Draper invested in Jack Smith and Sabeer Bhatia, who presented him with their company, Hotmail. While numerous publications intimate that he "invented viral marketing" in 1996, this major acclaim was his early support for the founders, due to his idea of automatically attaching a brief advertising message to the bottom of outgoing Hotmail emails. Draper and Jurvetson then coined the term "viral marketing," though the neologism itself is documented as early as a 1989 edition of PC User.
Draper was the first Silicon Valley venture capitalist to invest in China through the global fund DFJ ePlanet. In 2001, Draper negotiated with CEO Robin Li of Baidu to buy 28% of the company on behalf of ePlanet for USD $9 million.
Draper's father, Bill Draper, was an early investor in Skype, and DFJ backed Skype in 2004. The company owned 10% of Skype in 2005 when it was sold to eBay for US$4.1 billion. Draper and Niklas Zennström appeared in the first Skype video together in 2007 at Stanford University.
In 2006, Draper through DFJ was an investor in the Series C venture round of Tesla. In 2007, Draper again invested in Tesla's Series D venture round through Draper Associates.
On June 27, 2014, Draper paid about USD $19 million for nearly 30,000 bitcoins which had been seized by the US Marshals service and auctioned to the public.
On September 23, 2014, Draper told Fox Business that he predicted that one bitcoin would reach $10,000 "in three years"; on January 27, 2015, Draper wagered about $400,000 (which is 2000 bitcoins with $200 price) that the bitcoin will rebound from a recent plunge. The price of a bitcoin crossed $10,000 on November 29, 2017.
In December 2019, he predicted that bitcoin would reach USD $250,000 in 2023.
Draper was one of the first investors in the blood testing start up Theranos, whose founder Elizabeth Holmes was later charged by the SEC with committing massive fraud. In 2018, after the SEC had already charged Holmes, Draper continued to defend her, saying that she had been "bullied into submission".
In early 2014, Draper filed a petition which was accepted by California's Secretary of State Debra Bowen to begin collecting signatures to divide California into six smaller states, arguing that California is "increasingly ungovernable" as one state. However, on September 12, 2014, it was announced the plan fell short of the required amount of valid signatures to land it on the 2016 ballot.
In April 2018 Draper announced collection of "about 600,000" signatures for a new petition to divide California, this time into three new states. In June 2018, the petition collected a sufficient number of signatures to qualify as an initiative in the 2018 general election.
On July 18, 2018, the day before ballots were sent to print, the California Supreme Court blocked the measure from appearing on the November 2018 ballot.
In 2013, Draper launched Draper University of Heroes, an educational program that offers a crash course in entrepreneurship. The university's residential program is based in San Mateo, California, and the curricula are designed by Draper.
When A Venture Capitalist Enters California’s Political Matrix: Innovation Meets The Status Quo, 2018
How to be The Startup Hero: A Guide and Textbook for Entrepreneurs and Aspiring Entrepreneurs, 2017