I’ll never forget the first time I got the email .
It was a Sunday.“Important update from the founders.”
I opened it. And there it was:
“We’ve decided to shut down operations effective immediately. We ran out of money, couldn’t close the round, and after a lot of tough conversations, we’ve decided it’s the right call.”
That was it. Years of work, gone in a single paragraph.
Oh and trust, I’ve received A LOT of those emails in recent years.
Here is another one.
The strange thing? I don’t feel emotional when I receive those notes.
Not nearly as emotional as when I lose money trading a stock or crypto 🤬
Why? Because the moment I write an angel check, I already assume the money is gone.
The mindset that saved me When you invest in startups, you can’t expect returns from any particular company.
Instead, you expect returns from the portfolio .
I don’t bet on this one startup making me rich.
I bet that, over 10 years, 1 or 2 of my investments will be such outliers they’ll cover all my losses (and 3X the entire money I’ve invested).
That mindset changes everything.
It means I can shrug when a company shuts down. It means I don’t waste energy clinging to “darling” startups that look promising but never break out.
And it means I can stay in the game long enough to catch the fund returner.
The brutal pattern Here’s what really happens:
Year 1: You invest in 10 startups. $2–5k each. Year 5: 30–50% are dead. Year 7: You’ve made follow-ons. Death rate continues. Year 8: Two are still alive and strong. One looks really good. Year 9: Boom. An acquisition. Year 10: Your one outlier IPOs (in the best-case scenario). The rest? Completely irrelevant.
Two startups returned the whole portfolio. One of them made up >50% of the gains.
That’s the power law .
When even your star goes down But here’s the part nobody talks about:
Sometimes, even your category leader goes down in flames.
I’ve seen companies that raised hundreds of millions, the clear winners in their space, suddenly collapse. (Think Ynsect in insect farming, infarm in indoor farming or several deeptech darlings.)
It hurts. But here’s the truth: until it IPOs or exits, it was always just unrealized value . A line in your investment tracker. Not real cash.
That’s why you can’t get too attached.
The tools I use to stay sane I’ve built two tools to help me (and now you) track angel portfolios without losing perspective:
📊 Angel Investment Tracker (Notion) Angel Value Calculator (Google Sheet)
They help you log deals, track outcomes, and model portfolio returns, without getting hung up on any single bet.
Because that’s the only way to survive this game:
And remember: spray and pray is not sloppy. It’s strategy .
— Yoann
Founder tools that will 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 (all key docs you’ll EVER need) The Most Successful Investor Update Template The Only Finance Tracker Your Startup Needs SAFE Note Dilution Calculator & Cap Table Builder Co-Founder Agreement Templates + Legal Clauses You Can't Forget
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