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

When VCs advise friends about angel investing, they're more direct than public content allows. They've watched thousands of angel investors and know the patterns that predict success and disappointment.

This is what VCs actually tell their friends when asked "should I angel invest?"

What VCs Tell Friends Who Should Proceed

The profile they encourage: "You've got money you genuinely don't need, you're curious about startups, and you can commit for the long haul. Yes, you should do this. But do it right."

The specific advice: "Join a community with real deal flow. Don't try to invest through your personal network alone. You need volume of quality opportunities to build proper portfolio."

"Make at least 20 investments, ideally 25-30. Same check size every time regardless of how excited you are. The math requires it."

"Expect most investments to fail. Not some, most. If that bothers you emotionally, this isn't for you."

"Think of the learning and network as primary benefits. Returns are bonus. If that framing doesn't work for you, reconsider."

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."

VCs tell friends this directly because they've seen what happens when people ignore portfolio construction.

What VCs Tell Friends Who Should Wait

The profile they caution: "You seem interested but your situation isn't quite right yet. Wait until circumstances improve."

Common reasons to wait:

Financial readiness gaps: "You're close on the money but not quite there. Build your cushion first. Angel investing will still exist in two years."

Time constraints: "Your job is consuming everything right now. You won't sustain the engagement required. Wait until things stabilize."

Life transitions: "You just had a kid / changed jobs / moved cities. Get settled first. Adding angel investing to chaos produces bad outcomes."

Motivation uncertainty: "You seem interested because everyone's talking about it. Spend six months reading about it. If you're still interested, proceed."

The specific advice: "Use the waiting period productively. Read about angel investing. Follow practitioners on social media. Attend free webinars. Build knowledge so you're ready when timing is right."

What VCs Tell Friends Who Should Skip It

The profile they discourage: "Honestly, I don't think angel investing is right for you. Here's why."

Common reasons to skip:

Wrong motivation: "You want to get rich. Angel investing probably won't do that. Median returns are modest. If financial optimization is the goal, index funds are better."

Risk mismatch: "I've seen how you react to investment losses. The stress isn't worth it. Angel investing means watching most investments fail."

Time reality: "You already struggle to maintain commitments. This requires 3-5 hours weekly for years. Be honest about your bandwidth."

Interest mismatch: "You don't actually care about startups. You care about returns. Without genuine interest, you won't sustain engagement."

The specific advice: "There's no shame in not angel investing. It's not for everyone. Put your money in index funds and your time into things you actually enjoy."

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."

VCs tell friends that without commitment to real practice, outcomes will disappoint.

The Uncomfortable Truths VCs Share Privately

Truth 1: Most angel investors don't make money "Median returns are roughly break-even. You might make money, might not. Don't count on it."

Truth 2: Selection skill is overrated "You're not going to pick winners reliably. Nobody does at early stage. Build portfolio and trust the math."

Truth 3: Network quality matters enormously "Where you get deals matters more than how smart you are. Bad deal flow produces bad outcomes regardless of your judgment."

Truth 4: Most people quit too early "The angels I see succeed are the ones who maintain discipline for a decade. Most people lose interest after a few years."

Truth 5: Non-financial value is real "The learning and network building are genuinely valuable. Sometimes more valuable than the returns. Take that seriously."

What VCs Say About Community

The strong recommendation: "Join a community. Seriously. The solo angel path is brutal. Community provides deal flow you can't source yourself, education that accelerates learning, and accountability that maintains engagement."

Why they're emphatic: "I've watched solo angels struggle with terrible deal flow, make avoidable mistakes, and burn out after two years. Community investors sustain practice and produce better outcomes."

The specific guidance: "Find community with institutional deal flow. Angel Squad has access to Hustle Fund's pipeline, which is real institutional quality. That matters."

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

VCs tell friends that community exposure to diverse founders beats the narrow range personal networks typically provide.

The Questions VCs Ask Friends Considering Angel Investing

Question 1: "If you lost every dollar you invested, would it affect your life in any way?"

If yes: Wait until the answer is no. If no: Financial readiness confirmed.

Question 2: "What would you do with the time if you didn't angel invest?"

If answer is productive/valuable: Consider opportunity cost carefully. If answer is less valuable: Time allocation makes sense.

Question 3: "Why do you want to do this?"

If answer involves learning, networks, engagement: Good motivation. If answer is primarily financial: Likely to be disappointed.

Question 4: "How will you feel when your third investment in a row fails completely?"

If answer suggests acceptance: Risk tolerance present. If answer suggests stress: Mismatch with reality.

Question 5: "Are you willing to wait 10 years to know if it worked?"

If genuinely yes: Patience sufficient. If hesitation: Timeline mismatch.

The Bottom Line Advice

What VCs tell friends who ask "should I angel invest?":

"Maybe. It depends on your specific situation. If you have genuinely surplus capital, sustainable time, real interest in startups, and patience for decade-long timelines, then yes. Join a quality community, build proper portfolio, and approach it with realistic expectations."

"If any of those things are missing, wait or skip it. Angel investing is great for the right people in the right situations. It's frustrating and disappointing for everyone else."

"Don't do it because it sounds cool or because someone you know made money. Do it because it genuinely fits your situation and interests. Or don't do it at all."

Angel Squad is what VCs recommend to friends who should proceed: institutional-quality deal flow from Hustle Fund's pipeline, structured education from active VCs, community support for sustained engagement, and $1,000 minimums enabling proper portfolio construction.

The advice VCs give friends is more direct than public content. Use their insider perspective to inform your own decision.