Angel legends
The cheques everyone quotes, checked
Famous angel investments accumulate legend faster than they accumulate documentation. These 9 are the ones where the facts hold up — what was actually invested, what was actually received, where the sources disagree, and what a small cheque can genuinely take from any of it.
How this section is written
Every figure here is traceable to published reporting, linked on the page it appears on. Where credible outlets disagree — and on Mike Markkula's Apple investment they disagree three ways — we say so instead of picking the most quotable number.
We do not state what a stake is worth today. Those figures move with the share price and are stale the moment they are written, so returns here are anchored to a fixed event: the multiple at a listing, or the amount actually realised on a sale. And we treat "would be worth $X if he had held" as a fact about a decision rather than as a return anybody received.
The list is short and heavily American because the documented record is. That is a real limitation and we would rather state it than pad the section to look comprehensive.
5 investments
The first cheque
Investments made before there was anything to analyse — sometimes before the company legally existed.
Mike Markkula
Apple, 1977
A retired Intel marketing manager backed two men working out of a garage, took roughly a third of the company, and then went to work there — the clearest example on this list of an angel who was not passive.
Read it →$100,000 · August 1998Andy Bechtolsheim
Google, 1998
A Sun Microsystems co-founder wrote a $100,000 cheque to a company that did not yet legally exist, after a demonstration reported to have lasted well under an hour.
Read it →$250,000 · 1998Jeff Bezos
Google, 1998
The founder of one internet company wrote a personal cheque into another, for a reason he later described in terms that had nothing to do with analysis.
Read it →$500,000 for 10.2% · August 2004Peter Thiel
Facebook, 2004
The most-cited angel investment in modern technology, and — because of what happened at the IPO — also the best available lesson in the cost of selling a compounding position early.
Read it →$20m · 2000Masayoshi Son
Alibaba, 2000
A $20m cheque into a Chinese company that barely existed, held for more than two decades — frequently described as the single most profitable venture investment ever made.
Read it →4 investments
The operator edge
Angels who had built or run something first, and turned that into access nobody else had.
Steve Anderson
Instagram, 2010
Baseline Ventures wrote Instagram its first cheque, and the exit that followed contains the most useful footnote in this entire section: the announced price was not the price.
Read it →An $8.4m fund · reported 200×+Chris Sacca
Twitter, from 2009
A former Google employee raised a small fund, concentrated it into a handful of companies, and produced returns that are still used as the benchmark for what a seed vehicle can do.
Read it →$25,000 · reported ~$100m+Jason Calacanis
Uber, 2009-10
The most widely cited small-cheque outcome in angel investing, and the one most often quoted without the portfolio it sat inside.
Read it →$300,000 · 2,200× at listingGarry Tan
Coinbase, 2012
A seed cheque into a company operating in a category most investors would not touch, held through the listing rather than sold into it.
Read it →5 lessons
What they actually teach
The transferable part, drawn from the cheques above rather than from anybody's self-description.
The hardest part is not selling
Three of the investments in this section produced very different outcomes from similar entry positions, and the variable was how long the position was held.
Read it →Lesson 02Invest where your judgement is genuinely better
The famous fast decisions were not fast because the investors were decisive. They were fast because the investors already knew the domain.
Read it →Lesson 03Every story here is a survivor
This section is a catalogue of outliers, and reading it as a set of methods rather than as a tail of a distribution is the most expensive mistake it can cause.
Read it →Lesson 04The winners were bought more than once
The largest positions in this section were accumulated across rounds, not established in a single cheque — which is a capital planning decision made years before the opportunity appears.
Read it →Lesson 05The announced price is not the price
Instagram is remembered as a billion-dollar acquisition. It did not close at a billion dollars, and the gap is the most useful thing in this section.
Read it →Famous angel investments: common questions
What is the most famous angel investment ever made?
How much did the famous angel investors actually make?
Can an ordinary angel repeat any of this?
Why is this list so short and so American?
Read the other half
Every story here is a survivor
These investments were written about because they worked. The cheques the same people wrote into companies that returned nothing are almost entirely undocumented — which is why the failures deserve their own section, and why it is the more instructive one.