Early Life & Education
Born in 1969 in Edison, New Jersey, Keith Rabois demonstrated entrepreneurial instincts from a young age. His mother was an English teacher who later transitioned into sales, while his father was a CPA. He credits them for instilling certain values, like "if you work hard enough, you can overcome obstacles in your path."
Rabois attended Stanford University, where an incident put the spotlight on him. In his sophomore year, Rabois joined other students in allegedly shouting discriminatory insults outside an instructor‘s home at midnight. While unacceptable today, it was meant to challenge the University‘s policies that were seen as curbing free speech. Rabois was punished by Stanford, but the episode revealed his appetite for taking bold, contrarian stands.
He graduated in 1991 with a degree in Political Science. At Stanford, he met Peter Thiel, who would become the co-founder of PayPal and a recurring figure in Keith‘s journey. After Stanford, Rabois earned his J.D. from Harvard Law School and even clerked at a Circuit Court for a year. However, realizing law was not his calling, he pivoted into the corporate world.
The PayPal Years
Rabois’ first major break came when he joined PayPal in 2000 as an executive. PayPal, which recently went public, was one of the pioneers of online payments. Under CEO Peter Thiel‘s leadership, Rabois came in to manage legal, policy and communications functions.
As PayPal’s user base exploded, contentious battles emerged with eBay, which perceived the former as a threat. Rabois used his legal acumen and lobbying skills to tilt the regulatory conditions in PayPal’s favor. Within two years, PayPal got acquired by eBay for $1.5 billion. The event marked the dawn of the ‘PayPal Mafia’ – influential leaders like Thiel, Rabois, Elon Musk who moved on to launch successful tech ventures.
For Rabois, his time at PayPal reinforced some key startup lessons – solve real consumer pain points, craft regulatory advantages, and blitzscale at the right moment.
The Web 2.0 Phase: LinkedIn & Slide
Fresh from PayPal’s sale, Rabois leveraged his Mafia connections to land senior roles at some of Silicon Valley’s rising stars. He joined LinkedIn when it was still a budding network, owned by Reid Hoffman of PayPal Mafia fame.
Rabois rapidly expanded LinkedIn’s revenue streams through corporate tie-ups and launched new products like LinkedIn Answers. He is credited with building the backbone of LinkedIn’s business modeling during its critical growth phase.
In 2007, Rabois moved to Slide as Head of Corporate Development. Slide, a social gaming startup led by PayPal alum Max Levchin, was taking on giants like Facebook and MySpace in casual gaming. Here Rabois executed partnerships, managed communications and shaped regulatory policy. While Slide got acquired by Google for $182 million in 2010, Rabois’ time there taught him how nimble startups can challenge incumbents.
Square: Highs and Lows
In 2010, Jack Dorsey approached Rabois to join his digital payments firm Square as COO. As one of Square‘s first senior executives, Rabois oversaw recruiting, marketing and built an efficient field organization across North America.
Square also marked a turbulent phase in his career. In 2013, Rabois resigned from Square over an intimacy-related lawsuit threat. While the merits of the lawsuit remain unclear, Rabois maintained his departure was to not cause brand damage. The incident illuminated the gray aspects of personal relationships in high-pressure startups.
However, Rabois continued mentoring Square as a board member for several years. More importantly, Square enlarged his thinking around building financial platforms.
Entering the Big League with Khosla Ventures
The Square episode made Rabois reflect on his career trajectory. While he enjoyed the thrill of startups, he realized he hadn’t built sizable equity yet. So Rabois entered venture capital as a full-time avenue. He joined Khosla Ventures, led by tech billionaire Vinod Khosla in 2013.
Rabois astutely leveraged this chance. He made prescient bets on companies like Stripe, Affirm, DoorDash and Instacart in their infancy. His investments targetted complex domains like AI, finance and logistics. Rabois also guided startups on regulatory practices, crisis management and people strategies.
Within six years at Khosla Ventures, Rabois minted several new unicorns from his initial bets. His Midas touch stemmed from spotting promising startups, aligning with disruptive founders and pushing ambitious goals. Rabois built a formidable reputation in the Valley circles as a top venture capitalist.
The Thiel Reunion & Beyond
After his profitable Khosla stint, Rabois chose to reunite with his PayPal mentor Peter Thiel. He joined Thiel‘s venture firm, Founders Fund as a General Partner in 2019. The move suggested Rabois sought to make bolder plays at the intersections of tech, policy and society.
True to style, Rabois has already stirred new ripples at Founders Fund. He announced a new startup called OpenStore, which acquires e-commerce brands off Shopify to grow them. He also backs futuristic startups in decentralized Web 3.0 and synthetic biology today with huge conviction.
Clearly, Rabois wants to consolidate his gains from past cycles and ride the next big tech wave with policy ingenuity.
Marriage & Personal Life
Rabois married his long-time partner Jacob Helberg, an MD and AI researcher in 2018. While intense in his work persona, Rabois balances it finely in his personal life. In fact in 2020, Rabois and Helberg even moved to Miami from San Francisco seeking better urban infrastructure.
Rabois‘ net worth today is estimated to be over $1 billion owing to his savvy investments. He features among the top 50 of the Midas List – an index of accomplished tech investors globally.