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

Behind every "should I angel invest" discussion are questions people hesitate to ask out loud. They feel too vulnerable, too awkward, or too revealing of insecurity. But these unspoken questions often matter most for making good decisions.

This is the honest answer to the questions you might be afraid to ask.

Question: Will I Actually Make Money?

The question behind it: People want to know if this is financially worthwhile but feel awkward asking directly because it seems greedy or unsophisticated.

The honest answer: Probably not much. Median angel portfolios return 1.0-1.5x over 10 years. After accounting for time investment and opportunity cost, median investors roughly break even or slightly profit.

The fuller picture: Top quartile investors achieve 2.5-4x returns. You might be in that group, but you're statistically more likely to be median. Plan for median, hope for better.

What this means for your decision: If financial returns are your primary motivation, angel investing probably isn't the right choice. Index funds are simpler and likely perform equally well or better for most people.

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 honest answer acknowledges that money-making isn't guaranteed or even likely to be substantial.

Question: Am I Smart Enough to Pick Good Investments?

The question behind it: People worry they lack the expertise to evaluate startups and fear embarrassing themselves with poor decisions.

The honest answer: Selection skill matters less than you think. Even the best investors can't reliably pick winners at early stages. Nobody is "smart enough" to consistently identify which startups will succeed.

The relief: You don't need to be brilliant stock-picker. You need to be disciplined portfolio builder. Following process (diversification, consistent sizing, quality deal flow) matters more than genius evaluation.

What this means for your decision: If you're waiting until you feel smart enough, you'll wait forever. The skill that matters is discipline, not brilliance. That's learnable.

Question: What If I Fail and Lose Everything?

The question behind it: Fear of complete loss is real but feels weak to admit. People worry about financial ruin and personal embarrassment.

The honest answer: You will lose money on most individual investments. That's not failure. That's the expected outcome. Portfolio strategy accommodates this by having enough investments that winners compensate for losers.

The protection: If you invest genuinely surplus capital (money whose loss doesn't affect your life), "losing everything" in angel investing doesn't ruin you. It's disappointing but not catastrophic.

What this means for your decision: Only invest what you can truly afford to lose. If losing $20,000 over 10 years would cause real problems, don't invest that money. If it would cause only mild disappointment, you're appropriately positioned.

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."

Failure on individual investments is expected. Portfolio failure is what diversification prevents.

Question: Will People Judge My Investment Decisions?

The question behind it: Fear of looking stupid to peers, co-investors, or even founders. Worry that poor investments reflect poorly on judgment.

The honest answer: Everyone makes investments that fail. Experienced investors have long lists of companies that didn't work out. This is normal, not shameful.

The perspective: People judge you on process and learning, not individual outcomes. Thoughtful approach that produced bad outcome is respected. Reckless approach that got lucky is not.

What this means for your decision: If fear of judgment is holding you back, recognize that judgment comes from process, not results. Document your thinking, learn from outcomes, and you'll be respected regardless of returns.

Question: Do I Have Enough Money to Do This Properly?

The question behind it: Uncertainty about whether current financial situation qualifies, combined with embarrassment about asking.

The honest answer: You need $15,000-25,000 that you can lock up for 10 years without any impact on your life. If that's available as true surplus (not needed for anything else), you have enough. If not, you don't yet.

The test: Would losing this money completely require any lifestyle adjustment whatsoever? If yes, you don't have enough surplus. If no, you do.

What this means for your decision: Don't stretch to participate. If the capital isn't clearly surplus, wait until it is. Angel investing will still exist when your situation improves.

Question: Is This Just a Rich Person's Hobby?

The question behind it: Wondering whether angel investing is accessible or reserved for the already-wealthy, with concern about fitting in.

The honest answer: Accreditation requirements do require meaningful income or net worth. But angel investing isn't exclusively for the ultra-wealthy. Many angels are professionals who've accumulated modest wealth through careers.

The reality: Community-based angel investing with $1,000 minimums makes portfolio construction accessible to anyone meeting accreditation thresholds. You don't need millions.

What this means for your decision: If you meet accreditation requirements and have surplus capital, you can participate meaningfully. You don't need to be billionaire to build legitimate angel portfolio.

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

Similarly, legitimate angels come from diverse backgrounds, not just inherited wealth.

Question: What If I Realize I Made a Mistake?

The question behind it: Fear of regret, combined with anxiety about being stuck in commitments that can't be undone.

The honest answer: You can't exit angel investments once made. They're illiquid for 7-10+ years. If you realize angel investing wasn't right for you, you can stop making new investments, but existing ones remain.

The mitigation: Start small. First few investments at $1,000 each let you experience the reality before committing full allocation. If you hate it after 3-5 investments, you've only committed $3,000-5,000.

What this means for your decision: Test before fully committing. Observation period and small initial investments reveal fit before you're deeply committed.

Question: Am I Too Old/Young to Start?

The question behind it: Concern that timing is wrong, either too late to matter or too early to be credible.

The honest answer: Age matters less than situation. Young with surplus capital and time? Great. Older with appropriate timeline (10+ years to outcomes) and surplus capital? Also great. Near retirement with short timeline? Poor fit regardless of interest.

The real criteria: Financial readiness, time availability, and appropriate timeline matter more than age.

What this means for your decision: Assess situation honestly rather than using age as excuse or disqualifier.

Question: What If My Spouse/Partner Disagrees?

The question behind it: Relationship tension around financial decisions. Worry about conflict or lack of support.

The honest answer: If angel investing capital is shared, agreement is important. Proceeding over objection creates relationship problems that outweigh any investment benefit.

The approach: Have honest conversation about what angel investing involves: the commitment, the risks, the timeline, and the potential value. If you can't reach agreement, that's important information.

What this means for your decision: Relationship alignment matters. Don't invest shared capital without shared agreement.

The Questions You Should Ask Yourself

Instead of unspoken fears, ask these directly:

"Is this money truly surplus that I won't miss?"

"Would I value the experience even with modest financial returns?"

"Can I commit 3-5 hours weekly for years?"

"Am I genuinely interested in startups, or just interested in returns?"

"Is my life stable enough for decade-long commitment?"

Honest answers to these questions reveal whether angel investing fits your situation better than unspoken worries ever could.

Angel Squad creates environment where honest questions are welcome: educational programming addresses real concerns, community of 2,000+ members shares authentic experiences, and curated deal flow from Hustle Fund's pipeline removes pressure to be "smart enough" to source your own deals.

The questions you're afraid to ask deserve honest answers. Now you have them.