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When I wrote about the startup death email
“So… if early-stage is this brutal, how do you actually play the game as an angel?”
I used to think angel investing was about finding “the next big thing.”
It’s not.
It’s about:
Losing money 7 out of 10 times Watching “the hottest startup in your portfolio” slowly bleed to death And sitting around for 8 years before your one real winner shows up That’s the game.
If you’re still reading, congrats, you’ve got the stomach for it.
But stomach isn’t enough. The graveyard is full of people who lost discipline.
I’ve seen it myself:“Company shutting down. Thanks for believing.”
But here’s the paradox: with the right approach, this game remains insanely lucrative.
A single outlier can 3-4x your entire portfolio. That’s 20–30% IRR, crushing stocks and real estate.
So the real question is: how do you play this unpredictable game without losing your shirt?
Here’s what I’d do if I was starting again.
1. Master the 3 levers of angel investing It all comes down to capital, dealflow, and judgment.
Capital : If you can’t write 10+ checks, don’t play. Diversification saves you.Dealflow : Forget Twitter or AngelList. The best deals travel by whisper networks.Judgment : The hardest of all. And the only thing you control.Naval said it best: “Investing is not about what you say yes to. It’s about what you say no to.”
👉 Without judgment, you’re just gambling.
2. Bet where others won’t If you chase consensus, you’ll overpay for mediocrity.
The real money comes from being non-consensus right .
Think Coinbase in 2012 (crypto? lol).
Everyone laughed, until they didn’t.
👉 If your deals don’t feel a little weird, you’re not aiming high enough.
3. Judge founders, not ideas Here’s the dirty secret: startups always pivot.
Which means: that shiny idea you’re investing in? Dead in 18 months.
The real bet is on people:
Can they survive 5 pivots? Can they recruit killers? Can they still crawl forward when everyone else quits? 👉 Judge the founders, not their Plan A. Because Plans A, B, and C are already doomed.
4. Embrace being unpopular This game will make you look stupid, until it makes you look brilliant.
The best deals won’t get you nods in partner meetings. They’ll get you raised eyebrows.
Being right + early means you’ll look wrong for years. Get used to it.
👉 Play to win, not to fit in.
The two tools that keep you alive in this game This is where most angels blow up: they lose track of their bets. They let winners slip. They overcommit to darlings that never deliver.
That’s why I built these two tools, and why you should absolutely use them too:
✅ Angel Investment Tracker (Notion) Get the tracker →
✅ Angel Value Calculator (Google Sheet) Get the calculator →
With these two, you stop guessing and start compounding.
Founder tools that give you the ultimate unfair advantage 📌 The Ultimate Investors List of Lists (12,000 VCs, FOs, Angels) The Investor List No One Talks About: 140 Family Offices 40 pitch decks that built Unicorns (how Airbnb, Coinbase, Canva got funded) The Ultimate Notion Data Room The Most Successful Investor Update Template The Only Finance Tracker Your Startup Needs SAFE Note Dilution Calculator & Cap Table Builder Co-Founder Agreement Templates
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