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

Popular culture portrays startup investing through pitch shows and success stories. Actual experience involves different world with specific practices, norms, and realities.

The insider view of what angel investing actually looks and feels like.

How Deal Flow Actually Works

Deal sourcing reality: For most modern angels, opportunities come through community platforms. Monday morning, you receive email listing 3-5 new companies seeking funding. Each includes pitch deck, company overview, and investment terms.

You review these at your convenience. Some are immediately interesting. Most are passed after quick review. Few warrant deeper evaluation.

The volume: Over year, you might see 120-150 opportunities. You'll invest in 6-8. Pass rate is 95%+. This high selectivity is normal and appropriate.

Quality variation: Some weeks feature multiple compelling opportunities. Other weeks feature nothing interesting. Deal flow is lumpy, not consistent. You can't force timing to match your schedule.

The presentation format: Founders usually present via pitch call (30-45 minutes) covering problem, solution, market, traction, team, and funding ask. Q&A follows. These calls happen 1-2 times weekly typically.

As Elizabeth Yin, co-founder and GP of Hustle Fund, explains: "Getting deal flow & education have been the bigger blockers to date" for new investors. Communities solve this by providing consistent pipeline of professionally screened opportunities.

What Evaluation Discussions Actually Sound Like

Among angels: "What do you think of the team?" "Market seems interesting but timing concerns me." "Similar companies tried this and failed, what's different?" "Valuation feels high for this stage." "I like the product but go-to-market strategy is unclear."

These discussions are analytical, not emotional. Experienced angels discuss specific concerns rather than gut feelings. The tone is neutral, not excited or dismissive.

Common evaluation patterns: Does team have relevant domain expertise? Is market large and growing? Does business model have clear unit economics? Are other experienced investors participating? Do terms seem standard for stage?

Red flags frequently mentioned: Solo founder without strong justification. Team with no relevant background. Market that's too small. Business model with unclear monetization. Valuation that's 2x+ above market for stage.

The decision process: Individual angels make individual decisions. No consensus required. But seeing which other angels invest influences decisions. If no experienced angels are participating, that's negative signal.

How Investment Decisions Really Happen

The mental process: "Do I understand market well enough to evaluate this? Does team seem capable based on backgrounds and presentation? Does business model make fundamental sense? Are terms reasonable? Would I regret passing if this succeeds?"

Not "Will this be unicorn?" or "Can I get rich from this?" Those questions come from overconfidence. Realistic questions acknowledge uncertainty.

Decision timeline: For opportunities passing initial screen, angels spend 2-3 hours on evaluation over 1-2 weeks. Read materials carefully. Attend pitch call. Google founders. Research market briefly. Make decision.

The commitment moment: You indicate investment amount through platform. This is commitment you're making $1,000 investment. You'll sign documents and transfer funds in next 2-3 weeks. The moment is administrative, not emotional.

Post-decision feelings: Mix of excitement (this company might succeed) and acceptance (probably won't, but that's okay). Experienced angels don't get overly attached to individual bets.

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." Practice means making decisions regularly, not overthinking each one endlessly.

What Portfolio Management Looks Like Day-to-Day

Quarterly rhythm: Every three months, you spend 90 minutes reviewing entire portfolio. Read quarterly updates from each company. Update tracking spreadsheet with progress or setbacks. Note which companies are executing well versus struggling.

Most updates are mundane: "We grew revenue 15% this quarter. We hired two engineers. We're working on next fundraise." Nothing exciting, just incremental progress.

Some updates are concerning: "Our runway is shorter than expected. Key co-founder left. Major customer cancelled." You note these but typically can't do anything about them.

Rare updates are exciting: "We closed $3M Series A." "Major partnership signed." "Revenue doubled." These happen occasionally but not frequently.

The emotional experience: Mostly boring. Occasionally slightly worrying or mildly encouraging. Rarely exciting. The waiting with limited information tests patience.

Helping portfolio companies: Maybe once quarterly, founder reaches out with specific request. "Do you know anyone in healthcare marketing?" "Can you review our pricing strategy?" You help if you can, decline if you can't. These interactions are pleasant but infrequent.

Cultural Norms in Angel Investing World

Transparency about failures: Experienced angels openly discuss investments that failed. "That company shut down last quarter. Happens all the time." Failure is normal topic, not embarrassing secret.

Realistic expectation setting: Conversations acknowledge high failure rates, long timelines, and modest expected returns. People who overpromise or sound overly optimistic are viewed skeptically.

Generosity with knowledge: Angels share evaluation frameworks, lessons learned, and perspectives freely. Culture emphasizes helping newer angels learn rather than hoarding knowledge.

Respect for founders: Even when passing on opportunities, angels maintain respect for founders. "Not right for my portfolio" rather than "this idea is bad." Founders work incredibly hard and deserve respect regardless of investment decision.

Network reciprocity: Making introductions, sharing opportunities, and helping other angels is normal. The community operates through reciprocity and generosity rather than zero-sum competition.

What Success Looks Like from Inside

Portfolio perspective: After 3 years and 20 investments, you have maybe 8 companies still operating, 12 that failed. The 8 survivors show mixed results. 2-3 are doing well. 3-4 are struggling. 1-2 are unclear.

You don't know which will succeed. The ones you were most excited about might be struggling. The lukewarm bets might be performing best. Outcomes surprise you constantly.

First exit experience: Year 5 or 6, you get email that portfolio company is being acquired. Your $1,000 investment returns $3,500 (3.5x). You're pleased but not celebrating. It's one data point in portfolio, not transformational outcome.

Accumulating perspective: Over years, you develop sophisticated understanding of what drives startup success and failure. This knowledge has professional value beyond direct financial returns.

Network growth: By year 5, you know 30-40 founders, 50+ other angels, and have participated in ecosystem meaningfully. These relationships create opportunities you wouldn't have otherwise.

Financial outcomes: By year 10, you calculate actual portfolio returns. Maybe 2.5x over decade. Net gain of $30,000 on $20,000 invested. Decent outcome but not life-changing. The learning and networks were more valuable than direct financial returns.

What Failure Looks Like from Inside

Early abandonment: Many beginners make 3-5 investments over 18 months, then engagement drops off. They stop reviewing opportunities, skip educational programming, and effectively quit. Portfolio never reaches adequate diversification.

Why people quit: Combination of boredom during years 2-3 when nothing happens, disappointment from inevitable failures, realization that time commitment is real, and gap between expectations and reality.

Portfolio neglect: Some angels maintain minimal engagement but don't help portfolio companies or stay current on ecosystem. Their investments exist but they're not learning or building networks that justify time commitment.

Poor return outcomes: Some portfolios lose money or barely break even. This happens to roughly 25-40% of angels based on available data. The power law returns don't materialize if portfolio lacks that crucial home run investment.

The Insider Wisdom Nobody Tells You

Start slowly: Make 4-6 investments in year one, not 15-20. Give yourself time to learn between decisions. Your early investments will be your weakest regardless of preparation.

Expect surprises: Companies you love will fail. Companies you were lukewarm about will succeed. Markets will shift. Founders will surprise you (positively and negatively). Nothing goes as expected.

Focus on process: You can't control outcomes. You can control quality of evaluation process, discipline about portfolio construction, and consistency of engagement. Process excellence increases odds of success.

Networks matter more than you think: Three years in, the relationships you've built through angel investing create opportunities you couldn't have predicted. Don't underestimate compound effects of networks.

Money is byproduct: If you're doing this primarily for money, you'll be disappointed. If you're doing it for learning, networks, and participation with money as nice bonus, you'll be satisfied regardless of returns.

As Shiyan Koh, co-founder and GP of Hustle Fund, notes: "Great founders can look like anyone and come from anywhere." The insider perspective is recognizing this truth and supporting diverse founders rather than chasing obvious pattern-matching opportunities.

The Reality vs. External Perception

External perception: Angel investing is exciting, glamorous, and potentially lucrative activity where smart investors back unicorns and get rich.

Insider reality: Angel investing is mostly routine evaluation work, patient waiting through boring years, watching most investments fail, and potentially generating modest returns if you're disciplined and lucky.

External perception: Angels are actively involved with portfolio companies, providing strategic guidance and steering companies toward success.

Insider reality: Angels have minimal involvement. Occasional coffee with founder, making introduction when relevant, or providing tactical feedback is extent of participation for most angels at typical check sizes.

The gap between perception and reality is why many beginners quit. They expected excitement and got routine. They expected influence and got periphery. They expected wealth and got learning.

Understanding insider reality before starting prevents disappointment when experience matches reality rather than external perception.

Getting Inside the World

The path in: Join quality community providing access to deal flow, education, and peer network. Angel Squad demonstrates accessible entry: 2,000+ members across 40+ countries, $1,000 minimums, curated opportunities from Hustle Fund's pipeline of 1,000+ monthly applications, weekly education from experienced investors, and realistic cultural expectations about outcomes.

What you'll find: Supportive community of people building portfolios systematically, honest discussions about what works and doesn't, generous knowledge sharing from experienced angels, and realistic expectations about modest outcomes over long timeline.

The world of startup investing is less glamorous but more substantive than external portrayal. If you're drawn to learning, networks, and participation rather than quick wealth, the insider reality is more appealing than the external perception.