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

Most people asking "is angel investing worth it?" expect a simple yes or no based on financial returns. The real answer is more nuanced and often surprises people on both sides of the question.

This is the honest assessment that challenges conventional assumptions about angel investing value.

The Surprising Truth About Financial Returns

What most people expect: Either fantastic returns (the promotional narrative) or terrible returns (the skeptic narrative).

What actually happens: Median returns are modest, roughly 1.0-1.5x over 10 years. This underperforms index funds when accounting for illiquidity and risk.

The surprise: Most angels report the experience was "worth it" despite these modest financial returns. Something else is driving satisfaction.

Why this surprises people: We assume investment worth equals financial returns. Angel investing challenges this assumption by providing substantial non-financial value that shifts the equation.

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."

The surprise isn't that most investments fail. The surprise is that most angels still consider it worthwhile.

The Surprising Truth About Who Finds It Valuable

What most people expect: Successful angels are those with best financial returns.

What actually happens: Satisfaction correlates weakly with financial returns. Angels with 1.2x returns often report higher satisfaction than those with 2x returns.

The surprise: Expectation setting and value framing matter more than actual outcomes. Those who entered with realistic expectations and valued learning/networks report satisfaction regardless of financial results.

Why this surprises people: We assume better returns create better experience. But perspective and approach determine satisfaction more than outcomes.

The Surprising Truth About Required Expertise

What most people expect: Successful angel investing requires ability to identify winners.

What actually happens: Even the best investors can't reliably pick winners at early stages. Portfolio construction discipline matters more than selection skill.

The surprise: You don't need to be good at picking winners. You need to be disciplined about building diversified portfolio and patient about outcomes.

Why this surprises people: The "expert investor" narrative suggests skill determines outcomes. Reality suggests process discipline matters more than evaluation genius.

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."

The practice matters more than innate selection ability, which surprises those who think angel investing is about genius stock-picking.

The Surprising Truth About Time Investment

What most people expect: Angel investing is primarily capital allocation requiring minimal time.

What actually happens: Angel investing requires 3-5 hours weekly for years. Total time investment of 1,200-1,800 hours over decade.

The surprise: The time investment is substantial and often underestimated. This time has real opportunity cost that must factor into "worth it" calculation.

Why this surprises people: Investment activities are usually passive after decision. Angel investing requires ongoing active engagement.

The Surprising Truth About Learning Value

What most people expect: Learning is nice side benefit of investing.

What actually happens: Many angels report learning value equivalent to $50,000+ executive education. Pattern recognition and business understanding developed through angel investing has significant professional applications.

The surprise: For many angels, learning is primary value and financial returns are secondary benefit.

Why this surprises people: We frame investing as financial activity. The educational component is often undervalued in initial assessment.

The Surprising Truth About Network Value

What most people expect: Networking is optional social component.

What actually happens: Relationships with founders, co-investors, and ecosystem participants create compounding professional value over decades. Career opportunities, partnerships, and collaborations emerge from these networks.

The surprise: Network building may be more valuable than financial returns for professional development.

Why this surprises people: Networking feels intangible and secondary. Its long-term value often exceeds more tangible financial returns.

The Surprising Truth About Who Should Do It

What most people expect: Angel investing is for wealthy people seeking returns.

What actually happens: Angel investing is valuable for professionals seeking learning, networks, and innovation exposure who happen to meet accreditation requirements and have modest surplus capital.

The surprise: The best candidates aren't necessarily the wealthiest. They're those who value what angel investing uniquely provides.

Why this surprises people: Wealth requirements create assumption that wealth optimization is the goal.

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

Similarly, valuable angel investors come from diverse backgrounds with diverse motivations, not just wealth optimization.

The Surprising Truth About Community

What most people expect: Community is nice-to-have addition to individual investing.

What actually happens: Community infrastructure dramatically improves outcomes by providing better deal flow, educational support, operational efficiency, and peer accountability.

The surprise: Solo angel investing is unsustainable for most people. Community membership is closer to requirement than optional enhancement.

Why this surprises people: Investment is often framed as individual activity. Angel investing works better as community activity.

Angel Squad demonstrates this truth: 2,000+ members finding value through collective infrastructure that individual effort couldn't replicate, curated deal flow from Hustle Fund's pipeline exceeding what personal networks provide, and peer support sustaining engagement through challenging periods.

The Surprising Conclusions

Surprise 1: Angel investing often isn't worth it for purely financial purposes, but often is worth it when total value is considered.

Surprise 2: Your approach and expectations determine satisfaction more than actual outcomes.

Surprise 3: Discipline matters more than genius for investment success.

Surprise 4: Time investment is significant and must be valued appropriately.

Surprise 5: Learning and networks may exceed financial returns in total value.

Surprise 6: Community infrastructure is essential, not optional.

What This Means for Your Decision

If you're surprised by financial reality: Recalibrate expectations. Median returns are modest. Plan accordingly.

If you're surprised by non-financial value: Consider whether these benefits would be valuable for you specifically. Career relevance matters.

If you're surprised by time requirements: Assess whether you can sustain 3-5 hours weekly for years. Commitment must be realistic.

If you're surprised by community importance: Plan to join community rather than investing solo. Infrastructure matters.

The Final Surprise

The biggest surprise: Whether angel investing is "worth it" is largely within your control. Those who approach it correctly (realistic expectations, portfolio discipline, community engagement, valuing non-financial returns) consistently report positive experience. Those who approach it incorrectly consistently report disappointment.

The implication: The answer to "is it worth it?" depends more on how you do it than on external factors. You have significant influence over your own outcome through approach and expectations.

Angel Squad helps create positive outcomes: structured approach through community provides framework for success, realistic expectations set through education prevent disappointment, portfolio discipline supported by $1,000 minimums and consistent opportunities, and non-financial value maximized through peer networks and ongoing learning.

The answer might surprise you because it's not predetermined. You have more control over whether angel investing is worth it than most people realize.