The best-documented angel wins are early checks into Apple, Google and Facebook: Mike Markkula's $250,000 for a third of Apple in 1977, Andy Bechtolsheim's $100,000 check to Google in 1998, Jeff Bezos's reported $250,000 in Google, and Peter Thiel's $500,000 in Facebook in 2004. The amounts vary by source, so each figure below is attributed.
"Most successful" is a judgment no one has measured, because no one tracks every angel check ever written. What exists is a handful of well-reported cases. This page sticks to those, names the source for each number, and flags where accounts disagree. It reports history, not a pick list.
Which angel investments are best documented?
Mike Markkula and Apple, 1977
The Computer History Museum describes Markkula as an angel who had made his fortune as a marketing manager at Fairchild Semiconductor and Intel and retired at 32. After Steve Jobs persuaded him in 1977 that personal computers were an opportunity, the museum says he invested $250,000 for a one-third stake, then served as Apple's president from 1981 to 1983 and chairman from 1985 until 1997.
Andy Bechtolsheim, Jeff Bezos and Google, 1998
Wired's account says Bechtolsheim, a Sun Microsystems founder, left a presentation by Larry Page and Sergey Brin for another meeting and offered to write a check, a $100,000 one made out to "Google Inc.", which prompted the pair to incorporate. Google's own June 1999 release announcing a $25 million round led by Sequoia Capital and Kleiner Perkins lists Bechtolsheim and Ram Shriram among the other investors.
Bezos is where sources split. All Things D, relaying Ken Auletta's book Googled, says he invested $250,000 in 1998 at four cents a share, brought to the meeting by Shriram, and held 3.3 million shares at the IPO, while noting that earlier reports had different prices and a $100,000 level. CNBC's 2017 profile instead says he put $1 million into Google.
Peter Thiel and Facebook, 2004
CNNMoney reported that Thiel became Facebook's first big investor in 2004 with $500,000, when Mark Zuckerberg was turning a dorm-room project into a company. By 2012 Thiel and his funds held more than 44 million shares at the IPO, sold 16.8 million of them for $640 million, and sold 20 million more for $395.8 million that August, for just over $1 billion in total. Some of that went to investors in the funds he used, so it is not all his own return.
Why do the reported amounts differ?
Because these deals were private when they happened, and the numbers surfaced later. The Bezos figure comes from a 2009 book, and the Bechtolsheim check from a Wired retrospective written nine years after the fact. Bezos himself appears at $250,000 in one account and $1 million in another, and All Things D notes that even earlier reports of his deal gave different prices.
When you cite a number like this, prefer the closest primary record, such as a prospectus, a regulatory filing or a company's own announcement, say which source you used, and treat round numbers in retellings as approximate. The same discipline applies to any "this angel check became X" claim, including in the best angel investments of all time.
What did these angel investments have in common?
Reading the sources side by side shows patterns that are plain facts rather than lessons about luck:
The investors knew the field. Markkula came from Fairchild and Intel, Bechtolsheim co-founded Sun, Bezos ran Amazon, and Thiel had been PayPal's CEO until eBay bought it in 2002, per CNNMoney.
Money came before the company was formal. The Google check was made out to a company that did not yet exist, and Facebook was a dorm-room project.
Introductions mattered. All Things D reports that Shriram, who had sold his company Junglee to Amazon, brought Bezos to the Google meeting.
Some investors stayed involved. Markkula served as Apple's president and later chairman, which is more than a check.
Some sold, some held. Thiel sold part of his stake in the IPO and set a plan to sell most of the rest the day the lock-up expired, while Bezos reportedly held about 3.3 million shares at Google's IPO.
What do these stories leave out?
Survivorship. We hear about checks that became Apple, Google and Facebook because they became Apple, Google and Facebook. The many angel checks that returned nothing produce no profile, so a list like this says little about the odds on any single bet. Rob Wiltbank, who has studied angel returns, wrote in a 2012 TechCrunch column that an angel is more likely than not to lose money on any single investment, and that 90 percent of cash returns came from the top 10 percent of exits. Seven lessons from angel investments that returned 100x and luck versus skill in angel investing look at that, and the angel portfolio strategy guide covers how portfolios are built around it. More history and cases are in the angel investing section.
Frequently Asked Questions
Q:What is the most famous angel investment ever?
Candidates in the sources above are Markkula's investment in Apple, Bechtolsheim's check to Google and Thiel's early money in Facebook. Which counts as most famous depends on who you ask, and no source ranks them.
Q:Who was the first investor in Google?
Wired credits Andy Bechtolsheim's $100,000 check, made out to "Google Inc." before the company existed on paper, with getting the funding started. All Things D, citing Ken Auletta, names Bezos, David Cheriton and Ram Shriram alongside him as early investors, and Google's June 1999 release lists Bechtolsheim and Shriram.
Q:How much did Peter Thiel invest in Facebook?
CNNMoney reported $500,000 in 2004 and, in August 2012, total proceeds of just over $1 billion from his share sales. Those proceeds include money that belonged to the investors in his funds.
Q:Why do sources disagree on angel check sizes?
Early rounds were private, and the amounts usually surfaced later in books or interviews. Jeff Bezos's Google investment, for example, appears as $250,000 in one account and $1 million in another.
Q:Can a beginner learn from these cases?
Yes, but not by copying them. In the sources above, each investor already worked in the field, such as Markkula at Fairchild and Intel, Bechtolsheim at Sun and Thiel at PayPal, but these cases are the winners that got written about, not the whole picture.