Andy Bechtolsheim

Andy Bechtolsheim made the most consequential angel bet in history: a $100,000 check to Google in 1998, written before the company had even incorporated, after a mere 10-minute demo from Larry Page and Sergey Brin. That single investment swelled to over $1 billion, making it nearly 10,000 times its initial value. No other angel in this list, including #2 Peter Thiel, achieved a multiplier that high from a single write-up, as Thiel's $500,000 Facebook stake grew to roughly $1 billion on a 2,000x return. Bechtolsheim's willingness to bet on an unproven search engine with just a whiteboard and two founders set the standard for lightning-fast, high-trust angel investing.