2014-2017, I'd have approximately $110,000-130,000 today. The index fund would have outperformed my angel portfolio significantly.

The sobering conclusion: Purely financially, my angel investing underperformed simple passive investing by substantial margin.

The caveat: Two companies remain pending. One shows strong traction and could produce meaningful return. If that company exits well, portfolio math improves considerably.

What Drove the Returns

Winner concentration: Two investments (8% of portfolio) generated 70% of total returns. This is power law dynamics playing out exactly as theory predicts.

Failure volume: 16 investments returned nothing. Not reduced returns, nothing. Total write-offs. This was emotionally difficult even when intellectually expected.

Modest outcomes dominated: The 4 investments returning 0.5-2x contributed little to portfolio. They weren't failures but didn't drive meaningful value.

The pattern: Returns came from outliers. Everything else was either failure or irrelevant. Portfolio size mattered because more investments meant more chances to capture outliers.

The Mistakes That Cost Real Money

Mistake 1: Concentration in early investments. First 5 investments were $3,000-5,000 each. Later investments were $1,000-2,000. If I'd maintained consistent sizing, I'd have more investments capturing outlier probability.

Mistake 2: Stopping too early. I made 24 investments but should have made 30-40. I stopped when it felt like enough rather than building truly adequate diversification.

Mistake 3: Following without thesis. Several investments were made because impressive people were investing. Without my own thesis, I couldn't evaluate developments intelligently as companies evolved.

Estimated cost of mistakes: If I'd invested $1,500 consistently across 32 investments instead of my actual distribution, portfolio would likely have performed 20-30% better based on outcome distribution.

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."

I didn't build big enough portfolio. I paid for that mistake in missed opportunities.

The Non-Financial Returns

Learning value (substantial): I understand startup mechanics, investment evaluation, and business models far better than I did 10 years ago. This knowledge has professional applications beyond investing.

Network value (significant): Relationships with 24 founders plus dozens of co-investors created network that's produced professional opportunities, introductions, and ongoing value.

Career impact (meaningful): Understanding startup ecosystem improved my performance in my primary career. Better strategic thinking, innovation awareness, and market understanding.

Intellectual engagement (genuine): The decade of engagement was genuinely interesting. Exposure to diverse businesses and founders provided stimulation I valued.

If I quantified these: Learning, network, and career value are probably worth $50,000-100,000 to me over the decade. This is subjective but real.

The Complete Value Assessment

Financial returns: $30,000 net gain (underperformed alternatives)

Non-financial value: $50,000-100,000 estimated equivalent value

Total value: $80,000-130,000 versus $48,000 invested

Time investment: Approximately 1,000 hours over 10 years

Hourly equivalent: $30-80/hour for total value created

Conclusion: When including non-financial value, angel investing was reasonably "worth it" for me. Purely financially, it wasn't.

What I'd Do Differently

More investments: 35-40 instead of 24. Higher outlier capture probability.

Consistent sizing: $1,500 for every investment regardless of conviction. Discipline over enthusiasm.

Better community: I invested mostly through personal network with inconsistent quality. Institutional-quality deal flow would have improved outcomes.

More patience with losers: I wrote off struggling companies mentally before outcomes were determined. Some surprises might have been captured with different mindset.

Earlier start: If I'd started 5 years earlier with same approach, compounding effects would be significant. Time in market matters.

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

Several of my winners were founders who didn't fit typical patterns. Keeping criteria open captured value narrow thinking would have missed.

The Honest Verdict After 10 Years

Was it worth it financially? Marginally. Returns were positive but below alternatives. Not the disaster some predict but not the windfall others promise.

Was it worth it overall? Yes, for me. Learning, network, and engagement value made total experience positive. I don't regret the time or capital.

Would I do it again? Yes, but differently. Better portfolio construction, institutional deal flow, consistent sizing. Same commitment with improved execution.

Should you do it? Depends on whether you'd value the non-financial returns I describe. If you're optimizing purely for financial returns, probably not. If you'd value the learning and network building, possibly yes.

Advice Based on Actual Outcomes

Build bigger portfolio than you think necessary. My 24 investments felt like enough. Data shows 30-40 would have been better.

Maintain strict sizing discipline. My conviction-based sizing was wrong. Consistent checks would have produced better outcomes.

Access quality deal flow. Network-sourced investments were inconsistent quality. Community infrastructure with institutional pipeline would have helped.

Value non-financial returns. These made the experience worthwhile for me. If you wouldn't value them, reconsider whether angel investing fits.

Commit to full timeline. Meaningful outcomes took 7-10 years. Earlier assessment would have been misleading and potentially caused premature abandonment.

The 10-Year Conclusion

Angel investing was worth it for me, but not for the reasons I expected when starting. Financial returns were modest and below alternatives. Non-financial returns were substantial and justified the investment.

If I'd done it better (larger portfolio, consistent sizing, quality deal flow), financial returns would likely have been better. The mistakes were avoidable with proper education and infrastructure.

Angel Squad addresses exactly what I got wrong: curated deal flow from Hustle Fund's pipeline provides quality my network couldn't match, structured education teaches portfolio construction discipline I learned the hard way, $1,000 minimums enable building larger portfolios than my inconsistent approach, and community provides accountability for maintaining consistent practice.

The question isn't whether angel investing is worth it universally. The question is whether it's worth it for you given your values, situation, and approach. My 10 years suggest it can be, with realistic expectations and proper execution.