The best-documented angel investments are the early backers of Google, Facebook and Amazon, because each company's prospectus lists who held shares and who sold in the IPO. The filings show holdings, board dates and sales, but not why the angels invested. No ranking is possible, since most angel deals never publish their terms.
"Best angel investment of all time" is a fight you cannot settle, because most deals never publish their terms. What you can do is study the cases where a securities filing or a first-party company history gives hard numbers. Google, Facebook and Amazon qualify, and between them they show how very different angels reached very different outcomes. This is a case-study read, not a ranking, and every figure below names its source. For the arithmetic of paper multiples, including where Google and Facebook pass 1000x and why Amazon's earliest round stops near 105x, see angel investments that returned 1000x.
Why are these three the best-documented angel deals?
Each company went public in the United States, so its prospectus lists who owned what, at what price, and who sold shares in the offering. That is rare for an angel deal. Other famous angel stories are left out because their terms could not be tied to a filing or a first-party source.
The three also share a feature visible in the filings: the angel money came before any institutional round at that company. Where a filing does not name the buyer of a given share class, this page says so.
What did the first check to Google look like?
Google's own company history says that in August 1998 Sun co-founder Andy Bechtolsheim wrote Larry Page and Sergey Brin a check for $100,000, and that Google Inc. was officially born with that investment. The money moved the team from the dorms to a garage in Menlo Park.
Six years later, Google's final IPO prospectus shows how the early backers had fared. Bechtolsheim held 3,614,080 shares, David Cheriton held 3,404,360, and K. Ram Shriram, who has been a director since September 1998 and runs the angel investment company Sherpalo, held 5,324,660. A group of funds called Angel Investors, controlled jointly by Ron Conway and two partners, held 830,736. At the $85 IPO price those holdings were worth roughly $307 million, $289 million, $453 million and $71 million.
What stands out in the filing: in the offering, Bechtolsheim, Cheriton and Conway's funds each sold 10 percent of their shares and Shriram 5 percent, so most of each position was still held after the IPO. Shriram had been a director for almost six years by then. The prospectus does not say which of these shares came from the first $100,000 check.
What did the first outside check to Facebook look like?
Observer reported that Peter Thiel invested $500,000 in the summer of 2004, after meeting the founders when the company was a three-person dorm-room startup. Facebook's 2012 IPO prospectus shows him as a director since April 2005 and a partner at Founders Fund. It attributes 44,724,100 shares, or 2.5 percent of the company, to him across his personal vehicle, Founders Fund entities and another LLC he manages.
The prospectus footnotes show how he handled liquidity. Rivendell One LLC, his personal holding vehicle, sold about 43 percent of its shares in the IPO at $38, while the rest converted into Class A stock. Observer adds that by February 2020 he had sold down to 9,948 shares.
What stands out in the filing: he joined the board within a year of the check, and he sold in stages, part in the IPO and the rest over the following years.
What did the first money in Amazon look like?
Amazon's 1997 prospectus lists the first outside buyers. In February 1995 Jeff Bezos's father bought 582,528 shares at $0.1717, and in July 1995 a family trust run by his mother bought 847,716 at the same price. Together that is about $245,573 by the prospectus's own figures. In December 1995, director Tom Alberg bought 150,000 shares at $0.3333, about $50,000, and he joined the board in June 1996.
Later money came in at higher prices. Kleiner Perkins bought Series A preferred at $14.05 in a financing the filing dates to June 1996, and Scott Cook and Patricia Stonesifer bought preferred at $40 a share. Amazon went public in May 1997, about two years after the first family purchase.
What stands out in the filing: the earliest outside money came from people close to the founder at the lowest price any outside buyer paid in the document, and a second early buyer took a board seat about six months after buying.
What do the three filings have in common?
These are observations about what the documents show, not explanations of why the deals worked.
Prices rose with each round. Amazon's family shares were priced below Kleiner Perkins' 1996 Series A. Google's prospectus also lists its preferred series at rising prices, though it does not name who bought the first one, and Facebook's filing does not show Thiel's purchase price.
Several angels sat on boards. Thiel has been a Facebook director since April 2005, Alberg joined Amazon's board in June 1996, and Shriram has been a Google director since September 1998.
Holding periods were long. Google took about six years from check to IPO, Facebook about eight, Amazon about two. None of these were quick flips.
Selling was gradual. Google's early angels sold 5 to 10 percent in the IPO, while Rivendell sold about 43 percent of its Facebook shares.
The filings do not say why. They list holdings, prices and dates, not what the angels saw in the founders or the product before the check.
What do these cases leave out?
They are survivors: the winners a prospectus lets us read, with many more deals that never reached one. A list like this says little about the odds on any single bet, and the filings give no hint of how many similar checks returned nothing.
For related reading, how to add value as an angel investor describes what some of these backers did after writing a check, angel investor exit strategies covers how sales like these work, and the role of patience in angel investing covers long holds. For more case studies see the most successful angel investments in history and lessons from the best angel investors in history. More guides are in the angel investing section.
Frequently Asked Questions
Q:What is the best angel investment of all time?
There is no agreed answer, because few angel deals publish their terms. The best-documented are Google, Facebook and Amazon, each backed by angels before any institutional round. Measured by the holdings and sales in their filings, the Google and Facebook positions were the largest in dollar terms at the IPO.
Q:How much did Andy Bechtolsheim invest in Google?
Google's company history says he wrote a $100,000 check in August 1998. Its 2004 IPO prospectus lists his holding at 3,614,080 shares, but it does not say how many came from that first check.
Q:Who was Facebook's first outside investor?
Observer reports that Peter Thiel wrote the first check, $500,000 in the summer of 2004. Facebook's prospectus later listed him as a director since April 2005.
Q:Are these investors really angels?
They invested their own money at the earliest stage, which is the working definition. Some later ran funds, so their holdings at the IPO may include fund vehicles, as the Facebook prospectus shows.